19342-73-5

Basic information

• Product Name: 5-deazariboflavin
• Synonyms: 5-deazariboflavin;1-Deoxy-1-(3,4-dihydro-7,8-dimethyl-2,4-dioxopyrimido[4,5-b]quinolin-10(2H)-yl)-D-ribitol;5-Carbariboflavin;7,8-Dimethyl-10-(1-deoxy-D-ribitol-1-yl)-2,3,4,10-tetrahydropyrimido[4,5-b]quinoline-2,4-dione
• CAS NO: 19342-73-5
• Molecular Formula: C₁₈H₂₁N₃O₆
• Molecular Weight: 375.37584
• Product Categories: Aromatics, Heteroctcles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 19342-73-5.mol
• Article Data: 6

Chemical Properties

• Melting Point: 278-282 °C(Solv: water (7732-18-5))
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.57g/cm³
• Refractive Index: 1.703
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Aqueous Base (Slightly), DMSO (Slightly)
• PKA: 5.79±0.20(Predicted)
• CAS DataBase Reference: 5-deazariboflavin(CAS DataBase Reference)
• NIST Chemistry Reference: 5-deazariboflavin(19342-73-5)
• EPA Substance Registry System: 5-deazariboflavin(19342-73-5)

Safety Data

• Hazardous Substances Data: 19342-73-5(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 19342-73-5 differently. You can refer to the following data:
1. 1-Deazariboflavin, is the derivative of (-)-Riboflavin (R414995), known as vitamin B2 . 5-Deazariboflavin,is also utilized in photosensitized cleavage of thymine dimer, used in the study of the action of photoreactivation enzymes. It is also used in synthesis of 5-deazaflavin adenine dinucleotide (5-dFAD).
2. 1-Deazariboflavin, is the derivative of (-)-Riboflavin (R414995), known as vitamin B2 .5-Deazariboflavin,is also utilized in photosensitized cleavage of thymine dimer, used in the study of the action of photoreactivation enzymes. It is also used in synthesis of 5-deazaflavin adenine dinucleotide (5-dFAD).

InChI:InChI=1/C18H21N3O6/c1-8-3-10-5-11-16(19-18(27)20-17(11)26)21(12(10)4-9(8)2)6-13(23)15(25)14(24)7-22/h3-5,13-15,22-25H,6-7H2,1-2H3,(H,20,26,27)/t13-,14+,15-/m0/s1

Upstream product

• 3051-94-3 3,4-dimethyl-N-ribitylaniline 
• 111619-05-7 3,4-xylidino-D-ribofuranoside 
• 95-64-7 4-amino-o-xylene 
• 36468-53-8 β-D-ribofuranose 
• 36995-92-3 6-uracil 
• 59389-71-8 6-uracil 
• 50-69-1 D-ribose 
• 59389-72-9 2',3',4',5'-tetra-O-acetyl-5-deazariboflavin 

Downstream Products

• 36408-16-9 7,8-dimethyl-10-(5-phosphono-L-ribitol-1-yl)-10H-pyrimido[4,5-b]quinoline-2,4-dione 
• 57818-88-9 5-deazaflavin adenine dinucleotide 

Related news

Absolute rate constants for 5-deazariboflavin (cas 19342-73-5) triplet excited state in one-electron transfer processes08/02/2019

Laser-flash photolysis was employed to determine absolute rate constants for quenching of 5-deazariboflavin triplet excited state by amines and phenols in methanol solution. The observed reactivity order for triplet quenching by aliphatic amines parallels very well the corresponding trend in oxi...detailed

Relevant articles and documents

Deazaflavins as photocatalysts for the direct reductive regeneration of flavoenzymes

Deazaflavins are potentially useful redox mediators for the direct, nicotinamide-independent regeneration of oxidoreductases. Especially the O2-stability of their reduced forms have attracted significant interest for the regeneration of monooxygenases. In this contribution we further investigate the photochemical properties of deazaflavins and investigate the scope and limitations of deazaflavin-based photoenzymatic reaction systems.

Synthesis and electrochemical properties of structurally modified flavin compounds

Four structurally modified flavin compounds have been synthesized and characterized for their redox potential by chemical reduction with sodium dithionite. Besides the previously reported 1- and 5-deazariboflavin, a 7,8-didemethyl derivative and an 8-isopropylriboflavin have been obtained. The synthesis of these compounds started in all cases from appropriately substituted anilines that were condensed with the ribityl chain, followed by completion of the annealed three-ring structure. The didemethyl- and the isopropyl compounds gave absorption maxima similar to riboflavin (436 and 448 nm, respectively), whereas 1-deazariboflavin showed a bathochromically shifted absorption (λmax = 537 nm), and that of 5-deazariboflavin was hypsochromically shifted (λmax = 400 nm). The midpoint potentials (E0′) of the four modified flavin compounds were determined by potentiometric titration, using riboflavin as a reference compound. Both alkyl-modified flavins showed slightly less negative midpoint potentials, whereas both deaza compounds had more negative midpoint values compared to the reference compound. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Synthesis of 5-deazaflavin adenine dinucleotide (5-dFAD) using a modified triester approach

Starting from D-ribose and 3,4-xylidine, a fifteen-step synthesis is described for the preparation of 5-dFAD (18).The synthesis involves as key intermediates, 5-deazariboflavin (8), its 2',3',4'-tris-O-(tetrahydropyranyl) derivative (12) and 2',3',4'-tris-O-(tetrahydropyranyl)-5'-O-(morpholinophosphonyl)-5-deazaribolavin (15).