Chromatographic analyses and unambiguous identification of atranol‐like secondary metabolites in oakmoss absolute,Flavour and Fragrance Journal

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Chromatographic analyses and unambiguous identification of atranol‐like secondary metabolites in oakmoss absolute
Flavour and Fragrance Journal ( IF 2.1 ) Pub Date : 2020-04-29 , DOI: 10.1002/ffj.3578
Amar G. Chittiboyina ₁ , Mei Wang ₁ , Cristina Avonto ₁ , Jon F. Parcher ₁ , Ikhlas A. Khan _{1,

2}

Affiliation

Oakmoss is a commercially significant natural extract used in exotic perfumes, cosmetics, and other personal care products. Unfortunately, oakmoss absolutes and oils also contain atranol and chloroatranols, well‐known potent skin sensitizers, and hence, their levels in personal care products are regulated. To address the presence of these metabolites and unravel the similar metabolites in the oakmoss absolute, two independent analytical methods were developed. As a proof of concept, one commercial absolute oakmoss was analyzed with complementary, orthogonal LC/MS, GC/MS methods and further confirmed with MS² experiments. Sixteen secondary metabolites, including atranols, were identified by both GC and LC analyses. Many of the identified components appear to be the precursors of the atranols or process artifacts. One atranol analog, in particular, isopropyl haematommate, was investigated extensively with electron ionization mass spectrometry to show that fragmentation spectra can be applied for the unambiguous identification of related compounds. An intriguing fragmentation pattern was observed for a typical α‐hydroxybenzoate, involving sequential loss of alkene, alkanol, water, or carbon monoxide. A similar fragmentation pattern has been observed with ESI; however, the loss of CO₂ was dominant, while the loss of CO was most commonly observed with the EI system independent of substituents on the aromatic ring. The identification of these metabolites was further confirmed with pure standards. Even though many of these unique secondary metabolites are structurally similar to atranols, their skin sensitization potential is unknown; hence, the developed methods can serve as an effective tool to assess the overall quality of various oakmoss‐based products.

中文翻译：

橡苔绝对色谱中层析形式的分析和气溶胶类次生代谢产物的明确鉴定

Oakmoss是商业上重要的天然提取物，用于异国情调的香水，化妆品和其他个人护理产品中。不幸的是，oakmoss净油和油脂中也含有众所周知的强效皮肤敏化剂atranol和chloroatranol，因此，它们在个人护理产品中的含量受到监管。为了解决这些代谢物的存在并阐明橡苔绝对物中的类似代谢物，开发了两种独立的分析方法。作为概念证明，使用互补的正交LC / MS，GC / MS方法分析了一种市售的绝对橡苔，并用MS ²进一步证实实验。GC和LC分析均鉴定出16种次级代谢产物，包括阿糖酚。许多已鉴定出的成分似乎是戊醇或工艺制品的前体。用电子电离质谱法广泛研究了一种芳香醇类似物，特别是异丙基血原子异氰酸酯，以显示碎片光谱可用于相关化合物的明确鉴定。对于典型的α-羟基苯甲酸酯，观察到了一个令人着迷的碎裂模式，涉及烯烃，链烷醇，水或一氧化碳的连续损失。使用ESI观察到了类似的碎片模式。但是，CO ₂的损失占主导地位，而最常见的是EI系统不依赖于芳环上取代基的情况下，CO的损失。用纯标准品进一步证实了这些代谢物的鉴定。尽管许多独特的次级代谢产物在结构上与阿糖醇相似，但它们的皮肤致敏潜能尚不明确。因此，开发的方法可以作为评估各种基于橡苔产品的整体质量的有效工具。

更新日期：2020-04-29

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