8/16/2018
`NIH
`
`U.S. National Library of Medicine
`
`Phenylacetic acid | C8H8O2 - PubChem
`National Center for Biotechnology Information
`
` O P E N
`CHEMISTRY
`D A T A B A S E
`
`Search Compounds
`
`
`
` Compound Summary for CID 999
`
`Phenylacetic Acid
`
` Cite this Record
`
`
`
`
`
`
`
`
`
`
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`
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`STRUCTURE
`
`VENDORS
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`DRUG INFO
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`PHARMACOLOGY
`
`LITERATURE
`
`PATENTS
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`BIOACTIVITIES
`
`PubChem CID:
`
`Chemical Names:
`
`Molecular Formula:
`Molecular Weight:
`InChI Key:
`Drug Information:
`Safety Summary:
`
`999
`PHENYLACETIC ACID; 2-Phenylacetic acid; Benzeneacetic acid; 103-82-2; Phenylethanoic acid;
`Alpha-Toluic acid(cid:163)(cid:163)(cid:163) More...
`
`C8H8O2; C6H5CH2CO2H
`136.15 g/mol
`WLJVXDMOQOGPHL-UHFFFAOYSA-N
`
`Drug Indication (cid:163)(cid:163) Clinical Trials (cid:163)(cid:163) FDA UNII
`
`Laboratory Chemical Safety Summary (LCSS)
`
`Phenylacetic acid is a Nitrogen Binding Agent. The mechanism of action of phenylacetic acid is as an Ammonium Ion
`Binding Activity.
`
` FDA Pharmacology Summary from FDA Pharm Classes
`
`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), an inborn error of metabolism. 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.
` Metabolite Description from Human Metabolome Database (HMDB)
`
`https://pubchem.ncbi.nlm.nih.gov/compound/phenylacetic_acid
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` COMPOUND
`
`
`
` PHENYLACETIC ACID
`
`
`
`Phenylacetic acid | C8H8O2 - PubChem
`Modify Date: 2018-08-15; Create Date: 2004-09-16
`
`https://pubchem.ncbi.nlm.nih.gov/compound/phenylacetic_acid
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`Phenylacetic acid | C8H8O2 - PubChem
`
` Contents
`1 2D Structure
`2 3D Conformer
`3 Names and Identifiers
`4 Chemical and Physical Properties
`5 Related Records
`6 Chemical Vendors
`7 Drug and Medication Information
`8 Food Additives and Ingredients
`9 Pharmacology and Biochemistry
`10 Use and Manufacturing
`11 Identification
`12 Safety and Hazards
`13 Toxicity
`14 Literature
`15 Patents
`16 Biomolecular Interactions and Pathways
`17 Biological Test Results
`18 Classification
`19 Information Sources
`
`https://pubchem.ncbi.nlm.nih.gov/compound/phenylacetic_acid
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`Phenylacetic acid | C8H8O2 - PubChem
`
`1 2D Structure
`
` Search
`
` Download
`
` Get Image
`
` Magnify
`
` from PubChem
`
`https://pubchem.ncbi.nlm.nih.gov/compound/phenylacetic_acid
`
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`Phenylacetic acid | C8H8O2 - PubChem
`
`2 3D Conformer
`
` Search
`
` Download
`
` Get Image
`
`CLICK TO LOAD...
`
` Magnify
`
` Show Hydrogens
`
` Show Atoms
`
` Animate
`
` from PubChem
`
`https://pubchem.ncbi.nlm.nih.gov/compound/phenylacetic_acid
`
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`Phenylacetic acid | C8H8O2 - PubChem
`
`3 Names and Identifiers
`
`3.1 Computed Descriptors
`
`3.1.1 IUPAC Name
`2-phenylacetic acid
`
`3.1.2 InChI
`InChI=1S/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)
`
`3.1.3 InChI Key
`WLJVXDMOQOGPHL-UHFFFAOYSA-N
`
`3.1.4 Canonical SMILES
`C1=CC=C(C=C1)CC(=O)O
`
`3.2 Molecular Formula
`1. C8H8O2
`2. C6H5CH2CO2H
`
`C H O
`8 8 2
`
`3.3 Other Identifiers
`
` from PubChem
`
` from PubChem
`
` from PubChem
`
` from PubChem
`
` from ILO-ICSC
`
` from PubChem
`
`3.3.1 CAS
`103-82-2
