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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-07 01:19:31 UTC
HMDB IDHMDB0000755
Secondary Accession Numbers
  • HMDB00755
Metabolite Identification
Common NameHydroxyphenyllactic acid
DescriptionHydroxyphenyllactic acid or 4-hydroxyphenyllactate (the L-form) is a tyrosine metabolite. The level of L-hydroxyphenyllactic acid is elevated in patients with a deficiency of the enzyme p-hydroxyphenylpyruvate oxidase (EC 1.14.2.2) (PMID 4720815 ). L-hydroxyphenyllactate is present in relatively higher concentrations in the cerebrospinal fluid and urine of patients with phenylketonuria (PKU) and tyrosinemia (PMID: 3126358 ). However the D-form of hydroxyphneyllactate is of bacterial origin and is also found in individuals with bacterial overgrowth or unusual gut microflora (PMID: 3126358 ). Microbial hydroxyphenyllactate is likely derived from phenolic or polyphenolic compounds in the diet. Bifidobacteria and lactobacilli produced considerable amounts of phenyllactic and p-hydroxyphenyllactic acids (PMID: 23061754 ). It has also been shown that hydroxyphenyllactate decreases ROS (reactive oxygen species) production in both mitochondria and neutrophils and so hydroxyphenyllactate may function as a natural anti-oxidant (PMID: 23061754 ).
Structure
Thumb
Synonyms
ValueSource
2-Hydroxy-3-(4-hydroxyphenyl)propanoateChEBI
2-Hydroxy-3-(P-hydroxyphenyl)propionic acidChEBI
4-Hydroxyphenyllactic acidChEBI
beta-(4-Hydroxyphenyl)lactic acidChEBI
beta-(P-Hydroxyphenyl)lactic acidChEBI
DL-P-Hydroxyphenyllactic acidChEBI
P-Hydroxyphenyl lactic acidChEBI
2-Hydroxy-3-(4-hydroxyphenyl)propanoic acidGenerator
HydroxyphenyllactateGenerator
2-Hydroxy-3-(P-hydroxyphenyl)propionateGenerator
4-HydroxyphenyllactateGenerator
b-(4-Hydroxyphenyl)lactateGenerator
b-(4-Hydroxyphenyl)lactic acidGenerator
beta-(4-Hydroxyphenyl)lactateGenerator
β-(4-hydroxyphenyl)lactateGenerator
β-(4-hydroxyphenyl)lactic acidGenerator
b-(P-Hydroxyphenyl)lactateGenerator
b-(P-Hydroxyphenyl)lactic acidGenerator
beta-(P-Hydroxyphenyl)lactateGenerator
β-(P-hydroxyphenyl)lactateGenerator
β-(P-hydroxyphenyl)lactic acidGenerator
DL-P-HydroxyphenyllactateGenerator
P-Hydroxyphenyl lactateGenerator
(RS)-3-(4-Hydroxyphenyl)lactateHMDB
(RS)-3-(4-Hydroxyphenyl)lactic acidHMDB
3-(4-Hydroxyphenyl)-DL-lactateHMDB
3-(4-Hydroxyphenyl)-DL-lactic acidHMDB
3-(4-Hydroxyphenyl)lactateHMDB
3-(4-Hydroxyphenyl)lactic acidHMDB
3-(P-Hydroxyphenyl)-lactateHMDB
3-(P-Hydroxyphenyl)-lactic acidHMDB
a,4-DihydroxybenzenepropanoateHMDB
a,4-Dihydroxybenzenepropanoic acidHMDB
b-(P-Hydroxyphenyl)-DL-lactateHMDB
b-(P-Hydroxyphenyl)-DL-lactic acidHMDB
beta-(P-Hydroxyphenyl)-DL-lactateHMDB
beta-(P-Hydroxyphenyl)-DL-lactic acidHMDB
DL-3-(4-Hydroxyphenyl)lactateHMDB
DL-3-(4-Hydroxyphenyl)lactic acidHMDB
HPLAHMDB
4-Hydroxyphenyllactic acid, (DL)-isomerMeSH
Para-hydroxyphenyllactic acidMeSH
P-HydroxyphenyllactateMeSH
Chemical FormulaC9H10O4
Average Molecular Weight182.1733
Monoisotopic Molecular Weight182.057908808
IUPAC Name2-hydroxy-3-(4-hydroxyphenyl)propanoic acid
Traditional Namehydroxyphenyllactic acid
CAS Registry Number306-23-0
SMILES
OC(CC1=CC=C(O)C=C1)C(O)=O
InChI Identifier
InChI=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)
InChI KeyJVGVDSSUAVXRDY-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as phenylpropanoic acids. These are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomChemical entities
Super ClassOrganic compounds
ClassPhenylpropanoids and polyketides
Sub ClassPhenylpropanoic acids
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
Ontology
Physiological effect

Health effect:

  Health condition:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Biological Location:

  Biofluid and excreta:

  Tissue and substructures:

  Organ and components:

Source:

Role

Indirect biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility12.9 mg/mL at 16 °CNot Available
LogPNot AvailableNot Available
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
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-004i-1911000000-424dc0a114976e4a6052View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004i-1911000000-424dc0a114976e4a6052View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-0900000000-b7f0ddb24f5c187d4540View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4r-3900000000-aece5a68ba54ab74c5eeView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-003r-5496000000-fbb65d0c963e70625e95View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00li-2900000000-ea59f9dcf58b55bec6caView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-054n-9300000000-5b39aa5183630ccd7f4dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0k92-9200000000-c698fdbe1eefac6e9eabView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-01qi-0900000000-640a5a477752571a1443View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-03di-0900000000-45b5f23bae1a9641fb0bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-01qi-0900000000-640a5a477752571a1443View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-03ei-0900000000-d89828d3625adabd215bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05o9-0900000000-a343595d5c411e940c25View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ap0-0900000000-1f777ab6b9486c181355View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9800000000-db82c9bf8afdb32af6deView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2900000000-3e1a7023e9214816e8a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-2900000000-c05e995d8c57a180bae7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mx-9800000000-729b43ad9499a14c2d01View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Mitochondria
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Location
  • Epidermis
  • Prostate
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.64 +/- 0.24 uMAdult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
FecesDetected but not Quantified Infant (0-1 year old)Not Specified
Normal
details
FecesDetected but not Quantified Infant (0-1 year old)Not Specified
Normal
details
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
FecesDetected but not Quantified Children (1-13 years old)BothNormal details
FecesDetected but not Quantified Infant (0-1 year old)Not AvailableNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected and Quantified25.10 +/- 14.93 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
UrineDetected and Quantified17.377 +/- 21.101 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified22.342 +/- 30.410 umol/mmol creatinineInfant (0-1 year old)Both
Normal
details
UrineDetected and Quantified33.513 +/- 76.957 umol/mmol creatinineInfant (0-1 year old)Both
Normal
details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.55-1.2 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified5.393 +/- 4.849 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified35.939 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected and Quantified1.05 +/- 0.43 umol/mmol creatinineAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified1.1 (0.2-2.6) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified3.7 (0.1-11.5) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified4.8 (2.7-5.3) umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified0.51-0.94 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified1.6 (0.3-5.8) umol/mmol creatinineChildren (1-13 years old)Both
Normal
details
UrineDetected and Quantified1.5 (0.1-8.7) umol/mmol creatinineChildren (1-13 years old)Both
Normal
details
UrineDetected and Quantified1.0 (0.4-7.3) umol/mmol creatinineAdolescent (13-18 years old)Both
Normal
details
UrineDetected and Quantified<50.12 umol/mmol creatinineChildren (1 - 18 years old)Both
Normal
    • BC Children's Hos...
details
UrineDetected and Quantified3.2 (1.5-3.9) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified2.8 (2.6-3.0) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.80 +/- 0.10 uMAdult (>18 years old)BothMorphine treatment details
FecesDetected but not Quantified Adult (>18 years old)BothICD details
FecesDetected but not Quantified Adult (>18 years old)BothCCD details
FecesDetected but not Quantified Adult (>18 years old)BothCCD details
FecesDetected but not Quantified Adult (>18 years old)BothICD details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
UrineDetected and Quantified139.639 +/- 122.882 umol/mmol creatinineChildren (1-13 years old)Both
Phenylketonuria
details
UrineDetected and Quantified74.474 +/- 94.334 umol/mmol creatinineChildren (1-13 years old)Both
Phenylketonuria
details
UrineDetected and Quantified75.0948 +/- 98.678 umol/mmol creatinineChildren (1-13 years old)BothPhenylketonuria details
UrineDetected and Quantified5.879 +/- 5.443 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified8.512 +/- 4.226 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Mordechai, Hien, ...
details
UrineDetected and Quantified6.21 +/- 4.38 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified12.6 +/- 36.00 umol/mmol creatinineNewborn (0-30 days old)BothPhenylketonuria details
Associated Disorders and Diseases
Disease References
Supradiaphragmatic malignancy
  1. Goudas LC, Langlade A, Serrie A, Matson W, Milbury P, Thurel C, Sandouk P, Carr DB: Acute decreases in cerebrospinal fluid glutathione levels after intracerebroventricular morphine for cancer pain. Anesth Analg. 1999 Nov;89(5):1209-15. [PubMed:10553836 ]
Phenylketonuria
  1. Monch E, Kneer J, Jakobs C, Arnold M, Diehl H, Batzler U: Examination of urine metabolites in the newborn period and during protein loading tests at 6 months of age--Part 1. Eur J Pediatr. 1990;149 Suppl 1:S17-24. [PubMed:2091926 ]
  2. Rampini S, Vollmin JA, Bosshard HR, Muller M, Curtius HC: Aromatic acids in urine of healthy infants, persistent hyperphenylalaninemia, and phenylketonuria, before and after phenylalanine load. Pediatr Res. 1974 Jul;8(7):704-9. [PubMed:4837567 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound ID577
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB019021
KNApSAcK IDNot Available
Chemspider ID9010
KEGG Compound IDC03672
BioCyc ID4-HYDROXYPHENYLLACTATE
BiGG ID2392410
Wikipedia LinkNot Available
METLIN ID5723
PubChem Compound9378
PDB IDNot Available
ChEBI ID17385
References
Synthesis ReferenceDeng, 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.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  2. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
  3. Raw I, Schmidt BJ, Merzel J: Catecholamines and congenital pain insensitivity. Braz J Med Biol Res. 1984;17(3-4):271-9. [PubMed:6085021 ]
  4. Bennett MJ, Ragni MC, Hood I, Hale DE: Comparison of post-mortem urinary and vitreous humour organic acids. Ann Clin Biochem. 1992 Sep;29 ( Pt 5):541-5. [PubMed:1444166 ]
  5. Roth K, Cohn R, Yandrasitz J, Preti G, Dodd P, Segal S: Beta-methylcrotonic aciduria associated with lactic acidosis. J Pediatr. 1976 Feb;88(2):229-35. [PubMed:1249684 ]
  6. Spaapen LJ, Ketting D, Wadman SK, Bruinvis L, Duran M: Urinary D-4-hydroxyphenyllactate, D-phenyllactate and D-2-hydroxyisocaproate, abnormalities of bacterial origin. J Inherit Metab Dis. 1987;10(4):383-90. [PubMed:3126358 ]
  7. Deutsch JC: Determination of p-hydroxyphenylpyruvate, p-hydroxyphenyllactate and tyrosine in normal human plasma by gas chromatography-mass spectrometry isotope-dilution assay. J Chromatogr B Biomed Sci Appl. 1997 Mar 7;690(1-2):1-6. [PubMed:9106023 ]
  8. Mrochek JE, Dinsmore SR, Ohrt DW: Monitoring phenylalanine-tyrosine metabolism by high-resolution liquid chromatography of urine. Clin Chem. 1973 Aug;19(8):927-36. [PubMed:4720815 ]
  9. Higa S, Kishimoto S: Isolation of 2-hydroxycarboxylic acids with a boronate affinity gel. Anal Biochem. 1986 Apr;154(1):71-4. [PubMed:3706738 ]
  10. Jakobs C, Sweetman L, Nyhan WL: Chemical analysis of succinylacetone and 4-hydroxyphenyllactate in amniotic fluid using selective ion monitoring. Prenat Diagn. 1984 May-Jun;4(3):187-94. [PubMed:6463026 ]
  11. Beloborodova N, Bairamov I, Olenin A, Shubina V, Teplova V, Fedotcheva N: Effect of phenolic acids of microbial origin on production of reactive oxygen species in mitochondria and neutrophils. J Biomed Sci. 2012 Oct 12;19:89. doi: 10.1186/1423-0127-19-89. [PubMed:23061754 ]
  12. (). Charles Scriver, Arthur Beaudet, William Sly, David Valle, Barton Childs, Kenneth Kinzler, Bert Vogelstein. The Metabolic and Molecular Bases of Inherited Disease. McGraw-Hill Professional; 8 edition (Dec 15 2000). . . [ISBN:978-0079130358 ]

Enzymes

General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
Hydroxyphenyllactic acid → 3-(4-hydroxyphenyl)-2-(sulfooxy)propanoic aciddetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Hydroxyphenyllactic acid → 6-[4-(2-carboxy-2-hydroxyethyl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Hydroxyphenyllactic acid → 3,4,5-trihydroxy-6-{[2-hydroxy-3-(4-hydroxyphenyl)propanoyl]oxy}oxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
Hydroxyphenyllactic acid → 2-hydroxy-3-[4-(sulfooxy)phenyl]propanoic aciddetails