Anacardic Acid
Structural Formula Vector Image
Title: Anacardic Acid
Literature References: Principal constituent of cashew nut-shell liquid, Anacardium occidentalis L., Anacardiaceae, member of the family of non-isoprenoid long-chain phenols. (See also Urushiol.) Anacardic acid is a mixture of 2-hydroxy-6-alkylbenzoic acids in which the alkyl chain (C11 or higher) is fully saturated (I) or is a monoene (II), a diene (III) or a triene (IV). The name anacardic acid is also used in the literature to designate one component of the mixture: 6-pentadecyl-2-hydroxybenzoic acid (I) (6-pentadecylsalicylic acid). Another component of the mixture 6-(8-pentadecenyl)-2-hydroxybenzoic acid (II), is also known as ginkgoic acid. Isoln and structure: Städeler, Ann. 63, 137 (1847); Ruhemann, Skinner, Ber. 20, 1861 (1887); Haagen, Smit, K. Akad. Wetensch. 34, 165 (1931); Backer, Haack, Rec. Trav. Chim. 660, 61 (1941); Kremers, US 2431127 (1947). Structure of side chain: Sletzinger, Dawson, J. Org. Chem. 14, 670, 849 (1949). Structure of unsaturated components: J. H. P. Tyman, N. Jacobs, J. Chromatogr. 54, 83 (1971). GLC analysis of components: J. H. P. Tyman, ibid. 111, 285 (1975). Synthesis and prostaglandin synthetase inhibiting activity of I and II: Y. Yamagiwa et al., Tetrahedron 43, 3387 (1987); of I: I. Kubo et al., Chem. Lett. 1987, 1101. Antitumor activity of I: H. Itokawa et al., Chem. Pharm. Bull. 35, 3016 (1987). Review: J. H. P. Tyman, Chem. Soc. Rev. 8, 499-537 (1979).
Properties: Mixture, crystals from acetone, mp 34-37°. Sparingly sol in water; freely sol in alc, ether, petr ether. Forms a water-soluble sodium salt.
Melting point: mp 34-37°
Derivative Type: 6-Pentadecyl component (I)
Properties: Needles from hexane, mp 90.2-91.5°.
Melting point: mp 90.2-91.5°
Derivative Type: 6-(8-Pentadecenyl) component (II)
Properties: Needles, mp 45.3-48° (subl).
Melting point: mp 45.3-48° (subl)

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