` from ChemIDplus, DTP/NCI, DrugBank, EPA DSStox, European Chemicals Agency (ECHA), Human Metabolome …
`
`51146-16-8
`
`https://pubchem.ncbi.nlm.nih.gov/compound/phenylacetic_acid
`
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`Phenylacetic acid | C8H8O2 - PubChem
`
` from DTP/NCI
`
`3.3.2 EC Number
`203-148-6
`
`3.3.3 FEMA Number
`2878
`
`3.3.4 ICSC Number
`1260
`
`3.3.5 NSC Number
`139637
`
`125718
`
`3.3.6 RTECS Number
`AJ2430000
`
`3.3.7 UNII
`ER5I1W795A
`
`3.3.8 Wikipedia
`
` from European Chemicals Agency (ECHA)
`
` from Flavor and Extract Manufacturers Association (FEMA)
`
` from ILO-ICSC
`
` from DTP/NCI
`
` from DTP/NCI
`
` from The National Institute for Occupational Safety and Health (NIOSH)
`
` from DrugBank, FDA/SPL Indexing Data
`
`phenylacetate
`Title
`chemical compound
`Description
`phenylacetic acid
`Title
`chemical compound
`Description
`https://pubchem.ncbi.nlm.nih.gov/compound/phenylacetic_acid
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`Phenylacetic acid | C8H8O2 - PubChem
`
` from Wikipedia
`
`11. phenylacetic acid, sodium salt , carboxy-(11)C-labeled cpd
`12. sodium phenylacetate
`
`3.4 Synonyms
`
`3.4.1 MeSH Entry Terms
`1. phenylacetate
`2. phenylacetic acid
`3. phenylacetic acid, ammonium salt
`4. phenylacetic acid, calcium salt
`5. phenylacetic acid, cesium salt
`6. phenylacetic acid, lithium salt
`7. phenylacetic acid, mercury salt
`8. phenylacetic acid, potassium salt
`9. phenylacetic acid, rubidium salt
`10. phenylacetic acid, sodium salt
`
` from MeSH
`
`3.4.2 Depositor-Supplied Synonyms
`1. PHENYLACETIC ACID
`11. Phenyllacetic acid
`2. 2-Phenylacetic acid
`12. Benzylcarboxylic acid
`3. Benzeneacetic acid
`13. Kyselina fenyloctova
`4. 103-82-2
`14. Phenylacetic acid (natural)
`5. Phenylethanoic acid
`15. Kyselina fenyloctova [Czech]
`6. alpha-Toluic acid
`16. omega-Phenylacetic acid
`7. Benzenacetic acid
`17. PHENYL ACETIC ACID
`8. phenylacetate
`18. UNII-ER5I1W795A
`9. Acetic acid, phenyl-
`19. NSC 125718
`10. Benzylformic acid
`20. BRN 1099647
`
`21. FEMA No. 2878
`22. .alpha.-Toluic acid
`23. CHEBI:30745
`24. AI3-08920
`25. HSDB 5010
`26. EINECS 203-148-6
`27. PHENYL-ACETIC ACID
`28. .omega.-Phenylacetic acid
`29. CHEMBL1044
`30. ER5I1W795A
`
`31. WLJVXDMOQOGPHL-UHFF
`32. Benzeneacetate
`33. NSC125718
`34. NCGC00159477-02
`35. DSSTox_CID_1656
`36. DSSTox_RID_76268
`37. DSSTox_GSID_21656
`38. CAS-103-82-2
`39. Phenylethanoate
`40. phenylaceticacid
`
` from PubChem
`
`https://pubchem.ncbi.nlm.nih.gov/compound/phenylacetic_acid
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`Phenylacetic acid | C8H8O2 - PubChem
`
`4 Chemical and Physical Properties
`
`4.1 Computed Properties
`
`Property Name
`Molecular Weight
`Hydrogen Bond Donor Count
`Hydrogen Bond Acceptor Count
`Rotatable Bond Count
`Complexity
`
`CACTVS Substructure Key Fingerprint
`
`Topological Polar Surface Area
`Monoisotopic Mass
`Exact Mass
`XLogP3
`Compound Is Canonicalized
`Formal Charge
`Heavy Atom Count
`Defined Atom Stereocenter Count
`Undefined Atom Stereocenter Count
`Defined Bond Stereocenter Count
`Undefined Bond Stereocenter Count
`Isotope Atom Count
`Covalently-Bonded Unit Count
`
`4.2 Experimental Properties
`
`4.2.1 Physical Description
`Solid
`
`Property Value
`136.15 g/mol
`1
`2
`2
`114
`AAADccBwMAAAAAAAAAAAAAAAAAAAAAAAAAAwAAA
`AAAAAAAABAAAAGgAACAAADACAmAAwCIAAAgCIAiDS
`CAACAAAgAAAIiAEAAIgIIDKAFRCAYAAkwAEIiAeIyKCOAA
`AAAAAAAAAAAAAAAAAAAAAAAAAAAA==
`37.3 A^2
`136.052 g/mol
`136.052 g/mol
`1.4
`true
`0
`10
`0
`0
`0
`0
`0
`1
`
` from PubChem
`
`WHITE-TO-YELLOW CRYSTALS OR FLAKES WITH PUNGENT ODOUR.
