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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-11 18:57:56 UTC
Update Date2020-06-19 18:22:29 UTC
HMDB IDHMDB0034172
Secondary Accession Numbers
  • HMDB34172
Metabolite Identification
Common NameMethyl 2-hydroxybenzoate
DescriptionMethyl 2-hydroxybenzoate, also known as 2-(methoxycarbonyl)phenol or 2-carbomethoxyphenol, belongs to the class of organic compounds known as o-hydroxybenzoic acid esters. These are benzoic acid esters where the benzene ring is ortho-substituted with a hydroxy group. Methyl 2-hydroxybenzoate is an extremely weak basic (essentially neutral) compound (based on its pKa). Methyl 2-hydroxybenzoate is a mint, peppermint, and wintergreen tasting compound. Outside of the human body, Methyl 2-hydroxybenzoate is found, on average, in the highest concentration within hyssops and bilberries. Methyl 2-hydroxybenzoate has also been detected, but not quantified in, several different foods, such as chinese cinnamons, tamarinds, tea, mushrooms, and roselles. This could make methyl 2-hydroxybenzoate a potential biomarker for the consumption of these foods. Minor metabolism may occur in various tissues but hepatic metabolism constitutes the majority of metabolic processes of absorbed methyl salicylate. Methyl 2-hydroxybenzoate is a potentially toxic compound. Present in white wine, tea, porcini mushroom Boletus edulis, Bourbon vanilla, clary sage, red sage and fruits including cherry, apple, raspberry, papaya and plum. For acute joint and muscular pain, Methyl 2-hydroxybenzoate is used as a rubefacient and analgesic in deep heating liniments. This is thought to mask the underlying musculoskeletal pain and discomfort. Severe toxicity can result in acute lung injury, lethargy, coma, seizures, cerebral edema, and death. Counter-irritation is believed to cause a soothing sensation of warmth.
Structure
Data?1592590949
Synonyms
ValueSource
2-(Methoxycarbonyl)phenolChEBI
2-CarbomethoxyphenolChEBI
2-Hydroxybenzoic acid methyl esterChEBI
Betula oilChEBI
Gaultheria oilChEBI
Methyl O-hydroxybenzoateChEBI
Natural wintergreen oilChEBI
Oil OF wintergreenChEBI
Spicewood oilChEBI
Sweet birch oilChEBI
Teaberry oilChEBI
2-Hydroxybenzoate methyl esterGenerator
Methyl O-hydroxybenzoic acidGenerator
Methyl 2-hydroxybenzoic acidGenerator
Benzoic acid, 2-hydroxy-, methyl esterHMDB
FEMA 2745HMDB
Methyl ester 2-hydroxy-benzoic acidHMDB
Methyl salicylate, 8ciHMDB
O-Hydroxybenzoic acid, methyl esterHMDB
MethylsalicylateHMDB
RheumabalHMDB
HewedolorHMDB
LinsalHMDB
Metsal linimentHMDB
Methyl salicylate sodium saltHMDB
Methyl salicylic acidHMDB
Methyl ester 2-hydroxy benzoic acidHMDB
Methyl ester OF 2-hydroxy benzoic acidHMDB
Methyl salicylateHMDB
O-Hydroxybenzoic acid methyl esterHMDB
Methyl 2-hydroxybenzoateChEBI
Chemical FormulaC8H8O3
Average Molecular Weight152.1473
Monoisotopic Molecular Weight152.047344122
IUPAC Namemethyl 2-hydroxybenzoate
Traditional Namemethyl salicylate
CAS Registry Number119-36-8
SMILES
COC(=O)C1=C(O)C=CC=C1
InChI Identifier
InChI=1S/C8H8O3/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5,9H,1H3
InChI KeyOSWPMRLSEDHDFF-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as o-hydroxybenzoic acid esters. These are benzoic acid esters where the benzene ring is ortho-substituted with a hydroxy group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct Parento-Hydroxybenzoic acid esters
Alternative Parents
Substituents
  • O-hydroxybenzoic acid ester
  • Salicylic acid or derivatives
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Vinylogous acid
  • Methyl ester
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-8.6 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.7 mg/mL at 30 °CNot Available
LogP2.55Not Available
Predicted Properties
PropertyValueSource
Water Solubility5.73 g/LALOGPS
logP2.07ALOGPS
logP2.32ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)9.72ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.06 m³·mol⁻¹ChemAxon
Polarizability14.98 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00dl-9800000000-4c121b87ee97a30f4150Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00dl-9800000000-aeff759175e190d33827Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00dl-9700000000-8449a003796d4c61d429Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00dl-9800000000-4c121b87ee97a30f4150Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00dl-9800000000-aeff759175e190d33827Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00dl-9700000000-8449a003796d4c61d429Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-5900000000-bb69ba7d9fb7889830b6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fk9-6920000000-3af2acf054d451df9493Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0fk9-3900000000-e2029bf3c75775175ff3Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0udi-0900000000-68100343194ca59dc3dcSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0udi-0900000000-685742c82233f695b1f9Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0uk9-0900000000-6b4261227c07f3f37829Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0fk9-0900000000-d947b63ba1f404e65847Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-00di-0900000000-cef75bde9d9688c24943Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-00di-0900000000-619ac91f6d02cca22e34Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-00di-0900000000-972c6897098e7099014bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-00di-0900000000-7adc31a6192a35776d77Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-00di-0900000000-4409a163b77175958dadSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-00di-1900000000-e227574efc1f513f782eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-00di-3900000000-698a94aee209f31a1b16Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 10V, positivesplash10-01b9-9600000000-940f844a43e36507f542Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 11V, positivesplash10-014i-9200000000-a2caed2cb41617423174Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-014i-9000000000-be109281c3eb1b276861Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-00di-0900000000-9e24206fc4e0bc22769aSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-0006-9000000000-e886631a9ef343795dc0Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-014i-9000000000-ddc0fb8a40062ab7c744Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-00di-0900000000-85d6f511342ec3ef1f61Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-eba52e49290e16ea60c0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-0900000000-684f1c8a3cf324183257Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uk9-9300000000-a594ffaab84fc15a2edcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-76d5fc81bafad7c2222cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-dae7a80af6333acd66fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gb9-9600000000-09304803bc773495c704Spectrum
MSMass Spectrum (Electron Ionization)splash10-00dl-9800000000-1d56d6cf07db519b50e2Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected and Quantified28.481 nmol/g wet fecesAdult (>18 years old)Not Specified
Normal
details
FecesDetected and Quantified120.497 nmol/g wet fecesAdult (>18 years old)Not Specified
Normal
details
FecesDetected and Quantified142.406 nmol/g wet fecesAdult (>18 years old)Not Specified
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB09543
Phenol Explorer Compound IDNot Available
FooDB IDFDB012459
KNApSAcK IDC00030767
Chemspider ID13848808
KEGG Compound IDC12305
BioCyc IDCPD-6442
BiGG IDNot Available
Wikipedia LinkMethyl_salicylate
METLIN IDNot Available
PubChem Compound4133
PDB IDNot Available
ChEBI ID31832
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .