Department of Chemistry and Molecular Biology, Dermatochemistry and Skin Allergy, University of Gothenburg, 412 96, Gothenburg, Sweden.
Contact Dermatitis. 2014 Jun;70(6):329-39. doi: 10.1111/cod.12234. Epub 2014 Mar 27.
Citronellol is a frequently used fragrance compound in consumer products. It is present in fragrance mix II, which is used for screening of contact allergy to fragrances. Because of its chemical structure, citronellol could be susceptible to autoxidation.
To compare the behaviour of citronellol with that of the structurally similar compounds linalool and geraniol, in terms of ability to autoxidize, the products formed, and the sensitization potencies of these.
Citronellol was exposed to air, and autoxidation was followed by gas chromatography-mass spectrometry (GC-MS) analysis after derivatization of thermolabile compounds. The sensitizing potencies of the oxidation mixture and its major oxidation compounds were examined with the local lymph node assay.
The concentration of citronellol decreased while the sensitization potency increased in air-exposed samples over time, with hydroperoxides being identified as the major oxidation products and main skin sensitizers.
The present study shows the impact of the absence of the 2,3-double bond in the citronellol structure on the oxidation pathways for formation of oxidation products. The study also shows the usefulness of our new GC-MS method for quantification of the citronellol oxidation products, especially the hydroperoxides. The investigated citronellol hydroperoxides could be important allergens, owing to the high concentrations detected and frequent exposure to citronellol in the population.
香茅醇是一种常用于消费品的香料化合物。它存在于香料混合物 II 中，用于筛查对香料的接触过敏。由于其化学结构，香茅醇可能容易自动氧化。
比较香茅醇与结构相似的化合物芳樟醇和香叶醇的行为，包括自动氧化能力、形成的产物以及这些产物的致敏潜力。
将香茅醇暴露于空气中，并在热不稳定化合物衍生化后通过气相色谱-质谱（GC-MS）分析来跟踪自动氧化。使用局部淋巴结测定法检查氧化混合物及其主要氧化化合物的致敏潜力。
随着时间的推移，在空气中暴露的样品中，香茅醇的浓度降低，而致敏能力增加，鉴定出氢过氧化物是主要的氧化产物和主要的皮肤致敏剂。
本研究表明了香茅醇结构中缺乏 2,3-双键对形成氧化产物的氧化途径的影响。该研究还表明了我们新的 GC-MS 方法用于定量香茅醇氧化产物的有用性，特别是氢过氧化物。研究中发现的香茅醇氢过氧化物可能是重要的过敏原，因为检测到的浓度很高，而且人群中经常接触香茅醇。
