Sköld Maria, Börje Anna, Matura Mihaly, Karlberg Ann-Therese
Occupational Dermatology, National Institute for Working Life, Stockholm, Sweden.
Contact Dermatitis. 2002 May;46(5):267-72. doi: 10.1034/j.1600-0536.2002.460504.x.
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.
香料是过敏性接触性皮炎最常见的病因之一。两种单萜类化合物芳樟醇和d-柠檬烯是香薰产品中最常添加的香料成分。先前对d-柠檬烯的研究表明，这种单萜类化合物在暴露于空气中时会发生氧化（自动氧化）并形成致敏性氧化产物。由于结构相似，芳樟醇在暴露于空气中时也可能形成致敏性氧化产物。本研究的目的是研究芳樟醇的自动氧化，并调查暴露于空气前后芳樟醇的致敏潜力。芳樟醇氧化10周后，气相色谱分析表明芳樟醇含量降至约80%。色谱图显示氧化过程中形成了其他化合物。其中一种主要氧化产物被分离出来并鉴定为7-氢过氧基-3,7-二甲基-辛-1,5-二烯-3-醇。据我们所知，该物质首次被描述。在豚鼠致敏研究中，高纯度芳樟醇未引起反应，而氧化10周的芳樟醇使动物致敏。研究得出结论，芳樟醇的自动氧化对其致敏潜力至关重要。
