Description
Naturally occurring in various types of fruits and other plants, phenylacetic acid is a fragrant phenolic used as a perfume agent and food additive. Its pharmaceutical uses include the treatment of hyperammonemia for patients with deficiencies related to the urea cycle, and as a side chain precursor in the production of penicillin G. It also plays a role in the production of Camylofin, Bendazol, and Triafungin.
Because of its use in the production of phenylacetone (used to manufacture substituted amphetamines, including methamphetamine), it is a controlled substance.
References
https://en.wikipedia.org/wiki/Phenylacetic_acid
https://pubchem.ncbi.nlm.nih.gov/compound/phenylacetic_acid
http://www.thegoodscentscompany.com/data/rw1009911.html
https://www.drugbank.ca/drugs/DB09269
Chemical Properties
white crystals with a honey-like odour
Chemical Properties
Phenylacetic acid has a sweet, animal, honey-like odor in dilute solution. The odor is persistent and disagreeable in
concentrated solution. It has a sweet, honey-like flavor at high levels. At low levels, it is a sweetener.
Chemical Properties
Phenylacetic Acid occurs in Japanese peppermint
oil, in neroli oil, and in traces in rose oils. It is a volatile aroma constituent
of many foods (e.g., honey). It forms colorless crystals (mp 78°C) that have a
honey odor.
The common route to phenylacetic acid is conversion of benzyl chloride into
benzyl cyanide by reaction with sodium cyanide, followed by hydrolysis. Because of its intense odor, phenylacetic acid is added to perfumes in small quantities
for rounding off blossom odors. Addition to fruit aromas imparts a sweet
honey note.
Occurrence
Reported found among the constituents of a few essential oils: tobacco, Rosa centifolia, Bulgarian rose, orange
flowers absolute, neroli and Mentha arvensis of Japanese origin; also reported present among the volatile constituents of cocoa. Also
reported found in guava, papaya, raspberry, strawberry, cooked potato, tomato, peppermint oil, pepper, rye bread, cheddar cheese,
Swiss cheese, Gruyere cheese, boiled mutton, beer, cognac, cider, sherry, grape wines, white wine, sake, cocoa, tea, honey soy protein,
passion fruit, starfruit, mango, mushroom, malt, wort, roasted chicory root, naranjilla fruit, choke berry, sea buckthorn and
Chinese quince.
Uses
Phenylacetic Acid is used in the synthesis of Diclofenac (D436450) and its metabolite 4'-Hydroxydiclofenac (H825225), which is the principal human metabolite of Diclofenac.
Uses
Phenylacetic acid?has strong fixative agent and can be directly used in low-or-middle-level soap, cosmetics essences. It is usually to confect the substitute for civetta with indole quinoline type and used in acacia, sweet-scented osmanthus, rose, hosta and other floral essences.
Uses
Phenylacetic Acid is a flavoring agent that is crystalline (white, glis-
tening), with unpleasant, persisting odor resembling geranium leaf
and rose when diluted. it is soluble in most fixed oils and glycerin,
slightly soluble in water, and insoluble in mineral oil. it is obtained
by chemical synthesis. it is also termed a-toluic acid.
Definition
ChEBI: A monocarboxylic acid that is toluene in which one of the hydrogens of the methyl group has been replaced by a carboxy group.
Preparation
By the treatment of benzyl cyanide with dilute sulfuric acid and other processes.
Aroma threshold values
Detection: 1 ppm
Taste threshold values
Taste characteristics at 30 ppm: sweet, floral, chocolate, honey and tobacco.
Flammability and Explosibility
Non flammable
Safety Profile
Moderately toxic by ingestion, subcutaneous, and intraperitoneal routes. An experimental teratogen. Combustible liquid. Used in production of drugs of abuse. When heated to decomposition it emits acrid smoke and irritating fumes
Metabolism
Phenylacetic acid is conjugated in man and the chimpanzee, but probably in no other species, with glutamine. In most other animals, except the hen, it behaves like benzoic acid, forming glycine and glucuronic acid conjugates. In the hen, it conjugates with ornithine, forming phenacetornithuric acid. Phenacetylglutamine and its addition compound with urea were isolated from human urine alter the administration of phenylacetic acid (Williams, 1959).
Purification Methods
Crystallise the acid from pet ether (b 40-60o), isopropyl alcohol, 50% aqueous EtOH or hot water (m 77.8-78.2o). Dry it in vacuo. It can be distilled under a vacuum. [Beilstein 9 II 294, 9 III 2169.]
