Record Information
Version1.0
Creation date2015-10-09 22:28:16 UTC
Update date2017-01-19 02:36:12 UTC
FoodComEx IDPC000097
FoodDB RecordFDB010558
Chemical Information
NamePhenylacetic acid
DescriptionFound in essential oils, e.g. neroli, rose oil, free and as estersand is also present in grapes, raspberry, strawberry, cherimoya, other fruits, cheddar cheese, Swiss cheese, wine, black tea, peated malt and other foodstuffs. Flavouring ingredient Phenyl acetate (or phenylacetate) is a carboxylic acid ester that has been found in the biofluids of patients with nephritis and/or hepatitis as well as patients with phenylketonuria (PKU). Excess phenylalanine in the body can be disposed of through a transamination process leading to the production of phenylpyruvate. The phenylpyruvate can be further metabolized into a number of products. Decarboxylation of phenylpyruvate gives phenylacetate, while a reduction reaction gives phenyllactate. The phenylacetate can be further conjugated with glutamine to give phenylacetyl glutamine. All of these metabolites can be detected in serum and urine of PKU patients. Phenyl acetate is also produced endogenously as the metabolite of 2-Phenylethylamine, which is mainly metabolized by monoamine oxidase to form phenyl acetate. 2-phenylethylamine is an "endogenous amphetamine" which may modulate central adrenergic functions, and the urinary phenyl acetate levels have been postulated as a marker for depression. (PMID: 17978765, 476920, 6857245). Phenylacetate is also found in essential oils, e.g. neroli, rose oil, free and as esters' and in many fruits. As a result it is used as a perfumery and flavoring ingredient.; Phenylacetic acid (abr. PAA and synonyms are: ?-toluic acid, benzeneacetic acid, alpha tolylic acid, 2-phenylacetic acid) is an organic compound containing a phenyl functional group and an acetic 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/amphetamines), it is subject to controls in the United States.
CAS Number103-82-2
Structure
Thumb
Synonyms
SynonymSource
2-Phenylacetatebiospider
2-Phenylacetic acidbiospider
2-Phenylethanoatebiospider
2-Phenylethanoic acidbiospider
a-Toluatebiospider
a-Toluic aciddb_source
alpha-Toluatebiospider
alpha-Toluic acidbiospider
alpha-Tolylic acidbiospider
Benzenacetic acidbiospider
Benzeneacetatebiospider
Benzeneacetic acidbiospider
Benzeneacetic acid, 9CIdb_source
Benzylcarboxylic acidbiospider
BenzylformateGenerator
Benzylformic acidbiospider
FEMA 2878db_source
omega-Phenylacetatebiospider
omega-Phenylacetic acidbiospider
Phenyl-acetic acidbiospider
Phenylacetatemanual
Phenylethanoatebiospider
Phenylethanoic aciddb_source
Phenyllacetic acidbiospider
W-PhenylacetateHMDB
W-Phenylacetic acidHMDB
α-toluateGenerator
α-toluic acidGenerator
Chemical FormulaC8H8O2
IUPAC name2-phenylacetic acid
InChI IdentifierInChI=1S/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)
InChI KeyWLJVXDMOQOGPHL-UHFFFAOYSA-N
Isomeric SMILESOC(=O)CC1=CC=CC=C1
Average Molecular Weight136.1479
Monoisotopic Molecular Weight136.0524295
Chemical Taxonomy
ClassificationNot classified
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logP1.41HANSCH,C ET AL. (1995)
Experimental Water Solubility16.6 mg/mL at 20 oCCHIOU,CT et al. (1977)
Melting PointMp 77-78.5°DFC
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 500 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
Toronto Research Chemicals P319180