Dihomo-γ-linolenic acidDGLA

PUFA20:3Ω-6

  Overview

Stats

PUFA
Type
20
Carbons
3
Double bonds
2
Bis-allylic sites
306.49
Weight · g/mol
—
Melting point
C20H34O2
Formula

Also known as

IUPAC (8Z,11Z,14Z)-icosa-8,11,14-trienoic acid
Synonyms

  At a Glance

Key Points

The elongation product of GLA; an uncommon fat (traces in animal products) and a precursor of anti-inflammatory eicosanoids.

Source

Found in meat. Also made by the body.

Type

Long-chain polyunsaturated fatty acid with 20 carbons and three cis double bonds, an omega-6 fatty acid. Its multiple bis-allylic sites make it prone to oxidation.

Identification

  Synonyms

Common Name Dihomo-γ-linolenic acid
IUPAC Name (8Z,11Z,14Z)-icosa-8,11,14-trienoic acid
Traditional Name —
Other Synonyms
  • 8, 11, 14-eicosatrienoic acid
  • C20:3n-6,9,12
  • gamma-Homolinolenic acid

  External IDs

General References
Lipids
Lipid Maps LMFA01030158
Lipid Bank DFA0197
Swiss Lipids 000000928
PlantFA ID —
Food & Nutrition
FooDB —
INFOODS —
Chemistry / Compounds
PubChem CID 5280581
CAS 1783-84-2
ChEBI 53486
ChEMBL CHEMBL465183
ChemSpider —
InChIKey —
ZINC ID ZINC000004521470
NIKKAJI ID J110.768B
PDBe LAX
UCI (UniChem) 179577
SureChEMBL 842729
CCDC —
NMRShiftDB 60020851
Metabolites & Pathways
HMDB HMDB0002925
METLIN —
RefMet ID —
RefMet Name —
MetaboLights ID MTBLS106
BioCyc/MetaCyc —
MetaNetX ID MNXM5607
BiGG ID —
KEGG C03242
KNApSAcK —
Reactome ID —
Drugs & Pharmacology
DrugBank DB00154
DrugCentral —
BindingDB 50269534
Guide to Pharm 9775
Probes & Drugs PD010198
Clinical & Medical
SNOMED-CT —
MeSH —
NCIt Code C68343
Regulatory
NIH UNII (USA) FC398RK06S
FDA SRS (USA) FC398RK06S
NHPID (Canada) —
DTXSID (USA) DTXSID00912351
TGA Ing ID (Australia) —
Commercial Suppliers
MolPort Molport-003-933-184
eMolecules 509170
Mcule —
ChemicalBook CB4667988
MedChemExpress HY-A0143

Isomers of 20:3 (6)

Other fatty acids sharing the 20:3 notation — differing by double-bond position, geometry (cis/trans), or conjugation.

Name Geometry Trans Structure PubChem
Current Fatty Acid
Dihomo-γ-linolenic acid
(8Z,11Z,14Z)-icosa-8,11,14-trienoic acid
 8Z,11Z,14Z —
5280581
Category —
Conjugation Type Isolated
SMILES CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Positional (5)
Eicosatrienoic acid
(11Z,14Z,17Z)-icosa-11,14,17-trienoic acid
 11Z,14Z,17Z —
5312529
Category —
Conjugation Type Isolated
SMILES CC/C=C\C/C=C\C/C=C\CCCCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Mead acid
(5Z,8Z,11Z)-icosa-5,8,11-trienoic acid
 5Z,8Z,11Z —
5312531
Category —
Conjugation Type Isolated
SMILES CCCCCCCC\C=C/C\C=C/C\C=C/CCCC(=O)O
Description —
Origin Details

No origin information recorded.
Sciadonic acid
(5Z,11Z,14Z)-icosa-5,11,14-trienoic acid
 5Z,11Z,14Z —
445084
Category —
Conjugation Type Isolated
SMILES CCCCC/C=C\C/C=C\CCCC\C=C/CCCC(=O)O
Description —
Origin Details

No origin information recorded.
5Z,8Z,14Z-Eicosatrienoic Acid
(5Z,8Z,14Z)-icosa-5,8,14-trienoic acid
 5Z,8Z,14Z —
6439516
Category Non-Methylene-Interrupted Polyunsaturated Fatty Acid
Conjugation Type Isolated
SMILES CCCCC\C=C/CCCC\C=C/C\C=C/CCCC(=O)O
Description A non-methylene-interrupted polyunsaturated fatty acid found in gymnosperm seed oils, generated by elongation of pinolenic acid and co-occurring with sciadonic acid.
Origin Details
Origin Source Type Details
Pinaceae Seed Oils Natural Detected in seed oils of Pinaceae as the C20 elongation product of pinolenic acid (5,9,12-18:3).
Dihomopinolenic Acid
(7Z,11Z,14Z)-icosa-7,11,14-trienoic acid
 7Z,11Z,14Z —
5312533
Category Non-Methylene-Interrupted Omega-6 Polyunsaturated Fatty Acid
Conjugation Type Isolated
SMILES CCCCC\C=C/C\C=C/CC\C=C/CCCCCC(=O)O
Description A non-methylene-interrupted omega-6 polyunsaturated fatty acid found in Taxaceae seed lipids as the C20 elongation/desaturation product of taxoleic acid.
Origin Details
Origin Source Type Details
Taxus Seed Oils Natural Present in seed oils of Taxus species, generated by chain elongation and Δ14 desaturation from taxoleic acid (5,9-18:2).

Chemical Properties

Name(s):
Common Name Dihomo-γ-linolenic acid
Abbreviation DGLA
Simple Notation 20:3
Notation 20:3(n-6)
IUPAC Name (8Z,11Z,14Z)-icosa-8,11,14-trienoic acid
Structure:
Molecular C20H34O2
SMILES CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)O
Cis / Trans cis
E-Z 8Z,11Z,14Z
Physical:
Weight 306.49 g/mol
Reactivity
Double Bonds 3
Bis-Allylic Carbons 2 (High Reactivity)
Beta-Oxidation
Beta Oxidation Cycles 9
ATP Yield (Net) 129.5 ATP