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Merck
CN

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:
Molecular Weight:
310.51
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
203-889-5
Beilstein/REAXYS Number:
1727318
MDL number:
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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

Quality Level

bp

216-218 °C/15 mmHg

mp

−32 °C (lit.)

density

0.87 g/mL at 25 °C (lit.)

functional group

ester

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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

Eyeshields, Gloves


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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
Brian T Bennett et al.
Oxidative medicine and cellular longevity, 2020, 3938672-3938672 (2020-08-11)
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Claudia Dussaubat et al.
Journal of chemical ecology, 36(5), 522-525 (2010-04-20)
Pheromones in social insects play a key role in the regulation of group homoeostasis. It is well-established that parasites can modify hormone signaling of their host, but less is known about the effect of parasites on pheromone signaling in insect
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

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