Structural Formula Vector Image
Title: Urushiol
Literature References: Main constituent of the irritant oil of poison ivy, Toxicodendron radicans (L.) Kuntze, poison oak, T. diversilobum, the Asiatic lacquer tree, T. verniciferum D.C. and other plants of the genus Toxicodendron, Anacardiaceae. Yoshida, J. Chem. Soc. 43, 472 (1883); Hill et al., J. Am. Chem. Soc. 56, 2736 (1934). Mixture of 4 catechols, 3 of which have unsaturated side chains, one of which is 3-(8-pentadecenyl)catechol; the fourth is 3-n-pentadecylcatechol. Component identification: Majima et al., Ber. 55, 172 (1922); Corbett, Billets, J. Pharm. Sci. 64, 1715 (1975). Urushiol from T. verniciferum is a mixture of I-IV and urushiol from T. radicans is a mixture of I, II, III, and V: Symes, Dawson, J. Am. Chem. Soc. 76, 2959 (1954); Sunthankar, Dawson, ibid. 76, 5070 (1954). Separation of components: Markiewitz, Dawson, J. Org. Chem. 30, 1610 (1965). Structural characterization of urushiol from T. diversilobum: Corbett, Billets, loc. cit. Separation of urushiol congeners: C. Y. Ma et al., J. Chromatogr. 200, 163 (1980). Isoln of pure urushiol from poison ivy or oak extracts and separation of congeners by reversed phase chromatography: M. A. El Sohly et al., J. Nat. Prod. 45, 532 (1982). Allergenic properties of congeners: E. S. Watson et al., J. Pharm. Sci. 70, 785 (1981). Review of extraction and compositional analysis: J. H. P. Tyman, Chem. Soc. Rev. 8, 499 (1979).
Properties: Pale yellow liq; d421.5 0.9687; bp 200-210°. Soluble in alcohol, ether, benzene. Moderately sol in petr ether.
Boiling point: bp 200-210°
Density: d421.5 0.9687
CAUTION: An extremely active allergen causing skin reactions similar to poison ivy.
Therap-Cat: Antiallergic (hyposensitization therapy).
Keywords: Antiallergic (Hyposensitization Therapy).

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