Allergenic .alpha.-methylene-.gamma.-butyrolactones. Study of the capacity of .beta.-acetoxy- and .beta.-hydroxy-.alpha.-methylene-.gamma.-butyrolactones to induce allergic contact dermatitis in guinea pigs

1 May 1986

journal article
research article
Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry

Vol. 29 (5) , 868-871
https://doi.org/10.1021/jm00155a046

Abstract

(.+-.)-Tulipalin B was prepared in six steps from phenyl sulfide and ethyl 2-bromopropionate. The sensitizing power in the skin of (.+-.)-tulipalin A (1a) and B (1b) and of the .beta.-acetoxy derivatives (1c) was studied. All are able to induce allergic contact dermatitis (ACD) and give cross-reactions. .gamma.,.gamma.-Disubstituted analogues (with a -(CH2)5- chain in the .gamma.-position) were synthesized and used to induce ACD in guinea pigs: they all were sensitizers and cross-reacted. However, no cross-reaction was demonstrated between .gamma.,.gamma.-unsubstituted and .gamma.,.gamma.-substituted compounds showing a great specificity of ACD.

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