[ CAS No. 476-66-4 ] {[proInfo.proName]}

Name: 476-66-4|2,3,7,8-Tetrahydroxychromeno[5,4,3-cde]chromene-5,10-dione|98%
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Quality Control of [ 476-66-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 476-66-4 ]

Product Details of [ 476-66-4 ]

CAS No. :	476-66-4	MDL No. :	MFCD00006914
Formula :	C₁₄H₆O₈	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AFSDNFLWKVMVRB-UHFFFAOYSA-N
M.W :	302.19	Pubchem ID :	5281855
Synonyms :	Gallogen;Elagostasine;HSDB 7574;CCRIS 774;Benzoaric acid;Alizarine Yellow;TBBD;Lagistase

Calculated chemistry of [ 476-66-4 ]

Physicochemical Properties

Num. heavy atoms :	22
Num. arom. heavy atoms :	16
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	8.0
Num. H-bond donors :	4.0
Molar Refractivity :	75.31
TPSA :	141.34 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.36 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.79
Log Po/w (XLOGP3) :	1.1
Log Po/w (WLOGP) :	1.31
Log Po/w (MLOGP) :	0.14
Log Po/w (SILICOS-IT) :	1.67
Consensus Log Po/w :	1.0

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	1.0
Egan :	1.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.94
Solubility :	0.343 mg/ml ; 0.00114 mol/l
Class :	Soluble
Log S (Ali) :	-3.66
Solubility :	0.066 mg/ml ; 0.000218 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.35
Solubility :	0.136 mg/ml ; 0.000449 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	1.0 alert
Brenk :	3.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	3.17

Safety of [ 476-66-4 ]

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

Application In Synthesis of [ 476-66-4 ]

* 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 [ 476-66-4 ]
Downstream synthetic route of [ 476-66-4 ]

[ 476-66-4 ] Synthesis Path-Upstream 1~2

1
[ 100227-56-3 ]
[ 476-66-4 ]
[ 23094-69-1 ]

Reference： [1] Phytochemistry, 2003, vol. 63, # 7, p. 817 - 823

2
[ 106647-18-1 ]
[ 476-66-4 ]
[ 23094-69-1 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1986, vol. 34, # 10, p. 4075 - 4082

[ 476-66-4 ] Synthesis Path-Downstream 1~15

1
[ 99-24-1 ]
[ 476-66-4 ]

Yield	Reaction Conditions	Operation in experiment
83%	With boron trifluoride diethyl etherate; bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at 20℃; for 24h; Inert atmosphere;	Ellagic acid (5) Method 1: To a solution of methyl gallate (15) (128 mg, 0.69 mmol) dissolved in methylene chloride (10 mL), was added PIFA (455 mg, 1.06 mmol) dissolved in boron trifluoride-diethyl etherate (1.5 mL). The reaction mixture was stirred at ambient temperature under nitrogen for 24 hours. Water (10 mL) was added to quench the reaction mixture. Extraction using n-butanol (4 10 mL), followed by purification via column chromatography (acetone-hexane 1:4), afforded the natural product 5 as a cream solid (87 mg, 83%).
78%	With dipotassium peroxodisulfate In acetic acid at 80℃; for 12h;	1 Example 1: Weigh 200 g of gallic acid methyl ester,Placed in the reaction flask, then added 600 mL of acetic acid,Stir and heat to 80 ° C to dissolve the methyl gallate,200 g of K2S2O8 was added, and the reaction was stirred under reflux for 12 h to stop the reaction.The reaction solution was cooled and crystallized, filtered, and the filter cake was washed with hot water at 80 °C.The filter cake was dissolved in a 10% NaOH solution, and 20 g of activated carbon was added thereto, and the mixture was decolorized by stirring at 25 ° C, filtered, and the filtrate was extracted three times with ethyl acetate, and the filtrate was separated.The aqueous phase was adjusted to pH 1.5 with 10% hydrochloric acid, crystallization, filtration, and vacuum drying to obtain pale yellow ellagic acid.The yield is 78% and the relative content is up to 95%.
	With iron(III) chloride; acetic acid

