PMID- 18154552
OWN - NLM
STAT- MEDLINE
DCOM- 20080221
LR  - 20211203
IS  - 1600-0536 (Electronic)
IS  - 0105-1873 (Linking)
VI  - 58
IP  - 1
DP  - 2008 Jan
TI  - Autoxidation of linalyl acetate, the main component of lavender oil, creates 
      potent contact allergens.
PG  - 9-14
AB  - BACKGROUND: Fragrances are among the most common causes of allergic contact 
      dermatitis. We have in previous studies shown that linalool, present in lavender 
      oil, autoxidizes on air exposure, forming allergenic oxidation products. Oxidized 
      linalool was found to be a frequent cause of contact allergy in a patch test 
      study on consecutive dermatitis patients. Linalyl acetate, the main component of 
      lavender oil is commonly used as a fragrance chemical in scented products. 
      Because of structural similarities, linalyl acetate should also be susceptible to 
      oxidation on air exposure, forming similar oxidation products as linalool. 
      OBJECTIVE: The aim of the present study was to investigate the autoxidation of 
      linalyl acetate and the influence of oxidation on its sensitizing potency. 
      METHODS: Analyses were performed using gas chromatography, nuclear magnetic 
      resonance spectrometry and mass spectrometry. Sensitizing potencies of compounds 
      were determined using the local lymph node assay (LLNA) in mice. RESULTS: 
      Analyses showed that the content of linalyl acetate decreased over time on air 
      exposure and other compounds were formed. Hydroperoxides, an epoxide and an 
      alcohol were identified as oxidation products from linalyl acetate. In the LLNA, 
      linalyl acetate of high purity showed a weak sensitizing potency (EC3 25%). 
      Autoxidation increased the sensitizing potency of linalyl acetate, and a 10 weeks 
      oxidized sample gave an EC3 value of 3.6%. As for linalool, the hydroperoxides 
      were shown to be the oxidation products with the highest sensitizing potency. 
      CONCLUSION: It is concluded that autoxidation of the weakly allergenic linalyl 
      acetate leads to formation of allergenic oxidation products.
FAU - Skold, Maria
AU  - Skold M
AD  - Department of Chemistry, Dermatochemistry and Skin Allergy, Goteborg University, 
      SE-412 96 Goteborg, Sweden.
FAU - Hagvall, Lina
AU  - Hagvall L
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 (Monoterpenes)
RN  - 0 (Oils, Volatile)
RN  - 0 (Plant Oils)
RN  - 5K47SSQ51G (linalyl acetate)
RN  - BBX060AN9V (Hydrogen Peroxide)
RN  - ZBP1YXW0H8 (lavender oil)
SB  - IM
MH  - Air
MH  - Allergens/adverse effects/chemistry/*metabolism
MH  - Animals
MH  - Chromatography, Gas
MH  - Dermatitis, Allergic Contact/etiology/immunology
MH  - Hydrogen Peroxide/adverse effects/chemistry/*metabolism
MH  - Lavandula
MH  - Lymph Nodes/immunology
MH  - Magnetic Resonance Spectroscopy
MH  - Mass Spectrometry
MH  - Mice
MH  - Monoterpenes/adverse effects/chemistry/*metabolism
MH  - Oils, Volatile/adverse effects/chemistry
MH  - Oxidation-Reduction
MH  - Plant Oils/adverse effects/chemistry
MH  - Skin/immunology
MH  - Time Factors
EDAT- 2007/12/25 09:00
MHDA- 2008/02/22 09:00
CRDT- 2007/12/25 09:00
PHST- 2007/12/25 09:00 [pubmed]
PHST- 2008/02/22 09:00 [medline]
PHST- 2007/12/25 09:00 [entrez]
AID - COD1262 [pii]
AID - 10.1111/j.1600-0536.2007.01262.x [doi]
PST - ppublish
SO  - Contact Dermatitis. 2008 Jan;58(1):9-14. doi: 10.1111/j.1600-0536.2007.01262.x.