Eicosadienoic acid

PUFA20:2Ω-6

  Overview

Stats

PUFA
Type
20
Carbons
2
Double bonds
1
Bis-allylic sites
308.5
Weight · g/mol
—
Melting point
C20H36O2
Formula

Also known as

IUPAC (11Z,14Z)-icosa-11,14-dienoic acid
Synonyms

  At a Glance

Key Points

A minor omega-6 fatty acid (20:2) involved in lipid metabolism.

Source

Found in meat. Also made by the body.

Type

Long-chain polyunsaturated fatty acid with 20 carbons and two cis double bonds, an omega-6 fatty acid.

Identification

  Synonyms

Common Name Eicosadienoic acid
IUPAC Name (11Z,14Z)-icosa-11,14-dienoic acid
Traditional Name —
Other Synonyms
  • 11,14-Eicosadienoic acid
  • 11,14-Icosadienoic acid
  • (11Z,14Z)-Eicosa-11,14-dienoic acid
  • (11Z,14Z)-eicosadienoic acid

  External IDs

General References
Lipids
Lipid Maps LMFA01031043
Lipid Bank —
Swiss Lipids 000001088
PlantFA ID —
Food & Nutrition
FooDB FDB012619
INFOODS —
Chemistry / Compounds
PubChem CID 6439848
CAS 5598-38-9
ChEBI 73731
ChEMBL CHEMBL464983
ChemSpider 4944228
InChIKey —
ZINC ID ZINC000008860490
NIKKAJI ID J394.182E
PDBe —
UCI (UniChem) 534238
SureChEMBL 416181
CCDC —
NMRShiftDB —
Metabolites & Pathways
HMDB HMDB0005060
METLIN —
RefMet ID —
RefMet Name —
MetaboLights ID MTBLS106
BioCyc/MetaCyc —
MetaNetX ID MNXM11473
BiGG ID —
KEGG C16525
KNApSAcK —
Reactome ID —
Drugs & Pharmacology
DrugBank —
DrugCentral —
BindingDB 50269533
Guide to Pharm —
Probes & Drugs PD020533
Clinical & Medical
SNOMED-CT —
MeSH —
NCIt Code —
Regulatory
NIH UNII (USA) —
FDA SRS (USA) —
NHPID (Canada) —
DTXSID (USA) DTXSID20912353
TGA Ing ID (Australia) —
Commercial Suppliers
MolPort Molport-009-018-857
eMolecules —
Mcule —
ChemicalBook —
MedChemExpress —

Isomers of 20:2 (5)

Other fatty acids sharing the 20:2 notation — differing by double-bond position, geometry (cis/trans), or conjugation.

Name Geometry Trans Structure PubChem
Current Fatty Acid
Eicosadienoic acid
(11Z,14Z)-icosa-11,14-dienoic acid
 11Z,14Z —
6439848
Category —
Conjugation Type Isolated
SMILES CCCCC\C=C/C\C=C/CCCCCCCCCC(O)=O
Description —
Origin Details

No origin information recorded.
Geometric (1)
11E,14E-Eicosadienoic Acid
(11E,14E)-icosa-11,14-dienoic acid
 11E,14E Trans
Category Isolated trans Omega-6 Polyunsaturated Fatty Acid
Conjugation Type Isolated
SMILES CCCCC/C=C/C/C=C/CCCCCCCCCC(=O)O
Description The all-trans geometric isomer of eicosadienoic acid (EDA), generated as an industrial byproduct of partial hydrogenation and present at trace levels in deodorized oils.
Origin Details
Origin Source Type Details
Industrial Hydrogenation Industrial Formed as a positional/geometric isomerization byproduct during partial hydrogenation and high-temperature deodorization of polyunsaturated oils.
Positional (3)
8Z,11Z-Eicosadienoic Acid
(8Z,11Z)-icosa-8,11-dienoic acid
 8Z,11Z —
5312528
Category Omega-9 Polyunsaturated Fatty Acid
Conjugation Type Isolated
SMILES CCCCCCCC\C=C/C\C=C/CCCCCCC(=O)O
Description A 20-carbon omega-9 polyunsaturated fatty acid generated by elongation and desaturation of oleic acid, present at low levels in mammalian lipids and elevated during essential fatty acid deficiency.
Origin Details
Origin Source Type Details
Endogenous Synthesis Natural Produced from oleic acid via successive Δ8 desaturation and ELOVL5-mediated elongation; serves as a precursor to Mead acid.
Keteleeronic Acid
(5Z,11Z)-icosa-5,11-dienoic acid
 5Z,11Z —
5312525
Category Non-Methylene-Interrupted Omega-9 Polyunsaturated Fatty Acid
Conjugation Type Isolated
SMILES CCCCCCCC\C=C/CCCC\C=C/CCCC(=O)O
Description A non-methylene-interrupted omega-9 polyunsaturated fatty acid with a characteristic Δ5 olefin, found in seed oils of Pinaceae (Keteleeria) and Cupressaceae gymnosperms.
Origin Details
Origin Source Type Details
Gymnosperm Seed Oils Natural Detected at up to ~2% in seed oils of Keteleeria (Pinaceae) and various Cupressaceae as a marker of Δ5-NMI desaturation.
Dihomotaxoleic Acid
(7Z,11Z)-icosa-7,11-dienoic acid
 7Z,11Z —
87944576
Category Non-Methylene-Interrupted Polyunsaturated Fatty Acid
Conjugation Type Isolated
SMILES CCCCCCCC\C=C/CC\C=C/CCCCCC(=O)O
Description A non-methylene-interrupted polyunsaturated fatty acid found in Taxus seed lipids, generated by elongation of taxoleic acid (5,9-18:2).
Origin Details
Origin Source Type Details
Taxus Seed Oils Natural Detected at ~0.1% in seed oils of Taxus species (Taxaceae) as an elongation product of taxoleic acid.

Chemical Properties

Name(s):
Common Name Eicosadienoic acid
Simple Notation 20:2
Notation 20:2(n-6)
IUPAC Name (11Z,14Z)-icosa-11,14-dienoic acid
Semi-systematic Eicosadienoic acid
Structure:
Molecular C20H36O2
SMILES CCCCC\C=C/C\C=C/CCCCCCCCCC(O)=O
Cis / Trans cis
E-Z 11Z,14Z
Physical:
Weight 308.5 g/mol
Reactivity
Double Bonds 2
Bis-Allylic Carbons 1 (High Reactivity)
Beta-Oxidation
Beta Oxidation Cycles 9
ATP Yield (Net) 131 ATP