1175521-35-3

Basic information

• Product Name: 2,5-Dihydro-3-(1-methylethyl)-2,5-dioxo-1H-pyrrole-1-propanoic acid
• Synonyms: 2,5-Dihydro-3-(1-methylethyl)-2,5-dioxo-1H-pyrrole-1-propanoic acid;Farinomalein
• CAS NO: 1175521-35-3
• Molecular Formula: C10H13NO4
• Molecular Weight: 211
• Mol File: 1175521-35-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 384.632 °C at 760 mmHg
• Flash Point: 186.419 °C
• Appearance: /
• Density: 1.281
• CAS DataBase Reference: 2,5-Dihydro-3-(1-methylethyl)-2,5-dioxo-1H-pyrrole-1-propanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Dihydro-3-(1-methylethyl)-2,5-dioxo-1H-pyrrole-1-propanoic acid(1175521-35-3)
• EPA Substance Registry System: 2,5-Dihydro-3-(1-methylethyl)-2,5-dioxo-1H-pyrrole-1-propanoic acid(1175521-35-3)

Safety Data

• Hazardous Substances Data: 1175521-35-3(Hazardous Substances Data)

Usage

General Description

2,5-Dihydro-3-(1-methylethyl)-2,5-dioxo-1H-pyrrole-1-propanoic acid, also known as diketopiperazine, is a chemical compound with the molecular formula C9H12N2O4. It is a cyclic dipeptide formed from two amino acids and is found in a variety of natural sources, including certain fungi and bacteria. Diketopiperazine has been studied for its potential applications in pharmaceuticals, food additives, and as a precursor in the synthesis of other organic compounds. It has also been identified as an intermediate in the biosynthesis of certain natural products and has been investigated for its potential biological activities, including anticancer and antibiotic properties. Additionally, diketopiperazine has been studied for its role in the flavor development of various food products.

Upstream product

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Relevant articles and documents

Synthesis of farinomalein

Farinomalein, a recently isolated maleimide from Paecilomyces farinosus, was synthesized in two steps from a readily available γ-hydroxybutenolide.

Synthesis of natural maleimides farinomaleins C-E and evaluation of their antifungal activity

A practical and convenient synthesis of naturally occurring farinomaleins C-E was achieved starting from readily available ethyl 3-methyl-2-oxobutyrate and triethyl phosphonoacetate. The key steps of the sequence included a Horner-Wadsworth-Emmons condensation to obtain the precursor farinomalein A and coupling with suitable alcohols to install the chain. The synthesis of farinomalein D has been achieved starting from (R)-isopropylideneglycerol on the basis of which the S configuration was assigned to the natural compound. The antifungal activity of the synthesized compounds was evaluated against Cladosporium cladosporioides.

Improved synthesis of farinomalein and its analogs

A practical and convenient synthesis of the fungicidal natural compound farinomalein is described starting from readily available ethyl 3-methyl-2-oxobutyrate and triethyl phosphonoacetate, employing a Horner-Wadsworth-Emmons condensation as the key step. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.