Phenylacetic acid

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Phenylacetic acid
Phenylacetic acid
Ball-and-stick model
Identifiers
CAS number 103-82-2 YesY
ChemSpider 10181341 YesY
UNII ER5I1W795A YesY
ChEBI CHEBI:30745 YesY
ChEMBL CHEMBL1044 YesY
Jmol-3D images Image 1
Properties
Molecular formula C8H8O2
Molar mass 136.15 g/mol
Density 1.0809 g/cm3
Melting point 76–77 °C
Boiling point 265.5 °C
Solubility in water 15 g/L
Acidity (pKa) 4.31[1]
Hazards
MSDS External MSDS
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Phenylacetic acid (abr. PAA and synonyms are: α-toluic acid, benzeneacetic acid, alpha tolylic acid, 2-phenylacetic acid) is an organic compound containing a phenyl functional group and a carboxylic acid functional group. It is a white solid with a disagreeable odor. Because it is used in the illicit production of phenylacetone (used in the manufacture of meth/amphetamine), it is subject to controls in the United States.

Occurrence[edit]

Phenylacetic acid has been found to be an active auxin (a type of plant hormone),[2] found predominantly in fruits. However, its effect is much weaker than the effect of the basic auxin molecule indole-3-acetic acid. In addition the molecule is naturally produced by the metapleural gland of most ant species and used as an antimicrobial. It is also the oxidation product of phenethylamine when acted on by the enzyme monoamine oxidase found in humans and many other organisms.

Preparation[edit]

This compound may be prepared by the hydrolysis of benzyl cyanide:[3][4]

Synthesis of phenylacetic acid from benzyl cyanide.png
Phenylacetic acid

Applications[edit]

Phenylacetic acid is used in some perfumes, possessing a honey-like odor in low concentrations, and is also used in penicillin G production. It is also employed to treat type II hyperammonemia to help reduce the amounts of ammonia in a patient's bloodstream by forming phenylacetyl-CoA, which then reacts with nitrogen-rich glutamine to form phenylacetylglutamine. This compound is then secreted by the patient's body.

See also[edit]

References[edit]

  1. ^ Dippy, J. F. J.; Hughes, S. R. C.; Rozanski, A. (1959). "The dissociation constants of some symmetrically disubstituted succinic acids". Journal of the Chemical Society 1959: 2492–2498. doi:10.1039/JR9590002492. 
  2. ^ Wightman, F.; Lighty, D. L. (1982). "Identification of phenylacetic acid as a natural auxin in the shoots of higher plants". Physiologia Plantarum 55 (1): 17–24. doi:10.1111/j.1399-3054.1982.tb00278.x. 
  3. ^ Adams R.; Thal, A. F. (1922), "Phenylacetic acid", Org. Synth. 2: 59 ; Coll. Vol. 1: 436 
  4. ^ Wenner, W. (1952), "Phenylacetamide", Org. Synth. 32: 92 ; Coll. Vol. 4: 760