PMID- 23421457
OWN - NLM
STAT- MEDLINE
DCOM- 20130809
LR  - 20210702
IS  - 1600-0536 (Electronic)
IS  - 0105-1873 (Linking)
VI  - 68
IP  - 3
DP  - 2013 Mar
TI  - Cinnamyl alcohol oxidizes rapidly upon air exposure.
PG  - 129-38
LID - 10.1111/cod.12009 [doi]
AB  - 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 alcohol and to 
      identify the oxidation products formed on air exposure. We also wanted to 
      evaluate the effect of autoxidation on the sensitization potency of cinnamyl 
      alcohol. METHODS: Samples of commercially available cinnamyl alcohol with and 
      without purification were exposed to air, and the autoxidation was followed by 
      chemical analysis. The analysis was performed with mass spectrometry (LC/MS/MS). 
      Sensitization potencies of compounds were determined with the murine local lymph 
      node assay (LLNA) in mice. 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 the first autoxidation products 
      formed. The epoxy cinnamyl alcohol was shown to be the 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: Cinnamyl 
      alcohol readily autoxidizes upon air exposure, and forms strong sensitizers as 
      determined by the LLNA. Cinnamal was formed in the largest amounts, showing that 
      cinnamal is not only formed via bioactivation, as has previously been shown. A 
      highly sensitizing epoxide was also identified and quantified in the oxidation 
      mixture.
CI  - (c) 2013 John Wiley & Sons A/S.
FAU - Niklasson, Ida B
AU  - Niklasson IB
AD  - Department of Chemistry and Molecular Biology, Dermatochemistry and Skin Allergy, 
      University of Gothenburg, SE-412 96 Gothenburg, Sweden.
FAU - Delaine, Tamara
AU  - Delaine T
FAU - Islam, M Nurul
AU  - Islam MN
FAU - Karlsson, Roger
AU  - Karlsson R
FAU - Luthman, Kristina
AU  - Luthman K
FAU - Karlberg, Ann-Therese
AU  - Karlberg AT
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
PL  - England
TA  - Contact Dermatitis
JT  - Contact dermatitis
JID - 7604950
RN  - 0 (Allergens)
RN  - 0 (Cinnamates)
RN  - 0 (Epoxy Compounds)
RN  - 0 (Propanols)
RN  - 140-10-3 (cinnamic acid)
RN  - 7864XYD3JJ (Acrolein)
RN  - SR60A3XG0F (cinnamaldehyde)
RN  - SS8YOP444F (cinnamyl alcohol)
SB  - IM
MH  - Acrolein/analogs & derivatives/chemistry/immunology/metabolism
MH  - *Air
MH  - Allergens/*chemistry/immunology/metabolism
MH  - Animals
MH  - Chromatography, High Pressure Liquid
MH  - Cinnamates/chemistry/immunology/metabolism
MH  - Epoxy Compounds/chemistry/immunology/metabolism
MH  - Gas Chromatography-Mass Spectrometry
MH  - Local Lymph Node Assay
MH  - Magnetic Resonance Spectroscopy
MH  - Mice
MH  - *Oxidation-Reduction
MH  - Propanols/*chemistry/immunology/metabolism
EDAT- 2013/02/21 06:00
MHDA- 2013/08/10 06:00
CRDT- 2013/02/21 06:00
PHST- 2013/02/21 06:00 [entrez]
PHST- 2013/02/21 06:00 [pubmed]
PHST- 2013/08/10 06:00 [medline]
AID - 10.1111/cod.12009 [doi]
PST - ppublish
SO  - Contact Dermatitis. 2013 Mar;68(3):129-38. doi: 10.1111/cod.12009.