Archives of Dermatological Research

, Volume 286, Issue 2, pp 97–103

Hydroperoxides in oxidized d-limonene identified as potent contact allergens

Authors

  • A. -T. Karlberg
    • Department of Occupational DermatologyNational Institute of Occupational Health
  • L. P. Shao
    • Department of Pharmaceutical Chemistry, Organic Pharmaceutical ChemistryUppsala University
  • U. Nilsson
    • Department of Analytical ChemistryNational Institute of Occupational Health
  • E. GÄfvert
    • Department of Occupational DermatologyNational Institute of Occupational Health
  • J. L. G. Nilsson
    • Department of Pharmaceutical Chemistry, Organic Pharmaceutical ChemistryUppsala University
Original Contributions

DOI: 10.1007/BF00370734

Cite this article as:
Karlberg, A.-., Shao, L.P., Nilsson, U. et al. Arch Dermatol Res (1994) 286: 97. doi:10.1007/BF00370734

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 photooxidized 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.

Key words

Contact allergyHydroperoxidesd-LimoneneMass spectrometryLimonene synthesis
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Copyright information

© Springer-Verlag 1994