506-45-6|22-Hydroxydocosanoic acid| Ambeed

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Quality Control of [ 506-45-6 ] Purity: 98% SDS Specification

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Product Details of [ 506-45-6 ]

CAS No. :	506-45-6
Formula :	C₂₂H₄₄O₃
M.W :	356.58
SMILES Code :	O=C(O)CCCCCCCCCCCCCCCCCCCCCO
MDL No. :	MFCD02259052
InChI Key :	IBPVZXPSTLXWCG-UHFFFAOYSA-N
Pubchem ID :	5282922

Safety of [ 506-45-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 506-45-6 ]

* 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.

Downstream synthetic route of [ 506-45-6 ]

[ 506-45-6 ] Synthesis Path-Downstream 1~24

1
[ 7511-30-0 ]
[ 506-45-6 ]

References: [1]Bulletin de la Societe Chimique de France,1957,p. 1232,1236.

2
[ 97157-86-3 ]
[ 506-45-6 ]

References: [1]Bulletin de la Societe Chimique de France,1963,p. 142 - 144.

3
[ 506-45-6 ]
[ 78774-39-7 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1984,vol. 103,p. 348 - 351.

4
[ 96303-15-0 ]
[ 506-45-6 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1984,vol. 103,p. 348 - 351.

7
potassium-salt of/the/ docosanedioic acid [ No CAS ]
[ 506-45-6 ]

References: [1]Annales de Chimie (Cachan, France),1963,vol. <13>8,p. 315,328.

8
18-hydroxyoctadec-9-enoic acid, sodium salt [ No CAS ]
9,10-epoxy-18-hydroxyoctadecanoic acid, sodium salt [ No CAS ]
threo-9,10,18-trihydroxyoctadecanoic acid, sodium salt [ No CAS ]
22-hydroxydocosanoic acid, sodium salt [ No CAS ]
sodium betulinate [ No CAS ]
[ 3329-38-2 ]
[ 3233-92-9 ]
threo-9,10,18-trihydroxyoctadecanoic acid [ No CAS ]
[ 506-45-6 ]
[ 472-15-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In water;	Preparation of suberinic and betulinic free acidsProduct V was acidified with a 2% solution of HCl in water (35 L) and the solution was then filtered. The solid residue recovered from the filter was washed twice with water (10 L) and dried at 40-45 C in vacuum (200 mm Hg) for 8 hours to yield VI (3.38 kg). Product VI comprises the acidic organic compounds free acid form 204 of the preferred embodiment shown in Figure 1.Composition of VI 18-Hydroxyoctadec-9-enoic acid 11.66 %18-hydroxy-9, 10-epoxyoctadecanoic acid 44.6 %Threo-9, 10,18 -trihydroxyoctadecanoic acid 11.3 %22-Hydroxydocosanoic acid 11.66 %Betulinic acid 12.86 % Other ω-hydroxy fatty acids 7.8 %; Preparation of suberinic and betulinic free acids Pressed outer birch bark (1 kg, d=0.6 g/ml) was added portionally to a solution of NaOH (230 g, 5.75 mol) in H2O (90 ml) and EtOH (2.5 L) at 70 0C. The reaction mixture was refluxed with good stirring for 1 hr. Xylenes (6 L) was then added to the reaction mixture. A solution of EtOH and H2O in xylenes (3.6 L) was distilled from the reaction mixture. Distillation was continued until temperature of vapors reached 133 0C. An additional amount of H2O (15 ml) was distilled from the reaction mixture by using a Dean-Stark receiver. The reaction mixture was filtrated at 800C. Solid part was added to xylenes (3 L) and refluxed for 1 hr. H2O (15 ml) was distilled from the reaction mixture by using a Dean-Stark receiver and the reaction mixture was filtered at 80 0C. Washing of solid part with xylenes (3 L) was repeated. Solid part after extraction with xylenes were added to ethanol (8 liters) and refluxed for 1 hour. The reaction mixture was filtrated at 700C and solid part was added to ethanol (4 L) and refluxed for 1 hr. The reaction mixture was filtrated at 70 0C and solid part was extracted with ethanol (4 L) using the same procedure as is it was described above. Ethanol solutions were combined, evaporated from solvent and dried in vacuum at 80 0C to give the acids as their sodium salts (330 g), which, was acidified with a 2 % solution of HCl (2.3 L) and filtered. The solid residue was washed twice with water (10 L) and dried in vacuum (200 mm Hg) at 40-45 0C <n="42"/>for 8 hours to give XVII (250 g). Product XVII comprises the acidic organic compounds free acid form 204 of the preferred embodiment shown in Figure 2. Composition of XVII1 S-Hydroxyoctadec-9-enoic acid 11.4 % 18-Hydroxyl-9,10-epoxyoctadecanoic acid 43.8 % Threo-9, 10, 18-trihydroxyoctadecanoic acid 12.1 % 22-Hydroxydocosanoic acid 11.84 %Betulinic acid 12.78 %Other ω-hydroxy fatty acids 8.14 %

