Saturated analogs of poison ivy allergens. Synthesis of trans,trans- and cis,trans-3-alkyl-1,2-cyclohexanediols and sensitizing properties in allergic contact dermatitis
- 1 February 1986
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 29 (2) , 287-291
- https://doi.org/10.1021/jm00152a018
Abstract
Saturated analogues of poison ivy and oak allergens (3-alkylcatechols), i.e. trans,trans-3-alkyl-1,2-cyclohexanediols (alkyl = CH3, n-C5H11, n-C10H21, n-C15H31), have been prepared and used to sensitize guinea pigs. Only long-chain derivatives (carbon chain length > C10) are contact sensitizers. The sensitized animals cross-react to PDC (i.e. pentadecylcatechol, one of the allergens of poison ivy), but the converse is not true (PDC-sensitized animals do not react to cyclohexanediols). cis,trans-3-n-Pentadecyl-1,2-cyclohexanediol has also been synthesized and shown to be a sensitizer. There is not cross-reaction between trans,trans- and cis,trans-3-n-pentadecylcyclohexanediols, excluding a common skin metabolite.This publication has 10 references indexed in Scilit:
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