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Sigma-Aldrich

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:
Molecular Weight:
308.50
Beilstein:
1727827
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

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.)

SMILES string

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

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-

InChI key

FMMOOAYVCKXGMF-MURFETPASA-N

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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 Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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"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)
"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)
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.
H Hara et al.
The Journal of nutrition, 126(4), 800-806 (1996-04-01)
Oxidized ethyl linoleate (OEL) was prepared by aeration at low temperature. Peroxide value (POV, mEq/kg lipid) of OEL was 1400; the major oxidized compounds were 9-hydroperoxy-cis, trans- and 13-hydroperoxy-trans, cis-octadecadienoate. Rats fed fiber-free or sugar-beet fiber (SBF, 100g/kg diet) diets
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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