Dioscin

Base Information

• Chemical Name: Dioscin
• CAS No.: 19057-60-4
• Molecular Formula: C₄₅H₇₂O₁₆
• Molecular Weight: 869.057
• Hs Code.: 29389090
• European Community (EC) Number: 866-819-8
• UNII: 3B95U4OLWV
• Nikkaji Number: J15.520I
• Wikidata: Q5807682
• Pharos Ligand ID: TZA5JGXD9UBS
• Metabolomics Workbench ID: 52716
• ChEMBL ID: CHEMBL507001
• Mol file: 19057-60-4.mol

Synonyms:dioscin

Chemical Property of Dioscin

Chemical Property:

• Melting Point: 294-296 °C
• Refractive Index: 1.613
• PKA: 12?+-.0.70(Predicted)
• PSA: 235.68000
• Density: 1.39 g/cm³
• LogP: 1.24170
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly, Sonicated)
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 7
• Exact Mass: 868.48203620
• Heavy Atom Count: 61
• Complexity: 1600

Purity/Quality:

Dioscin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CC=C6C5(CCC(C6)OC7C(C(C(C(O7)CO)OC8C(C(C(C(O8)C)O)O)O)O)OC9C(C(C(C(O9)C)O)O)O)C)C)C)OC1
• Isomeric SMILES: C[C@@H]1CC[C@@]2([C@H]([C@H]3[C@@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC=C6[C@@]5(CC[C@@H](C6)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O[C@H]8[C@@H]([C@@H]([C@H]([C@@H](O8)C)O)O)O)O)O[C@H]9[C@@H]([C@@H]([C@H]([C@@H](O9)C)O)O)O)C)C)C)OC1
• Description: Dioscin is extracted from Dioscorea nipponica. Rhizoma Dioscoreae Nipponicae is the dry rhizome of this plant. It can be orally used to treat joint pain, arthritis, malaria, and chronic bronchitis. In addition, it can also be used externally to treat sore carbuncle swollen. Rhizoma Dioscoreae Nipponicae is commonly used in the northeast region, Shanxi province, and Shandong province of China.
• Physical properties: Appearance: white powder. Solubility: insoluble in water, petroleum ether, and benzene; soluble in methanol, ethanol, and acetic acid; slightly soluble in acetone and amyl alcohol. Melting point: 294–296℃. Specific optical rotation: ?115° (c?=?0.373, ethanol).
• Uses: Dioscin, a natural steroid saponin that has been shown to promote anticancer activity against several forms of cancers. Dioscin induces cancer cell apoptosis through elevated oxidative stress mediated by downregulation of peroxiredoxins. Dioscin, a natural steroid saponin that has been shown to promote anticancer activity against several forms of cancers. Dioscin induces cancer cell apoptosis through elevated oxidative stress mediated by downregulation of peroxiredoxins.
• Indications: This drug was recorded in the national standards for chemical drugs, volume 5. Dioscin tablets, containing total dioscin, are used to treat coronary heart disease, coronary insufficiency, as well as control hyperlipidemia.

Technology Process of Dioscin

There total 41 articles about Dioscin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

diosgenyl 2,4-di-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-6-O-benzoyl-3-O-pivaloyl-β-D-glucopyranoside (243454-96-8) → dioscin (60478-68-4,19057-60-4)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; methanol; water; at 50 ℃; for 2h;

DOI:10.1016/S0040-4039(98)01354-9

Reference yield: 97.0%

diosgenin-3β-yl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1->4)-[(2,3,4-tri-O-acetyl)-α-L-rhamnopyranosyl)-(1->2)]-3,6-di-O-pivaloyl-β-D-glucopyranoside (335591-71-4) → dioscin (60478-68-4,19057-60-4)

Guidance literature:

With methanol; potassium hydroxide; at 65 ℃; for 20h;

DOI:10.1016/j.carres.2007.06.008

Reference yield: 95.0%

diosgenyl 3,6-di-O-benzyl-2,4-di-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-β-D-glucopyranoside (503314-24-7) → dioscin (60478-68-4,19057-60-4)

Guidance literature:

With ammonia; sodium; In tetrahydrofuran; for 0.25h;

DOI:10.1016/S0008-6215(02)00275-6

upstream raw materials:

methyl protodioscin

diosgenyl 2,4-di-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-6-O-benzoyl-3-O-pivaloyl-β-D-glucopyranoside

trigonelloside C

diosgenin-3β-yl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1->4)-[(2,3,4-tri-O-acetyl)-α-L-rhamnopyranosyl)-(1->2)]-3,6-di-O-pivaloyl-β-D-glucopyranoside

Downstream raw materials:

diosgenin 3-O-α-L-rhamnopyranosyl(1->4)-β-D-glucopyranoside

diosgenin acetate

L-rhamnose

trillin

Refernces

• 1、 Ichinose, Koji,You, Song,Kawano, Noriaki,Hayashi, Kaori,Yao, Xin-Sheng,Ebizuka, Yutaka. "Heterologous expression of furostanol glycoside 26-O-β-glucosidase of Costus speciosus in Nicotiana tabacum". . p. 599 - 603. Retrieved 1999.
• 2、 Asami,Hirai,Shoji. "Studies on the constituents of palmae plants. VI. Steroid saponins and flavonoids of leaves of Phoenix canariensis hort. ex CHABAUD, P. humilis ROYLE var. hanceana BECC., P. dactylifera L., and Licuala spinosa WURMB.". . p. 2053 - 2056. Retrieved 1991.
• 3、 -. "IMPROVED SYNTHESIS". Page/Page column 64. . Retrieved 2014/01/07.