	With methanol; barium dihydroxide Reagens 4: Wasser; Durchleiten von Luft;
	With methanol; sodium hydrogencarbonate Reagens 4: Wasser; Durchleiten von Luft;
	Multi-step reaction with 2 steps 1: ammonium hydroxide / 12 h / 50 °C 2: 3-chloro-benzenecarboperoxoic acid / 10 h
0.74 g	Stage #1: methyl galloate With sodium hydrogencarbonate In water at 15 - 25℃; for 24h; Stage #2: With sodium tetraborate heptahydrate In water; acetonitrile at 80℃;	21; 22; 23; 24; 25; 26; 27; 29; 30; 31; 32; 33; 34; 35; 36; 37; 38 Example 21 Synthesis of Compound d-1 8.5 g of sodium hydrogencarbonate was dissolved in 200 ml of purified water,While performing air bubbling at a flow rate of 5 ml / min,A solution of 3.75 g of methyl gallate in 20 ml of methanol was added little by little,The reaction was carried out at an internal temperature of 15 to 25 ° C. for 24 hours.The green precipitate was filtered off, suspended for 1 hour with 200 ml of 5% aqueous sulfuric acid solution,Filtration, washing with water and drying under reduced pressure at 60 ° C. 2.69 g of a crude product of compound d-1 as a green solid target substance was obtained. The obtained crude product had a weight content of 75.4 wt% and a purity conversion yield of 66.0%.To 1.0 g of the obtained crude product, 25 ml of acetonitrile and 2.5 ml of purified water were added, and the mixture was stirred at an internal temperature of 20 ° C. for 30 minutes.Dust filtering was carried out to remove insoluble matter, and the obtained solution had pH 2. It was 0. To this solution, 20 ml of a 0.01 M aqueous solution of sodium tetraborate heptahydrate prepared in advance was added dropwise to adjust the pH to 6.0. Next, acetonitrile was distilled off under normal pressure at an internal temperature of about 80 ° C. After cooling to an internal temperature of 20 ° C., the mixture was stirred for 2 hours. Precipitated crystals were filtered, washed with 10 ml of purified water, and then dried at 60 ° C. under reduced pressure. 0.74 g of pale yellow crystals of the target compound d-1 was obtained. Weight content was 99.9 wt%, purity conversion yield was 64.6%
	Multi-step reaction with 5 steps 1: potassium iodide; potassium carbonate / acetone / Reflux 2: N-Bromosuccinimide / N,N-dimethyl-formamide / 20 °C 3: copper / N,N-dimethyl-formamide / Heating 4: palladium(II) hydroxide; hydrogen / ethyl acetate / 18 h 5: methanol; water / 4 h / 85 °C
	Multi-step reaction with 2 steps 1: [bis(acetoxy)iodo]benzene; boron trifluoride diethyl etherate / dichloromethane / 16 h / 20 °C / Inert atmosphere 2: water; methanol / 24 h / Reflux

Reference： [1]Daley, Sharna-Kay; Downer-Riley, Nadale [Beilstein Journal of Organic Chemistry, 2020, vol. 16, p. 2026 - 2031]
[2]Current Patent Assignee: GUIYANG BEILONG BIOTECHNOLOGY - CN110066284, 2019, A Location in patent: Paragraph 0051-0052
[3]Schwenk [Journal fur praktische Chemie (Leipzig 1954), 1914, vol. <2> 90, p. 57]
[4]Erdtman [Svensk Kemisk Tidskrift, 1935, vol. 47, p. 223,227]
[5]Erdtman [Svensk Kemisk Tidskrift, 1935, vol. 47, p. 223,227]
[6]Current Patent Assignee: GUIYANG BEILONG BIOTECHNOLOGY - CN108395440, 2018, A
[7]Current Patent Assignee: FUJIFILM HOLDINGS CORP. - JP2015/189756, 2015, A Location in patent: Paragraph 0067-0068; 0069-0072
[8]Chambers, Schuyler A.; Gaddy, Jennifer A.; Townsend, Steven D. [Chemistry - A European Journal, 2020, vol. 26, # 44, p. 9923 - 9928]
[9]Daley, Sharna-Kay; Downer-Riley, Nadale [Beilstein Journal of Organic Chemistry, 2020, vol. 16, p. 2026 - 2031]

