[ CAS No. 112-80-1 ] {[proInfo.proName]}

Name: 112-80-1|(9Z)-9-Octadecenoic acid|98%
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Quality Control of [ 112-80-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 112-80-1 ]

Product Details of [ 112-80-1 ]

CAS No. :	112-80-1	MDL No. :	MFCD00064242
Formula :	C₁₈H₃₄O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZQPPMHVWECSIRJ-KTKRTIGZSA-N
M.W :	282.46	Pubchem ID :	445639
Synonyms :	9-cis-Octadecenoic acid;9Z-Octadecenoic acid;D 100;C18:1 (cis-9) Fatty acid;Octadecenoic acid (cis-9);Elaidoic acid;9-Octadecenoic Acid;Oleate	Chemical Name :	(9Z)-9-Octadecenoic acid

Calculated chemistry of [ 112-80-1 ]

Physicochemical Properties

Num. heavy atoms :	20
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.83
Num. rotatable bonds :	15
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	89.94
TPSA :	37.3 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-2.6 cm/s

Lipophilicity

Log Po/w (iLOGP) :	4.27
Log Po/w (XLOGP3) :	7.64
Log Po/w (WLOGP) :	6.11
Log Po/w (MLOGP) :	4.57
Log Po/w (SILICOS-IT) :	5.95
Consensus Log Po/w :	5.71

Druglikeness

Lipinski :	1.0
Ghose :	None
Veber :	1.0
Egan :	1.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-5.41
Solubility :	0.00109 mg/ml ; 0.00000385 mol/l
Class :	Moderately soluble
Log S (Ali) :	-8.26
Solubility :	0.00000154 mg/ml ; 0.0000000055 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-5.39
Solubility :	0.00114 mg/ml ; 0.00000404 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	3.07

Safety of [ 112-80-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 112-80-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 112-80-1 ]
Downstream synthetic route of [ 112-80-1 ]

[ 112-80-1 ] Synthesis Path-Upstream 1~13

1
[ 1008-88-4 ]
[ 112-80-1 ]
[ 33421-40-8 ]
[ 87109-10-2 ]

Reference： [1] Patent: US4386209, 1983, A,

2
[ 1008-88-4 ]
[ 112-80-1 ]
[ 33421-40-8 ]
[ 87109-10-2 ]

Reference： [1] Patent: US4386209, 1983, A,

3
[ 112-80-1 ]
[ 504-40-5 ]
[ 555-43-1 ]
[ 2846-04-0 ]

Reference： [1] Chemische Berichte, 1903, vol. 36, p. 2767[2] Chem. Zentralbl., 1904, vol. 75, # II, p. 413

4
[ 112-80-1 ]
[ 627-91-8 ]
[ 1120-34-9 ]

Reference： [1] Journal of the Chemical Society, 1953, p. 2393,2397

5
[ 107-97-1 ]
[ 112-80-1 ]
[ 4316-73-8 ]
[ 110-25-8 ]

Reference： [1] Patent: US5710295, 1998, A,

6
[ 122-32-7 ]
[ 112-80-1 ]
[ 4704-94-3 ]

Reference： [1] Journal of Molecular Catalysis B: Enzymatic, 2014, vol. 102, p. 16 - 24

7
[ 112-80-1 ]
[ 3937-56-2 ]

Reference： [1] Polymer, 2011, vol. 52, # 20, p. 4503 - 4516

8
[ 112-80-1 ]
[ 4494-16-0 ]

Yield	Reaction Conditions	Operation in experiment
47%	at 45℃; for 72 h; Inert atmosphere	Compound 4 was prepared according to a literature procedure.2 Oleic acid (89 g (90percent), 0.315 mol)was transferred into a 250-mL three-necked round-bottomed flask via syringe and out gassed with N2 for 0.5 h. 1,3-Bis-(2,4,6-trimethylphenyl)-2-(imidazolidinylidene) (dichlorophenylmethylene)-tricyclohexylphosphine) ruthenium (267 mg, 0.315 mmol), 2nd generation Grubbs catalyst, was then added. The reaction mixture was stirred with a mechanical stirrer and heated at 45°C, and after ~5min the diacid began to precipitate from the reaction mixture. After 3 days stirring the crude product was quenched with ethyl vinyl ether (40 mL), and excess ether was removed under reduced pressure. The residue was recrystallized several times from a mixture of hexane (300 mL) and ethylacetate (50 mL) to give pure 4 as a white solid (23.5 g, 7.52 mmol, 47 percent). m.p. 97–98 °C. 1H NMR(300 MHz, CD3OD): δ 5.39 (m, 2H, –CH=CH–), 2.27 (t, 4H, J = 7.35 and 7.35 Hz, –CH2–COOH), 1.97 (m, 4H), 1.60 (m, 4H), 1.32 (m, 16H, –CH2–). 13C NMR (75 MHz, CD3OD): δ181.0 (s, –COOH), 131.6 (d, 2C, –CH=CH–), 35.1, 33.7, 30.8, 30.4, 30.3, 30.2, 26.2.
29.75 g	at 45℃; for 24 h; Inert atmosphere	Oleic acid (76 g) was transferred into a 250 mL three-necked round bottom flask and stirred at 45° C. under nitrogen gas for 0.5 hours. Grubbs 2^ndgeneration catalyst (85 mg) was added. The reaction mixture was stirred at 45° C. for around 5 min. The diacid began to precipitate from the reaction mixture. The reaction was kept at this temperature for 24 hours, and then quenched with ethyl vinyl ether (15 mL). The excess ether was removed under reduced pressure. The residue was purified by recrystallization from ethyl acetate and hexanes (1:2) to give 29.75 g of product as a white solid.

Reference： [1] Synthetic Communications, 2014, vol. 44, # 8, p. 1149 - 1154
[2] Patent: US2011/300590, 2011, A1, . Location in patent: Page/Page column 7
[3] Patent: US2015/321992, 2015, A1, . Location in patent: Paragraph 0050
[4] Angewandte Chemie - International Edition, 2017, vol. 56, # 26, p. 7589 - 7594[5] Angew. Chem., 2017, vol. 129, # 26, p. 7697 - 7702,6

9
[ 112-80-1 ]
[ 4494-16-0 ]
[ 5557-31-3 ]

Yield	Reaction Conditions	Operation in experiment
71%	Stage #1: at 45℃; for 24.08 - 72 h; Neat (no solvent)	Oleic acid ((3b), 89 g (90percent, 0.315 mol) was transferred into a 250 mL 3-neck round bottom flask via syringe and out-gassed with nitrogen gas for 0.5 h. 1,3-Bis-(2,4,6-trimethylphenyl)-2-(imidazolidinylidene)(dichlorophenylmethylene)(tricyclohexylphosphine)ruthenium (2, 267 mg, 0.315 mmol), a second generation Grubbs catalyst, was then added; no solvent was utilized. The reaction mixture was stirred with a mechanical stirrer and heated at 45° C. and after about 5 minutes a white precipitate formed. After 24 h reaction, about 10 mg of crude product was removed from the reaction mixture and transferred to a 2 mL dram vial. The crude diacid product (5b, eq. 1) was added to 1 mL of methanol and two drops of conc. sulfuric acid were added. The resulting mixture was heated at 80° C. for 0.5 h (Christie, W. W., Lipid analysis: Isolation, Separation, Identification, and Structural Analysis of Lipids, Oxford, N.Y. Pergamon Press (1982)). The reaction mixture was then quenched with 2 mL of 1M Na₂CO₃, extracted with diethyl ether (3.x.2 mL) and the combined ether layers washed with water (3.x.2 mL). The organic layer was dried with MgSO₄, filtered, solvent removed under reduced pressure, and the methylated diacid 5b characterized by GC/MS: (retention time=14.2 min) and gave an [M]⁺ of m/z 340 (calc., [M]⁺ for 5b is m/z=340.26). The remainder of the crude product was quenched with ethyl vinyl ether (20 mL) and excess ether was removed under reduced pressure. The residue was recrystallized from a mixture of hexane (300 mL) and ethyl acetate (50 mL) twice to give pure 1,18-octadec-9-enedioic acid (5b, eq. 1) as a white solid, m. p., 97.5-98.5° C. (lit. m. p., 88° C. (Van Dam, P. B., et al., J. Am. Oil. Chem. Soc., 51: 389-391 (1974)). Isolated yield: 35 g (71percent). ¹H NMR of 1,18-octadec-9-enedioic acid (CD₃OD, 400 MHz): δ 5.39 (m, -CHCH-, 2H), 2.28 (t, J=7.2 Hz _{7.6 Hz, -CH&2}CO₂H, 4H), 1.98 (m, 4H), 1.60 (m, 4H), 1.32 (m, 16H). ¹³C NMR (CD₃OD, 100 MHz): δ 177.8 (s, CO₂H), 131.6 (s, CHCH), 35.1 (s), 33.7 (s), 30.8 (s), 30.4 (s), 30.3 (s), 30.2 (s), 26.2 (s).

Reference： [1] JAOCS, Journal of the American Oil Chemists' Society, 2006, vol. 83, # 7, p. 629 - 634
[2] Patent: US7534917, 2009, B1, . Location in patent: Page/Page column Sheet 2/6; 6-8; 16; 18
[3] Patent: EP1251135, 2002, A2, . Location in patent: Page 16
[4] Journal of the American Chemical Society, 2012, vol. 134, # 33, p. 13716 - 13729

10
[ 112-80-1 ]
[ 74-85-1 ]
[ 4494-16-0 ]
[ 14436-32-9 ]

Reference： [1] Patent: US2015/336871, 2015, A1, . Location in patent: Paragraph 0071-0081

11
[ 6117-80-2 ]
[ 112-80-1 ]
[ 4494-16-0 ]
[ 75039-83-7 ]
[ 79868-94-3 ]
[ 5557-31-3 ]

Reference： [1] Beilstein Journal of Organic Chemistry, 2011, vol. 7, p. 1 - 8

12
[ 25260-60-0 ]
[ 112-80-1 ]
[ 4494-16-0 ]
[ 101171-21-5 ]
[ 68480-27-3 ]
[ 5557-31-3 ]

Reference： [1] Beilstein Journal of Organic Chemistry, 2011, vol. 7, p. 1 - 8

13
[ 112-80-1 ]
[ 74-85-1 ]
[ 4494-16-0 ]
[ 872-05-9 ]
[ 14436-32-9 ]
[ 5557-31-3 ]

Reference： [1] Patent: EP1251135, 2002, A2, . Location in patent: Page 16-17

[ 112-80-1 ] Synthesis Path-Downstream 1~88

1
[ 60-29-7 ]
[ 67-66-3 ]
oleic acid ; compound of potassium oleate with oleic acid [ No CAS ]
[ 112-80-1 ]
[ 143-18-0 ]

Reference： [1],,p. 35
Chemisches Zentralblatt,1927,vol. 98,p. 1426

2
[ 112-80-1 ]
[ 623-69-8 ]
oleic acid-(β,β'-dimethoxy-isopropyl ester) [ No CAS ]

Reference： [1],1947,vol. 24,p. 163,164
Chem.Abstr.,1947,p. 1136

4
[ 112-80-1 ]
[ 504-40-5 ]
[ 555-43-1 ]
[ 2846-04-0 ]

Reference： [1]Chemische Berichte,1903,vol. 36,p. 2767
Chemisches Zentralblatt,1904,vol. 75,p. 413

5
[ 112-80-1 ]
[ 123-99-9 ]

Yield	Reaction Conditions	Operation in experiment
99.23%	With phosphotungstic acid; potassium permanganate; N-benzyl-N,N,N-triethylammonium chloride; dihydrogen peroxide; oxygen; at 95℃; for 8h;	In a 500-mL four-necked flask equipped with an electromagnetic stirrer, a thermometer and a condenser, 50 g of oleic acid, 5 g of phosphotungstic acid catalyst, 3 g of benzyltriethylammonium chloride was added, and the flow rate of oxygen 20g / L.Rapidly heated to 95 C, adding 2 g of potassium permanganate, adding 200 ml of hydrogen peroxide at a mass concentration of 30% to react for 8 hours. After the reaction, the mixture was placed in a separatory funnel for separation, Manganese in the lower part of the water layer, the oil layer in the above, easy to separate.The separated aqueous phase was crystallized at 0 to 5 C and the manganese dioxide was washed three times with 300 ml of boiling water. The resulting liquid was concentrated to 50 mL at 100 C and cooled at 0 to 5 C to precipitate a white powder. Two parts of the liquid filter, dry, was azelaic acid, the calculated yield of about 99.23%.
		Example 3 The following reagents were added to the apparatus used in Example 1: 100 g of crude oleic acid (purity = 80%, linoleic acid content = 9.9%), 167 cm3f 35% H22 2.0g of H2O4nd 2.0g of Arquad 2HT (registered trade mark). The mixture was heated to 100-104C with stirring and was kept at that temperature for 6 h. Upon completion of the test, the aqueous phase was separated and the organic phase was subjected to continuous extraction with water at 95C. The aqueous phases were cooled to 5C and then filtered to produce 41.6g of azelaic acid.

Reference： [1]Patent: CN104447279,2016,B .Location in patent: Paragraph 0017-0018
[2]Polymer,2011,vol. 52,p. 4503 - 4516
[3]Advanced Synthesis and Catalysis,2014,vol. 356,p. 1782 - 1788
[4]Ullmann's encyclopedia of industrial chemistry,1954,vol. 5,p. 825,826
[5]Chemisches Zentralblatt,1898,vol. 69,p. 439
[6]Patent: US2572892,1949,
[7],1955,vol. 11,p. 5,10
    Chem.Abstr.,1958,p. 16274
[8]Patent: US2773095,1952,
[9]Chemische Berichte,1914,vol. 47,p. 642
    Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti,1914,vol. <5> 23 I,p. 116
[10]Journal fur praktische Chemie (Leipzig 1954),1912,vol. <2>86,p. 539
[11]Patent: US2560156,1947,
[12],1955,vol. 11,p. 5,10
    Chem.Abstr.,1958,p. 16274
[13]Patent: EP621861,1997,B1
[14]Research on Chemical Intermediates,2012,vol. 38,p. 659 - 668
[15]Thermochimica Acta,2014,vol. 585,p. 63 - 70
[16]Advanced Synthesis and Catalysis,2016,vol. 358,p. 3084 - 3092
[17]Patent: DE565158,1931,
    Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 19,p. 445
[18]Patent: US2426954,1944,
[19]Molecules,2020,vol. 25

6
[ 112-80-1 ]
[ 2885-00-9 ]

Reference： [1]Patent: DE665370,1935,
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 25,p. 96

7
[ 112-80-1 ]
[ 115-70-8 ]
[ 68140-98-7 ]

Reference： [1]Patent: US2450807,1946,

8
[ 112-80-1 ]
[ 7541-49-3 ]
[ 204705-68-0 ]

Reference： [1]Patent: DE2812978,1979,
Chem.Abstr.,1980,vol. 92

9
[ 112-80-1 ]
[ 7541-49-3 ]
Dihydrophythyl-oleat [ No CAS ]

Reference： [1]Patent: DE2812978,1979,
Chem.Abstr.,1980,vol. 92

10
[ 114119-34-5 ]
[ 373-49-9 ]
[ 112-80-1 ]
[ 57-10-3 ]
[ 57-11-4 ]

Reference： [1]Tetrahedron Letters,1987,vol. 28,p. 857 - 860

11
[ 114119-34-5 ]
[ 373-49-9 ]
[ 112-80-1 ]
methyl 5-thiaoleate [ No CAS ]
[ 57-10-3 ]
[ 57-11-4 ]

Reference： [1]Tetrahedron Letters,1987,vol. 28,p. 857 - 860

12
[ 112-80-1 ]
[ 57-00-1 ]
[ 76180-96-6 ]

Reference： [1]Agricultural and Biological Chemistry,1984,vol. 48,p. 241 - 243

13
[ 27538-10-9 ]
[ 112-80-1 ]
5-ethyl-2-methyl-4-oleoyloxy-3(2H)-furanone [ No CAS ]
2-ethyl-5-methyl-4-oleoyloxy-3(2H)-furanone [ No CAS ]

Reference： [1]Bioscience, Biotechnology and Biochemistry,1998,vol. 62,p. 2145 - 2154

14
[ 112-80-1 ]
[ 62-31-7 ]
[ 105955-11-1 ]

Yield	Reaction Conditions	Operation in experiment
58%		General procedure: To a stirred solution of the fatty acid (1.0 mmol, 1.0 equiv.) inCH2Cl2 (5 mL) was added CDI (0.178 g, 1.1 mmol, 1.1 equiv.).After 30 min at room temperature, the amine (1.1 mmol, 1.1equiv.) was added. After 12 h, CH2Cl2 (25 mL) was added, followedby saturated aqueous NH4Cl. The mixture was acidified topH 2 by addition of HCl, the organic phase was separated, andthe aqueous layer was further extracted with CH2Cl2 (3 × 10mL). The organic phases were combined, dried over Na2SO4, filtered,and concentrated in vacuo, to give the amide.

