Stearidonic acidSDA

PUFA18:4Ω-3

  Overview

Stats

PUFA
Type
18
Carbons
4
Double bonds
3
Bis-allylic sites
276.4
Weight · g/mol
—
Melting point
C18H28O2
Formula

Also known as

IUPAC (6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoic acid

  At a Glance

Key Points

An omega-3 fatty acid, also called moroctic acid; a readily converted precursor toward EPA.

Source

Primarily from plants; also in fish & seafood.

Type

Long-chain polyunsaturated fatty acid with 18 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 Stearidonic acid
IUPAC Name (6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoic acid
Traditional Name —
Other Synonyms No other synonyms recorded.

  External IDs

General References
Lipids
Lipid Maps LMFA01030357
Lipid Bank —
Swiss Lipids 000001112
PlantFA ID —
Food & Nutrition
FooDB FDB004293
INFOODS —
Chemistry / Compounds
PubChem CID 5312508
CAS 20290-75-9
ChEBI 32389
ChEMBL CHEMBL484430
ChemSpider 4471933
InChIKey —
ZINC ID ZINC000013551720
NIKKAJI ID J381.480G
PDBe —
UCI (UniChem) 178700
SureChEMBL 29226
CCDC —
NMRShiftDB —
Metabolites & Pathways
HMDB HMDB0006547
METLIN —
RefMet ID —
RefMet Name —
MetaboLights ID MTBLS1107
BioCyc/MetaCyc CPD-12653
MetaNetX ID MNXM5608
BiGG ID 2218006
KEGG C16300
KNApSAcK C00000405
Reactome ID —
Drugs & Pharmacology
DrugBank —
DrugCentral —
BindingDB —
Guide to Pharm —
Probes & Drugs —
Clinical & Medical
SNOMED-CT —
MeSH C062895
NCIt Code —
Regulatory
NIH UNII (USA) P4CEK3495O
FDA SRS (USA) P4CEK3495O
NHPID (Canada) —
DTXSID (USA) DTXSID20920493
TGA Ing ID (Australia) —
Commercial Suppliers
MolPort Molport-009-018-856
eMolecules —
Mcule —
ChemicalBook —
MedChemExpress —

Isomers of 18:4 (4)

Other fatty acids sharing the 18:4 notation — differing by double-bond position, geometry (cis/trans), or conjugation.

Name Geometry Trans Structure PubChem
Current Fatty Acid
Stearidonic acid
(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoic acid
 6Z,9Z,12Z,15Z —
5312508
Category —
Conjugation Type Isolated
SMILES CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Positional (3)
alpha-Parinaric Acid
(9Z,11E,13E,15Z)-octadeca-9,11,13,15-tetraenoic acid
 9Z,11E,13E,15Z Trans
5281121
Category Conjugated Tetraenoic Fatty Acid (Fluorescent Probe)
Conjugation Type Conjugated
SMILES CC\C=C/C=C/C=C/C=C\CCCCCCCC(=O)O
Description A naturally fluorescent conjugated tetraene fatty acid isolated from the seeds of Parinari and Impatiens species, widely used as a membrane fluorescence probe for lipid phase studies.
Origin Details
Origin Source Type Details
Parinari Seed Oil Natural Isolated from seeds of Parinari laurinum (Makita tree, Fiji) and Impatiens balsamina, where the conjugated tetraene comprises a substantial fraction of seed lipids.
beta-Parinaric Acid
(9E,11E,13E,15E)-octadeca-9,11,13,15-tetraenoic acid
 9E,11E,13E,15E Trans
5282838
Category Conjugated Tetraenoic Fatty Acid (all-trans)
Conjugation Type Conjugated
SMILES CC/C=C/C=C/C=C/C=C/CCCCCCCC(=O)O
Description The all-trans isomerization product of alpha-parinaric acid, partitioning preferentially into solid-ordered membrane phases and used as a probe for liquid-ordered domains.
Origin Details
Origin Source Type Details
Isomerization of alpha-Parinaric Acid Industrial Generated by iodine- or photo-catalyzed isomerization of alpha-parinaric acid for use as a research-grade fluorescent probe.
Coniferonic Acid
(5Z,9Z,12Z,15Z)-octadeca-5,9,12,15-tetraenoic acid
 5Z,9Z,12Z,15Z —
13751481
Category Non-Methylene-Interrupted Omega-3 Polyunsaturated Fatty Acid
Conjugation Type Isolated
SMILES CC\C=C/C\C=C/C\C=C/CC\C=C/CCCC(=O)O
Description A non-methylene-interrupted omega-3 polyunsaturated fatty acid with a characteristic Δ5 olefin, found in needles of larch and other Pinaceae conifers as a marker of gymnosperm Δ5-desaturase activity.
Origin Details
Origin Source Type Details
Conifer Needles Natural Present in needle lipids of European larch (Larix decidua) and other Pinaceae conifers as the C18 product of gymnosperm Δ5-desaturase acting on alpha-linolenic acid.

Chemical Properties

Name(s):
Common Name Stearidonic acid
Abbreviation SDA
Simple Notation 18:4
Notation 18:4(n-3)
IUPAC Name (6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoic acid
Structure:
Molecular C18H28O2
SMILES CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)O
Cis / Trans cis
E-Z 6Z,9Z,12Z,15Z
Physical:
Weight 276.4 g/mol
Reactivity
Double Bonds 4
Bis-Allylic Carbons 3 (High Reactivity)
Beta-Oxidation
Beta Oxidation Cycles 8
ATP Yield (Net) 114 ATP