Paradisone

SintetičkaPOPULARNO I NEOBIČNOcvetni · nalik jasminu
Srednje notePiramida
—Jačina
—Trajnost
—Poreklo

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Uzorak
Paradisone kao sirovina za parfeme
Srednje note
Definicija

Paradisone is the trade name of the (+)-(1R,2S) form of methyl dihydrojasmonate, a jasmine-like aroma compound. Its odor is intense, floral, jasmine-like, bright and fatty.

CVETNI SLADAK PUDERAST VOĆNI TOPAO SVEŽ TROPSKI
(+)-methyl dihydroepijasmonate, (+)-cis-methyl dihydrojasmonate
Type
Sirovina
Olfactive family
Cvetni
Source
synthetic molecule
Chemical class
aroma compound
Instrumenti
Piramida
GGornje note
SSrednje note
BBazne note
—Jačina
Intenzivan
Intenzivan

Miris

The (+)-(1R,2S) form has an intense floral, jasmine-like, bright and fatty odor. Methyl dihydrojasmonate has a powerful sweet-floral, jasmine-like, somewhat fruity odor. High-cis products have an extremely powerful jasmine character. A high-cis grade is described as a powerful floral, with jasmine and/or magnolia flower character that is sweet and fruity (peach).

Detaljno

What it is

Paradisone is the trade name of the (+)-(1R,2S) form of methyl dihydrojasmonate. This form is also called (+)-cis-methyl dihydrojasmonate. Commercial formulations contain about 90% ee of the (+)-(1R,2S) form. The (+)-(1R,2S) form is the most organoleptically active enantiomer.

Chemistry

Its molecular formula is C₁₃H₂₂O₃ and its molecular weight is 226.31. Its IUPAC name is methyl 2-[(1R,2S)-3-oxo-2-pentylcyclopentyl]acetate. Synthetic commercial formulations of methyl dihydrojasmonate contain a racemic, near equilibrium mixture of about 10% cis and about 90% trans forms.

The parent compound

Methyl dihydrojasmonate is a synthetic relative of methyl jasmonate, a naturally occurring compound in floral scents such as jasmine, tuberose and magnolia. It has been identified as a natural product in flowers, tea, herbs, fruits and vegetables. It was first fully characterised and synthesized between 1957 and 1962 by the fragrance chemist Edouard Demole.

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Related: Acerola · Akebia Fruit · Allyl Amyl Glycolate · Arctic Bramble · Argan · Berries · Black Sapote · Buriti

Dobijanje i hemija

Način dobijanja

Methyl dihydrojasmonate is prepared by Michael addition of malonic acid esters to 2-pentyl-2-cyclopenten-1-one, followed by hydrolysis, decarboxylation and esterification. 2-Pentyl-2-cyclopenten-1-one is prepared by an aldol condensation between cyclopentanone and valeraldehyde and subsequent isomerization. High-cis material can be produced from the equilibrium mixture by special distillation techniques in which isomerization is effected by the action of sodium carbonate. An industrial process for a methyl dihydrojasmonate with a high portion of the (+)-(1R)-cis-isomer uses catalytic hydrogenation of the corresponding cyclopenteneacetic acid in the presence of a ruthenium(II) complex with chiral ligands, followed by esterification.

Formula
C₁₃H₂₂O₃
Izgled
Colorless oil
Jačina mirisa
Intenzivan
Sinonimi
(+)-methyl dihydroepijasmonate, (+)-cis-methyl dihydrojasmonate
Status prema standardima IFRA
Pogledajte napomenu

No IFRA Standard for the material itself (51st Amendment)

U parfemima

Methyl dihydrojasmonate is used in perfumery for blossom fragrances, particularly in jasmine types. It is a fragrance ingredient in perfumes, toilette and laundry products. As a flavor ingredient it produces fruit, tea, tobacco and floral flavors. High-cis methyl dihydrojasmonate is used in fine fragrances. It tends to isomerize into the equilibrium mixture, so it has only limited usage in other perfumery applications.

Uloga u formuli
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06svežina
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