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506-32-1

Basic Information
CAS No.: 506-32-1
Name: 5,8,11,14-Eicosatetraenoicacid, (5Z,8Z,11Z,14Z)-
Article Data: 36
Cas Database
Molecular Structure:
Molecular Structure of 506-32-1 (5,8,11,14-Eicosatetraenoicacid, (5Z,8Z,11Z,14Z)-)
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
Hazard Symbols: N/A
Risk Codes: 19
Safety: 24/25
Transport Information: N/A
PSA: 37.30000
LogP: 6.21670
Synthetic route
95285-77-1, 1808-26-0

ethyl arachidonate

506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

Conditions
ConditionsYield
With triethylamine In water; acetonitrile at 30℃; under 7500600 Torr; for 96h;78%
With potassium hydroxide
1191-85-1

eicosa-5,8,11,14-tetraynoic acid

506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
(i) EtMgBr, Et2O, (ii) /BRN= 1900390/, Et2O; Multistep reaction;
124-38-9

carbon dioxide

C19H31ClMg

506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With sodium hydroxide In ethanol for 12h; Ambient temperature; Yield given;
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    Arachidonic acid Basic information Product Name: Arachidonic acid Synonyms: (5Z,8Z,11Z,14Z)-5,8,11,14-Icosatetraenoic acid;(all-Z)-5,8,11,14-Eicosatetraenoic acid;(all-z)-5,8,11,14-eicosatetraenoicacid;5,8,11,14-Eicosatetraenoic acid, (all-Z)-

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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.



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.