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γ-Linolenic acid (FDB112408)

Record Information
Version1.0
Creation date2020-04-21 17:22:28 UTC
Update date2020-09-17 15:33:12 UTC
Primary IDFDB112408
Secondary Accession NumbersNot Available
Chemical Information
FooDB Nameγ-Linolenic acid
DescriptionGamma-Linolenic acid is also known as 18:3 (N-6), gamolenic acid or gamma-linolensaeure. It is an omega-6 polyunsaturated fatty acid (PUFA) also referred to as 9,12-octadecatrienoic acid (cis-6, cis-9, cis-12- octadecatrienoic acid). It 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. gamma-Linolenic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. It is found largely in human milk and other botanical sources. Gamma-Linolenic acid is found in varying amounts in edible hemp seeds, oats, barley and spirulina. Gamolenic acid is also found in some fungal sources and is present naturally in the form of triglycerides. Gamolenic acid may be found in over-the-counter dietary supplements. Gamma-Linolenic acid is an omega-6 fatty acid produced in the body as the delta 6-desaturase metabolite of linoleic acid. It is converted into dihomo-gamma-linolenic acid, a biosynthetic precursor of monoenoic prostaglandins such as Prostaglandin E1(PGE1). Evening primrose oil, containing 7-14% gamma-linolenic acid, has been investigated for clinical use in menopausal syndrome, diabetic neuropathy, breast pain (PMID: 27083549) and eczema. It has been questioned if evening primrose oil, containing gamma-linolenic acid, helped alleviate atopic eczema (PMID: 14670851). However, its effectiveness in treating eczema was demonstrated in a study where the topical application of borage seed oil (with higher concentrations of gamma linolenic acid than evening primrose oil) reduced symptoms of atopic dermatitis in a double-blind, placebo-controlled clinical trial (PMID: 18078406). Various clinical indications of gamolenic acid have been studied, including rheumatoid arthritis, atopic eczema, acute respiratory distress syndrome, asthma, premenstrual syndrome, cardiovascular disease, ulcerative colitis, ADHD, cancer, osteoporosis, diabetic neuropathy, and insomnia ( PMID: 27083549; PMID: 27083549).
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00025 g/LALOGPS
logP6.59ALOGPS
logP6.06ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)4.92ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity89.64 m³·mol⁻¹ChemAxon
Polarizability33.8 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC18H30O2
IUPAC name(6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid
InChI IdentifierInChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10,12-13H,2-5,8,11,14-17H2,1H3,(H,19,20)/b7-6-,10-9-,13-12-
InChI KeyVZCCETWTMQHEPK-QNEBEIHSSA-N
Isomeric SMILESCCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O
Average Molecular Weight278.4296
Monoisotopic Molecular Weight278.224580204
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
  • Long-chain fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
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
EI-MSMass Spectrum (Electron Ionization)splash10-00nf-9200000000-cf911df79059a750cb2a2015-03-01View Spectrum
GC-MSγ-Linolenic acid, 1 TMS, GC-MS Spectrumsplash10-005c-9800000000-7b6e7a36b048f5ed69bdSpectrum
GC-MSγ-Linolenic acid, non-derivatized, GC-MS Spectrumsplash10-00b9-9300000000-254ecb989081fdc719d2Spectrum
GC-MSγ-Linolenic acid, non-derivatized, GC-MS Spectrumsplash10-005c-9800000000-7b6e7a36b048f5ed69bdSpectrum
Predicted GC-MSγ-Linolenic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9650000000-eec5566c0f0f90bf0049Spectrum
Predicted GC-MSγ-Linolenic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-007c-9431000000-b239852c91e567668780Spectrum
Predicted GC-MSγ-Linolenic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSγ-Linolenic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-005l-0902100000-6fc8730bd28daa779b662017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-005l-0902100000-6fc8730bd28daa779b662017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-005l-0902100000-6fc8730bd28daa779b662017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-005l-0902100000-6fc8730bd28daa779b662017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0090000000-143e6ddfa05656a4c4da2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0090000000-0b9ba563ad074fe141e82017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0090000000-63bf7d731625d55779782017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0090000000-fbc4e202a8b26c91dc9e2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0090000000-b56d00321ab0921fe7b72017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-0090000000-dcae4273443fd52bbb032017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-143e6ddfa05656a4c4da2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-0b9ba563ad074fe141e82017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-63bf7d731625d55779782017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-004i-0090000000-370b301c8afc435a0ce12020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-003s-9850000000-54163d6f895368b9032c2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, positivesplash10-001i-9000000000-e6cdb81ac5675944be822020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-003s-9750000000-d1947011d4fc6a28a1352021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-004i-0090000000-0b9ba563ad074fe141e82021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-370b301c8afc435a0ce12021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0190000000-6b136607b48b316678012016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-4790000000-5046458d5d3e3c2285182016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mo-8930000000-852d50a19eb0b0df729b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-ab643cae783eb66bf1312016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-1090000000-abce276de392be9d7d3f2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9230000000-40a41feed498373e54d22016-08-04View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
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
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference