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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H16O3
Molecular Weight 244.2857
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NAPROXEN METHYL ESTER

SMILES

COC(=O)[C@@H](C)C1=CC=C2C=C(OC)C=CC2=C1

InChI

InChIKey=ZFYFBPCRUQZGJE-JTQLQIEISA-N
InChI=1S/C15H16O3/c1-10(15(16)18-3)11-4-5-13-9-14(17-2)7-6-12(13)8-11/h4-10H,1-3H3/t10-/m0/s1

HIDE SMILES / InChI

Molecular Formula C15H16O3
Molecular Weight 244.2857
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Naproxen methyl ester, a mixture of two isomers R and S, is the precursor of therapeutically important nonsteroidal anti-inflammatory drug naproxen. Naproxen methyl ester can be enantioselectively hydrolyzed by lipases or (S)-enantioselective esterase could catalyze the selective hydrolysis of the (S)-Naproxen methyl ester, giving optically pure (S)-naproxen. In addition, S-naproxen methyl ester is used as a tool for identification and determination of new stereo selective carboxylesterase activities.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
PubMed

PubMed

TitleDatePubMed
Investigation of lipase-catalysed hydrolysis of naproxen methyl ester: use of NMR spectroscopy methods to study substrate-enzyme interaction.
2002 Aug
Use of stable emulsion to improve stability, activity, and enantioselectivity of lipase immobilized in a membrane reactor.
2003 Dec 20
Effect of immobilization site and membrane materials on multiphasic enantiocatalytic enzyme membrane reactors.
2003 Mar
A parametric study on biphasic medium conditions for the enantioselective production of naproxen by Candida rugosa lipase.
2007 Apr
Effects of alcohol and buffer treatments on the activity and enantioselectivity of Candida rugosa lipase.
2009
Carboxylic ester hydrolases from hyperthermophiles.
2009 Jul
Efficient production of (S)-naproxen with (R)-substrate recycling using an overexpressed carboxylesterase BsE-NP01.
2010 Nov
Patents

Patents

Substance Class Chemical
Created
by admin
on Tue Oct 22 13:41:08 UTC 2019
Edited
by admin
on Tue Oct 22 13:41:08 UTC 2019
Record UNII
571OJX4PDN
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NAPROXEN METHYL ESTER
Common Name English
NAPROXEN IMPURITY E [EP]
Common Name English
2-NAPHTHALENEACETIC ACID, 6-METHOXY-.ALPHA.-METHYL-, METHYL ESTER, (.ALPHA.S)-
Systematic Name English
(+)-NAPROXEN METHYL ESTER
Common Name English
NAPROXEN SODIUM IMPURITY E [EP]
Common Name English
(S)-NAPROXEN METHYL ESTER
Common Name English
METHYL (2S)-2-(6-METHOXYNAPHTHALEN-2-YL)PROPANOATE
Systematic Name English
Code System Code Type Description
PUBCHEM
9899603
Created by admin on Tue Oct 22 13:41:08 UTC 2019 , Edited by admin on Tue Oct 22 13:41:08 UTC 2019
PRIMARY
EPA CompTox
26159-35-3
Created by admin on Tue Oct 22 13:41:08 UTC 2019 , Edited by admin on Tue Oct 22 13:41:08 UTC 2019
PRIMARY
CAS
26159-35-3
Created by admin on Tue Oct 22 13:41:08 UTC 2019 , Edited by admin on Tue Oct 22 13:41:08 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
UNSPECIFIED
EP
PARENT -> IMPURITY
UNSPECIFIED
EP