2
[ 831-61-8 ]
[ 476-66-4 ]

Yield	Reaction Conditions	Operation in experiment
74%	With sodium persulfate In acetic acid at 80℃; for 12h;	2 Example 2: Weigh 200g of gallic acid ethyl ester,Placed in the reaction flask,Then add 5% CH3COOH 600mL,Stir and heat to 80 ° C to dissolve the methyl gallate,200 g of Na2S2O8 was added, and the reaction was stirred under reflux for 12 h to stop the reaction.The reaction solution was cooled and crystallized, filtered, and the filter cake was washed with hot water at 80 °C.The filter cake was dissolved in a 10% NaOH solution, and 20 g of activated carbon was charged.The mixture was decolorized by stirring at 25 ° C, filtered, and the filtrate was extracted three times with ethyl acetate.The filtrate was separated, and the aqueous phase was adjusted to pH 1.5 with 10% hydrochloric acid.Crystallization, filtration, vacuum drying to obtain pale yellow ellagic acid,The yield is 74% and the relative content is up to 93%.
	With sodium carbonate
	With ammonia; water durch Einleiten von Luft;

	With Marshall's acid
	Multi-step reaction with 2 steps 1: ammonium hydroxide / 12 h / 50 °C 2: 3-chloro-benzenecarboperoxoic acid / 10 h

Reference： [1]Current Patent Assignee: GUIYANG BEILONG BIOTECHNOLOGY - CN110066284, 2019, A Location in patent: Paragraph 0053-0054
[2]Ernst; Zwenger [Justus Liebigs Annalen der Chemie, 1871, vol. 159, p. 33] Schiff [Justus Liebigs Annalen der Chemie, 1872, vol. 163, p. 218][Chemische Berichte, 1879, vol. 12, p. 1533]
[3]Herzig; Pollak; v. Bronneck [Monatshefte fur Chemie, 1908, vol. 29, p. 278]
[4]Trivedi, K. K.; Kochak, Geeta; Misra, K. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 9, p. 925 - 926]
[5]Current Patent Assignee: GUIYANG BEILONG BIOTECHNOLOGY - CN108395440, 2018, A

3
[ 14937-32-7 ]
[ 476-66-4 ]

Reference： [1]Liebigs Annalen der Chemie,1984,p. 929 - 938
[2]Bioscience, Biotechnology and Biochemistry,2001,vol. 65,p. 1869 - 1871
[3]Phytochemical Analysis,2013,vol. 24,p. 424 - 435

4
[ 536-08-3 ]
[ 476-66-4 ]

Yield	Reaction Conditions	Operation in experiment
	With dihydrogen peroxide

Reference： [1]Nierenstein [Chemische Berichte, 1910, vol. 43, p. 628] Nierenstein; Spiers; Hatcher [Journal of the American Chemical Society, 1925, vol. 47, p. 847] Fischer,E.; Freudenberg [Chemische Berichte, 1913, vol. 46, p. 1126,1128]

5
[ 536-08-3 ]
[ 7722-84-1 ]
[ 476-66-4 ]

Reference： [1]Fischer,E.; Freudenberg [Chemische Berichte, 1913, vol. 46, p. 1126,1128] Nierenstein [Journal of the American Chemical Society, 1910, vol. 43, p. 630] Nierenstein [Journal of the American Chemical Society, 1925, vol. 47, p. 847]

