64622-17-9

Usage

Uses

Used in Pharmaceutical Industry:
Ibuprofen Isopropyl Ester is used as a prodrug for Ibuprofen to improve its topical delivery. This enhanced delivery system aims to provide more effective pain relief and inflammation management when applied directly to the skin or affected area, offering an alternative to oral administration and potentially reducing systemic side effects.
Used in Pain Management Applications:
Ibuprofen Isopropyl Ester serves as an effective prodrug for Ibuprofen, providing targeted pain relief and anti-inflammatory action when applied topically. This can be particularly beneficial for localized conditions such as muscle strains, joint inflammation, or other forms of localized pain, allowing for direct treatment without the need for systemic absorption.
Used in Sports Medicine:
In the field of sports medicine, Ibuprofen Isopropyl Ester can be utilized as a topical treatment to help manage inflammation and pain associated with athletic injuries or overexertion. Its improved topical delivery allows for more focused relief, which can be advantageous for athletes seeking to minimize discomfort and promote faster recovery.
Used in Dermatology:
Ibuprofen Isopropyl Ester may also find applications in dermatology, where its enhanced topical delivery can provide relief for skin conditions characterized by inflammation and pain, such as certain types of dermatitis or skin irritations. By applying the prodrug directly to the affected area, patients may experience reduced inflammation and discomfort with minimal systemic side effects.

Upstream product

• 71381-91-4 (+/-)-2-(4-isobutylphenyl)propanoyl chloride 
• 67-63-0 isopropyl alcohol 
• 15687-27-1 ibuprofen 
• 134018-89-6 (R,S)-ibuprofen vinyl ester 
• 51146-56-6 (S)-ibuprofen 
• 114438-61-8 isopropyl 2-bromopropanoate 
• 2051-99-2 1-bromo-4-isobutylbenzene 

Relevant academic research and scientific papers

Asymmetric cross-coupling of racemic α-bromo esters with aryl Grignard reagents catalyzed by cyclopropane-based bisoxazolines cobalt complexes

Four new cyclopropane-based bisoxazolines were synthesized and applied to cobalt-catalyzed cross-coupling reactions between racemic α-bromo esters and aryl Grignard reagents. The reaction afforded a series of chiral α-arylalkanoic esters with high yields and good enantioselectivities (up to 93% yield, 92:8 er). This research focuses on the cross-coupling between racemic α-bromopropanoate and p-isobutylphenyl Grignard reagent's which provides ibuprofen ester efficiently. Furthermore, ibuprofen ester 7e was transformed into (S)-ibuprofen (99:1 er) via hydrolysis and recrystallization.

Esterification of R/S-ketoprofen with 2-propanol as reactant and solvent catalyzed by Novozym 435 at selected conditions

The enzymatic esterification of R/S-ketoprofen with 2-propanol catalyzed with the commercial biocatalyst Novozym 435 is addressed in this investigation. The low reaction rate registered in this reaction was investigated in terms of the effect of the alcohol on the physicochemical- enzymatic stability of the biocatalyst and the interaction of the substrates with the catalytic triad at a molecular level. The effect of contacting 2-propanol:H2O mixture on Novozym 435 was investigated at 45 °C for an extended period of time (8 days). The mixture dissolves the polymethylmethacrylate (PMMA) that constitutes the support of the Candida antarctica B lipase (CALB). Additionally, the alcohol diffuses into the biocatalyst's beads remaining strongly adsorbed (the alcohol desorption is evidenced only upon heating at 187 °C) and altering the inner texture of the biocatalyst's beads. Additionally, 2-propanol modifies the secondary structure of the enzyme by decreasing the β-sheet contribution and increasing the β-turn structure. The molecular modeling of the interaction of R/S-ketoprofen and 2-propanol with the catalytic triad of the lipase provides evidences that the secondary alcohol exerts an important steric hindrance for the reaction to proceed.

