Record Information
Version1.0
Created at2020-03-18 23:23:55 UTC
Updated at2020-12-07 19:07:04 UTC
CannabisDB IDCDB000077
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common 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 ( Ref:DOI ). Linoleic acid is an essential fatty acid that humans do not synthesize and must obtain from diet. Methyl linoleate is a simple ester found in cannabis plant (PMID: 6991645 ) and is found in clove bud and fruit, garlic bulb, jasmin, white mustard, parsley leaf oil and witch hazel leaf oil ( Ref:DOI #tooccur) . It is part of a mixture with methyl linolenate (*FEMA 3411*) which is used as a flavouring ingredient in condiments and spices.
Structure
Thumb
Synonyms
ValueSource
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
Chemical FormulaC19H34O2
Average Molecular Weight294.47
Monoisotopic Molecular Weight294.2559
IUPAC Namemethyl (9E,12Z)-octadeca-9,12-dienoate
Traditional Namemethyl (9E,12Z)-octadeca-9,12-dienoate
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-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 DescriptorsNot Available
Ontology
Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
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
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012761
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5462988
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]