35154-49-5

Upstream product

• 1192-78-5 (1R*,2R*,3S*)-2,3-epoxycyclohexanol 
• 78887-70-4 pentadecylmagnesium bromide 
• 52189-71-6 pentadecyllithium 
• 930-68-7 cyclohexenone 
• 92210-71-4 3-pentadecyl-1-<(trimethylsilyl)oxy>cyclohexene 

Relevant academic research and scientific papers

Synthesis of a Model Hapten with Cyclohexanediol and &α-Methylene-&γ-butyrolactone Groups, a Synthetic Analogue of Poison Ivy and Tulipalin Allergens Connected with a Carbon Chain

Potential skin sensitizers 1 and 1* with two different haptenic ends, (a) a cyclohexanediol group (saturated poison ivy analogue ) and (b) an α-methylene-γ-butyrolactone moiety (tulipalin A), separated by a nine carbon atoms chain containing a double bond have been prepared.The trans, trans relationship in the substituted cyclohexanediol was secured by a tandem Michael addition-hydroboration reaction.Contrary to an earlier example of a double-headed hapten containing pyrocatechol and α-methylene-γ-butyrolactone ends, the cyclohexanediol-α-methylene-γ-butyrolactone does not show any tolerance induction to the α-methylene-γ-butyrolactone end.It therefore seems that induction of tolerance as well as sensitization requires the formation of covalent bond with a protein carrier.

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 > 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.

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.