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:
Molecular Weight:
294.47
UNSPSC Code:
12352211
NACRES:
NA.25
PubChem Substance ID:
EC Number:
203-993-0
Beilstein/REAXYS Number:
1727614
MDL number:
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
Quality Level
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
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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
10 - Combustible liquids
wgk
WGK 1
ppe
Eyeshields, Gloves
flash_point_f
338.0 °F - closed cup - (own results)
flash_point_c
170 °C - closed cup - (own results)
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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
Jian-Ying Feng et al.
European journal of medicinal chemistry, 46(4), 1198-1206 (2011-02-19)
In order to clarify the contribution of phenolic and enolic hydroxyl group to the antioxidant capacity of feruloylacetone, a model compound of half-curcumin, 6-(p-hydroxy-m-methoxyphenyl)-5-hexene-2,4-dione (FT), 6-(p-benzyloxy-m-methoxyphenyl)-5-hexene-2,4-dione (BMFT), 6-(m,p-dihydroxyphenyl)-5-hexene-2,4-dione (DDFT), 6-(p-hydroxy-m-methoxyphenyl)hexane-2,4-dione (DHFT), 6-(p-hydroxy-m-methoxyphenyl)-5-hexene-2,4-diol (THFT), and ethyl 2-(p-hydroxy-m-methoxybenzylidene)-3-oxobutanoate (EOFT) were synthesized. The
Roman Shchepin et al.
Journal of the American Chemical Society, 132(49), 17490-17500 (2010-11-26)
Free radical co-oxidation of polyunsaturated lipids with tyrosine or phenolic analogues of tyrosine gave rise to lipid peroxide-tyrosine (phenol) adducts in both aqueous micellar and organic solutions. The novel adducts were isolated and characterized by 1D and 2D NMR spectroscopy
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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