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Cinnamyl alcohol oxidizes rapidly upon air exposure

Niklasson, Ida B, 1982 (author)
Gothenburg University,Göteborgs universitet,Institutionen för kemi och molekylärbiologi,Department of Chemistry and Molecular Biology
Delaine, Tamara, 1981 (author)
Gothenburg University,Göteborgs universitet,Institutionen för kemi och molekylärbiologi,Department of Chemistry and Molecular Biology
Nurul, Islam (author)
Gothenburg University,Göteborgs universitet,Institutionen för kemi och molekylärbiologi,Department of Chemistry and Molecular Biology
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Karlsson, Roger, 1975 (author)
Gothenburg University,Göteborgs universitet,Institutionen för kemi och molekylärbiologi,Department of Chemistry and Molecular Biology
Luthman, Kristina, 1953 (author)
Gothenburg University,Göteborgs universitet,Institutionen för kemi och molekylärbiologi,Department of Chemistry and Molecular Biology
Karlberg, Ann-Therese, 1947 (author)
Gothenburg University,Göteborgs universitet,Institutionen för kemi och molekylärbiologi,Department of Chemistry and Molecular Biology
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 (creator_code:org_t)
2013-02-19
2013
English.
In: Contact Dermatitis. - : Wiley. - 0105-1873 .- 1600-0536. ; 68:3, s. 129-138
  • Journal article (peer-reviewed)
Abstract Subject headings
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  • Background. Cinnamyl alcohol and cinnamal are frequent fragrance contact allergens. Both are included in the European baseline fragrance mix I, which is used for screening of contact allergy in dermatitis patients. Objectives. The aim of this study was to investigate the autoxidation of cinnamyl alcoholandtoidentifytheoxidationproductsformedonairexposure.Wealsowantedto evaluate the effect of autoxidation on the sensitization potency of cinnamyl alcohol. Methods. Samples of commercially available cinnamyl alcohol with and without purificationwereexposedtoair,andtheautoxidationwasfollowedbychemicalanalysis. Theanalysiswasperformedwithmassspectrometry(LC/MS/MS).Sensitizationpotencies ofcompoundsweredeterminedwiththemurinelocallymphnodeassay(LLNA)inmice. Results. Chemical analysis showed that the concentration of cinnamyl alcohol in the air-exposed samples decreased rapidly over time, and that autoxidation products were formed. Cinnamal, epoxy cinnamyl alcohol and cinnamic acid were identified as oxidation products. According to our study, cinnamal and epoxy cinnamyl alcohol were thefirstautoxidation productsformed. Theepoxy cinnamyl alcohol wasshowntobethe oxidation product with the highest sensitization potency. The analysis of our samples of commercially available cinnamyl alcohol showed that there was already a content of 1.5% cinnamal at the start of the autoxidation experiments. Conclusion. Cinnamylalcoholreadilyautoxidizesuponairexposure,andformsstrong sensitizers as determined by the LLNA. Cinnamal was formed in the largest amounts, showingthatcinnamalisnotonlyformedviabioactivation,ashaspreviouslybeenshown. A highly sensitizing epoxide was also identified and quantified in the oxidation mixture.

Subject headings

NATURVETENSKAP  -- Kemi -- Organisk kemi (hsv//swe)
NATURAL SCIENCES  -- Chemical Sciences -- Organic Chemistry (hsv//eng)

Publication and Content Type

ref (subject category)
art (subject category)

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