Record Information
Version2.0
Creation Date2012-08-09 09:16:12 -0600
Update Date2015-09-13 12:56:16 -0600
Secondary Accession Numbers
  • ECMDB21426
Identification
Name:Phenyllactic acid
DescriptionPhenyllactic acid is a lactic acid in which one of the methyl hydrogens is substituted by a phenyl group. Phenyllactic acid (or 3-phenyllactic acid) has two stereoisomers: (R)-3-phenyllactic acid and (S)-3-phenyllactic acid. (ChEBI) Phenyllactic acid is also similar in structure to the amino acid phenylalanine, except with the amino group in phenylalanine replaced by a hydroxyl group. (inferred from compound structure)
Structure
Thumb
Synonyms:
  • 2-Hydroxy-3-phenylpropanoate
  • 2-Hydroxy-3-phenylpropanoic acid
  • 2-Hydroxy-3-phenylpropionate
  • 2-Hydroxy-3-phenylpropionic acid
  • 3-Phenyl-2-hydroxypropanoate
  • 3-Phenyl-2-hydroxypropanoic acid
  • 3-Phenyllactate
  • 3-Phenyllactic acid
  • A-Hydroxybenzenepropanoate
  • A-Hydroxybenzenepropanoic acid
  • Alpha-Hydroxybenzenepropanoate
  • Alpha-Hydroxybenzenepropanoic acid
  • B-Phenyllactate
  • b-Phenyllactic acid
  • Beta-Phenyllactate
  • Beta-Phenyllactic acid
  • DL-2-Hydroxy-3-phenylpropionate
  • DL-2-Hydroxy-3-phenylpropionic acid
  • DL-3-Phenyllactate
  • DL-3-Phenyllactic acid
  • DL-b-Phenyllactate
  • DL-b-Phenyllactic acid
  • DL-beta-Phenyllactate
  • DL-beta-Phenyllactic acid
  • DL-β-Phenyllactate
  • DL-β-Phenyllactic acid
  • Phenyllactate
  • α-Hydroxybenzenepropanoate
  • α-Hydroxybenzenepropanoic acid
  • β-Phenyllactate
  • β-Phenyllactic acid
Chemical Formula:C9H10O3
Weight:Average: 166.1739
Monoisotopic: 166.062994186
InChI Key:VOXXWSYKYCBWHO-UHFFFAOYSA-N
InChI:InChI=1S/C9H10O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8,10H,6H2,(H,11,12)
CAS number:828-01-3
IUPAC Name:2-hydroxy-3-phenylpropanoic acid
Traditional IUPAC Name:β-phenyllactic acid
SMILES:OC(CC1=CC=CC=C1)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Hydroxy acid
  • Monocyclic benzene moiety
  • Alpha-hydroxy acid
  • Tertiary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-1
Melting point:98 °C
Experimental Properties:
PropertyValueSource
LogP:1.83 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility9.8 g/LALOGPS
logP0.84ALOGPS
logP1.18ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)4.02ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity43.46 m³·mol⁻¹ChemAxon
Polarizability16.7 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0006-2930000000-9c44eea65a6e20c158eeView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0006-2930000000-9c44eea65a6e20c158eeView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0007-1910000000-1c581a4eacd9a7f2036fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-750e52d0df9e2b90be09View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-006x-9540000000-c06e2865c7cf1c780f11View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-cfbc3d9f0107a37ad7f7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00kb-1900000000-e1937415e710a88af8dbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0v4i-4900000000-f7887dfe1f265bcf46baView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0v4i-6900000000-7df2fcf2f9b049e4c39fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0v00-6900000000-992cb5008b3e748b7e66View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-cfbc3d9f0107a37ad7f7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00kb-1900000000-a9ac61820c9f5278e2baView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0v4i-4900000000-5e5e2d29a299435f9b35View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0v4i-6900000000-7df2fcf2f9b049e4c39fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0v00-6900000000-992cb5008b3e748b7e66View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0002-0900000000-8940947cbb9a8e6253eeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00si-9600000000-6ba02da72bb3acc762dfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0089-9700000000-901ab7fc4dce05d16406View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-017i-9100000000-248f4ab6119fb2bb911cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1900000000-37469cb4526a3ed239e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01bd-4900000000-f70272565fdcdbdf5209View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9400000000-14afa00d4a96d888572bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-3900000000-15a50bcc903d54af3f43View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9400000000-0d7b49d15700ae266645View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-ca99933d289067e5347aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0900000000-a96f38f47d5e070f0989View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006t-1900000000-82f893f2df7cfa6f88ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f96-9400000000-50e3d4b82e667ef9e4d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-5900000000-eb26ccce038261968168View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9300000000-aa44337c740dacf05e9cView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Iijima S, Ishii A, Miyakoshi T, Odaira T, Musha M: Studies on the experimental phenylketonuria in rats. Tohoku J Exp Med. 1975 Oct;117(2):167-78. Pubmed: 1209606
  • Sarkissian CN, Scriver CR, Mamer OA: Measurement of phenyllactate, phenylacetate, and phenylpyruvate by negative ion chemical ionization-gas chromatography/mass spectrometry in brain of mouse genetic models of phenylketonuria and non-phenylketonuria hyperphenylalaninemia. Anal Biochem. 2000 May 1;280(2):242-9. Pubmed: 10790306
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID25998
HMDB IDHMDB00779
Pubchem Compound ID643327
Kegg IDC05607
ChemSpider ID3715
Wikipedia IDNot Available
BioCyc IDNot Available