| Record Information |
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| Version | 2.0 |
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| Created at | 2024-09-09 20:43:35 UTC |
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| Updated at | 2024-09-09 20:43:35 UTC |
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| NP-MRD ID | NP0333828 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common 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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| Structure | [H]\C(CCCCC)=C(\[H])C\C([H])=C(\[H])C\C([H])=C(/[H])CCCCC(O)=O 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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| Synonyms | Not Available |
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| Chemical Formula | C18H30O2 |
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| Average Mass | 278.4360 Da |
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| Monoisotopic Mass | 278.22458 Da |
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| IUPAC Name | (6E,9Z,12E)-octadeca-6,9,12-trienoic acid |
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| Traditional Name | (6E,9Z,12E)-octadeca-6,9,12-trienoic acid |
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| CAS Registry Number | Not Available |
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| SMILES | [H]\C(CCCCC)=C(\[H])C\C([H])=C(\[H])C\C([H])=C(/[H])CCCCC(O)=O |
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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-FATBIOMTSA-N |
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| Experimental Spectra |
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| Not Available | | Predicted Spectra |
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| Not Available | | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | Not Available |
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| Chemical Taxonomy |
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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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| Physical Properties |
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| State | Not Available |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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