6
[ 60976-49-0 ]
[ 476-66-4 ]

Reference： [1]Phytochemical Analysis,2013,vol. 24,p. 424 - 435

7
[ 5424-20-4 ]
[ 476-66-4 ]

Yield	Reaction Conditions	Operation in experiment
1.8 g	With sodium hydroxide at 85 - 90℃; for 1h; Sonication;	5 Example 5 Taking 13g turn jambolans tannin, adding 0.5mol/L sodium hydroxide solution of 390 ml, in 85-90 °C lower, ultrasonic power 500w, ultrasonic reaction time 60 min. The reaction liquid by adding dilute hydrochloric acid under stirring, until the pH value of the reaction liquid 5, filtering, the filter cake after the water washing, ellagic acid to obtain brown crude product, crude product purity is 69.6%. Crude product with embodiment 2 process is refined drying to obtain strawcoloured ellagic acid product 1.8g, content is 98.4%.; The ellagic acid is added to sodium hydroxide dilute solution of the crude product, by adding activated carbon, in the 50 °C reaction under the temperature 1 hour, filtering the reaction liquid, and for washing the filter cake, combined filtrate and wash liquid; adding dilute hydrochloric acid to pH of the solution is adjusted to pH value of 4, filtering, the filter cake is water-washing, and drying to obtain strawcoloured ellagic acid product 0.6g, content is 98.1%.

Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF FORESTRY - CN105524074, 2016, A Location in patent: Paragraph 005; 0026

8
C₄₂H₃₄O₂₈ [ No CAS ]
[ 149-91-7 ]
[ 476-66-4 ]
[ 23725-05-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; water for 12h; Reflux;	4.4. Acid hydrolysis of 13 and 14 A solution of 13 in 1N H2SO4 (2 mg in 10 ml) was heated under reflux for 12 h. After cooling, the resulting solution was neutralizedwith saturated aqueous Na2CO3 solution. The precipitates formed were collected by filtration and dissolved in MeOH. The product was identified as ellagic acid (43) by TLC comparison under UV light (254 nm) with an authentic sample on a silica gel TLC plate, and the plate was developed with a mobile phase of EtOAc-toluene-HCO2H (5: 5: 2.5, v/v, Rf 0.30). The filtrate was analyzed by analytical HPLC (solvent system: aqueous 0.1% HCO2H (A) and MeCN (B), gradient condition: 1%-10% B in 20 min, 1 ml/min) to detect chebulic acid (22, tR 7.6 min) and gallic acid (25, tR 14.0 min), which were identified by comparing the retention time with authentic samples. Parallel studies were carried out with 14 (Supplementary information, Fig. S12).

Reference： [1]Lee, Dong Young; Kim, Hyun Woo; Yang, Heejung; Sung, Sang Hyun [Phytochemistry, 2017, vol. 137, p. 109 - 116]

9
C₄₃H₃₆O₂₈ [ No CAS ]
[ 149-91-7 ]
[ 476-66-4 ]
[ 23725-05-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; water for 12h; Reflux;	4.4. Acid hydrolysis of 13 and 14 A solution of 13 in 1N H2SO4 (2 mg in 10 ml) was heated under reflux for 12 h. After cooling, the resulting solution was neutralizedwith saturated aqueous Na2CO3 solution. The precipitates formed were collected by filtration and dissolved in MeOH. The product was identified as ellagic acid (43) by TLC comparison under UV light (254 nm) with an authentic sample on a silica gel TLC plate, and the plate was developed with a mobile phase of EtOAc-toluene-HCO2H (5: 5: 2.5, v/v, Rf 0.30). The filtrate was analyzed by analytical HPLC (solvent system: aqueous 0.1% HCO2H (A) and MeCN (B), gradient condition: 1%-10% B in 20 min, 1 ml/min) to detect chebulic acid (22, tR 7.6 min) and gallic acid (25, tR 14.0 min), which were identified by comparing the retention time with authentic samples. Parallel studies were carried out with 14 (Supplementary information, Fig. S12).

