N-Isopentenyladenosine

Base Information

• Chemical Name: N-Isopentenyladenosine
• CAS No.: 7724-76-7
• Molecular Formula: C₁₅H₂₁N₅O₄
• Molecular Weight: 335.363
• Hs Code.: 29400090
• NSC Number: 105546
• Wikidata: Q104667557
• Mol file: 7724-76-7.mol

Synonyms:N6-2-Isopentenyladenosine;Dimethylallyladenosine;NSC105546;N6-(.DELTA.2-Isopentenyl)adenosine;N6-Isopentenyladenosine;SQ 22,558;Isopentenyl adenine riboside;6-(.gamma.,.gamma.-Dimethylallylamino)purine riboside;9.beta.-D-Ribofuranosyl-9H-purine, N-(3-methyl-2-butenylamino)-;SQ 22558;ZK 20 242;MFCD00005741;SCHEMBL4600;6-N-[(3-Methyl-2-butenyl)amino]-9.beta.-D-ribofuranosylpurine;SB19217;SY077310;FT-0636577;6-(3,3-Dimethylallylamino)-9-(beta-D-ribofuranosyl)purine;WLN: T56 BN DN FN HNJ IM2UY1&1 D- BT5OTJ CQ DQ E1Q;{6-N-[(3-Methyl-2-butenyl)amino]-9.beta.-D-ribofuranosylpurine};{6-N-[(3-Methyl-2-butenyl)amino]-9-.beta.-D-ribofuranosyl-9H-purine};2-(hydroxymethyl)-5-[6-(3-methylbut-2-enylamino)purin-9-yl]tetrahydrofuran-3,4-diol

Chemical Property of N-Isopentenyladenosine

Chemical Property:

• Melting Point: 142-143 °C(Solv: ethanol (64-17-5))
• Boiling Point: 647.2±65.0 °C(Predicted)
• PKA: 13.12±0.70(Predicted)
• PSA: 125.55000
• Density: 1.56±0.1 g/cm3(Predicted)
• LogP: -0.11110
• Storage Temp.: −20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 335.15935417
• Heavy Atom Count: 24
• Complexity: 461

Purity/Quality:

98%min ^*data from raw suppliers

N6-Isopentenyladenosine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCNC1=C2C(=NC=N1)N(C=N2)C3C(C(C(O3)CO)O)O)C
• Description: N6-(Δ2-Isopentenyl)adenosine is a precursor in the biosynthesis of the plant hormone N6-(Δ2-isopentenyl)adenine . N6-(Δ2-isopentenyl)adenine may be converted to the cytokinin trans-zeatin by cytochrome P450 mono-oxygenases. Cytokinins, including N6-(Δ2-isopentenyl)adenine and trans-zeatin, regulate diverse events in plant growth and development. N6-(Δ2-Isopentenyl)adenosine can also alter post-transcriptional processes in mammalian cells, altering proliferation and apoptosis.
• Uses: [2H6] N6-Isopentenyladenosine-D6 can be used as analyte in analytical study for acetylation of cytokinins and modified adenine compounds for gas chromatography-mass spectrometric analysis. N6-Isopentenyladenosine has antiproliferative activity on MCF-7 breast cancer cells.

Technology Process of N-Isopentenyladenosine

There total 23 articles about N-Isopentenyladenosine 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: 54.0%

1-N-(3-methyl-2-buten-1-yl)-N6-acetyl-2',3',5'-tri-O-acetyladenosine → 6-N-(2-isopentenyl)adenosine (7724-76-7,33156-15-9)

Guidance literature:

1-N-(3-methyl-2-buten-1-yl)-N⁶-acetyl-2',3',5'-tri-O-acetyladenosine; With ammonia; In methanol; at 20 ℃; for 120h;

With ammonium hydroxide; at 20 ℃; for 168h;

DOI:10.1080/15257770.2015.1016169

Reference yield: 33.0%

N6-acetyl-N6-isopentenyl-2',3',5'-tri-O-acetyladenosine (1338578-80-5) → 6-N-(2-isopentenyl)adenosine (7724-76-7,33156-15-9)

Guidance literature:

With ammonia; In methanol; at 20 ℃; for 48h;

DOI:10.1016/j.ejmech.2014.11.048

Reference yield:

1-N-(3-methyl-2-buten-1-yl)-2',3',5'-tri-O-acetyladenosine → 6-N-(2-isopentenyl)adenosine (7724-76-7,33156-15-9)

Guidance literature:

With ammonium hydroxide; at 20 ℃; for 168h;

DOI:10.1080/15257770.2015.1016169

upstream raw materials:

trans-zeatin 9-β-D-riboside O-β-D-glucopyranoside

prenyl bromide

adenosine

6-(2-isopentenyl)adenosine 5'-monophosphate

Downstream raw materials:

N₆-(2-isopentenyl)adenine

α-D-ribofuranosyl-1-phosphate

trans-zeatin 9-β-D-ribofuranoside

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

Refernces

• 1、 Orlov, Alexey A.,Drenichev, Mikhail S.,Oslovsky, Vladimir E.,Kurochkin, Nikolay N.,Solyev, Pavel N.,Kozlovskaya, Liubov I.,Palyulin, Vladimir A.,Karganova, Galina G.,Mikhailov, Sergey N.,Osolodkin, Dmitry I.. "New tools in nucleoside toolbox of tick-borne encephalitis virus reproduction inhibitors". supporting information. p. 1267 - 1273. Retrieved 2017/06/19.
• 2、 Oslovsky, Vladimir E.,Drenichev, Mikhail S.,Mikhailov, Sergey N.. "Regioselective 1-N-Alkylation and rearrangement of adenosine derivatives". . p. 475 - 499. Retrieved 2015/10/19.