Zeatin riboside

Base Information

• Chemical Name: Zeatin riboside
• CAS No.: 28542-78-1
• Molecular Formula: C₁₅H₂₁N₅O₅
• Molecular Weight: 351.362
• UNII: 7LG4D082A9
• DSSTox Substance ID: DTXSID101017776
• Nikkaji Number: J1.274.243F,J120.777F
• Wikidata: Q27139815
• Metabolomics Workbench ID: 65865
• Mol file: 28542-78-1.mol

Synonyms:N-(4-hydroxy-3-methyl-2-butenyl)adenosine;ribosylzeatin;zeatin riboside;zeatin riboside, (cis-(Z))-isomer;zeatin riboside, (E)-isomer

Chemical Property of Zeatin riboside

Chemical Property:

• Vapor Pressure: 1.77E-22mmHg at 25°C
• Melting Point: 176-179 °C
• Refractive Index: 1.728
• Boiling Point: 731.8°Cat760mmHg
• Flash Point: 396.4°C
• PSA: 145.78000
• Density: 1.65g/cm³
• LogP: -1.13870
• Storage Temp.: −20°C
• Solubility.: acetic acid: 50 mg/mL, clear, colorless
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 6
• Exact Mass: 351.15426879
• Heavy Atom Count: 25
• Complexity: 481

Purity/Quality:

98%, ^*data from raw suppliers

Zeatin riboside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCNC1=C2C(=NC=N1)N(C=N2)C3C(C(C(O3)CO)O)O)CO
• Isomeric SMILES: C/C(=C\CNC1=C2C(=NC=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)/CO
• Uses: Zeatin Riboside can be used for biological study in putative role of adenosine A3 receptor in anti-proliferative action of N6-(2-isopentyl)adenosine.

Technology Process of Zeatin riboside

There total 8 articles about Zeatin riboside 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: 44.0%

6-N-(3,3-dimethylallyl)adenosine (7724-76-7,33156-15-9) → 6-((E)-4-hydroxy-3-methylbut-2-enylamino)-9-β-D-ribofuranosylpurine (6025-53-2,15896-46-5,28542-78-1,91928-28-8,91928-29-9)

Guidance literature:

With tert.-butylhydroperoxide; selenium(IV) oxide; In dichloromethane; benzene; at 32 ℃;

DOI:10.1016/S0040-4039(00)86749-0

Reference yield: 38.0%

6-((E)-4-hydroxy-3-methylbut-2-enylamino)-9-β-D-ribofuranosylpurine (6025-53-2,15896-46-5,28542-78-1,91928-28-8,91928-29-9) → 6-((Z)-4-hydroxy-3-methylbut-2-enylamino)-9-β-D-ribofuranosylpurine (6025-53-2,15896-46-5,28542-78-1,91928-28-8,91928-29-9)

Guidance literature:

In ethanol; for 48h; Irradiation;

DOI:10.1016/S0040-4039(00)86749-0

Reference yield:

6-N-(3,3-dimethylallyl)adenosine (7724-76-7,33156-15-9) → 6-((Z)-4-hydroxy-3-methylbut-2-enylamino)-9-β-D-ribofuranosylpurine (6025-53-2,15896-46-5,28542-78-1,91928-28-8,91928-29-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 44 percent / SeO₂, ter-butyl hydroperoxide / benzene; CH₂Cl₂ / 32 °C

2: 38 percent / ethanol / 48 h / Irradiation

With tert.-butylhydroperoxide; selenium(IV) oxide; In ethanol; dichloromethane; benzene;

DOI:10.1016/S0040-4039(00)86749-0

upstream raw materials:

2,6 dichloropurine

2-methyl-4-(7⁽⁹⁾H-purin-6-ylamino)-but-2-en-1-ol

6-((E)-4-hydroxy-3-methylbut-2-enylamino)-9-β-D-ribofuranosylpurine

6-N-(3,3-dimethylallyl)adenosine

Downstream raw materials:

6-((Z)-4-hydroxy-3-methylbut-2-enylamino)-9-β-D-ribofuranosylpurine

Refernces

• 1、 David, Serge,Sennyey, Gerard de,Sotta, Bruno. "SIMPLE, INEXPENSIVE ROUTES TO E AND Z ZEATINE RIBOSIDES AND DERIVATIVES USEFUL FOR IMMUNOASSAY.". . p. 1817 - 1820. Retrieved 2007/10/02.