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.
(+/-)-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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Barbier
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Benezra
D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D000818:Animals; D003877:Dermatitis, Contact / Q000209:etiology*; D005260:Female; D005663:Furans / Q000138:chemical synthesis*; D006168:Guinea Pigs
D005663:Furans; C048810:tulipalin B; C014096:alpha-methylene gamma-butyrolactone; D015107:4-Butyrolactone