Methyl dihydrojasmonate (often referred to by its trade names of hedione or kharismal) is an

aroma compound An aroma compound, also known as an odorant, aroma, fragrance, flavoring or flavor, is a chemical compound that has a smell or odor. For an individual chemical or class of chemical compounds to impart a smell or fragrance, it must be sufficien ...

with an odour similar to that of

jasmine Jasmine (botanical name: ''Jasminum'', pronounced ) is a genus of shrubs and vines in the olive family of Oleaceae. It contains around 200 species native to tropical and warm temperate regions of Eurasia, Africa, and Oceania. Jasmines are wid ...

. In

racemic mixture In chemistry, a racemic mixture or racemate () is a mixture that has equal amounts (50:50) of left- and right-handed enantiomers of a chiral molecule or salt. Racemic mixtures are rare in nature, but many compounds are produced industrially as r ...

s the odor is floral and

citrus ''Citrus'' is a genus of flowering trees and shrubs in the family Rutaceae. Plants in the genus produce citrus fruits, including important crops such as oranges, mandarins, lemons, grapefruits, pomelos, and limes. ''Citrus'' is nativ ...

, while

epimer In stereochemistry, an epimer is one of a pair of diastereomers. The two epimers have opposite configuration at only one stereogenic center out of at least two. All other stereogenic centers in the molecules are the same in each. Epimerization is t ...

ized mixtures exhibit a dense buttery-floral odor with odor recognition thresholds of 15 parts per billion. It was first synthesised in 1962 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 Methyl jasmonate (abbreviated MeJA) is a volatile organic compound used in plant defense and many diverse developmental pathways such as seed germination, root growth, flowering, fruit ripening, and senescence. Methyl jasmonate is derived from ja ...

, 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 Cyclopentanone is the organic compound with the formula (CH2)4CO. This cyclic ketone is a colorless volatile liquid. Preparation Ketonic decarboxylation of adipic acid gives cyclopentanone. The reaction is conducted at elevated temperatures in t ...

and

pentanal Pentanal (also called valeraldehyde) is the organic compound with molecular formula . Classified as an alkyl aldehyde, it is a colorless volatile liquid. Its odor is described as fermented, bready, fruity, nutty, berry. Production Pentanal i ...

, followed by C=C bond isomerisation to give the 2-pentyl-

cyclopentenone 2-Cyclopentenone is the organic compound with the chemical formula . 2-Cyclopentenone contains two functional groups, a ketone and an alkene. It is a colorless liquid. Its isomer, 3-cyclopentenone is less commonly encountered. The term cyclopent ...

derivative.

Michael reaction In organic chemistry, the Michael reaction or Michael 1,4 addition is a reaction between a Michael donor (an enolate or other nucleophile) and a Michael acceptor (usually an α,β-unsaturated carbonyl) to produce a Michael adduct by creating a c ...

of this with dimethyl malonate, followed by

decarboxylation Decarboxylation is a chemical reaction that removes a carboxyl group and releases carbon dioxide (CO2). Usually, decarboxylation refers to a reaction of carboxylic acids, removing a carbon atom from a carbon chain. The reverse process, which is ...

gives the desired product.

Etymology

The name Hedione is derived from Ancient Greek ''hēdonḗ'', meaning "pleasure", cf.

Hedonism Hedonism is a family of Philosophy, philosophical views that prioritize pleasure. Psychological hedonism is the theory that all human behavior is Motivation, motivated by the desire to maximize pleasure and minimize pain. As a form of Psycholo ...

. Kharismal is derived From the Greek ''kharisma'', meaning "grace" or "favor".

References

Perfume ingredients Methyl esters Cyclopentanes Plant hormones {{ester-stub