72442-37-6

Basic information

• Product Name: 1-methyl-5-oxo-DL-proline
• Synonyms: 1-methyl-5-oxo-DL-proline;1-Methyl-5-oxo-Proline;1-methyl-5-oxopyrrolidine-2-carboxylic acid
• CAS NO: 72442-37-6
• Molecular Formula: C₆H₉NO₃
• Molecular Weight: 143.14056
• EINECS: 276-664-2
• Mol File: 72442-37-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 158 °C
• Boiling Point: 361.7°Cat760mmHg
• Flash Point: 172.5°C
• Appearance: /
• Density: 1.319g/cm³
• Vapor Pressure: 3.26E-06mmHg at 25°C
• Refractive Index: 1.519
• Storage Temp.: 2-8°C
• PKA: 3.53±0.20(Predicted)
• CAS DataBase Reference: 1-methyl-5-oxo-DL-proline(CAS DataBase Reference)
• NIST Chemistry Reference: 1-methyl-5-oxo-DL-proline(72442-37-6)
• EPA Substance Registry System: 1-methyl-5-oxo-DL-proline(72442-37-6)

Safety Data

• Hazardous Substances Data: 72442-37-6(Hazardous Substances Data)

Usage

Classification

A derivative of the amino acid proline, classified as an organic compound.

Physical state

Crystalline solid.

Solubility

Soluble in water.

Taste

Slightly acidic.

Usage

Commonly used as a building block in the synthesis of pharmaceuticals and other organic compounds.

Potential properties

Exhibits potential antimicrobial and antifungal properties.

Applications

Valuable ingredient in certain industrial and agricultural applications.

Role

Plays a significant role in various chemical and biological processes due to its unique properties and versatile applications.

InChI:InChI=1/C6H9NO3/c1-7-4(6(9)10)2-3-5(7)8/h4H,2-3H2,1H3,(H,9,10)/t4-/m0/s1

Upstream product

• 6312-54-5 N,N-dimethyl-(L)-glutamic acid 
• 108645-70-1 ethyl 1-methyl-5-oxopyrrolidine-2-carboxylate 
• 6753-62-4 N-methyl-L-glutamic acid 
• 190783-99-4 (S)-methyl 1-methyl-5-oxopyrrolidine-2-carboxylate 

Downstream Products

• 42435-90-5 1-methyl-5-oxoprolyl chloride 
• 128100-37-8 5-(4-methoxyphenyl)-1-methylpyrrolidin-2-one 
• 128100-36-7 5-(2-Methoxy-phenyl)-1-methyl-pyrrolidin-2-one 
• 128100-33-4 1-Methyl-5-p-tolyl-pyrrolidin-2-one 
• 128100-32-3 1-Methyl-5-m-tolyl-pyrrolidin-2-one 
• 128100-31-2 1-Methyl-5-o-tolyl-pyrrolidin-2-one 
• 54520-83-1 1-methyl-5-phenyl-2-pyrrolidinone 
• 106116-32-9 4,5-Dichlor-1-methyl-1H-pyrrol-2-carbonylchlorid 
• 106116-34-1 5-Chlor-1-methyl-1H-pyrrol-2-carbonylchlorid 
• 106116-35-2 3,5-Dichlor-1-methyl-1H-pyrrol-2-carbonylchlorid 

Relevant articles and documents

Metal-catalyzed reductive deamination of glutamic acid to bio-based dimethyl glutarate and methylamines

Glutamic acid is a promising renewable platform molecule which is abundantly available in biomass waste streams; it is also efficiently manufactured by fermentation. Here we report the reductive deamination of glutamic acid to bio-based dimethyl glutarate and methylamines. In order to recycle nitrogen in an industrially relevant co-product, glutamic acid was modified to N,N-dimethylglutamic acid by a mild reductive alkylation with Pd/C. Subsequently, selective C-N hydrogenolysis in methanol resulted in dimethyl glutarate and trimethylamine. A wide screening of transition metals (Pt, Pd, Rh and Ru) immobilized on various supports showed that the highest yields of dimethyl glutarate were obtained with Pt/TiO2. An FTIR study and kinetic experiments on metal-loaded and unloaded supports demonstrate that the interplay between the metal and the moderate acidity of the support results in the excellent C-N hydrogenolysis activity and selectivity. Finally, reaction parameter optimization resulted in 81% yield of dimethyl glutarate with 1 wt% Pt/TiO2 at 225 °C, 30 bar H2 after 8 h.

New AZT conjugates as potent anti-HIV agents

In an attempt to discover anti-HIV agents with much reduced cytotoxicity from the currently available HIV-reverse transcriptase inhibitors, AZT conjugates of cholanic acids, 2-imidazolidone-4-carboxylic acid and its derivatives, and N,N′-disubstituted 5-hydroxy-tetrahydropyrimidin-2-ones have been synthesized and their anti-HIV profiles determined with CEM-SS cell line. The AZT conjugates with 2-imidazolidone-4-carboxylic acid and 2-pyrrolidone-5-carboxylic acid through an ester linkage, and with N,N′-diphenyl-5-hydroxy-tetrahydropyrimidin-2-one through a succinate tether showed significantly higher therapeutic indexes than AZT while they also retained or enhanced AZT's anti-HIV activity. Thus, structural features that favor the desired therapeutic profile of the conjugates appear to include a five-membered ring cyclic urea or lactam, and six-membered ring cyclic urea with N,N′-diphenyl substitution. Copyright Taylor & Francis Group, LLC.