Structure–Activity Relationships in the Domain of Odorants Having Marine Notes

Gaudin, Jean‐Marc; Laumer, Jean‐Yves de Saint

doi:10.1002/ejoc.201403365

Cited by 6 publications

(8 citation statements)

References 27 publications

(42 reference statements)

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“…In 2010, another analog called Aquozone (12) was developed. It has a strong marine, fruity and green smell [210]. More recently, in 2018, two derivatives with isobutyl (13) and isopentyl ( 14) hyrophobic radical groups were discovered (Table 2) and have showed particularly interesting marine olfaction properties.…”

Section: Synthetic Ingredients Of Marine Fragrancementioning

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: Synthetic Ingredients Of Marine Fragrancementioning

confidence: 99%

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

et al. 2021

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“…Only recently,G audin et al [8] described that the 5 H-1,4-dioxepin-6(7 H)-one moiety could be replaced by a2 ,3-dihydrofuran-2-carbaldehyde unit leadingt oc ompound 2,f or which ap owerful tenacious aldehydic-green marine odourw as reported. Alibrary of analogues led them to propose aqualitative marine olfactophorem odel consisting of only one hydrogen- Figure 1.…”

Section: Introductionmentioning

confidence: 99%

“…Molecular structures of commercially employedb enzodioxepinone odorants 1a-d and experimental benzodioxepinoneodorants 2-5. [7,8] bond acceptor, one aliphatic hydrophobe and one aromatic binding site. [8] Both olfactophorem odels agree on the requirement of at least one potent hydrogen-bond acceptor,f or which ac arbonyl functionh as now been independently confirmed to be optimal by both Gaudin et al [8] and Hügel and co-workers.…”

Section: Introductionmentioning

confidence: 99%

“…[7,8] bond acceptor, one aliphatic hydrophobe and one aromatic binding site. [8] Both olfactophorem odels agree on the requirement of at least one potent hydrogen-bond acceptor,f or which ac arbonyl functionh as now been independently confirmed to be optimal by both Gaudin et al [8] and Hügel and co-workers. [9] Gaudin et al [8] also reported that the cyclopentene ring indeed required one ether oxygen functionality to sustain marine odorantc haracteristics, whichc onfirmed the requirement for as econd hydrogen-bond acceptorw ithin the marine olfactophore model.A ll models feature an aromatic binding site, and recent work by our group into the effects of dearomatisation of the benzo[b] [1,4]dioxepin-3-one template revealed that the marine olfactophore modelswere correct in assuming that the aromatic binding site is not just am olecular spacer,b ut an essential binding feature.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Olfactory Properties of 2‐Substituted and 2,3‐Annulated 1,4‐Dioxepan‐6‐ones

et al. 2015

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The synthesis and olfactory properties of as eries of 2-substituteda nd 2,3-annulated1 ,4-dioxepan-6-onesisr eported. By Williamson etherification with 3-chloro-2-(chloromethyl)prop-1-ene( 6)a nd subsequentK atsuki-Sharpless oxidation, 1,4-dioxepan-6-one (8a)a nd its 2-methyl (8b), 2-propyl (8c), 2-isobutyl (8d), and 2,2,3,3-tetramethyld erivative (8e), as well as four 2,3-annulated 1,4-dioxepan-6-ones 8h, 8i, 8j,a nd 8k were synthesised.B ye therification with ethyl diazoacetate and subsequent Dieckmann cyclisation, (5aS,9aS)-9-bromoand 9-iodo-5a,6,7,9a-tetrahydro-2 Hbenzo[b][1,4]dioxepin-3(4 H)-one(8f/g)aswell as a2,3-annulated derivative 8m from (+ +)-limonene were prepared. 2-Propyl-1,4-dioxepan-6-one (8c)w as discovered to have ag reen floral odourw ith anisic and cinnamic nuances, which could be rationalised by as uperpositiona nalysis. The olfactoryp roperties of the 1,4-dioxepan-6-oness ynthesised underline the crucial importance of ab enzenoid ring system for marine odorants.

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“…Methyl-2,3-dihydrobenzofuran-2-yl)methanol (3h)16 Colorless oil; yield: 89.3 mg (58%).1 H NMR (CDCl 3 ): δ = 7.05-6.83 (2 H, m, ArH), 6.75-6.50 (1 H, m, ArH), 4.99-4.79 (1 H, m, CH), 3.90-3.65 (2 H, m, CH 2 OH), 3.20 (1 H, dd, J = 15.7, 9.4 Hz, CHH), 2.95 (1 H, dd, J = 15.7, 7.4 Hz, CHH), 2.26 (3 H, s, CH 3 ). NMR (CDCl 3 ): δ = 156.9, 129.9, 128.3, 126.5, 125.6, 108.9, 83.0, 64.9, 31.2, 20.7.…”

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confidence: 99%