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

Catalog Number	PKG Qty.	Price


45-01890-5G	5 g	$48.30 1/EAAdd To Favorites	Add To Favorites
45-01890-25G	25 g	$167.00 1/EAAdd To Favorites	Add To Favorites
45-01890-100G	100 g	$387.00 1/EAAdd To Favorites	Add To Favorites

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(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
mp	234-236 °C (lit.)
optical activity	[α]20/D −70±3°, c = 2% in 5% NaOH
Quality Level	200
SMILES string	Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO)[C@@H](O)[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