Phenylacetic acid Chemical Properties

Melting point:

76-78 °C(lit.)

Boiling point:

265 °C(lit.)

Density 

1.081 g/mL at 25 °C(lit.)

vapor density 

~4 (vs air)

vapor pressure 

1 mm Hg ( 97 °C)

refractive index 

1.5120 (estimate)

FEMA 

2878 | PHENYLACETIC ACID

Flash point:

132°C

storage temp. 

Store at RT.

solubility 

DMF: 1 mg/ml; PBS (pH 7.2): 10 mg/ml

pka

4.28(at 18℃)

Specific Gravity

1.081

color 

Leaflets on distillation in vac; plates, tablets from pet ether

Odor

disagreeable odor of geranium

PH

3.7(1 mM solution);3.17(10 mM solution);2.66(100 mM solution)

Odor Type

honey

Water Solubility 

15 g/L (20 ºC)

Merck 

14,7268

JECFA Number

1007

BRN 

1099647

Dielectric constant

3.0（20℃）

Stability:

Stable. Incompatible with strong oxidizing agents.

LogP

0.811 at 25℃

CAS DataBase Reference

103-82-2(CAS DataBase Reference)

NIST Chemistry Reference

Benzeneacetic acid(103-82-2)

EPA Substance Registry System

Phenylacetic acid (103-82-2)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

RIDADR 

UN 3335

WGK Germany 

1

RTECS 

AJ2430000

F 

13

TSCA 

Yes

HS Code 

29163400

Hazardous Substances Data

103-82-2(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: > 5000 mg/kg LD50 dermal Rabbit > 5000 mg/kg

MSDS

• Language:English Provider:Benzeneacetic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Phenylacetic acid Usage And Synthesis

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 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.

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.

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 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.

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 used in the synthesis of Diclofenac (D436450) and its metabolite 4'-Hydroxydiclofenac (H825225), which is the principal human metabolite of Diclofenac.

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.

Synthesis Reference(s)

The Journal of Organic Chemistry, 20, p. 440, 1955 DOI: 10.1021/jo01122a005
Tetrahedron Letters, 26, p. 2027, 1985 DOI: 10.1016/S0040-4039(00)94770-1

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.]

Phenylacetic acid(103-82-2)Related Product Information

• 4-Hydroxyphenylacetic acid
• 4-Biphenylacetic acid
• α-Lipoic Acid
• 4-Chlorophenylacetic acid
• Citric acid
• Folic acid
• Stearic acid
• 4-Methoxyphenylacetic acid
• 2-Chlorophenylacetic acid
• Ethyl 2-(Chlorosulfonyl)acetate
• Hyaluronic acid
• m-Toluic acid
• Acetophenone
• Benzeneacetonitrile
• Ascoric Acid
• Benzocyclobutyl-1-carboxylic acid
• 1-Phenyl-1-cyclopropanecarboxylic acid
• 1-(4-CHLOROPHENYL)-1-CYCLOPROPANECARBOXYLIC ACID
• Phenylacetic