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268011

Sigma-Aldrich

Ethyl oleate

98%

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Synonym(s):
Oleic acid ethyl ester
Linear Formula:
CH3(CH2)7CH=CH(CH2)7COOC2H5
CAS Number:
Molecular Weight:
310.51
Beilstein/REAXYS Number:
1727318
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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.)

storage temp.

−20°C

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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1 of 4

This Item
317675751001266609
vibrant-m

268011

Ethyl oleate

vibrant-m

317675

Ethyl oleate

vibrant-m

75100

Ethyl oleate

vibrant-m

1266609

Ethyl oleate

form

liquid

form

liquid

form

liquid

form

-

storage temp.

−20°C

storage temp.

−20°C

storage temp.

-

storage temp.

−20°C

solubility

chloroform: soluble 10%

solubility

-

solubility

-

solubility

-

bp

216-218 °C/15 mmHg

bp

205-208 °C/760 mmHg, 216-218 °C/15 mmHg

bp

216-218 °C/15 mmHg

bp

216-218 °C/15 mmHg

density

0.87 g/mL at 25 °C (lit.)

density

0.87 g/mL at 25 °C (lit.)

density

0.87 g/mL at 25 °C (lit.)

density

0.87 g/mL at 25 °C (lit.)

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_germany

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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Oleyl oleate

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
Shujauddin Changi et al.
ChemSusChem, 5(9), 1743-1757 (2012-08-29)
We examined the behavior of phenylalanine in high-temperature water (HTW) at 220, 250, 280, and 350 °C. Under these conditions, the major product is phenylethylamine. The minor products include styrene and phenylethanol (1-phenylethanol and 2-phenylethanol), which appear at higher temperatures and

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