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Basic Information

Molecular Structure:
CAS No.:	506-32-1
Name:	Arachidonic acid
Article Data:	36

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

Synthetic route

: 95285-77-1, 1808-26-0
ethyl arachidonate

: 506-32-1
all cis 5,8,11,14-eicosatetraenoic acid

Conditions

Conditions	Yield
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

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

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

Conditions	Yield
(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

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

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

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

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

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

Conditions	Yield
With sodium hydroxide In ethanol for 12h; Ambient temperature; Yield given;

Raw Materials

628-71-7

Downstream Products

110-15-6

551-11-1

110-94-1

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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.