Zeatin riboside

Base Information

• Chemical Name: Zeatin riboside
• CAS No.: 6025-53-2
• Molecular Formula: C15H21N5O5
• Molecular Weight: 351.362
• Hs Code.: 29349990
• UNII: 7LG4D082A9
• DSSTox Substance ID: DTXSID101017776
• Nikkaji Number: J1.274.243F,J120.777F
• Wikidata: Q27139815
• Metabolomics Workbench ID: 65865
• Mol file: 6025-53-2.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:

• Appearance/Colour: white to off-white crystalline powder
• Vapor Pressure: 4.42E-27mmHg at 25°C
• Melting Point: 176-179 °C
• Refractive Index: 1.728
• Boiling Point: 731.8 °C at 760 mmHg
• PKA: 13.11±0.70(Predicted)
• Flash Point: 396.4 °C
• PSA: 145.78000
• Density: 1.65 g/cm³
• LogP: -1.13870
• Storage Temp.: −20°C
• Solubility.: acetic acid: 50 mg/mL, clear, colorless
• Water Solubility.: slightly soluble
• 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:

99% ^*data from raw suppliers

trans-Zeatin riboside ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

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: A well-known, highly active stimulant of cell divisions in plant tissue cultures trans-Zeatin-riboside is used in tissue culture systems include control of shoot growth and formation, cell division and inhibition of leaf senescence. Cytokinins promote cell division, stimulate shoot proliferation, inhibit root formation, slow the aging process, and activate gene expression and metabolic activity in general.

Technology Process of Zeatin riboside

There total 14 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:

N6-(2-isopentenyl)adenine (2365-40-4) → trans-zeatin 9-β-D-ribofuranoside (6025-53-2)

Guidance literature:

Multi-step reaction with 3 steps

1: trimethylsilyl trifluoromethanesulfonate / acetonitrile / 18 h / Reflux

2: sodium methylate; methanol / 6 h / 20 °C

3: Salmonella typhimurium O₂-dependent tRNA modifying monooxgenase; dihydrogen peroxide / dimethyl sulfoxide / 1 h / 27 °C / pH 8 / Enzymatic reaction

With methanol; trimethylsilyl trifluoromethanesulfonate; Salmonella typhimurium O₂-dependent tRNA modifying monooxgenase; dihydrogen peroxide; sodium methylate; In dimethyl sulfoxide; acetonitrile; 1: |Vorbrueggen Nucleoside Synthesis;

DOI:10.1021/bi4000832

upstream raw materials:

Zeatin-9-beta-D-ribofuranoside 5'-monophosphate

(3-methyl-2-butenyl)amine hydrochloride

2,6 dichloropurine

(2-chloro-7⁽⁹⁾H-purin-6-yl)-(3-methyl-but-2-enyl)-amine

Downstream raw materials:

trans-zeatin

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