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CASTANOSPERMINE

CASTANOSPERMINE Structure
CAS No.
79831-76-8
Chemical Name:
CASTANOSPERMINE
Synonyms
CastanosperMin;CASTANOSPERMINE;(+)-Castanospermine;Castanospermine ,98%;1,6,7,8-TETRAHYDROXYOCTAHYDROINDOLIZINE;CASTANOSPERMINE, CASTANOSPERMUM AUSTRALE;(1S,6S,7R,8R,8AR)-1,6,7,8-TETRAHYDROXY-&;Castanospermine from Castanospermum austral;(8aα)-Octahydroindolizine-1β,6α,7β,8α-tetrol;Castanospermine Castanospermum australe seeds
CBNumber:
CB9387977
Molecular Formula:
C8H15NO4
Molecular Weight:
189.21
MOL File:
79831-76-8.mol
MSDS File:
SDS
Modify Date:
2023/6/30 15:45:59

CASTANOSPERMINE Properties

Melting point 213-217 °C (lit.)
alpha D25 +79.7° (c = 0.93 in water)
Boiling point 421.9±45.0 °C(Predicted)
Density 1.53±0.1 g/cm3(Predicted)
storage temp. Sealed in dry,2-8°C
solubility 1 M HCl: 20 mg/mL, clear, very faintly yellow
form White solid
pka 6.09(at 25℃)
color White or off-white
optical activity [α]20/D +80°, c = 0.9 in H2O
Water Solubility Soluble in water
Merck 13,1906
BRN 3588654
Stability Stable for 2 years from date of purchase as supplied. Solutions in distilled water may be stored at -20°C for up to 3 months.
CAS DataBase Reference 79831-76-8(CAS DataBase Reference)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H302-H312-H332
Precautionary statements  P261-P280h-P301+P312a-P304+P340-P321-P501a
Hazard Codes  Xn,Xi
Risk Statements  20/21/22-36/37/38
Safety Statements  26-36
WGK Germany  3
10-21
HS Code  2921290090
NFPA 704
0
3 0

CASTANOSPERMINE price More Price(2)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) 532673 (1S,6S,7R,8R,8aR)-1,6,7,8-Tetrahydroxyindolizidine 98% 79831-76-8 100MG ₹10164.68 2022-06-14 Buy
Sigma-Aldrich(India) 218775 Castanospermine, Castanospermum australe - CAS 79831-76-8 - Calbiochem Plant alkaloid inhibitor of several β-glucosidases and α-glucosidases, including those involved in N-linked processing of glycoproteins. 79831-76-8 1MG ₹5880 2022-06-14 Buy
Product number Packaging Price Buy
532673 100MG ₹10164.68 Buy
218775 1MG ₹5880 Buy

CASTANOSPERMINE Chemical Properties,Uses,Production

Description

Glucosidases catalyze the cleavage of individual glucosyl residues from various glycoconjugates, including complex carbohydrates and glycoproteins. Castanospermine is an inhibitor of both α- and β-glucosidases, inhibiting lysosomal and neutral α-glucosidases with Ki values of 0.1 and 10 μM, respectively, and lysosomal and cytosolic β-glucosidases with Ki values of 7 and 40 μM, respectively. It is effective both in vitro and in vivo. Through its effects on glucosidases, castanospermine blocks N-linked glycosylation during post-translational modification of proteins, affecting protein trafficking and cell functions that are dependent on glycosylation, including angiogenesis. Castanospermine also interferes with viral replication and infection that is dependent on glucosidase activity.

Chemical Properties

White Crystalline Solid

Occurrence

The seeds of Castanospermum australe yield this simple alkaloid. It forms colourless crystals from EtOH and is dextrorotatory with a specific rotation of [α]D25 +79.7° (c 0.93, H20). Castano spermine has been characterized as the crystalline methiodide, m.p. 11O-112°C.

Uses

Castanospermine is a plant alkaloid shown to be a potent inhibitor of lysosomal a-or beta- glucosidase. It also inhibits mammalian glucosidase 1 and beta-mannosidase from sweet almonds and fungal beta-xylosidase.

Biological Activity

Potent inhibitor of α - and β -glucosidases, especially glucosidase l (required for glucoprotein processing by transfer of mannose and glucose from asparagine-linked lipids). Inhibits HIV syncytium formation and replication.

