Adenosine
SIGMA/01890
Synonym: 9-β-D-Ribofuranosyladenine; Adenine riboside; Adenine-9-β-D-ribofuranoside
CAS Number: 58-61-7
Empirical Formula (Hill Notation): C10H13N5O4
Molecular Weight: 267.24
EC Number: 200-389-9
MDL Number: MFCD00005752
Linear Formula: C10H13N5O4
Product Type: Chemical
| cation traces | Ca: ≤10 mg/kg |
| Cd: ≤5 mg/kg | |
| Co: ≤5 mg/kg | |
| Cr: ≤5 mg/kg | |
| Cu: ≤5 mg/kg | |
| Fe: ≤5 mg/kg | |
| Mg: ≤20 mg/kg | |
| Mn: ≤5 mg/kg | |
| Ni: ≤5 mg/kg | |
| Pb: ≤5 mg/kg | |
| Zn: ≤5 mg/kg | |
| form | powder |
| ign. residue | ≤0.1% (as SO4) |
| InChI | 1S/C10H13N5O4/c11-8-5-9(1 |
| InChI key | OIRDTQYFTABQOQ-KQYNXXCUSA |
| mp | 234-236 °C (lit.) |
| optical activity | [α]20/D −70±3°, c = 2% in 5% NaOH |
| SMILES string | Nc1ncnc2n(cnc12)[C@@H]3O[ |
| storage temp. | 2-8°C |
| Application: | Adenosine has been used as a standard to determine the adenosine content in whole heart samples from mice. |
| Biochem/physiol Actions: | Endogenous neurotransmitter at adenosine receptors. Cardioprotective effects may relate to activation of A1 adenosine receptors. The antiplatelet and anti−inflammatory actions of adenosine appear to be mediated via the A2 adenosine receptor. In contrast, adenosine appears to be a pro-inflammatory mediator in asthma and chronic obstructive pulmonary disease (COPD). |
| General description: | Adenosine is a purine nucleoside base. It consists of adenine bound to a ribose sugar molecule via a glycosidic bond. Adenosine is found intracellularly and extracellularly in living cells. It acts as a precursor and as a metabolite of adenine nucleotides. In all living organisms, adenosine acts as an essential structural factor for adenosinetriphosphate (ATP), adenosine diphosphate (ADP), and cyclic adenosine monophosphate (cAMP), thereby playing an important role in energy transfer. Adenosine plays a crucial role in the central nervous system, endocrine system, inflammatory and immune response, and cardiovascular system. It is an important endogenous modulator of kidney function, lung function, pain, and sleep via the activation of adenosine receptors. |
| Other Notes: | Substrate for the assay of adenosine deaminase |
| RIDADR | NONH for all modes of transport |
| WGK Germany | WGK 2 |
| Flash Point(F) | Not applicable |
| Flash Point(C) | Not applicable |
| mp | 234-236 °C (lit.) |
| Storage Temp. | 2-8°C |
| UNSPSC | 12352200 |