Ginsenoside C

Base Information

• Chemical Name: Ginsenoside C
• CAS No.: 11021-13-9
• Deprecated CAS: 52351-30-1,52590-95-1,75139-47-8
• Molecular Formula: C₅₃H₉₀O₂₂
• Molecular Weight: 1079.28
• Hs Code.: 29389090
• European Community (EC) Number: 234-251-4
• UNII: N219O0L31C
• Nikkaji Number: J38.858K
• Wikidata: Q27891169
• Metabolomics Workbench ID: 87228
• ChEMBL ID: CHEMBL449303
• Mol file: 11021-13-9.mol

Synonyms:gingenoside C;ginsenoside Rb2

Chemical Property of Ginsenoside C

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 197-199 °C
• Refractive Index: 1.621
• Boiling Point: 1117.1 °C at 760 mmHg
• PKA: 12.85±0.70(Predicted)
• Flash Point: 629.4 °C
• PSA: 357.06000
• Density: 1.43 g/cm³
• LogP: -1.56350
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly, Sonicated)
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 14
• Hydrogen Bond Acceptor Count: 22
• Rotatable Bond Count: 15
• Exact Mass: 1078.59237449
• Heavy Atom Count: 75
• Complexity: 1950

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

Ginsenoside Rb2 ^*data from reagent suppliers

Safty Information:

• Statements: 22
• Safety Statements: 45-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCCC(C)(C1CCC2(C1C(CC3C2(CCC4C3(CCC(C4(C)C)OC5C(C(C(C(O5)CO)O)O)OC6C(C(C(C(O6)CO)O)O)O)C)C)O)C)OC7C(C(C(C(O7)COC8C(C(C(CO8)O)O)O)O)O)O)C
• Isomeric SMILES: CC(=CCC[C@@](C)([C@H]1CC[C@@]2([C@@H]1[C@@H](C[C@H]3[C@]2(CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C)C)O)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO[C@H]8[C@@H]([C@H]([C@H](CO8)O)O)O)O)O)O)C
• Uses: Ginsenoside Rb2 inhibits the catecholamines secretory responses activated by nicotinic stimulation and by direct membrane depolarization from isolated perfused rat adrenal medulla.

Technology Process of Ginsenoside C

There total 7 articles about Ginsenoside C 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: 90.0%

C55H92O23 → ginsenoside Rb2 (11021-13-9,68406-26-8,82166-13-0,82166-14-1,146987-67-9)

Guidance literature:

With potassium hydroxide; In methanol; Further stages; Reflux;

DOI:10.1039/c3sc51479j

Reference yield:

(20S)-3-O-{β-D-6-O-[(E)-but-2-enoyl]glucopyranosyl-(1->2)-β-D-glucopyranosyl}-20-O-[α-L-arabinopyranosyl-(1->6)-β-D-glucopyranosyl]protopanaxadiol (1346522-90-4) → ginsenoside Rb2 (11021-13-9,68406-26-8,82166-13-0,82166-14-1,146987-67-9)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 12h;

DOI:10.1002/cbdv.201000196

Reference yield:

C79H114O35 → ginsenoside Rb2 (11021-13-9,68406-26-8,82166-13-0,82166-14-1,146987-67-9) + C53H90O22

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 1h; Heating;

DOI:10.1248/cpb.40.2458

upstream raw materials:

(20S)-3-O-{β-D-6-O-[(E)-but-2-enoyl]glucopyranosyl-(1->2)-β-D-glucopyranosyl}-20-O-[α-L-arabinopyranosyl-(1->6)-β-D-glucopyranosyl]protopanaxadiol

malonyl-ginsenoside Rb₂

Downstream raw materials:

ginsenoside Rk₃

protopanaxadiol

ginsenoside F₂

compound K

Refernces

• 1、 Yu, Jun,Sun, Jiansong,Niu, Yiming,Li, Rongyao,Liao, Jinxi,Zhang, Fuyi,Yu, Biao. "Synthetic access toward the diverse ginsenosides". . p. 3899 - 3905. Retrieved 2013/09/23.
• 2、 Karikura,Tanizawa,Hirata,Miyase,Takino. "Studies on absorption, distribution, excretion and metabolism of Ginseng saponins. VIII. Isotope labeling of ginsenoside Rb2". . p. 2458 - 2460. Retrieved 2007/10/02.