[R,(+)]-7-ヒドロキシ-3,7-ジメチルオクタナール

外観

無色～黄色, 澄明の液体

定義

本品は、次の化学式で表されるテルペンアルデヒドである。

溶解性

50%エタノールに可溶。水、グリセリン、鉱油に微溶。

用途

スズラン、ユリ、ボダイジュ花、ライラック、シクラメン様香料の調合剤。

化粧品の成分用途

香料

説明

Hydroxycitronellal has an intense, sweet, floral, lily-type odor. It may be prepared by hydration of natural citronellal obtained from Java citronella or from Eucalyptus citriodora; P-pinene is converted to myrcene, which on hydration may yield either linalool or a mixture of geranoil and nerol; the latter mixture can be hydrogenated to citronellol and subsequently converted to citronellal and hydroxycitronellal; also by hydrogenation of 3,7-dimethyl- 7-hydroxy-2-octen-2-al over palladium carbon in ethyl acetate solution.

化学的特性

clear colourless liquid

天然物の起源

Reported found in pepper

使用

Hydroxycitronellal is a fragrance for use in various perfumes, antiseptics, insecticides and household products; some perfumery uses (sweet pea Pois De Senteur; gardenia; cherry; melon; mint).

製造方法

The most important synthetic routes to hydroxydihydrocitronellal are listed as follows.
1) Synthesis from citronellal: One of the oldest routes to hydroxydihydrocitronellal is the hydration of the citronellal bisulfite adduct (obtained at low temperature) with sulfuric acid, followed by decomposition with sodium carbonate. A more recent development is hydration of citronellal enamines or imines, followed by hydrolysis.
2) Synthesis from citronellol. Citronellol is hydrated to 3,7-dimethyloctane-1,7- diol, for example, by reaction with 60% sulfuric acid. The diol is dehydrogenated catalytically in the vapor phase at low pressure to give highly pure hydroxydihydrocitronellal in excellent yield.The process is carried out in the presence of, for example, a copper–zinc catalyst; at atmospheric pressure, noble metal catalysts can also be used.
3) Synthesis from 7-hydroxygeranyl/-neryl dialkylamine: The starting material can be obtained by treatment of myrcene with a dialkylamine in the presence of an alkali dialkylamide, followed by hydration with sulfuric acid. The 7-hydroxygeranyl/-neryl dialkylamine isomerizes to the corresponding 7-hydroxyaldehyde enamine in the presence of a palladium(II)- phosphine complex as catalyst. Hydrolysis of the enamine gives 7-hydroxydihydrocitronellal [151].

定義

ChEBI: The tertiary alcohol arising from addition of water across the C2C double bond of citronellal.

製品名

Laurinal® (Takasago).

接触アレルゲン

Hydroxycitronellal is a classical fragrance allergen, found in many products. It is contained in “fragrance mix.” It has to be listed by name in the cosmetics of the EU.

安全性プロファイル

A skin irritant. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALDEHYDES.