Docosahexaenoic acidDHA

PUFA22:6Ω-3

  Overview

Stats

PUFA
Type
22
Carbons
6
Double bonds
5
Bis-allylic sites
328.5
Weight · g/mol
-44 °C
Melting point
C22H32O2
Formula

Also known as

IUPAC (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid
Traditional Cervonic acid

  At a Glance

Key Points

A major structural fat of the brain, cerebral cortex, skin and retina; supports neuronal membrane function and cognition.

Source

Conditionally essential. Primarily from fish & seafood. Also made by the body.

Type

Very-long-chain polyunsaturated fatty acid with 22 carbons and six cis double bonds, an omega-3 fatty acid. Its multiple bis-allylic sites make it prone to oxidation.

Identification

  Synonyms

Common Name Docosahexaenoic acid
IUPAC Name (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid
Traditional Name Cervonic acid
Other Synonyms No other synonyms recorded.

  External IDs

General References
Lipids
Lipid Maps LMFA01030185
Lipid Bank DFA0224
Swiss Lipids 000001084
PlantFA ID —
Food & Nutrition
FooDB FDB003003
INFOODS —
Chemistry / Compounds
PubChem CID 445580
CAS 6217-54-5
ChEBI 28125
ChEMBL CHEMBL367149
ChemSpider —
InChIKey —
ZINC ID ZINC000004474564
NIKKAJI ID J381.483A
PDBe HXA
UCI (UniChem) —
SureChEMBL 19577
CCDC —
NMRShiftDB —
Metabolites & Pathways
HMDB HMDB0002183
METLIN —
RefMet ID —
RefMet Name —
MetaboLights ID MTBLS106
BioCyc/MetaCyc CPD-10244
MetaNetX ID MNXM90206
BiGG ID —
KEGG C06429
KNApSAcK —
Reactome ID —
Drugs & Pharmacology
DrugBank DB03756
DrugCentral 4289
BindingDB 50210259
Guide to Pharm 1051
Probes & Drugs —
Clinical & Medical
SNOMED-CT —
MeSH C532150
NCIt Code C68346
Regulatory
NIH UNII (USA) ZAD9OKH9JC
FDA SRS (USA) ZAD9OKH9JC
NHPID (Canada) —
DTXSID (USA) DTXSID5040465
TGA Ing ID (Australia) —
Commercial Suppliers
MolPort Molport-003-932-890
eMolecules —
Mcule —
ChemicalBook —
MedChemExpress —

Isomers of 22:6 (2)

Other fatty acids sharing the 22:6 notation — differing by double-bond position, geometry (cis/trans), or conjugation.

Name Geometry Trans Structure PubChem
Current Fatty Acid
Docosahexaenoic acid
(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid
 4Z,7Z,10Z,13Z,16Z,19Z —
445580
Category —
Conjugation Type Isolated
SMILES CC\C=C/C\C=C/C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O
Description —
Origin Details

No origin information recorded.
Geometric (1)
all-trans-Docosahexaenoic Acid
(4E,7E,10E,13E,16E,19E)-docosa-4,7,10,13,16,19-hexaenoic acid
 4E,7E,10E,13E,16E,19E Trans
Category Isolated all-trans Omega-3 Very Long-Chain Polyunsaturated Fatty Acid
Conjugation Type Isolated
SMILES CC/C=C/C/C=C/C/C=C/C/C=C/C/C=C/C/C=C/CCC(=O)O
Description The all-trans geometric isomer of DHA, present as a trace processing artifact in deodorized and refined marine omega-3 oils.
Origin Details
Origin Source Type Details
Industrial Deodorization Industrial Formed at trace levels during high-temperature deodorization, refining, or thermal stress of DHA-rich marine oils through free-radical-mediated geometric isomerization across multiple double-bond positions.

Chemical Properties

Name(s):
Common Name Docosahexaenoic acid
Abbreviation DHA
Simple Notation 22:6
Notation 22:6(n-3)
IUPAC Name (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid
Traditional Name Cervonic acid
Semi-systematic Docosahexaenoic acid
Structure:
Molecular C22H32O2
SMILES CC\C=C/C\C=C/C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O
Cis / Trans cis
E-Z 4Z,7Z,10Z,13Z,16Z,19Z
Physical:
Weight 328.5 g/mol
Melting Point -44 °C
Reactivity
Double Bonds 6
Bis-Allylic Carbons 5 (High Reactivity)
Beta-Oxidation
Beta Oxidation Cycles 10
ATP Yield (Net) 139 ATP