Docosadienoic acid

PUFA22:2Ω-6

  Overview

Stats

PUFA
Type
22
Carbons
2
Double bonds
1
Bis-allylic sites
336.6
Weight · g/mol
—
Melting point
C22H40O2
Formula

Also known as

IUPAC (13Z,16Z)-docosa-13,16-dienoic acid
Synonyms

  At a Glance

Source

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

Type

Very-long-chain polyunsaturated fatty acid with 22 carbons and two cis double bonds, an omega-6 fatty acid.

Identification

  Synonyms

Common Name Docosadienoic acid
IUPAC Name (13Z,16Z)-docosa-13,16-dienoic acid
Traditional Name —
Other Synonyms
  • (13Z,16Z)-docosadienoic acid

  External IDs

General References
Lipids
Lipid Maps LMFA01030405
Lipid Bank —
Swiss Lipids 000001120
PlantFA ID —
Food & Nutrition
FooDB —
INFOODS —
Chemistry / Compounds
PubChem CID 5312554
CAS 17735-98-7
ChEBI 75117
ChEMBL CHEMBL4240217
ChemSpider 4471979
InChIKey —
ZINC ID ZINC000030731054
NIKKAJI ID J1.720.804G
PDBe —
UCI (UniChem) —
SureChEMBL 842117
CCDC —
NMRShiftDB —
Metabolites & Pathways
HMDB HMDB0061714
METLIN —
RefMet ID —
RefMet Name —
MetaboLights ID MTBLS1071
BioCyc/MetaCyc —
MetaNetX ID MNXM9691
BiGG ID —
KEGG C16533
KNApSAcK —
Reactome ID —
Drugs & Pharmacology
DrugBank —
DrugCentral —
BindingDB 50463975
Guide to Pharm —
Probes & Drugs PD043825
Clinical & Medical
SNOMED-CT —
MeSH —
NCIt Code C68344
Regulatory
NIH UNII (USA) BT5EG9E9ZY
FDA SRS (USA) BT5EG9E9ZY
NHPID (Canada) —
DTXSID (USA) DTXSID201354088
TGA Ing ID (Australia) —
Commercial Suppliers
MolPort Molport-035-882-164
eMolecules —
Mcule —
ChemicalBook —
MedChemExpress —

Isomers of 22:2 (2)

Other fatty acids sharing the 22:2 notation — differing by double-bond position, geometry (cis/trans), or conjugation.

Name Geometry Trans Structure PubChem
Current Fatty Acid
Docosadienoic acid
(13Z,16Z)-docosa-13,16-dienoic acid
 13Z,16Z —
5312554
Category —
Conjugation Type Isolated
SMILES CCCCC\C=C/C\C=C/CCCCCCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Positional (1)
5Z,13Z-Docosadienoic Acid
(5Z,13Z)-docosa-5,13-dienoic acid
 5Z,13Z —
5282806
Category Non-Methylene-Interrupted Polyunsaturated Fatty Acid (Δ5)
Conjugation Type Isolated
SMILES CCCCCCCC\C=C/CCCCCC\C=C/CCCC(=O)O
Description A non-methylene-interrupted docosadienoic acid with widely spaced Δ5 and Δ13 double bonds, dominant in meadowfoam seed oil and used industrially for high-stability estolides and lubricants.
Origin Details
Origin Source Type Details
Meadowfoam Seed Oil Natural Comprises approximately 10-20% of meadowfoam (Limnanthes alba) seed oil; also present in minor amounts in some Cruciferae species.

Chemical Properties

Name(s):
Common Name Docosadienoic acid
Simple Notation 22:2
Notation 22:2(n-6)
IUPAC Name (13Z,16Z)-docosa-13,16-dienoic acid
Semi-systematic Docosadienoic acid
Structure:
Molecular C22H40O2
SMILES CCCCC\C=C/C\C=C/CCCCCCCCCCCC(=O)O
Cis / Trans cis
E-Z 13Z,16Z
Physical:
Weight 336.6 g/mol
Reactivity
Double Bonds 2
Bis-Allylic Carbons 1 (High Reactivity)
Beta-Oxidation
Beta Oxidation Cycles 10
ATP Yield (Net) 145 ATP