Methyl dihydrojasmonate
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 434108344
| ImageFile = Methyl dihydrojasmonate Structural Formula V1.svg
| ImageSize = 150px
| PIN = Methyl 2-(3-oxo-2-pentylcyclopentyl)acetate
| OtherNames = Hedione
Kharismal
Cepionate
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 24851-98-7
| ChEBI = 195265
| ChEMBL = 1530328
| ChemSpiderID = 92919
| EC_number = 246-495-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 3GW44CIE3Y
| PubChem = 102861
| StdInChI=1S/C13H22O3/c1-3-4-5-6-11-10(7-8-12(11)14)9-13(15)16-2/h10-11H,3-9H2,1-2H3
| StdInChIKey = KVWWIYGFBYDJQC-UHFFFAOYSA-N
| SMILES = O=C(OC)CC1C(C(=O)CC1)CCCCC
}}
|Section2={{Chembox Properties
| C=13 | H=22 | O=3
| Appearance = Clear to pale yellow oily liquid
| MeltingPt =
| BoilingPtC= 307.8
| Solubility =
}}
|Section3={{Chembox Hazards
| MainHazards = Flammable
| FlashPtC = 113
| AutoignitionPtC =
}}
}}
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.{{Citation|first= John C. |last=Leffingwell |publisher=Leffingwell & Associates|year=2001|title= The Methyl dihydrojasmonates}}
It was first synthesised in 1962{{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}}{{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}} and is used in fine fragrances as well as cosmetics, toiletries, shampoos, soaps, and detergents.
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.{{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}}
Etymology
The name Hedione is derived from Ancient Greek hēdonḗ, meaning "pleasure", c.f. Hedonism.
Kharismal is derived From the Greek kharisma, meaning "grace" or "favor".
References
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