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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:17:43 UTC
Update Date2022-03-07 02:54:06 UTC
HMDB IDHMDB0034451
Secondary Accession Numbers
  • HMDB34451
Metabolite Identification
Common NameEthyl oleate
DescriptionEthyl oleate is found in sweet marjoram. Ethyl oleate is a flavouring ingredient.Ethyl oleate is the ester formed by the condensation of the fatty acid oleic acid and ethanol. It is a colorless to light yellow liquid. Ethyl oleate is produced by the body during ethanol intoxication
Structure
Data?1563862565
Synonyms
ValueSource
Ethyl oleic acidGenerator
(Z)-9-Octadecenoic acid ethyl esterHMDB
9-Octadecenoic acid (Z)-, ethyl esterHMDB
Elaidic acid ethyl esterHMDB
Ethyl (9Z)-9-octadecenoateHMDB
Ethyl cis-9-octadecenoateHMDB
Ethyl Z-9-octadecenoateHMDB
FEMA 2450HMDB
Oleic acid ethyl esterHMDB
Chemical FormulaC20H38O2
Average Molecular Weight310.5145
Monoisotopic Molecular Weight310.28718046
IUPAC Nameethyl (9E)-octadec-9-enoate
Traditional Nameethyl oleate
CAS Registry Number111-62-6
SMILES
CCCCCCCC\C=C\CCCCCCCC(=O)OCC
InChI Identifier
InChI=1S/C20H38O2/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22-4-2/h11-12H,3-10,13-19H2,1-2H3/b12-11+
InChI KeyLVGKNOAMLMIIKO-VAWYXSNFSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentFatty acid esters
Alternative Parents
Substituents
  • Fatty acid ester
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-32 °CNot Available
Boiling Point205.00 to 208.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.00058 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP8.692 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.2e-05 g/LALOGPS
logP8.16ALOGPS
logP7.29ChemAxon
logS-7.2ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity96.92 m³·mol⁻¹ChemAxon
Polarizability41.8 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+183.79531661259
DarkChem[M-H]-185.19831661259
DeepCCS[M+H]+186.92630932474
DeepCCS[M-H]-183.9830932474
DeepCCS[M-2H]-219.09230932474
DeepCCS[M+Na]+195.38230932474
AllCCS[M+H]+189.232859911
AllCCS[M+H-H2O]+186.532859911
AllCCS[M+NH4]+191.732859911
AllCCS[M+Na]+192.532859911
AllCCS[M-H]-186.232859911
AllCCS[M+Na-2H]-188.232859911
AllCCS[M+HCOO]-190.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Ethyl oleateCCCCCCCC\C=C\CCCCCCCC(=O)OCC2502.7Standard polar33892256
Ethyl oleateCCCCCCCC\C=C\CCCCCCCC(=O)OCC2124.0Standard non polar33892256
Ethyl oleateCCCCCCCC\C=C\CCCCCCCC(=O)OCC2196.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Ethyl oleate EI-B (Non-derivatized)splash10-0udi-9310000000-09258099745f0ed4ee7d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl oleate EI-B (Non-derivatized)splash10-0udi-9310000000-09258099745f0ed4ee7d2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethyl oleate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kts-4790000000-b8ac12263c8a2335c3082017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethyl oleate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl oleate 10V, Positive-QTOFsplash10-03di-1179000000-b8150ed46b6787b04ea32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl oleate 20V, Positive-QTOFsplash10-02g2-6591000000-96a12d45ca808758485a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl oleate 40V, Positive-QTOFsplash10-00kf-9830000000-273defed8a72312427f12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl oleate 10V, Negative-QTOFsplash10-0bt9-1069000000-ab88912a0d39dbcb4b282017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl oleate 20V, Negative-QTOFsplash10-08fs-5093000000-a014d9c80189c6faac522017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl oleate 40V, Negative-QTOFsplash10-052p-9050000000-99b1b1781e305d1f8eea2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl oleate 10V, Positive-QTOFsplash10-03di-3289000000-a0053e1896fa156967bc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl oleate 20V, Positive-QTOFsplash10-07vj-9531000000-5df584a9282dc2d34ad12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl oleate 40V, Positive-QTOFsplash10-0a4l-9100000000-4c209b6ad923ce3d8c962021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl oleate 10V, Negative-QTOFsplash10-03di-0094000000-17b5f218fc28b0ecf5842021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl oleate 20V, Negative-QTOFsplash10-03di-2091000000-cf990ca8c6f6662bc54e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl oleate 40V, Negative-QTOFsplash10-0006-9120000000-49bf5a0d3233aa63e0662021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012859
KNApSAcK IDC00030760
Chemspider ID4516584
KEGG Compound IDC03425
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEthyl oleate
METLIN IDNot Available
PubChem Compound5364430
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1023041
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Holian O, Ruiz C, Kumar R, Nyhus LM: Response of brain protein kinase C isozymes to ethyl oleate, an alcohol metabolite. Brain Res. 1991 Aug 30;558(1):98-100. [PubMed:1933386 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.