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Phenylacetic acid

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Phenylacetic acid Basic information
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)
  • Flash point:132°C
  • storage temp. Store at RT.
  • form neat
  • pka4.28(at 18℃)
  • Specific Gravity1.081
  • color Leaflets on distillation in vac; plates, tablets from pet ether
  • Odordisagreeable odor of geranium
  • Water Solubility 15 g/L (20 ºC)
  • Merck 14,7268
  • JECFA Number1007
  • BRN 1099647
  • Stability:Stable. Incompatible with strong oxidizing agents.
  • CAS DataBase Reference103-82-2(CAS DataBase Reference)
  • NIST Chemistry ReferenceBenzeneacetic acid(103-82-2)
  • EPA Substance Registry SystemPhenylacetic 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
  • 13
  • TSCA Yes
  • HS Code 29163400
  • Hazardous Substances Data103-82-2(Hazardous Substances Data)
  • ToxicityLD50 orally in Rabbit: > 5000 mg/kg LD50 dermal Rabbit > 5000 mg/kg
Phenylacetic acid Usage And Synthesis
  • DescriptionNaturally 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
  • Chemical Propertieswhite crystals with a honey-like odour
  • Chemical PropertiesPhenylacetic 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 PropertiesPhenylacetic 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.
  • OccurrenceReported 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.
  • UsesPhenylacetic 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.
  • UsesPhenylacetic Acid is used in the synthesis of Diclofenac (D436450) and its metabolite 4'-Hydroxydiclofenac (H825225), which is the principal human metabolite of Diclofenac.
  • DefinitionChEBI: A monocarboxylic acid that is toluene in which one of the hydrogens of the methyl group has been replaced by a carboxy group.
  • PreparationBy the treatment of benzyl cyanide with dilute sulfuric acid and other processes.
  • Aroma threshold valuesDetection: 1 ppm
  • Taste threshold valuesTaste 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
  • Safety ProfileModerately 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
  • MetabolismPhenylacetic 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 MethodsCrystallise 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.]
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