Hydroperoxides in oxidized d-limonene identified as potent contact allergens.

Abstract:

:Hydroperoxides of d-limonene were shown to be potent contact allergens when studied in guinea-pigs. Limonene-2-hydroperoxide (2-hydroperoxy-p-mentha-6,8-diene, a mixture of trans and cis isomers) was synthesized for the first time. The ratio between the trans and cis forms was 3:1. These two hydroperoxides were identified as the major hydroperoxides in autoxidized d-limonene. In photo-oxidized d-limonene, they constituted a minor part of the hydroperoxide fraction. Hydroperoxides may bind to proteins of the skin to make antigens either via a radical mechanism or after reactions to give epoxides. The cross-reactivity between the epoxide limonene-1,2-oxide, a potent contact allergen, and the hydroperoxides was therefore studied. No significant pattern of cross-reactivity was found. Further studies to identify and test the allergenicity of single hydroperoxides are needed to elucidate the mechanism of the allergenicity.

journal_name

Arch Dermatol Res

authors

Karlberg AT,Shao LP,Nilsson U,Gäfvert E,Nilsson JL

doi

10.1007/BF00370734

subject

Has Abstract

pub_date

1994-01-01 00:00:00

pages

97-103

issue

2

eissn

0340-3696

issn

1432-069X

journal_volume

286

pub_type

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