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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

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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

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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
Brian T Bennett et al.
Oxidative medicine and cellular longevity, 2020, 3938672-3938672 (2020-08-11)
Beta-hydroxy-beta-methylbutyrate (HMB), a naturally occurring leucine metabolite, has been shown to attenuate plantar flexor muscle loss and increase myogenic stem cell activation during reloading after a period of significant muscle wasting by disuse in old rodents. However, it was less
Carlos Castillo et al.
Insect biochemistry and molecular biology, 42(6), 404-416 (2012-03-13)
Honey bees undergo a physiological transition from nursing to foraging approximately 21 days after adult emergence. This transition is delayed by ethyl oleate (EO), a primer pheromone produced by foragers when exposed to ethanol from fermented nectar. We demonstrate here
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
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