CASTANOSPERMINE CAS 79831-76-8
Introduction：Basic information about CASTANOSPERMINE CAS 79831-76-8, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
CASTANOSPERMINE Basic information
| Product Name: | CASTANOSPERMINE |
| Synonyms: | 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 |
| CAS: | 79831-76-8 |
| MF: | C8H15NO4 |
| MW: | 189.21 |
| EINECS: | |
| Product Categories: | inhibitor;Alkaloids;All Inhibitors;Glycosidase Inhibitors;Inhibitors;Miscellaneous Enzyme |
| Mol File: | 79831-76-8.mol |
CASTANOSPERMINE Chemical 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 |
| pka | 6.09(at 25℃) |
| form | White solid |
| color | White or off-white |
| Optical Rotation | [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. |
| InChI | 1S/C8H15NO4/c10-4-1-2-9-3-5(11)7(12)8(13)6(4)9/h4-8,10-13H,1-3H2/t4-,5-,6+,7+,8+/m0/s1 |
| InChIKey | JDVVGAQPNNXQDW-TVNFTVLESA-N |
| SMILES | [H][C@]12[C@@H](O)CCN1C[C@H](O)[C@@H](O)[C@@H]2O |
| CAS DataBase Reference | 79831-76-8(CAS DataBase Reference) |
Safety Information
| 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 |
| Storage Class | 11 - Combustible Solids |
| Description | Glucosidases catalyze the cleavage of individual glucosyl residues from various glycoconjugates, including complex carbohydrates and glycoproteins. Castanospermine is an inhibitor of both α- |
| 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 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 | 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 |
| 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] RICK SAUL A. D E R J Molyneux. Studies on the mechanism of castanospermine inhibition of α- and β-glucosidases[J]. Archives of biochemistry and biophysics, 1984, 230 2: Pages 668-675. DOI:10.1016/0003-9861(84)90448-x [2] REINALD REPPS. The effects of processing inhibitors of N-linked oligosaccharides on the intracellular migration of glycoprotein E2 of mouse hepatitis virus and the maturation of coronavirus particles.[J]. The Journal of Biological Chemistry, 1985, 61 1: 15873-15879. DOI:10.1016/s0021-9258(17)36339-1 [3] ROB A. GRUTERS. Interference with HIV-induced syncytium formation and viral infectivity by inhibitors of trimming glucosidase[J]. Nature, 1987, 330 6143: 74-77. DOI:10.1038/330074a0 [4] J L FRANC J L A Giraud. Effects of deoxymannojirimycin and castanospermine on the polarized secretion of thyroglobulin.[J]. Endocrinology, 1990, 126 3: 1464-1470. DOI:10.1210/endo-126-3-1464 [5] R PILI. The alpha-glucosidase I inhibitor castanospermine alters endothelial cell glycosylation, prevents angiogenesis, and inhibits tumor growth.[J]. Cancer research, 1995, 55 13: 2920-2926. [6] B.L. RHINEHART . Castanospermine blocks the hyperglycemic response to carbohydrates in vivo: A result of intestinal disaccharidase inhibition[J]. Life sciences, 1987, 41 20: Pages 2325-2331. DOI:10.1016/0024-3205(87)90546-7 |
CASTANOSPERMINE Preparation Products And Raw materials
| Preparation Products | Propanoic acid, 2,2-dimethyl-, octahydro-1,6,7-tris(phenylmethoxy)-8-indolizinyl ester, 1S-(1.alpha.,6.beta.,7.alpha.,8.beta.,8a.beta.)--->1,6,7,8-Indolizinetetrol, octahydro-, 1,7,8-triacetate 6-methanesulfonate, 1S-(1.alpha.,6.beta.,7.alpha.,8.beta.,8a.beta.)--->Acetamide, N-1,7,8-tris(acetyloxy)octahydro-6-indolizinyl-, 1S-(1.alpha.,6.beta.,7.alpha.,8.beta.,8a.beta.)- |