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CASTANOSPERMINE Spectrum

1,6,7,8-indolizinetetrol,octahydro-,(1s-(1-alpha,6-beta,7-alpha,8-beta,8a-bet 7,8-indolizinetetrol,octahydro-,(1s,6s,7r,8r,8ar)-6 octahydro-1,6,7,8-indolizinetetrol(1s-(1-alpha,6-beta,7-alpha,8-beta,8a-beta CASTANOSPERMINE CASTANOSPERMINE, CASTANOSPERMUM AUSTRALE [1S-(1A,6B,7A,8B,8A-BETA)]-OCTAHYDRO-1,6,7,8-INDOLIZINETETROL (1S,6S,7R,8AR)-TETRAHYDROXYOCTAHYDROINDOLIZINE (1S,6S,7R,8R,8AR)-1,6,7,8-TETRAHYDROXYINDOLIZIDINE (1S,6S,7R,8R,8AR)-1,6,7,8-TETRAHYDROXYOCTAHYDROINDOLIZINE (1S,6S,7R,8R,8AR)-OCTAHYDRO-1,6,7,8-INDOLIZINETETROL 1,6,7,8-TETRAHYDROXYOCTAHYDROINDOLIZINE (1S,6S,7R,8R,8aR)-1,6,7,8-Tetrahydroxyoctahydroindolizidine, (1S,6S,7R,8R,8aR)-Octahydro-1,6,7,8-indolizinetetrol 1,6,7,8-Tetrahydroxyoctahydroindolizine, Castanospermine, (1S,6S,7R,8R,8aR)-Octahydro-1,6,7,8-indolizinetetrol, (1S,6S,7R,8R,8aR)-1,6,7,8-Tetrahydroxyoctahydroindolizidine Castanospermine from Castanospermum austral Castanospermine Castanospermum australe seeds castanospermine from castanospermum australe seeds castanospermine from castanospermum*australe seed (1S,6S,7R,8R,8AR)-1,6,7,8-TETRAHYDROXY-& 1,6,7,8-Indolizinetetrol, octahydro-, (1S,6S,7R,8R,8aR)- (1s,6s,7r,8r,8ar)-1,6,7,8-tetrahydroxyoctahydroindolizidine [1S-(1alpha,6beta,7alpha,8beta,8alphabeta)]-Octahydro-1,6,7,8-indolizinetetrol (3S,4R,5R,6R,7S)-1-Azabicyclo[4.3.0]nonane-3,4,5,7-tetrol (8aα)-Octahydroindolizine-1β,6α,7β,8α-tetrol [1S-(1α,6β,7α,8β,8aβ)]-Octahydro-1,6,7,8-indolizinetetrol Castanospermine ,98% CastanosperMin (1S,6S,7R,8R,8aR)-1,6,7,8-Tetrahydroxyindolizidine 98% Castanospermine/ (1S,6S,7R,8R,8Ar)-Indolizidine-1,6,7,8-Tetrol /(1S,6S,7R,8R,8aR)-1,2,3,5,6,7,8,8a-Octahydroindolizine-1,6,7,8-Tetrol (1S,6S,7R,8R,8aR)-2,3,4,5,6,7,8,8a-octahydro-1H-indolizin-4-ium-1,6,7,8-tetrol Castanospermine, Castanospermum australe - CAS 79831-76-8 - Calbiochem (1S,6S,7R,8R,8aR)-octahydroindolizine-1,6,7,8-tetrol (1S,6S,7R,8R,8aR)-Octahydroindolizine-1,6,7,8-tetraol Castanospermine,inhibit,Inhibitor,Glucosidase (+)-Castanospermine 79831-76-8 Enzyme Inhibitors Enzyme Inhibitors by Enzyme Glucosidase, alpha- Heterocyclic Building Blocks Indoles Substrate Analogs Enzymes, Inhibitors, and Substrates Enzyme Inhibitors by Type D to K BioChemical Biochemicals and Reagents Asymmetric Synthesis Chiral Building Blocks inhibitor Alkaloids All Inhibitors Glycosidase Inhibitors Inhibitors Miscellaneous Enzyme