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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, CIS-

SMILES

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

InChI

InChIKey=UWHZIFQPPBDJPM-FPLPWBNLSA-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

Molecular Formula C18H34O2
Molecular Weight 282.4614
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

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
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:37:10 GMT 2023
Edited
by admin
on Fri Dec 15 18:37:10 GMT 2023
Record UNII
400K7322UW
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VACCENIC ACID, CIS-
Common Name English
ASCLEPIC ACID
Common Name English
CIS-VACCENIC ACID (C18:1) (CONSTITUENT OF KRILL OIL) [DSC]
Common Name English
11Z-OCTADECENOIC ACID
Common Name English
11-OCTADECENOIC ACID, (Z)-
Systematic Name English
CIS-.DELTA.11-OCTADECENOIC ACID
Common Name English
11-OCTADECENOIC ACID, CIS-
Common Name English
18:1Z(N-7)
Code English
Code System Code Type Description
CAS
506-17-2
Created by admin on Fri Dec 15 18:37:10 GMT 2023 , Edited by admin on Fri Dec 15 18:37:10 GMT 2023
PRIMARY
PUBCHEM
5282761
Created by admin on Fri Dec 15 18:37:10 GMT 2023 , Edited by admin on Fri Dec 15 18:37:10 GMT 2023
PRIMARY
DRUG BANK
DB04801
Created by admin on Fri Dec 15 18:37:10 GMT 2023 , Edited by admin on Fri Dec 15 18:37:10 GMT 2023
PRIMARY
EPA CompTox
DTXSID70881242
Created by admin on Fri Dec 15 18:37:10 GMT 2023 , Edited by admin on Fri Dec 15 18:37:10 GMT 2023
PRIMARY
CHEBI
50464
Created by admin on Fri Dec 15 18:37:10 GMT 2023 , Edited by admin on Fri Dec 15 18:37:10 GMT 2023
PRIMARY
FDA UNII
400K7322UW
Created by admin on Fri Dec 15 18:37:10 GMT 2023 , Edited by admin on Fri Dec 15 18:37:10 GMT 2023
PRIMARY
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