References: [1]Patent: WO2007/121482,2007,A1 .Location in patent: Page/Page column 34; 40-41.

9
18-hydroxyoctadec-9-enoic acid, potassium salt [ No CAS ]
9,10-epoxy-18-hydroxyoctadecanoic acid, potassium salt [ No CAS ]
threo-9,10,18-trihydroxyoctadecanoic acid, potassium salt [ No CAS ]
22-hydroxydocosanoic acid, potassium salt [ No CAS ]
potassium betulinate [ No CAS ]
[ 3329-38-2 ]
[ 3233-92-9 ]
threo-9,10,18-trihydroxyoctadecanoic acid [ No CAS ]
[ 506-45-6 ]
[ 472-15-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In water;	Preparation of suberinic and betulinic free acidsProduct XI was acidified with a 2% solution of HCl in water (35 L) and the solution was then filtered. The solid residue recovered from the filter was washed twice with water (10 L) then dried at 40-45 0C under vacuum (200 mm Hg.) for 8 hours to yield XII (5.28 kg). Product XI comprises the acidic organic compounds free acid form 204 of the preferred embodiment shown in Figure 1. Composition of XII1 δ-Hydroxyoctadec-Q-enoic acid 11.23 %18-hydroxy-9, 10-epoxyoctadecanoic acid 34.3 % t/jreo-9,0,18-trihydroxyoctadecanoic acid 14.9 %22-Hydroxydocosanoic Acid 14.99 %Betulinic acid 5.8 %Other ω-Hydroxy fatty acids 18.2 %; Preparation of suberinic and bctulinic free acidsPressed outer birch bark (1 kg) was added in portions to a solution of KOH (300 g, 5.35 mol) in H2O (60 ml) and EtOH (2.0 L) at 70 0C. The reaction mixture was refluxed with good stirring for 1 hr. Xylenes (6 L) was then added to the reaction mixture. A solution of EtOH and H2O in xylenes (3.6 L) was distilled from the reaction mixture. Distillation was continued until temperature of vapors reached 133 0C. An additional amount of H2O (15 ml) was distilled from the reaction mixture using a Dean-Stark receiver. The reaction mixture was filtered at 80 0C. The solid residue was added to xylenes (3 L) and refluxed for 1 hr. Water (15 ml) was distilled from the reaction mixture using a Dean- Stark receiver and the reaction mixture was filtered at 80 0C. Washing of the solid residue with xylenes (3 L) was repeated. The solid residue after extraction with xylenes was added to ethanol (8 L) and refluxed for 1 hr. The mixture was filtered at 70 0C and the extraction with EtOH was repeated twice using 4 L of EtOH. After filtration at 70 0C, the combined ethanol solutions were evaporated and the residue cidified with a 2 % solution of HCl in water (2.5 L). The precipitate was separated by filtration, washed twice with water (1 L), and dried at 40-45 0C under vacuum (200 mm Hg) for 8 hours giving XXII (341 g) Composition of XXII 18-Hydroxyoctadec-9-enoic acid 10.14 %18-Hydroxy-9, 10-epoxyoctadecanoic acid 40.8 %Threo-9, 10,18-trihydroxyoctadecanoic acid 10.1 %22-Hydroxydocosanoic acid 12.6 %Betulinic acid 7.98 % Other ω-hydroxy fatty acids 18.38 %

References: [1]Patent: WO2007/121482,2007,A1 .Location in patent: Page/Page column 37; 44.