`
` from Human Metabolome Database (HMDB)
`
`https://pubchem.ncbi.nlm.nih.gov/compound/phenylacetic_acid
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`Phenylacetic acid | C8H8O2 - PubChem
`
` from ILO-ICSC
`
`4.2.2 Color
`Leaflets on distillation in-vacuo; plates, tablets from petroleum ether
`O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry,
`2013., p. 1352
`
` from HSDB
`
`Shiny, white plate crystals
`Larranaga, M.D., Lewis, R.J. Sr., Lewis, R.A.; Hawley's Condensed Chemical Dictionary 16th Edition. John Wiley & Sons, Inc. Hoboken, NJ
`2016., p. 1061
`
` from HSDB
`
`White to yellow crystals or flakes
`CDC; International Chemical Safety Cards (ICSC) 2012. Atlanta, GA: Centers for Disease Prevention & Control. National Institute for
`Occupational Safety & Health (NIOSH). Ed Info Div. Available from, as of June 12, 2017: http://www.cdc.gov/niosh/ipcs/default.html
` from HSDB
`
`4.2.3 Odor
`Floral odor
`Larranaga, M.D., Lewis, R.J. Sr., Lewis, R.A.; Hawley's Condensed Chemical Dictionary 16th Edition. John Wiley & Sons, Inc. Hoboken, NJ
`2016., p. 1061
`
` from HSDB
`
`Disagreeable odor of geranium
`Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 12th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ.
`2012., p. V5: 3562
`
` from HSDB
`
`Has a sweet honey-like odor when diluted; the odor of the concentrated solution is suffocating and unpleasant.
`Gerhartz, W. (exec ed.). Ullmann's Encyclopedia of Industrial Chemistry. 5th ed.Vol A1: Deerfield Beach, FL: VCH Publishers, 1985 to
`Present., p. VA19: 403
`
`4.2.4 Taste
`Sweet honey-like flavor at high levels; at low levels, it is a sweetner
`Burdock, G.A. (ed.). Fenaroli's Handbook of Flavor Ingredients. 6th ed.Boca Raton, FL 2010, p. 1657
`
`4.2.5 Boiling Point
`265.5 deg at 760 mm Hg
`
` from HSDB
`
` from HSDB
`
`https://pubchem.ncbi.nlm.nih.gov/compound/phenylacetic_acid
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`8/16/2018
`O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry,
`2013., p. 1352
`
`265.5°C
`
` from HSDB
`
` from ILO-ICSC
`
`4.2.6 Melting Point
`76.7 deg C
`Haynes, W.M. (ed.). CRC Handbook of Chemistry and Physics. 95th Edition. CRC Press LLC, Boca Raton: FL 2014-2015, p. 3-34
` from HSDB
`
`76.7 °C
`
`76.5°C
`
` from Human Metabolome Database (HMDB)
`
` from ILO-ICSC
`
`4.2.7 Flash Point
`132 deg C (270 deg F)
`Sigma-Aldrich; Safety Data Sheet for Phenylacetic acid. Product Number: P16621, Version 4.6 (Revision Date 04/12/2017). Available
`from, as of June 26, 2017: http://www.sigmaaldrich.com/safety-center.html
`
` from HSDB
`
`>212 deg F (>100 deg C) (closed cup)
`National Fire Protection Association; Fire Protection Guide to Hazardous Materials. 14TH Edition, Quincy, MA 2010, p. 325-97
` from HSDB
`
`132°C c.c.
`
` from ILO-ICSC
`
`4.2.8 Solubility
`In water, 1.73X10+4 mg/L at 25 deg C
`Yalkowsky, S.H., He, Yan, Jain, P. Handbook of Aqueous Solubility Data Second Edition. CRC Press, Boca Raton, FL 2010, p. 478
` from HSDB
`
`In water, 1.66X10+4 mg/L at 20 deg C
`Chio CT et al; Environ Sci Technol 11: 475-8 (1977)
`
`Soluble in alcohol and ether; Soluble 4.422 moles/L in chloroform at 25 deg C; 1.842 moles/L in carbon tetrachloride at 25
`deg C; 4.513 moles/L in acetylene tetrachloride at 25 deg C; 3.29 moles/L in trichlorethylene at 25 deg C; 1.558 moles/L in
`tetrachlorethylene at 25 deg C; 3.252 moles/L in pentachloroethane at 25 deg C
`
` from HSDB
`
`https://pubchem.ncbi.nlm.nih.gov/compound/phenylacetic_acid
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`8/16/2018
`Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 12th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ.
