N-((2-hydroxyphenyl)methyl)adenosine

Base Information

• Chemical Name: N-((2-hydroxyphenyl)methyl)adenosine
• CAS No.: 50868-58-1
• Molecular Formula: C17H19 N5 O5
• Molecular Weight: 373.368
• UNII: 3O1XLV8S38
• DSSTox Substance ID: DTXSID4042173
• Nikkaji Number: J815.795B
• Wikidata: Q27893177
• Mol file: 50868-58-1.mol

Synonyms:6-(2-hydroxybenzylamino)-9-beta-D-ribofuranosylpurine;6-HBARP;spathe regreening factor

Chemical Property of N-((2-hydroxyphenyl)methyl)adenosine

Chemical Property:

• Vapor Pressure: 6.15E-23mmHg at 25°C
• Boiling Point: 739.1°Cat760mmHg
• PKA: 9.84±0.30(Predicted)
• Flash Point: 400.8°C
• PSA: 145.78000
• Density: 1.71g/cm³
• LogP: -0.17150
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 5
• Exact Mass: 373.13861872
• Heavy Atom Count: 27
• Complexity: 502

Purity/Quality:

97% ^*data from raw suppliers

ortho-Topolin Riboside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)CNC2=C3C(=NC=N2)N(C=N3)C4C(C(C(O4)CO)O)O)O
• Isomeric SMILES: C1=CC=C(C(=C1)CNC2=C3C(=NC=N2)N(C=N3)[C@H]4[C@@H]([C@@H]([C@H](O4)CO)O)O)O
• Uses: ortho-Topolin Riboside can be utilized in biological study where antagonistic roles of abscisic acid and cytokinin including meta-Topolin 9-Glucoside are significantly involved in response to nitrogen depletion which enhances biomass and biofuel productivity.

Technology Process of N-((2-hydroxyphenyl)methyl)adenosine

There total 4 articles about N-((2-hydroxyphenyl)methyl)adenosine 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:

6-Chloropurine riboside (2004-06-0) + o-hydroxyphenylmethylamine hydrochloride (61626-91-3) → 6-(2-hydroxybenzyl)adenosine (50868-58-1)

Guidance literature:

With triethylamine; In propan-1-ol; at 70 ℃; for 8h;

Reference yield:

salicylaldehyde-oxime (94-67-7) → 6-(2-hydroxybenzyl)adenosine (50868-58-1)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / ethanol; water / 760.05 Torr

2: triethylamine / propan-1-ol / 8 h / 70 °C

With hydrogenchloride; hydrogen; triethylamine; palladium 10% on activated carbon; In propan-1-ol; ethanol; water;

Reference yield:

o-topolin (20366-83-0) + 7-methylguanosine (22164-16-5) → 6-(2-hydroxybenzyl)adenosine (50868-58-1)

Guidance literature:

With dipotassium hydrogenphosphate; purine nucleotide phosphorylase; In ethanol; water; at 35 ℃; Enzymatic reaction;

DOI:10.1002/jlcr.3702

upstream raw materials:

6-Chloropurine riboside

o-hydroxyphenylmethylamine hydrochloride

salicylaldehyde-oxime

2-methoxybenzylamine

Refernces

• 1、 -. "APPLICATIONS OF N6-SUBSTITUTED ADENOSINE DERIVATIVE AND N6-SUBSTITUTED ADENINE DERIVATIVE TO CALMING, HYPNOSES, CONVULSION RESISTANCE, EPILEPTIC RESISTANCE, PARKINSON DISEASE RESISTANCE, AND DEMENTIA PREVENTION AND TREATMENT". Paragraph 0095. . Retrieved 2018/10/27.
• 2、 Starha, Pavel,Popa, Igor,Travnicek, Zdenek,Vanco, Jan. "N6-benzyladenosine derivatives as novel n-donor ligands of platinum(ii) dichlorido complexes". . p. 6990 - 7003. Retrieved 2013/07/26.