| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2006-05-22 09:12:30 -0600 |
| Update Date |
2013-02-08 17:12:16 -0700 |
| HMDB ID |
HMDB03073 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
Gamma-Linolenic acid |
| Description |
Gamma-Linolenic acid is 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. |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- (6,9,12)-linolenate
- (6,9,12)-linolenic acid
- (6Z,9Z,12Z)-Octadecatrienoate
- (6Z,9Z,12Z)-Octadecatrienoic acid
- (Z,Z,Z)-6,9,12-Octadecatrienoate
- (Z,Z,Z)-6,9,12-Octadecatrienoic acid
- 6(Z),9(Z),12(Z)-Octadecatrienoate
- 6(Z),9(Z),12(Z)-Octadecatrienoic acid
- 6,9,12-All-cis-Octadecatrienoate
- 6,9,12-All-cis-Octadecatrienoic acid
- 6,9,12-Octadecatrienoate
- 6,9,12-Octadecatrienoic acid
- 6Z,9Z,12Z-Octadecatrienoate
- 6Z,9Z,12Z-Octadecatrienoic acid
- All-cis-6,9,12-octadecatrienoate
- All-cis-6,9,12-octadecatrienoic acid
- cis-delta(6,9,12)-Octadecatrienoate
- cis-delta(6,9,12)-Octadecatrienoic acid
- gamma-Linolenate
- gamma-Linolenic acid
- gamma-Llnolenic acid
- Ligla
|
| Chemical Formula |
C18H30O2 |
| Average Molecular Weight |
278.4296 |
| Monoisotopic Molecular Weight |
278.224580204 |
| IUPAC Name |
(6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid |
| Traditional IUPAC Name |
gamma-linolenic acid |
| CAS Registry Number |
506-26-3 |
| SMILES |
CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O |
| 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- |
| InChI Key |
VZCCETWTMQHEPK-QNEBEIHSSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Lipids |
| Class |
Lineolic Acids and Derivatives |
| Sub Class |
N/A |
| Other Descriptors |
- Aliphatic Acyclic Compounds
- Organic Compounds
- Straight Chain Fatty Acids
- Unsaturated Fatty Acids
|
| Substituents |
- Acyclic Alkene
- Carboxylic Acid
|
| Direct Parent |
Lineolic Acids and Derivatives |
| Ontology |
|---|
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
- Cell signaling
- Fuel and energy storage
- Fuel or energy source
- Membrane integrity/stability
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| Application |
- Nutrients
- Stabilizers
- Surfactants and Emulsifiers
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| Cellular locations |
- Cytoplasm
- Extracellular
- Membrane (predicted from logP)
|
| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
Not Available |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
Not Available |
Not Available |
| LogP |
Not Available |
Not Available |
|
| Predicted Properties |
|
| Spectra |
|---|
|
|
| Biological Properties |
|---|
| Cellular Locations |
- Cytoplasm
- Extracellular
- Membrane (predicted from logP)
|
| Biofluid Locations |
|
| Tissue Location |
- Epidermis
- Adipose Tissue
- Platelet
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| Pathways |
| Name |
SMPDB Link |
KEGG Link |
| Alpha Linolenic Acid and Linoleic Acid Metabolism |
SMP00018
|
map00592 
|
|
| Normal Concentrations |
|---|
|
| Blood |
Detected and Quantified |
|
1.08 +/- 1.5 uM |
Adult (>18 years old) |
Not Specified |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
0.310 +/- 0.196 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
1.03 +/- 0.005 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
|
| Abnormal Concentrations |
|---|
|
Not Available |
| Associated Disorders and Diseases |
|---|
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB002943 |
| KNApSAcK ID |
C00001226 |
| Chemspider ID |
4444436 |
| KEGG Compound ID |
C06426 |
| BioCyc ID |
5Z13E-15S-91115-TRIHYDROXYPROSTA- |
| BiGG ID |
48234 |
| Wikipedia Link |
gamma-Linolenic acid |
| NuGOwiki Link |
HMDB03073 |
| Metagene Link |
HMDB03073 |
| METLIN ID |
386 |
| PubChem Compound |
5280933 |
| PDB ID |
Not Available |
| ChEBI ID |
28661 |
| References |
|---|
| Synthesis Reference |
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. |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
|
| General References |
- Levy RJ, Lian JB: gamma-Carboxyglutamate excretion and warfarin therapy. Clin Pharmacol Ther. 1979 May;25(5 Pt 1):562-70.
Pubmed: 373941
- 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.
Pubmed: 9306089
- 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.
Pubmed: 9415022
- 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.
Pubmed: 10617998
- 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.
Pubmed: 9202801
- 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.
Pubmed: 11164299
- 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.
Pubmed: 2550526
- 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.
Pubmed: 8884146
- 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.
Pubmed: 11421921
- 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.
Pubmed: 14569405
- 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.
Pubmed: 12010583
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