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cis-Vaccenic acid

analytical standard

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Synonym(s):
octadec-11(cis)-enoic acid, cis-11-Octadecenoic acid
Linear Formula:
CH3(CH2)5CH=CH(CH2)9CO2H
CAS Number:
506-17-2
Molecular Weight:
282.46
Beilstein:
1726565
MDL number:
MFCD00063187
UNSPSC Code:
41116107
NACRES:
NA.24

grade

analytical standard

Assay

≥97.0% (HPLC)

form

liquid

shelf life

limited shelf life, expiry date on the label

impurities

≤0.5% trans-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.)

application(s)

clinical testing

storage temp.

−20°C

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-

InChI key

UWHZIFQPPBDJPM-FPLPWBNLSA-N

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General description

cis-Vaccenic acid belongs to the class of unsaturated fatty acids. It is mostly reported to be produced by many species of heterotrophic bacteria. It also occurs in other marine organisms such as phytoplanktons. It also finds applications as a bacterial biomarker.

Application

cis-Vaccenic acid may be used as an analytical standard in the following:
  • Quantification of the analyte and its photodegradation products in marine samples using gas chromatography coupled to electron impact mass spectrometry (GC-EIMS). The photo-oxidation of the lipid components of the two strains of aerobic photoheterotrophic bacteria, Erythrobacter sp. strain NAP1 and Roseobacter-related isolate COL2P is studied and the results obtained after irradiation of axenic and nonaxenic cultures of the diatom, Skeletonema costatum is compared.
  • Quantification of the analyte in the methanolic extract of the leaves of Lepidium sativum using gas chromatography coupled to mass spectrometry (GC-MS).
  • Quantification of the analyte in methanolic extract of Rosmarinus oficinalis leaves using gas chromatography coupled to mass spectrometry and Fourier transform infrared spectroscopy.

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WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Regulatory Information

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Certificates of Analysis (COA)

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Gas chromatography mass spectrum and fourier-transform infrared spectroscopy analysis of methanolic extract of Rosmarinus oficinalis leaves
Hameed HI, et al.
Journal of pharmacognosy and phytotherapy, 7(6), 90-106 (2015)
Using Gas Chromatography-Mass Spectrometry (GC-MS) Technique for Analysis of Bioactive Compounds of Methanolic Leaves extract of Lepidium sativum
Hussein JH, et al.
Research Journal of Pharmacy and Technology, 10(11), 3981-3989 (2017)
Jean-François Rontani et al.
Lipids, 38(10), 1085-1092 (2003-12-13)
The origin of 11-hydroxyoctadec-trans-12-enoic and 12-hydroxyoctadec-trans-10-enoic acids (photodegradation products of cis-vaccenic acid) in the marine environment was investigated. cis-Vaccenic acid is commonly used as a bacterial biomarker; however, in heterotrophic bacteria the observed rates of cis-vaccenic acid photodegradation are negligible.

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