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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
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
COX-2 inhibitors and metabolism of essential fatty acids.
2005 Jul
Patents

Patents

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 GMT 2023 , Edited by admin on Sat Dec 16 02:10:51 GMT 2023
NCI_THESAURUS C68359
Created by admin on Sat Dec 16 02:10:51 GMT 2023 , Edited by admin on Sat Dec 16 02:10:51 GMT 2023
DSLD 4124 (Number of products:2)
Created by admin on Sat Dec 16 02:10:51 GMT 2023 , Edited by admin on Sat Dec 16 02:10:51 GMT 2023
NCI_THESAURUS C2563
Created by admin on Sat Dec 16 02:10:51 GMT 2023 , Edited by admin on Sat Dec 16 02:10:51 GMT 2023
Code System Code Type Description
WIKIPEDIA
DIHOMO-GAMMA-LINOLENIC ACID
Created by admin on Sat Dec 16 02:10:51 GMT 2023 , Edited by admin on Sat Dec 16 02:10:51 GMT 2023
PRIMARY
ECHA (EC/EINECS)
217-233-0
Created by admin on Sat Dec 16 02:10:51 GMT 2023 , Edited by admin on Sat Dec 16 02:10:51 GMT 2023
PRIMARY
CHEBI
53460
Created by admin on Sat Dec 16 02:10:51 GMT 2023 , Edited by admin on Sat Dec 16 02:10:51 GMT 2023
PRIMARY
CAS
1783-84-2
Created by admin on Sat Dec 16 02:10:51 GMT 2023 , Edited by admin on Sat Dec 16 02:10:51 GMT 2023
PRIMARY
CHEBI
53486
Created by admin on Sat Dec 16 02:10:51 GMT 2023 , Edited by admin on Sat Dec 16 02:10:51 GMT 2023
PRIMARY
FDA UNII
FC398RK06S
Created by admin on Sat Dec 16 02:10:51 GMT 2023 , Edited by admin on Sat Dec 16 02:10:51 GMT 2023
PRIMARY
EPA CompTox
DTXSID00912351
Created by admin on Sat Dec 16 02:10:51 GMT 2023 , Edited by admin on Sat Dec 16 02:10:51 GMT 2023
PRIMARY
PUBCHEM
157667
Created by admin on Sat Dec 16 02:10:51 GMT 2023 , Edited by admin on Sat Dec 16 02:10:51 GMT 2023
PRIMARY
CHEBI
36036
Created by admin on Sat Dec 16 02:10:51 GMT 2023 , Edited by admin on Sat Dec 16 02:10:51 GMT 2023
PRIMARY
INN
10359
Created by admin on Sat Dec 16 02:10:51 GMT 2023 , Edited by admin on Sat Dec 16 02:10:51 GMT 2023
PRIMARY
NCI_THESAURUS
C68343
Created by admin on Sat Dec 16 02:10:51 GMT 2023 , Edited by admin on Sat Dec 16 02:10:51 GMT 2023
PRIMARY
SMS_ID
300000038033
Created by admin on Sat Dec 16 02:10:51 GMT 2023 , Edited by admin on Sat Dec 16 02:10:51 GMT 2023
PRIMARY
DRUG BANK
DB00154
Created by admin on Sat Dec 16 02:10:51 GMT 2023 , Edited by admin on Sat Dec 16 02:10:51 GMT 2023
PRIMARY
PUBCHEM
5280581
Created by admin on Sat Dec 16 02:10:51 GMT 2023 , Edited by admin on Sat Dec 16 02:10:51 GMT 2023
PRIMARY