Synthesis, characterization and in vitro hydrolysis studies of ester and amide prodrugs of dexibuprofen

Ten prodrugs of dexibuprofen having ester and amide moieties instead of free carboxylic acid which involves in gastrointestinal side effects have been synthesized. Dexibuprofen acid chloride was condensed with different amino acid methyl ester hydrochlorides and five alcohols to afford the amide and ester prodrugs. All of the synthesized prodrugs were characterized by their mp, Rf, elemental analysis, FTIR, 1H NMR, and 13C NMR spectroscopy. The in vitro hydrolysis studies in plasma reflect prodrugs have been varied in terms of reactivity toward hydrolysis, owing to the different chemical structures. In alkyl substitution the branched chain alkyl substituents or aromatic substituents resulted in enhanced lipophilicity but diminished dissolution and hydrolysis rate. The amide prodrugs with branched and aromatic substitution can also be considered for sustained release. Prodrugs are less irritating to gastric mucosa than dexibuprofen. Springer Science+Business Media, LLC 2011.

Potash alum [KAL(SO4)2.12H2O] catalysed esterification of formylphenoxyaliphatic acids

A convenient and clean procedure for esterification is reported. Direct condensation of formylphenoxyaliphatic acids with low to high boiling alcohols catalysed by potash alum gave moderate to good yields. This catalyst could be recovered and reused without substantial loss in its catalytic activity and the methodology could be used for a range of closely related substrates.

Protic acid immobilized on solid support as an extremely efficient recyclable catalyst system for a direct and atom economical esterification of carboxylic acids with alcohols

(Chemical Equation Presented) A convenient and clean procedure of esterification is reported by direct condensation of equimolar amounts of carboxylic acids with alcohols catalyzed by an easy to prepare catalyst system of perchloric acid immobilized on silica gel (HClO4-SiO2). The direct condensation of aryl, heteroaryl, styryl, aryl alkyl, alkyl, cycloalkyl, and long-chain aliphatic carboxylic acids with primary/secondary alkyl/cycloalkyl, allyl, propargyl, and long-chain aliphatic alcohols has been achieved to afford the corresponding esters in excellent yields. Chiral alcohol and N-t-Boc protected chiral amino acid also resulted in ester formation with the representative carboxylic acid or alcohol without competitive N-t-Boc deprotection and detrimental effect on the optical purity of the product demonstrating the mildness and chemoselectivity of the procedure. The esters of long-chain (>C10) acids and alcohols are obtained in high yields. The catalyst is recovered and recycled without significant loss of activity. The industrial application of the esterification process is demonstrated by the synthesis of prodrugs of ibuprofen and a few commercial flavoring agents. Other protic acids such as H2SO4, HBr, TfOH, HBF4, and TFA that were adsorbed on silica gel were less effective compared to HClO4-SiO2 following the order HClO4-SiO 2 ? H2SO4-SiO2 > HBr-SiO 2 > TfOH-SiO2 ? HBF4-SiO2 ≈ TFA-SiO2. When HClO4 was immobilized on other solid supports the catalytic efficiency followed the order HClO4-SiO 2 > HClO4-K10 > HClO4-Al 2O3 (neutral) > HClO4-Al2O 3 (acidic) > HClO4-Al2O3 (basic).

Lipase-catalyzed resolution of ibuprofen

The resolution of ibuprofen by transesterification of its corresponding vinylester using lipase B from Candida antarctica is described. Compared to transesterification or hydrolysis of the ibuprofen ethyl ester (E2, 28-48h), the reaction with vinylesters occurred significantly faster (1.5-5h) and with considerably higher enantioselectivity (E=8-39).

A practical new chiral controller for asymmetric Diels-Alder and alkylation reactions

(formula presented) The enantiomerically pure hydroxy sulfones (+)- and (-)-2 have been prepared from 1,2-epoxycyclohexane by a simple and practical procedure. The acrylate esters of these alcohols undergo BCl3-catalyzed Diels-Alder reactions with a variety of dienes at -78 to -55°C in CH2Cl2 or C7H8 with high dienophile face selectivity (Table 1). The chiral esters so formed are readily cleaved with recovery of the controllers (+)- or (-)-2. Esters of (+)- and (-)-2 can be converted to Z-polassium enolates and alkylated with high face selectivity.

Effect of group substitution on the physiochemical properties of ibuprofen prodrugs

A series of alkyl ester prodrugs of ibuprofen was synthesized and studied for its physicochemical properties like aqueous solubility, octanol-water partition coefficient and hydrolysis kinetics in aqueous buffer and human plasma. These physicochemical parameters have a forebearing on the overall activity profile of these prodrugs. Mathematical relationships have been derived to characterize these properties.