Reference： [1]Lee, Dong Young; Kim, Hyun Woo; Yang, Heejung; Sung, Sang Hyun [Phytochemistry, 2017, vol. 137, p. 109 - 116]

10
[ CAS Unavailable ]
[ 476-66-4 ]

Yield	Reaction Conditions	Operation in experiment
89%	With sulfuric acid In water at 100℃;	2 Example 2 90% tannic acid 5 grams and 60% sulfuric acid aqueous solution dosage of 50 ml, placed in 100 ml volume of glass pressureThe reaction was carried out in a reactor at a flow rate of 50 mL / min, a pressure of 0.5 MPa, a reactor temperature of 100 ° C,Should end, with 50% aqueous solution of sodium hydroxide and then add ethyl acetate extraction; static separation, collecting organic layer, decompression concentratedThe concentration of the extract was analyzed by high performance liquid chromatography. The analysis conditions were the same as those of Example 1 and the yield was 89%

Reference： [1]Current Patent Assignee: GUIYANG DANNING SCI TECH - CN106279199, 2017, A Location in patent: Paragraph 0028; 0029; 0030; 0031; 0032; 0033; 0034; 0035

11
ellagic acid 3-O-α-L-rhamnopyranosyl-4′-O-α-L-arabinofuranoside [ No CAS ]
[ 5328-37-0 ]
[ 3615-41-6 ]
[ 476-66-4 ]

Yield	Reaction Conditions	Operation in experiment
77%	With hydrogenchloride; In 1,4-dioxane; at 80℃; for 1h;	General procedure: A solution of 1 or 2 (each 5.0mg) in 1M HCl-1,4-dioxiane(1:1, v/v, 1.0mL) was stirred at 80C for 1h.After cooling, the reaction mixture was neutralized withAmberlite IRA-400 (OH- form) and the resin was removedby filtration. After removal of the solvent from the filtrateunder reduced pressure, the residue was partitioned inEtOAc-H2O (1:1, v/v), and the solvents removed in vacuofrom the EtOAc-soluble fraction and an aqueous phase,respectively. The EtOAc-soluble fraction was purifiedby normal-phase silica gel CC [500mg, hexane-EtOAc(3:1, v/v)] to furnish 3-O-methylellagic acid (1a, 2.8mg,78%, from 1) [12] or ellagic acid (8, 2.0mg, 77% from 2)[12, 23, 25, 26]. In turn, the aqueous layer was subjectedto HPLC analysis under the following conditions: HPLC column, Kaseisorb LC NH2-60-5, 4.6mm i.d.×250mm(Tokyo Kasei Co., Ltd.); detection, optical rotation [ShodexOR-2 (Showa Denko Co., Ltd., Tokyo, Japan); mobilephase, CH3CN-H2O (85:15, v/v); flow rate 0.5mL/min]. Identification of L-rhamnose [tR: 12.0min (negative optical rotation)] from 2 and L-arabinose [tR: 16.2min (positive optical rotation)] from 1 and 2 in the H2O-elutedfraction was carried out by comparing the retention timeand optical rotation with those of authentic samples [1,13-21]. Through a similar procedure, 1a [3.0mg, 85%from 5 (5.0mg)], 3,3?-di-O-methylellagic acid [1c, 1.9mg,88% from 1b (3.0mg)] [12, 23], 4,3?-di-O-methylellagicacid [2b, 1.0mg, 88% from 2a (2.0mg)] [26], 4,3?,4?-tri-O-methylellagic acid [3b, 1.0mg, 73% from 3a (2.0mg)][23, 27], and 8 [2.9mg, 86% from 3 (5.0mg)] were purifiedfrom each EtOAc-soluble fraction by normal-phasesilica gel CC.

