Studies on the autoxidation and sensitizing capacity of the fragrance chemical linalool, identifying a linalool hydroperoxide.
Fragrances are among the most common causes of allergic contact dermatitis. The two monoterpenes linalool and d-limonene are the most frequently incorporated fragrance chemicals in scented products. Previous studies on d-limonene show that this monoterpene oxidizes on air exposure (autoxidation) and that allergenic oxidation products are formed. Due to structural similarities, linalool might also form allergenic oxidation products on air exposure. The aim of the present study was to study the autoxidation of linalool and to investigate the sensitizing potential of linalool before and after air exposure. Linalool was oxidized for 10 weeks and gas chromatographic analyses showed that the content of linalool decreased to about 80%. The chromatograms revealed the formation of other compounds during oxidation. One of the major oxidation products was isolated and identified as 7-hydroperoxy-3,7-dimethyl-octa-1,5-diene-3-ol. This substance is, to the best of our knowledge, described for the first time. In sensitization studies in guinea pigs, linalool of high purity gave no reactions, while linalool that had been oxidized for 10 weeks sensitized the animals. It is concluded that autoxidation of linalool is essential for its sensitizing potential.
Sköld
Maria
M
Occupational Dermatology, National Institute for Working Life, Stockholm, Sweden.
Börje
Anna
A
Matura
Mihaly
M
Karlberg
Ann-Therese
AT
D000080462:Acyclic Monoterpenes; D000818:Animals; D002849:Chromatography, Gas; D017449:Dermatitis, Allergic Contact / Q000209:etiology*; D006168:Guinea Pigs; D039821:Monoterpenes; D010476:Perfume / Q000009:adverse effects / Q000737:chemistry*; D013729:Terpenes / Q000009:adverse effects / Q000737:chemistry*
D000080462:Acyclic Monoterpenes; D039821:Monoterpenes; D010476:Perfume; D013729:Terpenes; C018584:linalool