Adenosine

Base Information

• Chemical Name: Adenosine
• CAS No.: 58-61-7
• Deprecated CAS: 46946-45-6,46969-16-8,46969-16-8
• Molecular Formula: C10H13N5O4
• Molecular Weight: 267.244
• Hs Code.: 29389090
• European Community (EC) Number: 200-389-9,607-743-5
• NSC Number: 755857
• UNII: K72T3FS567
• DSSTox Substance ID: DTXSID1022558
• Nikkaji Number: J4.501B
• Wikipedia: Adenosine
• Wikidata: Q190012
• NCI Thesaurus Code: C207
• RXCUI: 296
• Pharos Ligand ID: QVB8Q7NQV6B5
• Metabolomics Workbench ID: 37045
• ChEMBL ID: CHEMBL477
• Mol file: 58-61-7.mol

Synonyms:Adenocard;Adenoscan;Adenosine

Chemical Property of Adenosine

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 3.26E-19mmHg at 25°C
• Melting Point: 234-236 °C(lit.)
• Refractive Index: 1.907
• Boiling Point: 676.3 °C at 760 mmHg
• PKA: 3.6, 12.4(at 25℃)
• Flash Point: 362.8 °C
• PSA: 139.54000
• Density: 2.08 g/cm³
• LogP: -1.39880
• Storage Temp.: 2-8°C
• Solubility.: Slightly soluble in water, soluble in hot water, practically insoluble in ethanol (96 per cent) and in methylene chloride. It dissolves in dilute mineral acids.
• Water Solubility.: Soluble in water, ammonium hydroxide and dimethyl sulfoxide. Insoluble in ethanol.
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 267.09675391
• Heavy Atom Count: 19
• Complexity: 335

Purity/Quality:

99%, ^*data from raw suppliers

Androgen Receptor ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 24/25-36/37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)CO)O)O)N
• Isomeric SMILES: C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N
• Recent ClinicalTrials: BROKEN-SWEDEHEART-Optimized Pharmacological Treatment for Broken Heart (Takotsubo) Syndrome
• Recent EU Clinical Trials: Novel therapeutic strategies to reduce coronary microvascular obstruction and to OPTImize non-culprit stenoses revascularization in ST-Elevation acute Myocardial Infarction
• Recent NIPH Clinical Trials: Perfusion Reserve of Stenotic Coronary Artery with Cardiac Computer Tomography in Patients with Hemodialysis.
• Ubiquitous Signalling Molecule: Adenosine is a purine nucleoside signaling molecule found ubiquitously in human systems. It plays various roles related to metabolism, regulation of sleep patterns, development, neuroprotection, and cellular homeostasis.
• Interaction with Adenosine Receptors: Adenosine interacts with four G protein-coupled receptor (GPCR) subtypes known as A1, A2A, A2B, and A3 adenosine receptors (ARs).; Each receptor subtype has a unique pharmacological profile and tissue distribution, allowing adenosine to modulate diverse physiological processes.
• Modulation of Inflammation: Adenosine is a potent modulator of inflammation, making the adenosinergic system a promising pharmacological target for diseases involving inflammation. It regulates immune responses and inflammatory processes in conditions such as rheumatic diseases, neurological disorders, and cancer.
• Endogenous Anticonvulsant and Neuroprotectant: Adenosine acts as an endogenous anticonvulsant and neuroprotectant in the brain.; Seizure activity leads to the production of large quantities of adenosine, which helps to stop seizures.
• Role in Immune Response: Adenosine serves as a key mediator of the immune response, influencing the activation of immune cells and the generation of reactive oxygen species (ROS). It regulates neutrophil activation, which plays a crucial role in inflammation and immune responses.
• Neuromodulatory Function: In the central nervous system (CNS), adenosine acts as a neuromodulation.; Increased extracellular adenosine concentration in response to neuronal stress and damage can promote or attenuate neuroinflammation.
• Production and Metabolism: Adenosine is produced through various mechanisms, including the dephosphorylation of adenine nucleotides (ATP, ADP, and AMP) and the release of adenine nucleotides into the extracellular space.; Enzymes like ectonucleoside triphosphate diphosphohydrolase (CD39) and ecto-5鈥?-nucleotidase (CD73) catalyze the conversion of adenine nucleotides to adenosine.

