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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 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

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

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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:

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  • Castanospermine,inhibit,Inhibitor,Glucosidase
  • (+)-Castanospermine
  • 79831-76-8
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