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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:12:27 UTC
Update Date2019-07-23 06:15:54 UTC
HMDB IDHMDB0034381
Secondary Accession Numbers
  • HMDB34381
Metabolite Identification
Common NameMethyl linoleate
DescriptionMethyl linoleate is found in cloves. It is part of a mixture with methyl linolenate (*FEMA 3411*) which is used as a flavouring ingredient. Methyl linoleate belongs to the family of lineolic acids and derivatives.
Structure
Data?1563862554
Synonyms
ValueSource
1-O-Methyl (9Z,12Z)-octadecadienoateChEBI
Linoleic acid methyl esterChEBI
Methyl 9-cis,12-cis-octadecadienoateChEBI
1-O-Methyl (9Z,12Z)-octadecadienoic acidGenerator
Linoleate methyl esterGenerator
Methyl 9-cis,12-cis-octadecadienoic acidGenerator
Methyl linoleic acidGenerator
Methyl linoleate, (Z,e)-isomerHMDB
Methyl linoleate, 1-(14)C-labeled, (Z,Z)-isomerHMDB
Methyl linoleate, (e,Z)-isomerHMDB
Methyl linoleate, (e,e)-isomerHMDB
(9Z,12Z)-9,12-Octadecadienoic acid methyl esterHMDB
(9Z,12Z)-Octadecadienoic acid methyl esterHMDB
(Z,Z)-9,12-Octadecadienoic acid methyl esterHMDB
Methyl (9Z,12Z)-octadeca-9,12-dienoateHMDB
Methyl (9Z,12Z)-octadecadienoateHMDB
Methyl (Z,Z)-9,12-octadecadienoateHMDB
Methyl cis,cis-9,12-octadecadienoateHMDB
Methyl cis-9,cis-12 linoleateHMDB
Methyl cis-9,cis-12-octadecadienoateHMDB
Methyl octadec-9,12-dienoateHMDB
Methyl linoleateHMDB
Chemical FormulaC19H34O2
Average Molecular Weight294.4721
Monoisotopic Molecular Weight294.255880332
IUPAC Namemethyl (9Z,12Z)-octadeca-9,12-dienoate
Traditional Namemethyl linoleate
CAS Registry Number112-63-0
SMILES
CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC
InChI Identifier
InChI=1S/C19H34O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19(20)21-2/h7-8,10-11H,3-6,9,12-18H2,1-2H3/b8-7-,11-10-
InChI KeyWTTJVINHCBCLGX-NQLNTKRDSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassLineolic acids and derivatives
Direct ParentLineolic acids and derivatives
Alternative Parents
Substituents
  • Octadecanoid
  • Fatty acid methyl ester
  • Fatty acid ester
  • Methyl 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 Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-35 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP6.82Not Available
Predicted Properties
PropertyValueSource
Water Solubility5.1e-05 g/LALOGPS
logP6.95ALOGPS
logP6.57ChemAxon
logS-6.8ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity93.29 m³·mol⁻¹ChemAxon
Polarizability37.67 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001j-9600000000-a791ce5d57e2c9865a43Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-0090000000-135ec398fe08f292b8cfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-4590000000-4fb4c6d3653c76835862Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00rl-8950000000-7a00ea1019fa5ce9dd78Spectrum
MSMass Spectrum (Electron Ionization)splash10-05o1-9300000000-265bc399b065640c1fefSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
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
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5284421
PDB IDNot Available
ChEBI ID69080
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.