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Sigma-Aldrich

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
Beilstein:
1727318
EC Number:
203-889-5
MDL number:
MFCD00009579
UNSPSC Code:
12352100
PubChem Substance ID:
57652552
NACRES:
NA.22

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.)

SMILES string

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

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-

InChI key

LVGKNOAMLMIIKO-QXMHVHEDSA-N

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Application

Ethyl oleate can be used as a model for fats to study their degree of ozonization and decomposition enthalpy of ozonides.

Storage Class Code

10 - Combustible liquids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
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
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