Gamolenic acid (CHEM018796)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:32:27 UTC
Update Date2016-10-28 10:02:29 UTC
Accession NumberCHEM018796
Identification
Common NameGamolenic acid
ClassSmall Molecule
DescriptionGamolenic acid, or gamma-linolenic acid (γ-Linolenic acid) or GLA, is an essential fatty acid (EFA) comprised of 18 carbon atoms with three double bonds that is most commonly found in human milk and other botanical sources . It is an omega-6 polyunsaturated fatty acid (PUFA) also referred to as 18:3n-6; 6,9,12-octadecatrienoic acid; and cis-6, cis-9, cis-12- octadecatrienoic acid . gamma-Linolenic acid is produced minimally in the body as the delta 6-desaturase metabolite of . It is converted to , a biosynthetic precursor of monoenoic prostaglandins such as PGE1. While gamma-Linolenic acid is found naturally in the fatty acid fractions of some plant seed oils , and are rich sources of gamolenic acid. Evening primrose oil has been investigated for clinical use in menopausal syndrome, diabetic neuropathy, and breast pain, where gamma-Linolenic acid is present at concentrations of 7-14% . gamma-Linolenic acid may be found in over-the-counter dietary supplements. gamma-Linolenic acid is also found in some fungal sources and also present naturally in the form of triglycerides . Various clinical indications of gamma-Linolenic 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.
Contaminant Sources
  • Cosmetic Chemicals
  • FooDB Chemicals
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(6,9,12)-Linolenic acidChEBI
(6Z,9Z,12Z)-Octadecatrienoic acidChEBI
(Z,Z,Z)-6,9,12-Octadecatrienoic acidChEBI
18:3 (N-6)ChEBI
6,9,12-Octadecatrienoic acidChEBI
6-cis,9-cis,12-cis-Octadecatrienoic acidChEBI
all-cis-6,9,12-Octadecatrienoic acidChEBI
C18:3 (N-6)ChEBI
C18:3, N-6,9,12 all-cisChEBI
cis-Delta(6,9,12)-Octadecatrienoic acidChEBI
gamma-LinolensaeureChEBI
Gamoleic acidChEBI
Gamolenic acidChEBI
GLAChEBI
Octadeca-6,9,12-triensaeureChEBI
(6,9,12)-LinolenateGenerator
(6Z,9Z,12Z)-OctadecatrienoateGenerator
(Z,Z,Z)-6,9,12-OctadecatrienoateGenerator
6,9,12-OctadecatrienoateGenerator
6-cis,9-cis,12-cis-OctadecatrienoateGenerator
all-cis-6,9,12-OctadecatrienoateGenerator
cis-delta(6,9,12)-OctadecatrienoateGenerator
cis-Δ(6,9,12)-octadecatrienoateGenerator
cis-Δ(6,9,12)-octadecatrienoic acidGenerator
g-LinolensaeureGenerator
Γ-linolensaeureGenerator
GamoleateGenerator
GamolenateGenerator
g-LinolenateGenerator
g-Linolenic acidGenerator
gamma-LinolenateGenerator
Γ-linolenateGenerator
Γ-linolenic acidGenerator
6(Z),9(Z),12(Z)-OctadecatrienoateHMDB
6(Z),9(Z),12(Z)-Octadecatrienoic acidHMDB
6,9,12-all-cis-OctadecatrienoateHMDB
6,9,12-all-cis-Octadecatrienoic acidHMDB
6Z,9Z,12Z-OctadecatrienoateHMDB
6Z,9Z,12Z-Octadecatrienoic acidHMDB
gamma-Llnolenic acidHMDB
LiglaHMDB
Acid, gamma-linolenicHMDB
Acid, gamolenicHMDB
gamma Linolenic acidHMDB
FA(18:3(6Z,9Z,12Z))HMDB
FA(18:3n6)HMDB
LinolenateHMDB
gamma-Linolenic acidKEGG
(6Z,9Z,12Z)-6,9,12-Octadecatrienoic acidPhytoBank
(Z,Z,Z)-6,9,12-Octatrienoic acidPhytoBank
cis,cis,cis-6,9,12-Octadecatrienoic acidPhytoBank
cis-6,cis-9,cis-12-Octadecatrienoic acidPhytoBank
Chemical FormulaC18H30O2
Average Molecular Mass278.430 g/mol
Monoisotopic Mass278.225 g/mol
CAS Registry Number506-26-3
IUPAC Name(6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid
Traditional Namegamma linolenic acid
SMILESCCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O
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
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
  • 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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-005c-9800000000-7b6e7a36b048f5ed69bdSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00b9-9300000000-254ecb989081fdc719d2Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-005c-9800000000-7b6e7a36b048f5ed69bdSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9650000000-eec5566c0f0f90bf0049Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-007c-9431000000-b239852c91e567668780Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-005l-0902100000-6fc8730bd28daa779b66Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-005l-0902100000-6fc8730bd28daa779b66Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-005l-0902100000-6fc8730bd28daa779b66Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-005l-0902100000-6fc8730bd28daa779b66Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0090000000-143e6ddfa05656a4c4daSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0090000000-0b9ba563ad074fe141e8Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0090000000-63bf7d731625d5577978Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0090000000-fbc4e202a8b26c91dc9eSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