リーフアルコール

外観

無色～わずかにうすい黄色, 澄明の液体

定義

本品は、次の化学式で表されるアルコールである。

溶解性

エタノール、アセトン及びジエチルエーテル等の有機溶媒と任意の割合で混和するが、水に溶けにくい。

解説

化学式CH3－CH2－CH＝CH－CH2CH2OH。3‐ヘキセン‐1‐オール　3‐hexen‐1‐olの別称。リーフアルコールは，植物の若葉に含有され，新鮮な青葉の香気をもつことによる名称である。イソアミルアルコールに似た強い香気をもつ無色の液体で，比重0.86，沸点157℃。水に微溶，アルコール，グリコール等の有機溶媒，エステル類に可溶，油に混和する。ヘキセンオールは二重結合の位置異性体のシス，トランス異性体があるが，二重結合位置が3位で，立体構造がシスのリーフアルコールのみが強い青葉の芳香をもつ。

株式会社平凡社 世界大百科事典 第２版について　情報

用途

緑茶その他の食品香料、緑臭(グリーンノート)を調合香料に与える。昆虫類の誘引剤としても有効

化粧品の成分用途

皮膚コンディショニング剤、香料

説明

Leaf alcohol exists as a liquid at room temperature with a characteristic odor of green leaves. It is found in green tea, violet leaf oil, and many types of leaves, herbs, and grasses. Leaf alcohol finds applications in perfumery as floral fragrance. Leaf alcohol is also investigated for its antidiabetic activity.

化学的特性

Leaf Alcohol is a colorless liquid with the characteristic odor of freshly cut grass. In small quantities, leaf alcohol occurs in the green parts of nearly all plants. The volatile flavor constituents of green tea contain up to 30%.
A stereospecific synthesis of (Z)-3-hexen-1-ol starts with the ethylation of sodium acetylide to 1-butyne, which is reacted with ethylene oxide to give 3-hexyn-1-ol. Selective hydrogenation of the triple bond in the presence of palladium catalysts yields (Z)-3-hexen-1-ol. Biotechnological processes have been developed for its synthesis as a natural flavor compound, for example.
Leaf alcohol is used to obtain natural green top notes in perfumes and flavors. In addition, it is the starting material for the synthesis of (2E,6Z)-2,6-nonadien-l-ol and (2E,6Z)-2,6-nonadien-l-al.

天然物の起源

Main constituent of the oil distilled from the infusion of fermented tea leaves. Reported found as the corresponding ester of phenylacetic acid in the oil of Japanese mint (Mentha arvensis); the volatile oil of Thea chinensis contains approximately 26 to 35% 3-hexen-1-ol, whereas larger amounts are reported in the oils of Morus bombysic, Robinia pseudacacia and Raphanus sativus. Probably occurring also in several green leaves and herbs; reported found in the fruit juices of raspberry, grapefruit and others. Also reported in over 200 foods including apple, apricot, banana, citrus peel oils and juices, berries, guava, mango, grapes, pineapple, cabbage, kohlrabi, celery, cucumber, lettuce, leek, peas, sauerkraut, tomato, ginger, peppermint oil, coconut oil, spearmint oil, mustard, parsley, breads, butter, fish, fish oil, cognac, brandy, cider, sherry, grape wines, tea, soybeans, avocado, olive, passion fruit, plum, rose apple, Malay apple, water apple (Syzigium spp.), beans, marjoram, starfruit, broccoli, pear and apple brandies, figs, brussels sprouts, radish, prickly pear, litchi, dill, lovage, pumpkin, corn oil, malt, laurel, kiwifruit and other sources

定義

ChEBI: A primary alcohol that consists of (3Z)-hex-3-ene substituted by a hydroxy group at position 1.

製造方法

By the reaction of butyne-1 with ethylene oxide and subsequent selective reduction to the eis isomer (Bedoukian, 1967).

一般的な説明

cis-3-Hexen-1-ol is one of the key volatile constituents of green leaf volatiles(GLV) that can act as an attractant to various insects. It is emitted by green plants when they are physically damaged.

参考文献

[1] NPCS Board of Consultants & Engineers, Industrial Alcohol of Technology Handbook, 2010
[2] A. Shirwaikar, K. Rajendran and C. Kumar, Oral Antidiabetic Activity of Annona squamosa Leaf Alcohol Extract in NIDDM Rats, Pharmaceutical Biology, 2004, vol. 42, 30-35