Reference： [1]Natural Medicines,2018,vol. 72,p. 317 - 325

12
[ 618-73-5 ]
[ 476-66-4 ]

Yield	Reaction Conditions	Operation in experiment
84%	With 3-chloro-benzenecarboperoxoic acid; for 10.0h;	Weigh 50g of gallic acid,Pour into a 500ml jar after drying,Then added 25% concentrated ammonia water 250ml,Plug the bottle with a stopper,Stir in a constant temperature water bath at 50 C for 12 h.The reaction solution was then poured into a 1000 ml dry three-necked flask.60 g of m-CPBA was charged and reacted for 10 hours.After the reaction is over,Filter the reaction solution,The filter cake was dissolved in 10% NaOH solution.Put in 250g of activated carbon,Stirring at 35 C,Filtration, the filtrate was extracted three times with dichloromethane, the filtrate was separated, and the filtrate was adjusted to pH 2 with 10% hydrochloric acid.Crystallization, filtration, and drying to obtain pale yellow ellagic acid.Its yield was 84%.

Reference： [1]Patent: CN108395440,2018,A .Location in patent: Paragraph 0018-0023

13
[ 476-66-4 ]
[ 2561417-30-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	Stage #1: ellagic acid With Dichlorodiphenylmethane at 180℃; for 3h; Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 5h;	Preparation oftetraol 7 A solution of ellagic acid (6, 2.6g, 8.6mmol) was treatedwith β,β-dichlorodiphenylmethane (13mL, 68.9mmol) at180°C for 3h. After cooling down to room temperature,the reaction mixture was diluted with n-hexane, then filtrated.The resulting residue was washed with n-hexanegiving crude acetal product (5.5g). Next, to a solution ofthis crude acetal (5.5g) in THF (86mL), LiAlH4(2.0Min THF, 8.6mL, 17.2mmol) was added dropwise at 0°Cfor 10min, then the reaction mixture stirred at room temperaturefor 5 h. The reaction was quenched with icecoldaq. satd. NH4Cl,then the whole was extracted withEtOAc. The EtOAc extract was washed with aq satd NaCland dried over MgSO4.Removal of the solvent from theEtOAc extract under reduced pressure gave a residue,which was purified by column chromatography (SiO2 200g,n-hexane:EtOAc = 3:1) to afford tetraol 7 (5.2g, 95%).Tetraol 7; a colorless amorphous powder, 1H-NMR(CDCl3) : 4.20 (4H, s), 6.77 (2H, s), 7.38-7.64 (20H, m).IR (KBr): 3063, 1630cm-1; FAB-MS m/z: 639 (M + H)+.HRFAB-MS m/z: 639.1944 (Calcd for C40H31O8+:639.1941).

Reference： [1]Tamura, Satoru; Yang, Gang-Ming; Koitabashi, Teruaki; Matsuura, Yoshiharu; Komoda, Yasumasa; Kawano, Tomikazu; Murakami, Nobutoshi [Natural Medicines, 2019, vol. 73, # 1, p. 67 - 75]

14
[ 121-79-9 ]
[ 476-66-4 ]

Yield	Reaction Conditions	Operation in experiment
82%	With 3-chloro-benzenecarboperoxoic acid; In sulfuric acid; at 80℃; for 12h;	Weigh 20g of gallic acid,Placed in the reaction flask,Then add 10% H2SO4 60mL,Stir and heat to 80 C,After dissolving methyl gallate,20 g of m-CPBA was added, and the reaction was stirred under reflux for 12 h to stop the reaction.The reaction solution was cooled and crystallized, filtered, and the filter cake was washed with hot water at 80 C.The filter cake was dissolved in a 10% NaOH solution, and 20 g of activated carbon was charged.The mixture was decolorized by stirring at 25 C, filtered, and the filtrate was extracted three times with ethyl acetate.The aqueous phase was adjusted to pH 1.5 with 10% hydrochloric acid.Crystallization, filtration, vacuum drying to obtain pale yellow ellagic acid,The yield is 82% and the relative content is up to 91%.