`2012., p. V5: 3652
`
` from HSDB
`
`Very soluble in ethanol, ethyl ether, carbon disulfide; soluble in acetone; slightly soluble in chloroform; insoluble in ligroin
`Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V1:
`583
`
`16.6 mg/mL
`
`Solubility in water, g/100ml at 20°C: 0.16
`
` from HSDB
`
` from Human Metabolome Database (HMDB)
`
` from ILO-ICSC
`
`4.2.9 Density
`1.091 at 77 deg C/4 deg C
`O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry,
`2013., p. 1352
`
`Density (at 77°C): 1.09 g/cm³
`
`4.2.10 Vapor Pressure
`3.8X10-3 mm Hg at 25 deg C (extrapolated)
`Perry RH, Green D; Perry's Chemical Engineer's Handbook 6th ed New York, NY: McGraw-Hill, Inc p. 3-59 (1984)
`
`Vapour Pressure
`Vapour pressure at 20°C: negligible
`
` from HSDB
`
` from ILO-ICSC
`
` from HSDB
`
` from ILO-ICSC
`
`4.2.11 LogP
`log Kow = 1.41
`Hansch, C., Leo, A., D. Hoekman. Exploring QSAR - Hydrophobic, Electronic, and Steric Constants. Washington, DC: American Chemical
`Society., 1995., p. 41
`
` from HSDB
`
`1.41
`HANSCH,C ET AL. (1995)
`
` from Human Metabolome Database (HMDB)
`
`https://pubchem.ncbi.nlm.nih.gov/compound/phenylacetic_acid
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`1.41
`
`Phenylacetic acid | C8H8O2 - PubChem
`
` from ILO-ICSC
`
`4.2.12 Stability
`Stable under recommended storage conditions.
`Sigma-Aldrich; Safety Data Sheet for Phenylacetic acid. Product Number: P16621, Version 4.6 (Revision Date 04/12/2017). Available
`from, as of June 26, 2017: http://www.sigmaaldrich.com/safety-center.html
`
`4.2.13 Auto-Ignition
`543°C
`
` from HSDB
`
` from ILO-ICSC
`
`4.2.14 Decomposition
`Hazardous decomposition products formed under fire conditions: Carbon oxides
`Sigma-Aldrich; Safety Data Sheet for Phenylacetic acid. Product Number: P16621, Version 4.6 (Revision Date 04/12/2017). Available
`from, as of June 26, 2017: http://www.sigmaaldrich.com/safety-center.html
`
` from HSDB
`
`When heated to decomposition it emits acrid smoke and irritating fumes.
`Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ.
`2004., p. 2895
`
` from HSDB
`
`4.2.15 Heat of Combustion
`-3896.7 to -3910 kJ/mol
`NIST; NIST Chemistry WebBook. Phenylacetic Acid (103-82-2). NIST Standard Reference Database No. 69, Feb 2015 Release.
`Washington, DC: US Sec Commerce. Available from, as of June 9, 2017: http://webbook.nist.gov
`
` from HSDB
`
`4.2.16 Heat of Vaporization
`79.1 kJ/mol
`NIST; NIST Chemistry WebBook. Phenylacetic Acid (103-82-2). NIST Standard Reference Database No. 69, Feb 2015 Release.
`Washington, DC: US Sec Commerce. Available from, as of June 9, 2017: http://webbook.nist.gov
`
` from HSDB
`
`4.2.17 pH
`
`https://pubchem.ncbi.nlm.nih.gov/compound/phenylacetic_acid
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`
`Aqueous solutions of phenyl acetic acid are weakly acidic.
`CDC; International Chemical Safety Cards (ICSC) 2012. Atlanta, GA: Centers for Disease Prevention & Control. National Institute for
`Occupational Safety & Health (NIOSH). Ed Info Div. Available from, as of June 12, 2017: http://www.cdc.gov/niosh/ipcs/default.html
` from HSDB
`
`4.2.18 Odor Threshold
`Malodorous substance. Off site odor is the primary environmental concern. The odor threshold is undoubtedly very low
`but is not quantified.
`European Chemicals Bureau; IUCLID Dataset, Phenylacetic acid (103-82-2) (2000 CD-ROM edition).
