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
Version4.0
StatusDetected and Quantified
Creation Date2012-09-11 18:57:56 UTC
Update Date2019-08-27 16:01:16 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 a drug. 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 in hyssops and bilberries. methyl 2-hydroxybenzoate has also been detected, but not quantified in, several different foods, such as sour cherries, tamarinds, garden tomato (var.), black elderberries, and mandarin orange (clementine, tangerine). This could make methyl 2-hydroxybenzoate a potential biomarker for the consumption of these foods. Present in white wine, tea, porcini mushroom Boletus edulis, Bourbon vanilla, clary sage, red sage and fruits including cherry, apple, raspberry, papaya and plum. Methyl 2-hydroxybenzoate is a potentially toxic compound. No indication of carcinogenicity to humans (not listed by IARC). Found in leaves of Gaultheria procumbens (wintergreen).
Structure
Data?1566921676
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 2-hydroxybenzoateChEBI
Methyl salicylic acidGenerator
Methyl ester 2-hydroxy benzoic acidHMDB
Methyl ester of 2-hydroxy benzoic acidHMDB
Methyl salicylateHMDB
o-Hydroxybenzoic acid methyl esterHMDB
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
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 Quantified Adult (>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
FoodDB IDFDB012459
KNApSAcK IDC00030767
Chemspider ID13848808
KEGG Compound IDC12305
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethyl_salicylate
METLIN IDNot Available
PubChem Compound4133
PDB IDNot Available
ChEBI ID31832
Food Biomarker OntologyNot Available
VMH IDNot Available
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.. .