Reference： [1]Organic Preparations and Procedures International,1998,vol. 30,p. 699 - 702
[2]Synlett,2019,vol. 30,p. 213 - 217

15
[ 4740-78-7 ]
[ 112-80-1 ]
[ 277749-20-9 ]

Reference： [1]Synlett,2000,p. 248 - 250

19
[ 107-97-1 ]
[ 112-80-1 ]
[ 4316-73-8 ]
[ 110-25-8 ]

Yield	Reaction Conditions	Operation in experiment
	In water; isopropyl alcohol;	EXAMPLE 2 A reactor equipped with a mechanical stirrer, heating mantle, thermometer, and a nitrogen atmosphere, was charged with 35.04 g (0.125 mole) of oleic acid. The oleic acid was heated to 80 C. and 13.8 g (0.125 mole) of solid <strong>[4316-73-8]sodium sarcosinate</strong> was added. This mixture was heated to 170 C. with a constant nitrogen sparge. When the reaction mixture reached 170 C., 11.4 g (0.125 mole) of solid <strong>[4316-73-8]sarcosine</strong> acid was added. The reaction mixture was sampled after ten hours at 170 C. and the conversion based on oleic acid was 84.2%. The crude reaction mixture was dissolved in 60 g of a 50/50 volume ratio of isopropanol and water. This solution was acidified with sulfuric acid to a pH of 1. Upon acidification, the solution formed two layers. The upper layer, containing the product, was separated and concentrated resulting in N-oleoyl <strong>[4316-73-8]sarcosine</strong>.

Reference： [1]Patent: US5710295,1998,A

20
[ 112-80-1 ]
sodium [ No CAS ]
[ 143-19-1 ]

Reference： [1],1935,vol. 42,p. 197
Chemisches Zentralblatt,1936,vol. 107,p. 2241

21
[ 112-80-1 ]
[ 623-57-4 ]
[ 127512-29-2 ]

Yield	Reaction Conditions	Operation in experiment
88.9%		2.41 kg of Nu,Nu'-carbonyldiimidazole is dissolved at room temperature in 6.33 kg of dry acetonitrile. The resultant solution is heated to 25°C. Then 4.0 kg of oleic acid is pumped into the solution over a period of 60 minutes while the reaction temperature is regulated below 35°C by the variation of the addition speed (formation of carbon dioxide gas). After the addition is completed the reaction solution is stirred for additional 90 minutes at 30°C (gas evolution ended). Then 11 g of 1 ,8-diazabicyclo[5.4.0]undec-7-ene is added followed by a solution of 0.83 kg of racemic (R,S)-3-(dimethylamino)- 1 ,2-propanediol in 0.37 kg of dry acetonitrile. Stirring at 30°C is continued for 21 hours. The resultant emulsion is cooled to 25°C and stirring is stopped. Two layers appear. The lower layer is isolated, degassed at 1 mbar/25°C for 200 minutes and finally diluted with 11.7 kg n-heptane. To the solution is added 1.21 kg of basic aluminium oxide and the suspension is stirred for 3 hours at 0°C. The suspension is filtered and the filter residue is washed with 1.5 kg of n-heptane previously cooled down to 0°C. The combined filtrates are homogenized to yield 15.9 kg solution of 4.08 kg pure (2R,S)-DODAP in n-heptane (lot no. MBA-116, assay: 25.7percent, yield:88.9percent).
11.12 g	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In chloroform; at 20 - 30℃; for 1h;	<strong>[623-57-4]3-(dimethylamino)-1,2-propanediol</strong> 2.00 g (16.78 mmol, manufactured by Tokyo Chemical Industry Co., Ltd.), Oleic acid 9.48 g (33.56 mmol, Nisshin Oil Co., Ltd. "EXTRA OLEIN 99"), 4-dimethylaminopyridine 0.41 g (3.36 mmol, product of Koei Chemical Industry Co., Ltd.) was dissolved in 120 g of chloroform. There, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride 7.72 g (40.27 mmol, product of Tokyo Chemical Industry Co., Ltd.) And the mixture was stirred at 20 to 30 ° C. After 1 hour, it was washed with 120 g of ion exchange water and 120 g of 25 wtpercent saline, and 3.0 g of anhydrous magnesium sulfate was added to the organic layer and stirred. The magnesium sulfate was filtered off, The filtrate was desolvated with an evaporator to obtain DODAP (yield: 11.12 g, 17.16 mmol).

Reference： [1]Chemical Communications,2012,vol. 48,p. 5575 - 5577
[2]Patent: WO2012/159704,2012,A1 .Location in patent: Page/Page column 15
[3]Chemistry and Physics of Lipids,2000,vol. 105,p. 189 - 191
[4]Chemical Communications,2011,vol. 47,p. 12613 - 12615
[5]Patent: JP2016/108343,2016,A .Location in patent: Paragraph 0051

22
[ 112-80-1 ]
[ 2415-24-9 ]
10,6'-di-O-oleylcatalpol [ No CAS ]

Reference： [1]Journal of Natural Products,2004,vol. 67,p. 357 - 361

23
[ 112-80-1 ]
[ 123-99-9 ]
[ 112-05-0 ]
[ 2553-17-5 ]

Reference： [1]Journal of Physical Chemistry A,2004,vol. 108,p. 6686 - 6695

24
[ 112-80-1 ]
[ 123-99-9 ]
[ 112-05-0 ]

Yield	Reaction Conditions	Operation in experiment
74%; 75%		General procedure: At ozone generator output 40 mmol O3/h through a solution of 1.41 g (5.0 mmol) of oleic acid 1 in 25 mL of anhydrous alcohol or 20 mL of anhydrous THF or 25 mL of a mixture AcOH-CH2Cl2, 1 : 5, at 0 C was bubbled ozone-oxygen mixture till 5.5 mmol of ozone was consumed. The reaction mixture was flushed with argon and then it was treated by two procedures. a. At 0 1.20 g (17.3 mmol) of NH2OH·HCl was added, the mixture was stirred at room temperature till disappearance of peroxides (iodine-starch test). The solvent was distilled off, the residue was dissolved in CHCl3 (50 mL), the obtained solution was washed with H2O (2 × 15 mL), dried over Na2SO4, and evaporated. Ozonolysis in a mixture of acetic acid and dichloromethane. By method b after chromatographing 1.86 g of residue (SiO2, petroleum ether-tert-butyl methyl ether, 2 : 1) we obtained 0.60 g (75%) of nonanoic acid 3 and 0.64 g (74%) of nonanedioic acid 2, whose IR, 1H and 13C NMR spectra were identic to those previously described [17].
64%; 35%	With ozone; In carbon dioxide; at 15 - 140℃; under 48754.9 - 165017 Torr; for 0.416667h;Autoclave;	(Reference Example 11)An oxygen-containing compound was produced using a batch reaction process.First, oleic acid (0.565 g, 2.00 mmol) was added to a 50 mL stainless steel autoclave, and 28 g of a high-pressure carbon dioxide solution of high-purity ozone containing 2.7 mmol of ozone was supplied from an ozone supply device to give 6.5 MPa at 15C.After stirring for 10 minutes, the temperature was increased to 140C to give 22 MPa, and stirring while heating was conducted for 15 minutes.After the reaction, the autoclave was cooled with ice, and the pressure was reduced; subsequently, the contents were treated with diazomethane, and the reaction mixture was analyzed by gas chromatography using biphenyl as an internal standard. The results confirmed that azelaic acid was obtained in a yield of 64%, and nonanoic acid was obtained in a yield of 35%.
51.5 - 52.7%	With ozone;zeolite activated with manganese; at 95℃;Product distribution / selectivity;	Example 1; Oxidative Ozonolysis of Oleic Acid; A micro falling-film reactor was used for the first part of the reaction, the reaction of ozone and oleic acid. The system consisted of 64 channels with a channel width and a channel depth of 300 mum and a channel length of 75 mm. The channels were operated in parallel and were etched through for educt input and product removal. The cooling channels corresponded in their diameter to the reaction channels. By virtue of the construction of the microreactor, contact between gas and liquid took place solely in the cooled region. The reaction was carried out in countercurrent, although co-current operation is also possible. Technical oleic acid with the following composition was used for the ozonolysis: 5% palmitoleic acid (C16:1-FA), 69% oleic acid (C18:1-FA), 13% linoleic acid (C18:2-FA), 1% linolenic acid (C18:3-FA) and 1% gadoleic acid (C20:1). The other constituents were generally fatty acids with a chain length of C12 to C20. To dilute the reactants, the technical oleic acid was mixed with pelargonic acid in a ratio of 1:2. Owing to their instability, the ozonization products were directly reacted and cleaved with oxygen in microreactors. In such a fixed-bed microreactor consisting of 50 parallel, 70 mm-long reaction channels, with a diameter of 600 mum, with 25 mum thick filters at the outlet of the microchannels, providing for retention of the catalyst powder, having particle diameters of 50 to 80 mum, using zeolite activated with manganese, as described in International Published Application WO 95/21809 A1, the reaction was carried out at 95 C., the reactor being heated with thermal oil. In view of the residence time required, two reactors of this type were arranged in tandem. The reactors for the second reaction step were operated in co-current (trickle flow) with oxygen, the mass ratio between ozonization products and oxygen being adjusted to 90:10. However, countercurrent operation is also possible. In all tests, ca. 0.3 Nl/h oxygen was used per reactor. The heat of reaction was dissipated through the thermal oil. Both reaction steps were carried out continuously. The first reaction step took place at 20 C. 0.1 ml/min. of the liquid fatty acid mixture was used. The quantity of starting gas was varied according to the ozone concentration and the unreacted ozone was catalytically destroyed. The ozonolysis of technical oleic acid was carried out in the first microreaction system. In the second microreaction system, the ozonization products formed were cleaved under the effect of oxygen to form a mixture, with the principal constituents being azelaic and pelargonic acid. The results are set out in Table 1 (recording the mean values of three measurements). The yield of azelaic acid is based on the total input of the technical oleic acid used, i.e., including the saturated constituents. The volume/time yield is based on the empty volumes of the reactors used. The reaction mixture was analyzed by GC. Only minute traces of oleic acid were detected, so that the conversion under the selected conditions in the first reaction step can be regarded as a full conversion. After leaving the second oxidation reactor, ozonides could no longer be detected either. To monitor the GC analyses, relatively large quantities, from repeated test runs, were worked up as follows: the pelargonic acid was first distilled off and the azelaic acid was extracted with water and crystallized, yellowish crystals being obtained. After a recrystallization step, white crystals were obtained. The melting point was between 103 and 105 C., i.e., close to that of pure azelaic acid. GC analysis revealed purities of 97to 99%. The yield of azelaic acid, based on the quantity of technical oleic acid used, was between 51.5 and 52.7% of the theoretical and, by virtue of the excellent dissipation of heat, was almost independent of the ozone concentration in the starting gas. The yield, and hence the selectivity, for azelaic acid exceeded those of conventional processes for the selected starting composition. TABLE 1 Test results (variation of the ozone concentration in the first reaction stage, oxidation under identical conditions at 95 C. in a fixed-bed microreactor) Parameter 1 2 3 4 5 Ratio of oleic to 1:2 1:2 1:2 1:2 1:2 pelargonic acid [kg/kg] Starting fatty acid 0.1 0.1 0.1 0.1 0.1 [ml/min] c(ozone) in the starting 2 5 7 10 13 gas [%] Starting gas [NI/h] 8.5 3.4 2.4 1.7 1.3 Temperature [ C.] 20 20 20 20 20 Pressure [bar] 1.3 1.3 1.3 1.3 1.3 Residence time [s] 120 120 120 120 120 Yield of azelaic acid [%] 51.5 52.1 52.5 52.7 52.3 Volume/time yield 1.12 1.13 1.14 1.14 1.13[t · h-1 · m-3]* Volume/time yield 0.26 0.26 0.27 0.27 0.27[t · h-1 · m-3]** Yield of azelaic acid, based on the volume of the falling-film absorber *Yield of azelaic acid, based on the volume of the falling-film absorber and the two following oxidizers

