Methyl dihydrojasmonate
| Names | |
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| Preferred IUPAC name
Methyl 2-(3-oxo-2-pentylcyclopentyl)acetate | |
| Other names
Hedione
Kharismal Cepionate | |
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PubChem CID
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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 | edit source]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 | edit source]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 | edit source]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
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