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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-05-16 17:34:31 UTC
HMDB IDHMDB00755
Secondary Accession NumbersNone
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-(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
HydroxyphenyllactateHMDB
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 KeyInChIKey=JVGVDSSUAVXRDY-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpropanoic acids. These 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
  • Phenol
  • Benzenoid
  • Hydroxy acid
  • Monocyclic benzene moiety
  • Alpha-hydroxy acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Microbial
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Mitochondria
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.44 m3·mol-1ChemAxon
Polarizability17.51 Å3ChemAxon
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
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
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Mitochondria
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • Epidermis
  • Prostate
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.64 +/- 0.24 uMAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified25.10 +/- 14.93 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
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 QuantifiedNot ApplicableAdult (>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 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
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. [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. [2091926 ]
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
NuGOwiki LinkHMDB00755
Metagene LinkHMDB00755
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. [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. [8087979 ]
  3. Raw I, Schmidt BJ, Merzel J: Catecholamines and congenital pain insensitivity. Braz J Med Biol Res. 1984;17(3-4):271-9. [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. [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. [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. [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. [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. [4720815 ]
  9. Higa S, Kishimoto S: Isolation of 2-hydroxycarboxylic acids with a boronate affinity gel. Anal Biochem. 1986 Apr;154(1):71-4. [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. [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. [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]