V0384

cis-Vaccenic acid

Name: <I>cis</I>-Vaccenic acid
Brand: SIGMA

≥97% (capillary GC), oil

Synonym(s):

cis-11-Octadecenoic acid

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About This Item

Linear Formula:

CH₃(CH₂)₅CH=CH(CH₂)₉CO₂H

CAS Number:

506-17-2

Molecular Weight:

282.46

UNSPSC Code:

12352211

NACRES:

NA.25

PubChem Substance ID:

24900694

MDL number:

MFCD00063187

Beilstein/REAXYS Number:

1726565

Key Documents

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InChI key

UWHZIFQPPBDJPM-FPLPWBNLSA-N

SMILES string

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

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-

biological source

Macadamia integrifolia oil

assay

≥97% (capillary GC)

form

oil

impurities

<0.5% Trans-11 isomer

refractive index

n20/D 1.459 (lit.)

bp

150 °C/0.03 mmHg (lit.)

mp

14-15 °C (lit.)

density

0.887 g/mL at 25 °C (lit.)

functional group

carboxylic acid

lipid type

unsaturated FAs

shipped in

ambient

storage temp.

−20°C

Quality Level

200

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Show Differences

1 of 4

This Item	P9417	V1131	E3635
Sigma-Aldrich V0384 cis-Vaccenic acid	Sigma-Aldrich P9417 Palmitoleic acid	Sigma-Aldrich V1131 trans-Vaccenic acid	Sigma-Aldrich E3635 cis-11-Eicosenoic acid
assay ≥97% (capillary GC)	assay ≥98.5% (GC)	assay ≥99% (capillary GC)	assay ≥99% (capillary GC)
biological source Macadamia integrifolia oil	biological source Macadamia integrifolia	biological source synthetic (organic)	biological source plant oil (Jojoba)
functional group carboxylic acid	functional group carboxylic acid, oleic acid	functional group carboxylic acid	functional group carboxylic acid
shipped in ambient	shipped in ambient	shipped in ambient	shipped in ambient
storage temp. −20°C	storage temp. −20°C	storage temp. −20°C	storage temp. −20°C
form oil	form liquid	form -	form liquid

Application

Enhancing durability and sustainable preservation of Egyptian stone monuments using metabolites produced by Streptomyces exfoliatus.: This research investigates the use of microbial metabolites, including cis-Vaccenic acid, to enhance the preservation of historical monuments (Abd-Elhalim et al., 2023). (Abd-Elhalim et al., 2023).

Packaging

Sealed ampule

Storage Class

10 - Combustible liquids

wgk

WGK 3

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number

0000512646

0000496609

0000479197

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Acute oral safety study of dairy fat rich in trans-10 C18:1 versus vaccenic plus conjugated linoleic acid in rats.

Arturo Anadón et al.

Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 48(2), 591-598 (2009-11-26)

The acute oral toxicity of a trans-10 C18:1-rich milk fat (T10, 20% of total FA), and a trans-11 C18:1+cis-9 trans-11 C18:2-rich milk fat (T11-CLA, 14% and 4.8% of total FA, respectively) was studied in rats receiving a single oral dose

Temperature adaptation in Lactobacillus fermentum: interconversions of oleic, vaccenic and dihydrosterulic acids.

M Suutari et al.

Journal of general microbiology, 138(3), 445-450 (1992-03-01)

The interchange of octadecenoic acids and dihydrosterulic acid was a response of aerobically growing Lactobacillus fermentum to changes in growth temperature. Oleic and vaccenic acid contents decreased both at temperatures below 20 degrees C and above 26 degrees C, showing

Jacaric acid and its octadecatrienoic acid geoisomers induce apoptosis selectively in cancerous human prostate cells: a mechanistic and 3-D structure-activity study.

Jihane Gasmi et al.

Phytomedicine : international journal of phytotherapy and phytopharmacology, 20(8-9), 734-742 (2013-03-05)

Plant-derived non-essential fatty acids are important dietary nutrients, and some are purported to have chemopreventive properties against various cancers, including that of the prostate. In this study, we determined the ability of seven dietary C-18 fatty acids to cause cytotoxicity

Effects of dietary cis 9, trans 11-18:2, trans 10, cis 12-18:2, or vaccenic acid (trans 11-18:1) during lactation on body composition, tissue fatty acid profiles, and litter growth in mice.

Juan J Loor et al.

The British journal of nutrition, 90(6), 1039-1048 (2003-12-04)

Cis 9, trans 11 (c 9, t11)-18:2 and trans 10, cis 12 (t10, c12)-18:2 are the major conjugated linoleic acid (CLA) isomers in dietary supplements which reduce milk fat content in nursing women. The present study evaluated the effects of

Fatty acid supplementation protects pulmonary artery endothelial cells from oxidant injury.

C M Hart et al.

American journal of respiratory cell and molecular biology, 3(5), 479-489 (1990-11-01)

Although supplemental fatty acids have been shown to alter the susceptibility of experimental animals to oxidant gases, the relationship between the degree of tissue fatty acyl unsaturation and resistance to oxidant exposure remains undefined. Because vascular endothelial cells have been

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