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Methyl dihydrojasmonate: Difference between revisions

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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''' (often referred to by its trade names of '''hedione''' or '''kharismal''') is an ] with an odour similar to that of ]. In ]s the odor is floral and ], while ] 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 is an important ], often referred to by its trade names of '''hedione''' or '''kharismal'''.

⚫ 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'''.


==Synthesis== ==Synthesis==

Revision as of 13:56, 10 January 2025

Methyl dihydrojasmonate
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 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
SMILES
  • O=C(OC)CC1C(C(=O)CC1)CCCCC
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
Chemical compound

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 recemic mixtures exhibit a dense buttery-floral odor with odor recognition thresholds of 15 parts per billion. It was first synthesised in 1962 and is 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

  1. Leffingwell, John C. (2001), The Methyl dihydrojasmonates, Leffingwell & Associates
  2. ^ 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)
  3. 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.
  4. 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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