フェニルアセトアルデヒド

化学的特性Phenylacetaldehyde has a harsh, green odor reminiscent of hyacinth on dilution. It has an unpleasant, pungent, bitter flavor, turning sweet and fruit-like at low levels. Since it readily undergoes oxidation and polymerizes, it must be stabilized by addition of antioxidants and by dilution with, for example, diethyl phthalate before use in compositions.

解説フェニルアセトアルデヒド，無色の液体．沸点194～195 ℃．d2041.0319．n20D1.5283．有機溶媒に易溶，水に難溶．ヒヤシンス様の強い花香を有する．空気中では，酸化や重合が起こりやすい．香料として用いられる．森北出版「化学辞典（第2版）

用途多くの種類の昆虫（チョウ目、ハチ目、甲虫類、アミメカゲロウ目）は、フェニルアセトアルデヒドを交信物質として利用している。マゴットセラピーにおいて抗菌作用を示すことも知られる。タバコの香りを増すために加えられる。純粋なフェニルアセトアルデヒドの匂いは、蜂蜜のよう、甘い、バラの香り、みずみずしい、草の香り、と表現される。ソバやチョコレート[4]などの食品や植物にも含まれる。ヒヤシンス、ナルシサス、アカシア、シクラメンなどのフレグランス、ラズベリー、アンズ、サクランボ、スパイスなどのフレーバーの調合原料として用いられる。

説明Phenylacetaldehyde is an organic compound which can be naturally found in buckwheat, flowers, and communication pheromones from various insect orders. It is commonly used for the preparation of fragrance as well as flavors, and applied in flavored cigarettes and beverages because of its honey-like sweet character. It is also applied in the synthesis of polymers, such as polyesters, as a rate controlling additive in polymerization reactions and used in the preparation of more complex chemicals like resmethrin, where it acts as a building block.

天然物の起源Identified among the constituents of several essential oils: neroli, Citrus sinensis leaves, other citrus species (flowers and leaves), narcissus, magnolia, lily, rose and tea. It is reported found in over 170 natural products including apricot, sour cherry, cooked apple, peach, fresh blackberry, crispbread, other types of bread, green tea, unprocessed rice, lemon balm, red sage, black currant, bilberry, cranberry, other berries, grapes, raisins, melon, papaya, guava fruit, pineapple, asparagus, celery leaves, carrot, parsley, peas, bell pepper, sweet pepper, peach, cabbage, peppermint oil, Scotch spearmint oil, mustard, vinegar, onion, cooked potato, tomato, cinnamon bark, cassia leaf, ginger, many cheeses, milk, yogurt, boiled egg, cooked and cured meats, beer, cognac, grape wines, cocoa, coffee, tea, roasted filbert, roasted peanut, soybean, pecans, cauliflower, broccoli, honey, avocado, passion fruit, beans, mushrooms, trassi, mango, tamarind, rice, licorice, buckwheat, lovage root, pumpkin, sweet potato, cassava, corn oil, malt, wort, dried bonito, loquat, pawpaw, maté, sweet grass oil, orange peel oil, grapefruit juice, endive, clam and Chinese quince.

使用Phenylacetaldehyde is used for the preparation of fragrances and polymers like polyesters, which find application as a rate controlling additive in polymerization reactions. It is an active component of fragrances and floral scent due to its honey-like sweet character and finds application in flavored cigarettes and beverages. It is an insect attractant and utilized in blacklight trap for pests. It is also used as a building block in the synthesis of more complex chemicals, such as resmethrin. Furthermore, it is used in association with acetic anhydride and allyltrimethylsilane in three-component coupling process catalyzed by LiBF4 providing homoallylic acetates.

一般的な説明Phenylacetaldehyde is an important aroma volatile found in tomato and roses. It has also been identified in potato, roasted cocoa beans and honey. Phenylacetaldehyde is also a potent moth attractant.

使用用途1. 香料 フェニルアセトアルデヒドは、主に花、果実などの調合香料として使用されています。単体では蜂蜜のような、甘いバラの香り、みずみずしい草の香りなどと表現されます。 このような香りを活かして、ヒヤシンスやスイセン、アカシア、シクラメンなどのフレグランス、またはラズベリー、アンズ、サクランボ、スパイスなどのフレーバーを付加するために、他の香料に対して添加されてきました。また、タバコの香りを増すためにも有用です。 2. ポリマー合成添加剤 フェニルアセトアルデヒドは、重合中の反応速度を制御するために、ポリエステル合成系に添加されます。

The most important method industrially is the isomerization of styrene oxide. Ion-exchange resins, catalysis by chromium trioxide–tungsten trioxide on graphite or silicon dioxide–aluminum trioxide, and thermolysis are recommended for the rearrangement. Phenylacetaldehyde can also be synthesized by the direct oxidation of styrene in the presence of palladium salts and copper(II) chloride in aqueous solutions of glycol ethers. Other possibilities include the catalytic dehydrogenation of 2-phenylethanol on silver or gold catalysts, the hydroformylation of benzyl halides in the presence of dicobalt octacarbonyl and sodium carbonate in acetonitrile, and the Darzens glycide ester synthesis from benzaldehyde and alkyl chloroacetates.

定義ChEBI: Phenylacetaldehyde is an aldehyde that consists of acetaldehyde bearing a methyl substituent; the parent member of the phenylacetaldehyde class of compounds. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is an alpha-CH2-containing aldehyde and a member of phenylacetaldehydes.