6301-02-6

Basic information

• Product Name: 1-AMINOHYDANTOIN
• Synonyms: 1-AMINOHYDANTOIN;1-AMINO-IMIDAZOLIDINE-2,4-DIONE
• CAS NO: 6301-02-6
• Molecular Formula: C₃H₅N₃O₂
• Molecular Weight: 115.09
• EINECS: 228-593-3
• Mol File: 6301-02-6.mol

Chemical Properties

• Melting Point: 195-196 °C
• Appearance: /
• Density: 1.506 g/cm³
• Refractive Index: 1.556
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Acetonitrile (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 7.88±0.10(Predicted)
• CAS DataBase Reference: 1-AMINOHYDANTOIN(CAS DataBase Reference)
• NIST Chemistry Reference: 1-AMINOHYDANTOIN(6301-02-6)
• EPA Substance Registry System: 1-AMINOHYDANTOIN(6301-02-6)

Safety Data

• Hazardous Substances Data: 6301-02-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-Aminohydantoin is used as a key intermediate for the synthesis of various drugs, contributing to the development of new medications and therapeutic agents. Its unique chemical structure allows for the creation of diverse organic compounds, making it a valuable building block in the pharmaceutical field.
Used in Agrochemical Industry:
As a precursor in the production of agrochemicals, 1-Aminohydantoin plays a crucial role in the development of agricultural products, such as pesticides and herbicides. Its versatility in chemical synthesis enables the creation of effective compounds that can enhance crop protection and yield.
Used in Sweetener Production:
1-Aminohydantoin is used as an intermediate in the synthesis of sucralose, a popular non-caloric sweetener. Its involvement in the production process highlights its importance in the food and beverage industry, where it contributes to the creation of healthier and sugar-free alternatives.
Used in Genetic Toxicity Research:
1-Aminohydantoin is employed as a mutagen in studies aimed at assessing genetic toxicity. Its ability to induce mutations makes it a valuable tool for researchers investigating the effects of various substances on genetic material, further expanding its applications in scientific research.

InChI:InChI=1/C3H5N3O2/c4-6-1-2(7)5-3(6)8/h1,4H2,(H,5,7,8)

Upstream product

• 138-07-8 2-semicarbazide acetic acid 
• 590-28-3 potassium cyanate 
• 6945-92-2 2-hydrazinyl acetic acid ethyl ester hydrochloride 
• 67-20-9 Nitrofurantoin 

Downstream Products

• 777-34-4 1-Amino-N-<5-nitro-furfur-2-yliden>-hydantoin 
• 101655-00-9 1-(4-ethanesulfonyl-benzylidenamino)-imidazolidine-2,4-dione 
• 67-20-9 Nitrofurantoin 
• 17577-67-2 1-(4-nitro-benzylideneamino)-imidazolidine-2,4-dione 
• 833480-90-3 dantrolene 

Relevant articles and documents

Photolytic and photocatalytic degradation of nitrofurantoin and its photohydrolytic products

TiO2 based photocatalytic degradation of nitrofurantion (NFT), a widely used drug, and its primary decomposition products, nitrofuraldehyde (NFA) and aminohydantoin (AHD) was investigated and compared to their photolysis in aerobic systems. UV–vis spectrophotometry, pH, IC, and HPLC measurements were applied to follow the changes during the irradiations and subsequently, in the dark. After a fast anti→syn (or trans→cis) photoisomerization of NFT (giving i-NFT), a slower photohydrolysis of both isomers took place upon UV excitation, leading to the formation of NFA and AHD. i-NFT proved to be more reactive than NFT; it underwent hydrolysis in the dark, too. While photolysis could not totally convert NFT and i-NFT within 120 min, they disappeared within 90 min during the photocatalysis under the same irradiation conditions, along with the degradation of NFA and AHD, and the accumulation of a rather stable intermediate identified as 5-hydroxyfuran-2-carbaldehyde, formed from NFA. The direct photolysis of NFA also gave this characteristic intermediate along with its several derivatives formed via addition or condensation then redox transformations. They very slowly decomposed in photolysis, while totally disappeared during photocatalysis of NFA, producing polar aliphatic intermediates. Direct irradiation could not convert AHD, while photocatalysis led to its significant degradation in aerobic system. These results indicate that TiO2 based photocatalysis is suitable for the efficient decomposition of NFT and their photoderivatives.

Microsomal oxidative stress induced by NADPH is inhibited by nitrofurantoin redox biotranformation

Nitrofurantoin is used in the antibacterial therapy of the urinary tract. This therapy is associated with various adverse effects whose mechanisms remain unclear. Diverse studies show that the nitro reductive metabolism of nitrofurantoin leads to ROS generation. This reaction can be catalyzed by several reductases, including the cytochrome P450 (CYP450) reductase. Oxidative stress arising from this nitro reductive metabolism has been proposed as the mechanism underlying the adverse effects associated with nitrofurantoin. There is, however, an apparent paradox between these findings and the ability of nitrofurantoin to inhibit lipid peroxidation provoked by NADPH in rat liver microsomes. This work was aimed to show the potential contribution of different enzymatic systems to the metabolism of this drug in rat liver microsomes. Our results show that microsomal lipid peroxidation promoted by NADPH is inhibited by nitrofurantoin in a concentration-dependent manner. This suggests that the consumption of NADPH in microsomes can be competitively promoted by lipid peroxidation and nitrofurantoin metabolism. The incubation of microsomes with NADPH and nitrofurantoin generated 1-aminohidantoin. In addition, the biotransformation of a classical substrate of CYP450 oxidative system was competitively inhibited by nitrofurantoin. These results suggest that nitrofurantoin is metabolized through CYP450 system. Data are discussed in terms of the in vitro redox metabolism of nitrofurantoin.

PROCESS FOR STRAIGHTENING KERATIN FIBRES WITH A HEATING MEANS AND DENATURING AGENTS

The invention relates to a process for straightening keratin fibres, comprising: (i) a step in which a straightening composition containing at least two denaturing agents is applied to the keratin fibres, (ii) a step in which the temperature of the keratin fibres is raised, using a heating means, to a temperature of between 110 and 250° C.