The fragrance chemical beta-caryophyllene-air oxidation and skin sensitization.

Sköld, Maria,1976Gothenburg University,Göteborgs universitet,Institutionen för kemi,Department of Chemistry (author)

Fragrances are common causes of allergic contact dermatitis. beta-Caryophyllene is a sesquiterpene that is used as a fragrance chemical. Analogous to the monoterpenes R-limonene and linalool, it can be expected to autoxidize when air exposed. The aim of the present study was to investigate the autoxidation of beta-caryophyllene and to evaluate the effect on the contact allergenic activity. beta-Caryophyllene started to oxidize immediately when air exposed and after 5 weeks almost 50% of the original compound was consumed. Caryophyllene oxide was found to be the major oxidation product. Hydroperoxides of beta-caryophyllene could not be detected in the oxidation mixture. Caryophyllene oxide was shown to be an allergen of moderate strength and beta-caryophyllene air exposed for 10 weeks showed a weak sensitizing capacity in the local lymph node assay. The study reveals that the allergenic activity of beta-caryophyllene is affected by autoxidation, but to a lesser extent when compared to R-limonene and linalool. The present findings support our results in clinical studies showing oxidized beta-caryophyllene to be a rather rare sensitizer compared to oxidized R-limonene and linalool.

MEDICIN OCH HÄLSOVETENSKAP Medicinska och farmaceutiska grundvetenskaper Läkemedelskemi hsv//swe
MEDICAL AND HEALTH SCIENCES Basic Medicine Medicinal Chemistry hsv//eng
Air
Animals
Dermatitis
Contact
etiology
pathology
Female
Guinea Pigs
Mice
Mice
Inbred CBA
Oxidation-Reduction
Perfume
adverse effects
chemistry
Sesquiterpenes
adverse effects
chemistry

Karlberg, Ann-Therese,1947Gothenburg University,Göteborgs universitet,Institutionen för kemi,Department of Chemistry(Swepub:gu)xkaann (author)
Matura, Mihaly,1964Gothenburg University,Göteborgs universitet,Institutionen för kemi,Department of Chemistry(Swepub:gu)xmatmi (author)
Börje, Anna,1961Gothenburg University,Göteborgs universitet,Institutionen för kemi,Department of Chemistry(Swepub:gu)xboann (author)
Göteborgs universitetInstitutionen för kemi (creator_code:org_t)

In:Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association: Elsevier BV44:4, s. 538-450278-6915

By the author/editor: Sköld, Maria, 19 ...; Karlberg, Ann-Th ...; Matura, Mihaly, ...; Börje, Anna, 196 ...

About the subject

MEDICAL AND HEALTH SCIENCES: MEDICAL AND HEAL ...; and Basic Medicine; and Medicinal Chemis ...

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