Integrated comprehensive two-dimensional gas-chromatographic and spectroscopic characterization of vetiveryl acetates: Molecular identifications, quantification of constituents, regulatory and olfactory considerations

Tissandié, Loïc; Brevard, Hugues; Belhassen, Emilie; Alberola, Marion; Meierhenrich, Uwe J.; Filippi, Jean‐Jacques

doi:10.1016/j.chroma.2018.08.050

Cited by 15 publications

(14 citation statements)

References 41 publications

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“…[248] While khusimyl acetate is the main constituent of vetiveryl acetate,i ts main odor vector was claimed to be norziza-2a-yl acetate (285,F igure 24). [249,250] Recently,t he group of DuÇach [251] reported on the vetiver-scented spiroxides 286 and 287,d erived from the inexpensive sandalwood building block (R)-campholenal but possessing high odor thresholds of ca. 50 ng L À1 air and 15 ng L À1 air, respectively.…”

Section: Vetiver:f Rom Khusimone To Zizaenonesmentioning

confidence: 99%

What's Hot, What's Not: The Trends of the Past 20 Years in the Chemistry of Odorants

et al. 2020

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This review is the sequel to the 2000 report on the recent advances in the chemistry of odorants and it summarizes the developments in fragrance chemistry over the past 20 years. Following the olfactory spectrum set out in that report, trendsetting so‐called captive odorants (patent‐protected ingredients unavailable to the market) are presented according to the main odor families: “fruity”, “marine”, “green”, “floral”, “spicy”, “woody”, “amber”, and “musky”. The design of odorants, their chemical synthesis, and their use in modern perfumery are illustrated with prominent examples. Featured are new fruity odorants that provide signature in the top note, as well as precursor technology. In the green domain, focus is on leafy notes and green pear. New benzodioxepines and benzodioxoles have modernized the marine family and required a revision of the existing olfactophore models. The replacement of Lilial and Lyral kept the industry busy in the floral domain with a plethora of new “muguets”. There was continued activity in the domain of rose odorants, especially in the area of rose ketones. Biotechnology became significant, for example, with Clearwood and Ambrofix, and the principal odorants of vetiver oil in the woody family have been found. Fourth and fifth families of musk odorants were also discovered and populated. Thus, new avenues for further explorations into fragrance chemistry have been opened.

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Section: Vetiver:f Rom Khusimone To Zizaenonesmentioning

confidence: 99%

What's Hot, What's Not: The Trends of the Past 20 Years in the Chemistry of Odorants

et al. 2020

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“…Tissandie et al . reported a detailed investigation of vetiveryl acetates and vetiver oils and related it to the final olfactory properties [111]. A series of SPE cartridges ( i.e.…”

Section: Non‐targeted Analysis Applicationsmentioning

confidence: 99%

The role of sample preparation in multidimensional gas chromatographic separations for non‐targeted analysis with the focus on recent biomedical, food, and plant applications

Franchina

Zanella

Dubois

et al. 2020

J of Separation Science

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In this review, we consider and discuss the affinity and complementarity between a generic sample preparation technique and the comprehensive two‐dimensional gas chromatography process. From the initial technical development focus (e.g., on the GC×GC and solid‐phase microextraction techniques), the trend is inevitably shifting toward more applied challenges, and therefore, the preparation of the sample should be carefully considered in any GC×GC separation for an overreaching research. We highlight recent biomedical, food, and plant applications (2016–July 2020), and specifically those in which the combination of tailored sample preparation methods and GC×GC–MS has proven to be beneficial in the challenging aspects of non‐targeted analysis. Specifically on the sample preparation, we report on gas‐phase, solid‐phase, and liquid‐phase extractions, and derivatization procedures that have been used to extract and prepare volatile and semi‐volatile metabolites for the successive GC×GC analysis. Moreover, we also present a milestone section reporting the early works that pioneered the combination of sample preparation techniques with GC×GC for non‐targeted analysis.

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“…[248] Während Khusimylacetat der Hauptbestandteil von Vetiverylacetat ist, wird aktuell das Norziza-2a-ylacetat (285,A bbildung 24) als wichtigster Geruchsträger angesehen. [249,250] Kürzlich berichtete die Gruppe von DuÇach [251] über Spiroxide 286 und 287, die nach Vetiver riechen und aus dem preiswerten Sandelholzbaustein (R)-Campholenal zugänglich sind, leider aber recht hohe Schwellenwerte von ca. 50 ng L À1 Luft bzw.…”

Section: Angewandte Chemieunclassified

Heiße Luft oder cooler Duft? Die Trends der letzten 20 Jahre in der Riechstoffchemie

et al. 2020

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Dieser Aufsatz ist die Fortsetzung unseres Berichtes über die neuesten Trends der Riechstoffchemie aus dem Jahr 2000 und fasst die Entwicklungen der letzten 20 Jahren zusammen. Dem selben Duftspektrum folgend, werden besonders richtungsweisende Captives (patentgeschützte Riechstoffe, die nicht frei verkäuflich sind) vorgestellt, und die Einteilung in die Geruchsfamilien “fruchtig”, “grün”, “marin”, “blumig”, “würzig”, “holzig”, “Ambra” und “Moschus” wird auch in dieser Übersicht beibehalten. Das Design von Riechstoffen, ihre chemische Synthese und ihre Verwendung in der modernen Parfümerie werden anhand von prominenten Beispielen illustriert. Unter anderem werden neue fruchtige Riechstoffe vorgestellt, die vor allem der Kopfnote von Parfüms eine besondere Signatur verleihen, aber auch durch Anwendung von Präkursor‐Technologien in der Basisnote einen olfaktorischen Beitrag leisten können. Bei den Grünnoten liegt der Schwerpunkt auf grünen Blättern und Birnen. Neue Benzodioxepine und Benzodioxole haben die marine Familie modernisiert und machten eine Überarbeitung der Olfaktophor‐Modelle notwendig. Bedeutende regulatorische Einschränkungen des Gebrauchs von Lilial und Lyral bereicherten die Parfümindustrie im floralen Bereich mit einer großen Fülle von neuen Maiglöckchen‐Riechstoffen. Darüber hinaus wurde intensiv nach neuen Rosen‐Riechstoffen geforscht, wobei ein besonderes Augenmerk auf Rosenketonen lag. Die Biotechnologie gewann signifikant an Bedeutung, wie mit Clearwood und Ambrofix belegt wird. In der holzigen Duftfamilie wurde das riechende Prinzip des Vetiveröls aufgeklärt. Eine vierte und sogar fünfte Verbindungsklasse von Moschus‐Riechstoffen wurde entdeckt, von denen einige Derivate besondere wirtschaftliche Bedeutung erlangten. All diese Aktivitäten eröffneten neue, zukunftsweisende Perspektiven und Forschungsrichtungen in der Chemie der Riechstoffe.

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Integrated comprehensive two-dimensional gas-chromatographic and spectroscopic characterization of vetiveryl acetates: Molecular identifications, quantification of constituents, regulatory and olfactory considerations

Cited by 15 publications

References 41 publications

What's Hot, What's Not: The Trends of the Past 20 Years in the Chemistry of Odorants

What's Hot, What's Not: The Trends of the Past 20 Years in the Chemistry of Odorants

The role of sample preparation in multidimensional gas chromatographic separations for non‐targeted analysis with the focus on recent biomedical, food, and plant applications

Heiße Luft oder cooler Duft? Die Trends der letzten 20 Jahre in der Riechstoffchemie

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