487-21-8

Basic information

• Product Name: Lumazine
• Synonyms: LUMAZINE;2,4-PTERIDINEDIOL;2,4-HYDROXYPTERIDINE;2,4(1H,3H)-PTERIDINEDIONE;2,4-DIHYDROXYPTERIDINE;2,4-DIHYDROCYPTERIDINE;2,4(3H,8H)-Pteridinedione;Lumazin
• CAS NO: 487-21-8
• Molecular Formula: C₆H₄N₄O₂
• Molecular Weight: 164.12
• EINECS: 207-652-7
• Product Categories: Heterocycles;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Quinazolines
• Mol File: 487-21-8.mol

Chemical Properties

• Melting Point: 300 °C
• Boiling Point: 291.56°C (rough estimate)
• Flash Point: 287.1oC
• Appearance: yellow/crystalline
• Density: 1.5129 (rough estimate)
• Vapor Pressure: 9.33E-13mmHg at 25°C
• Refractive Index: 1.6900 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly)
• PKA: pK1:<1.3;pK2:7.92 (25°C)
• Water Solubility: 0.125 g/100 mL (25 ºC)
• Merck: 14,5596
• BRN: 157503
• CAS DataBase Reference: Lumazine(CAS DataBase Reference)
• NIST Chemistry Reference: Lumazine(487-21-8)
• EPA Substance Registry System: Lumazine(487-21-8)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: UO3416000
• TSCA: Yes
• Hazardous Substances Data: 487-21-8(Hazardous Substances Data)

Usage

Uses

Used in Analytical Chemistry:
Lumazine is used as a new MALDI (Matrix-Assisted Laser Desorption/Ionization) matrix for the analysis of complex (phospho)lipid mixtures. Its ability to enhance the ionization process and improve the detection of these mixtures makes it a valuable tool in the field of analytical chemistry, particularly for researchers studying lipid biochemistry and related areas.
Used in Pharmaceutical Industry:
Lumazine, due to its chemical properties, can be utilized in the development of pharmaceutical compounds. Its potential applications in drug discovery and design can contribute to the creation of novel therapeutic agents, targeting various health conditions and diseases.
Used in Research and Development:
In the realm of research and development, Lumazine can be employed as a key component in the synthesis of other bioactive molecules or as a starting material for the development of new chemical entities with potential applications in various fields, including medicine, agriculture, and environmental science.

Purification Methods

Crystallise the dione from water. It has also been purified as for pterin below. [Dallacker & Steiner Justus Liebigs Ann Chem 660 98 1962, Beilstein 26 III/IV 2489.]

InChI:InChI=1/C6H4N4O2/c11-5-3-4(8-2-1-7-3)9-6(12)10-5/h1-2H,(H2,8,9,10,11,12)

Upstream product

• 3240-72-0 5,6-diaminouracil 
• 517-21-5 glyoxal sodium bisulfite 
• 6164-78-9 pyrazine-2,3-dicarboxamide 
• 2236-60-4 2-aminopteridin-4(3H)-one 
• 22005-65-8 Isopterin 
• 13300-40-8 8-(2-Hydroxyethyl)-lumazin 
• 700-47-0 pteridin-4-one 
• 7647-01-0 hydrogenchloride 
• 1127-93-1 2,4-diaminopteridin 
• 131543-46-9 Glyoxal 
• 7732-18-5 water 
• 5424-01-1 3-aminopyrazinoic acid 
• 57-13-6 urea 
• 142645-43-0 2-pivaloylaminopteridin-4(3H)-one 

Downstream Products

• 5049-61-6 2-Aminopyrazine 
• 20737-42-2 3-oxo-3,4-dihydropyrazine-2-carboxylic acid 
• 5424-01-1 3-aminopyrazinoic acid 
• 94591-35-2 1,3-Dibenzyllumazin 
• 159228-08-7 1-(2-O-acetyl-3,5-di-O-benzoyl-β-D-threo-pentofuranosyl)-lumazine 
• 35777-63-0 1-[O³,O⁵-bis-(4-methyl-benzoyl)-α-L-erythro-2-deoxy-pentofuranosyl]-1H-pteridine-2,4-dione 
• 50256-05-8 1-[O³,O⁵-bis-(4-methyl-benzoyl)-β-D-erythro-2-deoxy-pentofuranosyl]-1H-pteridine-2,4-dione 
• 34097-18-2 1-(tri-O-benzoyl-β-D-ribofuranosyl)-1H-pteridine-2,4-dione 
• 159228-11-2 2,2'-anhydro-1-(3,5-di-O-benzoyl-β-D-lyxofuranosyl)-lumazine 
• 159228-09-8 1-(3,5-di-O-benzoyl-β-D-xylofuranosyl)-lumazine 
• 159228-10-1 1-(3,5-di-O-benzoyl-2-O-mesyl-β-D-xylofuranosyl)-lumazine 
• 159228-14-5 1-(3,5-di-O-benzoyl-2-O-phenoxythiocarbonyl-β-D-xylofuranosyl)-lumazine 
• 92982-89-3 2,2'-anhydro-3-(5-O-trityl-β-D-arabinofuranosyl)lumazine 
• 92982-81-5 3-(5-O-trityl-β-D-ribofuranosyl)lumazine 

Relevant articles and documents

Preparation method of heterocyclicpyrimidinedione compound

The invention discloses a preparation method of a heterocyclicpyrimidinedione compound and relates to the technology of medicinal chemistry. The preparation method comprises the following steps: 1) mixing an o-amino formonitrile heterocyclic compound and a catalyst to form a mixture, wherein the catalyst is [HDBN][TFE]; 2) in a CO2 environment, heating the mixture and reacting; 3) when the temperature is reduced to room temperature, adjusting the pH value to neutrality, and extracting, separating and collecting the an organic phase; drying, filtering and then vaporizing; performing column chromatography separation to obtain the heterocyclicpyrimidinedione compound. The preparation method disclosed by the invention has the advantages of low cost, environmental friendliness, simple preparation process and wide application range of substrate.

