Structure Database (LMSD)
Common Name
trans-vaccenic acid
Systematic Name
11E-octadecenoic acid
Synonyms
- trans-11-octadecenoic acid
- C18:1n-7
- Vaccensaure
3D model of trans-vaccenic acid
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
trans-Vaccenic acid is an ω-7 fatty acid that has been found in bovine milk fats.1 Dietary administration of trans-vaccenic acid (1% w/w) reduces total body fat, mesenteric fat, and adipocyte size, increases inguinal fat mass, and decreases intestinal and hepatic triglyceride secretion in a rat model of obesity with features of metabolic syndrome.2 It decreases hepatocellular ballooning and steatosis, markers of non-alcoholic fatty liver disease (NAFLD), in the same model. Dietary administration of a butter enriched with trans-vaccenic acid decreases serum cholesterol levels and the formation of aortic atherosclerotic lesions in Ldlr-/- mice.3
This information has been provided by Cayman Chemical
References
1. Jacome-Sosa, M.M., Borthwick, F., Mangat, R., et al. Diets enriched in trans-11 vaccenic acid alleviate ectopic lipid accumulation in a rat model of NAFLD and metabolic syndrome. J. Nutr. Biochem. 25(7), 692-701 (2014).
3. Santora, J.E., Palmquist, D.L., and Roehrig, K.L. Trans-vaccenic acid is desaturated to conjugated linoleic acid in mice. J. Nutr. 130(2), 208-215 (2000).
Reactions
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Reactions are shown if the E.C. number of the enzyme catalysing it is annotated in the UniProt database for a species belonging to the selected taxonomic class.
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References
String Representations
InChiKey (Click to copy)
UWHZIFQPPBDJPM-BQYQJAHWSA-N
InChi (Click to copy)
InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h7-8H,2-6,9-17H2,1H3,(H,19,20)/b8-7+
SMILES (Click to copy)
C(/C=C/CCCCCC)CCCCCCCCC(=O)O
Other Databases
Wikipedia
KEGG ID
HMDB ID
CHEBI ID
LIPIDBANK ID
DFA0116
PubChem CID
PlantFA ID
SwissLipids ID
Cayman ID
Calculated Physicochemical Properties
Heavy Atoms
20
Rings
0
Aromatic Rings
0
Rotatable Bonds
15
Van der Waals Molecular Volume
332.26
Topological Polar Surface Area
37.30
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
2
logP
6.11
Molar Refractivity
87.09
Admin
Created at
-
Updated at
16th Jan 2023