`
` from HSDB
`
`4.2.19 Dissociation Constants
`pKa = 4.31
`Haynes, W.M. (ed.). CRC Handbook of Chemistry and Physics. 95th Edition. CRC Press LLC, Boca Raton: FL 2014-2015, p. 5-100
` from HSDB
`
`4.2.20 Relative Evaporation Rate
`A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 deg
`C
`
`CDC; International Chemical Safety Cards (ICSC) 2012. Atlanta, GA: Centers for Disease Prevention & Control. National Institute for
`Occupational Safety & Health (NIOSH). Ed Info Div. Available from, as of June 12, 2017: http://www.cdc.gov/niosh/ipcs/default.html
` from HSDB
`
`4.2.21 Kovats Retention Index
`
`Standard non-polar
`
`Semi-standard non-polar
`
`Standard polar
`
`4.3 Spectral Properties
`
`1251, 1240, 1269, 1252, 1233, 1230, 1236, 1212, 1236, 1236, 1236.8, 216.16
`1246.2, 1265.9, 1254, 1276, 1262, 1248, 1262, 1263, 1255, 1265, 1246, 1248, 1256,
`1265, 1274, 1267, 1263, 1265, 1265, 1263, 1262, 1269, 1269, 1269, 1268, 1270, 1262,
`1262, 1252, 1262, 1262, 1276, 1279, 1251, 1257, 1257, 1257, 1262, 1249, 1249, 1249,
`1249, 1262, 1264, 1262
`2561, 2565, 2585, 2540, 2554, 2543, 2569, 2582, 2581, 2556, 2561, 2569, 2578, 2581,
`2589, 2590, 2548, 2574, 2557, 2519, 2540, 2570, 2570, 2578, 2555, 2569, 2530, 2568,
`2570, 2569, 2573, 2595, 2550, 2550, 2521, 2568, 2528, 2545, 2560, 2553, 2560, 2574,
`2551, 2519, 2564, 2566, 2551, 2577, 2539, 2550, 2550, 2578, 2553, 2553, 2548, 2592,
`2601, 2601, 2551, 2585, 2585, 2575, 2597, 2548, 2548, 2585, 2571, 2565, 2571, 2569,
`2546, 2534, 2534, 2550, 2568, 2568, 2568, 2538, 2610, 2555
`
` from NIST
`
`https://pubchem.ncbi.nlm.nih.gov/compound/phenylacetic_acid
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`
`MAX ABSORPTION (ALCOHOL): 247.5, 258.5 & 267.5 NM (SHOULDER) (LOG E= 2.05, 2.26 & 1.85); SADTLER REFERENCE
`NUMBER: 1655 (IR, PRISM); 474 (UV); 117 (NMR)
`Weast, R.C. (ed.). Handbook of Chemistry and Physics. 60th ed. Boca Raton, Florida: CRC Press Inc., 1979., p. C-97
`
` from HSDB
`
`MASS: 21060 (NIST/EPA/MSDC Mass Spectral database, 1990 version)
`Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V1:
`583
`
` from HSDB
`
`IR: 320 (Coblentz Society spectral collection)
`Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V1:
`583
`
` from HSDB
`
`UV: 474 (Sadtler Research Laboratories spectral collection)
`Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V1:
`583
`
` from HSDB
`
`Raman: 806 (Sadtler Research Laboratories spectral collection)
`Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V1:
`583
`
` from HSDB
`
`1H NMR: 117 (Sadtler Research Laboratories spectral collection)
`Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V1:
`583
`
` from HSDB
`
`4.3.1 Infrared Spectra
`
`Infrared Spectra: 1 of 7 (FTIR Spectra)
`Instrument Name
`Bruker Tensor 27 FT-IR
`Technique
`KBr0
`Source of Spectrum
`Bio-Rad Laboratories, Inc.
`Source of Sample
`Spectrochem Pvt. Ltd.
`Catalog Number
`116138
`Copyright
`Copyright © 2018 Bio-Rad Laboratories, Inc. All Rights Reserved.
`
`https://pubchem.ncbi.nlm.nih.gov/compound/phenylacetic_acid
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`Infrared Spectra: 1 of 7 (FTIR Spectra)
`
`Phenylacetic acid | C8H8O2 - PubChem
`
`CLICK TO LOAD...
`
`Thumbnail
`
` from SpectraBase
`
`Infrared Spectra: 2 of 7 (FTIR Spectra)
`Technique
`CAPILLARY CELL: MELT
`Source of Sample
`Fritzsche Brothers, Inc., New York, New York
`Copyright
`Copyright © 1980, 1981-2018 Bio-Rad Laboratories, Inc. All Rights Reserved.
`
`CLICK TO LOAD...
`
`Thumbnail
`
` from SpectraBase
`
`Infrared Spectra: 3 of 7 (FTIR Spectra)
`Technique
`KBr WAFER
`Source of Sample
`Eastman Kodak Company, Rochester, New York
`Copyright
`Copyright © 1980, 1981-2018 Bio-Rad Laboratories, Inc. All Rights Reserved.
`
`CLICK TO LOAD...
