10045-58-6

Basic information

• Product Name: 5-HYDROXY-5-METHYLHYDANTOIN
• Synonyms: 5-HYDROXY-5-METHYLHYDANTOIN;5-Hydroxy-5-Methyl-
• CAS NO: 10045-58-6
• Molecular Formula: C4H6N2O3
• Molecular Weight: 130.1
• Product Categories: Hydantoins and Derivatives;Hydantoins & Derivatives
• Mol File: 10045-58-6.mol

Chemical Properties

• Melting Point: 166°C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.458g/cm³
• Refractive Index: 1.517
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 8.30±0.10(Predicted)
• CAS DataBase Reference: 5-HYDROXY-5-METHYLHYDANTOIN(CAS DataBase Reference)
• NIST Chemistry Reference: 5-HYDROXY-5-METHYLHYDANTOIN(10045-58-6)
• EPA Substance Registry System: 5-HYDROXY-5-METHYLHYDANTOIN(10045-58-6)

Safety Data

• Hazardous Substances Data: 10045-58-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-HYDROXY-5-METHYLHYDANTOIN is used as a synthetic intermediate for the development of new pharmaceutical compounds. Its ability to be modified and incorporated into more complex molecules makes it a valuable asset in the design and synthesis of novel drugs.
Used in Chemical Research:
5-HYDROXY-5-METHYLHYDANTOIN is used as a research compound in the field of organic chemistry. It serves as a model compound for studying various chemical reactions and mechanisms, contributing to the advancement of knowledge in this field.
Used in Material Science:
5-HYDROXY-5-METHYLHYDANTOIN can be used as a building block in the development of new materials with specific properties. Its incorporation into polymers or other materials can lead to the creation of materials with unique characteristics, such as improved stability or enhanced reactivity.
Used in Cosmetics Industry:
5-HYDROXY-5-METHYLHYDANTOIN may be used as an ingredient in the cosmetics industry, where it can serve as a component in the formulation of various cosmetic products. Its specific properties may contribute to the overall performance and efficacy of these products.

InChI:InChI=1/C4H6N2O3/c1-4(9)2(7)5-3(8)6-4/h9H,1H3,(H2,5,6,7,8)

Upstream product

• 26305-13-5 5,6-dimethyluracil 
• 71-30-7 Cytosine 
• 65-71-4 thymin 
• 77719-76-7 1-formyl-5-hydroxy-5-methylhydantoin 
• 127-17-3 2-oxo-propionic acid 
• 57-13-6 urea 

Relevant articles and documents

Synthesis and reactivity of 5-methylenehydantoins

5-Methylenehydantoin, as well as the N-mono- and N,N-di-protected derivatives, can be obtained by different synthetic routes. These compounds can undergo a large variety of reactions, such as Diels-Alder, epoxidation, methanol addition and conjugate addition reactions of different types of nucleophiles, including carbon (cyanide), nitrogen (piperidine) and sulfur (thiols, thioacetate) nucleophiles. The reactivity with electrophilic reagents, such as m-CPBA or methanol in acidic medium, and the need for Lewis acids to promote the conjugate addition reactions indicate that hydantoin is a poor electron-withdrawing group.

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.

The reactions of thymine and thymidine with ozone

The ozonolysis of thymine and thymidine has been investigated by a product study complemented by kinetic studies using spectrophotometry, conductometry and stopped-flow with optical and conductometric detection. Material balance has been obtained. Ozonolysis of thymine (k = 3.4 × 104 dm3 mol-1 s-1) leads to the formation of the acidic (pKa = 4) hydroperoxide 1-hydroperoxymethylene-3-(2-oxopropanoyl)urea 5 (～34%), neutral hydroperoxides (possibly mainly 1-hydroperoxyhydroxymethyl-3-(2-oxopropanoyl)urea 6, total ～41%) and H2O2 (25%, with corresponding formation of 1-formyl-5-hydroxy-5-methylhydantoin 11). The organic hydroperoxides decay (～1.1 × 10-3 s-1 at 20°C, 1.3 × 10-4 s-1 at 3°C) releasing formic acid (formation of 5-hydroperoxy-5-methylhydantoin 18) and also to some extent H2O2 (and 11). After 100 min, the formic acid yield is 75%. Upon treatment at high pH, it increases to 100%. Reduction of the organic hydroperoxides with bis(2-hydroxyethyl) sulfide (k = 50 dm3 mol-1 s-1) leads to 11 whose subsequent treatment with base yields 5-hydroxy-5-methylhydantoin 13 in 100% yield. It is suggested that the Criegee ozonide formed upon reaction with ozone at the C(5)-C(6) double bond opens heterolytically in two directions with subsequent opening of the C(5)-C(6) bond. In the preferred route (75%), the positive charge resides at C(6). Deprotonation at N(1) gives rise to 5, while its reaction with water yields 6. Loss of formic acid yields 5-hydroperoxy-5-methylhydantoin 18. Reduction of 5 and 6 with the sulfide yields 11. In the minor route (25%), the positive charge remains at C(5) followed by a reaction with water. The resulting α-hydroxy hydroperoxide rapidly loses H2O2 (formation of 11). In basic solution, singlet dioxygen is formed (8%). The concomitant product, 5,6-dihydroxy-5,6-dihydrothymine has been detected. In the ozonolysis of thymidine, the rapid formation of conductance (k = 0.55 s-1) is due to the release of acetic acid (18%). In this reaction a short-lived hydroperoxide is destroyed. As a consequence of this, 25 s after ozonolysis the total hydroperoxide yield is only ～78% (including 8% H2O2). The products corresponding to acetic acid are suggested to be CO2 and N-(2-deoxy-β-D-erythropentofuranosyl)formylurea 22. A number of organic hydroperoxides have been detected by HPLC by post-column derivatisation with iodide. An acidic hydroperoxide such as 5 in the case of thymine is not among the products. Upon sulfide reduction, the organic hydroperoxides yield mainly (43-50%) N1-(2-deoxy-β-D-erythropentofuranosyl)-5-hydroxy-5- methylhydantoin 23. The reasons for some striking differences in the ozonolyses of thymine and thymidine are discussed.

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.