92210-70-3Relevant academic research and scientific papers
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
Lepoittevin,Benezra
, p. 287 - 291 (2007/10/02)
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.
CYCLOHEXANE ANALOGS OF POISON IVY AND POISON OAK DERIVATIVES. A TOTALLY STEREOSELECTIVE SYNTHESIS OF TRANS,TRANS-3-ALKYL-1,2-CYCLOHEXANEDIOLS.
Lepoittevin, Jean-Pierre,Benezra, Claude
, p. 2505 - 2506 (2007/10/02)
Pure trans,trans-3-methyl-, 3-n-pentyl-, 3-n-decyl- and 3-n-pentadecyl-1,2-cyclohexanediols have been prepared in two steps, in 55-70percent overall yields from 2-cyclohexenone.