	With dihydrogen peroxide; ortho-tungstic acid; In water; at 70℃; under 760.051 Torr; for 6h;	0151] The tests described below illustrate the reaction for oxidation of oleonitrile (ON) and also, by way of comparison, that of oleic acid (OA) and of methyl oleate (MO) by means of aqueous hydrogen peroxide, of varying the reaction parameters, i.e. the H2O2 content of the solution injected, and the injection molar ratios and flow rates, at a constant set temperature (70 C.) and under atmospheric pressure. [0152] 100 g of fatty compound and 1.1 g of tungstic acid (H2WO4; Merck 98%) are introduced into a 250 cm3 jacketed reactor comprising a mechanical stirrer, and then stirred and heated at 70 C., said temperature being maintained by circulation of thermostatic water. The aqueous hydrogen peroxide is then added in weight contents which are variable according to the tests, via a peristaltic pump at variable addition speeds according to the tests. The reaction is stopped after 6 h, the aqueous phase is separated for analysis. The remaining organic phase is washed several times with hot water until aqueous hydrogen peroxide has disappeared from the washing water. [0153] The fatty substrates introduced come from the following sources: The fatty substrates introduced come from the following sources: [0154] oleonitrile (ON): Arkema with C16:0: 3%, C18:0: 9.7%, C18:1: 84.7%, C18:2: 1% (% by weight). [0155] oleic acid (OA): Oleon Radiacid 0210 (C18:1: 72%, C18:2: 9% by weight) [0156] methyl oleate (MO): Aldrich Grade Technique (C18:1: 70% by weight) [0157] The operating conditions and the results obtained are given in table 1 hereinafter, in which ?molar ratio? denotes the H2O2/fatty compound molar ratio and NA denotes the presence (Y) or the absence (N) of nonanoic acid, characteristic of the cleavage of the molecule. [TABLE-US-00001] TABLE 1 operating conditions and results Exam- Flow Initial Final ple [H2O2] Molar rate iodine iodine No. Substrate (%) ratio g/min value value NA 1 ON 50 6 0.24 98 4 Y 2 ON 50 4 0.48 98 30 Y 3 ON 50 6 0.48 98 41 Y 4 ON 35 4 0.34 98 37 N 5 ON 50 4 0.48 98 32 Y 6 MO 35 1.8 0.128 91 74 N 7 MO 50 4 0.48 91 80 N 8 MO 50 4 0.48 91 87 N 9 OA 35 1.8 0.128 86 9 N 10 OA 50 2.7 0.5 86 9 Y 11 OA 35 1.8 0.256 86 33 N 12 OA 50 6 0.48 86 26 Y [0158] The oleonitrile oxidation reaction makes it possible to substantially reduce the iodine value of the medium (see example 1) marking the disappearance of the double bonds (formation of diols or cleavage). The H2O2 concentration has an influence on the cleavage of the molecule treated (compare examples 1, 2, 3 and with example 4) resulting in heminitrile formation. [0159] The methyl oleate oxidation reaction results only in a very low conversion of the double bonds regardless of the operating conditions. This oleic acid derivative is not therefore suitable for the formation of diacids by oxidative cleavage. [0160] The oleic acid oxidation reaction allows a reduction in the iodine value of the medium (examples 9 to 12) and the formation of diacids, with a suitable H2O2 concentration.
	With tungstophosphoric acid *15.4 H2O; cetylpyridinium chloride; dihydrogen peroxide; In water; at 85℃; under 760.051 Torr; for 5h;	EXAMPLE 1 In Situ Preparation of the Phase-Transfer Catalyst In a method of oxidative molecular cleavage of a fatty compound and of preparation of carboxylic acids (especially azelaic acid (COOH-(CH2)7-COOH) and pelargonic acid (CH3-(CH2)7-COOH)) according to the invention, a fatty acid composition comprising oleic acid is first prepared from a sunflower oil having a high content of oleic acid (ARTERRIS, Toulouse, France). Enzymatic hydrolysis of the sunflower oil is carried out, during which 22.5 kg of sunflower oil are placed in contact with a solution of a lipase (Lyven, Colombelles, France) of Candida cylindracea in distilled water (20.1 kg) with magnetic stirring at 40 C. for 5 hours. A fatty acid preparation is formed, the composition of which, determined by gas chromatography, is given in Table 1 below.TABLE 1 Fatty acid Composition by mass, % Oleic acid, C18:1 87.6 Linoleic acid, C18:2 4.7 Palmitic acid, C16:0 3.5 Stearic acid, C18:0 3.1 Capric acid, C10:0 0.2 Others 0.9 21 g of this fatty acid preparation comprising 65 mmol of oleic acid are placed in a 250 ml three-necked round-bottomed flask equipped with a cooler, a mechanical stirrer and a heating device. There are added dropwise 2 ml of an aqueous solution of a quaternary ammonium salt (3.36 mmol) selected from the group formed of tetrabutylammonium chloride (n-Bu4NCl, Sigma Aldrich, Saint-Quentin Fallavier, France), tetrabutylammonium bromide (n-Bu4NBr, Sigma Aldrich, Saint-Quentin Fallavier, France), N-cetylpyridinium chloride monohydrate (C5H5N(n-C16H33)3Cl, H2O, Sigma Aldrich, Saint-Quentin Fallavier, France), N-methyl-N,N,N-trioctylammonium chloride (CH3N(n-C8H17)3Cl, Sigma Aldrich, Saint-Quentin Fallavier, France), which is better known by the name "aliquat 336", and N,N,N,N-tetraoctylammonium chloride (N(n-C8H17)4Cl, Sigma Aldrich, Saint-Quentin Fallavier, France). An emulsion of the oleic acid and the solution of the quaternary ammonium salt is formed by mechanical stirring of the resulting mixture.There are prepared by mixing and stirring at ambient temperature for 30 minutes 4 g (1.2 mmol) of tungstophosphoric acid (H3PW12O40.15.4H2O) and 34 ml of 30% oxygenated water (325.0 mmol) in 5 ml of distilled water. The solution of tungstophosphoric acid is added to the emulsion of the oleic acid and the quaternary ammonium salt. The addition of the solution of tungstophosphoric acid to the three-necked flask containing the emulsion is carried out dropwise over a period of 5 minutes. After addition of the solution of tungstophosphoric acid to the emulsion, the reaction mixture is heated to a temperature of 60 C. The reactor is placed and maintained under mechanical stirring (400 rpm) at a temperature of 85 C. and at atmospheric pressure for a period of 5 hours, and the reactor is then allowed to cool to ambient temperature again. The pH of the reaction mixture is adjusted to a value of pH=1 by addition of one volume of an aqueous solution of hydrochloric acid at a concentration of 4 mol/l.In order to separate the carboxylic acids formed and the catalyst, one volume of ethyl acetate is added to the acidic mixture at pH=1 and then the reaction mixture is placed at a precipitation temperature (Tprecip, ambient temperature or temperature below 4 C.) so as to form a precipitate of the catalyst. The precipitate formed is washed with ethyl acetate. The aqueous phase containing the salts is separated from the organic phase in a separating funnel and is then washed with ethyl acetate. The different organic phases are combined, dried over ammonium sulfate and evaporated under reduced pressure.The samples obtained are analyzed and quantified by gas chromatography by means of a Varian chromatograph coupled to a flame ionization detector (FID) and equipped with a capillary column (L 50 m, 0.25 mm, particle size 25 -m) for analysis of the fatty acid methyl esters. The mobile phase is helium (Air liquide, France) at a pressure of 1034 hPa (15 psi) at the head of the capillary column. The temperature of the injector and of the detector is 250 C. The temperature of the oven containing the column is maintained at 100 C. for 5 minutes and is then increased gradually to 180 C. at a rate of 5 C./minute over 10 minutes and is finally increased gradually to 250 C. at a rate of 10 C./minute over 5 minutes and maintained at that temperature for 43 minutes.For the purposes of analysis, a solution of each sample is prepared at a concentration of 10 mg/ml in methyl tert-butyl ether (MTBE). The fatty acids are converted into methyl esters by treatment with trimethylsulfonium hydroxide. Pentadecanoic acid at a concentration of 2 mg/ml is added as internal standard. The results are presented in Table 2 below, in which Tprecip is the precipitation temperature, AZA % and PEA % represent the value of the synthesis and extraction yield of azelaic acid and pelargonic acid, respectively, relative to the starting oleic acid.TABLE 2 PEA, Catalyst prepared in situ Tprecip AZA, % %...
	With dihydrogen peroxide; at 70℃;	The reaction for the oxidative cleavage of oleic acid is performed in a similar manner to that for the oxidative cleavage of oleonitrile (replacement with oleic acid). The oleic acid used is Oleon at a purity of 75%. The reaction takes place at 70 C. without a stream of air and with 144% pure H2O2 relative to the pure oleic acid. Table 5 below gives the composition of the oleic acid cleavage solution and its extract with 58/42 acetic acid (AA)/water (weight ratio).
91%Chromat.; 69%Chromat.	With dihydrogen peroxide; ortho-tungstic acid; In water; for 8h;Reflux;	In a 250-mL round-bottom flask equipped with a condenser, tungstic acid (0.283 g, 1.13 mmol) was suspended in aqueous solution of H2O2 (60 % w/w, 51.2 g,904 mmol) and the system was stirred at 343 K. Oleic acid (36.3 mL, 113 mmol) was added as soon as complete dissolution of tungstic acid was observed. The reaction mixture was stirred under reflux. After 8 h, the mixture was allowed to cool down to room temperature and cool water (50 mL) was added. The reaction mixture was extracted with hot ethyl acetate (4 × 100 mL). The combined organic layers were dried with anhydrous sodium sulfate and evaporated under reduced pressure. The products were analyzed by 1H NMR without further purification of the crude material and by GC after derivatization (tr AA = 11 min, tr PA = 4.2 min, tr DSA = 20 min).
		The 80 g oleic acid and 240 g glacial acetic acid ratio is 40 C in water bath, and inject the ozone reaction 6 hours, to obtain the oleic acid ozonides; wherein ozone by the ozone generator access to the reaction system, the ozone generator power is 50 W, into the ozone generator of the oxygen flow rate is 1.5 L/min; To the obtained oleic acid ozonide oxygen is filled in, the reaction temperature is 120 C, the reaction time is 3 hours, wherein the oxygen flow rate is 0.4 L/min, to obtain the oxidative cleavage product; The obtained for oxidative cleavage product 800 ml 95 C near-boiling water extraction; Extracting the delaminated, oil phase into the reduced pressure distillation, vacuum distillation of steam when the temperature is 120 - 130 C, to obtain 13.5 g crude [...], the purity is 72%; The aqueous phase into the 0 - 5 C refrigerator crystalline 24 hours, filtering, 50 C vacuum dry 24 hours, the obtained unsaturated fatty acid by crude 31.3 g, purity is 90%; the obtained unsaturated fatty acid by the use of the crude product of the 200 ml 90 C near-boiling water to re-crystallization twice, to obtain the pure product of unsaturated fatty acid by 9.4 g, purity of 97%.

Reference： [1]Russian Chemical Bulletin,2005,vol. 54,p. 1847 - 1854
[2]Journal of the American Oil Chemists' Society,2013,vol. 90,p. 133 - 140
[3]Russian Journal of Organic Chemistry,2015,vol. 51,p. 610 - 614
[4]Patent: EP2399897,2011,A1 .Location in patent: Page/Page column 25
[5]Patent: US2007/276165,2007,A1 .Location in patent: Page/Page column 3-4
[6]Green Chemistry,2018,vol. 20,p. 3619 - 3624
[7]Tetrahedron Letters,2005,vol. 46,p. 3201 - 3203
[8]Green Chemistry,2009,vol. 11,p. 986 - 993
[9]RSC Advances,2013,vol. 3,p. 172 - 180
[10]Patent: US2013/345388,2013,A1 .Location in patent: Paragraph 0151-0160
[11]Patent: US2014/371487,2014,A1 .Location in patent: Paragraph 0060-0066
[12]Patent: US2015/299107,2015,A1 .Location in patent: Paragraph 0058; 0059; 0060; 0061
[13]Journal of the American Oil Chemists' Society,2015,vol. 92,p. 1701 - 1707
[14]Patent: CN109180462,2019,A .Location in patent: Paragraph 0023-0049

25
[ 112-80-1 ]
[ 124-19-6 ]
[ 2553-17-5 ]

Yield	Reaction Conditions	Operation in experiment
48.7%		Example 2; Reductive Ozonolysis of Oleic Acid; The same micro falling-film reactor, as described above, was used for the first reaction step of the reductive ozonolysis, the operating parameters, listed in column 4 (Table 1), being adjusted. The ozonization products were again directly reacted in a following microreactor. The reactor used for the reduction was a palladium-coated film reactor. The reactor consisted of 64 channels with a width of 300 mum, a depth of 100 mum, and a length of 75 mm. Hydrogen was used in countercurrent for the hydrogenating cleavage of the ozonides. Azelaic acid semialdehyde and pelargonic aldehyde were mainly formed as products. The products were analyzed by GC. The second reaction step was carried out at 30 C./5 bar pressure. A test was carried out with 0.25 Nl/h hydrogen, the yield of azelaic acid semialdehyde being on average 48.7%.

Reference： [1]Organic Letters,2006,vol. 8,p. 3931 - 3934
[2]Patent: US2007/276165,2007,A1 .Location in patent: Page/Page column 4
[3]Journal of Chemical Research,2005,p. 388 - 390
[4]Chemistry - A European Journal,2013,vol. 19,p. 15012 - 15018
[5]Synthetic Communications,2014,vol. 44,p. 1149 - 1154

26
[ 112-80-1 ]
[ 28319-77-9 ]
[ 4235-95-4 ]

Reference： [1]Chemistry and Physics of Lipids,2005,vol. 137,p. 94 - 99

27
[ 112-80-1 ]
[ 1453-93-6 ]
(Z)-Octadec-9-enoic acid (3S,5R,6S,8R,9R,10R,12R,13R,14R,17S)-6,12-dihydroxy-17-((S)-1-hydroxy-1,5-dimethyl-hex-4-enyl)-4,4,8,10,14-pentamethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester [ No CAS ]

Reference： [1]Biological and pharmaceutical bulletin,2002,vol. 25,p. 861 - 866

28
[ 112-90-3 ]
[ 112-80-1 ]
(9Z)-N-[(9Z)-9-octadecen-1-yl]-9-octadecenamide [ No CAS ]

Reference： [1]Green Chemistry,2018,vol. 20,p. 375 - 381
[2]Journal of the American Chemical Society,2006,vol. 128,p. 16522 - 16523

29
[ 112-80-1 ]
hydrogen [ No CAS ]
[ 2553-17-5 ]

Reference： [1]Chemistry of Natural Compounds,2002,vol. 38,p. 145 - 148

30
[ 112-80-1 ]
[ 1732-09-8 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1838,vol. 28,p. 256

31
[ 112-80-1 ]
platinum [ No CAS ]
[ 505-54-4 ]

Reference： [1]Bulletin de la Societe Chimique de France,1961,p. 218 - 222

32
[ 112-80-1 ]
[ 9012-76-4 ]
chitosan; oleic acid modified (Chit-Ol) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-hydroxy-3-sulfosuccinimide; In DMF (N,N-dimethyl-formamide); water; at 20℃; for 17h;	Oleic acid (4.15 muL, 13.2 mmol, Aldrich) was taken up in DMF (342 muL). To the resulting solution was added sulfo-N-hydroxysuccinimide (29 muL of a 100 mg/mL solution in water, 13.2 mumol, Pierce Chemical Company), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (125 muL of a 20 mg/mL solution in DMF, 13.2 mumol, Aldrich) and the resulting solution was stirred at room temperature. After 1 h, the solution was added to <strong>[9012-76-4]chitosan</strong> (reagent dissolved in 1% HCl in water to a final concentration of 10 mg/mL, 500 muL of concentrate was dissolved in 500 muL water and adjusted to pH 6.5 with 1 N NaOH, 5.0 mg polymer (85% deacylated), 31 mumol in amine, Fluka Chemical Company) in DMF (3.5 mL). The resulting solution was stirred at room temperature for 16 h to afford oleic acid modified <strong>[9012-76-4]chitosan</strong> as a 1 mg/ml solution in 80% DMF/water

Reference： [1]Patent: US2003/235916,2003,A1 .Location in patent: Page 12

Yield	Reaction Conditions	Operation in experiment
	at 60 - 95℃; under 5 - 10 Torr; for 3 - 6h;Conversion of starting material;	0. [06MOL] (16.93g) of oleic acid [(FLUKA CHEMIKA,] Switzerland) was weighed into a three-necked, round-bottom flask equipped with a magnetic stirrer, stopcocks, a vacuum take-off line leading to a liquid nitrogen cold-trap and a vacuum pump. [0.] 01 mol (6.79g) of <strong>[126-14-7]sucrose octaacetate</strong>, SOA, (Fluka Chemika, Switzerland) was added and the mixture was heated to 80-95 degree C in an oil bath with continuous stirring until a homogenous solution was formed. 0.01 % w/w tosylic acid (or [ALKYL SULFONIC] acid polysiloxane, or [BF3.] [0ET2)] was then added. Reaction temperature was then reduced to between 60-75 degree C and 5-10 Torr pressure was applied. The reaction was continued for 3 to 6 hours. The product was taken up in [250ML] of iso-propanol, neutralized with aqueous [1 M NAHCO3,] decolourised with 2. 0g activated charcoal, and filtered. Iso-propanol was then removed by vacuum [DISTIILATION.] Unreacted [OLEIC] acid was extracted with 50x4 ml hexane and kept for reuse. The sucrose fatty ester was [REDISSOLVED] in warm iso-propanol to form 30-40% w/v solution, cool to-4 to 0 degree C and filtered to give unreacted SOA as precipitate. The filtrate iso-propanol was then distilled off to give 70-85% pure [ACETYLATED] sucrose oleate. Repeated hexane extraction and SOA precipitation gave 90-95% pure product (87% yield).