Reference： [1]Patent: CN110066284,2019,A .Location in patent: Paragraph 0055-0058

15
[ 2897618-99-2 ]
[ 476-66-4 ]

Yield	Reaction Conditions	Operation in experiment
93%	With hydrogenchloride In isopropyl alcohol at 20℃; for 14h; Inert atmosphere;	Ellagic acid (1). A solution of dimer 8 (0.1 g, 0.22 mmol), 1N HCl (1 mL) in isopropanol (10 mL) was stirred at room temperature over night. Then the isopropanol was removed in vacuum and the resulting mixture was extracted with ethyl ether. The combined organic phases were dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a mixture of hexane/ethyl acetate: 1/1 giving the ellagic acid (0.060 g, 0.11 mmol, 93%) as white solid (mp > 400 °C, mp > 350 °C).20 Rf (hexane/ethyl acetate) = 0.40. 1H NMR (DMSO-d6, 400 MHz) δ (ppm), 7.39 (s, 2H, CH-). 13C NMR (DMSO-d6, 100.6 MHz) δ (ppm), 107.9 C-C x 2), 112.9 (CH x 2), 114.2 (C-C x 2), 137.4 (C-O x 2), 139.7 (C-O x 2), 148.6 (C-O x 2), 158.5 (C=O x 2). Elem. Anal. Calcd. for C14H6O8: C, 55.64; H, 2.00, Found: C, 56.00; H, 2.22.
93 %	With hydrogenchloride In isopropyl alcohol at 20℃; Inert atmosphere;	Ellagic acid (1). A solution of dimer 8 (0.1 g, 0.22 mmol), 1N HCl (1 mL) in isopropanol (10 mL) was stirred at room temperature over night. Then the isopropanol was removed in vacuum and the resulting mixture was extracted with ethyl ether. The combined organic phases were dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a mixture of hexane/ethyl acetate: 1/1 giving the ellagic acid (0.060 g, 0.11 mmol, 93%) as white solid (mp > 400 °C, mp > 350 °C).20 Rf (hexane/ethyl acetate) = 0.40. 1H NMR (DMSO-d6, 400 MHz) δ (ppm), 7.39 (s, 2H, CH-). 13C NMR (DMSO-d6, 100.6 MHz) δ (ppm), 107.9 C-C x 2), 112.9 (CH x 2), 114.2 (C-C x 2), 137.4 (C-O x 2), 139.7 (C-O x 2), 148.6 (C-O x 2), 158.5 (C=O x 2). Elem. Anal. Calcd. for C14H6O8: C, 55.64; H, 2.00, Found: C, 56.00; H, 2.22.

Reference： [1]Navarro, Francesc; Hamri, Salha; Reches, Rosa; Viñas, Miquel; Jahani, Daniel; Ginard, Jaume; Vilardell, Josep; Abián, Olga; Pujol, M. Dolors [Synthesis, 2023, vol. 55, # 4, p. 657 - 662]
[2]Navarro, Francesc; Hamri, Salha; Reches, Rosa; Viñas, Miquel; Jahani, Daniel; Ginard, Jaume; Vilardell, Josep; Abián, Olga; Pujol, M. Dolors [Synthesis, 2023, vol. 55, # 4, p. 657 - 662]

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P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
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. 476-66-4 ] {[proInfo.proName]}

Quality Control of [ 476-66-4 ]

Related Doc. of [ 476-66-4 ]

Product Details of [ 476-66-4 ]

Calculated chemistry of [ 476-66-4 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 476-66-4 ]

Application In Synthesis of [ 476-66-4 ]

[ 476-66-4 ] Synthesis Path-Upstream 1~2

[ 476-66-4 ] Synthesis Path-Downstream 1~15

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry