Saturated analogues of poison ivy allergens. Synthesis of trans,trans- and cis,trans-3-alkyl-1,2-cyclohexanediols and sensitizing properties in allergic contact dermatitis.
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 greater than 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.
D000485:Allergens / Q000633:toxicity*; D000818:Animals; D002396:Catechols / Q000138:chemical synthesis* / Q000276:immunology / Q000633:toxicity; D003429:Cross Reactions; D003511:Cyclohexanols / Q000138:chemical synthesis* / Q000633:toxicity; D011040:Dermatitis, Toxicodendron / Q000209:etiology*; D005260:Female; D006168:Guinea Pigs; D013329:Structure-Activity Relationship
D000485:Allergens; D002396:Catechols; D003511:Cyclohexanols; C003747:urushiol