Articles:
g-linolenic acid
Notes:
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) 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 |  3D/inchi
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| FDA UNII: | 78YC2MAX4O | |
| Nikkaji Web: | J12.229G | |
| Beilstein Number: | 1712253 | |
| MDL: | MFCD00065718 | |
| XlogP3-AA: | 5.90 (est) | |
| Molecular Weight: | 278.43550000 | |
| Formula: | C18 H30 O2 | |
| BioActivity Summary: | listing | |
| NMR Predictor: | Predict (works with chrome or firefox) | |
Category: natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
| Google Scholar: | Search |
| Google Books: | Search |
| Google Scholar: with word "volatile" | Search |
| Google Scholar: with word "flavor" | Search |
| Google Scholar: with word "odor" | Search |
| Google Patents: | Search |
| US Patents: | Search |
| EU Patents: | Search |
| Pubchem Patents: | Search |
| PubMed: | Search |
| NCBI: | Search |
| FDA/DG SANTE Petitions, Reviews, Notices: | |
| GRN 652 | Gamma linolenic acid safflower oil View - notice PDF |
Physical Properties:
| Assay: | 95.00 to 100.00 % |
| Food Chemicals Codex Listed: | No |
| Boiling Point: | 379.50 °C. @ 760.00 mm Hg (est) |
| Flash Point: | 530.00 °F. TCC ( 276.40 °C. ) (est) |
| logP (o/w): | 6.570 (est) |
| Soluble in: | |
| water, 0.02371 mg/L @ 25 °C (est) | |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). | |
Cosmetic Information:
| None found |
Suppliers:
| BOC Sciences |
| For experimental / research use only. |
| cis,cis,cis-6,9,12-Octadecatrienoic Acid 95% |
| Sigma-Aldrich |
| For experimental / research use only. |
| gamma-Linolenic acid
analytical standard |
| TCI AMERICA |
| For experimental / research use only. |
| gamma-Linolenic Acid >98.0%(GC)(T) |
Safety Information:
| Hazards identification | |
| Classification of the substance or mixture | |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) | |
| None found. | |
| GHS Label elements, including precautionary statements | |
| Pictogram | |
| Hazard statement(s) | |
| None found. | |
| Precautionary statement(s) | |
| None found. | |
| Oral/Parenteral Toxicity: | |
| Not determined | |
| Dermal Toxicity: | |
| Not determined | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in Use Information:
| Category: | natural substances and extractives | ||
| Recommendation for gamolenic acid usage levels up to: | |||
| not for fragrance use. | |||
| Recommendation for gamolenic acid flavor usage levels up to: | |||
| not for flavor use. | |||
Safety References:
| EPI System: | View |
| ClinicalTrials.gov: | search |
| Chemical Carcinogenesis Research Information System: | Search |
| AIDS Citations: | Search |
| Cancer Citations: | Search |
| Toxicology Citations: | Search |
| EPA GENetic TOXicology: | Search |
| EPA ACToR: | Toxicology Data |
| EPA Substance Registry Services (SRS): | Registry |
| Laboratory Chemical Safety Summary : | 5280933 |
| National Institute of Allergy and Infectious Diseases: | Data |
| WGK Germany: | 3 |
| (6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid | |
| Chemidplus: | 0000506263 |
References:
| (6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid | |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 5280933 |
| Pubchem (sid): | 134976478 |
Other Information:
| (IUPAC): | Atomic Weights of the Elements 2011 (pdf) |
| Videos: | The Periodic Table of Videos |
| tgsc: | Atomic Weights use for this web site |
| (IUPAC): | Periodic Table of the Elements |
| CHEBI: | View |
| CHEMBL: | View |
| Golm Metabolome Database: | Search |
| KEGG (GenomeNet): | C06426 |
| HMDB (The Human Metabolome Database): | HMDB03073 |
| FooDB: | FDB002943 |
| Export Tariff Code: | 2916.15.1000 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| Wikipedia: | View |
Potential Blenders and core components note
| None Found | ||
Potential Uses:
| None Found |
Occurrence (nature, food, other): note
| borage fruit oil Search Trop Picture | |
| borage leaf Search Trop Picture | |
| borage seed Search Trop Picture | |
| borage seed oil Search Trop Picture | |
| carrot seed Search Trop Picture | |
| currant black currant seed Search Trop Picture | |
| currant black currant seed oil Search Trop Picture | |
| evening-primrose seed Search Trop Picture | |
| evening-primrose seed oil Search Trop Picture | |
| flax seed Search Trop Picture | |
| gooseberry seed Search Trop Picture |
Synonyms:
| gamoleic acid | |
| g- | linolenic acid |
| gamma- | linolenic acid |
| (6Z,9Z,12Z)- | octadeca-6,9,12-trienoic acid |
| (6Z,9Z,12Z)- | octadecatrienoic acid |
| (Z,Z,Z)-6,9,12- | octadecatrienoic acid |
| 6-cis,9-cis,12-cis- | octadecatrienoic acid |
| 6,9,12-all-cis- | octadecatrienoic acid |
| 6(Z),9(Z),12(Z)- | octadecatrienoic acid |
| 6Z,9Z,12Z- | octadecatrienoic acid |
| cis-6,cis-9,cis-12- | octadecatrienoic acid |
| cis,cis,cis-6,9,12- | octadecatrienoic acid |
| 6,9,12- | octadecatrienoic acid, (6Z,9Z,12Z)- |
| 6,9,12- | octadecatrienoic acid, (Z,Z,Z)- |