34
[ 8001-23-8 ]
[ 373-49-9 ]
[ 112-80-1 ]
[ 112-79-8 ]
[ 544-70-7 ]
[ 544-70-7 ]
[ 7307-45-1 ]
[ 1072-36-2 ]
[ 60-33-3 ]
[ 60-33-3 ]
[ 29204-02-2 ]
[ 506-30-9 ]
[ 112-85-6 ]
[ 544-63-8 ]
[ 57-10-3 ]
[ 57-11-4 ]
[ 117624-52-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; ethanol; water; at 150 - 215℃; under 7500.75 - 24002.4 Torr; for 0 - 6h;Product distribution / selectivity;	Example 1; A comparison was carried out between reactions carried out in 96% ethanol (according to the invention), and 99.9% ethanol (dry ethanol, comparative example). Both reactions were catalysed by sodium hydroxide, which was used in the form of dry pellets. Safflower oil was used as source for linoleic acid. The sample removed at t=0 hr is the first sample taken when the desired temperature was reached. The reaction mixture was analysed by the fatty acid methyl ester (FAME) method using gas chromatography. The results for the process using 96% ethanol are set out in the following table: The results for the process using 99.9% ethanol are set out in the following table When 96% ethanol was used with addition of extra water, 96.6% of C18:2c was converted in 6 hours. Using dry ethanol gave a conversion of 99.5% in 6 hours. However, the reaction mixture with the lower water content produced higher amounts of the conjugated trans, tans isomer, was very viscous and difficult to stir and to remove samples.; Example 4; COMPARATIVE EXAMPLE; A comparative example was carried out to show the formation of trans, trans isomers at temperatures outside the claimed range. Saffower oil (200 g), caustic soda (45 g) and 95-97% ethyl alcohol (450 ml) were heated under a pressure of 30-32 bar at 210-215 C. for 4 hours. Samples of the reaction mixture were taken at the start of the reaction and at 2 and 4 hours. The reaction mixture was analysed by the fatty acid methyl ester (FAME) method using gas chromatography. The results for the trans, trans conjugated isomer of CLA were as follows:; Example 1; A comparison was carried out between reactions carried out in 96% ethanol (according to the invention), and 99.9% ethanol (dry ethanol, comparative example). Both reactions were catalysed by sodium hydroxide, which was used in the form of dry pellets. Safflower oil was used as source for linoleic acid. The sample removed at t=0 hr is the first sample taken when the desired temperature was reached. The reaction mixture was analysed by the fatty acid methyl ester (FAME) method using gas chromatography. The results for the process using 96% ethanol are set out in the following table: The results for the process using 99.9% ethanol are set out in the following table When 96% ethanol was used with addition of extra water, 96.6% of C18:2c was converted in 6 hours. Using dry ethanol gave a conversion of 99.5% in 6 hours. However, the reaction mixture with the lower water content produced higher amounts of the conjugated trans, tans isomer, was very viscous and difficult to stir and to remove samples.
	With potassium hydroxide; ethanol; water; at 150℃; under 7500.75 - 9000.9 Torr; for 0 - 6h;Product distribution / selectivity;	Example 2; An experiment was carried out to compare processes carried out using ethanol (EtOH) (according to the invention) and propylene glycol (MPG) (comparative example). These reactions were catalysed by potassium hydroxide. Safflower oil was used as source for linoleic acid. The water in the system is from the potassium hydroxide used. Reaction Conditions: The results of FAME analysis of the reaction in ethanol were as follows: The results of FAME analysis of the reaction in propylene glycol were as follows: When 96% ethanol was used as solvent, 99.5% of C18:2c was converted in 2 hours. Using propylene glycol gave a conversion of 90.7% in 2 hours.; Example 3; A series of five experiments was carried out using safflower oil (300 g)>potassium hydroxide pellets and 96% ethanol (250 ml) as the solvent. The amount of potassium hydroxide was varied (72.6 g, 77.5 g, 85.3 g, 103 g and 120.6 g). Since the pellets used contain about 15% water, the water content also varied as a result of varying the amount of potassium hydroxide. The amount of water used in the examples was 10.9%, 11.3%, 11.9%, 13.3% and 14.6%. A measurement of the conversion of linoleic acid showed that the rate of reaction increased with increasing water content, at these levels of water content.
	With potassium hydroxide; water; In propylene glycol; at 150℃; under 7500.75 - 9000.9 Torr; for 0 - 6h;Product distribution / selectivity;	Example 2; An experiment was carried out to compare processes carried out using ethanol (EtOH) (according to the invention) and propylene glycol (MPG) (comparative example). These reactions were catalysed by potassium hydroxide. Safflower oil was used as source for linoleic acid. The water in the system is from the potassium hydroxide used. Reaction Conditions: The results of FAME analysis of the reaction in ethanol were as follows: The results of FAME analysis of the reaction in propylene glycol were as follows: When 96% ethanol was used as solvent, 99.5% of C18:2c was converted in 2 hours. Using propylene glycol gave a conversion of 90.7% in 2 hours.

Reference： [1]Patent: US2005/124818,2005,A1 .Location in patent: Page/Page column 4-5
[2]Patent: US2005/124818,2005,A1 .Location in patent: Page/Page column 4-5
[3]Patent: US2005/124818,2005,A1 .Location in patent: Page/Page column 4-5

35
[ 112-80-1 ]
[ 616-29-5 ]
[ 738604-35-8 ]

Yield	Reaction Conditions	Operation in experiment
84%		Dichloromethane (DCM, 500 ml, Samchun Pure Chemical) and triethylamine (TEA) (24.7 ml, Samchun Pure Chemical) were added to <strong>[616-29-5]1,3-diamino-2-propanol</strong> (3.99 g, 44.25 mmol, Sigma-Aldrich), thereby preparing a reaction solution. After 10 minutes at room temperature, EDC.HCl (25.45 g, 132.76 mmol, Sigma-Aldrich), HOBt (17.9 g, 132.76 mmol, Sigma-Aldrich), oleic acid (25.0 g, 88.51 mmol, Sigma-Aldrich) were added to the reaction solution, and stirred at room temperature for 4 hours. After stirring, dichloromethane (DCM) (500 ml) and water (500 ml) were added to the reaction solution, and the resultant mixture was stirred and allowed to stand, followed by layer separation. All organic layers of the reaction solution were acidified with concentrated hydrochloric acid, stirred for 5 minutes, and then neutralized with a saturated aqueous solution of hydrogen chloride. The organic layers were collected and washed with brine (150 ml), and dried over magnesium sulfate (MgSO4), and filtered, and the filtrate was concentrated under reduced pressure. The residue was recrystallized with methanol (100 ml) to obtain a white solid compound (23 g, yield: 84%). The MS and NMR results of the obtained solid (named ?056N?) are as follows. (0062) MS (ESI pos. ion) m/z: 620 (MH+). 1H NMR (600 MHz, CDCl3): 6.36-6.34 (m, 2H), 5.37-5.31 (m, 4H), 4.25 (br s, 1H), 3.78-3.75 (m, 1H), 3.38-3.27 (m, 4H), 2.22 (t, J=7.8 Hz, 4H), 2.01 (q, J=6.0 Hz, 8H), 1.68-1.60 (m, 5H), 1.33-1.27 (m, 39H), 0.88 (t, J=7.2 Hz, 6H).
23%	at 190℃; for 1h;	Example 12; Preparation of 1,3-di(oleoylamino)propan-2-ol; Oleic acid (5.698 g, 20 mmol) and <strong>[616-29-5]1,3-diaminopropan-2-ol</strong> (1 g, 11 mmol) were placed in a flask and heated at 190 C. for 2 hours. The reaction mixture was cooled to room temperature, then taken up in chloroform and washed with water. The aqueous phase was extracted with chloroform and the organic phases were combined, dried on magnesium sulfate, filtered and evaporated to dryness to yield an oily black residue (6.64 g) which was purified by chromatography on silica gel (eluent:dichloromethane/methanol 99:1). The resulting product was then washed with ether and filtered. Yield: 23% Rf (dichloromethane/methanol 95:5): 0.43 IR: vNH 3306 cm-1; vCO amide 1646 and 1630 cm-1 MP: 88-92 C. NMR (1H, CDCl3): 0.89 (t, 6H, -CH3, J=6.2 Hz); 1.28 (multiplet, 68H, -CH2-); 1.61-1.66 (multiplet, 4H, -CH2-CH2-CONH-); 1.98-2.02 (multiplet, 8H, -CH2-CHCH-CH2-); 2.23 (t, 4H, -CH2-CH2-CONH-, J=7.0 Hz); 3.25-3.42 (multiplet, 4H, -CONH-CH2-CH-CH2-); 3.73-3.80 (m, 1H, -CONH-CH2-CH-CH2-); 5.30-5.41 (multiplet, 4H, -CH2-CHCH-CH2-); 6.36 (multiplet, 2H, -NHCO-). MS (MALDI-TOF): M+1=619 (M+H+); M+23=641 (M+Na+); M+39=657 (M+K+)
23%	at 190℃; for 2h;	Example 7 Preparation of 1,3-di(oleylamino)propan-2-ol Oleic acid (5.698 g, 0.020 mol) and <strong>[616-29-5]1,3-diaminopropan-2-ol</strong> (1 g, 0.011 mol) were placed in a flask and heated at 190 C. for 2 hours. The reaction mixture was cooled to room temperature, then taken up in chloroform and washed with water. The aqueous phase was extracted with chloroform and the organic phases were combined, dried on magnesium sulfate, filtered and evaporated to dryness to yield an oily black residue (6.64 g) which was purified by chromatography on silica gel (eluent:dichloromethane/methanol 99:1). The resulting product was then washed with ether and filtered. Yield: 23% Rf (dichloromethane/methanol 95:5): 0.43 IR: nuNH 3306 cm-1; nuCO amide 1646 and 1630 cm-1

Reference： [1]Patent: US2017/239164,2017,A1 .Location in patent: Paragraph 0061-0062
[2]Patent: US2006/154984,2006,A1 .Location in patent: Page/Page column 37
[3]Patent: US2006/35977,2006,A1 .Location in patent: Page/Page column 23-24

36
[ 3198-49-0 ]
[ 112-80-1 ]
[ 124285-49-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	lipase;	EXAMPLE 5 Preparation of ethyl 6-O-(cis-9-octadecenoyl)-D-glucopyranoside The title compound was obtained as a crude product (1305 g, 90% monoester, 5% <strong>[3198-49-0]ethyl D-glucopyranoside</strong>, 5% diesters) according to example 1 using <strong>[3198-49-0]ethyl D-glucopyranoside</strong> (606 g, 2.9 mol), cis-9-octadecenoic acid (1111 g, 3.9 mol) and immobilized lipase (30.5 g). The reaction was complete in 48 hours.

Reference： [1]Patent: US5191071,1993,A

37
[ 102-09-0 ]
[ 112-80-1 ]
[ 18063-03-1 ]
N-2,6-difluorobenzoyl-O-phenylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With potassium hydroxide; acetic acid; In toluene;	EXAMPLE 9 Preparation of N-2,6-difluorobenzoyl-O-phenylcarbamate A mixture of <strong>[18063-03-1]2,6-difluorobenzamide</strong> (48 g, 0.3 mol), potassium hydroxide pellets (19.68 g, 85.5%), oleic acid (1.38 g) and toluene was subjected to azeotropic distillation for 11/2 hours. Diphenylcarbonate (66 g, 0.31 mol) was added, and after a further 15 minutes at distillation temperature the mixture was allowed to cool to ambient temperature. The precipitated solid was filtered off from the reaction mixture and was treated with aqueous acetic acid, as in Example 7, to give N-2,6-difluorobenzoyl-O-phenylcarbamate (64 g, 77%) mp 149 C.

Reference： [1]Patent: US5189197,1993,A

38
[ 31608-22-7 ]
[ 112-80-1 ]
[ 145437-64-5 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In tetrahydrofuran;	A (Z)-9-octadecenoic acid 4-hydroxybutyl ester To a stirring solution of 2.0 g (7.0 mmol) of oleic acid and 1.6 g (7.0 mmol) of 2-(4-bromobutoxy)tetrahydro-2H-pyran in 20 mL of tetrahydrofuran is added 2.3 g (7.1 mmol) of cesium carbonate and the reaction mixture is stirred overnight at room temperature. The reaction mixture is poured into water and extracted with three 100 mL portions of ether. The combined organic layers are dried over MgSO4 and concentrated in vacuo affording 2.9 g (100%) of (Z)-9-octadecenoic acid 4-[(tetrahydro-2H-pyran-2-yl)oxy]butyl ester.

Reference： [1]Patent: US5242945,1993,A

39
aqueous sodium chloride [ No CAS ]
[ 79-37-8 ]
[ 112-80-1 ]
[ 623-57-4 ]
rac-1,2-dioleoyl-3-N,N-dimethylaminopropane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.92 g (84%)	With pyridine; In methanol; diethyl ether; hexane; water; benzene;	A. Synthesis of +-1,2-dioleoyl-3-N,N-dimethylamino-propane (AL-1). This compound was prepared by the method of Leventis et al. (Biochim. Biophys. Acta 1029:124-132, 1990). Three ml (35 mmol) of oxalyl chloride was added to 1.0 g (3.5 mmol) oleic acid dissolved in 10 ml benzene and stirred at room temperature for 1 h. After removal of solvent and excess oxalyl chloride under vacuum, the acid chloride was dissolved in 5 ml diethyl ether, and a further 5 ml of ether containing 0.20 g (1.7 mmol) of 3-N,N-dimethylamino-1,2-propanediol and 0.15 g pyridine was added. The resulting mixture was stirred at room temperature for 30 minutes before quenching with 1 ml methanol and removing solvents under vacuum. The crude product was dissolved in 50 ml hexane and washed with 2*25 ml 0.1M potassium hydroxide in methanol/water (1:1) followed by 25 ml 0.1M aqueous sodium chloride. Drying over anhydrous sodium sulphate and removal of hexane under vacuum gave a slightly yellow oil. Column chromatography on silica gel (70-230 mesh), eluding with ethyl acetate, gave 0.92 g (84percent) of pure product (TLC, Rf =0.5).