Technology Process of Adenosine

There total 388 articles about Adenosine 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: 99.0%

triacetyladenosine (7387-57-7,953089-09-3) → adenosine (58-61-7)

Guidance literature:

With lipase A from Aspergillus niger; In aq. phosphate buffer; acetonitrile; at 25 ℃; for 0.5h; pH=7; Enzymatic reaction;

DOI:10.1039/c6ra19645d

Reference yield: 95.0%

8-mercaptoadenosine (3001-45-4) → adenosine (58-61-7)

Guidance literature:

In water; water-d2; for 12h; UV-irradiation; Inert atmosphere;

DOI:10.1021/jacs.1c07403

Reference yield: 95.0%

5'-O-(triphenylmethyl)adenosine (18048-85-6) → adenosine (58-61-7)

Guidance literature:

With ammonium cerium(IV) nitrate; silica gel; In dichloromethane; at 25 ℃; for 1.5h;

DOI:10.1021/jo000024o

upstream raw materials:

6-Chloropurine riboside

6-methylmercaptopurine riboside

adenosine monophosphate

5'-adenosine monophosphate

Downstream raw materials:

Cytidin-(3',5')-adenosin

kinetin riboside

N⁶,O^2'-methyladenosine

2'-O-methyl adenosine

Refernces

• 1、 Nam, Inho,Nam, Hong Gil,Zare, Richard N.. "Abiotic synthesis of purine and pyrimidine ribonucleosides in aqueous microdroplets". . p. 36 - 40. Retrieved 2018.
• 2、 Westmeyer, Gil G.,Durocher, Yves,Jasanoff, Alan. "A secreted enzyme reporter system for MRI". . p. 3909 - 3911. Retrieved 2010.
• 3、 OTT,WERKMAN. "Enzymic transfer of the ribosyl group from inosine to adenine.". . p. 609 - 611. Retrieved 1957.
• 4、 Wang, Chao,Chen, Qishui,Wang, Zhiqiang,Zhang, Xi. "An enzyme-responsive polymeric superamphiphile". . p. 8612 - 8615. Retrieved 2010.
• 5、 Akiyama,Tanaka,Bessho,Yoneda. "The reductive repair of adenine-1-oxide derivatives to adenine derivatives by γ-glutamylcysteinylglycine (glutathione)". . p. 2893 - 2895. Retrieved 1990.
• 6、 Laine, Maarit,L?nnberg, Tuomas,Helkearo, Mia,L?nnberg, Harri. "Cleavage of short oligoribonucleotides by a Zn2+binding multi-nucleating azacrown conjugate". . p. 111 - 117. Retrieved 2016.
• 7、 Zhao, Weian,Chiuman, William,Lam, Jeffrey C. F.,Brook, Michael A.,Li, Yingfu. "Simple and rapid colorimetric enzyme sensing assays using non-crosslinking gold nanoparticle aggregation". . p. 3729 - 3731. Retrieved 2007.
• 8、 Naka,Honjo. "Synthesis of 8 carbamoyl- and 8 carboxyadenosine 3',5' cyclic phosphates". . p. 2052 - 2056. Retrieved 1976.
• 9、 Ikeno, Shinya,Asakawa, Hitoshi,Haruyama, Tetsuya. "Molecular commonality detection using an artificial enzyme membrane for in situ one-stop biosurveillance". . p. 5540 - 5546. Retrieved 2007.
• 10、 Krompholz, Nina,Krischkowski, Carmen,Reichmann, Debora,Garbe-Schoenberg, Dieter,Mendel, Ralf-R.,Bittner, Florian,Clement, Bernd,Havemeyer, Antje. "The mitochondrial amidoxime reducing component (mARC) is involved in detoxification of N-hydroxylated base analogues". . p. 2443 - 2450. Retrieved 2012.