8-Hydroxyadenine

Base Information

• Chemical Name: 8-Hydroxyadenine
• CAS No.: 21149-26-8
• Molecular Formula: C5H5 N5 O
• Molecular Weight: 151.128
• Hs Code.: 2933990090
• NSC Number: 24123
• DSSTox Substance ID: DTXSID70175390
• Nikkaji Number: J442.510C
• Wikidata: Q83045715
• Metabolomics Workbench ID: 37301
• ChEMBL ID: CHEMBL150192
• Mol file: 21149-26-8.mol

Synonyms:7,8-DHOA;7,8-dihydro-8-oxoadenine;8-hydroxyadenine;8-oxoadenine

Chemical Property of 8-Hydroxyadenine

Chemical Property:

• Vapor Pressure: 0.112mmHg at 25°C
• Melting Point: >320 °C (decomp)
• Boiling Point: 220.7°Cat760mmHg
• PKA: 7.27±0.40(Predicted)
• Flash Point: 87.3°C
• PSA: 100.45000
• Density: 1.577g/cm³
• LogP: -0.19040
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility.: Aqueous Acid (Slightly), Chloroform (Slightly), DMSO (Slighty, Heated, Sonicated
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 151.04940980
• Heavy Atom Count: 11
• Complexity: 184

Purity/Quality:

99% ^*data from raw suppliers

8-Hydroxy Adenine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC(=C2C(=N1)NC(=O)N2)N
• Uses: 8-Hydroxyadenine is an adenine metabolite, which can be used as a plant growth regulator.

Technology Process of 8-Hydroxyadenine

There total 2 articles about 8-Hydroxyadenine 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:

phosmidosine → 8-oxoadenine (21149-26-8) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7)

Guidance literature:

With hydrogenchloride; at 110 ℃; for 16h;

DOI:10.1021/jo00056a017

Reference yield:

adenine (66224-66-6,66224-67-7,66224-68-8,66224-69-9,134434-48-3,134434-49-4,134454-76-5,134461-75-9) → N-(4,6-diaminopyrimidin-5-yl)formamide (5122-36-1) + 8-Hydroxyadenine (21149-26-8)

Guidance literature:

With water; dinitrogen monoxide; at 20 ℃; Rate constant; Thermodynamic data; Mechanism; van de Graaff accelerator pulsation, product yield/distribution, E_A, ΔS, log A, var. oxidizing or reducing agents; other 9-substituted adenine derivatives;

DOI:10.1021/ja00175a036

Reference yield: 52.0%

8-oxoadenine (21149-26-8) + (S)-tritylglycidol (129940-50-7) → (S)-6-Amino-9-[2-hydroxy-3-(trityloxy)propyl]-7H-purin-8(9H)-one (303014-70-2) + 6-Amino-7,9-bis[(2S)-2-hydroxy-3-(trityloxy)propyl]-7H-purin-8(9H)-one (303014-71-3)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 110 ℃; for 25h;

DOI:10.1135/cccc20001126

upstream raw materials:

adenine

Downstream raw materials:

(S)-6-Amino-9-[2-hydroxy-3-(trityloxy)propyl]-7H-purin-8(9H)-one

6-Amino-7,9-bis[(2S)-2-hydroxy-3-(trityloxy)propyl]-7H-purin-8(9H)-one

6-amino-9-(cyclohexylmethyl)-7H-purin-8(9H)-one

6-amino-9-benzyl-7H-purin-8(9H)-one

Refernces

• 1、 Phillips, Dennis R.,Uramoto, Masakazu,Isono, Kiyoshi,McCloskey, James A.. "Structure of the Antifungal Nucleotide Antibiotic Phosmidosine". . p. 854 - 859. Retrieved 2007/10/02.