`
`Thumbnail
`
`https://pubchem.ncbi.nlm.nih.gov/compound/phenylacetic_acid
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` from SpectraBase
`
`View All 7 Infrared Spectra
`
`4.3.2 1D NMR Spectra
`
`1D NMR Spectra: 1 of 12 (1H NMR Spectra)
`1. 1D NMR Spectrum 1195 - Varian 600 MHz 1H NMR
`2. 1D NMR Spectrum 4993 - Bruker 1H NMR
`
`1H NMR Spectra
`
`13C NMR Spectra
`
`1. 1D NMR Spectrum 1204 - Bruker 400 MHz 13C NMR
`2. 1D NMR Spectrum 2772 - NEVA 15.09 MHz 13C NMR
`3. 1D NMR Spectrum 4994 - Bruker 13C NMR
`
` from Human Metabolome Database (HMDB)
`
`1D NMR Spectra: 2 of 12 (17O NMR Spectra)
`Copyright © 2016 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights
`Reserved.
`
`Copyright
`
`CLICK TO LOAD...
`
`Thumbnail
`
`1D NMR Spectra: 3 of 12 (13C NMR Spectra)
`Copyright © 2016 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights
`Reserved.
`
`Copyright
`
`CLICK TO LOAD...
`
` from SpectraBase
`
`Thumbnail
`
`https://pubchem.ncbi.nlm.nih.gov/compound/phenylacetic_acid
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` from SpectraBase
`
`View All 12 1D NMR Spectra
`
`4.3.3 2D NMR Spectra
`
`2D NMR Spectra: 1 of 1 (1H-13C NMR Spectra)
`1H-13C NMR Spectra
`2D NMR Spectrum 1208 - Bruker 600 MHz 1H-13C HSQC
`
` from Human Metabolome Database (HMDB)
`
`4.3.4 Mass Spectrometry
`
`4.3.4.1 General MS
`
`General MS: 1 of 5 (MS)
`MoNA ID
`MS Type
`MS Level
`Instrument
`Instrument Type
`Ionization Mode
`Splash
`
`Thumbnail
`
`JP009209
`Chromatography identified as GC-MS
`MS1
`HITACHI M-80B
`EI-B
`positive
`splash10-0006-9100000000-de65c7c0092343a4e599
`
`CLICK TO LOAD...
`
`Submitter
`
`Kimito Funatsu, Graduate School of Engineering, The University of Tokyo
`
` from MassBank of North America (MoNA)
`
`General MS: 2 of 5 (MS)
`MoNA ID
`MS Type
`MS Level
`
`MT000056
`Chromatography identified as LC-MS
`MS2
`
`https://pubchem.ncbi.nlm.nih.gov/compound/phenylacetic_acid
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`General MS: 2 of 5 (MS)
`Precursor Type
`precursor m/z
`Instrument
`Instrument Type
`Ionization
`Ionization Mode
`Splash
`
`Thumbnail
`
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`[M-H]-
`135.1
`LTQ XL, Thermo Finnigan
`LC-ESI-IT
`ESI
`negative
`splash10-0006-9000000000-6ca33b098558bf13801c
`
`CLICK TO LOAD...
`
`Submitter
`
`A.M. Evans, Metabolon, Inc.
`
` from MassBank of North America (MoNA)
`
`General MS: 3 of 5 (MS)
`MoNA ID
`MS Type
`MS Level
`Precursor Type
`precursor m/z
`Instrument
`Ionization Mode
`Splash
`
`Thumbnail
`
`CCMSLIB00000578367
`Chromatography identified as LC-MS
`MS2
`M-H
`135.045
`Q-Exactive Plus
`negative
`splash10-000i-0900000000-f898aafe4cecc87d26f1
`
`CLICK TO LOAD...
`
`https://pubchem.ncbi.nlm.nih.gov/compound/phenylacetic_acid
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`General MS: 3 of 5 (MS)
`Submitter
`
`View All 5 General MS
`
`Phenylacetic acid | C8H8O2 - PubChem
`
`GNPS Collaboration, University of California, San Diego
`
` from MassBank of North America (MoNA)
`
`4.3.4.2 GC-MS
`1. GC-MS Spectrum 1016 - GC-MS (1 TMS)
`2. GC-MS Spectrum 2640 - GC-MS Ei Predicted by CFMID-EI, energy0
`3. GC-MS Spectrum 29481 - EI-B positive instrument=HITACHI M-80B
`4. GC-MS Spectrum 31075 - GC-MS
`5. GC-MS Spectrum 31879 - GC-EI-TOF positive instrument=Leco Pegasus IV
`6. GC-MS Spectrum 37358 - GC-MS Ei (1 TMS) Predicted by CFMID-EI, Ionization energy 70 eV fully TMS-derivatized
`(structure: C[Si](C)(C)OC(=O)CC1=CC=CC=C1)
`
` from Human Metabolome Database (HMDB)
`
`
`
`
`
`352514
`Main library
`57
`91
`136
`92
`
`CLICK TO LOAD...
