5262-10-2

Basic information

• Product Name: 5-BENZYL-3,6-DIOXO-2-PIPERAZINEACETIC ACID
• Synonyms: 5-BENZYL-3,6-DIOXO-2-PIPERAZINEACETIC ACID;(2S-CIS)-(-)-5-BENZYL-3,6-DIOXO-2-PIPERAZINEACETIC ACID;CYCLO(-ASP-PHE);CYCLO(L-ASP-L-PHE);(2S-cis)-(-)-5-benzyl-3,6-dioxo-2-piperazineaceti;cyclo(aspartyl-phenylalanyl);(2S)-3,6-Dioxo-5β-(phenylmethyl)-2β-piperazineacetic acid;(2S)-3,6-Dioxo-5β-benzylpiperazine-2β-acetic acid
• CAS NO: 5262-10-2
• Molecular Formula: C₁₃H₁₄N₂O₄
• Molecular Weight: 262.26
• EINECS: 226-075-1
• Product Categories: Chiral Building Blocks;Heterocyclic Building Blocks;Piperazines;Aromatics;Heterocycles;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 5262-10-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 270-272 °C(lit.)
• Boiling Point: 667.4°Cat760mmHg
• Flash Point: 357.4°C
• Appearance: /
• Density: 1.298g/cm³
• Vapor Pressure: 1.02E-18mmHg at 25°C
• Refractive Index: 1.561
• Storage Temp.: -15°C
• Solubility: Acetic Acid (Slightly, Heated, Sonicated), DMSO (Slightly), Methanol (Very Sligh
• PKA: 4.02±0.10(Predicted)
• CAS DataBase Reference: 5-BENZYL-3,6-DIOXO-2-PIPERAZINEACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BENZYL-3,6-DIOXO-2-PIPERAZINEACETIC ACID(5262-10-2)
• EPA Substance Registry System: 5-BENZYL-3,6-DIOXO-2-PIPERAZINEACETIC ACID(5262-10-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 5262-10-2(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 5262-10-2 differently. You can refer to the following data:
1. The diketopiperazine impurity of the sweetening agent Aspartame (A790015). It is also found in in processed cocoa powder.
2. (2S,5S)-5-Benzyl-3,6-dioxo-2-piperazineacetic Acid (Aspartame EP Impurity A) is the diketopiperazine impurity of the sweetening agent Aspartame (A790015). It is also found in in processed cocoa powder.

General Description

(2S-cis)-(-)-5-Benzyl-3,6-dioxo-2-piperazineacetic acid is a piperazine scaffold that can be used to construct biologically active compounds with therapeutic applications.

InChI:InChI=1/C13H14N2O4/c16-11(17)7-10-13(19)14-9(12(18)15-10)6-8-4-2-1-3-5-8/h1-5,9-10H,6-7H2,(H,14,19)(H,15,18)(H,16,17)/t9-,10-/m0/s1

Upstream product

• 22839-47-0 L-Asp-L-Phe-OMe 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 

Downstream Products

• 1450838-00-2 (S)-2-(2-((2S,5S)-5-benzyl-3,6-dioxopiperazin-2-yl)acetamido)-6-ethanethioamido-N-(2-oxo-2-phenylethyl)hexanamide 
• 874811-52-6 ((2S,5S)-5-Benzyl-3,6-dioxo-piperazin-2-yl)-acetic acid 11-bromo-undecyl ester 
• 881492-61-1 cyclo(L-10-bromodecylasparaginyl-L-phenylalanine) 

Relevant articles and documents

Synthesis and solvent-controlled self-assembly of diketopiperazine-based polyamides from aspartame

An aspartame-based AB-type diketopiperazine monomer, cyclo(l-aspartyl-4-amino-l-phenylalanyl) (ADKP), was synthesized and subsequently utilized in the polycondensation of homo-polyamides with high molecular weights. By using various amino acids, dicarboxylic acids, and diamines, random DKP-based copolymers were also synthesized. The self-assembly properties of ADKP and poly(cyclo(l-aspartyl-4-amino-l-phenylalanyl)) (PA1) were studiedviathe solvent displacement method. Notably, PA1 self-assembled into particles with various morphologies in different solvent systems, such as irregular networks, ellipsoids, and hollow particles. The morphological transformation was also confirmed by dropping acetone and toluene onto the PA1 particles. Furthermore, infrared spectra and Hansen solubility parameters of PA1 and different solvents revealed the particle formation mechanism, which provided more insights into the relationship between the morphology and strength of the hydrogen bonding of each solvent.

Cyclo(dipeptide) as Low-molecular-mass Gelling Agents to Harden Organic Fluids

Cyclic dipeptides consisting of diverse amino acids can cause physical gelation in a wide variety of organic fluids, including edible oils, glyceryl esters, alcohols and aromatic molecules; the gelation phenomenon is characterized by minimum gel concentration, FTIR spectroscopy, transmission electron microscopy, and X-ray diffraction.

Stability of aspartame in water:organic solvent mixtures with different dielectric constants

In order to examine the influence of solvent composition on the stability of aspartame (N-α-L-aspartyl-L-phenylalanine-1-methyl ester) in solution (5 mg/mL), the degradation of aspartame was carried out in water:methanol, water:ethanol, and water:glycerine mixtures with dielectric constant values of 45, 55, and 65, respectively. The rate of disappearance of aspartame was measured by a sensitive HPLC assay. The degradation rate of aspartame increased as the dielectric constant of the solvent mixture decreased in all three solvents systems. For example, at 60 °C, the degradation rate constants were 4.1, 5.9, and 8.4 x 10-3 h-1 at dielectric constant of 65, 55, and 45, respectively. From these results, it can be concluded that the stability of aspartame in aqueous solutions cannot be enhanced by the replacement of water by solvents of lower dielectric constant.