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Merck

75100

Ethyl oleate

tested according to Ph. Eur.

Synonym(s):

Ethylis oleas, Oleic acid ethyl ester

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About This Item

Linear Formula:
CH3(CH2)7CH=CH(CH2)7COOC2H5
CAS Number:
111-62-6
Molecular Weight:
310.51
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
57652552
EC Number:
203-889-5
Beilstein/REAXYS Number:
1727318
MDL number:
MFCD00009579

Key Documents

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InChI key

LVGKNOAMLMIIKO-QXMHVHEDSA-N

InChI

1S/C20H38O2/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22-4-2/h11-12H,3-10,13-19H2,1-2H3/b12-11-

SMILES string

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

agency

tested according to Ph. Eur.

form

liquid

refractive index

n20/D 1.451 (lit.)

bp

216-218 °C/15 mmHg

mp

−32 °C (lit.)

density

0.87 g/mL at 25 °C (lit.)

functional group

ester

Quality Level

100

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Application

Ethyl oleate can be used as a reactant in the:
  • Bouveault−Blanc reduction to synthesize primary alcohols in the presence of stabilized alkali metals.
  • Lipase-catalyzed synthesis of ceramides by reacting with phytosphingosine.
  • Synthesis of amides via direct amidation with amines in the presence of transition metal catalyst.

Storage Class

10 - Combustible liquids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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Certificates of Analysis (COA)

Lot/Batch Number
BCCJ3507
BCCH5351
BCCG1854
BCCF1821
BCCD5870

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Chemical and thermochemical aspects of the ozonolysis of ethyl oleate: Decomposition enthalpy of ethyl oleate ozonide.
Cataldo F.
Chemistry and Physics of Lipids, 175, 41-49 (2013)
Michael D Hardy et al.
Proceedings of the National Academy of Sciences of the United States of America, 112(27), 8187-8192 (2015-06-24)
Cell membranes are dynamic structures found in all living organisms. There have been numerous constructs that model phospholipid membranes. However, unlike natural membranes, these biomimetic systems cannot sustain growth owing to an inability to replenish phospholipid-synthesizing catalysts. Here we report
Aihua Yu et al.
Journal of pharmaceutical sciences, 100(3), 933-941 (2010-09-24)
The main objective of the study was to investigate the efficacy of microemulsion (ME) to facilitate bioavailability of puerarin (PUE) after oral and nasal administration. The pseudo-ternary phase diagrams were constructed to screen the ME components and optimize the ME
K J Dussan et al.
Bioresource technology, 101(24), 9542-9549 (2010-08-19)
Magnetic nanoparticles were prepared by coprecipitating Fe(2+) and Fe(3+) ions in a sodium hydroxide solution and used as support for lipase. The lipase-coated particles were applied in a reactive extraction process that allowed separation of the products formed during transesterification.
Neil Loftus et al.
Journal of proteome research, 10(2), 705-713 (2010-10-30)
Alcoholism is a complex disorder that, in man, appears to be genetically influenced, although the underlying genes and molecular pathways are not completely known. Here, the intragastric alcohol feeding model in rodents was used together with high mass accuracy LC-MS(n)
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