8-Hydroxy-5-deazaflavin

Base Information

• Chemical Name: 8-Hydroxy-5-deazaflavin
• CAS No.: 37333-48-5
• Molecular Formula: C16H17N3O7
• Molecular Weight: 363.327
• DSSTox Substance ID: DTXSID50958446
• Wikidata: Q77566840,Q110199950
• Metabolomics Workbench ID: 103535
• Mol file: 37333-48-5.mol

Synonyms:7,8-didemethyl-8-hydroxy-5-deazariboflavin;8-HDF cpd;8-hydroxy-5-deazaflavin;F(420);factor 420

Chemical Property of 8-Hydroxy-5-deazaflavin

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 169.16000
• Density: 1.7g/cm³
• LogP: -1.56910
• XLogP3: -3
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 363.10664989
• Heavy Atom Count: 26
• Complexity: 796

Purity/Quality:

99% ^*data from raw suppliers

CoenzymeFO 98.90% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=O)C=C2C1=CC3=C(N2CC(C(C(CO)O)O)O)NC(=O)NC3=O

Technology Process of 8-Hydroxy-5-deazaflavin

There total 17 articles about 8-Hydroxy-5-deazaflavin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

1-Deoxy-1-<(3-hydroxyphenyl)amino>-D-ribitol (71415-47-9) + 6-chloro-2,4-dioxohexahydropyrimidine-5-carbaldehyde (65644-24-8) → 8-hydroxy-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]pyrimido[4,5-b]quinoline-2,4(3H,10H)-dione (37333-48-5)

Guidance literature:

In N,N-dimethyl-formamide; for 3h; Heating;

DOI:10.1039/c39880000524

Reference yield: 83.0%

2,3:4,5-Bis-O-methoxymethylene-1-deoxy-1-(3,4-dihydro-8-hydroxy-2,4-dioxopyrimido<4,5-b>quinolin-10-(2H)-yl)-D-ribitol (71415-48-0) → 8-hydroxy-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]pyrimido[4,5-b]quinoline-2,4(3H,10H)-dione (37333-48-5)

Guidance literature:

With hydrogenchloride; In water; Heating;

DOI:10.1002/jhet.5570170813

Reference yield: 70.0%

2-chloro-4-hydroxybenzaldehyde (56962-11-9) + 1-deoxy-1-[(2,6-dioxo-1,2,3,6-tetrahydro-4-pyrimidinyl)amino]-D-ribitol (33106-48-8) → 8-hydroxy-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]pyrimido[4,5-b]quinoline-2,4(3H,10H)-dione (37333-48-5)

Guidance literature:

In N,N-dimethyl-formamide; for 3h; Heating;

DOI:10.1039/c39880000524

upstream raw materials:

2,3:4,5-Bis-O-methoxymethylene-1-deoxy-1-(3,4-dihydro-8-hydroxy-2,4-dioxopyrimido<4,5-b>quinolin-10-(2H)-yl)-D-ribitol

1-Deoxy-1-<(3-hydroxyphenyl)amino>-D-ribitol

6-chloro-2,4-dioxohexahydropyrimidine-5-carbaldehyde

2-chloro-4-hydroxybenzaldehyde

Refernces

• 1、 Decamps, Laure,Berteau, Olivier,Philmus, Benjamin,Begley, Tadhg P.,Benjdia, Alhosna,White, Robert. "Biosynthesis of F0, precursor of the F420 cofactor, requires a unique two radical-SAM domain enzyme and tyrosine as substrate". . p. 18173 - 18176,4. Retrieved 2012.
• 2、 Philmus, Benjamin,Decamps, Laure,Berteau, Olivier,Begley, Tadhg P.. "Biosynthetic versatility and coordinated action of 5′-deoxyadenosyl radicals in deazaflavin biosynthesis". supporting information. p. 5406 - 5413. Retrieved 2015/05/13.