Reference： [1]Patent: US5595756,1997,A

40
[ 8001-23-8 ]
[ 373-49-9 ]
[ 112-80-1 ]
[ 544-70-7 ]
[ 544-70-7 ]
[ 1072-36-2 ]
[ 57-11-4 ]

Yield	Reaction Conditions	Operation in experiment
		1. Conversion of Conjugated Linoleic Acid; After adding 500 ml of propylene glycol to a synthetic reactor, where a temperature of 175 C. was maintained, if the temperature came down to 130 C., 250 g of NaOH was added to the synthetic reactor and completely dissolved. Next, the resulting solution was stirred until the temperature came up to 175 C. 1 kg of Safflower oil (linoleic acid of 75%) was added to the solution to carry out a conjugated isomerization reaction for one and a half hours. Then, after cooling the solution at a temperature of 50 C., the conjugated isomerization reaction was terminated. When the temperature came down to 50 C., phosphoric acid was added slowly to the reactant to adjust the pH value to 1. After stationing under this condition, the lower part of the reactant was removed and the conjugated linoleic acid layer in the upper part was washed by distilled water. This process was executed two to three times to remove impurities dissolved in water completely. 952 g of the conjugated linoleic acids (95.2%) obtained in this step contain unreacted linoleic acids of 0.5% or less and trans-9,trans-11-conjugated linoleic acids of 0.8% or less. The method for preparing unsaturated fatty acids in a high purity from fat and oil fatty acids in accordance with the present invention is described in a flowchart of FIG. 1. FIG. 2 shows the analysis result of the conjugated linoleic acids obtained in step 1 using a gas chromatography analyzer. As shown in FIG. 2, the conjugated linoleic acid converted contains palmitoleic acid of 6.59%, stearic acid of 2.86%, oleic acid of 14.20%, cis-9,trans-11 conjugated linoleic acid of 37.36%, trans-10,cis-12 conjugated linoleic acid of 38.91% and trans-9,trans-11 conjugated linoleic acid of 0.08%. Accordingly, it can be understood that the method for preparing unsaturated fatty acids of the present invention can minimize the formation of trans-9,trans-11 conjugated linoleic acids, which are carcinogenic substances.

Reference： [1]Patent: US2006/229461,2006,A1 .Location in patent: Page/Page column 3; Sheet 2

41
[ 1008-88-4 ]
[ 112-80-1 ]
[ 33421-40-8 ]
[ 87109-10-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium amide; In water; toluene;	EXAMPLE 10 Amination of 3-Phenylpyridine A mixture of 33.2 g (0.85 mole) of sodamide, 450 cc of toluene containing 0.1 cc of oleic acid, and 126.9 g (0.82 mole) of 3-phenylpyridine was placed in a liter Magne Drive, equipped as described in Example 2. The autoclave was closed and purged of air with ammonia, pressurized to 45 psi with ammonia and then to 215 psi with nitrogen. Cooling water was turned on the reflux condenser. The autoclave was heated with stirring to 150 C. and maintained between 150 and 160 C. for about 3 hours, during which time hydrogen evolved and passed through the pressure relief valve. The autoclave was cooled to room temperature and vented to atmospheric pressure. The reaction mixture was carefully hydrolyzed with 100 cc of water. The toluene phase was separated and the aqueous phase was extracted twice with 25 cc of toluene. The toluene extracts were combined and distilled to give 46.9 g of a mixture of 2-amino-5-phenylpyridine and 2-amino-3-phenylpyridine boiling 201-227 C. at 24 mm Hg. A GLC analysis showed that the ratio of 2,5-isomer:2,3-isomer was 38.1:1. The 2-amino-5-phenylpyridine, crystallized from pyridine, had a melting point of 136-137 C.

Reference： [1]Patent: US4386209,1983,A

42
[ 112-80-1 ]
[ 143-19-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In water;	A second composition according to the invention was prepared with the following formulation in terms of mass fractions of ingredients (w/w), this second composition only differing from the first one by the use of a fatty acid not previously formed into a salt.This second composition was prepared according to the following process of preparation: - Step (i): in a suitable vessel, oleic acid was introduced and mixed with the water, until a homogenous dispersion was obtained.

Reference： [1]Patent: WO2007/6334,2007,A1 .Location in patent: Page/Page column 8
[2]RSC Advances,2016,vol. 6,p. 3462 - 3469
[3]Crystal Growth and Design,2016,vol. 16,p. 6922 - 6932
[4]ChemistryOpen,2018,vol. 7,p. 159 - 168
[5]Journal of the American Chemical Society,2020,vol. 142,p. 2956 - 2967
[6]Russian Journal of Physical Chemistry,2020,vol. 94,p. 1104 - 1110
Zh. Fiz. Khim.,2020,vol. 94,p. 829 - 836,8

43
[ 112-80-1 ]
[ 127-47-9 ]
[ 631-88-9 ]
[ 68-26-8 ]

Yield	Reaction Conditions	Operation in experiment
69%	With Novozyme 435 (from Candida antarctica immobilized on acrylic resin); Amberlyst A-21; In toluene; at 20℃; for 15h;Enzymatic reaction;Product distribution / selectivity;	Example 29; Preparation of Retinyl Oleate in the Presence of Amberlyst A-21; Retinyl acetate (1.00 g; 3.04 mmol) and dried Amberlyst A-21 (0.5 g) were combined with 8.5 mL of toluene. Oleic acid (1.72 g; 6.09 mmol; 2.0 equiv) was added followed by 120 mg of Novozyme 435. The reaction mixture was stirred at RT for 15 h, at which point a sample was removed and analyzed by HPLC, indicating 89.2% conversion to retinyl oleate with 9.0% retinyl acetate and 1.9% retinol. The reaction mixture was filtered and concentrated, then concentrated twice with heptane (10 mL each). The residue was dissolved in heptane (15 mL) and washed with 2×20 mL with a 1:1 mixture of 10% aqueous potassium carbonate and methanol. The organic layer was washed further with a mixture of saturated sodium bicarbonate (2.5 mL), water (7.5 mL), and methanol (10 mL), dried (sodium sulfate) and concentrated to afford 1.16 g (69%) of a yellow oil. HPLC (4.6×150 mm Zorbax SB-C8 column [Agilent], 3.5mu thickness, methanol eluent, detection at 350 nm): TR 5.65 min (retinyl oleate); TR 2.32 min (retinyl acetate); TR 2.08 min (retinol).

Reference： [1]Patent: US7566795,2009,B2 .Location in patent: Page/Page column 11-12

44
[ 112-80-1 ]
[ 2553-17-5 ]

Reference： [1]Bioscience, Biotechnology and Biochemistry,2009,vol. 73,p. 1118 - 1122
[2]Synthetic Communications,2014,vol. 44,p. 1149 - 1154
[3]Journal of the American Society for Mass Spectrometry,2018,vol. 29,p. 481 - 489

45
[ 112-80-1 ]
[ 7768-28-7 ]
[ 1037077-56-7 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2008,vol. 56,p. 5083 - 5090

Yield	Reaction Conditions	Operation in experiment
		Vegetable fatty acid (362.3 g) and the reaction product of ethylene diamine with 6 moles ethylene oxide (alkanolamine, 129.5 g) were mixed in a reaction flask equipped with a stirrer, a temperature probe and an inlet for an inert gas. 50% by weight hypophosphorous acid (0.8 g) was then added with stirring. The mixture was heated to 170 C, under a constant stream of nitrogen gas, and this temperature was maintained whilst the esterification water was distilled and until the acid value of the mixture was below 5 mg KOH/g. The mixture was then cooled to 70 C and dipropylene glycol (25.4 g) added. The temperature was adjusted to 60 C and dimethyl sulphate (65.3 g) added slowly over 6 hours, keeping the temperature between 60 and 65 C. Finally the mixture was cooled to 50 C and dipropylene glycol (25.4 g) added. The yield of finished softener concentrate was 600.0 g.

47
[ 112-80-1 ]
[ 7705-08-0 ]
[ 143-19-1 ]
[ 1120-45-2 ]

Reference： [1]Journal of Alloys and Compounds,2010,vol. 503,p. L31-L33

48
[ 112-80-1 ]
[ 136236-51-6 ]
[ 1260684-14-7 ]

Yield	Reaction Conditions	Operation in experiment
94%	In di-isopropyl ether; for 1.5h;Inert atmosphere;Product distribution / selectivity;	To a solution of 4.5 g (26.3 mmol) <strong>[136236-51-6]rasagiline</strong> in 120 ml diisopropyl ether 8.3 ml (26.3 mmol, 1.0 eq) oleic acid was added under nitrogen. After stirring for 90 min, the solvent was removed in vacuo at 300C. Drying on the rotary evaporator was continued for another 2 h at this temperature. Drying in high vacuum for 2 h yielded 11.2 g (24.7 mmol, 94 %) of a yellow oil.1H NMR (de-DMSO, 300 MHz): delta = 7.31 (m, 1 H, PhH), 7.21-7.10 (m, 3 H, PhH), 5.30 (t, J = 4.8 Hz, 2 H, olefin-H), 4.25 (t, J = 6.3 Hz, 1 H, N-CH), 3.37 (d, J = 2.8 Hz, 2 H, N-CH2), 3.04 (t, J = 2.4 Hz, 1 H, alkynyl-H), 2.90 (m, 1 H, ring-CH), 2.71 (quint, J = 15.0, 7.5 Hz, 1 H, ring-CH), 2.26 (m, 1 H, ring-CH), 2.15 (t, J = 7.5 Hz, 2 H, C(O)CH2), 1.97 (m, 4 H, 2 x C=CHCH2), 1.76 (m, 1 H, ring-CH), 1.48 (brt, J = 7.2 Hz, 2 H, C(O)CH2CH2), 1.25-1.21 (s, 18 H, 9 x CH2), 0.84 (t, J = 6.3 Hz, 3 H, omega-CH3). The integrals show a ratio of amine/acid = 1 :1.IR: v = 2925.56, 2854.04, 1712.92, 1615.04, 1551.28, 1459.31 , 1402.52 cm"1. IR indicates protonation of the amine.HPLC (by area%): 99.80 %.

Reference： [1]Patent: WO2011/3938,2011,A1 .Location in patent: Page/Page column 14-15

49
[ 112-80-1 ]
[ 123-99-9 ]
[ 124-19-6 ]
[ 112-05-0 ]
[ 2553-17-5 ]

Reference： [1]Catalysis Today,2011,vol. 161,p. 202 - 208

50
[ 112-80-1 ]
[ 623-57-4 ]
[ 1352945-51-7 ]

Reference： [1]Chemical Communications,2011,vol. 47,p. 12613 - 12615

51
[ 112-80-1 ]
[ 137618-48-5 ]
C₄₄H₈₁NO₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33.3%		General procedure: To the solution of oleic acid (3.75 g, 13.2 mmol) and 4-dimethylaminopyridine(DMAP) (270 mg) in CH2Cl2 at 0 C,N,N0-Dicyclohexylcarbodiimide (DCC) (2.75 g, 13.3 mmol) inCH2Cl2 were added dropwise. After 30 min, compound 3a (or 5a,or 6a) (11 mmol) was added, then the mixture was left for stirringat room temperature overnight. The reacting solution was cooledto 0 C, and the formed precipitate was filtered off. The filtratewas evaporated to give the residue, which was purified by silicagel column chromatography (PE/EA = 3/1, v/v) to give compound3b (or 5b, 6b).
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 24h;Inert atmosphere;	Oleic acid (10mmol) was dissolved in 20ml of 12 dichloromethane, then 13 N-Boc-3-amino-glycerine (3.3mmol), 14 EDC (3mmol) and 15 DMAP (3mmol) were added. The reaction mixture was stirred at room temperature for 24h under nitrogen. After reaction, the obtained 16 Boc protected 1,2-dioleoyl-3-amino-propane (DOAP) was isolated and purified by silica column chromatography (petroleum ether/ethyl acetate 20:1).

Reference： [1]Chemistry and Physics of Lipids,2012,vol. 165,p. 809 - 817
[2]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 5756 - 5763
[3]Journal of Controlled Release,2018,vol. 279,p. 53 - 68
[4]Patent: US10426745,2019,B2 .Location in patent: Page/Page column 35; 36

52
[ 112-80-1 ]
[ 103898-11-9 ]
[ 1346225-18-0 ]

Yield	Reaction Conditions	Operation in experiment
68.0%		General procedure: To the solution of oleic acid (3.75 g, 13.2 mmol) and 4-dimethylaminopyridine(DMAP) (270 mg) in CH2Cl2 at 0 C,N,N0-Dicyclohexylcarbodiimide (DCC) (2.75 g, 13.3 mmol) inCH2Cl2 were added dropwise. After 30 min, compound 3a (or 5a,or 6a) (11 mmol) was added, then the mixture was left for stirringat room temperature overnight. The reacting solution was cooledto 0 C, and the formed precipitate was filtered off. The filtratewas evaporated to give the residue, which was purified by silicagel column chromatography (PE/EA = 3/1, v/v) to give compound3b (or 5b, 6b).
58.7%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃;	[Example 73] N,N-bis(2-((Z)-0ctadec-9-enoyloxy)ethyl)amine (compound 73) tert-Butyl bis(2-hydroxyethyl)carbamate (Aldrich; 600 mg, 2.92 mmol) was dissolved in dichloromethane (30 mL), and stirred overnight at room temperature after adding oleic acid (Tokyo Chemical Industry Co., Ltd.; 1. 82 g, 6.43 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride(1.29 g, 6.72 mmol), and 4-dimethylaminopyridine (89 mg, 0.731 mmol). The aqueous layer was extracted with ethyl acetate after adding a saturated sodium bicarbonate aqueous solution to the reaction mixture. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure after filtration. The resulting residue was purified by silica gel column chromatography (hexane/chloroform = 50/50 to 0/100) to give tert-butyl N,N-bis(2-((Z)-octadec-9-enoyloxy)ethyl)carbamate (1.26 g, 58.7%).
58.7%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃;	tert-Butyl bis(2-hydroxyethyl)carbamate (Aldrich; 600 mg, 2.92 mmol) was dissolved in dichloromethane (30 mL), and stirred overnight at room temperature after adding oleic acid (Tokyo Chemical Industry Co., Ltd.; 1.82 g, 6.43 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.29 g, 6.72 mmol), and 4-dimethylaminopyridine (89 mg, 0.731 mmol). The aqueous layer was extracted with ethyl acetate after adding a saturated sodium bicarbonate aqueous solution to the reaction mixture. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure after filtration. The resulting residue was purified by silica gel column chromatography (hexane/chloroform=50/50 to 0/100) to give tert-butyl N,N-bis(2-((Z)-octadec-9-enoyloxy)ethyl)carbamate (1.26 g, 58.7%).

