trans-Vaccenic acid

MUFA18:1Ω-7 Trans

  Overview

Stats

MUFA
Type
18
Carbons
1
Double bonds
0
Bis-allylic sites
282.5
Weight · g/mol
44 °C
Melting point
C18H34O2
Formula

Also known as

IUPAC (E)-octadec-11-enoic acid
Synonyms

  At a Glance

Key Points

The main natural trans fat in human milk and dairy; discovered in 1928 and a precursor of CLA.

Source

Primarily from dairy; also in ruminant fat.

Type

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

Identification

  Synonyms

Common Name trans-Vaccenic acid
IUPAC Name (E)-octadec-11-enoic acid
Traditional Name —
Other Synonyms
  • trans-octadec-11-enoic acid
  • 11(E)-vaccenic acid
  • C18:1 trans-11
  • 18:1 trans-11
  • Vaccenic acid
  • octadec-11(E)-enoic acid
  • trans-11-Octadecensaeure
  • (E)-11-octadecenoic acid
  • TVA
  • (11E)-Octadecenoic acid
  • trans-11-Octadecenoic acid

  External IDs

General References
Wikipedia Vaccenic_acid
Lipids
Lipid Maps LMFA01030077
Lipid Bank DFA0116
Swiss Lipids 000001203
PlantFA ID —
Food & Nutrition
FooDB FDB002952
INFOODS —
Chemistry / Compounds
PubChem CID 5281127
CAS 693-72-1
ChEBI 28727
ChEMBL —
ChemSpider 4444571
InChIKey —
ZINC ID ZINC000008221053
NIKKAJI ID J327.304K, J6.936A
PDBe —
UCI (UniChem) 652965
SureChEMBL 38907
CCDC —
NMRShiftDB —
Metabolites & Pathways
HMDB HMDB0003231
METLIN 3407
RefMet ID —
RefMet Name —
MetaboLights ID MTBLS1115
BioCyc/MetaCyc —
MetaNetX ID MNXM683743
BiGG ID 2217962
KEGG C08367
KNApSAcK C00001240
Reactome ID —
Drugs & Pharmacology
DrugBank —
DrugCentral —
BindingDB —
Guide to Pharm —
Probes & Drugs PD018590
Clinical & Medical
SNOMED-CT —
MeSH —
NCIt Code C68438
Regulatory
NIH UNII (USA) GQ72OGU4EV
FDA SRS (USA) GQ72OGU4EV
NHPID (Canada) —
DTXSID (USA) DTXSID301009341
TGA Ing ID (Australia) —
Commercial Suppliers
MolPort Molport-006-112-294
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
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.
Geometric (1)
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.
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 trans-Vaccenic acid
Simple Notation 18:1
Notation 18:1(n-7)
IUPAC Name (E)-octadec-11-enoic acid
Structure:
Molecular C18H34O2
Structure CH3(CH2)5CH=CH(CH2)9COOH
SMILES CCCCCC\C=C\CCCCCCCCCC(=O)O
Cis / Trans trans
E-Z 11E
Physical:
Weight 282.5 g/mol
Melting Point 44 °C
Reactivity
Double Bonds 1
Bis-Allylic Carbons 0
Beta-Oxidation
Beta Oxidation Cycles 8
ATP Yield (Net) 118.5 ATP