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| CAS No.: | 506-32-1 |
|---|---|
| Name: | Arachidonic acid |
| Molecular Structure: | |
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| Formula: | C20H32O2 |
| Molecular Weight: | 304.473 |
| Synonyms: | 5,8,11,14-Eicosatetraenoicacid, (all-Z)- (8CI);(all-Z)-5,8,11,14-Eicosatetraenoic acid;5,8,11,14-all-cis-Eicosatetraenoic acid;5-cis,8-cis,11-cis,14-cis-Eicosatetraenoic acid;5Z,8Z,11Z,14Z-Eicosatetraenoicacid;A 0871;Arachidonic acid;Immunocytophyte;all-cis-5,8,11,14-Eicosatetraenoic acid;cis-D5,8,11,14-Eicosatetraenoic acid; |
| EINECS: | 208-033-4 |
| Density: | 0.929 g/cm3 |
| Melting Point: | -49 °C(lit.) |
| Boiling Point: | 407.45 °C at 760 mmHg |
| Flash Point: | 336.308 °C |
| Solubility: | ethanol: ≥10 mg/mL |
| Appearance: | colorless to light yellow oil |
| Risk Codes: | 19 |
| Safety: | 24/25 |
| PSA: | 37.30000 |
| LogP: | 6.21670 |
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- 95285-77-1, 1808-26-0
ethyl arachidonate
- 506-32-1
all cis 5,8,11,14-eicosatetraenoic acid
| Conditions | Yield |
|---|---|
| With triethylamine In water; acetonitrile at 30℃; under 7500600 Torr; for 96h; | 78% |
| With potassium hydroxide |
| Conditions | Yield |
|---|---|
| With sodium tetrahydroborate; hydrogen; ethylenediamine; nickel diacetate In ethanol at 20℃; | 34% |
| With hydrogen; Lindlar's catalyst In methanol | |
| With quinoline; water; hydrogen; Lindlar's catalyst 1.) AcOEt; Yield given. Multistep reaction; |
- 38575-18-7
arachidonic acid methyl ester
- 506-32-1
all cis 5,8,11,14-eicosatetraenoic acid
| Conditions | Yield |
|---|---|
| With potassium hydroxide; ethanol |
- 612852-05-8
1-chloro-nonadeca-4c,7c,10c,13c-tetraene
- 124-38-9
carbon dioxide
- 506-32-1
all cis 5,8,11,14-eicosatetraenoic acid
| Conditions | Yield |
|---|---|
| (i) EtMgBr, Et2O, (ii) /BRN= 1900390/, Et2O; Multistep reaction; |
| Conditions | Yield |
|---|---|
| In tetrahydrofuran |
- 40924-42-3
2-trans-Alken-5,8,11,14-eicosatetrainsaeure
- 506-32-1
all cis 5,8,11,14-eicosatetraenoic acid
| Conditions | Yield |
|---|---|
| With pyridine; hydrogen; Lindlar's catalyst In ethyl acetate |
- 13553-09-8
(3Z,6Z)-1-oxo-dodecadienal
- 17814-85-6
(4-carboxybutyl)triphenylphosphonium bromide
- 506-32-1
all cis 5,8,11,14-eicosatetraenoic acid
| Conditions | Yield |
|---|---|
| With sodium hexamethyldisilazane 1.) THF, HMPA, RT, 2 h, 2.) from -100 to 0 deg C, 4 h; Multistep reaction; |
- 86179-96-6
(5Z,8Z,11Z,14Z)-20-hydroxyeicosa-5,8,11,14-tetraenoic acid methyl ester
- 506-32-1
all cis 5,8,11,14-eicosatetraenoic acid
| Conditions | Yield |
|---|---|
| With lithium aluminium tetrahydride 1.) tosylation;; Multistep reaction; |
- 113516-18-0
arachidonic acid TMS ester
- 506-32-1
all cis 5,8,11,14-eicosatetraenoic acid
| Conditions | Yield |
|---|---|
| With sodium thiosulfate In water Yield given; |
- 119520-63-7
(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid isobutyl ester
- 506-32-1
all cis 5,8,11,14-eicosatetraenoic acid
| Conditions | Yield |
|---|---|
| With sodium hydroxide In ethanol for 12h; Ambient temperature; Yield given; |
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Specification
The IUPAC name of Arachidonic acid is (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid. With the CAS registry number 506-32-1, it is also named as 5,8,11,14-Eicosatetraenoic acid. The product's categories are Industrial / Fine Chemicals; Fatty & Aliphatic Acids, Esters, Alcohols & Derivatives; Mixed Fatty Acids; Higher Fatty Acids & Higher Alcohols; Unsaturated Higher Fatty Acids; Biochemistry; Fatty Acid Derivatives & Lipids; Glycerols. Besides, it is colorless to light yellow oil, which should be stored in in a tightly closed container in a cool, dry, well-ventilated area away from incompatible substances below -20 °C. It may form explosive peroxides. When you are using this chemical, please avoid contact with skin and eyes.
The other characteristics of this product can be summarized as: (1)EINECS: 208-033-4; (2)ACD/LogP: 6.99; (3)# of Rule of 5 Violations: 1; (4)ACD/LogD (pH 5.5): 6.175; (5)ACD/LogD (pH 7.4): 4.378; (6)ACD/BCF (pH 5.5): 18467.777; (7)ACD/BCF (pH 7.4): 294.752; (8)ACD/KOC (pH 5.5): 23056.098; (9)ACD/KOC (pH 7.4): 367.984; (10)#H bond acceptors: 2; (11)#H bond donors: 1; (12)#Freely Rotating Bonds: 14; (13)Index of Refraction: 1.501; (14)Molar Refractivity: 96.502 cm3; (15)Molar Volume: 327.755 cm3; (16)Surface Tension: 35.226 dyne/cm; (17)Density: 0.929 g/cm3; (18)Flash Point: 336.308 °C; (19)Melting point: -49.5 °C; (20)Solubility: Ethanol: ≥10 mg/mL; (21)Enthalpy of Vaporization: 72.345 kJ/mol; (22)Boiling Point: 407.45 °C at 760 mmHg; (23)Vapour Pressure: 0 mmHg at 25 °C.
Preparation of Arachidonic acid: you can get mycelium by the fermentation and cultivating of white Mortierella alpina. Then please filtrate and squeeze. And you will obtain the product by purification, after use CO2 to extract.
Uses of Arachidonic acid: this chemical is a precursor in the production of eicosanoids. It is also used to produce the prostaglandins, prostacyclin, thromboxanes, and leukotrienes. Moreover, it is used in the biosynthesis of anandamide. The product is necessary for the repair and growth of skeletal muscle tissue. In addition, it can help to maintain hippocampal cell membrane fluidity and protect the brain from oxidative stress by activating perioxisomal proliferator-activated receptor-y. Furthermore, it can be used to produce Eicosa-5c,8c,11c,14c-tetraen-1-ol.
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This reaction needs LiAlH4 and Diethyl ether at temperature of 10 °C for 30 min. The yield is 100 %.
People can use the following data to convert to the molecule structure.
(1)SMILES: CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O
(2)InChI: InChI=1/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-15-
(3)InChIKey: YZXBAPSDXZZRGB-DOFZRALJBE
(4)Std. InChI: InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-15-
(5)Std. InChIKey: YZXBAPSDXZZRGB-DOFZRALJSA-N
The toxicity data is as follows:
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD50 | intravenous | 39200ug/kg (39.2mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 274, Pg. 4, 1985. |