504-07-4

Basic information

• Product Name: 5,6-DIHYDROURACIL
• Synonyms: TIMTEC-BB SBB007702;2,4(1H,3H)-Pyrimidinedione, dihydro-;3h)-pyrimidinedione,dihydro-4(1h;Dihydro-pyrimidine-2,4-dione;Hydrouracil;5,6-DIHYDROURACIL;5,6-DIHYDRO-2,4-DIHYDROXYPYRIMIDINE;DIHYDRO-2,4(1H,3H)-PYRIMIDINEDIONE
• CAS NO: 504-07-4
• Molecular Formula: C4H6N2O2
• Molecular Weight: 114.1
• EINECS: 207-982-1
• Product Categories: Nucleic acids;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 504-07-4.mol
• Article Data: 25

Chemical Properties

• Melting Point: 279-281 °C(lit.)
• Boiling Point: 213.59°C (rough estimate)
• Flash Point: °C
• Appearance: /
• Density: 1.3565 (rough estimate)
• Refractive Index: 1.4487 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Soluble in Sodium Hydroxide.
• PKA: 12.10±0.20(Predicted)
• BRN: 112496
• CAS DataBase Reference: 5,6-DIHYDROURACIL(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-DIHYDROURACIL(504-07-4)
• EPA Substance Registry System: 5,6-DIHYDROURACIL(504-07-4)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 504-07-4(Hazardous Substances Data)

Usage

Description

5,6-Dihydrouracil (DiHU) is a minor base found in transfer ribonucleic acid (tRNA), characterized by its white to light beige crystalline powder appearance. It is structurally similar to uracil, with the key difference being the saturation of the C5-C6 bond. DiHU has been studied for its crystalline structure and is known to be generated from L-cysteine and uracil through photochemical addition.

Uses

Used in Biochemical Research:
5,6-Dihydrouracil is used as a standard for the ureido group in the colorimetric assay of transfer ribonucleic acid (tRNA), aiding in the analysis and quantification of tRNA in various biological samples.
Used in Pharmaceutical Industry:
5,6-Dihydrouracil acts as an intermediate in the catabolism of uracil, a process that is essential for the synthesis and breakdown of nucleic acids. This makes it a valuable compound in the development of drugs targeting nucleic acid metabolism and related pathways.
Used in Impurity Analysis:
In the pharmaceutical industry, DiHU is also recognized as an impurity of uracil. Understanding and controlling the presence of this impurity is crucial for ensuring the purity and efficacy of uracil-based drugs and therapies.
Used in Analytical Chemistry:
The crystalline structure of 5,6-dihydrouracil has been analyzed, making it a subject of interest in analytical chemistry. Its unique properties and structure can be utilized for the development of new analytical methods and techniques in the study of nucleic acids and their derivatives.

InChI:InChI=1/C4H6N2O2/c7-3-1-2-5-4(8)6-3/h1-2H2,(H2,5,6,7,8)

Upstream product

• 5366-11-0 2-Thiouracil 
• 1600-27-7 mercury(II) diacetate 
• 64-19-7 acetic acid 
• 61066-33-9 pyrimidine-2,4,5,6(1H,3H)-tetraone 
• 444-15-5 5-hydroxybarbituric acid 
• 462-88-4 N-carbamoyl-β-alanine 
• 110-14-5 butanediamide 
• 71-30-7 Cytosine 
• 66-22-8 uracil 
• 57-13-6 urea 
• 79-10-7 acrylic acid 
• 97838-64-7 N¹-Iodomethyl-5,6-dihydrouracil 
• 67-52-7 BARBITURIC ACID 
• 67-56-1 methanol 

Downstream Products

• 462-88-4 N-carbamoyl-β-alanine 
• 66-22-8 uracil 
• 57-13-6 urea 
• 75500-04-8 1,3-dibenzyldihydropyrimidine-2,4(1H,3H)-dione 
• 56-41-7 L-alanin 
• 4433-22-1 2,4-dioxopyrimidine 
• 67-52-7 BARBITURIC ACID 
• 1194-23-6 5,6-dihydro-6-hydroxyuracil 
• 75500-05-9 N¹,N³-Dibenzyloxymethyl-5,6-dihydrouracil 
• 97838-63-6 N¹-Benzyloxymethyl-5,6-dihydrouracil 
• 89003-40-7 3-(1,2,3,4-tetrahydroisoquinolin-2-ylmethyl)dihydrouracil 

Relevant articles and documents

Photoinduced reduction of thymine and uracil derivatives by hypophosphite: Unusual high quantum yield of chromophore loss

The quantum yield of chromophore loss of thymine, uracil and their corresponding nucleosides and nucleoside-5′-monophosphates undergoing irradiation with 254 nm UV light was found to be sharply enhanced by hypophosphite; thymine and uracil were reduced by hypophosphite to give 5,6-dihydrothymine and 5,6-dihydrouracil respectively.

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4,5-Dihydroxyimidazolidin-2-ones in the α-ureidoalkylation reaction of N-(carboxyalkyl)-, N-(hydroxyalkyl)-, and N-(aminoalkyl)ureas 1. α-Ureidoalkylation of N-(carboxyalkyl)ureas

The α-ureidoalkylation of N-(carboxyalkyl)ureas (ureido acids) with 1,3-H2 s-, 1,3-Me 2 s-, and 1,3-Et2 s-4,5-dihydroxyimidazolidin-2-ones was systematically studied. The yields of glycolur

A uracil green production process

The present invention provides a uracil green production process, comprising the following steps: 1) to thio uracil as raw materials, adding water, also adding halide or sulfonic acid compound, heating overnight, cooling, filtering and drying, to obtain high-purity uracil; 2) step 1) filtering the resulting stock solution continue adding thio uracil, heating, circulating the above-mentioned operation. The invention has the following advantages: the reaction mother liquor and material can be applied mechanically, and yield and purity is not affected, is a environmental friendly technology. High purity can be obtained uracil, namely detection HPLC purity of 95% or more, or even 98% or more of the uracil.

Regioselective reactions of N-(carboxyalkyl)- and N-(aminoethyl)ureas with glyoxal and 1,2-dioxo-1,2-diphenylethane

Regioselective reactions of N-(carboxyalkyl)ureas (ureido acids) and N-(aminoethyl)ureas with 1,2-dioxo-1,2-diphenylethane (benzyl) and glyoxal are studied in detail. The structure of the reactants affects the reaction regioselectivity. Acid-catalyzed rea