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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:12:27 UTC
Update Date2022-03-07 02:54:05 UTC
HMDB IDHMDB0034381
Secondary Accession Numbers
  • HMDB34381
Metabolite Identification
Common NameMethyl linoleate
DescriptionMethyl linoleate 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. Based on a literature review a significant number of articles have been published on Methyl linoleate.
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
1-O-Methyl (9Z,12Z)-octadecadienoateHMDB
1-O-Methyl (9Z,12Z)-octadecadienoic acidHMDB
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
Physiological effect
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-35 °CNot Available
Boiling Point373.00 to 374.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.02 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP6.82Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Baker183.17930932474
[M+H]+Baker187.20130932474
[M-H]-Not Available183.179http://allccs.zhulab.cn/database/detail?ID=AllCCS00001856
[M+H]+Not Available187.201http://allccs.zhulab.cn/database/detail?ID=AllCCS00001856
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+180.57630932474
DeepCCS[M-H]-178.21830932474
DeepCCS[M-2H]-211.10530932474
DeepCCS[M+Na]+186.6730932474
AllCCS[M+H]+183.232859911
AllCCS[M+H-H2O]+180.232859911
AllCCS[M+NH4]+185.932859911
AllCCS[M+Na]+186.732859911
AllCCS[M-H]-181.632859911
AllCCS[M+Na-2H]-183.332859911
AllCCS[M+HCOO]-185.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Methyl linoleateCCCCC\C=C/C\C=C/CCCCCCCC(=O)OC2501.9Standard polar33892256
Methyl linoleateCCCCC\C=C/C\C=C/CCCCCCCC(=O)OC2029.8Standard non polar33892256
Methyl linoleateCCCCC\C=C/C\C=C/CCCCCCCC(=O)OC2127.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Methyl linoleate GC-MS (Non-derivatized)splash10-001j-9600000000-a791ce5d57e2c9865a432014-06-16HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyl linoleate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-05o1-9300000000-265bc399b065640c1fef2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl linoleate 10V, Positive-QTOFsplash10-01ot-0090000000-135ec398fe08f292b8cf2018-11-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl linoleate 20V, Positive-QTOFsplash10-00dr-4590000000-4fb4c6d3653c768358622018-11-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl linoleate 40V, Positive-QTOFsplash10-00rl-8950000000-7a00ea1019fa5ce9dd782018-11-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl linoleate 10V, Positive-QTOFsplash10-0002-3390000000-5b7cf5465ccc9473b8e92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl linoleate 20V, Positive-QTOFsplash10-000t-9520000000-fcc996dac4de8256585f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl linoleate 40V, Positive-QTOFsplash10-0apm-9000000000-65f2ad7eab0843dd7de92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl linoleate 10V, Negative-QTOFsplash10-03dl-0090000000-6e2818910e3b1bba7c332021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl linoleate 20V, Negative-QTOFsplash10-01ox-1090000000-08c19eb9f4800067800b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl linoleate 40V, Negative-QTOFsplash10-0a4l-9330000000-766211cd091c6a0f9f082021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
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 IDNot Available
KNApSAcK IDC00030757
Chemspider ID4447491
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
MarkerDB IDNot Available
Good Scents IDrw1260021
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.