CASTANOSPERMINE

Product Name: 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
Formula Weight: 189.21
MOL File: 79831-76-8.mol

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CASTANOSPERMINE Property

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)

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Safety

Hazard Codes: Xn,Xi
Risk Statements: 20/21/22-36/37/38
Safety Statements: 26-36
WGK Germany: 3
F: 10-21
HS Code: 2921290090

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H332Harmful if inhaled

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P321Specific treatment (see … on this label).

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 532673
Product name: (1S,6S,7R,8R,8aR)-1,6,7,8-Tetrahydroxyindolizidine
Purity: 98%
Packaging: 100mg
Price: $137.4
Updated: 2024/03/01

Sigma-Aldrich

Product number: 218775
Product name: Castanospermine
Packaging: 1mg
Price: $71.1
Updated: 2024/03/01

Alfa Aesar

Product number: J61071
Product name: Castanospermine, 99%
Packaging: 100mg
Price: $202.65
Updated: 2024/03/01

Alfa Aesar

Product number: J61071
Product name: Castanospermine, 99%
Packaging: 500mg
Price: $684.65
Updated: 2024/03/01

Cayman Chemical

Product number: 11313
Product name: Castanospermine
Purity: ≥98%
Packaging: 5mg
Price: $43
Updated: 2024/03/01

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CASTANOSPERMINE Chemical Properties,Usage,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 K_i values of 0.1 and 10 μM, respectively, and lysosomal and cytosolic β-glucosidases with K_i 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

a-L-fucosidases inhibitor

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.

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

CASTANOSPERMINE Preparation Products And Raw materials

Raw materials

Preparation Products

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CASTANOSPERMINE Suppliers

Austria 1 Canada 1 China 68 Germany 3 India 2 Japan 2 New Zealand 1 Switzerland 3 United Kingdom 11 United States 24 Global 116

J & K SCIENTIFIC LTD.

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Sigma-Aldrich

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View Lastest Price from CASTANOSPERMINE manufacturers

Zhuozhou Wenxi import and Export Co., Ltd

Product: (1S,6S,7R,8R,8aR)-1,6,7,8-Tetrahydroxyindolizidine 79831-76-8
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-06-27

79831-76-8, CASTANOSPERMINERelated Search:

3-(Diethylamino)-1,2-propanediol NSC45488 1-Deoxynojirimycin N-Methyl-4-piperidinol d-threoninol (S)-(+)-1-Methyl-3-pyrrolidinol (S)-3-Amino-1,2-propanediol 1-Piperidinepropanol 1,2,3-HEPTANETRIOL N-ETHYL-4-HYDROXYPIPERIDINE N-Methyl-D-prolinol (S)-(+)-1-DIMETHYLAMINO-2-PROPANOL 1-Methyl-2-piperidinemethanol 1-DIETHYLAMINO-2-PROPANOL 1-ETHYL-3-PYRROLIDINOL 4-(N-BUTYLAMINO)-1-BUTANOL 2-(Hydroxymethyl)piperidine 2-(Hydroxymethyl)pyrrolidine

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)-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)-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)-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

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Glucosidase, alpha-

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