Showing Compound Card for Methyl salicylate (CDB000074)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (2) Show 5 proteinsXML
Record Information
Version1.0
Created at2020-03-18 23:23:48 UTC
Updated at2020-12-07 19:07:03 UTC
CannabisDB IDCDB000074
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common 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 and in cannabis plants (PMID: 6991645 ). 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 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.
Structure
Thumb
MOLSDFPDBSMILESInChI
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 Weight152.15
Monoisotopic Molecular Weight152.0473
IUPAC Namemethyl 2-hydroxybenzoate
Traditional Namemethyl salicylate
CAS Registry Number119-36-8
SMILES
COC(=O)C1=CC=CC=C1O
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
StateSolid
Experimental Properties
PropertyValueReference
Melting Point-8.6 °CNot Available
Boiling Point222 °CWikipedia
Water Solubility0.7 mg/mL at 30 °CNot Available
logP2.55Not Available
Predicted Properties
PropertyValueSource
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-00dl-9800000000-1d56d6cf07db519b50e22014-09-20View Spectrum
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
Predicted GC-MSMethyl salicylate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0fk9-3900000000-e2029bf3c75775175ff32017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0udi-0900000000-68100343194ca59dc3dc2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0udi-0900000000-685742c82233f695b1f92020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0uk9-0900000000-6b4261227c07f3f378292020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0fk9-0900000000-d947b63ba1f404e658472020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-00di-0900000000-cef75bde9d9688c249432020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-00di-0900000000-619ac91f6d02cca22e342020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-00di-0900000000-972c6897098e7099014b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-00di-0900000000-7adc31a6192a35776d772020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-00di-0900000000-4409a163b77175958dad2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-00di-1900000000-e227574efc1f513f782e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-00di-3900000000-698a94aee209f31a1b162020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 10V, positivesplash10-01b9-9600000000-940f844a43e36507f5422020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 11V, positivesplash10-014i-9200000000-a2caed2cb416174231742020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-014i-9000000000-be109281c3eb1b2768612020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-00di-0900000000-9e24206fc4e0bc22769a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-0006-9000000000-e886631a9ef343795dc02020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-014i-9000000000-ddc0fb8a40062ab7c7442020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-00di-0900000000-85d6f511342ec3ef1f612020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-eba52e49290e16ea60c02015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-0900000000-684f1c8a3cf3241832572015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uk9-9300000000-a594ffaab84fc15a2edc2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-76d5fc81bafad7c2222c2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-dae7a80af6333acd66fc2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gb9-9600000000-09304803bc773495c7042015-04-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Prostaglandin G/H synthase 2PTGS21q25.2-q25.3P35354 details
Prostaglandin G/H synthase 1PTGS19q32-q33.3P23219 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Prostaglandin G/H synthase 2PTGS21q25.2-q25.3P35354 details
Prostaglandin G/H synthase 1PTGS19q32-q33.3P23219 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Prostaglandin G/H synthase 1PTGS19q32-q33.3P23219 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0034172
DrugBank IDDB09543
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. Carlin S, Masuero D, Guella G, Vrhovsek U, Mattivi F: Methyl Salicylate Glycosides in Some Italian Varietal Wines. Molecules. 2019 Sep 6;24(18). pii: molecules24183260. doi: 10.3390/molecules24183260. [PubMed:31500198 ]
  3. Yu AN, Yang YN, Yang Y, Zheng FP, Sun BG: Free and bound volatile compounds in the Rubus coreanus fruits of different ripening stages. J Food Biochem. 2019 Oct;43(10):e12964. doi: 10.1111/jfbc.12964. Epub 2019 Jun 26. [PubMed:31608465 ]
  4. James DG, Price TS: Field-testing of methyl salicylate for recruitment and retention of beneficial insects in grapes and hops. J Chem Ecol. 2004 Aug;30(8):1613-28. doi: 10.1023/b:joec.0000042072.18151.6f. [PubMed:15537163 ]

Enzymes

Enzyme Details
1. Prostaglandin G/H synthase 2
General function:
Involved in peroxidase activity
Specific function:
Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular weight:
68995.625
Enzyme Details
2. Prostaglandin G/H synthase 1
General function:
Involved in peroxidase activity
Specific function:
May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular weight:
68685.82