Version |
1.0 |
Creation Date |
2005-11-16 15:48:42 |
Update Date |
2009-08-25 16:56:58 |
Accession Number |
RMDB00209 |
Common Name |
Phenylacetic acid |
Description |
Phenylacetate is an organic compound containing a phenyl functional group and a carboxylic acid functional group. It is a white solid with a disagreeable odor.
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. 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. |
Synonyms |
- Phenylacetic acid
- Phenylacetate
- 2-Phenylacetate
- 2-Phenylacetic acid
- Benzeneacetate
- Benzeneacetic acid
- Phenylethanoate
- Phenylethanoic acid
- a-Toluate
- a-Toluic acid
- w-Phenylacetate
- w-Phenylacetic acid
- alpha-Toluate
- alpha-Toluic acid
- omega-Phenylacetate
- omega-Phenylacetic acid
- 2-phenylethanoic acid
- Benzylformic acid
- Benzylformate
- 2-phenylethanoate
|
Chemical IUPAC Name |
2-phenylacetic acid |
Chemical Formula |
C8H8O2 |
Chemical Structure |
 |
Chemical Taxonomy |
Kingdom |
|
Super Class |
|
Class |
|
Sub Class |
- Miscellaneous aromatic acids
|
Family |
|
Species |
- carboxylic acid; aromatic compound
|
Biofunction |
— |
Application |
— |
Source |
|
|
Average Molecular Weight |
136.148 |
Monoisotopic Molecular Weight |
136.052429 |
Isomeric SMILES |
OC(=O)CC1=CC=CC=C1 |
Canonical SMILES |
OC(=O)CC1=CC=CC=C1 |
KEGG Compound ID |
C07086  |
BioCyc ID |
PHENYLACETATE  |
BiGG ID |
1486426  |
Wikipedia Link |
Phenylacetic_acid  |
METLIN ID |
129  |
PubChem Compound |
999  |
PubChem Substance |
11404991  |
ChEBI ID |
30745  |
CAS Registry Number |
103-82-2 |
InChI Identifier |
InChI=1/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10) |
Synthesis Reference |
Zhou, Shu-jing; Li, Jin-lian; Luan, Fang. New synthetic method for benzeneacetic acid. Huaxue Yu Shengwu Gongcheng (2005), 22(2), 43-44. |
Melting Point (Experimental) |
76.7 oC |
Experimental Water Solubility |
16.6 mg/mL [CHIOU,CT et al. (1977)]
Source: PhysProp
|
Predicted Water Solubility |
3.61 mg/mL [Predicted by ALOGPS]
Calculated using ALOGPS
|
Physiological Charge |
-1 |
State |
Solid |
Experimental LogP/Hydrophobicity |
1.41 [HANSCH,C ET AL. (1995)]
Source: PhysProp
|
Predicted LogP/Hydrophobicity |
1.72 [Predicted by ALOGPS]; 1.4 [Predicted by PubChem via XLOGP]
Calculated using ALOGPS
|
Material Safety Data Sheet (MSDS) |
Not Available |
MOL File |
Show  |
SDF File |
Show  |
PDB File |
Show  |
2D Structure |
|
3D Structure |
|
Experimental PDB ID |
Not Available |
Experimental 1H NMR Spectrum |
Not Available |
Experimental 13C NMR Spectrum |
Not Available |
Experimental 13C HSQC Spectrum |
Not Available |
Predicted 1H NMR Spectrum |
Show Image Show Peaklist
|
Predicted 13C NMR Spectrum |
Show Image Show Peaklist
|
Mass Spectrum |
Not Available |
Simplified TOCSY Spectrum |
Not Available |
BMRB Spectrum |
Not Available |
Cellular Location |
Not Available |
Biofluid Location |
|
Tissue Location |
Not Available |
Concentrations (Normal) |
Biofluid |
Rumen |
Value |
316.5+/- 61.5 uM |
Age |
4-5 years old |
Sex |
Female (lactating) |
Condition |
Normal (0% barley grain in dry matter (DM) basis) |
Breed |
Holstein-Friesian |
Experimental Condition |
Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800. |
Comments |
Not Available |
References |
- The rumen metabolome (in preparation)
|
Biofluid |
Rumen |
Value |
302.0 +/- 86.3 uM |
Age |
N/A |
Sex |
Female |
Condition |
Normal |
Breed |
Not Available |
Experimental Condition |
Not Available |
Comments |
Not Available |
References |
- Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Burim N. Ametaj, Qendrim Zebeli, Fozia Saleem, Nikolaos Psychogios, Michael J. Lewis, Suzanna M. Dunn, Jianguo Xia and David S. Wishart Metabolomics 2010;6(4):583-594
|
|
Concentrations (Abnormal) |
Biofluid |
Rumen |
Value |
462 +/- 121 uM |
Age |
4-5 years old |
Sex |
Female (lactating) |
Condition |
15% barley grain in dry matter (DM) basis |
Breed |
Holstein-Friesian |
Experimental Condition |
Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800. |
Comments |
Not Available |
References |
- The rumen metabolome (in preparation)
|
Biofluid |
Rumen |
Value |
541 +/-118 uM |
Age |
4-5 years old |
Sex |
Female (lactating) |
Condition |
30% barley grain in dry matter (DM) basis |
Breed |
Holstein-Friesian |
Experimental Condition |
Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800. |
Comments |
Not Available |
References |
- The rumen metabolome (in preparation)
|
Biofluid |
Rumen |
Value |
640 +/- 101 uM |
Age |
4-5 years old |
Sex |
Female (lactating) |
Condition |
45% barley grain in dry matter (DM) basis |
Breed |
Holstein-Friesian |
Experimental Condition |
Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800. |
Comments |
Not Available |
References |
- The rumen metabolome (in preparation)
|
|
Pathway Names |
Not Available |
HMDB Pathways |
Not Available |
KEGG Pathways |
Not Available |
SimCell Pathways |
Not Available |
General References |
- Wikipedia

|