Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
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 has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 4-hydroxy-3-methylbenzoic acid a potential biomarker for the consumption of these foods. 4-Hydroxy-3-methylbenzoic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on 4-Hydroxy-3-methylbenzoic acid.
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

Route of exposure

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
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility4.52 g/LALOGPS
logP10(1.86) g/LALOGPS
logP10(1.84) g/LChemAxon
logS10(-1.5) g/LALOGPS
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 Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+134.131661259
DarkChem[M-H]-128.8231661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Hydroxy-3-methylbenzoic acidCC1=CC(=CC=C1O)C(O)=O2775.7Standard polar33892256
4-Hydroxy-3-methylbenzoic acidCC1=CC(=CC=C1O)C(O)=O1413.5Standard non polar33892256
4-Hydroxy-3-methylbenzoic acidCC1=CC(=CC=C1O)C(O)=O1565.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Hydroxy-3-methylbenzoic acid,1TMS,isomer #1CC1=CC(C(=O)O)=CC=C1O[Si](C)(C)C1685.4Semi standard non polar33892256
4-Hydroxy-3-methylbenzoic acid,1TMS,isomer #2CC1=CC(C(=O)O[Si](C)(C)C)=CC=C1O1675.4Semi standard non polar33892256
4-Hydroxy-3-methylbenzoic acid,2TMS,isomer #1CC1=CC(C(=O)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C1717.5Semi standard non polar33892256
4-Hydroxy-3-methylbenzoic acid,1TBDMS,isomer #1CC1=CC(C(=O)O)=CC=C1O[Si](C)(C)C(C)(C)C1941.4Semi standard non polar33892256
4-Hydroxy-3-methylbenzoic acid,1TBDMS,isomer #2CC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O1916.6Semi standard non polar33892256
4-Hydroxy-3-methylbenzoic acid,2TBDMS,isomer #1CC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2229.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxy-3-methylbenzoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zfr-2900000000-8c797b085363527030ee2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxy-3-methylbenzoic acid GC-MS (2 TMS) - 70eV, Positivesplash10-05gi-8290000000-f504bba638b849bb3e3a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxy-3-methylbenzoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxy-3-methylbenzoic acid 20V, Negative-QTOFsplash10-00r2-9400000000-74e1e2ded12f501df2e52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxy-3-methylbenzoic acid 40V, Negative-QTOFsplash10-005c-9700000000-ec74ea932b54181ecf7f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxy-3-methylbenzoic acid 10V, Negative-QTOFsplash10-0a4r-2900000000-3a1e1188e20892c5b6ea2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxy-3-methylbenzoic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0pb9-0900000000-7116c4f6bc6a16489f932012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxy-3-methylbenzoic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-002f-9100000000-5cb5ac07c526f364ec472012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxy-3-methylbenzoic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-00or-9000000000-48da170e5bf8545c76ad2012-07-25HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-methylbenzoic acid 10V, Negative-QTOFsplash10-0udi-0900000000-09bb3008e287bfe7e21d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-methylbenzoic acid 20V, Negative-QTOFsplash10-0pb9-0900000000-ab8a808b767d57f51fc42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-methylbenzoic acid 40V, Negative-QTOFsplash10-0a4i-9800000000-685fd00ed340ca85a59e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-methylbenzoic acid 10V, Negative-QTOFsplash10-0a4i-0900000000-4d5dcc5d2bfbb145667f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-methylbenzoic acid 20V, Negative-QTOFsplash10-0a4i-0900000000-1a6a31d05eb4cafd05c62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-methylbenzoic acid 40V, Negative-QTOFsplash10-0a4i-9500000000-7b09fe32d2bcc847325d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-methylbenzoic acid 10V, Positive-QTOFsplash10-0udr-0900000000-b71e7e5af0f2a18fde932017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-methylbenzoic acid 20V, Positive-QTOFsplash10-052r-0900000000-a09894245cfcd228962f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-methylbenzoic acid 40V, Positive-QTOFsplash10-056r-9400000000-a4f7437005df1701ba6f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-methylbenzoic acid 10V, Positive-QTOFsplash10-0a4r-2900000000-b91d4b89123d2144bea52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-methylbenzoic acid 20V, Positive-QTOFsplash10-0a4l-4900000000-f7ca6adae4dd477716c02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-methylbenzoic acid 40V, Positive-QTOFsplash10-004i-9000000000-805028da81d33adb93312021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView 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
Good Scents 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 ]