Densities, Vapor Pressures, and Surface Tensions of Selected Terpenes

Wagner, Z.; Bendová, Magdalena; Rotrekl, Jan; Orvalho, Sandra

doi:10.1007/s10953-019-00900-3

Cited by 12 publications

(8 citation statements)

References 33 publications

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“…Another idea, which could also provide interesting new perspectives, was to open the seven-membered ring up to allow some flexibility to the double-bonded oxygen (Figure 5) in order to find the key interaction, since, in the benzodioxepinone series, the geometry of the seven-membered ring imposes the spatial orientation of the carbonyl group [199,203,208]. Therefore, the analogs of bendioxepinone (6), calcone (7) and aldolone (8) (Figure 6) exhibit an olfactory profile of: "green cresolic", "spicy, isoeugenol, guaiacol, vanillic" and "perspiration, aldehydic, slightly aldehyde muguet, vanillic, slightly metallic, nice, too weak", respectively [209]. Another alternative to preserve the marine-ozone character of the compounds was to reduce the ring size from seven to five atoms.…”

Section: Synthetic Ingredients Of Marine Fragrancementioning

confidence: 99%

“…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. Therefore, the analogs of bendioxepinone (6), calcone (7) and aldolone (8) (Figure 6) exhibit an olfactory profile of: "green cresolic", "spicy, isoeugenol, guaiacol, vanillic" and "perspiration, aldehydic, slightly aldehyde muguet, vanillic, slightly metallic, nice, too weak", respectively [209]. Therefore, the analogs of bendioxepinone (6), calcone (7) and aldolone (8) (Figure 6) exhibit an olfactory profile of: "green cresolic", "spicy, isoeugenol, guaiacol, vanillic" and "perspiration, aldehydic, slightly aldehyde muguet, vanillic, slightly metallic, nice, too weak", respectively [209].…”

Section: Synthetic Ingredients Of Marine Fragrancementioning

confidence: 99%

“…Therefore, the analogs of bendioxepinone (6), calcone (7) and aldolone (8) (Figure 6) exhibit an olfactory profile of: "green cresolic", "spicy, isoeugenol, guaiacol, vanillic" and "perspiration, aldehydic, slightly aldehyde muguet, vanillic, slightly metallic, nice, too weak", respectively [209]. Therefore, the analogs of bendioxepinone (6), calcone (7) and aldolone (8) (Figure 6) exhibit an olfactory profile of: "green cresolic", "spicy, isoeugenol, guaiacol, vanillic" and "perspiration, aldehydic, slightly aldehyde muguet, vanillic, slightly metallic, nice, too weak", respectively [209]. Another alternative to preserve the marine-ozone character of the compounds was to reduce the ring size from seven to five atoms.…”

Section: Synthetic Ingredients Of Marine Fragrancementioning

confidence: 99%

“…It is measured by diverse methods and is expressed as mmHg, and could be calculated by different equation models. A compilation of studies of the vapor pressure of odoriferous compounds has been reported by innumerable studies including terpenes, which are the largest group of natural smell compounds found in essential oils, among others [6][7][8]. The fragrant compounds are detected, via a complex olfaction mechanism, by terrestrial organisms when transported by air from a distance through an airborne signaling process,…”

Section: Introductionmentioning

confidence: 99%

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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%

Section: Synthetic Ingredients Of Marine Fragrancementioning

confidence: 99%

Section: Synthetic Ingredients Of Marine Fragrancementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

et al. 2021

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“…Indeed, vapor pressure (VP) and boiling point (BP) as well as Henry's law constant (HLC), which represents the mass transfer of molecules from liquid to air, are essential data to describe and assess the volatility of scent molecules. [3][4][5][6][7] Likewise, water solubility (WS) and octanol-water partition coefficient (log P) can bring valuable insights for the elaboration of aqueous formulations. 4 Among the available predictive approaches, mainly five stand out for estimating chemical properties with their pros and cons.…”

mentioning

confidence: 99%

COSMO‐RS as an effective tool for predicting the physicochemical properties of fragrance raw materials

Dupeux

Gaudin

Marteau‐Roussy

et al. 2022

Flavour & Fragrance J

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Each year, fragrance companies develop and patent two or three new molecules called captives. 1 These molecules are created not only to entice consumers with unique notes for perfumery but also to decrease cost, allergic reactions, feedstock shortages, or non-biodegradability/non-renewability of previous raw materials.To launch two to three captives per year on the market, screening of hundreds or thousands of molecules is necessary. As such, fragrance design requires considerable experimental work of synthesis and characterization. Hence, predicting in silico the physicochemical properties of virtual candidates can significantly contribute to a faster development of new captives with targeted features.According to the REACH regulation, 2 17 properties must be determined to bring a new molecule to the market (Table S1). However, measuring experimentally all these properties is not always realistic in terms of time, cost, feasibility at R&D level, and safety (notably for hazardous compounds). Therefore, this implementation has motivated the development of alternative approaches to experimental testing with fast and reliable methods. 2 As a consequence, thanks to improvements in computer hardware and software in the past decades, numerous tools to predict property values for large molecule sets have emerged.Perfumery is typically a field of application in which prediction of physicochemical properties can be very useful. Indeed, vapor pressure (VP) and boiling point (BP) as well as Henry's law constant (HLC), which represents the mass transfer of molecules from liquid to air, are essential data to describe and assess the volatility of scent molecules. [3][4][5][6][7] Likewise, water solubility (WS) and octanol-water partition coefficient (log P) can bring valuable insights for the elaboration of aqueous formulations. 4 Among the available predictive approaches, mainly five stand out for estimating chemical properties with their pros and cons. [5][6][7][8][9][10][11] The group contribution model (GC) or additive group method is an empirical method based on the division of molecule in blocks (functional groups). [12][13][14][15] In most cases, the property is computed as a sum

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