Identification and analysis of new α- and β-hydroxy ketones related to the formation of 3-methyl-2,4-nonanedione in musts and red wines

Peterson, Ana; Cholet, Céline; Gény, Laurence; Darriet, Philippe; Landais, Yannick; Pons, Alexandre

doi:10.1016/j.foodchem.2019.125486

Cited by 12 publications

(24 citation statements)

References 29 publications

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“…To provide an impression of freshness and cleanliness, new green odorants are much sought after.V ioliff (42), [39] ag reen, floral violet leaf-like benchmark inspired new materials such as Tanaisone (43), which possesses ah erbaceous,spicy note,and Florymoss (44), which offers aunique, mossy odor ( Figure 5). [40] These compounds are manufactured by Kondakov acylationo fc yclooctene with selective double bond shifts.T he odor thresholds of 1-4 ng L À1 air could be remarkably decreased by introduction of an ethyl ester functionality in 45.…”

Section: Leaves and Needles From Green Teatoshisomentioning

confidence: 99%

“…The3hydroxy derivative 47,and afew Baeyer-Villiger products of methyl nonadione resulting primarily from photooxidations can be regarded as precursors of diacetyl (2,3-butanedione), the character impact odorant of butter. [43] This compound is also associated with the aging of wines, [44] and 47 has been trademarked as Lactadione (47). [45] Thec reamy,b uttery aspect of methyl nonadione (46)m ost likely also results from traces of diacetyl.…”

Section: Leaves and Needles From Green Teatoshisomentioning

confidence: 99%

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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: Leaves and Needles From Green Teatoshisomentioning

confidence: 99%

Section: Leaves and Needles From Green Teatoshisomentioning

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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“…Volatile constituents identified from wine: selected wine volatile compounds identified from 1967 to 2020. References: 1 : (Van Wyk et al., 1967b), 2 : (Dubois et al., 1971), 3 : (Schreier et al., 1974), 4 and 5 : (Schreier & Drawert, 1974b), 6 : (Simpson et al., 1977), 7 : (Simpson, 1978), 8 : (Buser et al., 1982), 9 : (Masuda & Yunome, 1984), 10 : (Harris et al., 1987), 11 : (Darriet et al., 1995), 12 : (Tominaga et al., 1996), 13 – 16 : (Guth, 1997), 17 – 20 : (Tominaga et al., 1998), 21 and 22 : (Lavigne et al., 1998), 23 : (Bouchilloux, Darriet, Henry et al., 1998), 24 : (Bouchilloux, Darriet, & Dubourdieu, 1998), 25 : (Tominaga et al., 2000), 26 : (Darriet et al., 2000), 27 : (Aznar et al., 2001), 28 : (Herve et al., 2003), 29 : (Tominaga et al., 2003), 30 : (Janusz et al., 2003), 31 : (Simpson et al., 2004), 32 – 34 : (Campo, Cacho et al., 2006), 35 – 37 : (Campo, Ferreira, López et al., 2006), 38 : (Bailly et al., 2006), 39 – 41 : (Sarrazin et al., 2007), 42 : (Wood et al., 2008), 43 : (Culleré et al., 2008), 44 : (Pons et al., 2008), 45 : (Pons et al., 2011), 46 : (Nikolantonaki & Darriet, 2011), 47 : (San‐Juan et al., 2012), 48 : (Falcao et al., 2012), 49 : (Stamatopoulos et al., 2014), 50 : (Antalick et al., 2015), 51 : (Floch et al., 2016), 52 and 53 : (Pavez et al., 2015), 54 : (Pons et al., 2016), 55 – 57 : (Picard et al., 2017), 58 and 59 : (Gros et al., 2017), 60 : (Allamy et al., 2017), 61 : (Pons, Allamy, Lavigne et al., 2017; Pons et al., 2011), 62 : (Chen et al., 2018), 63 : (Schoenauer & Schieberle, 2019), 64 : (Chenot et al., 2019), 65 – 67 : (Peterson et al., 2020), 68 : (Wang et al., 2021)…”

Section: Overview Of Wine Volatile Constituents and Associated Identi...unclassified

“…However, HS–SPME has been applied for identification in cases where the structures of the volatiles to be extracted were predefined. 1,8‐Cineole 28 (Herve et al., 2003), 1,4‐cineole 50 (Antalick et al., 2015), 2‐methyl‐4‐propyl‐1,3‐oxathiane 62 (Chen et al., 2018), 3‐hydroxy‐3‐methyl‐2,4‐nonanedione 65 and anti/syn‐ketol 2‐hydroxy‐3‐methylnonan‐4‐one 66 , 67 (Peterson et al., 2020), and cis ‐2,4,4,6‐tetramethyl‐1,3‐oxathiane 68 (Wang et al., 2021) were identified in wines by using HS–SPME. HS–SPME has great potential for extracting targeted volatiles from wines, even when the volatile compounds are at trace to ultra‐trace concentrations.…”

Section: Preparation Of Wine Volatile Extractmentioning

confidence: 99%

Strategies for the identification and sensory evaluation of volatile constituents in wine

Chen

Darriet

2021

Comp Rev Food Sci Food Safe

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Wine aroma, which stems from complex perceptual and cognitive processes, is initially driven by a multitude of naturally occurring volatile constituents. Its interpretation depends on the characterization of relevant volatile constituents. With large numbers of volatile constituents already identified, the search for unknown volatiles in wine has become increasingly challenging. However, the opportunities to discover unknown volatile compounds contributing to the wine volatilome are still of great interest, as demonstrated by the recent identification of highly odorous trace (µg/L) to ultra-trace (ng/L) volatile compounds in wine. This review provides an overview of both existing strategies and future directions on identifying unknown volatile constituents in wine. Chemical identification, including sample extraction, fractionation, gas chromatography, olfactometry, and mass spectrometry, is comprehensively covered. In addition, this review also focuses on aspects related to sensory-guided wine selection, authentic reference standards, artifacts and interferences, and the evaluation of the sensory significance of discovered wine volatiles. Powerful key volatile odorants present at ultra-trace levels, for which these analytical approaches have been successfully applied, are discussed. Research areas where novel wine volatiles are likely to be identified are pointed out. The importance of perceptual interaction phenomena is emphasized. Finally, future avenues for the exploration of yet unknown wine volatiles by coupling analytical approaches and sensory evaluation are suggested.

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“…[43] Verbindung 47,a ls Lactadion geschützt, [44] wird auch mit der Alterung von Weinen in Zusammenhang gebracht. [45] Der cremige,b utterartige Aspekt des Methylnonadions (46)r esultiert hçchstwahrscheinlich ebenfalls aus oxidativ freigesetzten Spuren des Diacetyls.D af reies Diacetyl in der Parfümerie streng limitiert ist, [46] wurden Diacetylvorläufer,w ie das Diacetyldimer 5-Acetyldihydro-2-hydroxy-2,5-dimethyl-3(2H)furanon (48), als Präkursoren beschrieben. [47] Die 1,3-Diketone 49 (R 1 ,R 2 = Me;R 3 = Alkyl, OMe,OH) mit ausgeprägt buttrigen, cremigen, aber auch blumig-fruchtigen Noten, wurden ebenfalls zur Verwendung in der Parfümerie beansprucht.…”

Section: Vonb L äTtern Und Nadeln:grüntee Und Shisounclassified

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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Identification and analysis of new α- and β-hydroxy ketones related to the formation of 3-methyl-2,4-nonanedione in musts and red wines

Cited by 12 publications

References 29 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

Strategies for the identification and sensory evaluation of volatile constituents in wine

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

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