Inosine

Base Information

• Chemical Name: Inosine
• CAS No.: 58-63-9
• Molecular Formula: C10H12N4O5
• Molecular Weight: 268.229
• Hs Code.: 29389090
• Mol file: 58-63-9.mol

Synonyms:9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one;4-acetamidobenzoic acid; 1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione; 9-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one; 1-dimethylaminopropan-2-ol;6-Hydroxy-9-(β-D-ribofuranosyl)-9H-purine;2',3',5'–Triacetylinosine;iso-prinosine;Inosine (8CI,9CI);hypoxanthine-ribose;.beta.-Inosine;Inosina [INN-Spanish];9-.beta.-D-Ribofuranosylhypoxanthine;Hypoxanthine 9-beta-D-ribofuranoside;Oxiamin;556-08-1;Hypoxanthine, 9-beta-D-ribofuranosyl-;Inosine-Pranobex;Ribonosine;(-)-Inosine;Inotin (TN);Hypoxanthine ribonucleoside;9H-purin-6-ol, 9-pentofuranosyl-;9-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one;Inosine [INN:JAN];Atorel;9-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one;Inosine (JAN);1,9-Dihydro-9-beta-D-ribofuranosyl-6H-purin-6-one;beta-D-Ribofuranoside, hypoxanthine-9;

Chemical Property of Inosine

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 1.52E-22mmHg at 25°C
• Melting Point: 222-226 °C (dec.)(lit.)
• Refractive Index: -52 ° (C=1, H2O)
• Boiling Point: 732.815 °C at 760 mmHg
• PKA: 13.24±0.70(Predicted)
• Flash Point: 396.993 °C
• PSA: 133.49000
• Density: 2.085 g/cm³
• LogP: -2.26890
• Storage Temp.: Store at RT.
• Solubility.: H2O: 0.5 M, clear, colorless
• Water Solubility.: 2.1 g/100 mL (20 ºC)

Purity/Quality:

99.5% ^*data from raw suppliers

Inosine 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Composition and Structure: Inosine is a purine nucleoside composed of a hypoxanthine base linked to a ribose sugar molecule.^[1]
• Categories and Type: Inosine serves as a post-transcriptional modification in RNA, found in various RNA types including tRNA, mRNA, rRNA, long non-coding RNA (lncRNA), and miRNA. It also acts as a signaling molecule with therapeutic potential in various biological and pathological processes.
• Mechanism of Action: Inosine arises from the deamination of adenosine by adenosine deaminases, leading to structural, folding, and functional changes in RNA molecules. It modulates neurotransmitter release, activates intracellular signaling pathways, and interacts with adenosine receptors, influencing various physiological processes.
• Pharmacokinetics: Inosine can cross the blood-brain barrier and exhibits systemic effects when administered exogenously. It modulates neuronal activity, promotes neural regeneration, and influences neurotransmitter release.^[2]
• Uses: Inosine has diverse applications in neurology, psychiatry, virology, and metabolism. It is studied for its potential in neural regeneration, depression treatment, anxiety modulation, epilepsy management, schizophrenia treatment, cognition enhancement, Parkinson's disease therapy, chronic pain relief, brown adipose tissue activation, and energy homeostasis.^[3]
• Production Methods: Inosine is generated through the hydrolytic deamination of adenosine to inosine by adenosine deaminases. It can also be released by cultured neuronal cells and administered exogenously via various routes. Inosine can be obtained through chemical synthesis, hydrolytic deamination of adenosine, or isolated from natural sources. The synthesis process involves combining hypoxanthine with ribose under controlled conditions.
• References: [1] Inosine and its methyl derivatives: Occurrence, biogenesis, and function in RNA; DOI 10.1016/j.pbiomolbio.2022.01.001; [2] Inosine as a Tool to Understand and Treat Central Nervous System Disorders: A Neglected Actor?; DOI 10.3389/fnins.2021.703783; [3] Inosine: novel activator of brown adipose tissue and energy homeostasis; DOI 10.1016/j.tcb.2023.04.007

Technology Process of Inosine

There total 63 articles about Inosine 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: 71.0%