Ionic liquid promoted synthesis of heterocycle-fused pyrimidine-2,4(1H,3H)-diones utilising CO2

An efficient ionic liquid system was developed for the preparation of various heterocycle-fused pyrimidine-2, 4(1H,3H)-diones in moderate to excellent yields (52–95%). It was found that [HDBN+][TFE?], a simple and easily prepared ionic liquid, could act as both the solvent and reaction promoter, and that the reactions could be efficiently carried out at atmospheric pressures of CO2.

Evaluation of liquid chromatographic behavior of lumazinic derivatives, from α-dicarbonyl compounds, in different c18 columns: Application to wine samples using a fused-core column and fluorescence detection

Several C18 columns, packed with totally porous particles of different sizes and shell thicknesses, have been compared for simultaneous determination of α-dicarbonyl compounds, previous derivatization to lumazinic derivatives. Chromatographic conditions for the separation have been optimized for each column, and chromatographic parameters have been calculated and exhaustively compared. A core-shell C18 column provided the best results, and a HPLC method with fluorimetric detection has been proposed. The developed method has been validated in terms of linearity, precision, and sensitivity. Detection and quantification limits obtained were comprised between 0.02 and 0.30 and 0.07 and 1.0 ng mL-1, respectively, while RSD values obtained were lower than 6% and 5% in intraday and interday repeatability studies, respectively. The method has been applied to analysis of the α-dicarbonyl compounds in different types of wines. The higher levels of the total α-dicarbonyl compounds were found in sweet wines and the lower levels in white wines.

One-step synthesis of lumazine and xanthine: First co-crystal of lumazine and perchloric acid with a unique monohydrated hydronium ion (H 5O2+) mediated supramolecular assembly of the lumazine dimer

A perchloric acid mediated one-step synthesis of lumazine derivatives from pterins and xanthine from guanine is reported. However, 2-pivaloylamino derivatives of pterins underwent simple hydrolysis of the pivaloylamino group generating free pterin compounds, but the 2-oxo derivatives, that is, the lumazine compounds, were not obtained. A novel supramolecular assembly is constructed by the unique hydrogen bonding of H5O2 + bridging two hydrogen-bonded dimers of lumazine to form the co-crystal 21 with aqueous perchloric acid. In contrast, N2-pivaloyl- 6-bromo-5-deazapterin was simply hydrolysed to form the protonated deazapterin 22, which forms a unique six-membered cyclic hydrogen-bonded structure leading to the generation of a polymeric supramolecular assembly. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

A green, facile, and one-pot synthesis of 2,4-(1H,3H)-quinazolinediones under microwave irradiations

Quinazoline-2,4-diones are of considerable interest due to their wide pharmacological properties. Here, we have described an environmentally friendly method for the one-pot synthesis of 2,4-(1H,3H)-quinazolinediones from the reaction of anthranilic acid derivatives with urea in H2O media under microwave irradiations. This method is simple, safe, and fast which produces high yield of products without use of any catalyst. Copyright

The Oxidation of 6- and 7-Aryl-4(3H)-pteridinones by Immobilized Arthrobacter M-4 Cells Containing Xanthine Oxidase

The preparation of 6- and 7-(pX-phenyl)-4(3H)-pteridinones (X = H, CH3, OCH3) is described.The oxidation of these compounds by (immobilized) Arthrobacter M-4 cells containing xanthine oxidase has been studied.The oxidation monitored by uv spectroscopy usually goes fast, except for 7-(pX-phenyl)-4(3H)-pteridinones (X = CH3, OCH3), which are slowly oxidized.With bacterial cells immobilized in gelatine crosslinked with glutaraldehyde small laboratory-scale oxidations were carried out.Based on spectral data the products of the oxidation reactions are 6- and 7-aryllumazines.

Pteridines, LXXI. - Synthesis and Photochemical Behaviour of 8- Substituted Lumazines

The 8-substituted lumazines 34-69 have been synthesized from 6-chloro-5-nitrouracil (1) and its 3-methyl derivative 2 via the corresponding 6-amino-5-nitrouracils 3-26, substituted at the amino nitrogen.The photochemical properties of the 8-substituted lumazines have been investigated.Various photoreactions were observed depending on the chemical nature of the N-8-side-chain and leading to an easy photodealkylation of the β-hydroxy-, β-methoxy-, and β-aminoethyl derivatives 34-44.Increasing donor properties of the β-substituent enhances the photolability which is expressed in a Norrish-type II cleavage reaction to the corresponding lumazines 70-75. 8-Cycloalkyllumazines 52-54 show photoreduction to 7,8-dihydrolumazines 76-78.The newly synthesized 8-substituted lumazine derivatives have been characterized by elementary analyses and UV spectra.Structural peculiarities due to the various substituents in position 6, 7, and 8 will be discussed.

Azaisatoic anhydrides

A method for producing heterocyclic acid anhydrides and pyrimidinediones from the corresponding acids, dicarboxamides, 2,3-and 3,4-pyridinedicarboxamides, and N-monosubstituted 2,3-and 3,4-pyridinedicarboxamides, in which the aforesaid compounds are reacted with lead tetra-acetate in the presence of a suitable anhydrous inert solvent.