U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 Na
Molecular Weight 22.98976928
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

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
A biosynthetic pathway generating 12-hydroxy-5,8,14-eicosatrienoic acid from arachidonic acid is active in mouse skin microsomes.
2006-01
COX-2 inhibitors and metabolism of essential fatty acids.
2005-07
Free fatty acids regulate gut incretin glucagon-like peptide-1 secretion through GPR120.
2005-01
Metabolic consequences of hypoxia from birth and dexamethasone treatment in the neonatal rat: comprehensive hepatic lipid and fatty acid profiling.
2004-11
Essential fatty acids in breast milk of atopic mothers: comparison with non-atopic mothers, and effect of borage oil supplementation.
2000-03
Influence of dietary arachidonic acid on metabolism in vivo of 8cis,11cis,14-eicosatrienoic acid in humans.
1997-04
Effects of safflower oil and evening primrose oil in men with a low dihomo-gamma-linolenic level.
1990-04
Is the origin of atopy linked to deficient conversion of omega-6-fatty acids to prostaglandin E1?
1989-09
Relationships between levels of essential fatty acids and zinc in plasma of cystic fibrosis patients.
1981-05
Patents

Patents

Substance Class Chemical
Created
by admin
on Tue Apr 01 19:49:18 GMT 2025
Edited
by admin
on Tue Apr 01 19:49:18 GMT 2025
Record UNII
DIY57A1X5I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SODIUM DIHOMO-.GAMMA.-LINOLENATE
Common Name English
DIHOMO-GAMMA-LINOLENIC ACID SODIUM SALT
Preferred 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
Code System Code Type Description
CAS
65881-87-0
Created by admin on Tue Apr 01 19:49:18 GMT 2025 , Edited by admin on Tue Apr 01 19:49:18 GMT 2025
PRIMARY
DRUG BANK
DBSALT002649
Created by admin on Tue Apr 01 19:49:18 GMT 2025 , Edited by admin on Tue Apr 01 19:49:18 GMT 2025
PRIMARY
FDA UNII
DIY57A1X5I
Created by admin on Tue Apr 01 19:49:18 GMT 2025 , Edited by admin on Tue Apr 01 19:49:18 GMT 2025
PRIMARY
PUBCHEM
23694180
Created by admin on Tue Apr 01 19:49:18 GMT 2025 , Edited by admin on Tue Apr 01 19:49:18 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE