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Details

Stereochemistry ACHIRAL
Molecular Formula C18H34O2
Molecular Weight 282.4614
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of VACCENIC ACID

SMILES

CCCCCC\C=C\CCCCCCCCCC(O)=O

InChI

InChIKey=UWHZIFQPPBDJPM-BQYQJAHWSA-N
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+

HIDE SMILES / InChI
Vaccenic acid (VA) (t11 octadecenoic acid) is a positional and geometric isomer of oleic acid (c9-octadecenoic acid), and is the predominant trans monoene in ruminant fats (50%–80% of total trans content). Dietary VA can be desaturated to cis-9,trans-11 conjugated linoleic acid (c9,t11-CLA) in ruminants, rodents, and humans. Hydrogenated plant oils are another source of VA in the diet, and it has been recently estimated that this source may contribute to about 13%–17% of total VA intake. In contrast to suggestions from the epidemiological studies, the majority of studies using cancer cell lines (Awad et al. 1995; Miller et al. 2003) or rodent tumors (Banni et al. 2001; Corl et al. 2003; Ip et al. 1999; Sauer et al. 2004) have demonstrated that VA reduces cell growth and (or) tumor metabolism. Animal and in vitro studies suggest that the anti-cancer properties of VA are due, in part, to the in vivo conversion of VA to c9,t11-CLA. However, several additional mechanisms for the anti-cancer effects of VA have been proposed, including changes in phosphatidylinositol hydrolysis, reduced proliferation, increased apoptosis, and inhibition of fatty acid uptake. In conclusion, although the epidemiological evidence of VA intake and cancer risk suggests a positive relationship, this is not supported by the few animal studies that have been performed. The majority of the studies suggest that any health benefit of VA may be conferred by in vivo mammalian conversion of VA to c9,t11-CLA. VA acts as a partial agonist to both peroxisome proliferator-activated receptors (PPAR)-α and PPAR-γ in vitro, with similar affinity compared to commonly known PPAR agonists. Hypolipidemic and antihypertrophic bioactivity of VA is potentially mediated via PPAR-/-dependent pathways.

Approval Year

PubMed

PubMed

TitleDatePubMed
Human health benefits of vaccenic acid.
2009 Oct
The intestinal bioavailability of vaccenic acid and activation of peroxisome proliferator-activated receptor-α and -γ in a rodent model of dyslipidemia and the metabolic syndrome.
2012 Aug
Patents

Patents

Sample Use Guides

In a double-blind, randomized, parallel-intervention study, healthy young men who consumed a Vaccenic acid (VA)-rich diet (3.6 g VA/day) for 5 weeks had 6% lower total-cholesterol and 9% lower HDL-cholesterol concentrations than men consuming a low VA diet.
Route of Administration: Oral
Vaccenic acid (VA) at 30 and 100 uM concentrations suppressed cardiomyocyte hypertrophy in vitro in a PPAR-α- and PPAR-γ-dependent manner.
Name Type Language
VACCENIC ACID
MI   WHO-DD  
Systematic Name English
11-OCTADECENOIC ACID, (E)-
Common Name English
(E)-OCTADEC-11-ENOIC ACID
Systematic Name English
TRANS-VACCENIC ACID
Systematic Name English
18:1E(N-7)
Code English
11E-OCTADECENOIC ACID
Common Name English
Vaccenic acid [WHO-DD]
Common Name English
VACCENIC ACID [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C68440
Created by admin on Sat Dec 16 01:27:02 GMT 2023 , Edited by admin on Sat Dec 16 01:27:02 GMT 2023
NCI_THESAURUS C68404
Created by admin on Sat Dec 16 01:27:02 GMT 2023 , Edited by admin on Sat Dec 16 01:27:02 GMT 2023
DSLD 3244 (Number of products:8)
Created by admin on Sat Dec 16 01:27:02 GMT 2023 , Edited by admin on Sat Dec 16 01:27:02 GMT 2023
Code System Code Type Description
CHEBI
28727
Created by admin on Sat Dec 16 01:27:02 GMT 2023 , Edited by admin on Sat Dec 16 01:27:02 GMT 2023
PRIMARY
WIKIPEDIA
VACCENIC ACID
Created by admin on Sat Dec 16 01:27:02 GMT 2023 , Edited by admin on Sat Dec 16 01:27:02 GMT 2023
PRIMARY
CHEBI
50464
Created by admin on Sat Dec 16 01:27:02 GMT 2023 , Edited by admin on Sat Dec 16 01:27:02 GMT 2023
PRIMARY
CAS
693-72-1
Created by admin on Sat Dec 16 01:27:02 GMT 2023 , Edited by admin on Sat Dec 16 01:27:02 GMT 2023
PRIMARY
PUBCHEM
5281127
Created by admin on Sat Dec 16 01:27:02 GMT 2023 , Edited by admin on Sat Dec 16 01:27:02 GMT 2023
PRIMARY
NCI_THESAURUS
C68438
Created by admin on Sat Dec 16 01:27:02 GMT 2023 , Edited by admin on Sat Dec 16 01:27:02 GMT 2023
PRIMARY NCIT
EPA CompTox
DTXSID301009341
Created by admin on Sat Dec 16 01:27:02 GMT 2023 , Edited by admin on Sat Dec 16 01:27:02 GMT 2023
PRIMARY
FDA UNII
GQ72OGU4EV
Created by admin on Sat Dec 16 01:27:02 GMT 2023 , Edited by admin on Sat Dec 16 01:27:02 GMT 2023
PRIMARY
MERCK INDEX
m11354
Created by admin on Sat Dec 16 01:27:02 GMT 2023 , Edited by admin on Sat Dec 16 01:27:02 GMT 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
211-758-9
Created by admin on Sat Dec 16 01:27:02 GMT 2023 , Edited by admin on Sat Dec 16 01:27:02 GMT 2023
PRIMARY