CAS 53-41-8 Androsterone cis-Androsterone
53-41-8 - Names and Identifiers
Name Androsterone
Synonyms Androsterone
cis-Androsterone
3alpha-Hydroxy-17-androstanone
3-alpha-hydroxy-17-androstanone
3-Epihydroxyetioallocholan-17-one
(3alpha)-3-hydroxyandrostan-17-one
3alpha-Hydroxy-5alpha-androstan-17-one
5-alpha-Androstan-3 alpha-ol-17-one-16
3-alpha-hydroxy-5-alpha-androstan-17-on
3-alpha-hydroxy-5-alpha-androstan-17-one
(3β,8xi,9xi,14xi)-3-hydroxyandrostan-17-one
3-hydroxy-,(3-alpha,5-alpha)-androstan-17-on
3-hydroxy-10,13-dimethylperhydrocyclopenta[a]phenanthren-17-one
(3R,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one
CAS 53-41-8
EINECS 200-173-4
InChI InChI=1/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12 ,13-,14 ,15 ,16 ,18-,19-/m0/s1
53-41-8 - Physico-chemical Properties
Molecular Formula C19H30O2
Molar Mass 290.44
Density 1.0320 (rough estimate)
Melting Point 181-184°C(lit.)
Boling Point 372.52°C (rough estimate)
Specific Rotation(α) 96 º (c=1, C2H5OH)
Flash Point 176.4°C
Water Solubility 11.5mg/L(23.5 ºC)
Vapor Presure 1.5E-08mmHg at 25°C
Appearance neat
Merck 13,645
BRN 2217626
pKa 15.14±0.60(Predicted)
Storage Condition −20°C
Refractive Index 1.4709 (estimate)
In vitro study Androsterone activates both the mFXR-LBD and the hFXR-LBD, with Androsterone activating the mFXR-LBD more strongly than the hFXR-LBD. Furthermore, cotransfection studies with gal4-hFXR-LBD and SRC-1/VP16 expression plasmids demonstrate that Androsterone potentiates the interaction of SRC-1 with the hFXR-LBD. Several amino acid changes including H294S, S332V, R351H, and Y361F significantly reduce Androsterone activation. Androsterone (5α, 3α-A) (10 to 100 μM) also inhibits epileptiform discharges in a concentration-dependent fashion in the in vitro slice model.
In vivo study Androsterone treatment results in a significant induction of small heterodimer partner (SHP), suggesting Androsterone may activate endogenous FXR. Intraperitoneal injection of Androsterone (5α, 3α-A) protects mice in a dose-dependent fashion from seizures in the following models (ED 50 , dose in mg/kg protecting 50% of animals): 6 Hz electrical stimulation (29.1), pentylenetetrazol (43.5), pilocarpine (105), 4-AP (215), and maximal electroshock (224).
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