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Identification
YMDB IDYMDB01370
NameMethyl 2-hydroxy benzoate
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionMethyl salicylate, also known as Methyl salicylate or methyl salicylate, 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 salicylate exists as a liquid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Methyl salicylate exists in all eukaryotes, ranging from yeast to humans. Methyl salicylate is a potentially toxic compound.
Structure
Thumb
Synonyms
  • 2-(Methoxycarbonyl)phenol
  • 2-Hydroxybenzoic acid, methyl ester
  • Analgit
  • benzoate anion
  • Benzoic acid, 2-hydroxy-, methyl ester
  • benzoic acid, ion(1-)
  • Betula
  • Betula Lenta
  • Betula oil
  • Exagien
  • Flucarmit
  • Gaultheria oil
  • Gaultheria Oil, artificial
  • Gaultheriaoel
  • Gaultheric acid
  • Methyl 2-hydroxybenzoate
  • Methyl ester 2-hydroxy-benzoic acid
  • Methyl o-hydroxybenzoate
  • Methyl salicylate
  • Natural wintergreen oil
  • o-Hydroxybenzoic acid, methyl ester
  • Oil of Wintergreen
  • Salicylic acid, methyl ester
  • Spicewood Oil
  • Sweet birch oil
  • Synthetic wintergreen oil
  • Teaberry oil
  • Wintergreen oil
  • Wintergreen Oil, synthetic
  • Wintergruenoel
  • 2-Carbomethoxyphenol
  • 2-Hydroxybenzoic acid methyl ester
  • 2-Hydroxybenzoate methyl ester
  • Methyl 2-hydroxybenzoic acid
  • Methyl O-hydroxybenzoic acid
  • Methyl salicylic acid
  • FEMA 2745
  • Methyl salicylate, 8ci
  • Methylsalicylate
  • Rheumabal
  • Hewedolor
  • Linsal
  • Metsal liniment
  • Methyl salicylate sodium salt
CAS number119-36-8
WeightAverage: 152.1473
Monoisotopic: 152.047344122
InChI KeyOSWPMRLSEDHDFF-UHFFFAOYSA-N
InChIInChI=1S/C8H8O3/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5,9H,1H3
IUPAC Namemethyl 2-hydroxybenzoate
Traditional IUPAC Namemethyl salicylate
Chemical FormulaC8H8O3
SMILESCOC(=O)C1=C(O)C=CC=C1
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
Physical Properties
StateLiquid
Charge0
Melting point-8 °C
Experimental Properties
PropertyValueReference
Water Solubility0.7 mg/mL at 30 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP2.55 [SANGSTER (1994)]PhysProp
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • Tsakiris, A., Koutinas, A. A., Psarianos, C., Kourkoutas, Y., Bekatorou, A. (2010). "A new process for wine production by penetration of yeast in uncrushed frozen grapes." Appl Biochem Biotechnol 162:1109-1121.20151225
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID16150
HMDB IDHMDB0034172
Pubchem Compound ID4133
Kegg IDC12305
ChemSpider ID13848808
FOODB IDFDB012459
Wikipedia IDMethyl_salicylate
BioCyc IDNot Available