Fixative effect of 2-oxo-2-phenylacetates in fine fragrance and eau-de-toilette applications

IF 2.1 3区 农林科学 Q3 CHEMISTRY, APPLIED
Damien L. Berthier, Jérôme Girard, Katharina M. Fromm, Andreas Herrmann
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Abstract

The evaporation of fragrances with volatilities spanning over several orders of magnitude results in a shift of the olfactive impression of a perfume over time. Fixatives have repeatedly been used to slow fragrance evaporation in multiple perfumery applications. We developed a simple and reliable method to measure the evaporation kinetics of individual fragrances in a model perfume and analysed the fixative effect of 2-oxo-2-phenylacetates (α-ketoesters) on perfume evaporation. 2-Oxo-2-phenylacetates, some of which have been described as light-sensitive profragrances, are commercially available or readily prepared by esterification or transesterification of commercial starting materials. (−)-Menthyl 2-oxo-2-phenylacetate afforded single crystals that were suitable for X-ray crystal structure analysis. 2-Oxo-2-phenylacetates were found to have a fixative effect on the evaporation of fragrances with volatilities below 5000 μg L−1 in fine fragrance and eau-de-toilette applications. The molecular structure of the compound rather than its molecular weight had an impact on the fixative effect to some extent.

Abstract Image

Abstract Image

2-oxo-2-phenylacetates 在高级香水和花露水应用中的固定效果
随着时间的推移,挥发性跨越几个数量级的香水的蒸发会导致香水的嗅觉印象发生变化。在多种香料应用中,固定剂被反复用于减缓香味蒸发。我们建立了一种简单可靠的方法来测量模型香水中单个香料的蒸发动力学,并分析了2-氧-2-苯乙酸酯(α-酮酯)对香水蒸发的固定作用。2-氧-2-苯乙酸酯,其中一些被描述为光敏芳香剂,是市售的或很容易通过商业原料的酯化或酯交换制备的。(−)-Menthyl 2-oxo-2-phenylacetate提供了适合x射线晶体结构分析的单晶。2-氧-2-苯乙酸酯对挥发性低于5000 μg L−1的香精和洗浴用品的挥发有固定作用。在一定程度上影响固定效果的是化合物的分子结构而不是其分子量。
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来源期刊
Flavour and Fragrance Journal
Flavour and Fragrance Journal 工程技术-食品科技
CiteScore
6.00
自引率
3.80%
发文量
40
审稿时长
1 months
期刊介绍: Flavour and Fragrance Journal publishes original research articles, reviews and special reports on all aspects of flavour and fragrance. Its high scientific standards and international character is ensured by a strict refereeing system and an editorial team representing the multidisciplinary expertise of our field of research. Because analysis is the matter of many submissions and supports the data used in many other domains, a special attention is placed on the quality of analytical techniques. All natural or synthetic products eliciting or influencing a sensory stimulus related to gustation or olfaction are eligible for publication in the Journal. Eligible as well are the techniques related to their preparation, characterization and safety. This notably involves analytical and sensory analysis, physical chemistry, modeling, microbiology – antimicrobial properties, biology, chemosensory perception and legislation. The overall aim is to produce a journal of the highest quality which provides a scientific forum for academia as well as for industry on all aspects of flavors, fragrances and related materials, and which is valued by readers and contributors alike.
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