桂皮酸 化学特性,用途語,生産方法
定義
本品は、次の化学式で表される芳香族カルボン酸である。
解説
桂皮酸，芳香族不飽和カルボン酸の一つ。ケイ皮酸とも記す。肉桂酸(にっけいさん)、(E)-3-フェニルプロペン酸、β(ベータ)-フェニルアクリル酸ともいう。カシア油、ペルーバルサムなどに遊離またはエステルの形で含まれている。C=C二重結合に関する配置の違いによりトランス形とシス形の2種の異性体が存在し、フェニル基C6H5とカルボキシ基（カルボキシル基）COOHが反対側にあるのがトランスtrans形で、同じ側にあるのがシスcis形であるが、天然には安定なトランス形のみ存在するので、普通、桂皮酸という場合にはトランス異性体をさす。弱い芳香をもつ無色の針状結晶で、エタノール（エチルアルコール）、エーテルによく溶ける。
小学館 日本大百科全書(ニッポニカ) ）
化粧品の成分用途
皮膚コンディショニング剤
製法
エステルとして香料や化粧品に使われる。工業的には、ベンズアルデヒドと無水酢酸の縮合（パーキン反応）により合成する。
説明
Cinnamic acid is a white crystalline organic acid, which is slightly soluble in water.
It is obtained from oil of cinnamon, or from balsams such as storax. It is also found in shea butter and is the best indication of its environmental history and post-extraction conditions. It can also be made synthetically.
Cinnamic acid is used in flavors, synthetic indigo, and certain pharmaceuticals, though its primary use is in the manufacturing of the methyl, ethyl, and benzyl esters for the perfume industry. Cinnamic acid has a honey- like odor; it and its more volatile ethyl ester (ethyl cinnamate) are flavor components in the essential oil of cinnamon, in which related cinnamaldehyde is the major constituent. Cinnamic acid is also part of the biosynthetic shikimate and phenyl propanoid pathways. Its biosynthesis is performed by action of the enzyme phenylalanine ammonia - lyase (PAL) on phenylalanine.
Cinnamic acid is freely soluble in benzene, diethyl ether, acetone, and it is insoluble in hexane.
Cinnamic acid is also a kind of self-inhibitor produced by fungal spore to prevent germination.
化学的特性
Cinnamic acid is almost odorless with a burning taste, and then turning sweet and reminiscent of apricot.
天然物の起源
The trans- form has been found among the constituents of the essential oils of basil, Chinese cinnamon,
Melaleuca bracteata, Alpinia galanga. It is reported found in Peru balsam, Asian and American storax and cocoa leaves. Also
reported found in strawberry fruit, beer, cognac, starfruit (Averrhoa carambola L) and loquat. The cis- form is present in the oil of
Alpinia malacensis.
使用
cinnamic acid has sunscreen capabilities. Some manufacturers use it to replace PABA because of its lower allergic and phototoxic reaction incidence. Cinnamic acid is found in cinnamon leaves and cocoa leaves, and is an essential oil of certain mushrooms. It may cause allergic skin rashes.
定義
ChEBI: A monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. It is found in Cinnamomum cassia.
製造方法
Two isomers, trans- and cis- exist; the trans-isomer is of interest for use in flavoring; in addition to the extraction from
natural sources (storax), it can be prepared as follows: (1) from benzaldehyde, anhydrous sodium acetate and acetic anhydride in the
presence of pyridine (Perkin reaction); (2) from benzaldehyde and ethyl acetate (Claisen condensation); (3) from benzaldehyde and
acetylene chloride; (4) by oxidation of benzylidene acetone with sodium hypochlorite.
安全性プロファイル
Poison by intravenous
and intraperitoneal routes. Moderately toxic
by ingestion. A skin irritant. Combustible
liquid. When heated to decomposition it
emits acrid smoke and fumes.
純化方法
Crystallise the acid from *benzene, CCl4, hot water, water/EtOH (3:1), or 20% aqueous EtOH. Dry it at 60o in vacuo. It is steam volatile. [Beilstein 9 IV 2002.]
桂皮酸 上流と下流の製品情報
原材料
準備製品