29410-13-7

Usage

Uses

Used in Organic Synthesis:
5-Hydroxyhydantoin is used as a key intermediate in the synthesis of various organic compounds for [application reason]. Its chemical structure allows for the formation of new bonds and reactions, making it a valuable component in the creation of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 5-Hydroxyhydantoin is used as a building block for the development of new drugs and therapeutic agents. Its ability to participate in various chemical reactions enables the synthesis of complex molecules with potential medicinal properties.
Used in Agrochemical Industry:
5-Hydroxyhydantoin also finds application in the agrochemical industry, where it is used as a precursor for the synthesis of pesticides, herbicides, and other crop protection agents. Its versatility in organic synthesis contributes to the development of effective and targeted agrochemicals.
Used in Specialty Chemicals:
5-Hydroxyhydantoin is utilized in the production of specialty chemicals, such as dyes, pigments, and other performance-enhancing additives. Its unique chemical properties allow for the creation of innovative and high-quality specialty products.

InChI:InChI=1/C3H4N2O3/c6-1-2(7)5-3(8)4-1/h1,6H,(H2,4,5,7,8)

Upstream product

• 626-48-2 6-Methyluracil 
• 18592-13-7 6-chloromethyluracil 
• 71-30-7 Cytosine 
• 34557-54-5 methane 
• 57-13-6 urea 
• 66-22-8 uracil 

Downstream Products

• 111140-90-0 5-<(benzyloxycarbonyl)amino>hydantoin 
• 2420-17-9 5-(4-hydroxy-phenyl)-imidazolidine-2,4-dione 
• 120-89-8 parabanic acid 
• 461-72-3 2,4-imidazolidinedione 

Relevant academic research and scientific papers

Synthesis of pyrimidines and triazines in ice: Implications for the prebiotic chemistry of nucleobases

Herein, we report the efficient synthesis of RNA bases and func-tionalized s-triazines from 0.1 M urea solutions in water after subjection to freeze-thaw cycles for three weeks. The icy solution was under a reductive, methane-based atmosphere, which was s

Analysis of oxidative cytosine products in DNA exposed to ionizing radiation

From ionizing radiation studies, we have previously characterized a large number of modifications of cytosine and 2'-deoxycytidine which arise by way of hydroxyl radical or base radical cation reactions.However, it remains a great challenge today to detect and quantitate these lesions in DNA.In the present work, I have developed a method for the analysis of six oxidation products of cytosine in DNA using HF acid hydrolysis and gas chromatography/mass spectrometry with isotopic dilution.The analysis of gamma-irradiated DNA indicated that uracil 5,6-glycols 5-hydroxyuracil and 5-hydroxyhydantoin are the major stable decomposition products of cytosine residues, whereas alloxane and 1-carbamoyl-2-oxo-4,5-dihydroxy-imidazolidine are formed in comparatively lower yields.These results suggest that the major pathway of OH radical induced decomposition of cytosine in DNA involves initial deamination of intermediate 5-hydroxy-6-hydroperoxides. - Keywords: Oxidative DNA damage, mass spectrometry, isotopic dilution, mutagenesis.

Ozonolysis of Uracils in Water

The ozonolysis of uracils unsubstituted at the 1-position gave new 1-acyl-5-hydroxyhydantoins and 5-hydroxyhydantoins in water, while that of 1-substituted uracils gave the corresponding 5-hydroxyhydantoins in low yields.The structure of 1-acetyl-5-hydroxy-5-methylhydantoin was determined by X-ray crystallography.

The Radiolysis of Uracil in Oxygenated Aqueous Solutions. A Study by Product Analysis and Pulse Radiolysis

Hydroxyl radicals are generated by the radiolysis of N2O-O2 (4:1 v/v)-saturated aqueous solutions of uracil.They add to the 5,6-double bond of the substrate .These radicals are converted by oxygen into the corresponding peroxyl radicals (I) and (II), respectively.Peroxyl radical (I) undergoes a base-induced O2(1-.) elimination (kobs 8x1E3 s-1 at pH 10.5).As an intermediate 5-hydroxy-isopyrimidine is formed which rearranges into isobarbituric acid and adds water forming 5,6-dihydro-5,6-dihydroxyuracil.Competing with this base-induced reaction of radical (I) there is a bimolecular decay of radicals (I) and (II).These processes become predominant at low pH.For this reason a strong pH dependence of G (products) is observed.The major products are (G values at pH 3 and 10 in parentheses) 5,6-dihydroxy-5,6-dihydrouracil (1.1; 2.4), isobarbituric acid (0; 1.2), N-formyl-5-hydroxyhydantoin (1.6; 0.2), 5-hydroxybarbituric acid (0.9; 0.2). 5-Hydroxybarbituric acid is formed in its keto form.Its deprotonation (k 4.4 s-1) has been followed by pulse conductometry.Details of the reaction mechanism, e.g. the involvement of oxyl radicals in the bimolecular decay of (I) and (II), are discussed.

The sonolysis of uracil

The sonolysis of uracil (1) has been studied at 630 kHz in the presence of air, oxygen, nitrogen and argon.The degradation products were identified by gc-ms analysis.Under aerated conditions the following products were found: uracil glycols (7), isobarbituric acid (8), N-formyl-N'-glyoxylurea (6), 5-hydroxyhydantoin (9), dialuric acid (10), alloxan monohydrate (12), parabanic acid (13), and oxaluric acid (14).In deaerated solutions 6, 13, and 14 were not observed but either 6-hydroxy-5,6-dihydrouracil (17) or its isomer (18) were detected in addition to 7, 8, 9, 10, and 12.The observed products have been used to develop a possible mechanism for the sonolytic degradation and the results are similar to those obtained in radiolysis.The sonolytic degradation of 5-bromouracil (19) is also reported: the products observed were 5-bromobarbituric acid (20), 12, 13, 14, and 9 and these can be rationalized by a similar mechanism scheme.