PMID- 15606147
OWN - NLM
STAT- MEDLINE
DCOM- 20050614
LR  - 20191210
IS  - 0893-228X (Print)
IS  - 0893-228X (Linking)
VI  - 17
IP  - 12
DP  - 2004 Dec
TI  - Contact allergens formed on air exposure of linalool. Identification and 
      quantification of primary and secondary oxidation products and the effect on skin 
      sensitization.
PG  - 1697-705
AB  - Linalool (3,7-dimethyl-1,6-octadien-3-ol) is an important fragrance chemical, 
      frequently used in scented products because of its fresh, flowery odor. Linalool 
      is an unsaturated hydrocarbon and is therefore susceptible to oxidation in the 
      presence of air. The primary oxidation products, that is, hydroperoxides, formed 
      in the autoxidation process, are reactive compounds that can be suspected to act 
      as sensitizers. In the present investigation, we studied the autoxidation of 
      linalool with emphasis on the formation of hydroperoxides. The oxidation products 
      were isolated using flash chromatography and preparative HPLC and were identified 
      with NMR and GC/MS, using synthesized reference compounds. Two hydroperoxides and 
      several different secondary oxidation products were identified, among which some 
      contain structural features that make them potential allergens. The amounts of 
      linalool and the major oxidation products were quantified over time, using GC and 
      an HPLC-method, suitable for the analysis of thermolabile primary oxidation 
      products. The hydroperoxide 7-hydroperoxy-3,7-dimethylocta-1,5-diene-3-ol was 
      found to be present in 15% in an oxidized sample. The local lymph node assay 
      (LLNA) was used to investigate the sensitizing potential of pure linalool, two 
      samples of air-exposed linalool, and oxidation products of linalool (an 
      alpha,beta-unsaturated aldehyde, a mixture of two hydroperoxides, and an 
      alcohol). Pure linalool showed no sensitizing potential. The air-exposed samples 
      of linalool produced clearly positive responses, and the hydroperoxides were the 
      strongest allergens of the tested oxidation products. The study demonstrates the 
      importance of autoxidation on the sensitizing potential of linalool. We also 
      conclude that the sensitizing potential differs with the composition of the 
      oxidation mixture and thus with the air exposure time.
FAU - Skold, Maria
AU  - Skold M
AD  - Department of Chemistry, Dermatochemistry and Skin Allergy, Goteborg University, 
      SE-412 96 Goteborg, Sweden.
FAU - Borje, Anna
AU  - Borje A
FAU - Harambasic, Elma
AU  - Harambasic E
FAU - Karlberg, Ann-Therese
AU  - Karlberg AT
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
PL  - United States
TA  - Chem Res Toxicol
JT  - Chemical research in toxicology
JID - 8807448
RN  - 0 (Acyclic Monoterpenes)
RN  - 0 (Allergens)
RN  - 0 (Monoterpenes)
RN  - 0 (Perfume)
RN  - BBX060AN9V (Hydrogen Peroxide)
RN  - D81QY6I88E (linalool)
SB  - IM
MH  - Acyclic Monoterpenes
MH  - Allergens/*chemistry/immunology
MH  - Chromatography, High Pressure Liquid
MH  - Dermatitis, Allergic Contact/*immunology
MH  - Humans
MH  - Hydrogen Peroxide/*analysis
MH  - Local Lymph Node Assay
MH  - Monoterpenes/*chemistry/*immunology/metabolism
MH  - Oxidation-Reduction
MH  - Perfume/chemistry
MH  - Time Factors
EDAT- 2004/12/21 09:00
MHDA- 2005/06/15 09:00
CRDT- 2004/12/21 09:00
PHST- 2004/12/21 09:00 [pubmed]
PHST- 2005/06/15 09:00 [medline]
PHST- 2004/12/21 09:00 [entrez]
AID - 10.1021/tx049831z [doi]
PST - ppublish
SO  - Chem Res Toxicol. 2004 Dec;17(12):1697-705. doi: 10.1021/tx049831z.