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Details

Stereochemistry ACHIRAL
Molecular Formula C20H34O2
Molecular Weight 306.4828
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 3
Charge 0

SHOW SMILES / InChI
Structure of DALEUTON

SMILES

CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(O)=O

InChI

InChIKey=HOBAELRKJCKHQD-QNEBEIHSSA-N
InChI=1S/C20H34O2/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)/b7-6-,10-9-,13-12-

HIDE SMILES / InChI

Molecular Formula C20H34O2
Molecular Weight 306.4828
Charge 0
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 Mon Mar 31 21:09:48 GMT 2025
Edited
by admin
on Mon Mar 31 21:09:48 GMT 2025
Record UNII
FC398RK06S
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIROLEUTON
INN  
Preferred Name English
DALEUTON
INN  
Official Name English
RO 12-1989
Code English
DS-107
Code English
DIHOMO-GAMMA-LINOLENIC ACID
Common Name English
daleuton [INN]
Common Name English
8,11,14-EICOSATRIENOIC ACID, (8Z,11Z,14Z)-
Common Name English
8,11,14-EICOSATRIENOIC ACID
Systematic Name English
20:3(N-6)
Common Name English
CIS-8,CIS-11,CIS-14-EICOSATRIENOIC ACID
Common Name English
DS107G
Code English
DIHOMO-.GAMMA.-LINOLENIC ACID
Common Name English
Diroleuton [WHO-DD]
Common Name English
DGLA
Common Name English
20:3 (.OMEGA.-6) FATTY ACID
Common Name English
.GAMMA.-HOMOLINOLENIC ACID
Common Name English
ALL-CIS-8,11,14-EICOSATRIENOIC ACID
Common Name English
8,11,14-ALL-CIS-EICOSATRIENOIC ACID
Common Name English
DS-107G
Code English
BISHOMO-.GAMMA.-LINOLENIC ACID
Common Name English
(Z,Z,Z)-8,11,14-EICOSATRIENOIC ACID
Systematic Name English
DS107
Code English
CIS-8,11,14-EICOSATRIENOIC ACID
Systematic Name English
8Z,11Z,14Z-EICOSATRIENOIC ACID
Common Name English
Classification Tree Code System Code
DSLD 3242 (Number of products:9)
Created by admin on Mon Mar 31 21:09:48 GMT 2025 , Edited by admin on Mon Mar 31 21:09:48 GMT 2025
NCI_THESAURUS C68359
Created by admin on Mon Mar 31 21:09:48 GMT 2025 , Edited by admin on Mon Mar 31 21:09:48 GMT 2025
DSLD 4124 (Number of products:2)
Created by admin on Mon Mar 31 21:09:48 GMT 2025 , Edited by admin on Mon Mar 31 21:09:48 GMT 2025
NCI_THESAURUS C2563
Created by admin on Mon Mar 31 21:09:48 GMT 2025 , Edited by admin on Mon Mar 31 21:09:48 GMT 2025
Code System Code Type Description
WIKIPEDIA
DIHOMO-GAMMA-LINOLENIC ACID
Created by admin on Mon Mar 31 21:09:48 GMT 2025 , Edited by admin on Mon Mar 31 21:09:48 GMT 2025
PRIMARY
ECHA (EC/EINECS)
217-233-0
Created by admin on Mon Mar 31 21:09:48 GMT 2025 , Edited by admin on Mon Mar 31 21:09:48 GMT 2025
PRIMARY
CHEBI
53460
Created by admin on Mon Mar 31 21:09:48 GMT 2025 , Edited by admin on Mon Mar 31 21:09:48 GMT 2025
PRIMARY
CAS
1783-84-2
Created by admin on Mon Mar 31 21:09:48 GMT 2025 , Edited by admin on Mon Mar 31 21:09:48 GMT 2025
PRIMARY
CHEBI
53486
Created by admin on Mon Mar 31 21:09:48 GMT 2025 , Edited by admin on Mon Mar 31 21:09:48 GMT 2025
PRIMARY
FDA UNII
FC398RK06S
Created by admin on Mon Mar 31 21:09:48 GMT 2025 , Edited by admin on Mon Mar 31 21:09:48 GMT 2025
PRIMARY
EPA CompTox
DTXSID00912351
Created by admin on Mon Mar 31 21:09:48 GMT 2025 , Edited by admin on Mon Mar 31 21:09:48 GMT 2025
PRIMARY
PUBCHEM
157667
Created by admin on Mon Mar 31 21:09:48 GMT 2025 , Edited by admin on Mon Mar 31 21:09:48 GMT 2025
PRIMARY
CHEBI
36036
Created by admin on Mon Mar 31 21:09:48 GMT 2025 , Edited by admin on Mon Mar 31 21:09:48 GMT 2025
PRIMARY
INN
10359
Created by admin on Mon Mar 31 21:09:48 GMT 2025 , Edited by admin on Mon Mar 31 21:09:48 GMT 2025
PRIMARY
NCI_THESAURUS
C68343
Created by admin on Mon Mar 31 21:09:48 GMT 2025 , Edited by admin on Mon Mar 31 21:09:48 GMT 2025
PRIMARY
SMS_ID
300000038033
Created by admin on Mon Mar 31 21:09:48 GMT 2025 , Edited by admin on Mon Mar 31 21:09:48 GMT 2025
PRIMARY
DRUG BANK
DB00154
Created by admin on Mon Mar 31 21:09:48 GMT 2025 , Edited by admin on Mon Mar 31 21:09:48 GMT 2025
PRIMARY
PUBCHEM
5280581
Created by admin on Mon Mar 31 21:09:48 GMT 2025 , Edited by admin on Mon Mar 31 21:09:48 GMT 2025
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY