IBUPROFEN METHYL ESTER

Details

Stereochemistry	RACEMIC
Molecular Formula	C14H20O2
Molecular Weight	220.3074
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC(=O)C(C)C1=CC=C(CC(C)C)C=C1

InChI

InChIKey=YNZYUHPFNYBBFF-UHFFFAOYSA-N

InChI=1S/C14H20O2/c1-10(2)9-12-5-7-13(8-6-12)11(3)14(15)16-4/h5-8,10-11H,9H2,1-4H3

HIDE SMILES / InChI

Molecular Formula	C14H20O2
Molecular Weight	220.3074
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: A. N. Collins, G. N. Sheldrake, J. Crosby (1997) 'Chirality in Industry II: Developments in the Commercial Manufacture and Applications of Optically Active Compounds', p.33-34 Retrieved from https://books.google.ru/books?id=Ei54_7j8VzEC | doi: 10.1016/j.molcatb.2014.03.005

The methyl ester of ibuprofen is the most common starting material for the enzymatic resolution process based on selective hydrolyses of racemic mictures of ibuprofen esters. Addition of the methyl ester of racemic ibuprofen to growing cultures of Pseudomonas, Mucor, Arthrobacter or Bacillus species produced (S)-(+)-ibuprofen in 74-98% ee. Lipase from Candida rugosa hydrolyses racemic ibuprofen methyl ester to give 95% ee (S)-(+)-ibuprofen.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Candida cylindracea lipase 1 Target ID: Candida cylindracea lipase Sources: DOI: 10.1016/0922-338X(96)87742-7	Substrate 661

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

The highest enantioselectivity for hydrolysis of ibuprofen methyl ester was observed at 40 ◦C by using 5 mg of the immobilized enzyme in n-hexane with eeP 96.3%, c 6.4 and E value of 56.1.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:14:32 GMT 2025` Edited by `admin` on `Mon Mar 31 22:14:32 GMT 2025`
Record UNII	8F58KSV2GP
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

IBUPROFEN METHYL ESTER

Common Name

English

(±)-IBUPROFEN METHYL ESTER

Preferred Name

English

BENZENEACETIC ACID, .ALPHA.-METHYL-4-(2-METHYLPROPYL)-, METHYL ESTER

Systematic Name

English

2-(4-ISOBUTYLPHENYL)PROPIONIC ACID METHYL ESTER

Systematic Name

English

RACEMIC IBUPROFEN METHYL ESTER

Common Name

English

METHYL 2-(4'-ISOBUTYLPHENYL)PROPANOATE

Common Name

English

METHYL 2-(P-ISOBUTYLPHENYL)PROPIONATE

Common Name

English

METHYL 2-(4-ISOBUTYLPHENYL)PROPIONATE

Systematic Name

English

METHYL .ALPHA.-(P-ISOBUTYLPHENYL)PROPIONATE

Common Name

English

METHYL .ALPHA.-(4-ISOBUTYLPHENYL)PROPIONATE

Systematic Name

English

Code System Code Type Description

PUBCHEM

109101