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 5756 - 5763
[2]Patent: EP2567951,2013,A1 .Location in patent: Paragraph 0245
[3]Patent: US2013/280305,2013,A1 .Location in patent: Paragraph 0481

53
[ 112-80-1 ]
[ 112-05-0 ]
[ 3788-56-5 ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 2534 - 2537
Angew. Chem.,2013,vol. 125,p. 2594 - 2597,4

54
[ 112-80-1 ]
[ 1477-68-5 ]
3'-O-methyl-N-oleoyl-dopamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With triethanolamine; benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphonium hexafluorophosphate; In tetrahydrofuran; at 20℃; for 15.25h;	Example V Synthesis of 3'-O-methyl-N-oleoyl-dopamine (Method I) 0.462 g (2.27 mmol) of 3-O-methyldopamine hydrochloride, 0.641 g (2.27 mmol) of oleic acid, 1.000 g (2.27 mmol) of BOP (Benzotriazol-1-yloxytris(dimethylamino)-phosphonium hexafluorophosphate) and 20 ml of THF were introduced into a flask. The reaction mixture was cooled down to a temperature of 0-5 C. and 0.949 ml (6.810 mmol) of triethanolamine in 4 ml THF were added drop-wise within 15 min and the reaction mixture was continuously stirred for 15 hours at room temperature. After evaporating the solvent, 100 ml of diethyl ether were added and the ether phase was washed three times with 30 ml of a 4% HCl solution, two times with 30 ml of a saturated NaHCO3 solution and two times with a saturated NaCl solution. After drying over anhydrous MgSO4 and removal of the solvent, the crude product was purified by crystallization from diethyl ether/hexane. 0.90 g (2.09 mmol) of the amide in the form of a white solid was obtained giving the reaction yield of 92%. Melting point: 78-79 C. NMR: 1H NMR: d 6.80 (d, J=7.5 Hz, 1H-5'), 6.69-6.65 (m, 2H-2', 6'), 5.70 (s, 1H-NH), 5.50 (s, 1H-OH), 5.38-5.30 (m, 2H-9.10), 3.87 (s, 3H-OCH3), 3.48 (q, J=6.0 Hz, 2H-1"), 2.74 (t, J=7.0 Hz, 2H-2"), 2.12 (t, J=8.0 Hz, 2H-2), 2.02-1.98 (m, 4H-8, 11), 1.60-1.57 (m, 2H-3), 1.32-1.26 (m, 20H-4, 5, 6, 7, 12, 13, 14, 15, 16, 17), 0.88 (t, J=7.0 Hz, 3H-18). 13C NMR: d 173.17, 146.67, 144.29, 130.67, 130.01, 129.74, 121.31, 114.42, 111.16, 55.89, 40.69, 36.87, 35.39, 31.91, 29.77, 29.72, 29.53, 29.33, 29.28, 29.27, 29.14, 27.23, 27.18, 25.78, 22.69, 14.13; Mass spectrometry: m/z=432.6 [M+H]+, 454.6 [M+Na]+;

Reference： [1]Patent: US2013/131361,2013,A1 .Location in patent: Paragraph 0050; 0051; 0052

55
[ 112-80-1 ]
[ 97004-04-1 ]
[ 1450603-52-7 ]

Yield	Reaction Conditions	Operation in experiment
36%		General procedure: To a solution of palmitic acid (300mg, 1.17mmol) in dichloromethane (DCM, 10mL) was added 1,1?-carbonyldiimdazole (209mg, 1.29mmol). The reaction was stirred at room temperature for 2h. The reaction mixture was slowly added to a solution of benzylamine (153muL, 1.40mmol) and 4-dimethylaminopyridine (14mg, 0.12mmol) in dichloromethane (5mL). The solution was stirred at room temperature for 18h. DCM (100mL) and saturated aqueous NaHCO3 (30mL) were added to the reaction mixture. The organic layer was separated and washed with H2O (30mL), brine (30mL), dried over anhyd sodium sulfate, filtered, and concentrated to dryness under reduced pressure. The crude was purified by flash chromatography on silica gel eluting with hexane/EtOAc (3:1, v/v) to give the title compound as a white solid (578mg, 86percent). Mp 85?87° [lit.45 mp 94.5?95°, and46 fp 95.1°]; 1H NMR (400MHz, CDCl3) delta 7.32?7.36 (m, 2H), 7.26?7.30 (m, 3H), 5.72 (br s, 1H), 4.45 (d, J=6.0Hz, 2H), 2.21 (t, J=7.2Hz, 2H), 1.61?1.67 (m, 2H), 1.25?1.34 (m, 24H), 0.88 (t, J=6.8Hz, 3H); 13C NMR (CDCl3, 100MHz) delta 173.21, 138.66, 128.92, 128.05, 127.71, 43.80, 37.06, 32.16, 29.92, 29.89, 29.84, 29.73, 29.59, 29.56, 26.01, 22.93, 14.36; LCMS, C23H39NO, [M+H]: 346.

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 5188 - 5197

56
[ 112-80-1 ]
[ 1453-93-6 ]
(Z)-Octadec-9-enoic acid (3S,5R,6S,8R,9R,10R,12R,13R,14R,17S)-6,12-dihydroxy-17-((S)-1-hydroxy-1,5-dimethyl-hex-4-enyl)-4,4,8,10,14-pentamethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester [ No CAS ]
[ 1443292-69-0 ]

Yield	Reaction Conditions	Operation in experiment
20%; 14%	With dmap; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 4 - 20℃; for 24.0h;	General procedure: PPT (500 mg) and different fatty acids (butyric acid, n-pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, capric acid, lauric acid, oleic acid, 8 mmol respectively) were dissolved in 25 mL dry tetrahydrofuran. N,N?-dicyclohexylcarbodiimide (DCC, 8 mmol) and 4-dimethylaminopyridine (DMAP, 0.8 mmol) were added while cooling on ice (4C). The mixture was stirred at room temperaturefor 24h, then was filtered, washed with CHCl3 three times and the filtrate combined. The filtrate was was evaporated to dryness under 80C to obtain the crude product. The crude product was subjected to silica gel column (3cm×40cm) chromatography, eluted with a gradient of petroleum and acetone (10:1-1.1) to obtain other compounds respectively.

Reference： [1]Letters in drug design and discovery,2013,vol. 10,p. 402 - 409

57
[ 122-32-7 ]
[ 112-80-1 ]
[ 4704-94-3 ]

Yield	Reaction Conditions	Operation in experiment
	With lipase from Pseudomonas stutzeri PS59; In aq. phosphate buffer; isopropyl alcohol; at 30℃; for 0.25h;pH 8.0;Enzymatic reaction;	General procedure: An assay mixture consisting of 1 ml of liquid ester or 1 g of solid ester, 3 ml of isopropanol, 5 ml of phosphate buffer (pH=8.0), and 1 ml of the lipase solution was incubated for 15 min at 30C with stirring at 180 rpm. The reaction was terminated by the addition of 95% ethanol, and the amount of liberated fatty acids after incubation was determined by titrating with 50 mM NaOH in the presence of two drops of phenolphthalein solution as the indicator. The control experiment was performed under the same conditions with the addition of 95% ethanol prior to the reaction. One unit of lipase activity was defined as the amount of enzyme required to liberate 1 mumol of free fatty acid per minute under the experimental conditions.

Reference： [1]Journal of Molecular Catalysis B: Enzymatic,2014,vol. 102,p. 16 - 24

58
[ 112-80-1 ]
[ 143-18-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; In methanol; at 65℃; for 0.000833333h;Industrial scale;	Prepare a solution of oleic acid in a container, The concentration is 0.4mol/L, the flow rate of the metering pump is set to 20ml/min; in another container, the methanol solution of potassium hydroxide is prepared at a concentration of 0.4mol/L. Set the flow rate of the metering pump to 20ml/min; start two metering pumps and enter the microchannel reactor or pipeline reactor at 65 degrees. The reaction was carried out for 3 seconds, and then passed through a 20-degree cooling pipe, cooled, and the product was filtered, dried, and the product purity was 99.9%, and the particle diameter D50 was 0.28 mum. Alternatively, after the above reaction, spray drying was carried out without cooling, and the obtained product had a purity of 99.3% and a particle diameter D50 of 91 nm.

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 1804 - 1808
[2]International Journal of Molecular Sciences,2019,vol. 20
[3]Patent: CN109503357,2019,A .Location in patent: Paragraph 0092; 0093; 0094; 0095
[4]Journal of the American Chemical Society,2020,vol. 142,p. 2956 - 2967

59
[ 112-80-1 ]
[ 544-76-3 ]
[ 629-78-7 ]
[ 123-01-3 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen; at 325℃; under 15001.5 Torr;Autoclave;	General procedure: Oleic acid (90%, Alfa-Aesar) was used as the unsaturated fattyacid. Pt/SAPO-11 was pre-activated in the oven for 3 h at 150C.The decarboxylation reactions were conducted in a 250 ml stainlesssteel, high pressure autoclave batch reactor (Parr model 4576A).Oleic acid and Pt/SAPO-11 were loaded into the reactor with a massratio of 18:1. Before the reaction started, the air in the reactor wasremoved by flushing with CO2or H2. The pressure was increased tothe desired reaction pressure (usually 20 bar). Under constant stir-ring conditions, the reactor was heated at a rate of 10C/min to thereaction temperature (200-325C) and this temperature was keptconstant during the reaction. Reaction of oleic acid with Pt-aluminawas carried out in a similar manner. After the reaction, the catalystparticles were separated, by filtration, from the liquid product andwashed with acetone for further characterizatio

Reference： [1]Journal of Molecular Catalysis A: Chemical,2014,vol. 386,p. 14 - 19

60
[ 112-80-1 ]
[ 629-62-9 ]
[ 544-76-3 ]
[ 629-78-7 ]
[ 123-01-3 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen; at 275℃; under 15001.5 Torr;Autoclave;	General procedure: Oleic acid (90%, Alfa-Aesar) was used as the unsaturated fattyacid. Pt/SAPO-11 was pre-activated in the oven for 3 h at 150C.The decarboxylation reactions were conducted in a 250 ml stainlesssteel, high pressure autoclave batch reactor (Parr model 4576A).Oleic acid and Pt/SAPO-11 were loaded into the reactor with a massratio of 18:1. Before the reaction started, the air in the reactor wasremoved by flushing with CO2or H2. The pressure was increased tothe desired reaction pressure (usually 20 bar). Under constant stir-ring conditions, the reactor was heated at a rate of 10C/min to thereaction temperature (200-325C) and this temperature was keptconstant during the reaction. Reaction of oleic acid with Pt-aluminawas carried out in a similar manner. After the reaction, the catalystparticles were separated, by filtration, from the liquid product andwashed with acetone for further characterizatio

Reference： [1]Journal of Molecular Catalysis A: Chemical,2014,vol. 386,p. 14 - 19

61
[ 112-80-1 ]
[ 112-40-3 ]
[ 544-76-3 ]
[ 629-78-7 ]
[ 123-01-3 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen; at 245℃; under 15001.5 Torr;Autoclave;	General procedure: Oleic acid (90%, Alfa-Aesar) was used as the unsaturated fattyacid. Pt/SAPO-11 was pre-activated in the oven for 3 h at 150C.The decarboxylation reactions were conducted in a 250 ml stainlesssteel, high pressure autoclave batch reactor (Parr model 4576A).Oleic acid and Pt/SAPO-11 were loaded into the reactor with a massratio of 18:1. Before the reaction started, the air in the reactor wasremoved by flushing with CO2or H2. The pressure was increased tothe desired reaction pressure (usually 20 bar). Under constant stir-ring conditions, the reactor was heated at a rate of 10C/min to thereaction temperature (200-325C) and this temperature was keptconstant during the reaction. Reaction of oleic acid with Pt-aluminawas carried out in a similar manner. After the reaction, the catalystparticles were separated, by filtration, from the liquid product andwashed with acetone for further characterizatio

Reference： [1]Journal of Molecular Catalysis A: Chemical,2014,vol. 386,p. 14 - 19

62
[ 112-80-1 ]
[ 3788-56-5 ]

Reference： [1]Synthetic Communications,2014,vol. 44,p. 1149 - 1154
[2]Synthetic Communications,2014,vol. 44,p. 1149 - 1154
[3]Advanced Synthesis and Catalysis,2016,vol. 358,p. 3084 - 3092
[4]Advanced Synthesis and Catalysis,2018,vol. 360,p. 696 - 703

63
[ 112-80-1 ]
[ 127-47-9 ]
[ 631-88-9 ]

Yield	Reaction Conditions	Operation in experiment
	With novozyme 435; In toluene; at 20℃; for 20h;Schlenk technique; Inert atmosphere; Enzymatic reaction;	General procedure: Retinyl esters were synthesized via an enzyme-catalyzed transesterification (19) as follows. Into a dry Schlenk flask, retinyl acetate (33 mg, 0.10 mmol), Novozyme 435 (120 mg), and AberlystA-21 (50 mg) were suspended in dry toluene (5 ml). The reaction mixture was stirred under an atmosphere of N2 , and five equivalents (0.50 mmol) of the appropriate acid (palmitic, stearic, linoleic, or oleic) were added. After 20 h at room temperature, the reaction mixture was filtered and the solvent was removed under reduced pressure to give a mixture (approximately 1:4) of the desired retinyl ester and unreacted acid. The resulting mixtures were used without further purification as LC/MS/MS standards for the corresponding retinyl esters.

Reference： [1]Journal of Lipid Research,2014,vol. 55,p. 319 - 328

64
[ 112-80-1 ]
[ 123-99-9 ]
[ 124-19-6 ]
[ 124-07-2 ]
[ 112-05-0 ]
[ 2553-17-5 ]

Reference： [1]Physical Chemistry Chemical Physics,2014,vol. 16,p. 13220 - 13228

65
[ 85721-33-1 ]
[ 112-80-1 ]
[ 638-68-6 ]
[ 3910-35-8 ]
heptyl octyl phthalate [ No CAS ]
3-methyl-2-propionylbenzoic acid [ No CAS ]
3-(2-hydroxy-2-methylpropyl)cyclohex-2-enone [ No CAS ]
[ 68-12-2 ]
[ 108-90-7 ]

Yield	Reaction Conditions	Operation in experiment
	With dipotassium peroxodisulfate; sulfuric acid; sodium hydroxide; In water; at 25℃; for 0.333333h;pH 5.0;UV-irradiation;Catalytic behavior; Kinetics;	The experimental set-up for the photocatalytic degradation ofCIP by immobilized TiO2nanoparticles on MMT is schematicallyFig. 2. Schematic representation of the reactor used for different processes.shown in Fig. 2. Photocatalysis of CIP was performed in a batchphotoreactor with a 500 mL working volume. A 16 W UV-A, UV-B or UV-C lamp (Sylvania, Japan) was applied as the light source.Batch studies were performed to evaluate the effect of CIP concen-tration, TiO2/MMT dose, the initial pH, UV light region, differentscavengers and enhancers on degradation efficiency. For each pho-tocatalytic experiment, 500 mL of an aqueous solution containingCIP in the range of 5-25 mg L-1with 0.025-0.150 g L-1of theTiO2/MMT nanocomposite was added in the reaction vessel. TheUV-A, UV-B or UV-C lamp was turned on at the beginning of eachexperiment. The pH of the solution was set to the desired valuewith H2SO4and NaOH (1 M). The solution pH was regulated witha Mettler Toledo pH meter (China). 5 mL samples were taken fromthe reactor at different intervals and residuals concentration of CIPwas measured using Varian Cary 100 UV-vis spectrophotometer(Australia) at the maximum wavelength of 276 nm. Degradationefficiency (%) = [(C0-Ct)/C0] × 100 was used to determine the degra-dation of CIP, where C0was the initial concentration of CIP solutionand Ctwas its concentration after a certain time (t). Adsorptionexperiments were conducted using the method applied for photo-catalytic degradation experiment without UV radiation. The zeropoint of charge (pHzpc) of the TiO2/MMT nanocomposite was mea-sured using the method described by Bessekhouad et al. with somemodifications [28]. In this approach, 500 mL 0.01 M NaCl was pre-pared and divided into five solutions with the pH ranging from 3to 10. A two hundred milligram catalyst was added to each solu-tion. Finally, the final pH of each solution was measured after 48 hshaking and plotted against the initial pH to determine the pHzpcof the catalyst. Electrophoretic mobility and the surface charge ofthe samples were carried out with the relation of the zeta poten-tial measurements. Zeta potentials of the samples were measuredusing a Zeta Meter 3.0+ (Zeta-Meter, Inc., USA). The zeta potentialof pure MMT, TiO2and TiO2/MMT was obtained to be -30.7, +21.06and -16.4 mV, respectively.

