3-(4-イソプロピルフェニル)イソブチルアルデヒド

外観

無色～ほとんど無色透明液体

解説

C13H18O(190.27)．クミンアルデヒドとプロピオンアルデヒドとを脱水縮合させて3-(4-イソプロピルフェニル)メタクリルアルデヒドとし，これに水素添加させて合成する．天然には存在しない．シクラメン様の芳香をもつのでこの名がある．"無色の液体．沸点115 ℃(0.66 kPa)．d¹⁵0.951．n²⁰_D1.50684．合成香料として，シクラメン，スズラン，ライラック系香水，せっけん香料の調合に多量に使用される．[CAS 103-95-7]

森北出版「化学辞典（第2版）

説明

2-Methyl-3-(p-isopropylphenyl) propionaldehyde has a strong, flowery odor. May be prepared by condensation of cuminic aldehyde and propionaldehyde followed by hydrogenation in the presence of a catalyst.

化学的特性

The commercially available racemate is a colorless to yellowish liquid with an intense floral odor reminiscent of Cyclamen europaeum (cyclamen, sowbread).
Production. Two main processes are used for the industrial synthesis of cyclamen aldehyde:
1) Alkaline condensation of 4-isopropylbenzaldehyde and propanal results, via the aldol, in the formation of 2-methyl-3-(4-isopropylphenyl)-2-propenal. The unsaturated aldehyde is hydrogenated selectively to the saturated aldehyde in the presence of potassium acetate and a suitable catalyst, such as palladium–alumina:
2) Friedel–Crafts reaction of isopropylbenzene and 2-methylpropenal diacetate (methacrolein diacetate) in the presence of titanium tetrachloride/boron trifluoride etherate gives cyclamen aldehyde enolacetate, which is hydrolyzed to aldehyde:
Uses. Cyclamen aldehyde is an important component for obtaining special blossomnotes in perfume compositions, particularly the cyclamen type. Because of its fresh, floral aspect, it is also used as the top note in many other blossomfragrances.

天然物の起源

Reported found in nutmeg and starfruit.

使用

Cyclamen Aldehyde is a very powerful, floral, green note used in many perfumery applications to blend into fresh, floral, green or ozonic/marine accords. It is an ingredient with growing use and importance in helping to build replacement accords for materials disappearing from the Perfumers’ palette. Cyclamen has good overall stability except in extremes of pH. It has good tenacity and substantivity and represents very good value for money in new creations.In addition to its use in numerous perfume compositions, cyclamen aldehyde is an intermediate for the preparation of fungicides and fungistatic substances.

製造方法

By condensation of cuminic aldehyde and propionaldehyde followed by hydrogenation in the presence of a catalyst

安全性プロファイル

Moderately toxic by ingestion. A human skin irritant. See also ALDEHYDES. When heated to decomposition it emits acrid smoke and irritating fumes.