Gamolenic acid (CED0003075)

Record Information
Version1.0
Creation Date2016-05-22 05:32:27 UTC
Update Date2026-05-14 19:38:02 UTC
Accession NumberCHEM018796
Identification
Common NameGamolenic acid
ClassSmall Molecule
Description
Gamolenic acid is an organic compound with the chemical formula C18H30O2 and an average molecular weight of 278.43 g/mol. Gamolenic acid belongs to the lineolic acids and derivatives, a subclass of fatty acyls within the organic compounds. This substance is found in or released from 15 recorded sources across several categories. Within healthcare, pharmaceuticals, and veterinary products, it is associated with dermatological preparations. In the sector of food, food processing, and cookware, it is linked to the processing of fish and the preparation of vinegar, wort, wine, or sparkling wine. It is also found in household cleaning and consumer products, specifically tobacco product cases and non-electric simulated smoking devices. Additionally, it is present in electrical and electronic equipment, including antennas, auxiliary devices, colour television systems, line transmission systems, microphones, and three other sources. The recorded route of exposure for gamolenic acid is oral.
Contaminant TypeNot Available
Chemical Structure
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
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-005c-9800000000-7b6e7a36b048f5ed69bdNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00b9-9300000000-254ecb989081fdc719d2Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-005c-9800000000-7b6e7a36b048f5ed69bdNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0006-9650000000-eec5566c0f0f90bf0049Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-007c-9431000000-b239852c91e567668780Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-005l-0902100000-6fc8730bd28daa779b66Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-005l-0902100000-6fc8730bd28daa779b66Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-005l-0902100000-6fc8730bd28daa779b66Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-005l-0902100000-6fc8730bd28daa779b66Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0090000000-143e6ddfa05656a4c4daNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0090000000-0b9ba563ad074fe141e8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0090000000-63bf7d731625d5577978Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0090000000-fbc4e202a8b26c91dc9eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0090000000-b56d00321ab0921fe7b7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0090000000-dcae4273443fd52bbb03Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0090000000-143e6ddfa05656a4c4daNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0090000000-0b9ba563ad074fe141e8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0090000000-63bf7d731625d5577978Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0090000000-370b301c8afc435a0ce1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-003s-9850000000-54163d6f895368b9032cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-9000000000-e6cdb81ac5675944be82Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-003s-9750000000-d1947011d4fc6a28a135Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0090000000-0b9ba563ad074fe141e8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0090000000-370b301c8afc435a0ce1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-9000000000-e6cdb81ac5675944be82Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0090000000-143e6ddfa05656a4c4daNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0090000000-63bf7d731625d5577978Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0090000000-c02dd8adb3dd677e2691Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0090000000-2540991614651cec5a63Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-003s-9750000000-5ac5758f092935e0ecc5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01t9-0190000000-6b136607b48b31667801Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01q9-4790000000-5046458d5d3e3c228518Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05mo-8930000000-852d50a19eb0b0df729bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0090000000-ab643cae783eb66bf131Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0059-1090000000-abce276de392be9d7d3fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9230000000-40a41feed498373e54d2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01t9-3590000000-0dd559838e3a98c2365aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05nb-9610000000-cd705bf10a4dac431fc1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-067m-9100000000-abe381e948c6d03ddab2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0090000000-12da14b99ffff5280158Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-056r-1090000000-ba99061b490cfde4e980Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9410000000-e544bc8102389ff7de46Not AvailableView Spectrum
MSMS Spectrumsplash10-00nf-9200000000-cf911df79059a750cb2aNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, H2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, H2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
6810.0Log mg/kg[3800:12000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
315Dermatological preparationsHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
509Colour Television SystemsElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
528MicrophonesElectrical & Electronic EquipmentNot Available
534Still Video CamerasElectrical & Electronic EquipmentNot Available
536Superconductive Or Hyperconductive Conductors Cables Or Transmission LinesElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
551Processing FishFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
567Tobacco Product CasesHousehold cleaning & consumer productsNot Available
577Watch ChainsHousehold itemsNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
590Lifeboat EquipmentMarine, shipping & aquacultureNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
634BucklesTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Peroxisome proliferator-activated receptor gamma structureClick to view 3D structurePeroxisome proliferator-activated receptor gammaP37231HumansPredicted (SEA)0.155698
Peroxisome proliferator-activated receptor alpha structureClick to view 3D structurePeroxisome proliferator-activated receptor alphaQ07869HumansPredicted (SEA)0.155698
Peroxisome proliferator-activated receptor delta structureClick to view 3D structurePeroxisome proliferator-activated receptor deltaQ03181HumansPredicted (SEA)0.155698
Click to view 3D structureTransient receptor potential cation channel subfamily V member 2Q9WUD2Rattus norvegicusPredicted (SEA)0.389246
Tyrosine-protein phosphatase non-receptor type 1 structureClick to view 3D structureTyrosine-protein phosphatase non-receptor type 1P18031HumansPredicted (SEA)0.389246
Fatty acid-binding protein, adipocyte structureClick to view 3D structureFatty acid-binding protein, adipocyteP15090HumansPredicted (SEA)0.233548
Click to view 3D structureFatty-acid amide hydrolase 1O00519HumansPredicted (SEA)1.47914
Free fatty acid receptor 4 structureClick to view 3D structureFree fatty acid receptor 4Q5NUL3HumansPredicted (SEA)0.0778492
Click to view 3D structureOxoeicosanoid receptor 1Q8TDS5HumansPredicted (SEA)0.0778492
Click to view 3D structureCannabinoid receptor 1P20272Rattus norvegicusPredicted (SEA)2.49118
Free fatty acid receptor 1 structureClick to view 3D structureFree fatty acid receptor 1O14842HumansPredicted (SEA)0.467095
Cannabinoid receptor 1 structureClick to view 3D structureCannabinoid receptor 1P21554HumansPredicted (SEA)4.12601
Cannabinoid receptor 2 structureClick to view 3D structureCannabinoid receptor 2P34972HumansPredicted (SEA)3.65891
Click to view 3D structureCannabinoid receptor 2P47936Mus musculusPredicted (SEA)2.10193
Click to view 3D structureFatty-acid amide hydrolase 1P97612Rattus norvegicusPredicted (SEA)4.12601
Transient receptor potential cation channel subfamily V member 1 structureClick to view 3D structureTransient receptor potential cation channel subfamily V member 1Q8NER1HumansPredicted (SEA)2.56902
Click to view 3D structureCannabinoid receptor 2Q9QZN9Rattus norvegicusPredicted (SEA)0.934191
Click to view 3D structureCannabinoid receptor 1P47746Mus musculusPredicted (SEA)0.934191
G-protein coupled receptor 84 structureClick to view 3D structureG-protein coupled receptor 84Q9NQS5HumansPredicted (SEA)1.71268
Click to view 3D structureTransient receptor potential cation channel subfamily V member 1O35433Rattus norvegicusPredicted (SEA)1.79053
Click to view 3D structureHistone deacetylase 11Q96DB2HumansPredicted (SEA)5.52729
Fatty acid-binding protein, heart structureClick to view 3D structureFatty acid-binding protein, heartP05413HumansPredicted (SEA)0.311397
Click to view 3D structureFatty-acid amide hydrolase 1O08914Mus musculusPredicted (SEA)8.79696
Click to view 3D structureEsteraseA3QR02Chilo suppressalisPredicted (SEA)0.544945
Fatty acid-binding protein 5 structureClick to view 3D structureFatty acid-binding protein 5Q01469HumansPredicted (SEA)0.311397
Concentrations
Not Available
External Links
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