Arachidonic Acid

Title: Arachidonic Acid
CAS Registry Number: 506-32-1
CAS Name: (5Z,8Z,11Z,14Z)-5,8,11,14-Eicosatetraenoic acid
Molecular Formula: C20H32O2
Molecular Weight: 304.47
Percent Composition: C 78.90%, H 10.59%, O 10.51%
Literature References: An essential fatty acid and a precursor in the biosynthesis of prostaglandins, thromboxanes, and leukotrienes, q.q.v. Structure: Mowry et al., J. Biol. Chem. 142, 679 (1942); Arcus, Smedley-Maclean, Biochem. J. 37, 1 (1943). Occurs in liver, brain, glandular organs, and depot fats of animals, in small amounts in human depot fats, and is a constituent of animal phosphatides. Isolation from liver lipids: Brown, J. Biol. Chem. 80, 455 (1928); from beef suprarenal phosphatides: Ault, Brown, ibid. 107, 615 (1934); Shinowara, Brown, ibid. 134, 331 (1940). See also Dolby et al., Biochem. J. 34, 1422 (1940). Synthesis from 2-propargyloxytetrahydropyran and 1-heptyne: Goldberg, Rachlin, US 2934570 (1960 to Hoffmann-La Roche); Rachlin et al., J. Org. Chem. 26, 2688 (1961). Alternate route: Osbond, Wickens, Chem. Ind. (London) 1959, 1288; Ege et al., J. Am. Chem. Soc. 83, 3080 (1961). Reviews: K. S. Markley, Fatty Acids Part I (Interscience, New York, 2nd ed., 1960) pp 164-167, 398-400; T. K. Schaaf, Annu. Rep. Med. Chem. 12, 182-190 (1977); B. B. Weksler, N. Engl. Soc. Allergy Proc. 2, 56-61 (1981); N. A. Nelson et al., Chem. Eng. News 60, 30-44 (Aug. 16, 1982). Series of articles on metabolism, role in inflammation and therapeutic implications: Drugs 33, Suppl. 1, 2-66 (1987).
Properties: Liquid. mp -49.5°. Neutralization value 184.20. Iodine value 333.50. nD20 1.4824.
Melting point: mp -49.5°
Index of refraction: nD20 1.4824
Derivative Type: Methyl ester
Molecular Formula: C21H34O2
Molecular Weight: 318.49
Percent Composition: C 79.19%, H 10.76%, O 10.05%
Properties: bp2 200-205°, bp0.001 127-128°. nD20 1.4797 to 1.4810.
Boiling point: bp2 200-205°; bp0.001 127-128°
Index of refraction: nD20 1.4797 to 1.4810
Therap-Cat: Nutrient (essential fatty acid).
Therap-Cat-Vet: With linoleic and linolenic acids, in eczema and dermatitis in dogs and swine.
Aramite? Aranidipine Araroba Arbaprostil Arbekacin