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Methyl linoleate

analytical standard

Synonym(s):

Linoleic acid methyl ester, Methyl cis,cis-9,12-octadecadienoate

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About This Item

Linear Formula:
CH3(CH2)3(CH2CH=CH)2(CH2)7CO2CH3
CAS Number:
112-63-0
Molecular Weight:
294.47
Beilstein/REAXYS Number:
1727614
EC Number:
203-993-0
MDL number:
MFCD00009534
UNSPSC Code:
85151701
PubChem Substance ID:
329759724
NACRES:
NA.24

grade

analytical standard

Quality Level

100

assay

≥98.0% (GC)

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

refractive index

n20/D 1.462 (lit.)
n20/D 1.462

bp

192 °C/4 mmHg (lit.)

mp

−35 °C (lit.)

density

0.889 g/mL at 25 °C (lit.)

format

neat

functional group

ester

shipped in

ambient

storage temp.

2-8°C

SMILES string

CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC

InChI

1S/C19H34O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19(20)21-2/h7-8,10-11H,3-6,9,12-18H2,1-2H3/b8-7-,11-10-

InChI key

WTTJVINHCBCLGX-NQLNTKRDSA-N

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General description

Methyl linoleate is a methyl ester of the tri-unsaturated essential fatty acid, linoleic acid.
Methyl linoleate, non-conjugated, is more easily oxidized than conjugated methyl linoleate .

Application

The oxidation of methyl linoleate in organic solution and phosphatidylcholine (PC) in liposomal membranes induced by an azo initiator has often been used as a model for lipid peroxidation in vivo .
This analytical standard can also be used as follows:

  • Comparative analysis of gas chromatography-combustion-mass spectrometry and gas chromatography-flame ionization detector methods for the determination of fatty acid methyl esters (FAMEs) in biodiesel samples
  • Gas chromatography-tandem differential mobility spectrometry (DMS) based separation and quantification of 16 methyl- and ethyl- fatty acid esters from biodiesel samples
  • Simultaneous determination of fatty acid methyl esters in commercial food oil samples by gas chromatography-vacuum ultraviolet (GC-VUV) spectroscopy
  • Measurement of fatty acid methyl ester composition of various edible oil samples by 1H nuclear magnetic resonance (1H NMR) spectroscopy combined with partial least squares (PLS) method
  • Analysis of coffee oil and residue obtained from roasted coffee beans to determine the composition of 11 fatty acids following their methyl esterification by gas chromatography coupled with a flame ionization detector (GC-FID)
  • Simultaneous determination of fatty acids in bovine colostrum samples by GC-FID after their derivatization to ester forms using an acidic catalyst boron trifluoride

Other Notes

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Storage Class

10 - Combustible liquids

wgk_germany

WGK 1

ppe

Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG9356
BCCD7810
BCCB2987
BCBW6730
BCBW0371

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Philip T Lynett et al.
Organic & biomolecular chemistry, 9(9), 3320-3330 (2011-03-30)
It has long been recognized that garlic and petiveria, two plants of the Allium genus--which also includes onions, leeks and shallots--possess great medicinal value. In recent times, the biological activities of extracts of these plants have been ascribed to the
Yuewei Zhao et al.
Toxicology letters, 205(3), 302-309 (2011-07-05)
Pyrrolizidine alkaloid (PA)-containing plants are widespread in the world and are probably the most common poisonous plants affecting livestock, wildlife, and human. PAs require metabolic activation to generate pyrrolic metabolites (dehydro-PAs) that bind cellular protein and DNA, leading to hepatotoxicity
Yasutaka Shimotori et al.
Carbohydrate research, 359, 11-17 (2012-08-29)
Various glycosyl ferulates were efficiently synthesized from 2,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (TAGB) with amine by amine-promoted glycosylation without using heavy metal. The resulted acetylated glycosyl ferulates with acetoxyl groups at C-2, C-3 and C-4 were regioselectively deacetylated at C-4 and C-6 positions
Vitaly Roginsky
Chemistry and physics of lipids, 163(2), 127-130 (2009-11-03)
The kinetics of the chain free-radical oxidation of cardiolipin (CL), a unique phospholipid containing four linoleate moieties, have been studied for the first time. The technique based on monitoring oxygen consumption by using a Clark electrode was applied to determine
Huong T Pham et al.
Journal of the American Society for Mass Spectrometry, 24(2), 286-296 (2013-01-08)
Ozone-induced dissociation (OzID) is an alternative ion activation method that relies on the gas phase ion-molecule reaction between a mass-selected target ion and ozone in an ion trap mass spectrometer. Herein, we evaluated the performance of OzID for both the
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