ARACHIDONIC ACID

PRODUCT IDENTIFICATION

CAS NO. 506-32-1, 7771-44-0

ARACHIDONIC ACID 

EINECS NO. 208-033-4
FORMULA CH3(CH2)4(CH=CHCH2)4CH2CH2COOH
MOL WT. 304.47

H.S. CODE

2916.19.3000

TOXICITY

 
SYNONYMS (all-Z)-5,8,11,14-Eicosatetraenoic acid;
Arachidonate; (5Z,8Z,11Z,14Z)-5,8,11,14-Icosatetraenoic acid; Icosa-5,8,11,14-tetraenoic acid; ácido icosa-5,8,11,14-tetraenoico; Acide icosa-5,8,11,14-tétraénoïque; (5Z,8Z,11Z,14Z)-5,8,11,14-Eikosatetraensaeure;
SMILES C(=C\C\C=C\C\C=C\CCCCC)\C\C=C\CCCC(O)=O

CLASSIFICATION

Polyunsaturated fatty acid

EXTRA NOTES

An unsaturated, essential fatty acid. It is found in animal and human fat as well as in the liver, brain, and glandular organs, and is a constituent of animal phosphatides. It is formed by the synthesis from dietary linoleic acid and is a precursor in the biosynthesis of prostaglandins, thromboxanes, and leukotrienes.

PHYSICAL AND CHEMICAL PROPERTIES (40% in EtOH)

PHYSICAL STATE slightly yellow free-flowing liquid
MELTING POINT -49 C
BOILING POINT 169 - 171 C at 0.15 mmHg
SPECIFIC GRAVITY 0.92
SOLUBILITY IN WATER Practically insoluble
SOLVENT SOLUBILITY Soluble in ethanol, ether
pH  
VAPOR DENSITY

 

log P 6.98 (Octanol-water)
VAPOR PRESSURE 1.55E-07 (mmHg at 25 C)
HENRY LAW CONSTANT 5.38E-05 (atm-m3/mole at 25 C)
OH RATE CONSTANT 2.38E-10 (cm3/molecule-sec at 25 C Atmospheric)

AUTOIGNITION

 

NFPA RATINGS

 

REFRACTIVE INDEX

1.4872
FLASH POINT > 112 C
STABILITY Stable under ordinary conditions

EXTERNAL LINKS & GENERAL DESCRIPTION

Wikipedia Linking

Google Scholar Search

http://www.sigmaaldrich.com/
Arachidonic acid (AA) is an unsaturated
6 fatty acid constituent of the phospholipids of cell membranes. Phospholipase A2 releases AA from the membrane phospholipids in response to inflammation. AA is subsequently metabolized to prostaglandins and thromboxanes by at least two cyclooxygenase (COX) isoforms, to leukotrienes and lipoxins by lipoxygenases, and to epoxyeicosatrienoic acids via cytochrome p450-catalyzed metabolism. AA and its metabolites play important roles in a variety of biological processes, including signal transduction, smooth muscle contraction, chemotaxis, cell proliferation and differentiation, and apoptosis. AA has been demonstrated to bind to the a subunit of G protein and inhibit the activity of Ras GTPase-activating proteins (GAPs). Cellular uptake of AA is energy dependent and involves protein-facilitated transport across the plasma membrane.

http://www.acnp.org/
In resting cells, arachidonic acid is stored within the cell membrane, esterified to glycerol in phospholipids. A receptor-dependent event, requiring a transducing G protein, initiates phospholipid hydrolysis and releases the fatty acid into the intracellular medium. Three enzymes may mediate this deacylation reaction: phospholipase A2 (PLA2), phospholipase C (PLC), and phospholipase D (PLD), whose different sites of attack on the phospholipid backbone are shown in
Fig. 2 (inset). PLA2 catalyzes the hydrolysis of phospholipids at the sn (stereospecific numbering)-2 position. Therefore, this enzyme can release arachidonate in a single-step reaction. By contrast, PLC and PLD do not release free arachidonic acid directly. Rather, they generate lipid products containing arachidonate (diacylglycerol and phosphatidic acid, respectively), which can be released subsequently by diacylglycerol- and monoacylglycerol-lipases

Local: Arachidonic acid is a polyunsaturated fatty acid (C-20 with four cis double bonds) and considered as a essential fatty acid; occurring in animal fats and also formed by biosynthesis from dietary linoleic acid. It is a precursor of eicosanoids which are biologically, physiologically and pathologically active on the cardiovascular, pulmonary, reproductive, and digestive systems as local hormones; including prostaglandins, thromboxanes, leukotrienes, and epoxyeicosatrienoic acids (EETs).

SALES SPECIFICATION
APPEARANCE slightly yellow free-flowing liquid
CONTENT 40.0% min

PEROXIDE

40 mg/kg

HEAVY METALS

1ppm max
CARBON DISTRIBUTION 2% max (14:0) + 4~15% (16:0) + 0~15% (16:1) +  4~15% (18:0) + 5~20% (18:1) + 3~10% (18:2) + 5% max (18:3) + 3% max (20:0) + 3% max (22:0) + 3~10% (20:3) + 40~50% (20:4) + 3% max (24:0) + 3% max (others)
TRANSPORTATION
PACKING
 
HAZARD CLASS  
UN NO.  
SAFETY INFORMATION
Hazard Symbols: n/a, Risk Phrases: n/a, Safety Phrases: 22-24/25

PRICE INFORMATION