Reference： [1]Journal of Molecular Catalysis A: Chemical,2015,vol. 409,p. 149 - 161

66
[ 112-80-1 ]
[ 125414-41-7 ]
C₄₄H₈₁NO₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59.7%		General procedure: To the solution of oleic acid (3.75 g, 13.2 mmol) and 4-dimethylaminopyridine(DMAP) (270 mg) in CH2Cl2 at 0 C,N,N0-Dicyclohexylcarbodiimide (DCC) (2.75 g, 13.3 mmol) inCH2Cl2 were added dropwise. After 30 min, compound 3a (or 5a,or 6a) (11 mmol) was added, then the mixture was left for stirringat room temperature overnight. The reacting solution was cooledto 0 C, and the formed precipitate was filtered off. The filtratewas evaporated to give the residue, which was purified by silicagel column chromatography (PE/EA = 3/1, v/v) to give compound3b (or 5b, 6b).

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 5756 - 5763

67
[ 112-90-3 ]
[ 112-80-1 ]
[ 125238-99-5 ]
[ 207857-15-6 ]
N-(4-guanidino-1-oxo-1-(octadecylamino)butan-2-yl)octadec-9-enamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3.2 g		Example 20 Preparation of C18(oleic)-norArg-C18 N-(4-guanidino-1-oxo-1-(octadecylamino)butan-2-yl)octadec-9-enamide (0607) Fmoc-Dab(Boc)-resin. To 5 g of 2-chlorotrityl chloride resin with 1.3 mmol/g substitution (Novabiochem, 01-64-0114) in 50 ml of dry DCM in 60 ml reaction vessel for solid phase synthesis, 5.726 g (13 mmol, 2 eq) of Fmoc-Dab(Boc)-OH (Mw=440.5, (Fmoc-(N-gamma-Boc)-L-alpha,gamma-diaminobutyric acid, AnaSpec, 28246) and 2.26 ml (13 mmol, 2.0 eq) of DIPEA (Aldrich, Mw=129.2, d=0.74) were added. (0608) Dab(Boc)-resin. After 3 hrs the resin was washed 3× with DCM/MeOH/DIPEA (17:2:1), 3×DCM, 2×DMF, 3×DCM and Fmoc group was deprotected with 50 ml of 20percent piperidine/DMF twice for 15 min. (0609) C18:1-Dab(Boc)-resin. After Fmoc deprotection the resin was washed with 3×DCM, 2×MeOH and 3×DCM and for the coupling reaction 3.7 g (13 mmol) of oleic acid (Sigma, Mw=282.47, d=0.891), 5.37 g (13 mmol) of HCTU (Mw=413.7) and 2.62 ml (13 mmol) of DIPEA (Mw=129.2, d=0.74) in 50 ml of DMF were added. (0610) After 1 hr of reaction the resin was washed with 3×DCM, 2×MeOH and 3×DCM and progress of reaction was checked by Kaiser test which was negative (no free amine groups present). (0611) C18:1-Dab(Boc)-OH (Mw=566.56) was cleaved from the resin by 1percent TFA/DCM (5×50 ml for 2 min was filtered to flask with 2 ml 10percent pyridine/MeOH) and solvent was evaporated. (0612) C18:1-Dab(Boc)-C18:1 (Mw=734.95). Second coupling was carried out in solution. To the oily residue from the previous reaction, 3.725 g (9.75 mmol) of oleyl amine (Sigma, Mw=267.49, 70percent), 4.033 g (9.75 mmol) of HCTU (Mw=413.7) and 1.69 ml (9.75 mmol) of DIPEA (Mw=129.2, d=0.74) in 50 ml of DMF were added. After 4 hr 100 ml of AcOEt was added and organic layer was washed in separatory funnel with 3×0.5 M HCl, 3×10percent NaCO3 and 3×NaCl. AcOEt layer was dried with anhydrous MgSO4 and evaporated. (0613) C18:1-Dab-C18 (Mw=635.9). To the oily residue from the previous reaction, 100 ml of 80percent TFA/DCM 2.5percent TIS was added and after 20 min solvent was evaporated. (0614) C18:1-norArg(diBoc)-C18:1 (Mw=874.13). The residue was dissolved in 50 ml of DCM and pH was adjusted to 9 with TEA. 2.348 g (6 mM, 1 eq) of 1,3-Di-Boc-2-(trifluoromethylsulfonyl)guanidine (Mw=391.36, Aldrich 15033) was added and after 4 hrs DCM was evaporated. (0615) C18:1-norArg-C18:1 (Mw=674.1) To the oily residue from the previous reaction 100 ml of 95percent TFA/DCM 2.5percent TIS was added and after 3 hrs solvent was evaporated. Crude product was purified on TELEDYNE Isco CombiFlash Rf instrument using 48 g normal phase silica gel column, 100percent DCM for 3 CV (column volume) and 0-20percent MeOH for 10 CV, detection 214 nm, flow 45 ml/min. DCM/MeOH was evaporated and residue was precipitated by 0.1M HCl. Yield: 3.2 g.

Reference： [1]Patent: US9339461,2016,B2 .Location in patent: Page/Page column 86-87

68
[ 112-80-1 ]
[ 169555-95-7 ]
C₂₆H₄₂N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 23 Preparation of C18oleic-[4-Pal]-C16 N-(1-oxo-3-(pyridin-4-yl)-1-(hexadecylamino)propan-2-yl)octadec-9-enamide (0630) Fmoc-4-Pal-resin. To 5 g of 2-chlorotrityl chloride resin with 1.3 mmol/g substitution (Novabiochem, 01-64-0114) in 50 ml of dry DCM in 50 ml reaction vessel for solid phase synthesis 3.787 g (9.75 mmol, 1.5 eq) of Fmoc-4-Pal-OH (Mw=388.42, Advanced ChemTech) and 1.7 ml (9.75 mmol, 1.5 eq) of DIPEA (Aldrich, Mw=129.2, d=0.74) were added. (0631) 4-Pal-resin. After 2 hrs the resin was washed 3× with DCM/MeOH/DIPEA (17:2:1), 3×DCM, 2×DMF, 3×DCM and Fmoc group was deprotected with 40 ml of 20% piperidine/DMF 2 times for 15 min. (0632) C18oleic-4-Pal-resin. After Fmoc deprotection the resin was washed with 3×DCM, 2×MeOH and 3×DCM and for the coupling reaction 3.7 g (13 mmol) of oleic acid (Sigma, Mw=282.47, d=0.891), 5.37 g (13 mmol) of HCTU (Mw=413.7) and 2.62 ml (13 mmol) of DIPEA (Mw=129.2, d=0.74) in 50 ml of DMF were added. (0633) After 2 hr of reaction the resin was washed with 3×DCM, 2×MeOH and 3×DCM and progress of reaction was checked by Kaiser test which was negative (no free amine groups present). (0634) C18oleic-4-Pal-OH (Mw=430.62) was cleaved from the resin by 1% TFA/DCM (5×50 ml for 2 min was filtered to flask with 2 ml 10% pyridine/MeOH) and solvent was evaporated. (0635) C18oleic-4-Pal-C16 (Mw=654.06). Second coupling was carried out in solution. To the oily residue from the previous reaction, 2.354 g (9.75 mmol) of C16-amine (Sigma, Mw=241.46), 4.033 g (9.75 mmol) of HCTU (Mw=413.7) and 1.69 ml (9.75 mmol) of DIPEA (Mw=129.2, d=0.74) in 50 ml of DMF were added. After 4 hr 100 ml of AcOEt was added and organic layer was washed in reparatory funnel with 3×0.5 M HCl, 3×10% NaCO3 and 3×NaCl. AcOEt layer was dried with anhydrous MgSO4 and evaporated. Crude product was purified on TELEDYNE Isco CombiFlash Rf instrument using 48 g normal phase silica gel column, 100% DCM for 3 CV (column volume) and 0-20% MeOH for 10 CV, detection 214 nm, flow 45 ml/min. DCM/MeOH was evaporated and residue was precipitated by 0.1M HCl. Yield: 0.75 g.

Reference： [1]Patent: US9339461,2016,B2 .Location in patent: Page/Page column 88-89

69
[ 112-80-1 ]
[ 126-58-9 ]
dipentaerythritol oleate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With titanium(IV) oxide; at 260℃; for 8h;Inert atmosphere;	Production of Titanium Dioxide by Sulfuric Acid Method Industrial Metatitanic Acid (H2TiO3), The metatitanic acid was dried at a temperature of 120 C for 12 hours, passed through a 200 mesh sieve, and the meta-titanic acid having a particle size of 200 mesh or less was immersed in a sulfuric acid solution having a concentration of 0.7 mol / L, 1.6 hours, filtered and dried at a temperature of 100 C for 10 hours, followed by pulverization and passed through a 200 mesh sieve to obtain meta-titanate having a particle size of 200 mesh or less and calcined at a temperature of 490 C for 3 hours in a muffle furnace To obtain a titanium source solid acid catalyst.25.4 g of dipentaerythritol, 197.7 g of oleic acid and 0.89 g of catalyst were charged to the reaction system and the temperature was raised to 260 C with stirring under nitrogen. After 8 hours of reaction, the filtrate was filtered and the filtrate was purified by short-range distillation to obtain dipentaerythritol oleate, The refining was carried out at a temperature of 10 Pa and a temperature of 170 C.The esterification rate of the reaction was 99%.

Reference： [1]Patent: CN103833549,2016,B .Location in patent: Paragraph 0026-0028

70
[ 112-80-1 ]
[ 111-84-2 ]
[ 124-18-5 ]
[ 1120-21-4 ]
[ 112-40-3 ]
[ 629-50-5 ]
[ 544-76-3 ]
[ 629-78-7 ]
[ 620-14-4 ]
[ 54105-66-7 ]
[ 100-41-4 ]
[ 1074-43-7 ]
[ 473-91-6 ]

Reference： [1]Green Chemistry,2017,vol. 19,p. 4157 - 4168

71
[ 112-80-1 ]
[ 162558-25-0 ]
[ 609820-09-9 ]

Yield	Reaction Conditions	Operation in experiment
		Boc-DAP(N,N-diMe)-OH was preactivated with 3-(Diethoxyphosphoryloxy)-1, 2, 3-benzotriazin-4(3H)-one (DEPBT) and 2 eq of DIPEA in THF/DCM solvent mixture for 10 minutes followed by addition of linoleyl amine and subsequent stirring for 30 minutes. Crude compound was purified twice by flash chromatography: 1) normal phase silica gel (DCM/MeOH gradient) and 2) amine capped silica gel (Hexane/AcOEt gradient). The pure monoalkylated intermediate was dissolved in 1M HCl/ethyl acetate solution and the Boc group was removed within one hour followed by removal of the solvent under reduced pressure. The second alkyl chain was attached by preactivating the free carboxyl group of linoleic acid with (1-Ethyl-3-(3-dimethyllaminopropyl)-carbodiimide hydrochloride) (EDC) and N-Hydroxybenzotriazole (HOBt) in a 1:1 mixture of DMF and DCM for 10 minutes followed by addition of monoalkylated diMeDAP dissolved in DCM (pH adjusted to 6 with DIPEA) and subsequent stirring for 30 minutes. Crude compound was purified by flash chromatography (Hexane/AcOEt gradient) and converted to hydrochloride salt by stirring with 1M HCl/AcOEt. Final product was lyophilized.

Reference： [1]Patent: US2017/216227,2017,A1 .Location in patent: Paragraph 0320

72
[ 112-90-3 ]
[ 112-80-1 ]
[ 125238-99-5 ]
[ 207857-15-6 ]
N-(4-guanidino-1-((Z)-octadec-9-en-1-ylamino)-1-oxobutan-2-yl)oleamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		C18:1-norArg-C18:1 was synthesized as follows. Fmoc-N gamma-Boc-L-2,3-diaminobutyric acid was dissolved in dichloromethane (DCM), 2eq of diisopropylethyl amine (DIPEA) and the resulting solution was added to 2-chlorotrityl choride resin. After one hour, the resin was washed with DCM and Fmoc group was removed by treatment with 20percent piperidine in DMF yielding the free alpha-amine. Oleic acid was preactivated with 2-(6-Chloro-1H-benzotriazole-1-yl)-1,1,3,3-tetramethylaminium hexafluorophosphate (HCTU) and 2 equivalents of DIPEA and added to the resin and the reaction was deemed complete by negative Kaiser test. The lipidated compound was cleaved from the resin by multiple treatments with 1percent trifluoroacetic acid (TFA) in dichloromethane followed by evaporation under reduced pressure yielding free carboxylate intermediate. The second alkyl chain was attached by preactivating the free carboxyl group with (1-Ethyl-3-(3-dimethyllaminopropyl)-carbodiimide hydrochloride) (EDC) and N-Hydroxybenzotriazole (HOBt) in a 1:1 mixture of DMF and DCM for 10 minutes followed by addition of oleyl amine in same solvent and subsequent stirring for 30 minutes. Crude compound was purified by flash chromatography (Hexane/AcOEt gradient). The pure dialkylated intermediate was dissolved in 1M HCl/ethyl acetate solution and the Boc group was removed within one hour followed by removal of the solvent under reduced pressure. The resulting white solid was taken up in DCM to which was added TEA facilitate dissolution followed by treatment with 1, 3 Di-Boc-2-(trifluoromethylsulfonyl) guanidine for one hour. Upon completion of the reaction DCM was washed with 2 M sodium bisulfate, saturated sodium bicarbonate and dried over MgSO4 and removed under reduced pressure. The resulting residue was dissolved in absolute ethanol and two Boc groups were removed by adding dissolved compound drop wise to 12N HCl. Final product precipitated during reaction and was crystallized from EtOH.

