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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
Structure of SODIUM DIHOMO-.GAMMA.-LINOLENATE

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-;

HIDE SMILES / InChI

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

PubMed

TitleDatePubMed
Relationships between levels of essential fatty acids and zinc in plasma of cystic fibrosis patients.
1981 May
Is the origin of atopy linked to deficient conversion of omega-6-fatty acids to prostaglandin E1?
1989 Sep
Effects of safflower oil and evening primrose oil in men with a low dihomo-gamma-linolenic level.
1990 Apr
Influence of dietary arachidonic acid on metabolism in vivo of 8cis,11cis,14-eicosatrienoic acid in humans.
1997 Apr
Essential fatty acids in breast milk of atopic mothers: comparison with non-atopic mothers, and effect of borage oil supplementation.
2000 Mar
Metabolic consequences of hypoxia from birth and dexamethasone treatment in the neonatal rat: comprehensive hepatic lipid and fatty acid profiling.
2004 Nov
Free fatty acids regulate gut incretin glucagon-like peptide-1 secretion through GPR120.
2005 Jan
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

Patents

Substance Class Chemical
Created
by admin
on Sat Dec 16 12:48:57 GMT 2023
Edited
by admin
on Sat Dec 16 12:48:57 GMT 2023
Record UNII
DIY57A1X5I
Record Status Validated (UNII)
Record Version
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Name Type Language
SODIUM DIHOMO-.GAMMA.-LINOLENATE
Common Name English
SODIUM DIHOMO-GAMMA-LINOLENATE
Common Name English
DIHOMO-.GAMMA.-LINOLENIC ACID SODIUM SALT
Systematic Name English
8,11,14-EICOSATRIENOIC ACID, SODIUM SALT, (Z,Z,Z)-
Systematic Name English
DIHOMO-GAMMA-LINOLENIC ACID SODIUM SALT
Common Name English
Code System Code Type Description
CAS
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
PRIMARY
DRUG BANK
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
PRIMARY
FDA UNII
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
PRIMARY
PUBCHEM
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
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE