(1R)-2β-[(Z)-2-ペンテニル]-3-オキソシクロペンタン-1α-酢酸メチル 化学特性,用途語,生産方法
外観
無色〜うすい黄色, 澄明の液体
溶解性
エタノール及びアセトンに極めて溶けやすく、水にほとんど溶けない。
用途
香料研究用、植物成長調整剤。
使用上の注意
不活性ガス封入
説明
Methyl jasmonate has a powerful, floral-herbaceous, sweet, persistent odor. Can be isolated from jasmine oil; or it may be prepared synthetically (probably in the trans-form) from muconic
acid via the methyl-3-oxo-cyclopenthyl acetate.
化学的特性
METHYL JASMONATE is a volatile component of jasmine flower absolute. It is
a colorless to pale yellow liquid, bp0.125 kPa 116–118 °C, d20
20 1.022–1.028, n20
D
1.473–1.477, possessing an odor reminiscent of the floral heart of jasmine.
Synthesis of the title compound is accomplished by reaction of (2Z)-2-buten-1-yl
bromide with Li in the presence of copper-(I) iodide, and the product is treated
with a mixture of 2-methylene- and 4-methylene-3-oxocyclopentylacetic acid
methyl ester. The aforementioned ester mixture is obtained by reaction of methyl
3-oxocyclopentylacetate with formaldehyde.
An alternative route uses a palladium-catalyzed decarboxylation of the readily
available substituted allyl 2-oxocyclopentanecarboxylates, which leads to the
corresponding cyclopentenones. Addition of dimethylmalonate, with subsequent
saponification/decarboxylation and, if necessary, (Z)-selective hydrogenation,
yields methyl jasmonate:
Methyl jasmonate exists in an equilibrium mixture in which the trans-isomer
dominates. But of all possible four enantiomeric isomers, chiefly the minor (+)-cis-isomer is responsible for the typical sensory properties of methyl jasmonate.
Therefore, several approaches to obtain this material selectively have been developed
either by directed syntheses or by enrichment using
special isomerization distillation techniques.
Methyl jasmonate is used in fine fragrances where it provides rich, soft effects in jasmine and muguet compositions.
天然物の起源
Reportedly identified in jasmine oil (Jasminum grandiflorum L.) and in Tunisian rosemary. Also found in
lemon peel oil, peppermint oil and green and fermented tea
使用
Methyl ester in perfumes.
定義
ChEBI: A jasmonate ester that is the methyl ester of jasmonic acid.
製品名
Jasmoneige® (Nippon Zeon), Splendione® (Firmenich)
(1R)-2β-[(Z)-2-ペンテニル]-3-オキソシクロペンタン-1α-酢酸メチル 上流と下流の製品情報
原材料
準備製品