Identification of key odorants in complex mixtures occurring in nature

Baldovini, Nicolas; Chaintreau, Alain

doi:10.1039/d0np00020e

Cited by 36 publications

(19 citation statements)

References 314 publications

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“…Among the fragrance marine substances, special attention is paid to (+)-Dictyopterene A, which has a characteristic seawater smell [265]; it was the first odoriferous hydrocarbon isolated from Dictyopteris sp. algae [266]. The (−)-dictyotene isomer, obtained by the Cope rearrangement of Dictyopterene A, is found in the brown algae [267] and exhibits a fishy odor reminiscent of salmon roe.…”

Section: Fragrance Of Marine Floramentioning

confidence: 99%

Occurrence of Marine Ingredients in Fragrance: Update on the State of Knowledge

et al. 2021

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The fragrance field of perfumes has attracted considerable scientific, industrial, cultural, and civilizational interest. The marine odor is characterized by the specific smell of sea breeze, seashore, algae, and oyster, among others. Marine odor is a more recent fragrance and is considered as one of the green and modern fragrances. The smells reproducing the marine environment are described due to their content of Calone 1951 (7-methyl-2H-1,5-benzodioxepin-3(4H)-one), which is a synthetic compound. In addition to the synthetic group of benzodioxepanes, such as Calone 51 and its derivatives, three other groups of chemical compounds seem to represent the marine smell. The first group includes the polyunsaturated cyclic ((+)-Dictyopterene A) and acyclic (giffordene) hydrocarbons, acting as pheromones. The second group corresponds to polyunsaturated aldehydes, such as the (Z,Z)-3,6-nonadienal, (E,Z)-2,6-nonadienal, which are most likely derived from the degradation of polyunsaturated fatty acids. The third group is represented by small molecules such as sulfur compounds and halogenated phenols which are regarded as the main flavor compounds of many types of seafood. This review exposes, most notably, the knowledge state on the occurrence of marine ingredients in fragrance. We also provide a detailed discussion on several aspects of essential oils, which are the most natural ingredients from various marine sources used in fragrance and cosmetics, including synthetic and natural marine ingredients.

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Section: Fragrance Of Marine Floramentioning

confidence: 99%

Occurrence of Marine Ingredients in Fragrance: Update on the State of Knowledge

et al. 2021

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“…In ancient times, fragrances were mainly obtained from natural resources such as plant essential oils and animal secretions [ 3 , 4 , 18 , 19 ]. While natural ingredients still represent an important class of fragrances, they cannot meet the rapidly growing and diversified needs of consumers and perfumers.…”

Section: Introductionmentioning

confidence: 99%

“…The power of organic synthesis for fragrances was unlocked in 1868 when coumarin was successfully prepared by W. H. Perkin from salicylaldehyde. With the blossoming of organic synthetic methods and the related industrial technologies over the past century, synthetic and semi-synthetic fragrances emerged to become mainstream in the flavors and fragrances industries [ 2 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 ]. Nowadays, fragrance molecules represent an attractive testing ground and offer a multi-billion-dollar outlet for organic synthesis, stimulating researchers in academia and fragrance manufacture to seek out new fragrances and explore more efficient, economical, scalable and environmentally friendly synthetic methods.…”

Section: Introductionmentioning

confidence: 99%

“…With classic or new odorants as targets, innovative synthetic strategies and methods have been developed recently that enrich the frontiers of alkene and alkyne chemistry. Though there are a few reviews published on fragrance synthesis [ 2 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 ], the importance of unsaturated hydrocarbons in this area is still underestimated, especially that of alkynes and enynes.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Cyclic Fragrances via Transformations of Alkenes, Alkynes and Enynes: Strategies and Recent Progress

Lin¹,

Huang²,

Ouyang³

et al. 2022

Molecules

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With increasing demand for customized commodities and the greater insight and understanding of olfaction, the synthesis of fragrances with diverse structures and odor characters has become a core task. Recent progress in organic synthesis and catalysis enables the rapid construction of carbocycles and heterocycles from readily available unsaturated molecular building blocks, with increased selectivity, atom economy, sustainability and product diversity. In this review, synthetic methods for creating cyclic fragrances, including both natural and synthetic ones, will be discussed, with a focus on the key transformations of alkenes, alkynes, dienes and enynes. Several strategies will be discussed, including cycloaddition, catalytic cyclization, ring-closing metathesis, intramolecular addition, and rearrangement reactions. Representative examples and the featured olfactory investigations will be highlighted, along with some perspectives on future developments in this area.

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“…The need for the identification and characterization of key volatile components in wine and other matrices has already been described (Polášková et al., 2008) and was highlighted more recently (Baldovini & Chaintreau, 2020). Several useful guidelines on the identifications of volatile constituents have been published by a few international organizations, such as the International Organization of the Flavour Industry (IOFI) (Bicchi et al., 2018; IOFI, 2006), the International Union of Pure and Applied Chemistry (IUPAC) (Molyneux et al., 2019), the European Commission (European Commission, 2002), and the International Organization for Standardization (ISO) (ISO, 2020).…”

Section: Introductionmentioning

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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Identification of key odorants in complex mixtures occurring in nature

Abstract: Here are reviewed the methods based on gas chromatography-olfactometry to identify natural key odorants, followed by an overview of the richness of Nature's olfactome through examples on the chemistry of wine and various other natural odorants.

Cited by 36 publications

References 314 publications

Occurrence of Marine Ingredients in Fragrance: Update on the State of Knowledge

Occurrence of Marine Ingredients in Fragrance: Update on the State of Knowledge

Synthesis of Cyclic Fragrances via Transformations of Alkenes, Alkynes and Enynes: Strategies and Recent Progress

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

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