0090000000-b56d00321ab0921fe7b7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-0090000000-dcae4273443fd52bbb03Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-143e6ddfa05656a4c4daSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-0b9ba563ad074fe141e8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-63bf7d731625d5577978Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-004i-0090000000-370b301c8afc435a0ce1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-003s-9850000000-54163d6f895368b9032cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, positivesplash10-001i-9000000000-e6cdb81ac5675944be82Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-003s-9750000000-d1947011d4fc6a28a135Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-004i-0090000000-0b9ba563ad074fe141e8Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-370b301c8afc435a0ce1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0190000000-6b136607b48b31667801Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-4790000000-5046458d5d3e3c228518Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mo-8930000000-852d50a19eb0b0df729bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-ab643cae783eb66bf131Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-1090000000-abce276de392be9d7d3fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9230000000-40a41feed498373e54d2Spectrum
MSMass Spectrum (Electron Ionization)splash10-00nf-9200000000-cf911df79059a750cb2aSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB13854
HMDB IDHMDB0003073
FooDB IDFDB002943
Phenol Explorer IDNot Available
KNApSAcK IDC00001226
BiGG ID48234
BioCyc IDCPD-8117
METLIN ID386
PDB IDNot Available
Wikipedia LinkGamma-Linolenic_acid
Chemspider ID4444436
ChEBI ID28661
PubChem Compound ID5280933
Kegg Compound IDC06426
YMDB IDNot Available
ECMDB IDM2MDB004734
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.
2. Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3.
3. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386
4. M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189
5. Gema H; Kavadia A; Dimou D; Tsagou V; Komaitis M; Aggelis G Production of gamma-linolenic acid by Cunninghamella echinulata cultivated on glucose and orange peel. Applied microbiology and biotechnology (2002), 58(3), 303-7.
6. Levy RJ, Lian JB: gamma-Carboxyglutamate excretion and warfarin therapy. Clin Pharmacol Ther. 1979 May;25(5 Pt 1):562-70.
7. Bolton-Smith C, Woodward M, Tavendale R: Evidence for age-related differences in the fatty acid composition of human adipose tissue, independent of diet. Eur J Clin Nutr. 1997 Sep;51(9):619-24.
8. Purasiri P, Mckechnie A, Heys SD, Eremin O: Modulation in vitro of human natural cytotoxicity, lymphocyte proliferative response to mitogens and cytokine production by essential fatty acids. Immunology. 1997 Oct;92(2):166-72.
9. Ziboh VA, Miller CC, Cho Y: Metabolism of polyunsaturated fatty acids by skin epidermal enzymes: generation of antiinflammatory and antiproliferative metabolites. Am J Clin Nutr. 2000 Jan;71(1 Suppl):361S-6S.
10. Magnusson G, Boberg M, Cederblad G, Meurling S: Plasma and tissue levels of lipids, fatty acids and plasma carnitine in neonates receiving a new fat emulsion. Acta Paediatr. 1997 Jun;86(6):638-44.
11. Kankaanpaa PE, Salminen SJ, Isolauri E, Lee YK: The influence of polyunsaturated fatty acids on probiotic growth and adhesion. FEMS Microbiol Lett. 2001 Jan 15;194(2):149-53.
12. Melnik BC, Plewig G: Is the origin of atopy linked to deficient conversion of omega-6-fatty acids to prostaglandin E1? J Am Acad Dermatol. 1989 Sep;21(3 Pt 1):557-63.
13. Whitaker DK, Cilliers J, de Beer C: Evening primrose oil (Epogam) in the treatment of chronic hand dermatitis: disappointing therapeutic results. Dermatology. 1996;193(2):115-20.
14. Kankaanpaa P, Nurmela K, Erkkila A, Kalliomaki M, Holmberg-Marttila D, Salminen S, Isolauri E: Polyunsaturated fatty acids in maternal diet, breast milk, and serum lipid fatty acids of infants in relation to atopy. Allergy. 2001 Jul;56(7):633-8.
15. Koletzko B, Sauerwald U, Keicher U, Saule H, Wawatschek S, Bohles H, Bervoets K, Fleith M, Crozier-Willi G: Fatty acid profiles, antioxidant status, and growth of preterm infants fed diets without or with long-chain polyunsaturated fatty acids. A randomized clinical trial. Eur J Nutr. 2003 Oct;42(5):243-53.
16. Leigh-Firbank EC, Minihane AM, Leake DS, Wright JW, Murphy MC, Griffin BA, Williams CM: Eicosapentaenoic acid and docosahexaenoic acid from fish oils: differential associations with lipid responses. Br J Nutr. 2002 May;87(5):435-45.
17. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=11385052
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=24435467
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=9732298