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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:
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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Product Name

Ethyl oleate, tested according to Ph. Eur.

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

Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM2981
BCCK8413
BCCJ3507
BCCH5351
BCCG1854

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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
Andreas Braun et al.
Microbial cell factories, 11, 106-106 (2012-08-11)
Yarrowia lipolytica efficiently metabolizes and assimilates hydrophobic compounds such as n-alkanes and fatty acids. Efficient substrate uptake is enabled by naturally secreted emulsifiers and a modified cell surface hydrophobicity and protrusions formed by this yeast. We were examining the potential
Thomas S Muenz et al.
Die Naturwissenschaften, 99(5), 421-425 (2012-03-20)
Social work force distribution in honeybee colonies critically depends on subtle adjustments of an age-related polyethism. Pheromones play a crucial role in adjusting physiological and behavioral maturation of nurse bees to foragers. In addition to primer effects of brood pheromone
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
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