Record Information
Version1.0
Creation date2010-04-08 22:05:35 UTC
Update date2019-11-26 02:58:12 UTC
Primary IDFDB002943
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGamolenic acid
DescriptionA minor component of many animal lipids Although GLA is an n?6 fatty acid, a type of acid which is generally pro-inflammatory, it has anti-inflammatory properties. (See discussion at Essential fatty acid interactions: The paradox of dietary GLA.); An omega-6 fatty acid produced in the body as the delta 6-desaturase metabolite of linoleic acid. It is converted to dihomo-gamma-linolenic acid, a biosynthetic precursor of monoenoic prostaglandins such as PGE1. (From Merck Index, 11th ed) -- Pubchem; From GLA, the body forms dihomo-?-linolenic acid (DGLA). This is one of the body's three sources of eicosanoids (along with AA and EPA.) DGLA is the precursor of the prostaglandin PGH1, which in turn forms PGE1 and the thromboxane TXA1. PGE1 has a role in regulation of immune system function and is used as the medicine alprostadil. TXA1 modulates the pro-inflammatory properties of the thromboxane TXA2.; GLA is categorized as an n?6 (also called ??6 or omega-6) fatty acid, meaning that the first double bond on the methyl end (designated with n or ?) is the sixth bond. In physiological literature, GLA is designated as 18:3 (n?6). Chemically, GLA is a carboxylic acid with an 18-carbon chain and three cis double bonds. It is an isomer of ?-linolenic acid, which is the n?3 fatty acid found in flax seed.; The human body produces GLA from linoleic acid (LA). This reaction is catalyzed by ?6-desaturase (D6D), an enzyme which allows the creation of a double bond on the sixth carbon counting from the carboxyl terminus. LA is consumed sufficiently in most diets, from such abundant sources as cooking oils and meats. However, a lack of GLA can occur when there is a reduction of the efficiency of the D6D conversion (for instance, as people grow older or when there are specific dietary deficiencies) or in disease states where there is excessive consumption of GLA metabolites.; ?-Linolenic acid (gamma-linolenic acid or GLA, sometimes called gamoleic acid) is a fatty acid found primarily in vegetable oils. It is sold as a dietary supplement for treating problems with inflammation and auto-immune diseases. The efficacy of such use is disputed.
CAS Number506-26-3
Structure
Thumb
Synonyms
SynonymSource
GamolenateGenerator
(6,9,12)-linolenatebiospider
(6,9,12)-linolenic acidbiospider
(6Z,9Z,12Z)-octadeca-6,9,12-trienoic acidbiospider
(6Z,9Z,12Z)-Octadecatrienoatebiospider
(6Z,9Z,12Z)-Octadecatrienoic acidbiospider
(Z,Z,Z)-6,9,12-Octadecatrienoatebiospider
(Z,Z,Z)-6,9,12-Octadecatrienoic acidbiospider
«gamma»-linolenic acidbiospider
18:3 (N-6)ChEBI
6-cis,9-cis,12-cis-OctadecatrienoateGenerator
6-cis,9-cis,12-cis-Octadecatrienoic acidbiospider
6,9,12-all-cis-Octadecatrienoatebiospider
6,9,12-all-cis-Octadecatrienoic acidbiospider
6,9,12-Octadecatrienoatebiospider
6,9,12-Octadecatrienoic acidbiospider
6,9,12-Octadecatrienoic acid, (6Z,9Z,12Z)-biospider
6,9,12-Octadecatrienoic acid, (Z,Z,Z)-biospider
6(Z),9(Z),12(Z)-Octadecatrienoatebiospider
6(Z),9(Z),12(Z)-Octadecatrienoic acidbiospider
6Z,9Z,12Z-octadecatrienoatebiospider
6Z,9Z,12Z-octadecatrienoic acidbiospider
Acido gamolenicobiospider
Acidum gamolenicumbiospider
all-cis-6,9,12-octadecatrienoatebiospider
all-cis-6,9,12-octadecatrienoic acidbiospider
C18:3 (N-6)ChEBI
C18:3, N-6,9,12 all-cisChEBI
cis-6, cis-9, cis-12-octadecatrienoic acidbiospider
cis-6,cis-9,cis-12-Octadecatrienoic acidbiospider
cis-Delta(6,9,12)-octadecatrienoatebiospider
cis-Delta(6,9,12)-octadecatrienoic acidbiospider
cis-δ(6,9,12)-octadecatrienoateGenerator
cis-δ(6,9,12)-octadecatrienoic acidGenerator
cis,cis,cis-6,9,12-Octadecatrienoic acidbiospider
Efamastbiospider
Efemastdb_source
Efomasedb_source
Epogamdb_source
