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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 is an extremely weak basic (essentially neutral) compound (based on its pKa). Hydroxyphenyllactic acid exists in all eukaryotes, ranging from yeast to humans. Hydroxyphenyllactic acid is a potentially toxic compound.
  • (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
CAS number306-23-0
WeightAverage: 182.1733
Monoisotopic: 182.057908808
IUPAC Name2-hydroxy-3-(4-hydroxyphenyl)propanoic acid
Traditional IUPAC Namehydroxyphenyllactic acid
Chemical FormulaC9H10O4
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
  • 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
Melting pointNot Available
Experimental Properties
Water Solubility12.9 mg/mL at 16 oC [BEILSTEIN]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
Water Solubility4.79 g/LALOGPS
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
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 + hydronNAD + 3-(4-hydroxyphenyl)lactic acid
3-(4-hydroxyphenyl)lactic acidwater + trans-4-Coumaric acid
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
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
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
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
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
  • 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:
Pubchem Compound ID9378
Kegg IDC03672
ChemSpider ID9010
Wikipedia IDNot Available
BioCyc IDCPD-6978