α-Linolenic acidALA

PUFA18:3Ω-3 Essential

  Overview

Stats

PUFA
Type
18
Carbons
3
Double bonds
2
Bis-allylic sites
278.4
Weight · g/mol
-16.5 °C
Melting point
C18H30O2
Formula

Also known as

IUPAC (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid

  At a Glance

Source

Essential — must be obtained from the diet. Primarily from plant oils and plants.

Type

Long-chain polyunsaturated fatty acid with 18 carbons and three cis double bonds, an omega-3 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 α-Linolenic acid
IUPAC Name (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid
Traditional Name —
Other Synonyms No other synonyms recorded.

  External IDs

General References
Lipids
Lipid Maps LMFA01030152
Lipid Bank DFA0191
Swiss Lipids 000001101
PlantFA ID —
Food & Nutrition
FooDB FDB012462
INFOODS —
Chemistry / Compounds
PubChem CID 5280934
CAS 463-40-1
ChEBI 27432
ChEMBL CHEMBL8739
ChemSpider 4444437
InChIKey —
ZINC ID ZINC000003802189
NIKKAJI ID J5.773H
PDBe LNL
UCI (UniChem) 416221
SureChEMBL 15282
CCDC —
NMRShiftDB —
Metabolites & Pathways
HMDB HMDB0001388
METLIN 6208
RefMet ID —
RefMet Name —
MetaboLights ID MTBLS1051
BioCyc/MetaCyc LINOLENIC_ACID
MetaNetX ID MNXM794
BiGG ID 48237
KEGG C06427
KNApSAcK C00007247
Reactome ID —
Drugs & Pharmacology
DrugBank DB00132
DrugCentral 4618
BindingDB 50240347
Guide to Pharm 1049
Probes & Drugs PD010226
Clinical & Medical
SNOMED-CT —
MeSH D017962
NCIt Code C997
Regulatory
NIH UNII (USA) 0RBV727H71
FDA SRS (USA) 0RBV727H71
NHPID (Canada) —
DTXSID (USA) DTXSID7025506
TGA Ing ID (Australia) —
Commercial Suppliers
MolPort Molport-003-937-817
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
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.
Positional (10)
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.
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 α-Linolenic acid
Abbreviation ALA
Simple Notation 18:3
Notation 18:3(n-3)
IUPAC Name (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid
Structure:
Molecular C18H30O2
SMILES CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O
Cis / Trans cis
E-Z 9Z,12Z,15Z
Physical:
Weight 278.4 g/mol
Melting Point -16.5 °C
Reactivity
Double Bonds 3
Bis-Allylic Carbons 2 (High Reactivity)
Beta-Oxidation
Beta Oxidation Cycles 8
ATP Yield (Net) 115 ATP