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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
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
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 02:10:51 UTC 2023
Edited
by admin
on Sat Dec 16 02:10:51 UTC 2023
Record UNII
FC398RK06S
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DALEUTON
INN  
Official Name English
DIROLEUTON
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 Sat Dec 16 02:10:51 UTC 2023 , Edited by admin on Sat Dec 16 02:10:51 UTC 2023
NCI_THESAURUS C68359
Created by admin on Sat Dec 16 02:10:51 UTC 2023 , Edited by admin on Sat Dec 16 02:10:51 UTC 2023
DSLD 4124 (Number of products:2)
Created by admin on Sat Dec 16 02:10:51 UTC 2023 , Edited by admin on Sat Dec 16 02:10:51 UTC 2023
NCI_THESAURUS C2563
Created by admin on Sat Dec 16 02:10:51 UTC 2023 , Edited by admin on Sat Dec 16 02:10:51 UTC 2023
Code System Code Type Description
WIKIPEDIA
DIHOMO-GAMMA-LINOLENIC ACID
Created by admin on Sat Dec 16 02:10:51 UTC 2023 , Edited by admin on Sat Dec 16 02:10:51 UTC 2023
PRIMARY
ECHA (EC/EINECS)
217-233-0
Created by admin on Sat Dec 16 02:10:51 UTC 2023 , Edited by admin on Sat Dec 16 02:10:51 UTC 2023
PRIMARY
CHEBI
53460
Created by admin on Sat Dec 16 02:10:51 UTC 2023 , Edited by admin on Sat Dec 16 02:10:51 UTC 2023
PRIMARY
CAS
1783-84-2
Created by admin on Sat Dec 16 02:10:51 UTC 2023 , Edited by admin on Sat Dec 16 02:10:51 UTC 2023
PRIMARY
CHEBI
53486
Created by admin on Sat Dec 16 02:10:51 UTC 2023 , Edited by admin on Sat Dec 16 02:10:51 UTC 2023
PRIMARY
FDA UNII
FC398RK06S
Created by admin on Sat Dec 16 02:10:51 UTC 2023 , Edited by admin on Sat Dec 16 02:10:51 UTC 2023
PRIMARY
EPA CompTox
DTXSID00912351
Created by admin on Sat Dec 16 02:10:51 UTC 2023 , Edited by admin on Sat Dec 16 02:10:51 UTC 2023
PRIMARY
PUBCHEM
157667
Created by admin on Sat Dec 16 02:10:51 UTC 2023 , Edited by admin on Sat Dec 16 02:10:51 UTC 2023
PRIMARY
CHEBI
36036
Created by admin on Sat Dec 16 02:10:51 UTC 2023 , Edited by admin on Sat Dec 16 02:10:51 UTC 2023
PRIMARY
INN
10359
Created by admin on Sat Dec 16 02:10:51 UTC 2023 , Edited by admin on Sat Dec 16 02:10:51 UTC 2023
PRIMARY
NCI_THESAURUS
C68343
Created by admin on Sat Dec 16 02:10:51 UTC 2023 , Edited by admin on Sat Dec 16 02:10:51 UTC 2023
PRIMARY
SMS_ID
300000038033
Created by admin on Sat Dec 16 02:10:51 UTC 2023 , Edited by admin on Sat Dec 16 02:10:51 UTC 2023
PRIMARY
DRUG BANK
DB00154
Created by admin on Sat Dec 16 02:10:51 UTC 2023 , Edited by admin on Sat Dec 16 02:10:51 UTC 2023
PRIMARY
PUBCHEM
5280581
Created by admin on Sat Dec 16 02:10:51 UTC 2023 , Edited by admin on Sat Dec 16 02:10:51 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY