Details
Stereochemistry | ACHIRAL |
Molecular Formula | C20H33O2.Na |
Molecular Weight | 328.4646 |
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/CCCCCCC([O-])=O
InChI
InChIKey=SQGOEODKLMPIRQ-HPFCUAHCSA-M
InChI=1S/C20H34O2.Na/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22;/h6-7,9-10,12-13H,2-5,8,11,14-19H2,1H3,(H,21,22);/q;+1/p-1/b7-6-,10-9-,13-12-;
Molecular Formula | C20H33O2 |
Molecular Weight | 305.4748 |
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 |
Dihomo-gamma-linolenic acid (DGLA) is an n-6 polyunsaturated fatty acid that is mainly metabolized to an anti-inflammatory eicosanoid, prostaglandin (PG) E1, via the cyclooxygenase (COX) pathway. DGLA exists widely in the human body and daily animal-source foods. Concentrations of DGLA in the serum of atopic dermatitis patients are lower than those in healthy volunteers. DGLA suppressed clinical severity of skin lesions dose-dependently, with an increase in DGLA contents in phospholipids of skin, spleen, and plasma. Discontinuation of DGLA administration resulted in the onset of dermatitis and a decrease in DGLA contents in skin, spleen, and plasma. These findings indicate that oral administration of DGLA effectively prevents the development of atopic dermatitis in NC/Nga mice. DGLA may have an anti-atherosclerotic effect in apoE-deficient mice via PGE1 formation. As dihomo-γ-linolenic acid and arachidonic acid compete for processing by these oxidation enzymes, introduction of dihomo-γ-linolenic acid to platelets is correlated to suppression of arachidonic acid metabolites and promotion of dihomo-γ-linolenic acid metabolites such as PGE1, which produces an antithrombotic effect.
Approval Year
PubMed
Title | Date | PubMed |
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Relationships between levels of essential fatty acids and zinc in plasma of cystic fibrosis patients. | 1981 May |
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Is the origin of atopy linked to deficient conversion of omega-6-fatty acids to prostaglandin E1? | 1989 Sep |
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Effects of safflower oil and evening primrose oil in men with a low dihomo-gamma-linolenic level. | 1990 Apr |
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Influence of dietary arachidonic acid on metabolism in vivo of 8cis,11cis,14-eicosatrienoic acid in humans. | 1997 Apr |
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Essential fatty acids in breast milk of atopic mothers: comparison with non-atopic mothers, and effect of borage oil supplementation. | 2000 Mar |
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Metabolic consequences of hypoxia from birth and dexamethasone treatment in the neonatal rat: comprehensive hepatic lipid and fatty acid profiling. | 2004 Nov |
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Free fatty acids regulate gut incretin glucagon-like peptide-1 secretion through GPR120. | 2005 Jan |
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COX-2 inhibitors and metabolism of essential fatty acids. | 2005 Jul |
|
A biosynthetic pathway generating 12-hydroxy-5,8,14-eicosatrienoic acid from arachidonic acid is active in mouse skin microsomes. | 2006 Jan |
Patents
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 12:48:57 GMT 2023
by
admin
on
Sat Dec 16 12:48:57 GMT 2023
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Record UNII |
DIY57A1X5I
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Record Status |
Validated (UNII)
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Record Version |
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65881-87-0
Created by
admin on Sat Dec 16 12:48:57 GMT 2023 , Edited by admin on Sat Dec 16 12:48:57 GMT 2023
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DBSALT002649
Created by
admin on Sat Dec 16 12:48:57 GMT 2023 , Edited by admin on Sat Dec 16 12:48:57 GMT 2023
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DIY57A1X5I
Created by
admin on Sat Dec 16 12:48:57 GMT 2023 , Edited by admin on Sat Dec 16 12:48:57 GMT 2023
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23694180
Created by
admin on Sat Dec 16 12:48:57 GMT 2023 , Edited by admin on Sat Dec 16 12:48:57 GMT 2023
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Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE |
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