Ouabain octahydrate

SIGMA/O3125 - ≥95% (HPLC), powder

Synonym: 1β,3β,5β,11α,14,19-Hexahydroxycard-20(22)-enolide 3-(6-deoxy-α-L-mannopyranoside); Acocantherine; G-Strophanthin

CAS Number: 11018-89-6
Empirical Formula (Hill Notation): C₂₉H₄₄O₁₂ · 8H₂O
Molecular Weight: 728.77
EC Number: 211-139-3
MDL Number: MFCD00149240
Linear Formula: C₂₉H₄₄O₁₂ · 8H₂O
Product Type: Chemical

Catalog Number	PKG Qty.	Price


45-O3125-250MG	250 mg	$64.90 1/EA	Add To Favorites
45-O3125-1G	1 g	$196.00 1/EA	Add To Favorites
45-O3125-5G	5 g	$781.00 1/EA	Add To Favorites
45-O3125-25G	25 g	$2590.00 1/EA	Add To Favorites

Properties
Descriptions
Safety Info.
Basic Data

ε (extinction coefficient)	15.5 at 220 nm in H₂O at 1 mM
assay	≥95% (HPLC)
biological source	plant seeds (Strophantus gratus)
color	white
form	powder
impurities	~8 mol/mol water
InChI	1S/C29H44O12.8H2O/c1-13-22(34)23(35)24(36)25(40-13)41-15-8-19(32)28(12-30)21-17(3-5-27(28,37)9-15)29(38)6-4-16(14-7-20(33)39-11-14)26(29,2)10-18(21)31;;;;;;;;/h7,13,15-19,21-25,30-32,34-38H,3-6,8-12H2,1-2H3;8*1H2/t13-,15-,16+,17+,18+,19+,21+,22-,23+,24+,25-,26+,27-,28+,29-;;;;;;;;/m0......../s1
InChI key	TYBARJRCFHUHSN-DMJRSANLSA-N
mp	260 °C
optical activity	[α]25/D −31 to −32.5° in H₂O(lit.)
Quality Level	200
SMILES string	O.O.O.O.O.O.O.O.C[C@@H]1O[C@@H](O[C@H]2C[C@@H](O)[C@]3(CO)[C@H]4[C@H](O)C[C@]5(C)[C@H](CC[C@]5(O)[C@@H]4CC[C@]3(O)C2)C6=CC(=O)OC6)[C@H](O)[C@H](O)[C@H]1O
solubility	ethanol: 10 mg/mL
	H₂O: 10 mg/mL (cold)
	H₂O: 50 mg/mL (hot)
storage temp.	room temp

Application:	Ouabain octahydrate has been used: • to determine the effect of salt and ammonia in the external environment on the rate of activity of Na⁺ /K⁺ in either silver or golden perch • in the basolateral compartment to induce maximal baseline short-circuit current in rat fetal distal lung epithelial (FDLE) cells • as an Na⁺/K⁺ ATPase inhibitor to study the relation between blister formation and adenosine triphosphate (ATP) dependent maintenance of plasma membrane homeostasis
Biochem/physiol Actions:	Cardiac glycoside, inhibits Na(+)/K(+) ATPase, regulates transcription of MDR (increase, Pgp) and MRP (increase MRP1 and decrease CFTR, cyctic fibrosis transport receptor or cAMP-activated Cl- channel) genes, also alters localization of MRP1. Ouabain resistance is associated with appearance of Na(+)/K(+) ATPase isoforms with low binding affinity.
Biochem/physiol Actions:	Ouabain has its specific binding site on integral proteins of the plasma membrane. Heart disease is treated using ouabain derivatives. Increased ouabain production is observed during exercise in humans. Abnormally high levels of ouabain are indicated in congestive heart failure and hypertension. Ouabain signalling affects intracellular calcium levels, which is known to activate nuclear factor κB (NFκB).
Disclaimer:	Aqueous solutions can be autoclaved.
Features and Benefits:	This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm .
General description:	Ouabain is a steroid hormone, naturally present in mammals.

Symbol	GHS06,GHS08
Signal word	Danger
Hazard statements	H301 + H331 - H373
Precautionary statements	P301 + P310 + P330 - P304 + P340 + P311 - P314
Hazard Codes	T
Risk Statements	23/25-33
Safety Statements	45
RIDADR	UN 1544PSN1 6.1 / PGI
WGK Germany	WGK 3

Purity	≥95% (HPLC)
mp	260 °C
Storage Temp.	room temp
UNSPSC	12352200

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