1-O-methylsalicylate (PAMDB120338)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB120338
Identification
Name: 1-O-methylsalicylate
Description:A benzoate ester that is the methyl ester of salicylic acid.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 2-(Methoxycarbonyl)phenol
  • 2-Carbomethoxyphenol
  • 2-Hydroxybenzoic acid methyl ester
  • Betula oil
  • Gaultheria oil
  • Methyl 2-hydroxybenzoate
  • Methyl o-hydroxybenzoate
  • methyl salicylate
  • Natural wintergreen oil
  • Oil of wintergreen
  • Spicewood Oil
  • Sweet birch oil
  • Teaberry oil
Chemical Formula: C8H8O3
Average Molecular Weight: 152.149
Monoisotopic Molecular Weight: 152.04735
InChI Key: OSWPMRLSEDHDFF-UHFFFAOYSA-N
InChI:InChI=1S/C8H8O3/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5,9H,1H3
CAS number: 119-36-8
IUPAC Name:methyl 2-hydroxybenzoate
Traditional IUPAC Name: methyl salicylate
SMILES:COC(C1(C=CC=CC=1O))=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as o-hydroxybenzoic acid esters. These are benzoic acid esters where the benzene ring is ortho-substituted with a hydroxy group.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Benzenoids
Sub ClassBenzene and substituted derivatives
Direct Parent o-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 Framework Aromatic homomonocyclic compounds
External Descriptors
Physical Properties
State: Liquid
Charge:0
Melting point: -8.6 °C
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.06 m3·mol-1ChemAxon
Polarizability14.98 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
1-O-methylsalicylate + Water → Hydrogen ion + salicylate + Methanol
Pathways:
    Spectra
    Spectra:
    Spectrum TypeDescriptionSplash Key
    Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-eba52e49290e16ea60c0View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-0900000000-684f1c8a3cf324183257View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uk9-9300000000-a594ffaab84fc15a2edcView in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-76d5fc81bafad7c2222cView in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-dae7a80af6333acd66fcView in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gb9-9600000000-09304803bc773495c704View in MoNA
    MSMass Spectrum (Electron Ionization)splash10-00dl-9800000000-1d56d6cf07db519b50e2View in MoNA
    1D NMR1H NMR SpectrumNot Available
    1D NMR13C NMR SpectrumNot Available
    References
    References:
    • Kappers IF, Hoogerbrugge H, Bouwmeester HJ, Dicke M (2011)Variation in herbivory-induced volatiles among cucumber (Cucumis sativus L.) varieties has consequences for the attraction of carnivorous natural enemies. Journal of chemical ecology 37, Pubmed: 21249432
    • Ito K, Ito M (2011)Sedative effects of vapor inhalation of the essential oil of Microtoena patchoulii and its related compounds. Journal of natural medicines 65, Pubmed: 21287406
    • Mallinger RE, Hogg DB, Gratton C (2011)Methyl salicylate attracts natural enemies and reduces populations of soybean aphids (Hemiptera: Aphididae) in soybean agroecosystems. Journal of economic entomology 104, Pubmed: 21404848
    • Tamilvanan S, Karmegam S (2012)In vitro evaluation of chitosan coated- and uncoated-calcium alginate beads containing methyl salicylate-lactose physical mixture. Pharmaceutical development and technology 17, Pubmed: 21609308
    • Yun LJ, Chen WL (2011)SA and ROS are involved in methyl salicylate-induced programmed cell death in Arabidopsis thaliana. Plant cell reports 30, Pubmed: 21327960
    • Zhang X, Shen L, Li F, Meng D, Sheng J (2011)Methyl salicylate-induced arginine catabolism is associated with up-regulation of polyamine and nitric oxide levels and improves chilling tolerance in cherry tomato fruit. Journal of agricultural and food chemistry 59, Pubmed: 21790190
    • Dekker T, Ignell R, Ghebru M, Glinwood R, Hopkins R (2011)Identification of mosquito repellent odours from Ocimum forskolei. Parasites & vectors 4, Pubmed: 21936953
    Synthesis Reference: Not Available
    Material Safety Data Sheet (MSDS) Not Available
    External Links:
    ResourceLink
    METABOLIGHTSMTBLC31832
    HMDBHMDB34172
    CHEMSPIDER13848808
    CHEBI31832
    PUBCHEM4133
    LIGAND-CPDC12305