`
`1 of 5
`
`
`NIST Number
`Library
`Total Peaks
`m/z Top Peak
`m/z 2nd Highest
`m/z 3rd Highest
`
`Thumbnail
`
`4.3.4.3 MS-MS
`1. MS-MS Spectrum 6130 - EI-B (HITACHI M-80B) Positive
`2. MS-MS Spectrum 178593 - 10V Positive Predicted by CFM-ID
`
`https://pubchem.ncbi.nlm.nih.gov/compound/phenylacetic_acid
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` from NIST
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`3. MS-MS Spectrum 178594 - 20V Positive Predicted by CFM-ID
`4. MS-MS Spectrum 178595 - 40V Positive Predicted by CFM-ID
`5. MS-MS Spectrum 180912 - 10V Negative Predicted by CFM-ID
`6. MS-MS Spectrum 180913 - 20V Negative Predicted by CFM-ID
`7. MS-MS Spectrum 180914 - 40V Negative Predicted by CFM-ID
`8. MS-MS Spectrum 438658 - LC-ESI-IT negative instrument=LTQ XL, Thermo Finnigan
`9. MS-MS Spectrum 440176 - negative instrument=Q-Exactive Plus
`
` from Human Metabolome Database (HMDB)
`
`
`
`
`
`1021082
`IT/ion trap
`MS2
`[M-H]-
`135.0452
`3
`91
`92
`135
`
`CLICK TO LOAD...
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`1 of 3
`
`
`NIST Number
`Instrument Type
`Spectrum Type
`Precursor Type
`Precursor m/z
`Total Peaks
`m/z Top Peak
`m/z 2nd Highest
`m/z 3rd Highest
`
`Thumbnail
`
`4.3.4.4 EI-MS
`EI-MS Spectrum 436 -
`
`4.3.5 Other Spectra
`
` from NIST
`
` from Human Metabolome Database (HMDB)
`
`Other Spectra: 1 of 1 (Raman Spectra)
`Instrument Name
`Bruker MultiRAM Stand Alone FT-Raman Spectrometer
`https://pubchem.ncbi.nlm.nih.gov/compound/phenylacetic_acid
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`Other Spectra: 1 of 1 (Raman Spectra)
`Technique
`FT-Raman
`Source of Spectrum
`Bio-Rad Laboratories
`Source of Sample
`Spectrochem Pvt. Ltd., India
`Catalog Number
`116138
`Copyright
`Copyright © 2014-2018 Bio-Rad Laboratories, Inc. All Rights Reserved.
`
`CLICK TO LOAD...
`
`Thumbnail
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` from SpectraBase
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`https://pubchem.ncbi.nlm.nih.gov/compound/phenylacetic_acid
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`5 Related Records
`
`5.1 Related Compounds with Annotation
`
`CLICK TO LOAD...
`
`5.2 Related Compounds
`
`Same Tautomer
`Same Connectivity
`Same Parent, Tautomer
`Same Parent, Connectivity
`Same Parent, Exact
`Mixtures, Components, and
`Neutralized Forms
`Similar Compounds
`Similar Conformers
`
`19 records
`17 records
`142 records
`138 records
`122 records
`
`470 records
`
`4020 records
`25855 records
`
`5.3 Substances
`
`5.3.1 Related Substances
`
`All
`Same
`Mixture
`
`960 records
`152 records
`808 records
`
` from PubChem
`
` from PubChem
`
` from PubChem
`
`https://pubchem.ncbi.nlm.nih.gov/compound/phenylacetic_acid
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`5.3.2 Substances by Category
`
`CLICK TO LOAD...
`
`5.4 Entrez Crosslinks
`
`PubMed
`Protein Structures
`Taxonomy
`OMIM
`Gene
`
`786 records
`8 records
`2 records
`1 record
`6 records
`
` from PubChem
`
` from PubChem
`
`https://pubchem.ncbi.nlm.nih.gov/compound/phenylacetic_acid
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`6 Chemical Vendors
`
`CLICK TO LOAD...
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` from PubChem
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`https://pubchem.ncbi.nlm.nih.gov/compound/phenylacetic_acid
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`7 Drug and Medication Information
`
`7.1 Drug Indication
`For use as adjunctive therapy for the treatment of acute hyperammonemia and associated encephalopathy in patients
`with deficiencies in enzymes of the urea cycle.