8-mercaptoadenosine (3001-45-4) → (5'R)-5',8-cycloadenosine (62475-47-2) + inosine (58-63-9) + adenosine (58-61-7)

Guidance literature:

With hydrogenchloride; sodium dihydrogenphosphate; water; sodium nitrite; In water-d2; at 20 ℃; pH=4; Inert atmosphere;

DOI:10.1021/jacs.1c07403

Reference yield: 58.0%

3′-deoxyinosine (13146-72-0) + 2-fluoroadenosine (146-78-1) → (2R,3R,5S)-2-(6-amino-2-fluoro-9H-purin-9-yl)-5-(hydroxymethyl)oxolan-3-ol (15386-69-3) + Inosine (58-63-9)

Guidance literature:

With potassium dihydrogenphosphate; recombinant E_. coli purine nucleoside phosphorylase; In water; at 52 ℃; for 288h; pH=7; Enzymatic reaction;

DOI:10.1055/s-0036-1590804

Reference yield: 15.0%

N6-aminoadenosine (5746-27-0) → Inosine (58-63-9) + Nebularin (550-33-4) + adenosine (58-61-7)

Guidance literature:

With ammonia; In methanol;

upstream raw materials:

adenosine

inosine-5'-monophosphate

uridine

G

Downstream raw materials:

2',3',5'-tri-O-acetylinosine

9-(2,3-Anhydro-β-D-ribofuranosyl)hypoxanthine

9-(2,3-Dideoxy-β-D-glycero-pent-2-enofuranosyl)hypoxanthine

Allopurinol

Refernces

• 1、 Moosavi-Movahedi,Tehrani, H. Sepassi,Amanlou,Soltani Rad,Hakimelahi,Tsai,Ataie,Saboury,Ahmad,Khalafi-Nezhad,Poursasan,Sharifizadeh. "Kinetic and conformational studies of adenosine deaminase upon interaction with oxazepam and lorazepam". . p. 197 - 205. Retrieved 2010.
• 2、 Marquez, Victor E.,Schroeder, Gottfried K.,Ludek, Olaf R.,Siddiqui, Maqbool A.,Ezzitouni, Abdallah,Wolfenden, Richard. "Contrasting behavior of conformationally locked carbocyclic nucleosides of adenosine and cytidine as substrates for deaminases". . p. 614 - 632. Retrieved 2009.
• 3、 Qi, Shenglan,Guan, Huida,Deng, Gang,Yang, Tao,Cheng, Xuemei,Liu, Wei,Liu, Ping,Wang, Changhong. "Rapid, reliable, and sensitive detection of adenosine deaminase activity by UHPLC-Q-Orbitrap HRMS and its application to inhibitory activity evaluation of traditional Chinese medicines". . p. 175 - 181. Retrieved 2018.
• 4、 Zarkin, Allison K.,Elkins, Phyllis D.,Gilbert, Amanda,Jester, Teresa L.,Seltzman, Herbert H.. "Synthesis of 13C-labeled 5-aminoimidazole-4-carboxamide-1-β-D-[13C5] ribofuranosyl 5′-monophosphate". . p. 820 - 825. Retrieved 2018.
• 5、 Brown, David M.,Netting, Andrew G.,Chun, Byoung K.,Choi, Yongseok,Chu, Chung K.,Gero, Annette M.. "L-nucleoside analogues as potential antimalarials that selectively target Plasmodium falciparum adenosine deaminase". . p. 2521 - 2532. Retrieved 1999.
• 6、 Xu, Jianfeng,Green, Nicholas J.,Russell, David A.,Liu, Ziwei,Sutherland, John D.. "Prebiotic Photochemical Coproduction of Purine Ribo- And Deoxyribonucleosides". supporting information. p. 14482 - 14486. Retrieved 2021/09/18.
• 7、 Annunziata, Francesca,Bavaro, Teodora,Calleri, Enrica,Conti, Paola,Pinto, Andrea,Previtali, Clelia,Rinaldi, Francesca,Speranza, Giovanna,Tamborini, Lucia,Terreni, Marco,Ubiali, Daniela. "An enzymatic flow-based preparative route to vidarabine". . . Retrieved 2020/03/23.