Eicosatetraenoic acidETA

PUFA20:4Ω-3

  Overview

Stats

PUFA
Type
20
Carbons
4
Double bonds
3
Bis-allylic sites
304.5
Weight · g/mol
—
Melting point
C20H32O2
Formula

Also known as

IUPAC (8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoic acid
Synonyms

  At a Glance

Key Points

An omega-3 fatty acid, an intermediate between stearidonic acid and EPA.

Source

Found in fish & seafood. Also made by the body.

Type

Long-chain polyunsaturated fatty acid with 20 carbons and four cis double bonds, an omega-3 fatty acid. Its multiple bis-allylic sites make it prone to oxidation.

Identification

  Synonyms

Common Name Eicosatetraenoic acid
IUPAC Name (8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoic acid
Traditional Name —
Other Synonyms
  • (8Z,11Z,14Z,17Z)-eicosa-8,11,14,17-tetraenoic acid

  External IDs

General References
Lipids
Lipid Maps LMFA01030818
Lipid Bank —
Swiss Lipids —
PlantFA ID —
Food & Nutrition
FooDB FDB022887
INFOODS —
Chemistry / Compounds
PubChem CID 11722594
CAS 24880-40-8
ChEBI 71488
ChEMBL —
ChemSpider 9897310
InChIKey —
ZINC ID ZINC000027644415
NIKKAJI ID J381.481E
PDBe —
UCI (UniChem) 22714315
SureChEMBL 453536
CCDC —
NMRShiftDB —
Metabolites & Pathways
HMDB HMDB0002177
METLIN —
RefMet ID —
RefMet Name —
MetaboLights ID MTBLS1411
BioCyc/MetaCyc CPD-8121
MetaNetX ID —
BiGG ID —
KEGG —
KNApSAcK —
Reactome ID —
Drugs & Pharmacology
DrugBank —
DrugCentral —
BindingDB —
Guide to Pharm —
Probes & Drugs PD020623
Clinical & Medical
SNOMED-CT —
MeSH —
NCIt Code —
Regulatory
NIH UNII (USA) 2K2DJ01BB7
FDA SRS (USA) 2K2DJ01BB7
NHPID (Canada) —
DTXSID (USA) DTXSID00920517
TGA Ing ID (Australia) —
Commercial Suppliers
MolPort Molport-009-018-829
eMolecules —
Mcule —
ChemicalBook —
MedChemExpress —

Isomers of 20:4 (3)

Other fatty acids sharing the 20:4 notation — differing by double-bond position, geometry (cis/trans), or conjugation.

Name Geometry Trans Structure PubChem
Current Fatty Acid
Eicosatetraenoic acid
(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoic acid
 8Z,11Z,14Z,17Z —
11722594
Category —
Conjugation Type Isolated
SMILES CC/C=C\C/C=C\C/C=C\C/C=C\CCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Positional (2)
Arachidonic acid
(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid
 5Z,8Z,11Z,14Z —
444899
Category —
Conjugation Type Isolated
SMILES CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O
Description —
Origin Details

No origin information recorded.
Juniperonic Acid
(5Z,11Z,14Z,17Z)-icosa-5,11,14,17-tetraenoic acid
 5Z,11Z,14Z,17Z —
5312543
Category Non-Methylene-Interrupted Omega-3 Polyunsaturated Fatty Acid
Conjugation Type Isolated
SMILES CC\C=C/C\C=C/C\C=C/CCCC\C=C/CCCC(=O)O
Description A non-methylene-interrupted omega-3 polyunsaturated fatty acid with a characteristic Δ5 olefin, found in gymnosperm seeds and investigated for anti-proliferative and eicosanoid-modulating activity.
Origin Details
Origin Source Type Details
Gymnosperm Seeds Natural Present in seeds of Juniperus, Podocarpus, Ginkgo, and Taxus species as the C20 product of gymnosperm Δ5-desaturase acting on eicosatrienoic intermediates.

Chemical Properties

Name(s):
Common Name Eicosatetraenoic acid
Abbreviation ETA
Simple Notation 20:4
Notation 20:4(n-3)
IUPAC Name (8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoic acid
Semi-systematic Eicosatetraenoic acid
Structure:
Molecular C20H32O2
SMILES CC/C=C\C/C=C\C/C=C\C/C=C\CCCCCCC(=O)O
Cis / Trans cis
E-Z 8Z,11Z,14Z,17Z
Physical:
Weight 304.5 g/mol
Reactivity
Double Bonds 4
Bis-Allylic Carbons 3 (High Reactivity)
Beta-Oxidation
Beta Oxidation Cycles 9
ATP Yield (Net) 128 ATP