Title: 5-HETE
CAS Registry Number: 70608-72-9
CAS Name: (5S,6E,8Z,11Z,14Z)-5-Hydroxy-6,8,11,14-eicosatetraenoic acid
Additional Names: (S)-5-hydroxy-6-trans-8,11,14-cis-eicosatetraenoic acid
Molecular Formula: C20H32O3
Molecular Weight: 320.47
Percent Composition: C 74.96%, H 10.06%, O 14.98%
Literature References: Important intermediate in a series of biosynthetic processes leading from arachidonic acid, q.v., to a number of biologically active compounds. First discovered during the transformation of arachidonic acid by rabbit peritoneal polymorphonuclear leukocytes: P. Borgeat et al., J. Biol. Chem. 251, 7816 (1976). Revised description: eidem, ibid. 252, 8772 (1977). It has also been found during metabolism of arachidonic acid by human peripheral blood polymorphonuclear leukocytes: P. Borgeat, B. Samuelsson, Proc. Natl. Acad. Sci. USA 76, 2148 (1979); and has been shown to be strongly chemotactic for human eosinophils and neutrophils: E. J. Goetzl et al., Immunology 39, 491 (1980); E. J. Goetzl, N. Engl. J. Med. 303, 822 (1980). 5-HETE is formed via 5-HPETE (5-hydroperoxy-6,8,11,14-eicosatetraenoic acid), a precursor of the leukotrienes, q.v. Chemical and enzymic syntheses of 5-HETE and 5-HPETE: E. J. Corey et al., J. Am. Chem. Soc. 102, 1435 (1980). Synthesis via phenylselenylation of arachidonic acid: J. E. Baldwin et al., Tetrahedron 37, Suppl. 1, 263 (1981). Large-scale synthesis of 5-HETE: E. J. Corey, S. Hashimoto, Tetrahedron Lett. 22, 299 (1981). Biosynthetic study: R. C. Mebane, Diss. Abstr. B 42, 2839 (1982). Selected synthesis of octadeuterated (±)-5-HETE: W. C. Hubbard et al., Prostaglandins 23, 61 (1982). Stereospecific syntheses of 5-(S)- and 5-(R)-HETE and transformation to (±)-5-HPETE: R. Zamboni, J. Rokach, Tetrahedron Lett. 24, 999 (1983). Review of syntheses: J. G. Atkinson, J. Rokach, in Handbook of Prostaglandins and Related Lipids: The Eicosanoids, A. L. Willis et al., Eds. (CRC Press, Boca Raton, in press).
Derivative Type: Methyl ester
Molecular Formula: C21H34O3
Molecular Weight: 334.49
Percent Composition: C 75.41%, H 10.25%, O 14.35%
Properties: Colorless oil. [a]D23 +14.0°; [a]23436 +35.7° (c = 2.02 in benzene).
Optical Rotation: [a]D23 +14.0°; [a]23436 +35.7° (c = 2.02 in benzene)

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