Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C18H29O2.Na |
| Molecular Weight | 300.4114 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 3 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].CCCCC\C=C/C\C=C/C\C=C/CCCCC([O-])=O
InChI
InChIKey=MQLYJTAVSNRQGM-HPFCUAHCSA-M
InChI=1S/C18H30O2.Na/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);/q;+1/p-1/b7-6-,10-9-,13-12-;
| Molecular Formula | Na |
| Molecular Weight | 22.9898 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C18H29O2 |
| Molecular Weight | 277.4217 |
| Charge | -1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 3 |
| Optical Activity | NONE |
Gamolenic acid also known as gamma-lonolenic acid is a natural component of Oenothera biennis L. (Evening Primrose). Gamolenic acid was used for the treatment of breast painand atopic dermatitis in Europe, although now the drug is withdrawn from the market (there is no safety issue associated with the withdrawal of the licences). The mechanism of action of gamolenic acid is connected with its interaction with prostanoid pathway.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Evening primrose oil (Epogam) in the treatment of chronic hand dermatitis: disappointing therapeutic results. | 1996 |
|
| Plasma and tissue levels of lipids, fatty acids and plasma carnitine in neonates receiving a new fat emulsion. | 1997 Jun |
|
| Modulation in vitro of human natural cytotoxicity, lymphocyte proliferative response to mitogens and cytokine production by essential fatty acids. | 1997 Oct |
|
| Evidence for age-related differences in the fatty acid composition of human adipose tissue, independent of diet. | 1997 Sep |
|
| Eicosapentaenoic acid and docosahexaenoic acid from fish oils: differential associations with lipid responses. | 2002 May |
|
| Synergistic regulation of endothelial tight junctions by antioxidant (Se) and polyunsaturated lipid (GLA) via Claudin-5 modulation. | 2006 Aug 1 |
|
| Induction of apoptosis in K562/ADM cells by gamma-linolenic acid involves lipid peroxidation and activation of caspase-3. | 2006 Aug 25 |
|
| Conjugated linoleic acid, unlike other unsaturated fatty acids, strongly induces glutathione synthesis without any lipoperoxidation. | 2006 Nov |
|
| TRPV1 is a novel target for omega-3 polyunsaturated fatty acids. | 2007 Jan 15 |
|
| Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism. | 2008 Apr |
|
| Antineoplastic effects of gamma linolenic Acid on hepatocellular carcinoma cell lines. | 2010 Jul |
Sample Use Guides
4–6 capsules (500 mg) twice daily (40 mg gamolenic acid per capsule).
Route of Administration:
Oral
The cells were treated with various concentrations of gamolenic acid for 24 h and cell viability was determined by the MTT assay. Treatment of the K562 cells with gamolenic concentrations less
than 50 uM did not inhibit cell viability, but treatment
with concentrations of 50-150 uM caused a dosedependent decrease, and the concentration of gamolenic acid inducing 50% cell inhibition (IC50) after 24 h was 101.59 uM.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 11:06:00 UTC 2023
by
admin
on
Sat Dec 16 11:06:00 UTC 2023
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| Record UNII |
L4WFA9KRB5
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| Record Status |
Validated (UNII)
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86761-55-9
Created by
admin on Sat Dec 16 11:06:00 UTC 2023 , Edited by admin on Sat Dec 16 11:06:00 UTC 2023
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L4WFA9KRB5
Created by
admin on Sat Dec 16 11:06:00 UTC 2023 , Edited by admin on Sat Dec 16 11:06:00 UTC 2023
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| Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE |
