Erucic acid

MUFA22:1Ω-9

  Overview

Stats

MUFA
Type
22
Carbons
1
Double bonds
0
Bis-allylic sites
338.58
Weight · g/mol
33.6 °C
Melting point
C22H42O2
Formula

Also known as

IUPAC (Z)-docos-13-enoic acid
Synonyms

  At a Glance

Key Points

Prevalent in Brassica seeds — 20–54% of high-erucic rapeseed oil and ~42% of mustard oil.

Source

Primarily from plant oils.

Type

Very-long-chain monounsaturated fatty acid with 22 carbons and one cis double bond, an omega-9 fatty acid.

Identification

  Synonyms

Common Name Erucic acid
IUPAC Name (Z)-docos-13-enoic acid
Traditional Name —
Other Synonyms
  • (13Z)-Docosenoic acid
  • cis-13-Docosenoic acid

  External IDs

General References
Wikipedia Erucic_acid
Lipids
Lipid Maps LMFA01030089
Lipid Bank DFA0128
Swiss Lipids 000001118
PlantFA ID —
Food & Nutrition
FooDB FDB004287
INFOODS —
Chemistry / Compounds
PubChem CID 5281116
CAS 112-86-7
ChEBI 28792
ChEMBL CHEMBL1173380
ChemSpider 4444561
InChIKey —
ZINC ID ZINC000008220981
NIKKAJI ID J10.102H
PDBe 08O
UCI (UniChem) 602161
SureChEMBL 5987
CCDC ZZZDDJ
NMRShiftDB —
Metabolites & Pathways
HMDB HMDB0002068
METLIN 6470
RefMet ID —
RefMet Name —
MetaboLights ID MTBLS106
BioCyc/MetaCyc CPD-14292
MetaNetX ID MNXM11520
BiGG ID —
KEGG C08316
KNApSAcK C00001217
Reactome ID —
Drugs & Pharmacology
DrugBank —
DrugCentral —
BindingDB 50463967
Guide to Pharm —
Probes & Drugs PD020550
Clinical & Medical
SNOMED-CT —
MeSH C049811
NCIt Code C68364
Regulatory
NIH UNII (USA) 075441GMF2
FDA SRS (USA) 075441GMF2
NHPID (Canada) —
DTXSID (USA) DTXSID8026931
TGA Ing ID (Australia) —
Commercial Suppliers
MolPort Molport-003-933-468
eMolecules —
Mcule —
ChemicalBook —
MedChemExpress —

Isomers of 22:1 (3)

Other fatty acids sharing the 22:1 notation — differing by double-bond position, geometry (cis/trans), or conjugation.

Name Geometry Trans Structure PubChem
Current Fatty Acid
Erucic acid
(Z)-docos-13-enoic acid
 13Z —
5281116
Category —
Conjugation Type —
SMILES CCCCCCCC\C=C/CCCCCCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Geometric (1)
Brassidic acid
(E)-docos-13-enoic acid
 13E Trans
5282772
Category —
Conjugation Type —
SMILES CCCCCCCC\C=C\CCCCCCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Positional (1)
Cetoleic acid
(11Z)-docos-11-enoic acid
 11Z —
5282771
Category —
Conjugation Type —
SMILES CCCCCCCCCC\C=C/CCCCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.

Chemical Properties

Name(s):
Common Name Erucic acid
Simple Notation 22:1
Notation 22:1(n-9)
IUPAC Name (Z)-docos-13-enoic acid
Structure:
Molecular C22H42O2
Structure CH3(CH2)7CH=CH(CH2)11COOH
SMILES CCCCCCCC\C=C/CCCCCCCCCCCC(=O)O
Cis / Trans cis
E-Z 13Z
Physical:
Weight 338.58 g/mol
Melting Point 33.6 °C
Reactivity
Double Bonds 1
Bis-Allylic Carbons 0
Beta-Oxidation
Beta Oxidation Cycles 10
ATP Yield (Net) 146.5 ATP