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Methyl linoleate (CHEM003858)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (4)XML
Record Information
Version1.0
Creation Date2014-09-11 05:21:33 UTC
Update Date2016-11-09 01:09:14 UTC
Accession NumberCHEM003858
Identification
Common NameMethyl linoleate
ClassSmall Molecule
DescriptionMethyl linoleate is found in cloves. Methyl linoleate is a mixture with CNB89-S (*FEMA 3411*) is used as a flavouring ingredient Methyl linoleate belongs to the family of Lineolic Acids and Derivatives. These are derivatives of lineolic acid.
Contaminant Sources
  • FooDB Chemicals
  • HPV EPA Chemicals
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Ester
  • Ether
  • Flavouring Agent
  • Food Toxin
  • Household Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 Mass294.472 g/mol
Monoisotopic Mass294.256 g/mol
CAS Registry Number112-63-0
IUPAC Namemethyl (9Z,12Z)-octadeca-9,12-dienoate
Traditional Namemethyl linoleate
SMILESCCCCC\C=C/C\C=C\CCCCCCCC(=O)OC
InChI IdentifierInChI=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-QEFCTBRHSA-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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point-35 °C
Boiling PointNot Available
SolubilityNot 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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSsplash10-001j-9600000000-a791ce5d57e2c9865a43View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-0090000000-135ec398fe08f292b8cfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-4590000000-4fb4c6d3653c76835862View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00rl-8950000000-7a00ea1019fa5ce9dd78View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-3390000000-5b7cf5465ccc9473b8e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-9520000000-fcc996dac4de8256585fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0apm-9000000000-65f2ad7eab0843dd7de9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dl-0090000000-6e2818910e3b1bba7c33View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-1090000000-08c19eb9f4800067800bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9330000000-766211cd091c6a0f9f08View in MoNA
MSMass Spectrum (Electron Ionization)splash10-05o1-9300000000-265bc399b065640c1fefView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0034381
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00030757
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4447491
ChEBI ID69080
PubChem Compound ID5284421
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=22148193
2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
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.
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.
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.
6. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
7. The lipid handbook with CD-ROM