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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| ECHA InfoCard | 100.042.254 |
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 odour similar to that of jasmine. 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] It was first synthesised in 1962[2][3] and is used in fine fragrances as well as cosmetics, toiletries, shampoos, soaps, and detergents.
Synthesis
[edit]Some of the earliest synthesis was based on the selective hydrogenation of methyl jasmonate, which was obtained from natural jasmin oil.[2] However, as this comprised <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.[4]
Etymology
[edit]The name Hedione is derived from from Ancient Greek hēdonḗ, meaning "pleasure", c.f. Hedonism. Kharismal is derived From the Greek kharisma, meaning "grace" or "favor".
References
[edit]- ^ Leffingwell, John C. (2001), The Methyl dihydrojasmonates, Leffingwell & Associates
- ^ 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.
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