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Merck

62262

Ethyl linoleate

technical, ≥65% (GC)

Synonym(s):

Linoleic acid ethyl ester

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About This Item

Linear Formula:
CH3(CH2)3(CH2CH=CH)2(CH2)7COOC2H5
CAS Number:
544-35-4
Molecular Weight:
308.50
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
57651879
EC Number:
208-868-4
Beilstein/REAXYS Number:
1727827
MDL number:
MFCD00009535

Key Documents

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InChI key

FMMOOAYVCKXGMF-MURFETPASA-N

InChI

1S/C20H36O2/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22-4-2/h8-9,11-12H,3-7,10,13-19H2,1-2H3/b9-8-,12-11-

SMILES string

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

grade

technical

concentration

≥65% (GC)

refractive index

n20/D 1.455 (lit.), n20/D 1.455

bp

224 °C/17 mmHg (lit.)

density

0.876 g/mL at 25 °C (lit.)

functional group

ester

Quality Level

100

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General description

Ethyl linoleate can undergo auto-oxidation in the presence of the catalyst manganese(II)acetylacetonate.

Application

Ethyl linoleate can be used as a drying agent for alkyd paints. It can also form N2,3-ethenoguanine via reaction with deoxyguanosine.

Biochem/physiol Actions

Ethyl linoleate solated from Oxalis triangularis inhibits forskolin-induced melanogenesis and tyrosinase activity in mouse B16 melanoma cells . This anti-melanogenic effect is mediated by inhibiting cAMP production.

Storage Class

10 - Combustible liquids

wgk

WGK 1

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCP2364
BCCN2902
BCCH5003
BCCF5064
BCCC8530

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"4-Hydroxy-2-nonenal and ethyl linoleate form N 2, 3-ethenoguanine under peroxidizing conditions"
Ham.L J-A, et al.
Chemical Research in Toxicology, 1243-1250 (2000)
"Fast autoxidation of ethyl linoleate catalyzed by [Mn (acac) 3] and bipyridine: A possible drying catalyst for alkyd paints"
Gorkum VR, et al.
Inorganic Chemistry, 43(08), 2456-2458 (2004)
Yun Ding et al.
Current biology : CB, 29(7), 1089-1099 (2019-03-19)
It is unclear where in the nervous system evolutionary changes tend to occur. To localize the source of neural evolution that has generated divergent behaviors, we developed a new approach to label and functionally manipulate homologous neurons across Drosophila species.
Toshiya Masuda et al.
Journal of agricultural and food chemistry, 54(16), 6069-6074 (2006-08-03)
In our studies of the chain-breaking antioxidant mechanism of natural phenols in food components, ferulic acid, a phenolic acid widely distributed in edible plants, especially grain, was investigated. The radical oxidation reaction of a large amount of ethyl linoleate in
Dong-Woon Kim et al.
Circulation, 109(12), 1558-1563 (2004-03-10)
Paclitaxel has been shown to inhibit vascular smooth muscle cell migration and proliferation contributing to neointimal formation. This study tested whether novel oral formulations of paclitaxel can prevent neointimal formation in a rat carotid artery injury model. Oral formulations of
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