10
[ 2777-65-3 ]
Lindlar-catalyst [ No CAS ]
[ 506-45-6 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1984,vol. 103,p. 348 - 351.

11
[ 506-45-6 ]
[ 89022-38-8 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1984,vol. 103,p. 348 - 351.

12
[ 506-45-6 ]
[ 89022-15-1 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1984,vol. 103,p. 348 - 351.

13
[ 506-45-6 ]
[ 96303-19-4 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1984,vol. 103,p. 348 - 351.

14
[ 506-45-6 ]
[ 96303-17-2 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1984,vol. 103,p. 348 - 351.

15
[ 506-45-6 ]
32-hydroxy-23-dotriacontynoic acid ester of linoleic acid [ No CAS ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1984,vol. 103,p. 348 - 351.

16
[ 13030-63-2 ]
[ 506-45-6 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1984,vol. 103,p. 348 - 351.

17
[ 96303-14-9 ]
[ 506-45-6 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1984,vol. 103,p. 348 - 351.

18
[ 22399-98-0 ]
[ 506-45-6 ]

References: [1]Bulletin de la Societe Chimique de France,1957,p. 1232,1236.

19
[ 177177-92-3 ]
[ 506-45-6 ]

Yield	Reaction Conditions	Operation in experiment
53%	With hydrogen;palladium-carbon; palladium; In ethanol;	Synthesis of 22-Hydroxydocosanoic Acid 8 (Formula V) Into a clean, dry 500 ml two neck flask, were charged 2.0 g (1.8 mmole) of 10% palladium on carbon catalyst. The flask is equipped with a stir bar and a rubber septa. In a separate flask, 9.0 g (0.02 moles) of 22-benzyloxydocosanoic acid were dissolved in 300 mls of 2/1 ethanol/ether by sonicating for 30 minutes. This solution was charged with hydrogen gas (1 atmosphere). The reaction was stirred overnight at room temperature before the solution was recharged with hydrogen. Reaction appeared to be complete after about 40 hours at room temperature. The contents of the flask were gravity filtered before being washed several times with ethanol. The filtrate was concentrated under vacuum to give 2.4 g of white powder. In addition, the filtered Pd/C catalyst was stirred in boiling ethanol for 30 minutes and filtered while still hot. The filtrate was concentrated under vacuum to give 2.9 g of 22-hydroxy docosanoic acid. Overall yield: 53% Melting Point: Capillary=95-96 C. DSC=96.0 C. IR (nujol mull): 2620 (br. w), 1710 (s) 1 H NMR (200 MHz, CDCL3): d 3.6 (t, 2H), 2.3 (t, 2H), 1.6 (br. m, 4H), 1.2 (br. s, 36H) STR4

References: [1]Patent: US5502226,1996,A .

20
suberin [ No CAS ]
[ 4494-16-0 ]
[ 3329-38-2 ]
C₁₇H₃₂O₄ [ No CAS ]
[ 69232-68-4 ]
[ 506-45-6 ]
[ 496-86-6 ]
[ 505-56-6 ]

Yield	Reaction Conditions	Operation in experiment
		Air-dried bark was cut in strips, granulated and ground to give a powder having particles of 20 mesh, followed by extraction of said powder for 24 hours with aceton in a Soxhlet apparatus. The remaining solid material was filtered and dried. The solid material (100 g) was refluxed in basic 2-propanol (22 g/0.55 mol NaOH in 1 liter of alcohol) for 1 hour. The solid material was filtered from the solution while still hot. The solution was still refluxed for 15 min. The solution was kept in a freezer at least 24 hours. The precipitate was filtered and dried. The product containing sodium salts of carboxylic acids of suberin was a yellowish powder. EPO <DP n="19"/>Example 2Preparation of suberin acidsThe hydrolysis product of suberin (6 g) obtained in Example 1 was dissolved in water (750 ml) in a bath at about 100 C, followed by cooling the solution. 0.25 M sulphuric acid was added to the solution to adjust the pH of the solution between 2 and 3. The mixture was extracted with diethyl ether (400 + 200 + 200 ml) and dried with sodium sulphate. The solvent was removed by means of a rotary evaporator, followed by drying of the product in vacuum at room temperature. The product contained fatty acids of suberin, the yield thereof being between 84 and 90 %. The product was a yellowish powder.1H NMR (ppm): 1.0-1.6(m) CH2; 2.0 CH2; 2.2(t) CH2CO2; 2.8 CH(O)CH; 3.2 CH(OH)CH(OH); 3.4(t) CH2OH; 3.8 CH(OH); 4.0, 4.2 OH; 5.3 CH=CH; 11.8 OH 13C NMR (ppm): 24-28(5s) CH2; 29(m), 32 CH2; 34 CH2COOH; 37 CH2CH(OH); 56 CH(O)CH; 61 CH2OH; 70 CH(OH); 73 CH(OH)CH(OH); 130 CH=CH; 174 COOHContents of Fatty acid content of suberin is shown in Table 4, by NMR analysis.Table 4. Fatty acids of suberin

