γ-Linolenic acidGLA

PUFA18:3Ω-6

  Overview

Stats

PUFA
Type
18
Carbons
3
Double bonds
2
Bis-allylic sites
278.4
Weight · g/mol
—
Melting point
C18H30O2
Formula

Also known as

IUPAC (6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid

  At a Glance

Key Points

An omega-6 fatty acid from seed oils (evening primrose, borage) that shifts eicosanoid output away from inflammatory leukotrienes.

Source

Primarily from plants; also in fungi.

Type

Long-chain polyunsaturated fatty acid with 18 carbons and three cis double bonds, an omega-6 fatty acid. Its multiple bis-allylic sites make it prone to oxidation.

Identification

  Synonyms

Ambiguity Note Linolenic acid can be misleading: alpha-Linolenic acid or gamma-Linolenic acid should be used.
Common Name γ-Linolenic acid
IUPAC Name (6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid
Traditional Name —
Other Synonyms No other synonyms recorded.

  External IDs

General References
Lipids
Lipid Maps LMFA01030141
Lipid Bank DFA0180
Swiss Lipids 000001103
PlantFA ID —
Food & Nutrition
FooDB FDB002943
INFOODS —
Chemistry / Compounds
PubChem CID 5280933
CAS 506-26-3
ChEBI 28661
ChEMBL CHEMBL464982
ChemSpider 4444436
InChIKey —
ZINC ID ZINC000003777423
NIKKAJI ID J12.229G
PDBe —
UCI (UniChem) 129753
SureChEMBL 19418
CCDC —
NMRShiftDB —
Metabolites & Pathways
HMDB HMDB0003073
METLIN 386
RefMet ID —
RefMet Name —
MetaboLights ID MTBLS106
BioCyc/MetaCyc CPD-8117
MetaNetX ID MNXM3995
BiGG ID 48234
KEGG C06426
KNApSAcK C00001226
Reactome ID —
Drugs & Pharmacology
DrugBank DB13854
DrugCentral 1276
BindingDB 50269532
Guide to Pharm 4710
Probes & Drugs PD014105
Clinical & Medical
SNOMED-CT —
MeSH D017965
NCIt Code C68369
Regulatory
NIH UNII (USA) 78YC2MAX4O
FDA SRS (USA) 78YC2MAX4O
NHPID (Canada) —
DTXSID (USA) DTXSID7046170
TGA Ing ID (Australia) —
Commercial Suppliers
MolPort Molport-003-937-818
eMolecules —
Mcule —
ChemicalBook —
MedChemExpress —

Isomers of 18:3 (11)

Other fatty acids sharing the 18:3 notation — differing by double-bond position, geometry (cis/trans), or conjugation.

Name Geometry Trans Structure PubChem
Current Fatty Acid
γ-Linolenic acid
(6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid
 6Z,9Z,12Z —
5280933
Category —
Conjugation Type Isolated
SMILES CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Positional (10)
α-Linolenic acid
(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid
 9Z,12Z,15Z —
5280934
Category —
Conjugation Type Isolated
SMILES CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O
Description —
Origin Details

No origin information recorded.
Pinolenic acid
(5Z,9Z,12Z)-octadeca-5,9,12-trienoic acid
 5Z,9Z,12Z —
5312495
Category —
Conjugation Type Isolated
SMILES CCCCC/C=C\C/C=C\CC\C=C/CCCC(=O)O
Description —
Origin Details

No origin information recorded.
Columbinic Acid
(5E,9Z,12Z)-octadeca-5,9,12-trienoic acid
 5E,9Z,12Z Trans
5312485
Category Non-Methylene-Interrupted Omega-6 Polyunsaturated Fatty Acid
Conjugation Type Isolated
SMILES CCCCC\C=C/C\C=C/CC/C=C/CCCC(=O)O
Description A non-methylene-interrupted Δ5-trans omega-6 polyunsaturated fatty acid found in Aquilegia (columbine) and Thalictrum seed oils, capable of reversing essential fatty-acid deficiency symptoms without serving as a prostaglandin precursor.
Origin Details
Origin Source Type Details
Ranunculaceae Seed Oils Natural Concentrated in seeds of Aquilegia vulgaris (columbine), Thalictrum, and related Ranunculaceae species.
Punicic acid
(9Z,11E,13Z)-octadeca-9,11,13-trienoic acid
 9Z,11E,13Z Trans
5281126
Category —
Conjugation Type Conjugated
SMILES CCCC/C=C\C=C\C=C/CCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
alpha-Eleostearic acid
(9Z,11E,13E)-octadeca-9,11,13-trienoic acid
 9Z,11E,13E Trans
5281115
Category —
Conjugation Type Conjugated
SMILES CCCC\C=C\C=C\C=C/CCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
beta-Eleostearic acid
(9E,11E,13E)-octadeca-9,11,13-trienoic acid
 9E,11E,13E Trans
5282820
Category —
Conjugation Type Conjugated
SMILES CCCC\C=C\C=C\C=C\CCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Catalpic acid
(9E,11E,13Z)-octadeca-9,11,13-trienoic acid
 9E,11E,13Z Trans
5385589
Category —
Conjugation Type Conjugated
SMILES CCCC/C=C\C=C\C=C\CCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Calendic acid
(8E,10E,12Z)-octadeca-8,10,12-trienoic acid
 8E,10E,12Z Trans
5282818
Category —
Conjugation Type Conjugated
SMILES CCCCC/C=C\C=C\C=C\CCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Jacaric Acid
(8Z,10E,12Z)-octadeca-8,10,12-trienoic acid
 8Z,10E,12Z Trans
5282817
Category Conjugated Linolenic Acid (CLnA, n-6)
Conjugation Type Conjugated
SMILES CCCCC\C=C/C=C/C=C\CCCCCCC(=O)O
Description A conjugated linolenic acid isomer found in Jacaranda mimosifolia seed oil, investigated for pro-apoptotic activity in leukemia cell lines.
Origin Details
Origin Source Type Details
Jacaranda Seed Oil Natural Comprises approximately 37% of seed oil fatty acids of Jacaranda mimosifolia (Bignoniaceae).
Rumelenic Acid
(9Z,11E,15Z)-octadeca-9,11,15-trienoic acid
 9Z,11E,15Z Trans
5280644
Category Ruminant Conjugated Linolenic Acid (CLnA, n-3)
Conjugation Type Conjugated
SMILES CC\C=C/CC/C=C/C=C\CCCCCCCC(=O)O
Description A partially conjugated omega-3 fatty acid (9,11-conjugated with isolated 15-DB) produced as a biohydrogenation intermediate of alpha-linolenic acid in ruminant rumen and present in dairy fat.
Origin Details
Origin Source Type Details
Rumen Biohydrogenation Natural Produced in cattle and sheep rumen by linoleate isomerase action on alpha-linolenic acid as an intermediate in microbial biohydrogenation to vaccenic and stearic acids.

Chemical Properties

Name(s):
Common Name γ-Linolenic acid
Abbreviation GLA
Simple Notation 18:3
Notation 18:3(n-6)
IUPAC Name (6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid
Structure:
Molecular C18H30O2
Structure CH3(CH2)4CH=CHCH2CH=CHCH2CH=CH(CH2)4COOH
SMILES CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O
Cis / Trans cis
E-Z 6Z,9Z,12Z
Physical:
Weight 278.4 g/mol
Reactivity
Double Bonds 3
Bis-Allylic Carbons 2 (High Reactivity)
Beta-Oxidation
Beta Oxidation Cycles 8
ATP Yield (Net) 115.5 ATP