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 |
|---|---|---|
| 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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 21:09:48 GMT 2025
by
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on
Mon Mar 31 21:09:48 GMT 2025
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FC398RK06S
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Validated (UNII)
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DSLD |
3242 (Number of products:9)
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NCI_THESAURUS |
C68359
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DSLD |
4124 (Number of products:2)
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NCI_THESAURUS |
C2563
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| Code System | Code | Type | Description | ||
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DIHOMO-GAMMA-LINOLENIC ACID
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217-233-0
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53460
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1783-84-2
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53486
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FC398RK06S
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DTXSID00912351
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157667
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36036
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10359
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C68343
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300000038033
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DB00154
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5280581
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ACTIVE MOIETY |
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