`
`7.2 Clinical Trials
`
`1 to 1 of 1
`Record ID
`NCT00003241
`
`Title
`Phenylacetate in Treating Children With Recurrent or Progressive Brain Tumors
`
` from DrugBank
`
` Download
`
`Phase
`Status
`2
`Completed
` from ClinicalTrials.gov
`
`https://pubchem.ncbi.nlm.nih.gov/compound/phenylacetic_acid
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`8 Food Additives and Ingredients
`
`8.1 Food Additive Classes
`Flavoring Agents
`
`JECFA Functional Classes
`Flavouring Agent: FLAVOURING_AGENT
`
`8.2 FEMA Flavor Profile
`Caramel, Floral, Flower, Honey
`
` from EU Food Improvement Agents
`
` from FAO/WHO Food Additive Evaluations (JECFA)
`
` from Flavor and Extract Manufacturers Association (FEMA)
`
`8.3 Evaluations of the Joint FAO/WHO Expert Committee on Food Additives - JECFA
`
`Evaluations of the Joint FAO/WHO Expert Committee on Food Additives - JECFA: 1 of 1 (JECFA Chemical)
`Chemical Name
`alpha-TOLUIC ACID
`ADI
`No safety concern at current levels of intake when used as a flavouring agent
`Evaluation Year
`2002
`Report
`TRS 913-JECFA 59/53
`
` from FAO/WHO Food Additive Evaluations (JECFA)
`
`https://pubchem.ncbi.nlm.nih.gov/compound/phenylacetic_acid
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`9 Pharmacology and Biochemistry
`
`9.1 MeSH Pharmacological Classification
`
`Antimetabolites, Antineoplastic
`Antimetabolites that are useful in cancer chemotherapy.
`See a list of PubChem compounds matching this category.
`
`9.2 FDA Pharmacological Classification
`
`9.2.1 Active Moiety
`PHENYLACETIC ACID
`
`9.2.2 FDA UNII
`ER5I1W795A
`
`9.2.3 Pharmacological Classes
`
`Mechanisms of Action [MoA]
`Established Pharmacologic
`Class [EPC]
`
`Ammonium Ion Binding Activity
`
`Nitrogen Binding Agent
`
`9.3 Absorption, Distribution and Excretion
`
`Volume of Distribution
`19.2 ± 3.3 L.
`
` from MeSH
`
` from FDA Pharm Classes
`
` from FDA Pharm Classes
`
` from FDA Pharm Classes
`
` from DrugBank
`
`... Although exhaled volatile organic compound (VOC) patterns change in obstructive sleep apnea (OSA) patients,
`individual VOC profiles are not fully determined. The primary outcome was VOC characterizations; secondary outcomes
`included their relationships with sleep and clinical parameters in OSA patients. We prospectively examined 32 OSA
`patients with an apnea-hypopnea index (AHI) >/= 15 by full polysomnography, and 33 age- and sex-matched controls
`without obvious OSA symptoms. Nine severe OSA patients were examined before and after continuous positive airway
`pressure (CPAP) treatment. By applying a method which eliminates environmental VOC influences, exhaled VOCs were
`identified by gas chromatography (GC)-mass spectrometry, and their concentrations were determined by GC. Exhaled
`aromatic hydrocarbon concentrations (toluene, ethylbenzene, p-xylene, and phenylacetic acid) in the severe OSA groups
`https://pubchem.ncbi.nlm.nih.gov/compound/phenylacetic_acid
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`(AHI >/= 30) and exhaled saturated hydrocarbon concentrations (hexane, heptane, octane, nonane, and decane) in the
`most severe OSA group (AHI >/= 60) were higher than those in the control group. Exhaled isoprene concentrations were
`increased in all OSA groups (AHI >/= 15); acetone concentration was increased in the most severe OSA group.
`Ethylbenzene, p-xylene, phenylacetic acid, and nonane concentrations were increased according to OSA severity, and
`correlated with AHI, arousal index, and duration of percutaneous oxygen saturation (SpO2) </= 90%. Multiple regression
`analyses revealed these 4 VOC levels were associated with the duration of SpO2 </= 90%. Isoprene and acetone
`decreased after CPAP treatment. OSA increased some toxic VOCs, and some correlated with OSA severity. CPAP treatment
`possibly ameliorates these productions.
`Abstract: PubMed
`Aoki T et al; Toxicol Sci 156 (2): 362-374 (2017)
`
` from HSDB
`
`The dose limiting toxicity and pharmacokinetics of phenylacetic acid (phenylacetate) were studied in 17 patients with
`advanced solid tumors who received single iv bolus doses followed by a 14 day continuous iv infusion of the drug in a
`phase I trial. Phenylacetic acid displayed nonlinear pharmacokinetics with evidence for induction of drug clearance.
`Ninety-nine percent of phenylacetic acid elimination was accounted for by conversion to phenylacetylglutamine which
`was excreted in the urine...
`Abstract: PubMed
`Thibault A et al; Cancer Res 54: 1690-94 (1994)
`
` from HSDB
`
`Phenylacetic acid... /is/ rapidly absorbed from human buccal tissues or membranes.
`National Research Council. Drinking Water & Health Volume 1. Washington, DC: National Academy Press, 1977., p. 754
` from HSDB
`
`Man excreted 93%...as glutamine conjugate... . New world monkeys excreted conjugates of glutamine, glycine and taurine,
`while old world species excreted large proportion of free acid and only glutamine