| Identification | More | [Name]
Phenylacetic acid | [CAS]
103-82-2 | [Synonyms]
2-phenylacetic acid
alpha-Toluic acid
ALPHA-TOLYLIC ACID
A-TOLUIC ACID
BENZENEACETIC ACID
BENZYLFORMIC ACID
FEMA 2878
PAA
PHENYLACETIC ACID
RARECHEM AL BO 0108
α-Toluic acid
Acetic acid, phenyl-
aceticacid,phenyl-
acidephenylacetique
Benzenacetic acid
benzenaceticacid
benzeneethanoicacid
ethanoicacid,phenyl-
Kyselina fenyloctova
kyselinafenyloctova | [EINECS(EC#)]
203-148-6 | [Molecular Formula]
C8H8O2 | [MDL Number]
MFCD00004313 | [Molecular Weight]
136.15 | [MOL File]
103-82-2.mol |
| Chemical Properties | Back Directory | [Appearance]
white crystals with a honey-like odour | [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)
| [FEMA ]
2878 | [refractive index ]
1.5120 (estimate) | [Fp ]
132°C | [storage temp. ]
Store at RT. | [solubility ]
DMF: 1 mg/ml; PBS (pH 7.2): 10 mg/ml | [form ]
neat | [pka]
4.28(at 18℃) | [color ]
Leaflets on distillation in vac; plates, tablets from pet ether | [Specific Gravity]
1.081 | [Odor]
disagreeable odor of geranium | [PH]
3.53(1 mM solution);2.98(10 mM solution);2.46(100 mM solution) | [Stability:]
Stable. Incompatible with strong oxidizing agents. | [Odor Type]
honey | [Water Solubility ]
15 g/L (20 ºC) | [JECFA Number]
1007 | [Merck ]
14,7268 | [BRN ]
1099647 | [Dielectric constant]
3.0（20℃） | [LogP]
0.811 at 25℃ | [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. | [CAS DataBase Reference]
103-82-2(CAS DataBase Reference) | [NIST Chemistry Reference]
Benzeneacetic acid(103-82-2) | [EPA Substance Registry System]
103-82-2(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection . | [RIDADR ]
UN 3335 | [WGK Germany ]
1
| [RTECS ]
AJ2430000
| [F ]
13 | [TSCA ]
Yes | [HS Code ]
29163400 | [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 | [Hazardous Substances Data]
103-82-2(Hazardous Substances Data) | [Toxicity]
LD50 orally in Rabbit: > 5000 mg/kg LD50 dermal Rabbit > 5000 mg/kg |
| Questions And Answer | Back Directory | [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
|
| Hazard Information | Back Directory | [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. | [Chemical Properties]
white crystals with a honey-like odour | [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. | [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]
Nonflammable | [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.] |
|