References: [1]Patent: WO2007/45728,2007,A1 .Location in patent: Page/Page column 17-18.

21
11-bromo-10-undecyn-1-ol [ No CAS ]
[ 506-45-6 ]

References: [1]Angewandte Chemie - International Edition,2021,vol. 60,p. 19843 - 19851.
Angew. Chem.,2021,vol. 133,p. 19996 - 20004.

22
[ 2777-65-3 ]
[ 506-45-6 ]

References: [1]Angewandte Chemie - International Edition,2021,vol. 60,p. 19843 - 19851.
Angew. Chem.,2021,vol. 133,p. 19996 - 20004.

23
[ 506-45-6 ]
[ 58296-51-8 ]

References: [1]Angewandte Chemie - International Edition,2021,vol. 60,p. 19843 - 19851.
Angew. Chem.,2021,vol. 133,p. 19996 - 20004.

24
22-hydroxydocosa-10,12-diynoic acid [ No CAS ]
[ 506-45-6 ]

References: [1]Angewandte Chemie - International Edition,2021,vol. 60,p. 19843 - 19851.
Angew. Chem.,2021,vol. 133,p. 19996 - 20004.

Historical Records

Technical Information

• Appel Reaction • Arndt-Eistert Homologation • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chugaev Reaction • Corey-Kim Oxidation • Dess-Martin Oxidation • Heat of Combustion • Hunsdiecker-Borodin Reaction • Hydride Reductions • Jones Oxidation • Martin's Sulfurane Dehydrating Reagent • Mitsunobu Reaction • Moffatt Oxidation • Oxidation of Alcohols by DMSO • Passerini Reaction • Preparation of Alcohols • Preparation of Amines • Preparation of Carboxylic Acids • Reactions of Alcohols • Reactions of Amines • Reactions of Carboxylic Acids • Reactions with Organometallic Reagents • Ritter Reaction • Schmidt Reaction • Sharpless Olefin Synthesis • Specialized Acylation Reagents-Ketenes • Swern Oxidation • Ugi Reaction

Related Functional Groups of
[ 506-45-6 ]

Aliphatic Chain Hydrocarbons

A105129 [3710-42-7]

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A114969 [1679-53-4]

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A123107 [2424-92-2]

Icosanedioic acid

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A157334 [3788-56-5]

9-Hydroxynonanoic acid

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A170816 [505-52-2]

Tridecanedioic acid

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Alcohols

A105129 [3710-42-7]

7-Hydroxyheptanoic acid

Similarity: 1.00

A111111 [505-95-3]

12-Hydroxydodecanoic acid

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A114969 [1679-53-4]

10-Hydroxydecanoic acid

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A157334 [3788-56-5]

9-Hydroxynonanoic acid

Similarity: 1.00

Carboxylic Acids

A105129 [3710-42-7]

7-Hydroxyheptanoic acid

Similarity: 1.00

A114969 [1679-53-4]

10-Hydroxydecanoic acid

Similarity: 1.00

A123107 [2424-92-2]

Icosanedioic acid

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A157334 [3788-56-5]

9-Hydroxynonanoic acid

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A170816 [505-52-2]

Tridecanedioic acid

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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

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CAS No.: 506-45-6

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