cis-Vaccenic acid

MUFA18:1Ω-7

  Overview

Stats

MUFA
Type
18
Carbons
1
Double bonds
0
Bis-allylic sites
282.5
Weight · g/mol
—
Melting point
C18H34O2
Formula

Also known as

IUPAC (11Z)-octadec-11-enoic acid
Traditional Asclepic acid

  At a Glance

Source

Found in dairy and plant oils. Also made by the body.

Type

Long-chain monounsaturated fatty acid with 18 carbons and one cis double bond, an omega-7 fatty acid.

Identification

  Synonyms

Common Name cis-Vaccenic acid
IUPAC Name (11Z)-octadec-11-enoic acid
Traditional Name Asclepic acid
Other Synonyms No other synonyms recorded.

  External IDs

General References
Wikipedia —
Lipids
Lipid Maps LMFA01030076
Lipid Bank DFA0115
Swiss Lipids 000001202
PlantFA ID —
Food & Nutrition
FooDB FDB002952
INFOODS —
Chemistry / Compounds
PubChem CID 5282761
CAS 506-17-2
ChEBI 50464
ChEMBL CHEMBL1236642
ChemSpider —
InChIKey —
ZINC ID ZINC000014881303
NIKKAJI ID J367.010D
PDBe 4IF
UCI (UniChem) —
SureChEMBL 97463
CCDC —
NMRShiftDB —
Metabolites & Pathways
HMDB HMDB0303834
METLIN —
RefMet ID —
RefMet Name —
MetaboLights ID MTBLS1693
BioCyc/MetaCyc —
MetaNetX ID MNXM11120
BiGG ID —
KEGG C21944
KNApSAcK —
Reactome ID —
Drugs & Pharmacology
DrugBank DB04801
DrugCentral —
BindingDB —
Guide to Pharm —
Probes & Drugs PD006379
Clinical & Medical
SNOMED-CT —
MeSH —
NCIt Code —
Regulatory
NIH UNII (USA) 400K7322UW
FDA SRS (USA) 400K7322UW
NHPID (Canada) —
DTXSID (USA) DTXSID70881242
TGA Ing ID (Australia) —
Commercial Suppliers
MolPort Molport-003-959-881
eMolecules —
Mcule —
ChemicalBook —
MedChemExpress —

Isomers of 18:1 (6)

Other fatty acids sharing the 18:1 notation — differing by double-bond position, geometry (cis/trans), or conjugation.

Name Geometry Trans Structure PubChem
Current Fatty Acid
cis-Vaccenic acid
(11Z)-octadec-11-enoic acid
 11Z —
5282761
Category —
Conjugation Type —
SMILES CCCCCC\C=C/CCCCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Geometric (1)
trans-Vaccenic acid
(E)-octadec-11-enoic acid
 11E Trans
5281127
Category —
Conjugation Type —
SMILES CCCCCC\C=C\CCCCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Positional (4)
Oleic acid
(Z)-octadec-9-enoic acid
 9Z —
445639
Category —
Conjugation Type —
SMILES CCCCCCCC\C=C/CCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Petroselinic acid
(6Z)-octadec-6-enoic acid
 6Z —
5281125
Category —
Conjugation Type —
SMILES CCCCCCCCCCC/C=C\CCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Elaidic acid
(E)-octadec-9-enoic acid
 9E Trans
637517
Category —
Conjugation Type —
SMILES CCCCCCCC\C=C\CCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Isooleic acid
(E)-octadec-10-enoic acid
 10E —
5282760
Category —
Conjugation Type —
SMILES CCCCCCC/C=C/CCCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.

Chemical Properties

Name(s):
Common Name cis-Vaccenic acid
Simple Notation 18:1
Notation 18:1(n-7)
IUPAC Name (11Z)-octadec-11-enoic acid
Traditional Name Asclepic acid
Structure:
Molecular C18H34O2
SMILES CCCCCC\C=C/CCCCCCCCCC(=O)O
Cis / Trans cis
E-Z 11Z
Physical:
Weight 282.5 g/mol
Reactivity
Double Bonds 1
Bis-Allylic Carbons 0
Beta-Oxidation
Beta Oxidation Cycles 8
ATP Yield (Net) 118.5 ATP