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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 18:57:56 UTC
Update Date2022-03-07 02:54:00 UTC
HMDB IDHMDB0034172
Secondary Accession Numbers
  • HMDB34172
Metabolite Identification
Common NameMethyl 2-hydroxybenzoate
DescriptionMethyl 2-hydroxybenzoate, also known as methyl salicylate, 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 mint, peppermint, and wintergreen tasting compound. 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. 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. Methyl salicylate plays a role as a signaling molecule in plants.
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
MethylsalicylateMeSH, HMDB
RheumabalMeSH, HMDB
HewedolorMeSH, HMDB
LinsalMeSH, HMDB
Metsal linimentMeSH, HMDB
Methyl salicylate sodium saltMeSH, HMDB
Methyl 2-hydroxybenzoateChEBI
Methyl salicylic acidGenerator, HMDB
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

Biological location

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-8.6 °CNot Available
Boiling Point222.00 to 224.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.7 mg/mL at 30 °CNot Available
LogP2.55Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+132.76131661259
DarkChem[M-H]-130.05531661259
DeepCCS[M+H]+133.04430932474
DeepCCS[M-H]-129.27330932474
DeepCCS[M-2H]-166.75930932474
DeepCCS[M+Na]+142.29730932474
AllCCS[M+H]+132.032859911
AllCCS[M+H-H2O]+127.532859911
AllCCS[M+NH4]+136.232859911
AllCCS[M+Na]+137.532859911
AllCCS[M-H]-128.832859911
AllCCS[M+Na-2H]-130.232859911
AllCCS[M+HCOO]-131.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Methyl 2-hydroxybenzoateCOC(=O)C1=C(O)C=CC=C11879.9Standard polar33892256
Methyl 2-hydroxybenzoateCOC(=O)C1=C(O)C=CC=C11208.5Standard non polar33892256
Methyl 2-hydroxybenzoateCOC(=O)C1=C(O)C=CC=C11219.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Methyl 2-hydroxybenzoate,1TMS,isomer #1COC(=O)C1=CC=CC=C1O[Si](C)(C)C1414.6Semi standard non polar33892256
Methyl 2-hydroxybenzoate,1TBDMS,isomer #1COC(=O)C1=CC=CC=C1O[Si](C)(C)C(C)(C)C1637.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Methyl 2-hydroxybenzoate EI-B (Non-derivatized)splash10-00dl-9800000000-4c121b87ee97a30f41502017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl 2-hydroxybenzoate EI-B (Non-derivatized)splash10-00dl-9800000000-aeff759175e190d338272017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl 2-hydroxybenzoate EI-B (Non-derivatized)splash10-00dl-9700000000-8449a003796d4c61d4292017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl 2-hydroxybenzoate EI-B (Non-derivatized)splash10-00dl-9800000000-4c121b87ee97a30f41502018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl 2-hydroxybenzoate EI-B (Non-derivatized)splash10-00dl-9800000000-aeff759175e190d338272018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl 2-hydroxybenzoate EI-B (Non-derivatized)splash10-00dl-9700000000-8449a003796d4c61d4292018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyl 2-hydroxybenzoate GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-5900000000-bb69ba7d9fb7889830b62016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyl 2-hydroxybenzoate GC-MS (1 TMS) - 70eV, Positivesplash10-0fk9-6920000000-3af2acf054d451df94932017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyl 2-hydroxybenzoate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-00dl-9800000000-1d56d6cf07db519b50e22014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl 2-hydroxybenzoate LC-ESI-QTOF , negative-QTOFsplash10-0fk9-3900000000-e2029bf3c75775175ff32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl 2-hydroxybenzoate Orbitrap 1V, positive-QTOFsplash10-0udi-0900000000-68100343194ca59dc3dc2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl 2-hydroxybenzoate Orbitrap 1V, positive-QTOFsplash10-0udi-0900000000-685742c82233f695b1f92020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl 2-hydroxybenzoate Orbitrap 2V, positive-QTOFsplash10-0uk9-0900000000-6b4261227c07f3f378292020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl 2-hydroxybenzoate Orbitrap 2V, positive-QTOFsplash10-0fk9-0900000000-d947b63ba1f404e658472020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl 2-hydroxybenzoate Orbitrap 3V, positive-QTOFsplash10-00di-0900000000-cef75bde9d9688c249432020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl 2-hydroxybenzoate Orbitrap 3V, positive-QTOFsplash10-00di-0900000000-619ac91f6d02cca22e342020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl 2-hydroxybenzoate Orbitrap 3V, positive-QTOFsplash10-00di-0900000000-972c6897098e7099014b2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl 2-hydroxybenzoate Orbitrap 4V, positive-QTOFsplash10-00di-0900000000-7adc31a6192a35776d772020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl 2-hydroxybenzoate Orbitrap 5V, positive-QTOFsplash10-00di-0900000000-4409a163b77175958dad2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl 2-hydroxybenzoate Orbitrap 6V, positive-QTOFsplash10-00di-1900000000-e227574efc1f513f782e2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl 2-hydroxybenzoate Orbitrap 8V, positive-QTOFsplash10-00di-3900000000-698a94aee209f31a1b162020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl 2-hydroxybenzoate Orbitrap 10V, positive-QTOFsplash10-01b9-9600000000-940f844a43e36507f5422020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl 2-hydroxybenzoate Orbitrap 11V, positive-QTOFsplash10-014i-9200000000-a2caed2cb416174231742020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl 2-hydroxybenzoate Orbitrap 14V, positive-QTOFsplash10-014i-9000000000-be109281c3eb1b2768612020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl 2-hydroxybenzoate n/a 10V, positive-QTOFsplash10-00di-0900000000-9e24206fc4e0bc22769a2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl 2-hydroxybenzoate n/a 10V, positive-QTOFsplash10-0006-9000000000-e886631a9ef343795dc02020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl 2-hydroxybenzoate n/a 10V, positive-QTOFsplash10-014i-9000000000-ddc0fb8a40062ab7c7442020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl 2-hydroxybenzoate Orbitrap 3V, positive-QTOFsplash10-00di-0900000000-85d6f511342ec3ef1f612020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl 2-hydroxybenzoate Orbitrap 4V, positive-QTOFsplash10-00di-1900000000-d44997a1158509bf4cd92020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl 2-hydroxybenzoate Orbitrap 5V, positive-QTOFsplash10-00xr-6900000000-ca8a4f0ad6490f22817e2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl 2-hydroxybenzoate Orbitrap 6V, positive-QTOFsplash10-01b9-9400000000-e7a0ac323998ed33d9962020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl 2-hydroxybenzoate Orbitrap 7V, positive-QTOFsplash10-014i-9100000000-e74c487f5aae5767a3b12020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl 2-hydroxybenzoate Orbitrap 9V, positive-QTOFsplash10-014i-9000000000-84ff1f3a4d2cbbbc0e372020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl 2-hydroxybenzoate Orbitrap 11V, positive-QTOFsplash10-014i-9000000000-3a2de451ec8f64a3a2952020-07-22HMDB team, MONAView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
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 IDNot Available
Good Scents IDrw1008471
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.. .