Phenylacetic acid
| Phenylacetic acid | |
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Phenylacetic acid |
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| Identifiers | |
| CAS number | 103-82-2  |
| ChemSpider | 10181341 |
| UNII | ER5I1W795A |
| ChEBI | CHEBI:30745 |
| ChEMBL | CHEMBL1044 |
| Jmol-3D images | Image 1 |
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| 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 |
| Acidity (pKa) | 4.31[1] |
| Hazards | |
| MSDS | External MSDS |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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 odour. 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
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. It is also the oxidation product of phenethylamine when acted on by the enzyme monoamine oxidase found in humans and many other organisms.
Preparation
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Applications
Phenylacetic acid is used in some perfumes, possessing a honey-like odour 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.
References
- ^ 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.
- ^ 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.
- ^ Adams R.; Thal, A. F. (1922), "Phenylacetic acid", Org. Synth. 2: 59; Coll. Vol. 1: 436
- ^ Wenner, W. (1952), "Phenylacetamide", Org. Synth. 32: 92; Coll. Vol. 4: 760
