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Merck
CN

L1876

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

Key Documents

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Product Name

Methyl linoleate, ≥98% (GC)

InChI key

WTTJVINHCBCLGX-NQLNTKRDSA-N

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-

SMILES string

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

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

Quality Level

200

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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.

General description

Methyl linoleate, non-conjugated, is more easily oxidized than conjugated methyl linoleate .

Storage Class

10 - Combustible liquids

wgk

WGK 1

ppe

Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCP1127
BCCN1058
BCCL6803
BCCK5698
BCCJ5954

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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
Guo-Xiang Li et al.
European journal of medicinal chemistry, 45(5), 1821-1827 (2010-02-04)
5,7-, 5,8-, 6,8-, 7,8-dichloro-4-quinolinol-3-carboxylic acid (5,7-, 5,8-, 6,8-, 7,8-DCQA) together with 7-chloro-4-quinolinol-3-carboxylic acid (7-CQA) and 4-quinolinol-3-carboxylic acid (QA) were synthesized to investigate the antioxidant properties. 5,7-DCQA exhibited the highest ability to scavenge 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS+.), 2,2'-diphenyl-1-picrylhydrazyl (DPPH) and galvinoxyl
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