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Showing Compound Methyl linoleate (FDB012761)

Record Information
Version1.0
Creation date2010-04-08 22:10:21 UTC
Update date2020-09-17 15:30:16 UTC
Primary IDFDB012761
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMethyl linoleate
DescriptionMethyl linoleate belongs to the class of organic compounds known as linoleic acids which are derivatives of linoleic acid. Linoleic acid is a doubly unsaturated fatty acid, also known as an omega-6 fatty acid, occurring widely in plant glycosides. Methyl linoleate is an essentially neutral compound that is almost insoluble in water and soluble in alcohol. It has a low oily, fatty, woody odor ( http://www.thegoodscentscompany.com/data/rw1260021.html). Linoleic acid is an essential fatty acid that humans do not synthesize and must obtain from diet. Methyl linoleate is found in clove bud and fruit, garlic bulb, jasmin, white mustard, parsley leaf oil and witch hazel leaf oil (http://www.thegoodscentscompany.com/data/rw1260021.html#tooccur). It is part of a mixture with methyl linolenate (*FEMA 3411*) which is used as a flavouring ingredient in condiments and spices.
CAS Number112-63-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Methyl linoleic acidGenerator
(Z,Z)-9,12-Octadecadienoic acid methyl esterHMDB
9,12-Octadecadienoic acid (9Z,12Z)-, methyl esterHMDB
9,12-Octadecadienoic acid (Z,Z)-, methyl esterHMDB
9,12-Octadecadienoic acid, methyl esterHMDB
9,12-Octadecadienoic acid, methyl ester, (Z,Z)HMDB
cis-9,cis-12-Octadecadienoic acid, methyl esterHMDB
cis-Linoleic acid methyl esterHMDB
Linoleic acid methyl esterHMDB, MeSH
Linoleic acid, methyl esterHMDB
Linoleic acid, methyl ester (8ci)HMDB
Linoleic acid,methyl esterHMDB
Methyl (9Z,12Z)-9,12-octadecadienoateHMDB
Methyl (9Z,12Z)-octadeca-9,12-dienoateHMDB
Methyl (Z,Z)-9,12-octadecadienoateHMDB
Methyl (Z,Z)-9,12-octadienoateHMDB
Methyl 9-cis,12-cis-octadecadienoateHMDB
Methyl cis,cis-9, 12-octadecadienoateHMDB
Methyl cis,cis-9,12-octadecadienoateHMDB
Methyl ester(Z,Z)-9,12-octadecadienoic acidHMDB
Methyl lineoleateHMDB
Methyl linolateHMDB
Methyl linoleate, nativeHMDB
Methyl octadeca-9,12-dienoateHMDB
Methyl octadecadienoateHMDB
Natural methyl linoleateHMDB
Methyl linoleate, (e,e)-isomerMeSH
Methyl linoleate, (e,Z)-isomerMeSH
Methyl linoleate, 1-(14)C-labeled, (Z,Z)-isomerMeSH
Methyl linoleate, (Z,e)-isomerMeSH
(Z,Z)-9,12-octadecadienoic acid methyl esterbiospider
9,12-Octadecadienoic acid, methyl ester, (Z,Z)-biospider
Cis-linoleic acid methyl esterbiospider
Linoleic acid, methyl ester (8CI)biospider
methyl (9Z,12Z)-octadeca-9,12-dienoatebiospider
methyl (Z,Z)-9,12-octadienoatebiospider
Methyl linoleatedb_source
methyl octadeca-9,12-dienoatebiospider
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
Polarizability37.45 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC19H34O2
IUPAC namemethyl (9E,12Z)-octadeca-9,12-dienoate
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
Isomeric SMILESCCCCC\C=C/C\C=C\CCCCCCCC(=O)OC
Average Molecular Weight294.4721
Monoisotopic Molecular Weight294.255880332
Classification
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 DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 77.50%; H 11.64%; O 10.87%DFC
Melting PointMp -35°DFC
Boiling PointBp1 168-170°DFC
Experimental Water SolubilityNot Available
Experimental logP6.82KROP,HB ET AL. (1997)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSMethyl linoleate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-4960000000-3e2046c3fe4225c4af0fSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-0090000000-30a8d024a36c58bde4352016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ds-4690000000-6053e1a84d9455eacd002016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-8930000000-57ad9c296da5432bd2432016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-68faa548b35623072cb42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-1090000000-75a738f3988f24584df92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9140000000-4ae9ea1f9fd46d9625732016-08-03View Spectrum
NMRNot Available
ChemSpider ID4575738
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5462988
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34381
CRC / DFC (Dictionary of Food Compounds) IDHDX10-F:HKR33-H
EAFUS IDNot Available
Dr. Duke IDCIS-LINOLEIC-ACID-METHYL-ESTER|LINOLEIC-ACID-METHYL-ESTER
BIGG IDNot Available
KNApSAcK IDC00030757
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1260021
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bland
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.