Record Information
Version1.0
Creation date2010-04-08 22:10:11 UTC
Update date2020-09-17 15:30:14 UTC
Primary IDFDB012459
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMethyl salicylate
DescriptionMethyl salicylate or methyl 2-hydroxybenzoate, 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, a methyl ester of salicylic acid, is a neutral compound. It is a colorless, viscous liquid with a sweet fruity odor reminiscent of a mint and with a peppermint, and wintergreen taste. It is a naturally occurring organic compound in many species of plants, particularly wintergreens. Methyl 2-hydroxybenzoate is found in highest concentrations in hyssops and bilberries and was detected in 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. It is also present in wines (PMID: 31500198; PMID: 31500198), tea, porcini mushroom Boletus edulis, Bourbon vanilla, clary sage, red sage and fruits including cherry, apple, raspberry ( PMID: 31608465), papaya and plum. It is an anti-herbivore used by some plants to recruit beneficial insects (PMID: 15537163). It is used as a fragrance and is used in foods such as chewing gum and mints and in beverages. It is a topical analgesic added to liniments (such as Bengay) where it acts as a counter-irritant to relieve joint and muscle pain. As methyl salicyclate is metabolized to salicyclate, it is a potentially toxic compound, particularly to children or to adults who excessive overuse such liniments.
CAS Number119-36-8
Structure
Thumb
Synonyms
SynonymSource
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
Methyl o-hydroxybenzoatebiospider
Methyl salicylate, 8CIdb_source
o-Hydroxybenzoic acid, methyl esterbiospider
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
Chemical FormulaC8H8O3
IUPAC namemethyl 2-hydroxybenzoate
InChI IdentifierInChI=1S/C8H8O3/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5,9H,1H3
InChI KeyOSWPMRLSEDHDFF-UHFFFAOYSA-N
Isomeric SMILESCOC(=O)C1=CC=CC=C1O
Average Molecular Weight152.1473
Monoisotopic Molecular Weight152.047344122
Classification
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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 63.15%; H 5.30%; O 31.55%DFC
Melting PointMp -8.6°DFC
Boiling PointBp12 101°DFC
Experimental Water Solubility0.7 mg/mL at 30 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP2.55SANGSTER (1994)
Experimental pKapKa 9.87 (20°, 0.1M NaClO4)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd18.54 1.85DFC
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-00dl-9800000000-1d56d6cf07db519b50e2Spectrum
GC-MSMethyl salicylate, non-derivatized, GC-MS Spectrumsplash10-00dl-9800000000-4c121b87ee97a30f4150Spectrum
GC-MSMethyl salicylate, non-derivatized, GC-MS Spectrumsplash10-00dl-9800000000-aeff759175e190d33827Spectrum
GC-MSMethyl salicylate, non-derivatized, GC-MS Spectrumsplash10-00dl-9700000000-8449a003796d4c61d429Spectrum
GC-MSMethyl salicylate, non-derivatized, GC-MS Spectrumsplash10-00dl-9800000000-4c121b87ee97a30f4150Spectrum
GC-MSMethyl salicylate, non-derivatized, GC-MS Spectrumsplash10-00dl-9800000000-aeff759175e190d33827Spectrum
GC-MSMethyl salicylate, non-derivatized, GC-MS Spectrumsplash10-00dl-9700000000-8449a003796d4c61d429Spectrum
Predicted GC-MSMethyl salicylate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-5900000000-bb69ba7d9fb7889830b6Spectrum
Predicted GC-MSMethyl salicylate, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fk9-6920000000-3af2acf054d451df9493Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0fk9-3900000000-e2029bf3c75775175ff3Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0udi-0900000000-68100343194ca59dc3dcSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0udi-0900000000-685742c82233f695b1f9Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0uk9-0900000000-6b4261227c07f3f37829Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0fk9-0900000000-d947b63ba1f404e65847Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-00di-0900000000-cef75bde9d9688c24943Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-00di-0900000000-619ac91f6d02cca22e34Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-00di-0900000000-972c6897098e7099014bSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-00di-0900000000-7adc31a6192a35776d77Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-00di-0900000000-4409a163b77175958dadSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-00di-1900000000-e227574efc1f513f782eSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-00di-3900000000-698a94aee209f31a1b16Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 10V, positivesplash10-01b9-9600000000-940f844a43e36507f542Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 11V, positivesplash10-014i-9200000000-a2caed2cb41617423174Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-014i-9000000000-be109281c3eb1b276861Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-00di-0900000000-9e24206fc4e0bc22769aSpectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-0006-9000000000-e886631a9ef343795dc0Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-014i-9000000000-ddc0fb8a40062ab7c744Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-00di-0900000000-85d6f511342ec3ef1f61Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-eba52e49290e16ea60c0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-0900000000-684f1c8a3cf324183257Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uk9-9300000000-a594ffaab84fc15a2edcSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-76d5fc81bafad7c2222cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-dae7a80af6333acd66fcSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gb9-9600000000-09304803bc773495c704Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
ChemSpider ID13848808
ChEMBL IDCHEMBL108545
KEGG Compound IDC12305
Pubchem Compound ID4133
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34172
CRC / DFC (Dictionary of Food Compounds) IDHHB30-H:HHB30-H
EAFUS ID2495
Dr. Duke IDMETHYL-SALICYLATE|SALICYLIC-ACID-METHYL-ESTER
BIGG IDNot Available
KNApSAcK IDC00030767
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID119-36-8
GoodScent IDrw1008471
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
analgesic35480 An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.DUKE
anaphrodisiacDUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti pyretic35493 A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.DUKE
anti radicularDUKE
anti rheumatalgic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti tartarDUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
carminativeDUKE
counterirritantDUKE
dentifriceDUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
herpetifuge25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
insectifuge24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
Insectiphile24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
peppermint
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
wintergreen
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
mint
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.