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 | C18H29O2 |
| Molecular Weight | 277.4217 |
| Charge | -1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 3 |
| Optical Activity | NONE |
| 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 |
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 Gamolenic acid was used for the treatment of breast painand atopic dermatitis in Europe, although now the drug is withdrawn from the market (there is no safety issue associated with the withdrawal of the licences).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 |
|---|---|---|
| gamma-Carboxyglutamate excretion and warfarin therapy. | 1979 May |
|
| Is the origin of atopy linked to deficient conversion of omega-6-fatty acids to prostaglandin E1? | 1989 Sep |
|
| 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 |
|
| Evidence for direct binding of fatty acids and eicosanoids to human peroxisome proliferators-activated receptor alpha. | 1999 Jul 14 |
|
| Identification of the major intestinal fatty acid transport protein. | 1999 Sep |
|
| The influence of polyunsaturated fatty acids on probiotic growth and adhesion. | 2001 Jan 15 |
|
| Free fatty acids regulate gut incretin glucagon-like peptide-1 secretion through GPR120. | 2005 Jan |
|
| Induction of apoptosis in K562/ADM cells by gamma-linolenic acid involves lipid peroxidation and activation of caspase-3. | 2006 Aug 25 |
|
| 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 |
|
| Antimicrobial activity of n-6, n-7 and n-9 fatty acids and their esters for oral microorganisms. | 2010 Aug |
|
| Antineoplastic effects of gamma linolenic Acid on hepatocellular carcinoma cell lines. | 2010 Jul |
|
| JNK implication in adipocyte-like cell death induced by chemotherapeutic drug cisplatin. | 2015 Feb |
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
Sun Dec 18 06:47:20 UTC 2022
by
admin
on
Sun Dec 18 06:47:20 UTC 2022
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| Record UNII |
L4WFA9KRB5
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| Record Status |
Validated (UNII)
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| Record Version |
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23676161
Created by
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86761-55-9
Created by
admin on Sun Dec 18 06:47:20 UTC 2022 , Edited by admin on Sun Dec 18 06:47:20 UTC 2022
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L4WFA9KRB5
Created by
admin on Sun Dec 18 06:47:20 UTC 2022 , Edited by admin on Sun Dec 18 06:47:20 UTC 2022
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PRIMARY |
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PARENT -> SALT/SOLVATE |
