| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:05:35 UTC |
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| Update date | 2019-11-26 02:58:12 UTC |
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| Primary ID | FDB002943 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | Gamolenic acid |
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| Description | A 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. |
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| CAS Number | 506-26-3 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| Not Available | Not Available |
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| Predicted Properties | |
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| Chemical Formula | C18H30O2 |
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| IUPAC name | (6Z,9E,12Z)-octadeca-6,9,12-trienoic acid |
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| InChI Identifier | InChI=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- |
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| InChI Key | VZCCETWTMQHEPK-XQYVMNDBSA-N |
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| Isomeric SMILES | CCCCC\C=C/C\C=C\C\C=C/CCCCC(O)=O |
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| Average Molecular Weight | 278.4296 |
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| Monoisotopic Molecular Weight | 278.224580204 |
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| Classification |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Fatty Acyls |
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| Sub Class | Lineolic acids and derivatives |
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| Direct Parent | Lineolic acids and derivatives |
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| Alternative Parents | |
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| 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
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Ontology | No ontology term |
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| Physico-Chemical Properties |
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| Physico-Chemical Properties - Experimental | | Property | Value | Reference |
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| Physical state | Solid | |
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| Physical Description | Not Available | |
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| Mass Composition | C 77.65%; H 10.86%; O 11.49% | DFC |
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| Melting Point | Not Available | |
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| Boiling Point | Not Available | |
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| Experimental Water Solubility | Not Available | |
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| Experimental logP | Not Available | |
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| Experimental pKa | Not Available | |
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| Isoelectric point | Not Available | |
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| Charge | Not Available | |
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| Optical Rotation | Not Available | |
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| Spectroscopic UV Data | Not Available | |
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| Density | Not Available | |
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| Refractive Index | Not Available | |
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| Spectra |
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| Spectra | Not Available |
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| External Links |
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| ChemSpider ID | 4444436 |
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| ChEMBL ID | CHEMBL464982 |
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| KEGG Compound ID | C06426 |
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| Pubchem Compound ID | 5280933 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | 28661 |
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| Phenol-Explorer ID | Not Available |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB03073 |
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| CRC / DFC (Dictionary of Food Compounds) ID | CPL98-G:CPL99-H |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | GAMMA-LINOLENIC-ACID |
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| BIGG ID | 48234 |
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| KNApSAcK ID | C00001226 |
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| HET ID | Not Available |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| Flavornet ID | Not Available |
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| GoodScent ID | Not Available |
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| SuperScent ID | Not Available |
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| Wikipedia ID | gamma-Linolenic acid |
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| Phenol-Explorer Metabolite ID | Not Available |
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| Duplicate IDS | Not Available |
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| Old DFC IDS | Not Available |
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| Associated Foods |
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| Food | Content Range | Average | Reference |
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| Food | | | Reference |
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| Biological Effects and Interactions |
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| Health Effects / Bioactivities | |
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| Enzymes | | Name | Gene Name | UniProt ID |
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| Bile acid-CoA:amino acid N-acyltransferase | BAAT | Q14032 | | Cytosolic acyl coenzyme A thioester hydrolase | ACOT7 | O00154 | | Acyl-coenzyme A thioesterase 2, mitochondrial | ACOT2 | P49753 | | Acyl-coenzyme A thioesterase 4 | ACOT4 | Q8N9L9 | | Acyl-coenzyme A thioesterase 8 | ACOT8 | O14734 | | Acyl-coenzyme A thioesterase 1 | ACOT1 | Q86TX2 |
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| Pathways | | Name | SMPDB Link | KEGG Link |
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| Alpha Linolenic Acid and Linoleic Acid Metabolism | SMP00018 | map00592 |
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| Metabolism | Not Available |
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| Biosynthesis | Not Available |
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| Organoleptic Properties |
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| Flavours | Not Available |
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| Files |
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| MSDS | show |
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| References |
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| Synthesis Reference | Not Available |
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| General Reference | Not Available |
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| 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).
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