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L1876

Sigma-Aldrich

Methyl linoleate

≥98% (GC)

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:
1727614
EC Number:
203-993-0
MDL number:
MFCD00009534
UNSPSC Code:
12352211
PubChem Substance ID:
24896293
NACRES:
NA.25

Quality Level

200

Assay

≥98% (GC)

form

liquid

refractive index

n20/D 1.462 (lit.)

bp

192 °C/4 mmHg (lit.)

mp

−35 °C (lit.)

density

0.889 g/mL at 25 °C (lit.)

functional group

ester

lipid type

omega FAs

shipped in

ambient

storage temp.

−20°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, 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 .

Biochem/physiol Actions

Methyl linoleate may be used as a model compound in oxidation/peroxidation assays to evaluate the anti-peroxidation activity of fullerenes, ellagitannins and other natural products.

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Marja Kähkönen et al.
Journal of agricultural and food chemistry, 60(5), 1167-1174 (2012-01-11)
Ellagitannins from red raspberries (Rubus idaeus) and cloudberries (Rubus chamaemorus) were isolated by using column chromatography and preparative HPLC. The berry phenolic isolates consisted of 80% (cloudberry) and of 60% (raspberry) of ellagitannins, with raspberries also containing anthocyanins. The main
Fanny Bery et al.
International journal of molecular sciences, 21(13) (2020-07-10)
Hypoxia is a well-established feature of prostate cancer (PCa) and is associated with disease aggressiveness. The hypoxic microenvironment initiates multiple adaptive responses including epithelial-to-mesenchymal transition (EMT) and a remodeling of calcium homeostasis involved in cancer progression. In the present study
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
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
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