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SintetičkaPOPULARNO I NEOBIČNOanimalni · medni · sladak
Bazne notePiramida
—Jačina
—Trajnost
—Poreklo
Uzorak
F
Bazne note
Definicija

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.

ANIMALNI SLADAK
α-Toluic acid, benzeneacetic acid, 2-phenylacetic acid
Type
Sirovina
Olfactive family
Ambrasti i mošusni
Chemical class
carboxylic acid
Instrumenti
Piramida
GGornje note
SSrednje note
BBazne note

Miris

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.

Detaljno

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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Zanimljivosti

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.

Dobijanje i hemija

Način dobijanja

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.

Formula
C₈H₈O₂
CAS
103-82-2
Izgled
white crystalline solid
Sinonimi
α-Toluic acid, benzeneacetic acid, 2-phenylacetic acid
Status prema standardima IFRA
Pogledajte napomenu

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

Fizička svojstva
Tačka ključanja
265.5 °C
Tačka topljenja
76 to 77 °C
Tačka paljenja
>212 °F (>100 °C) (closed cup)

U parfemima

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

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