g-LinolenateGenerator
g-Linolenic aciddb_source
g-LinolensaeureGenerator
Gamma-linolenatebiospider
Gamma-linolenic acidbiospider
gamma-LinolensaeureChEBI
Gamma-llnolenic acidbiospider
Gammalinolenic aciddb_source
Gammolindb_source
GamoleateGenerator
Gamoleic acidChEBI
Gamolenic acidbiospider
Gamolenic acid (inn)biospider
Gamolenic acid [inn:ban]biospider
Gamolenic acid, BAN, INNdb_source
GLAdb_source
Liglabiospider
Octadeca-6,9,12-triensaeureChEBI
Unigamdb_source
Viacutanbiospider
γ-linolenateGenerator
γ-linolenic acidGenerator
γ-linolensaeureGenerator
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
Polarizability33.97 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC18H30O2
IUPAC name(6Z,9E,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-XQYVMNDBSA-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 DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 77.65%; H 10.86%; O 11.49%DFC
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
SpectraNot Available
ChemSpider ID4444436
ChEMBL IDCHEMBL464982
KEGG Compound IDC06426
Pubchem Compound ID5280933
Pubchem Substance IDNot Available
ChEBI ID28661
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03073
CRC / DFC (Dictionary of Food Compounds) IDCPL98-G:CPL99-H
EAFUS IDNot Available
Dr. Duke IDGAMMA-LINOLENIC-ACID
BIGG ID48234
KNApSAcK IDC00001226
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDgamma-Linolenic acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Alpha-reductase inhibitor23924 An agent that blocks the conversion of testosterone to dihydrotestosterone, reducing androgenic effects. Therapeutically, it treats conditions like benign prostatic hyperplasia, androgenetic alopecia, and acne, by decreasing sebum production and slowing hair loss.DUKE
Anti-acne50177 An agent that reduces acne symptoms, commonly used in managing acne vulgaris by minimizing oil production, preventing clogged pores, and decreasing bacterial growth, thereby reducing inflammation and promoting healthy skin.DUKE
Anti-aggregantAn agent that prevents platelet aggregation, reducing blood clot formation. Its biological role is to inhibit platelet activation, and its therapeutic applications include preventing thrombosis and stroke. Key medical uses include treating cardiovascular diseases, such as myocardial infarction and atrial fibrillation, and managing conditions that increase the risk of blood clots.DUKE
Anti-alcoholic52217 An agent that reduces alcohol cravings and withdrawal symptoms, commonly used in managing alcohol dependence and addiction, aiding in the treatment of alcohol use disorder by blocking the rewarding aspects of alcohol consumption.DUKE
Anti-arthritic52217 An agent that reduces joint inflammation and alleviates symptoms of arthritis, commonly used in managing rheumatoid arthritis, osteoarthritis, and other inflammatory joint disorders, to improve mobility and quality of life.DUKE
Anti asphycticAn agent that enhances the blood's ability to carry oxygen, playing a crucial role in preventing hypoxia. Therapeutically, it is used to treat conditions where oxygen delivery is compromised, such as high-altitude sickness, anemia, and respiratory disorders, improving oxygenation and reducing symptoms of asphyxiation.DUKE
Anti-atherosclerotic38070 An agent that prevents or slows the formation of atherosclerosis, a condition characterized by plaque buildup in arteries. It reduces inflammation, improves lipid profiles, and inhibits platelet aggregation, commonly used to manage cardiovascular diseases, such as coronary artery disease, and prevent heart attacks and strokes.DUKE
Anti eczemic52217 An agent that reduces inflammation and itching, commonly used to manage eczema symptoms, atopic dermatitis, and other skin allergies, providing relief and preventing flare-ups.DUKE
