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
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-
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
Title | Date | PubMed |
---|---|---|
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
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 02:10:51 UTC 2023
by
admin
on
Sat Dec 16 02:10:51 UTC 2023
|
Record UNII |
FC398RK06S
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Official Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
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 | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 |
|