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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:32:49 UTC
Update Date2020-02-26 21:44:29 UTC
HMDB IDHMDB0029817
Secondary Accession Numbers
  • HMDB29817
Metabolite Identification
Common NameEthyl salicylate
DescriptionEthyl salicylate, also known as fema 2458 or mesotol, 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. Ethyl salicylate is an extremely weak basic (essentially neutral) compound (based on its pKa). Ethyl salicylate is a sweet, balsam, and floral tasting compound. Outside of the human body, Ethyl salicylate has been detected, but not quantified in, several different foods, such as evergreen blackberries, alcoholic beverages, black elderberries, garden tomato (var.), and fruits. This could make ethyl salicylate a potential biomarker for the consumption of these foods. Ethyl salicylate is the ester formed by the condensation of salicylic acid and ethanol. It is a clear liquid that is sparingly soluble in water, but soluble in alcohol and ether. It has a pleasant odor resembling wintergreen and is used in perfumery and artificial flavors.
Structure
Data?1582753469
Synonyms
ValueSource
Ethyl salicylic acidGenerator
2-Hydroxybenzoic acid ethyl esterHMDB
2-Hydroxyethylbenzoic acidHMDB
Benzoic acid, 2-hydroxy-, ethyl esterHMDB
Benzoic acid, hydroxy-, ethyl esterHMDB
Ethyl 2-hydroxybenzoateHMDB
Ethyl hydroxybenzoateHMDB
Ethyl O-hydroxybenzoateHMDB
Ethyl salicyclateHMDB
FEMA 2458HMDB
MesotolHMDB
Methyl 2-hydroxybenzoateHMDB
Methyl salicylateHMDB
O-(Ethoxycarbonyl)phenolHMDB
Sal etherHMDB
Sal ethylHMDB
Salicyclic acid, ethyl esterHMDB
Salicylic acid, ethyl esterHMDB
Salicylic etherHMDB
Salicylic ethyl esterHMDB
SalotanHMDB
SalstanHMDB
Ethyl 2-hydroxybenzoic acidHMDB
2-CarboethoxyphenolHMDB
2-EthoxycarbonylphenolHMDB
O-Hydroxybenzoic acid ethyl esterHMDB
Ethyl salicylateMeSH
Chemical FormulaC9H10O3
Average Molecular Weight166.1739
Monoisotopic Molecular Weight166.062994186
IUPAC Nameethyl 2-hydroxybenzoate
Traditional Nameethyl salicylate
CAS Registry Number118-61-6
SMILES
CCOC(=O)C1=C(O)C=CC=C1
InChI Identifier
InChI=1S/C9H10O3/c1-2-12-9(11)7-5-3-4-6-8(7)10/h3-6,10H,2H2,1H3
InChI KeyGYCKQBWUSACYIF-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
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point1.3 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.95Not Available
Predicted Properties
PropertyValueSource
Water Solubility3.07 g/LALOGPS
logP2.76ALOGPS
logP2.68ChemAxon
logS-1.7ALOGPS
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 Count3ChemAxon
Refractivity44.81 m³·mol⁻¹ChemAxon
Polarizability16.81 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-5900000000-f5eb6e8bd07e0d734060Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00xu-8900000000-86cbf27957a874eacf48Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-6900000000-8e32263351a87a3cac48Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-5900000000-f5eb6e8bd07e0d734060Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00xu-8900000000-86cbf27957a874eacf48Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-6900000000-8e32263351a87a3cac48Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-3900000000-76416e68288f87d1b2fbSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-3910000000-3ab2317224cf5004c30dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-c9c4fa6ec7edfa49b61dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00xr-1900000000-ab4e08dfd3db7c5f59f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uk9-9300000000-2532177974c69b27ce91Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2900000000-040861e4eb1b3cfbb0aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014l-5900000000-b6232bbfa2f557c2f19eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-9c55ed111643f19b1e96Spectrum
MSMass Spectrum (Electron Ionization)splash10-00di-6900000000-fbc256a2ef3e0b3ff3bbSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not Quantified Adult (>18 years old)Both
Clostridium difficile infection
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001028
KNApSAcK IDNot Available
Chemspider ID21105897
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEthyl salicylate
METLIN IDNot Available
PubChem Compound8365
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .