4338-48-1

Basic information

• Product Name: N-(2-Hydroxyethyl)adenosine
• Synonyms: N-(2-Hydroxyethyl)adenosine;6-Hydroxyethyladenosine;N6-(2-Hydroxyethyl)adenosine;NSC 54251;(2R,3R,4S,5R)-2-(6-((2-Hydroxyethyl)amino)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-di;(2R,3R,4S,5R)-2-(6-((2-Hydroxyethyl)aMino)-9H-purin-9-yl)-5-(hydroxyMethyl)tetrahydrofuran-3,4-diol;(2R,3R,4S,5R)-2-(6-((2-Hydroxyethyl)amino)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4
• CAS NO: 4338-48-1
• Molecular Formula: C₁₂H₁₇N₅O₅
• Molecular Weight: 311.3
• EINECS: 200-001-2
• Mol File: 4338-48-1.mol
• Article Data: 2

Chemical Properties

• Melting Point: 194-195℃
• Boiling Point: 725.8°Cat760mmHg
• Flash Point: 392.7°C
• Appearance: /
• Density: 1.88
• Vapor Pressure: 4.15E-22mmHg at 25°C
• Refractive Index: 1.806
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: N-(2-Hydroxyethyl)adenosine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-Hydroxyethyl)adenosine(4338-48-1)
• EPA Substance Registry System: N-(2-Hydroxyethyl)adenosine(4338-48-1)

Safety Data

• Hazardous Substances Data: 4338-48-1(Hazardous Substances Data)

Usage

Description

N-(2-Hydroxyethyl)adenosine, also known as 2-Hydroxyethyladenosine, is an organic compound derived from adenosine, a nucleoside composed of adenine attached to a ribose sugar. It is characterized by the presence of a 2-hydroxyethyl group attached to the nitrogen atom of the adenine base. This modification enhances its solubility and bioavailability, making it a potential candidate for various pharmaceutical applications.

Uses

Used in Pharmaceutical Industry:
N-(2-Hydroxyethyl)adenosine is used as an anticonvulsant for the treatment of epilepsy and other seizure disorders. It functions by activating the adenosine A1 receptor (AA1R), which plays a crucial role in modulating neuronal excitability and seizure threshold. This activation leads to a decrease in neuronal firing and a reduction in the severity and frequency of seizures.
Additionally, N-(2-Hydroxyethyl)adenosine may have potential applications in other areas of medicine, such as cardiovascular and respiratory diseases, due to the widespread role of adenosine receptors in regulating various physiological processes. However, further research is needed to fully understand its therapeutic potential and safety profile in these contexts.

InChI:InChI=1/C12H17N5O5/c18-2-1-13-10-7-11(15-4-14-10)17(5-16-7)12-9(21)8(20)6(3-19)22-12/h4-6,8-9,12,18-21H,1-3H2,(H,13,14,15)/t6-,8-,9-,12-/m1/s1

Synthetic route

1-(2-hydroxyethyl)adenosine perchlorate (96655-92-4) → NSC 54251 (4338-48-1)

Conditions	Yield
With water at 60℃; for 24h; pH=11;	93%

1-(2-hydroxyethyl)adenosine perchlorate (96655-92-4) → 1-(2-hydroxyethyl)inosine (33962-62-8) + NSC 54251 (4338-48-1)

Conditions	Yield
With disodium hydrogenphosphate; sodium dihydrogenphosphate; water at 95 - 100℃; for 5h; pH=6;	A 17% B 52%

N6-(2-hydroxyethyl)adenine (4551-95-5) + Inosine (58-63-9) → NSC 54251 (4338-48-1) + hypoxanthine (68-94-0)

Conditions	Yield
With purine nucleoside phosphorylase from Aeromonas hydrophyla, covalently immobilized on aminopropylsilica particles In aq. phosphate buffer; dimethyl sulfoxide at 37℃; for 0.166667h; pH=7.5; Flow reactor; Enzymatic reaction;	A 6.1 mg B n/a

Upstream product

• 4551-95-5 N⁶-(2-hydroxyethyl)adenine 
• 58-63-9 Inosine 
• 96655-92-4 1-(2-hydroxyethyl)adenosine perchlorate 

Relevant articles and documents

Flow-Synthesis of Nucleosides Catalyzed by an Immobilized Purine Nucleoside Phosphorylase from Aeromonas hydrophila: Integrated Systems of Reaction Control and Product Purification

A purine nucleoside phosphorylase from Aeromonas hydrophyla (AhPNP) was covalently immobilized in a pre-packed stainless steel column containing aminopropylsilica particles via Schiff base chemistry upon glutaraldehyde activation. The resulting AhPNP-IMER (Immobilized Enzyme Reactor, immobilization yield ≈50%) was coupled on-line through a 6-way switching valve to an HPLC apparatus containing an analytical or a semi-preparative chromatographic column. The synthesis of five 6-modified purine ribonucleosides was carried out by continuously pumping the reaction mixture through the AhPNP-IMER until the highest conversion was reached, and then directing the reaction mixture to chromatographic separation. The conditions of the AhPNP-catalyzed transglycosylations (2:1 ratio sugar donor:base acceptor; 10 mM phosphate buffer; pH 7.5; temperature 37 °C, flow rate 0.5 mL min-1) were optimized by a fractional factorial experimental design. Coupling the bioconversion step with the product purification in such an integrated platform resulted in a fast and efficient synthetic process (yield=52-89%; 10 mg) where sample handling was minimized. To date, AhPNP-IMER has retained completely its activity upon 50 reactions in 10 months.