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Bovine Rumen Metabolome Database



Showing metabocard for Phenylacetic acid (RMDB00209)

Legend: metabolite field enzyme field

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
  1. Phenylacetic acid
  2. Phenylacetate
  3. 2-Phenylacetate
  4. 2-Phenylacetic acid
  5. Benzeneacetate
  6. Benzeneacetic acid
  7. Phenylethanoate
  8. Phenylethanoic acid
  9. a-Toluate
  10. a-Toluic acid
  11. w-Phenylacetate
  12. w-Phenylacetic acid
  13. alpha-Toluate
  14. alpha-Toluic acid
  15. omega-Phenylacetate
  16. omega-Phenylacetic acid
  17. 2-phenylethanoic acid
  18. Benzylformic acid
  19. Benzylformate
  20. 2-phenylethanoate
Chemical IUPAC Name 2-phenylacetic acid
Chemical Formula C8H8O2
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Organic acids
Class
  • Aromatic Acids
Sub Class
  • Miscellaneous aromatic acids
Family
  • Mammalian_Metabolite
Species
  • carboxylic acid; aromatic compound
Biofunction
—
Application
—
Source
  • Endogenous
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 Link Image
BioCyc ID PHENYLACETATE Link Image
BiGG ID 1486426 Link Image
Wikipedia Link Phenylacetic_acid Link Image
METLIN ID 129 Link Image
PubChem Compound 999 Link Image
PubChem Substance 11404991 Link Image
ChEBI ID 30745 Link Image
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 Link Image
SDF File Show Link Image
PDB File Show Link Image
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
  • Rumen
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
  1. Wikipedia Link Image