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CASTANOSPERMINE

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
MDL Number:
MFCD00017555
MOL File:
79831-76-8.mol
MSDS File:
SDS
Last updated:2023-06-30 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)
FDA UNII Q0I3184XM7

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
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(41)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 532673 (1S,6S,7R,8R,8aR)-1,6,7,8-Tetrahydroxyindolizidine 98% 79831-76-8 100mg $137.4 2024-03-01 Buy
Sigma-Aldrich 218775 Castanospermine 79831-76-8 1mg $71.1 2024-03-01 Buy
Alfa Aesar J61071 Castanospermine, 99% 79831-76-8 100mg $202.65 2024-03-01 Buy
Alfa Aesar J61071 Castanospermine, 99% 79831-76-8 500mg $684.65 2024-03-01 Buy
Cayman Chemical 11313 Castanospermine ≥98% 79831-76-8 5mg $43 2024-03-01 Buy
Product number Packaging Price Buy
532673 100mg $137.4 Buy
218775 1mg $71.1 Buy
J61071 100mg $202.65 Buy
J61071 500mg $684.65 Buy
11313 5mg $43 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.

Uses

Castanospermine, is used as a glycosidase inhibitor and antiinflammatory agent.castanospermine is used to inhibit syncytium formation between HIV-infected and CD4-expressing cells and may also interfere with infectivity. It has also been demonstrated that this agent inhibits inflammation at the level of leukocyte extravasation in rat models of experimental adjuvant-induced arthritis and autoimmune encephalomyelitis. Castanospermine is an inhibitor of Glucosidase I, Maltase-glucoamylase, and MANBA. 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.

Uses

a-L-fucosidases inhibitor

Definition

ChEBI: Castanospermine is a tetrahydroxyindolizidine alkaloid that consists of octahydroindolizine having four hydroxy substituents located at positions 1, 6, 7 and 8 (the 1S,6S,7R,8R,8aR-diastereomer). It has a role as a metabolite, an anti-HIV-1 agent, an anti-inflammatory agent and an EC 3.2.1.* (glycosidase) inhibitor.

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.

storage

Store at RT

References

1) Saul et al. (1984), Studies on the mechanism of castanospermine inhibition of alpha- and beta-glucosidases; Arch. Biochem. Biophys, 230 668 2) Repp et al. (1985), The effects of processing inhibitors on N-linked oligosaccharides on the intracellular migration of glycoprotein E2 of mouse hepatitis virus and the maturation of coronavirus particles; J. Biol. Chem., 260 15873 3) Gruters et al. (1987), Interference with HIV-induced syncytium formation and viral infectivity by inhibitors of trimming glucosidase; Nature, 330 74 4) Franc et al. (1990), Effects of deoxymannojirimycin and castanospermine on the polarized secretion of thyroglobulin; Endocrinology, 126 1464 5) Pili et al. (1995), The alpha-glucosidase I inhibitor castanospermine alters endothelial cell glycosylation, prevents angiogenesis, and inhibits tumor growth; Mol. Cancer Res., 55 2920 6) Rhinehart et al. (1987), Castanospermine blocks the hyperglycemic response to carbohydrates in vivo: a result of intestinal disaccharidase inhibition; Life Sci., 41 2325

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Amadis Chemical Company Limited
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View Lastest Price from CASTANOSPERMINE manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
(1S,6S,7R,8R,8aR)-1,6,7,8-Tetrahydroxyindolizidine pictures 2021-07-02 (1S,6S,7R,8R,8aR)-1,6,7,8-Tetrahydroxyindolizidine
79831-76-8
US $15.00-10.00 / KG 1KG 99%+ HPLC Monthly supply of 1 ton Zhuozhou Wenxi import and Export Co., Ltd

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