Structure Database (LMSD)

Common Name
trans-vaccenic acid
Systematic Name
11E-octadecenoic acid
Synonyms
  • trans-11-octadecenoic acid
  • C18:1n-7
  • Vaccensaure
LM ID
LMFA01030077
Formula
Exact Mass
Calculate m/z
282.25588
Sum Composition
Status
Curated




Classification

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 graph legend

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Bos taurus (#9913)
Mammalia (#40674)
Configuration of vaccenic acid.,
J Am Chem Soc, 1948
Pubmed ID: 18909181

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

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Created at
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Updated at
16th Jan 2023