3-Pentadecylcatechol
Title: 3-Pentadecylcatechol
CAS Registry Number: 492-89-7
CAS Name: 3-Pentadecyl-1,2-benzenediol
Additional Names: 3-pentadecylpyrocatechol; tetrahydrourushiol; hydrourushiol; dihydrorhengol; 3-PDC
Molecular Formula: C21H36O2
Molecular Weight: 320.51
Percent Composition: C 78.69%, H 11.32%, O 9.98%
Literature References: Constituent of the irritant oil of poison ivy (Toxicodendron radicans (L.) Kuntze) and other Toxicodendron spp. (Anacardiaceae). Prepn by hydrogenation of extracts from fruits of Semecarpus heterophylla: Backer, Haack, Rec. Trav. Chim. 57, 225 (1938). Synthesis from 2,3-dimethoxybenzaldehyde and tetradecyl chloride: Mason, J. Am. Chem. Soc. 67, 1538 (1945); from o-veratraldehyde: Backer, Haack, loc. cit.; Dawson et al., J. Am. Chem. Soc. 68, 534 (1946); Keil et al., US 2451955 (1948); from 2,3-dibenzyloxybenzaldehyde: Loev, Dawson, J. Org. Chem. 24, 980 (1959); from furan derivs: Boehme, J. Am. Chem. Soc. 82, 499 (1960); from catechol: Hanafusa, Yukawa, Chem. Ind. (London) 1961, 23. Criticism of reported syntheses and synthesis of dimethyl deriv: Byck, Dawson, J. Org. Chem. 32, 1084 (1967). Total synthesis: E. Wenkert et al., J. Am. Chem. Soc. 105, 2021 (1983). Evaluation of diagnostic patch test: M. V. Dahl et al., Arch. Dermatol. 120, 1022 (1984).
Properties: Short needles from toluene or petr ether, mp 59-60°. Can be purified by molecular distn. uv max: 277 nm. Sol in alc, ether, benzene, toluene. Sparingly sol in petr ether.
Melting point: mp 59-60°
Absorption maximum: uv max: 277 nm
Therap-Cat: Diagnostic aid (contact allergen).
Keywords: Diagnostic Aid.

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