Methyl dihydrojasmonate
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| Names | |
|---|---|
| Preferred IUPAC name
Methyl 2-(3-oxo-2-pentylcyclopentyl)acetate | |
| Other names
Hedione
Kharismal Cepionate | |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.042.254 |
| EC Number |
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C13H22O3 | |
| Molar mass | 226.316 g·mol−1 |
| Appearance | Clear to pale yellow oily liquid |
| Boiling point | 307.8 °C (586.0 °F; 581.0 K) |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards
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Flammable |
| Flash point | 113 °C (235 °F; 386 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Methyl dihydrojasmonate (often referred to by its trade names of hedione or kharismal) is an aroma compound with an odor similar to that of jasmine. It is a synthetic relative of methyl jasmonate, a naturally occurring compound in floral scents such as jasmine, tuberose and magnolia. In racemic mixtures the odor is floral and citrus, while epimerized mixtures exhibit a dense buttery-floral odor with odor recognition thresholds of 15 parts per billion.[1] Considered one of the compounds responsible for the projection of the scent in living flowers, it was first fully characterised and synthesized between 1957 and 1962 in jasmine absolute (0.8%) by the fragrance chemist Edouard Demole, who was working at Firmenich.[2][3][4] and is used in fine fragrances as well as cosmetics, toiletries, and detergents.
Synthesis
[edit]Some of the earliest synthesis was based on the selective hydrogenation of methyl jasmonate, which was obtained from natural jasmine oil.[3] However, as this made up <0.8% of the oil, better routes were soon developed. Modern synthesis involves the condensation of cyclopentanone and pentanal, followed by C=C bond isomerisation to give the 2-pentyl-cyclopentenone derivative. Michael reaction of this with dimethyl malonate, followed by decarboxylation gives the desired product.[5]
Use in perfumery
[edit]The first commercially successful fragrance to utilise hedione was Eau Sauvage, created by the perfumer Edmond Roudnitska for Christian Dior and launched in 1966. Adding hedione to a classically hesperidic fragrance construction created a dewy lemony magnolia-jasmine dimension without being directly floral.[citation needed] This is considered to be the beginning of a new trend in perfumery towards transparency and projection.[6]
Etymology
[edit]The name hedione is derived from Ancient Greek hēdonḗ, "pleasure" (cf. hedonism). Kharismal is derived from the Greek kharisma, meaning "grace" or "favor" (cf. charisma).
References
[edit]- ^ Leffingwell, John C. (2001), The Methyl dihydrojasmonates, Leffingwell & Associates
- ^ Theimer, Ernst T (2014). Fragrance Chemistry Science of the Sense of Smell, The. Elsevier Science. ISBN 978-0-323-13860-4. OCLC 1044713310.
- ^ a b Demole, E.; Lederer, E.; Mercier, D. (January 1962). "Synthèse du dihydrojasmonate de méthyle (pentyl-2-oxo-3-cyclopentylacétate de méthyle)". Helvetica Chimica Acta. 45 (2): 685–692. doi:10.1002/hlca.19620450234.
- ^ Demole, E.; Lederer, E.; Mercier, D. (January 1962). "Isolement et détermination de la structure du jasmonate de méthyle, constituant odorant caractéristique de l'essence de jasmin". Helvetica Chimica Acta. 45 (2): 675–685. doi:10.1002/hlca.19620450233.
- ^ Chapuis, Christian (September 2012). "The Jubilee of Methyl Jasmonate and Hedione ®". Helvetica Chimica Acta. 95 (9): 1479–1511. doi:10.1002/hlca.201200070.
- ^ Berger, Ralf Günter (2012). "Scent and Chemistry. The Molecular World of Odors. By Günther Ohloff, Wilhelm Pickenhagen and Philip Kraft". Angewandte Chemie International Edition. 51 (13). Verlag GmbH & Co. KGaA, Weinheim: 3058. doi:10.1002/anie.201201256.
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