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| '''Methyl dihydrojasmonate''' is an ] that smells similar to ]. In ]s the odor is floral and ] while epimerized mixtures exhibit a dense buttery-floral odor with odor recognition thresholds of 15 parts per billion.<ref>{{Citation|first= John C. |last=Leffingwell |publisher=Leffingwell & Associates|year=2001|title= The Methyl dihydrojasmonates}}</ref> | '''Methyl dihydrojasmonate''' is an ] that smells similar to ]. In ]s the odor is floral and ] while epimerized mixtures exhibit a dense buttery-floral odor with odor recognition thresholds of 15 parts per billion.<ref>{{Citation|first= John C. |last=Leffingwell |publisher=Leffingwell & Associates|year=2001|title= The Methyl dihydrojasmonates}}</ref> | ||
| It was first synthesised in 1962<ref name=origin>{{cite journal |last1=Demole |first1=E. |last2=Lederer |first2=E. |last3=Mercier |first3=D. |title=Synthèse du dihydrojasmonate de méthyle (pentyl‐2‐oxo‐3‐cyclopentylacétate de méthyle) |journal=Helvetica Chimica Acta |date=January 1962 |volume=45 |issue=2 |pages=685–692 |doi=/10.1002/hlca.19620450234}}</ref><ref>{{cite journal |last1=Demole |first1=E. |last2=Lederer |first2=E. |last3=Mercier |first3=D. |title=Isolement et détermination de la structure du jasmonate de méthyle, constituant odorant caractéristique de l'essence de jasmin |journal=Helvetica Chimica Acta |date=January 1962 |volume=45 |issue=2 |pages=675–685 |doi=10.1002/hlca.19620450233}}</ref> and an important ] often referred to by its trade names of '''hedione''' or '''kharismal'''. | |||
| The compound is also known as '''hedione''' or '''kharismal'''. Its boiling point is 110°C at 0.2 mmHg and it has an refractive Index: 1.45800 to 1.46200 (20.00°C). | |||
| == |
==Synthesis== | ||
| Some of the earliest synthesis was based on the selective hydrogenation of ], which was obtained from natural jasmin oil.<ref name=origin /> However, as this comprised <0.8% of the oil better routes were soon developed. Modern synthesis involves the condensation of ] and ], followed by C=C bond isomerisation to give the 2-pentyl-] derivative. ] of this with ], followed by ] gives the desired product.<ref>{{cite journal |last1=Chapuis |first1=Christian |title=The Jubilee of Methyl Jasmonate and Hedione ® |journal=Helvetica Chimica Acta |date=September 2012 |volume=95 |issue=9 |pages=1479–1511 |doi=10.1002/hlca.201200070}}</ref> | |||
| * ] | |||
| ==Etymology== | |||
| The name Hedione is derived from from Ancient Greek ''hēdonḗ'', meaning "pleasure", c.f. ]. | |||
| Kharismal is derived From the Greek ''kharisma'', meaning "grace" or "favor". | |||
| ==References== | ==References== | ||
Revision as of 13:53, 10 January 2025
 | |
| Names | |
|---|---|
| Preferred IUPAC name Methyl 2-(3-oxo-2-pentylcyclopentyl)acetate | |
| Other names
Hedione Kharismal Cepionate | |
| Identifiers | |
| CAS Number | |
| 3D model (JSmol) | |
| ECHA InfoCard | 100.042.254 
|
| PubChem CID | |
| UNII | |
| CompTox Dashboard (EPA) | |
SMILES
| |
| Properties | |
| Chemical formula | C13H22O3 |
| Molar mass | 226.316 g·mol |
| 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 | 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 , 100 kPa).
 N verify (what is ?)
Infobox references
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Methyl dihydrojasmonate is an aroma compound that smells similar to 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.
It was first synthesised in 1962 and an important aroma compound often referred to by its trade names of hedione or kharismal.
Synthesis
Some of the earliest synthesis was based on the selective hydrogenation of methyl jasmonate, which was obtained from natural jasmin oil. 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.
Etymology
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
- Leffingwell, John C. (2001), The Methyl dihydrojasmonates, Leffingwell & Associates
- ^ 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.
{{cite journal}}: Check|doi=value (help) - 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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