Anti hypercholesterolemicAn agent that prevents or controls an increase of cholesterol in the blood, playing a crucial role in reducing cardiovascular risk. Therapeutically, it helps manage hypercholesterolemia, preventing plaque buildup and lowering the risk of heart disease, making it a key treatment for conditions like atherosclerosis and coronary artery disease.DUKE
Anti-menorrhagic52217 An agent that reduces heavy menstrual bleeding, playing a biological role in regulating menstrual flow. Therapeutically, it is used to treat menorrhagia, with key medical applications including managing excessive uterine bleeding, dysmenorrhea, and menstrual disorders.DUKE
Anti monosodium-glutamateAn antidote for MSG poisoning, neutralizing excessive glutamate effects. Biologically, it regulates glutamate levels, mitigating neurotoxicity. Therapeutically, it's used to treat MSG-induced adverse reactions, such as headaches and nausea, and may have applications in managing conditions like migraines and neuropathic pain.DUKE
Anti-obesity52217 An agent that reduces body weight, commonly used in managing obesity and related disorders, by regulating appetite, metabolism, and fat storage, with therapeutic applications in preventing chronic diseases such as diabetes and cardiovascular disease.DUKE
Anti premenstrual syndrome52217 An agent that alleviates symptoms of premenstrual syndrome (PMS), reducing physical and emotional discomfort. Its biological role involves regulating hormonal fluctuations, and its therapeutic applications include managing mood swings, bloating, and breast tenderness. Key medical uses include treating PMS, premenstrual dysphoric disorder (PMDD), and other menstrual-related disorders.DUKE
Anti-prostatiticAn agent that relieves prostatitis, reducing inflammation of the prostate gland, and is used to treat benign prostatic hyperplasia (BPH) and chronic pelvic pain syndrome.DUKE
Anti Raynaud's52217 An agent that improves blood flow to extremities, reducing vasospasm and relieving symptoms of Raynaud's disease, commonly used to manage cold-induced digital ulcers, pain, and discoloration in fingers and toes.DUKE
Antitumor35610 An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.DUKE
HypocholesterolemicAn agent that lowers cholesterol levels in the blood, playing a crucial role in preventing cardiovascular disease. Therapeutically, it is used to manage hyperlipidemia and reduce the risk of heart disease, with key medical applications including the treatment of high cholesterol, atherosclerosis, and coronary artery disease.DUKE
HypotensiveAn agent that lowers blood pressure, playing a biological role in regulating cardiovascular function. Therapeutically, it's used to manage hypertension, heart failure, and angina, with key medical applications in preventing stroke, kidney disease, and cardiac complications.DUKE
Immunomodulator50846 An agent that regulates the immune system, modifying its response to maintain balance. Therapeutically, it's used to treat autoimmune diseases, prevent transplant rejection, and manage chronic inflammatory conditions, such as rheumatoid arthritis and multiple sclerosis.DUKE
Vasodilator35620 An agent that widens blood vessels, reducing blood pressure and increasing blood flow. It plays a biological role in regulating cardiovascular function. Therapeutically, vasodilators are used to treat conditions such as hypertension, angina, and heart failure, improving oxygen delivery and reducing cardiac workload.DUKE
Enzymes
NameGene NameUniProt ID
Bile acid-CoA:amino acid N-acyltransferaseBAATQ14032
Cytosolic acyl coenzyme A thioester hydrolaseACOT7O00154
Acyl-coenzyme A thioesterase 2, mitochondrialACOT2P49753
Acyl-coenzyme A thioesterase 4ACOT4Q8N9L9
Acyl-coenzyme A thioesterase 8ACOT8O14734
Acyl-coenzyme A thioesterase 1ACOT1Q86TX2
Pathways
NameSMPDB LinkKEGG Link
Alpha Linolenic Acid and Linoleic Acid MetabolismSMP00018 map00592
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).