3-(4-hydroxyphenyl)lactic acid (YMDB00457)

Identification
YMDB IDYMDB00457
Name3-(4-hydroxyphenyl)lactic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionHydroxyphenyllactic acid, also known as 4-hydroxyphenyllactate or HPLA, belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. Hydroxyphenyllactic acid exists in all eukaryotes, ranging from yeast to plants to humans. Based on a literature review a significant number of articles have been published on Hydroxyphenyllactic acid.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (RS)-3-(4-Hydroxyphenyl)lactate
  • (RS)-3-(4-Hydroxyphenyl)lactic acid
  • 2-Hydroxy-3-(4-hydroxyphenyl)propanoate
  • 2-Hydroxy-3-(4-hydroxyphenyl)propanoic acid
  • 2-Hydroxy-3-(p-hydroxyphenyl)propionate
  • 2-Hydroxy-3-(p-hydroxyphenyl)propionic acid
  • 3-(4-Hydroxyphenyl)-DL-lactate
  • 3-(4-Hydroxyphenyl)-DL-lactic acid
  • 3-(4-Hydroxyphenyl)lactate
  • 3-(4-Hydroxyphenyl)lactic acid
  • 3-(p-hydroxyphenyl)-Lactate
  • 3-(p-hydroxyphenyl)-Lactic acid
  • 4-Hydroxyphenyllactate
  • 4-Hydroxyphenyllactic acid
  • a,4-Dihydroxybenzenepropanoate
  • a,4-Dihydroxybenzenepropanoic acid
  • b-(4-Hydroxyphenyl)lactate
  • b-(4-Hydroxyphenyl)lactic acid
  • b-(p-Hydroxyphenyl)-DL-lactate
  • b-(p-Hydroxyphenyl)-DL-lactic acid
  • b-(p-Hydroxyphenyl)lactate
  • b-(p-Hydroxyphenyl)lactic acid
  • Benzenepropanoic acid, .alpha.,4-dihydroxy-
  • beta-(4-Hydroxyphenyl)lactate
  • beta-(4-Hydroxyphenyl)lactic acid
  • beta-(p-Hydroxyphenyl)-DL-lactate
  • beta-(p-Hydroxyphenyl)-DL-lactic acid
  • beta-(p-Hydroxyphenyl)lactate
  • beta-(p-Hydroxyphenyl)lactic acid
  • DL-3-(4-Hydroxyphenyl)lactate
  • DL-3-(4-Hydroxyphenyl)lactic acid
  • DL-p-Hydroxyphenyllactate
  • DL-p-Hydroxyphenyllactic acid
  • HPLA
  • Hydroxyphenyllactate
  • Lactic acid, (p-hydroxyphenyl)-
  • Lactic acid, 3-(p-hydroxyphenyl)-
  • p-Hydroxyphenyl lactic acid
  • p-Hydroxyphenyllactate
  • Β-(4-hydroxyphenyl)lactate
  • Β-(4-hydroxyphenyl)lactic acid
  • Β-(p-hydroxyphenyl)lactate
  • Β-(p-hydroxyphenyl)lactic acid
  • p-Hydroxyphenyl lactate
  • p-Hydroxyphenyllactic acid
  • 4-Hydroxyphenyllactic acid, (DL)-isomer
  • Para-hydroxyphenyllactic acid
  • 2-Hydroxyphloretate
  • 2-Hydroxy-3-(4'-hydroxyphenyl)propanoic acid
  • 2-Hydroxy-3-(4'-hydroxyphenyl)propanoic acid
CAS number306-23-0
WeightAverage: 182.1733
Monoisotopic: 182.057908808
InChI KeyJVGVDSSUAVXRDY-UHFFFAOYSA-N
InChIInChI=1S/C9H10O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8,10-11H,5H2,(H,12,13)
IUPAC Name2-hydroxy-3-(4-hydroxyphenyl)propanoic acid
Traditional IUPAC Namehydroxyphenyllactic acid
Chemical FormulaC9H10O4
SMILESOC(CC1=CC=C(O)C=C1)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassPhenylpropanoic acids
Sub ClassNot Available
Direct ParentPhenylpropanoic acids
Alternative Parents
Substituents
  • 3-phenylpropanoic-acid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Alpha-hydroxy acid
  • Monocyclic benzene moiety
  • Benzenoid
  • Hydroxy acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water Solubility12.9 mg/mL at 16 oC [BEILSTEIN]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility4.79 g/LALOGPS
logP0.87ALOGPS
logP0.88ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)3.58ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.44 m³·mol⁻¹ChemAxon
Polarizability17.51 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Mitochondrion
Organoleptic PropertiesNot Available
SMPDB Pathways
Tyrosine metabolismPW002441 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Tyrosine metabolismec00350 Map00350
Ubiquinone and other terpenoid-quinone biosynthesisec00130 Map00130
SMPDB ReactionsNot Available
KEGG Reactions
NADH + (4-hydroxyphenyl)pyruvic acid + hydron → NAD + 3-(4-hydroxyphenyl)lactic acid
3-(4-hydroxyphenyl)lactic acid → water + trans-4-Coumaric acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-004i-1911000000-424dc0a114976e4a6052JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004i-1911000000-424dc0a114976e4a6052JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-0900000000-b7f0ddb24f5c187d4540JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4r-3900000000-aece5a68ba54ab74c5eeJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-003r-5496000000-fbb65d0c963e70625e95JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00li-2900000000-ea59f9dcf58b55bec6caJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-054n-9300000000-5b39aa5183630ccd7f4dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0k92-9200000000-c698fdbe1eefac6e9eabJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-01qi-0900000000-640a5a477752571a1443JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-03di-0900000000-45b5f23bae1a9641fb0bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-01qi-0900000000-640a5a477752571a1443JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-03ei-0900000000-d89828d3625adabd215bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-00ou-9000000000-60dd6237cac5c79c7508JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00ri-2900000000-69365cb4d9937f6a96e0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-00li-1900000000-03a7d2e8f219eba66eeeJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-029i-0900000000-fd70bef080a1a354df5aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-9400000000-65da3c598368dbad66cdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-052b-9100000000-6ad54b488ac0183ff4bfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-9400000000-af41107b1e7be38f765cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-023a994f4d18e32123cdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-001i-5900000000-8fcf87adaaae828f3aaeJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00ri-2900000000-ed974245d122fcbc31c0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-03ei-1900000000-fd1d5ff4f32cdcdf0a38JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00ec-9400000000-9b26dc9e6bb4e1a72cfbJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05o9-0900000000-a343595d5c411e940c25JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ap0-0900000000-1f777ab6b9486c181355JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9800000000-db82c9bf8afdb32af6deJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2900000000-3e1a7023e9214816e8a5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-2900000000-c05e995d8c57a180bae7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mx-9800000000-729b43ad9499a14c2d01JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Synthesis Reference:Deng, Xi-ling; Wang, Xin-bing; Xiang, Ying; Zhu, Shi-fa. Synthesis of b-(4-hydroxyphenyl)lactic acid. Shihezi Daxue Xuebao, Ziran Kexueban (2005), 23(1), 11-13.
External Links:
ResourceLink
CHEBI ID17385
HMDB IDHMDB00755
Pubchem Compound ID9378
Kegg IDC03672
ChemSpider ID9010
FOODB IDFDB017136
Wikipedia IDNot Available
BioCyc IDCPD-6978