Adenosine

• CAS: 58-61-7
• Catalog Number: ACM58617
• Category: Main Products
• Molecular Weight: 267.24
• Molecular Formula: C10H13N5O4
• Synonyms: Adenine-9-1'-β-ribofuranoside
• IUPAC Name: (2R,3R,4S,5R)-2-(6-Aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• Canonical SMILES: C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)CO)O)O)N
• InChI: InChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1
• InChI Key: OIRDTQYFTABQOQ-KQYNXXCUSA-N
• Boiling Point: 410.43 °C
• Melting Point: 234-236 °C(lit.)
• Density: 1.3382 g/cm³
• Solubility: Soluble in water, ammonium hydroxide, dimethyl sulfoxide, insoluble in ethanol
• Appearance: White crystalline powder
• Storage: 2-8 °C
• Active Content: 95%
• Complexity: 335
• Exact Mass: 267.09675391
• Isomeric SMILES: C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N
• Monoisotopic Mass: 267.09675391
• Physical State: Solid
• pKa: pK1:3.6, pK2:12.4 (25°C)
• Refractive Index: 1.7610
• Topological Polar Surface Area: 140 Ų

Case Study

Role Of Adenosine In The Central Nervous System

Dunwiddie, Thomas V., and Susan A. Masino. Annual review of neuroscience 24.1 (2001): 31-55.

Adenosine is a modulator with a general and ubiquitous inhibitory effect on neuronal activity. Tonic activation of adenosine receptors by adenosine, which is normally present in the extracellular space of brain tissue, results in an inhibitory effect that appears to be mediated by adenosine A and A receptors. Relief of this tonic inhibition by receptor antagonists is responsible for the excitatory effects of these drugs. Characterization of the actions of adenosine receptor agonists and antagonists has led to many hypotheses regarding the actions of this nucleoside.
Adenosine participates in a variety of functions in the central nervous system. Although in a general sense many of its actions are inhibitory, consistent with its role as an endogenous anticonvulsant, neuroprotectant, and sleep-inducing factor, this depends on the brain system and complement of adenosine receptors present. There is little evidence that adenosine is a neurotransmitter; rather, it appears to be a neuromodulator that is released in some unconventional manner to modulate and regulate neuronal activity. A current challenge in the field is to better define the mechanisms of adenosine release in response to both pathological and nonpathological stimuli.

Custom Q&A

What is the molecular weight of Adenosine?

The molecular weight of Adenosine is 267.24.

What is the purity of Adenosine?

The purity of Adenosine is 99%.

What is the appearance of Adenosine?

Adenosine appears as a white powder.

What are some synonyms for Adenosine?

Some synonyms for Adenosine are 9-beta-D-Ribofuranosidoadenine and 9-beta-D-Ribofuranosyl-9H-purin-6-amine.

What is the physical state of Adenosine?

The physical state of Adenosine is solid.

What are the typical applications of Adenosine?

Adenosine is used as an emulsion stabilizer and dispersing agent, as well as an intermediate in organic synthesis.

What is the CAS number of Adenosine?

The CAS number of Adenosine is 58-61-7.

What is the molecular formula of Adenosine?

The molecular formula of Adenosine is C10H13N5O4.

What is the percentage of actives in Adenosine?

The percentage of actives in Adenosine is 95%.

What is the chemical composition of Adenosine?

Adenosine is composed of carbon, hydrogen, nitrogen, and oxygen.

Synthetic Use

Upstream Synthesis Route 1

• 7387-57-7

• 58-61-7

Reference: [1]RSC Advances,2016,vol. 6,p. 88974 - 88978

Upstream Synthesis Route 2

• 56-65-5

• 58-61-7

Reference: [1]Zhurnal Obshchei Khimii,1959,vol. 29,p. 215,219;engl.Ausg.S.218,222

Downstream Synthesis Route 1

• 98-88-4
• 58-61-7

• 22224-41-5

Reference: [1] Chemische Berichte, 1952, vol. 85, p. 1000,1005

Downstream Synthesis Route 2

• 58-61-7

• 39824-26-5

Reference: [1] Tetrahedron Letters, 2017, vol. 58, # 3, p. 190 - 193

Downstream Synthesis Route 3

• 58-61-7

• 1818-71-9

Reference: [1] Analytical Chemistry, 2007, vol. 79, # 2, p. 744 - 750

Downstream Synthesis Route 4

• 108-24-7
• 58-61-7

• 7387-57-7

Reference: [1]Journal of Biological Chemistry,1959,vol. 234,p. 603,605

* For details of the synthesis route, please refer to the original source to ensure accuracy.