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Phenylacetic acid is an organic compound containing a phenyl functional group and a carboxylic acid functional group. It is a white solid with a strong honey-like odor.

ТВАРИННИЙ СОЛОДКИЙ
α-Toluic acid, benzeneacetic acid, 2-phenylacetic acid
Type
Складник
Olfactive family
Амброві й мускусні
Chemical class
carboxylic acid
Інструменти
Піраміда
ВВерхні ноти
СНоти серця
ББазові ноти

Запах

Its odor is honey-like at low concentration and urine-like at high concentration. Diluted, it has a sweet honey-like odor, while the odor of the concentrated solution is suffocating and unpleasant. It is also described as having a sweet animal honey-like odor. Other descriptions give a floral odor and a disagreeable odor of geranium. Its odor threshold is undoubtedly very low but is not quantified.

Докладно

Occurrence

Phenylacetic acid is one of the main compounds responsible for the flavor of honey. Endogenously, it is a catabolite of phenylalanine. In humans it is also the oxidation product of phenethylamine, following metabolism by monoamine oxidase and then metabolism of the intermediate phenylacetaldehyde by aldehyde dehydrogenase.

In plants it is an active auxin, a type of plant hormone, found predominantly in fruits. Its effect is much weaker than that of the basic auxin molecule indole-3-acetic acid.

Chemistry

Its pKa in water is 4.31, and its conjugate base is phenylacetate. Aqueous solutions of it are weakly acidic. It undergoes ketonic decarboxylation to form ketones. Condensed with itself, it forms dibenzyl ketone. With a large excess of another carboxylic acid in the form of an acid anhydride, such as acetic anhydride, it forms phenylacetone.

Uses

Phenylacetic acid is used in penicillin G production and diclofenac production. It is also employed to treat type II hyperammonemia, where it helps reduce the ammonia in a patient's bloodstream. It does so by forming phenylacetyl-CoA, which then reacts with nitrogen-rich glutamine to form phenylacetylglutamine, and this compound is then excreted from the patient's body.

Because it can be used in the illicit production of phenylacetone, it is subject to controls in countries including the United States and China.

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Related: Aldambre · Ambrarome · Ambrein · Ambreine · Ambrettolide · Ambronova · Ammonia · Animal Notes

Цікавий факт

Most ant species produce phenylacetic acid in the metapleural gland and use it as an antimicrobial. It is also responsible for the musty odor of untreated phenylketonuria. As a flavor it is sweet and honey-like at high levels, and at low levels it is a sweetener.

Отримання й хімія

Спосіб отримання

Phenylacetic acid may be prepared by the hydrolysis of benzyl cyanide. Benzyl cyanide can be produced by Kolbe nitrile synthesis between benzyl chloride and sodium cyanide.

Формула
C₈H₈O₂
CAS
103-82-2
Зовнішній вигляд
white crystalline solid
Синоніми
α-Toluic acid, benzeneacetic acid, 2-phenylacetic acid
Статус IFRA
Див. примітку

No IFRA Standard for the material itself (51st Amendment)

Фізичні властивості
Температура кипіння
265.5 °C
Температура плавлення
76 to 77 °C
Температура спалаху
>212 °F (>100 °C) (closed cup)

У парфумерії

Phenylacetic acid is used in some perfumes because it has a persistent, honey-like odor at low concentrations.

Роль у формулі
01модифікатор
02сполучний компонент
Форми випуску
синтетична речовина

Див. також

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