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L1751

Sigma-Aldrich

Ethyl linoleate

≥99%

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Synonym(s):
Linoleic acid ethyl ester
Linear Formula:
CH3(CH2)3(CH2CH=CH)2(CH2)7COOC2H5
CAS Number:
544-35-4
Molecular Weight:
308.50
Beilstein:
1727827
EC Number:
208-868-4
MDL number:
MFCD00009535
PubChem Substance ID:
24896290
NACRES:
NA.25

biological source

plant oil (safflower)

Quality Level

200

Assay

≥99%

form

liquid

refractive index

n20/D 1.455 (lit.)

bp

224 °C/17 mmHg (lit.)

density

0.876 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)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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Biochem/physiol Actions

Ethyl linoleate may be used as a reference material in assays that quantify fatty acid ethyl esters (FAEEs) for detection of alcohol abuse. Linoleic acid ethyl ester (Ethyl linoleate) may be used and studied as an acetylcholinesterase (AChE) inhibitor.
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

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Abdulsallam Bakdash et al.
Analytical and bioanalytical chemistry, 396(7), 2469-2477 (2010-02-11)
Fatty acid ethyl esters (FAEE) and ethyl glucuronide (EtG) were determined in 602 meconium samples in a maternal health evaluation study for detection of gestational alcohol consumption. A validated headspace solid phase microextraction method in combination with GC-MS was used
Jonathan Kissling et al.
Phytotherapy research : PTR, 19(11), 984-987 (2005-12-01)
In a search for potential acetylcholinesterase (AChE) inhibitors, the ethanol extract of the bulbs of Crinum x powellii (Amaryllidaceae) was found to demonstrate a marked inhibition of this enzyme. Using a bio-guided isolation strategy, linoleic acid ethyl ester has been
Fritz Pragst et al.
Therapeutic drug monitoring, 30(2), 255-263 (2008-03-28)
The retrospective detection of alcohol consumption during pregnancy is an important part of the diagnosis of the fetal alcohol syndrome. A promising way to solve this problem can be the determination of fatty acid ethyl esters (FAEE) or/and ethyl glucuronide
Janine R Hutson et al.
Alcohol (Fayetteville, N.Y.), 45(2), 193-199 (2010-08-14)
Fatty acid ethyl esters (FAEEs) are nonoxidative metabolites of ethanol, and elevated levels of FAEE in meconium are a useful biomarker for heavy prenatal alcohol exposure. FAEE in meconium has been recommended as useful and cost-effective for universal screening for
Ho-Seok Kwak et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 878(21), 1871-1874 (2010-07-08)
This paper reports the development and validation of an improved assay for quantitation of fatty acid ethyl esters (FAEEs) in human meconium using liquid chromatography/tandem mass spectrometry (LC-MS/MS). FAAEs (ethyl laurate, ethyl myristate, ethyl palmitate, ethyl palmitoleate, ethyl stearate, ethyl
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