Reference： [1]Patent: US2017/216227,2017,A1 .Location in patent: Paragraph 0339

73
[ 112-80-1 ]
[ 418759-58-7 ]
4-acetyl-2-methoxy-5-nitrophenyl oleate [ No CAS ]

Reference： [1]Macromolecular Bioscience,2017,vol. 17

74
[ 112-80-1 ]
[ 123318-82-1 ]
3',5'-dioleoylclofarabine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 14021 - 14024

75
[ 112-80-1 ]
[ 13515-95-2 ]
bis-oleic acid lysine methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90.18%		(2) Oleic acid (7.6 g, 27.04 mmol) was dissolved in 60 mL of anhydrous dichloromethane.Add HOBT (3.82g, 28.32mmol),EDCI (5.44g, 28.32mmol)And DIEA (5.3g, 41.20mmol),Ar protection is stirred for one hour,Add L-lysine methyl ester hydrochloride (3.1 g, 13.31 mmol),Ar was stirred to react for 12 hours.Dry the solvent,Dissolved in 60 mL of ethyl acetate,Then use saturated sodium bicarbonate solution (60mL × 2),Saturated sodium dihydrogen phosphate solution (60mL × 2),Wash with saturated sodium chloride solution (60 mL),Dry over anhydrous magnesium sulfate for one hour.8.27 g of a pale yellow solid concentrated under reduced pressure.The yield was 90.18%.
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 24.5h;Inert atmosphere; Cooling with ice;	Weigh accurately 5.0 g of H-Lys-OMe · 2HCl, 16.5 g of EDC · HCl and 6.4 g of HOBT in a 250 mL round-bottomed flask with a tube, evacuated, Charge nitrogen and add 30 mL of DCM to dissolve. Then 15.7 mL of oleic acid was added, Add 35.4 mL of DIEA for 0.5 h under ice bath, Then reacted at room temperature for 24 h. Oil pump to remove the solvent by rotary evaporation, The chloroform was dissolved, washed successively with 1 M HCl, saturated NaHCO3 and NaCl, After drying over anhydrous MgSO4 overnight, filtration, solvent removal, Separation on 200 - 300 mesh silica gel column chromatography (eluent DCM / MeOH = 10: 1) gave the white solid Oleic acid-Lys-OMe (compound 9).

Reference： [1]Patent: CN105056251,2018,B .Location in patent: Paragraph 0090; 0093; 0094
[2]Patent: CN104906076,2017,B .Location in patent: Paragraph 0093

76
[ 112-80-1 ]
[ 201230-82-2 ]
[ 6250-70-0 ]

Reference： [1]ACS Catalysis,2016,vol. 6,p. 8229 - 8238

77
[ 112-80-1 ]
[ 29110-74-5 ]
C₂₄H₃₇ClN₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With copper(I) thiophene-2-carboxylate; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(5-methyl-2-(4-fluorophenyl)pyridine(-1H))-iridium(III) hexafluorophosphate; N,N,N?,N?-tetramethyl-N?-tert-butylguanidine; bathophenanthroline; iodomesitylene diacetate; In 1,4-dioxane; at 20℃; for 1h;Inert atmosphere; Irradiation;	General procedure: To a 20 ml or 40 ml viale quipped with a stir bar was added photocatalyst, nitrogen nucleophile, iodomesitylene dicarboxylate, copper salt, and ligand. Dioxane was added followed by addition of the base. The solution was sonicated for 1-3 min until it became homogeneous. Next, the solution was degassed by sparging with nitrogen for 5-10 min before sealing with Parafilm. The reaction was stirred and irradiated using two 34-W blue LED lamps (3 cm away, with cooling fan to keep the reaction at room temperature) for 1 h. The reaction mixture was removed from the light, cooled to ambient temperature, diluted with water (15 ml) and ethyl acetate (25 ml), and the aqueous layer was extracted with ethyl acetate (3 × 25 ml). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel to afford the desired decarboxylative C-N coupling product. For aniline substrates, a solution of these nitrogen nucleophiles in dioxane was used; additionally, if the iodomesitylene dicarboxylate is a liquid, its solution in dioxane was used.

Reference： [1]Nature,2018,vol. 559,p. 83 - 88

78
[ 112-80-1 ]
[ 5438-70-0 ]
ethyl 2-(4-oleamidophenyl)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 40℃; for 8h;	The condensation reaction of oleic acid with H2N-R0 or OH-R0 gives the target compound: oleic acid (0.564 g, at room temperature)2.0 mmol), ethyl 4-aminophenylacetate (0.432 g, 2.4 mmol) and triethylamine (0.303 g, 3.0 mmol, 0.4 mL)In a 25 mL round bottom flask, two drops of catalyst DMAP were added dropwise to the above mixture, and 10 mL of solvent CH 2 Cl 2 (water removal) was added to dissolve.The mixed solution was prepared; another condensing agent EDC·HCl (0.576 g, 3.0 mmol) was dissolved in 4 mL of solvent CH 2 Cl 2 to prepare a condensing agent.a solution, and a condensing agent solution is dropwise added to the above mixed solution, and refluxed at 40 C for 8 hours; after the reaction is completed, the reaction solution is used.Wash with 1M HCl to pH 3, extract with dichloromethane (3×15 mL), and then rinse the organic phase with saturated sodium hydrogen carbonateWash the mixture twice with saturated brine, dry the organic phase with anhydrous sodium sulfate, filter and concentrate to give the crude product;The n-hexane-ethyl acetate mixture with a ratio of 10:1 was purified on a silica gel column to obtain 0.727 g of a white solid, which was targeted.Compound, yield: 82%

Reference： [1]Patent: CN105017096,2017,B .Location in patent: Paragraph 0071; 0072

79
[ 6318-23-6 ]
[ 112-80-1 ]
oleoyl β-D-1-galactopyranose amide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2018,vol. 140,p. 17356 - 17360

80
[ 115-77-5 ]
[ 1070-34-4 ]
[ 112-80-1 ]
C₆₅H₁₁₆O₁₀ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%		In the reactor, 68.1g (0.5mol) of pentaerythritol, 423.8g (1.5mol) of oleic acid were added successively, and a catalyst was added, and a water agent was added to control the oil bath heating temperature of 130-135 C. Under nitrogen protection, the mixture was stirred and refluxed, and water was separated. After 3.0 to 4.0 hours, it was slightly cooled, and 80.4 g of monoethyl succinate (0.55 mol) was added thereto, and the temperature was raised to 130-135 C, and the reaction was stirred for 2 hours. After the reaction was completed, the mixture was cooled to room temperature, washed with water, and the organic layer was evaporated in vacuo to give a pale-yellow oily liquid. The acid value was 0.08 mg KOH/g, yield 99%.

Reference： [1]Patent: CN109053441,2018,A .Location in patent: Paragraph 0017

81
[ 64-17-5 ]
[ 112-80-1 ]
[ 112-92-5 ]
[ 111-62-6 ]
[ 111-61-5 ]

Reference： [1]Green Chemistry,2019,vol. 21,p. 314 - 320

82
[ 112-80-1 ]
[ 63069-50-1 ]
C₂₅H₃₇FN₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%		Specifically, oxalyl chloride (0.71 mL, 8.24 mmol) was added over 10 min to a solution of oleic acid (2 mL, 6.34 mmol) and DMF (3 drops) in DCM (10 mL) at 0 C, and the solution stirred at room temperature overnight. The solvent and excess oxalyl chloride was removed in vacuo and the residue redissolved in DCM (10 mL). This solution was added dropwise to a solution of <strong>[63069-50-1]3-fluoro-4-aminobenzonitrile</strong> (0.70 g, 5.14 mmol) in DCM (10 mL) and ET.3N (1 mL) that had been cooled in an ice bath. Upon complete addition, the solution was stirred at room temperature overnight. The solution was washed with saturated Na2C03 solution (3 chi 20 mL), H2O (20 mL), and brine (20 mL), and dried over MgS04. The resulting residue was subjected to column chromatography, using a gradient elution of EtOAc/petroleum spirits to afford the product as a white. (0541) [00403] Yield: 1 .59 a (61 %). [00404] FT-I (ATR) V^/crrr1 : 3319 br w. 2919 m. 2850 m. 2236 w. 1681 s. 1616 w. 1589 m, 1519 s. 1 H-NMR delta/ppm (d6-DMSO): 10.07 (1 H, s, NH), 8.33 (1 H, dd, 3JH,H = 8.5 Hz, 4 H,F = 7.9 Hz, Ar CH), 7.89 (1 H, dd, 3JH,F = 1 1 .0 Hz, 4 H,H = 2.0 Hz, Ar CH), 7.66 (1 H, ddd, 3JH,H = 8.5 Hz, 4JH,H = 2.0 Hz, 5JH,F = 0.9 Hz, Ar CH), 5.29 - 5.40 (2 chi 1 H, 2 chi m, 2 chi olefinic CH), 2.47 (2H, m, NHCOCH2) , 1 .96 - 2.04 (2 x 2H, 2 x m, 2 x CH2), 1 .61 (2H, m, CH2), 1 .23 - 1 .37 (10 chi 2H, 10 chi m, 10 chi CH2), 0.87 (3H, m, CH3). 13C-NMR delta/ppm (d6-DMSO): 172.4 (CONH), 151 .6 (d, 1 JC,F = 247 Hz, Ar CF), 131 .7 (d, 2JC,F = 1 1 .1 Hz, Ar C), 129.6 (olefinic CH), 129.5 (olefinic CH), 129.3 (d, 3JC,F = 3.4 Hz, Ar CH), 122.9 (d, 4JC,F = 2.7 Hz, Ar CH), 1 19.2 (d, 2JC,F = 23.3 Hz, Ar CH), 1 17.9 (d, 4JC,F = 2.7 Hz, CN), 105.7 (d, 3JC,F = 9.4 Hz, Ar C), 35.9 (NHCOCH2), 31 .3 (CH2) , 29.09 (CH2), 29.08 (CH2), 28.8 (CH2), 28.7 (CH2), 28.62 (CH2), 28.59 (CH2), 28.55 (CH2), 28.5 (CH2), 26.6 (CH2), 24.9 (CH2), 22.1 (CH2), 13.9 (CH3).

Reference： [1]Patent: WO2019/40992,2019,A1 .Location in patent: Paragraph 00401-00404

83
[ 112-80-1 ]
[ 77087-60-6 ]
methyl (2S)-3-(tert-butoxycarbonylamino)-2-[[(Z)-octadec-9-enoyl]amino]propanoate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 2466 - 2484

84
[ 112-80-1 ]
[ 91-20-3 ]
[ 187737-37-7 ]
[ 7373-13-9 ]
[ 74-85-1 ]
[ 112-61-8 ]
[ 95-47-6 ]
[ 611-14-3 ]
[ 106-42-3 ]
[ 100-41-4 ]
[ 62185-21-1 ]
[ 90-12-0 ]
[ 108-88-3 ]

Yield	Reaction Conditions	Operation in experiment
	With mesoporous ZSM-5 zeolite with pore size of about 16nm; at 550℃;Catalytic behavior;	General procedure: Catalytic performance of catalysts was evaluated by catalytic cracking of ethanol and oleic acid in a fixed-bed quartz tube reactor(inner diameter: 20 mm; length: 380 mm). As a typical run, the catalyst(0.5 g) was loaded into reactor, and heated to a desired temperature inN2 stream (the flow rate: 40 mL/min). The feedstock (0.87 g) was then injected into the reactor by a syringe pump. After flowing out from the reactor, the reaction products were cooled. Liquid products were weighed and analyzed by GC-MS (QP5000, Shimadzu, Japan) equipped with a DB-WAX fused silica capillary column (30m×0.25mm×0.25 mum). The gaseous product was collected with a gas collecting bag,and analyzed by GC referring to the method as described in our previous study

Reference： [1]Applied Catalysis A: General,2019,vol. 575,p. 101 - 110

85
[ 50584-68-4 ]
[ 112-80-1 ]
panthenyl monooleate [ No CAS ]

Reference： [1]Green Chemistry,2019,vol. 21,p. 3353 - 3361

86
[ 112-80-1 ]
[ 85342-65-0 ]
C₂₆H₃₃Cl₄NO₄ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 11398 - 11403

87
[ 112-80-1 ]
[ 27208-80-6 ]
polydatin-6''-O-yl oleate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68.5%	With Candida antarctica lipase B immobilized on resin beads; In acetone; at 50℃; for 96h;Enzymatic reaction;	General procedure: Synthesis was carried out following a previously reported method (Vaisali et al., 2017) with some modifications. Esterification of palmitic acid and <strong>[27208-80-6]polydatin</strong> was used to standardise reaction conditions for other fatty acids. Reactions were performed in a 30 mL hermetically sealed bottle consisting of previously dried <strong>[27208-80-6]polydatin</strong> (0.2 mmol, 78 mg), palmitic acid (0.8 mmol, 205 mg), 5 mL solvent and 75 mg Novozym 435. The reaction mixture was kept in an orbital shaker at constant agitation of 150 rpm and 50 C for 6 days. Samples were analysed using HPLC and LCMS.

Reference： [1]Food Chemistry,2019,vol. 301

88
[ 112-80-1 ]
[ 26348-61-8 ]
ethyl (S)-3-hydroxy-2-[(Z)-octadec-9-enamido]propanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20℃; for 4h;Inert atmosphere;	In a round bottom flask were introduced oleic acid (1 g, 3.54 mmol), dry THF (50 ml_), <strong>[26348-61-8]L-serine ethyl ester hydrochloride</strong> salt (600 mg, 3.54 mmol), (Benzotriazol-1- yloxy)tripyrrolidinophosphonium hexafluorophosphate (PyBOP) (2.03 g, 3.9 mmol) under inert atmosphere. The mixture was treated with /'Pr2NEt (1.36 ml_, 7.8 mmol) and stirred for 4h at room temperature. After removing solvent under vacuum, the residue was dissolved in EtOAc, successively treated by HCI 1 N, water, saturated aqueous NaHC03 and brine. The organic layer was dried over MgS0 and purified by column chromatography on Si02. (petroleum ether/ ethyl acetate (1 :3), Rf = 0.58). mpure = 1.13 g. Aspect: white solid. Yield: 80%. 1H NMR (500 MHz, DMSO) d (ppm): 8.01 (bd, 1 H, J = 7.6 Hz), 5.40 - 5.21 (m, 2H), 4.95 (t, 1 H, J = 5.7 Hz), 4.30 (dt, 1 H, J = 5.0 Hz, J = 7.9 Hz), 4.07 (q, 2H, J = 7.1 Hz), 3.63 (ddt, 2H, J = 5.3 Hz, J = 10.6 Hz, J = 33.3 Hz), 2.17 - 2.08 (m, 2H), 2.06 - 1.91 (m, 4H), 1.56 - 1.44 (m, 2H), 1.30 - 1.12 (m, 23H), 0.85 (t, 3H, J = 6.8 Hz). 13C {1 H} NMR (126 MHz, CDCI3) d (ppm): d 173.80, 170.55, 129.87, 129.59, 63.27, 63.13, 61.70, 54.59, 36.34, 31.78, 29.65, 29.61 , 29.40, 29.20 (2x), 29.17, 29.12, 29.04, 27.10, 27.07, 25.48, 22.56, 13.99. HRMS calcd for C23H44N04 [M+H]+: 398.3265; found: 398.3258.

Reference： [1]Patent: WO2019/228994,2019,A1 .Location in patent: Page/Page column 35-36

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Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 112-80-1 ] {[proInfo.proName]}

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[ 112-80-1 ] Synthesis Path-Upstream 1~13

[ 112-80-1 ] Synthesis Path-Downstream 1~88

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Carboxylic Acids

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[ 112-80-1 ]

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