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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-24 12:35:05 UTC
Update Date2021-09-07 17:05:24 UTC
HMDB IDHMDB0004815
Secondary Accession Numbers
  • HMDB04815
Metabolite Identification
Common Name4-Hydroxy-3-methylbenzoic acid
Description4-Hydroxy-3-methylbenzoic acid, also known as 4,3-cresotic acid or 4-hydroxy-m-toluic acid, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 4-Hydroxy-3-methylbenzoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1582752314
Synonyms
ValueSource
4,3-Cresotic acidChEBI
4-Hydroxy-m-toluic acidChEBI
4,3-CresotateGenerator
4-Hydroxy-m-toluateGenerator
4-Hydroxy-3-methylbenzoateGenerator
3-Methyl-4-hydroxybenzoateHMDB
3-Methyl-4-hydroxybenzoic acidHMDB
4-Hydroxy-3-methyl-benzoateHMDB
4-Hydroxy-3-methyl-benzoic acidHMDB
4-Hydroxy-3-methoxybenzoic acidHMDB
Vanillic acidHMDB
4-Hydroxy-3-methylbenzoic acidHMDB
Chemical FormulaC8H8O3
Average Molecular Weight152.1473
Monoisotopic Molecular Weight152.047344122
IUPAC Name4-hydroxy-3-methylbenzoic acid
Traditional Name4-hydroxy-3-methylbenzoic acid
CAS Registry Number499-76-3
SMILES
CC1=CC(=CC=C1O)C(O)=O
InChI Identifier
InChI=1S/C8H8O3/c1-5-4-6(8(10)11)2-3-7(5)9/h2-4,9H,1H3,(H,10,11)
InChI KeyLTFHNKUKQYVHDX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentHydroxybenzoic acid derivatives
Alternative Parents
Substituents
  • Hydroxybenzoic acid
  • Benzoic acid
  • O-cresol
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • Toluene
  • Phenol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility11.6 mg/mL at 100 °CNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility4.52 g/LALOGPS
logP1.86ALOGPS
logP1.84ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)4.38ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40.34 m³·mol⁻¹ChemAxon
Polarizability15.01 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available134.131661259
DarkChem[M-H]-PredictedNot Available128.8231661259

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
4-Hydroxy-3-methylbenzoic acid,1TMS,#11685.426https://arxiv.org/abs/1905.12712
4-Hydroxy-3-methylbenzoic acid,1TMS,#21675.4199https://arxiv.org/abs/1905.12712
4-Hydroxy-3-methylbenzoic acid,2TMS,#11717.525https://arxiv.org/abs/1905.12712
4-Hydroxy-3-methylbenzoic acid,1TBDMS,#11941.4039https://arxiv.org/abs/1905.12712
4-Hydroxy-3-methylbenzoic acid,1TBDMS,#21916.623https://arxiv.org/abs/1905.12712
4-Hydroxy-3-methylbenzoic acid,2TBDMS,#12229.6636https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zfr-2900000000-8c797b085363527030ee2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-05gi-8290000000-f504bba638b849bb3e3a2017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0pb9-0900000000-7116c4f6bc6a16489f932012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-002f-9100000000-5cb5ac07c526f364ec472012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00or-9000000000-48da170e5bf8545c76ad2012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00r2-9400000000-74e1e2ded12f501df2e52021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-005c-9700000000-ec74ea932b54181ecf7f2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4r-2900000000-3a1e1188e20892c5b6ea2021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0900000000-b71e7e5af0f2a18fde932017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-0900000000-a09894245cfcd228962f2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-9400000000-a4f7437005df1701ba6f2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-09bb3008e287bfe7e21d2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-0900000000-ab8a808b767d57f51fc42017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9800000000-685fd00ed340ca85a59e2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-2900000000-b91d4b89123d2144bea52021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-4900000000-f7ca6adae4dd477716c02021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9000000000-805028da81d33adb93312021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-4d5dcc5d2bfbb145667f2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-1a6a31d05eb4cafd05c62021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9500000000-7b09fe32d2bcc847325d2021-09-08View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-05View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, predicted)2012-12-05View Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
UrineDetected and Quantified13.1 (3.6-54.0) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified7.5 (6.7-17.1) umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified6.0 (0.9-28.6) umol/mmol creatinineChildren (1-13 years old)Both
Normal
details
UrineDetected and Quantified4.3 (2.7-8.9) umol/mmol creatinineChildren (1-13 years old)Both
Normal
details
UrineDetected and Quantified3.0 (1.3-9.7) umol/mmol creatinineAdolescent (13-18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023425
KNApSAcK IDNot Available
Chemspider ID61446
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound68138
PDB IDNot Available
ChEBI ID85239
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceKing, L. Carroll; McWhirter, Margaret; Barton, Daniel M. Reactions of acetophenols with iodine and pyridine and the preparation of hydroxybenzoic acids. Journal of the American Chemical Society (1945), 67 2089-92.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]