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375322

Ethyl 2-oxo-4-phenylbutyrate

Name: Ethyl 2-oxo-4-phenylbutyrate
Brand: ALDRICH

97%

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About This Item

Linear Formula:

C₆H₅CH₂CH₂COCOOCH₂CH₃

CAS Number:

64920-29-2

Molecular Weight:

206.24

UNSPSC Code:

12352100

NACRES:

NA.22

PubChem Substance ID:

24863381

EC Number:

265-276-9

Beilstein/REAXYS Number:

2725083

MDL number:

MFCD00037533

Assay:

97%

Form:

liquid

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Properties

assay

97%

form

liquid

refractive index

n20/D 1.504 (lit.)

bp

132 °C/2 mmHg (lit.)

density

1.091 g/mL at 25 °C (lit.)

SMILES string

CCOC(=O)C(=O)CCc1ccccc1

InChI

1S/C12H14O3/c1-2-15-12(14)11(13)9-8-10-6-4-3-5-7-10/h3-7H,2,8-9H2,1H3

InChI key

STPXIOGYOLJXMZ-UHFFFAOYSA-N

Description

General description

Ethyl 2-oxo-4-phenylbutyrate is an aliphatic α-ketoester. Bioreduction of ethyl 2-oxo-4-phenylbutyrate is reported to yield ethyl (R)-2-hydroxy-4-phenylbutanoate. The effect of ionic liquid on the asymmetric reduction of ethyl 2-oxo-4-phenylbutyrate by Saccharomyces cerevisiae has been reported. Asymmetric reduction of ethyl 2-oxo-4-phenylbutyrate using a bacterial reductase is reported. Enantioselective hydrogenation of ethyl 2-oxo-4-phenylbutyrate using homogeneous Rh-diphosphine and heterogeneous Pt/Al₂O₃-cinchona catalysts has been reported.

Application

Ethyl 2-oxo-4-phenylbutyrate may be used in the synthesis of ethyl (R)-2-hydroxy-4-phenylbutyrate, an important chiral precursor for angiotensin-converting enzyme (ACE) inhibitor.

Storage Class

10 - Combustible liquids

wgk

WGK 2

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

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Efficient Reduction of Ethyl 2-Oxo-4-phenylbutyrate at 620 g? L- 1 by a Bacterial Reductase with Broad Substrate Spectrum.

Ni Y, et al.

J. Mol. Catal. A: Chem., 107(1), 85-94 (1996)

Effect of ionic liquid [BMIM][PF6] on asymmetric reduction of ethyl 2-oxo-4-phenylbutyrate by Saccharomyces cerevisiae.

Yu-Gang Shi et al.

Journal of industrial microbiology & biotechnology, 35(11), 1419-1424 (2008-08-22)

The effect of ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate ([BMIM][PF6]) on the asymmetric reduction of ethyl 2-oxo-4-phenylbutyrate (EOPB) to synthesize optical active ethyl 2-hydroxy-4-phenylbutyrate (EHPB) catalyzed by Saccharomyces cerevisiae was investigated. (R)-EHPB [70.4%, e.e.(R)] is obtained using ethyl ether or benzene as

Efficient synthesis of a chiral precursor for angiotensin-converting enzyme (ACE) inhibitors in high space-time yield by a new reductase without external cofactors.

Nai-Dong Shen et al.

Organic letters, 14(8), 1982-1985 (2012-04-07)

A new reductase, CgKR2, with the ability to reduce ethyl 2-oxo-4-phenylbutyrate (OPBE) to ethyl (R)-2-hydroxy-4-phenylbutyrate ((R)-HPBE), an important chiral precursor for angiotensin-converting enzyme (ACE) inhibitors, was discovered. For the first time, (R)-HPBE with >99% ee was produced via bioreduction of

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Global Trade Item Number

SKU	GTIN
375322-25ML	04061836684952
375322-5ML	04061831834970