Ethyl benzylpyruvate

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H14O3
Molecular Weight	206.2378
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCOC(=O)C(=O)CCC1=CC=CC=C1

InChI

InChIKey=STPXIOGYOLJXMZ-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C12H14O3
Molecular Weight	206.2378
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18716813 | https://www.ncbi.nlm.nih.gov/pubmed/22480179

Ethyl 2-oxo-4-phenylbutyrate is useful for the synthesis of the important chiral precursor for angiotensin-converting enzyme (ACE) inhibitors.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Reductase CgKR2 (Candida glabrata) 1 Target ID: Reductase CgKR2 (Candida glabrata) Sources: https://www.ncbi.nlm.nih.gov/pubmed/22480179	Substrate 661
NADPH-dependent alpha-keto amide reductase 1 Target ID: Q07551 Gene ID: 851433.0 Gene Symbol: NA Target Organism: Saccharomyces cerevisiae (strain ATCC 204508 / S288c) (Baker's yeast) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15469278	Substrate 661
Putative reductase 1 1 Target ID: Q12458 Gene ID: 851974.0 Gene Symbol: YPR1 Target Organism: Saccharomyces cerevisiae (strain ATCC 204508 / S288c) (Baker's yeast) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15469278	Substrate 661
Putative 2-hydroxyacid dehydrogenase YGL185C 1 Target ID: P53100 Gene ID: 852690.0 Gene Symbol: NA Target Organism: Saccharomyces cerevisiae (strain ATCC 204508 / S288c) (Baker's yeast) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15469278	Substrate 661

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Genome hunting of carbonyl reductases from Candida glabrata for efficient preparation of chiral secondary alcohols.	2018-01	28978494
Semi-rational engineering of a thermostable aldo-keto reductase from Thermotoga maritima for synthesis of enantiopure ethyl-2-hydroxy-4-phenylbutyrate (EHPB).	2017-06-21	28638047
Cloning and characterization of three ketoreductases from soil metagenome for preparing optically active alcohols.	2016-10	27383399
Assessing the stereoselectivity of carbonyl reductases toward the reduction of OPBE and docking analysis.	2016-07	25989134
Towards the computational design and engineering of enzyme enantioselectivity: A case study by a carbonyl reductase from Gluconobacter oxydans.	2016-01-10	26590330
Crystallographic analysis of a novel aldo-keto reductase from Thermotoga maritima in complex with NADP⁺.	2015-07	26144229
Cloning, expression, and characterization of an anti-Prelog stereospecific carbonyl reductase from Gluconobacter oxydans DSM2343.	2015-03	25659628
A genomic search approach to identify carbonyl reductases in Gluconobacter oxydans for enantioselective reduction of ketones.	2014	25130736
Scalable biocatalytic synthesis of optically pure ethyl (R)-2-hydroxy-4-phenylbutyrate using a recombinant E. coli with high catalyst yield.	2013-12	24120725
Efficient synthesis of a chiral precursor for angiotensin-converting enzyme (ACE) inhibitors in high space-time yield by a new reductase without external cofactors.	2012-04-20	22480179
Engineering cofactor preference of ketone reducing biocatalysts: A mutagenesis study on a γ-diketone reductase from the yeast Saccharomyces cerevisiae serving as an example.	2010-04-14	20480039
Effect of ionic liquid [BMIM][PF6] on asymmetric reduction of ethyl 2-oxo-4-phenylbutyrate by Saccharomyces cerevisiae.	2008-11	18716813
Systematic investigation of Saccharomyces cerevisiae enzymes catalyzing carbonyl reductions.	2004-10-13	15469278

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Gox0525 showed useful specificity for 2-oxo-4-phenylbutyrate, with kcat/Km values of 1.719 × 10(4) M−1 s−1.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:27:00 GMT 2025` Edited by `admin` on `Mon Mar 31 18:27:00 GMT 2025`
Record UNII	5YNU9LPT51
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ETHYL PHENETHYLOXALATE

Preferred Name

English

Ethyl benzylpyruvate

Systematic Name

English

2-OXO-4-PHENYLBUTANOIC ACID ETHYL ESTER

Systematic Name

English

ETHYL 2-OXO-4-PHENYLBUTANOATE

Systematic Name

English

Code System Code Type Description

CAS

64920-29-2