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Merck
CN

268011

Ethyl oleate

98%

Synonym(s):

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:
24856257
EC Number:
203-889-5
Beilstein/REAXYS Number:
1727318
MDL number:
MFCD00009579

Key Documents

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Product Name

Ethyl oleate, 98%

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

assay

98%

form

liquid

refractive index

n20/D 1.451 (lit.)

bp

216-218 °C/15 mmHg

mp

−32 °C (lit.)

solubility

chloroform: soluble 10%

density

0.87 g/mL at 25 °C (lit.)

functional group

ester

storage temp.

−20°C

Quality Level

100

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Application

Ethyl oleate can be used as a starting material to synthesize stearic acid hydrazide intermediate, which can undergo intermolecular cyclization reaction with various aliphatic acids and aromatic acids to yield 1,3,4-oxadiazole derivatives. It is also reduced to oleyl alcohol via Bouveault−Blanc reduction reaction.
Ethyl oleate was used to prepare the oily phase of self-microemulsifying drug delivery system (SMEDDS) for tacrolimus (Tac).

Storage Class

10 - Combustible liquids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ4152
MKCX7554
MKCW2690
MKCQ2486
MKCQ2434

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Brian S Bodnar et al.
The Journal of organic chemistry, 74(6), 2598-2600 (2009-02-18)
Significantly improved Bouveault-Blanc conditions for ester reduction have been developed using sodium in silica gel (Na-SG), a free-flowing powder that can be easily handled in the open atmosphere. Primary alcohols were prepared in excellent yield from a variety of aliphatic
Kalidas Ramamoorthy et al.
American journal of physiology. Gastrointestinal and liver physiology, 321(2), G123-G133 (2021-06-03)
Vitamin B7 (biotin) is essential for normal health and its deficiency/suboptimal levels occur in a variety of conditions including chronic alcoholism. Mammals, including humans, obtain biotin from diet and gut-microbiota via absorption along the intestinal tract. The absorption process is
Marietta von Suesskind-Schwendi et al.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 67(6), 469-473 (2013-05-15)
This study evaluated the pharmacokinetics of tacrolimus (Tac) in a novel self-microemulsifying drug delivery system (SMEDDS) for improved oral administration. SMEDDS Tac consisted of ethyl oleate as the oily phase, Solutol HS 15 as the surfactant and glycofurol as the
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
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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