503-83-3

Basic information

• Product Name: Tetramic acid
• Synonyms: Tetramic acid;5-hydroxy-1,2-dihydropyrrol-3-one;1,5-Dihydro-4-hydroxy-2H-pyrrol-2-one;Pyrrolidine-2,4-dione;4-Hydroxy-1H-pyrrol-2(5H)-one
• CAS NO: 503-83-3
• Molecular Formula: C₄H₅NO₂
• Molecular Weight: 99.09
• Mol File: 503-83-3.mol
• Article Data: 2

Chemical Properties

• Melting Point: 120 °C
• Boiling Point: 267.706 °C at 760 mmHg
• Flash Point: 115.705 °C
• Appearance: /
• Density: 1.425 g/cm³
• Vapor Pressure: 0.00108mmHg at 25°C
• Refractive Index: 1.579
• PKA: 4.50±1.00(Predicted)
• CAS DataBase Reference: Tetramic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Tetramic acid(503-83-3)
• EPA Substance Registry System: Tetramic acid(503-83-3)

Safety Data

• Hazardous Substances Data: 503-83-3(Hazardous Substances Data)

Usage

General Description

Tetramic acid is a class of organic compounds that contains a four-membered ring structure with a carbonyl group and an acidic proton. These compounds are found in natural products such as fungal and bacterial metabolites, and exhibit a wide range of biological activities including antimicrobial, antiviral, and antitumor properties. Tetramic acids are of interest to researchers due to their potential as lead compounds for drug development. Their versatile structure makes them attractive targets for the synthesis of new pharmaceuticals and agrochemicals. Additionally, tetramic acids have been used in the development of synthetic dyes, as well as in the production of insecticides and herbicides.

InChI:InChI=1/C4H5NO2/c6-3-1-4(7)5-2-3/h1,5,7H,2H2

Upstream product

• 51925-57-6 methyl 2,4-dioxo-3-pyrrolidinecarboxylate 

Relevant articles and documents

Synthesis of a leopolic acid-inspired tetramic acid with antimicrobial activity against multidrug-resistant bacteria

The increasing emergence of multidrug-resistant pathogens is one of the biggest threats to human health and food security. The discovery of new antibacterials, and in particular the finding of new scaffolds, is an imperative goal to stay ahead of the evolution of antibiotic resistance. Herein we report the synthesis of a 3-decyltetramic acid analogue of the ureido dipeptide natural antibiotic leopolic acid A. The key step in the synthetic strategy is an intramolecular Lacey-Dieckmann cyclization reaction of a linear precursor to obtain the desired 3-alkyl-substituted tetramic acid core. The synthesized analogue is more effective than the parent leopolic acid A against Gram-positive (Staphylococcus pseudintermedius) and Gram-negative (E. coli) bacteria (MIC 8 μg/mL and 64 μg/mL, respectively). Interestingly, the compound shows a significant activity against Staphylococcus pseudintermedius strains expressing a multidrug-resistant phenotype (average MIC 32 μg/mL on 30 strains tested). These results suggest that this molecule can be considered a promising starting point for the development of a novel class of antibacterial agents active also against resistant strains.