Cauloside C

Base Information

• Chemical Name: Cauloside C
• CAS No.: 20853-58-1
• Molecular Formula: C41H66 O13
• Molecular Weight: 766.967
• UNII: 909OGZ2782
• ChEMBL ID: CHEMBL537960
• Nikkaji Number: J39.946I
• Wikidata: Q27155129
• Mol file: 20853-58-1.mol

Synonyms:cauloside C

Chemical Property of Cauloside C

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 252～255℃
• Boiling Point: 881.9°C at 760 mmHg
• PKA: 4.63±0.70(Predicted)
• Flash Point: 260.9°C
• PSA: 215.83000
• Density: 1.35g/cm³
• LogP: 2.49350
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 7
• Exact Mass: 766.45034216
• Heavy Atom Count: 54
• Complexity: 1460

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

CaulosideC ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)CO)OC6C(C(C(CO6)O)O)OC7C(C(C(C(O7)CO)O)O)O)C)C)C2C1)C)C(=O)O)C
• Isomeric SMILES: C[C@]12CC[C@@H]([C@@]([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(CC[C@@]5([C@H]4CC(CC5)(C)C)C(=O)O)C)C)(C)CO)O[C@H]6[C@@H]([C@H]([C@H](CO6)O)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O
• Description: Hederoside D2 is a triterpenoid saponin originally isolated from C. robustum rhizome and roots and has diverse biological activities. It induces potassium release and hemolysis in mouse erythrocytes in a pH-dependent manner when used at a concentration of 10 μg/ml. Hederoside D2 is cytotoxic to N1E-115 neuroblastoma cells at low pH. It induces proliferation of human embryonic fibroblasts in acidic medium, an effect that can be blocked by the calcium channel blockers verapamil , diltiazem, and nitrendipine .

Technology Process of Cauloside C

There total 10 articles about Cauloside 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: 88.0%

allyl 3-O-[2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1->2)-3,4-di-O-benzoyl-β-L-arabinopyranosyl]-23-O-benzoylhederagenate (852448-41-0) → 3-O-[β-D-glucopyranosyl-(1->2)-β-L-arabinopyranosyl]-hederagenin (20853-58-1)

Guidance literature:

allyl 3-O-[2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1->2)-3,4-di-O-benzoyl-β-L-arabinopyranosyl]-23-O-benzoylhederagenate; With potassium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In methanol; at 60 ℃; for 6h;

With hydrogen; palladium on activated charcoal; In ethanol; at 20 ℃; for 48h;

DOI:10.1016/j.tet.2005.03.003

Reference yield: 87.0%

allyl 3-O-[2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1->2)-3,4-di-O-benzoyl-α-L-arabinopyranosyl]-23-O-benzoylhederagenate → hederagenin 3-O-β-D-glucopyranosyl-(1->2)-O-α-L-arabinopyranoside (20853-58-1)

Guidance literature:

allyl 3-O-[2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1->2)-3,4-di-O-benzoyl-α-L-arabinopyranosyl]-23-O-benzoylhederagenate; With potassium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; at 60 ℃; for 7h;

With hydrogen; palladium on activated charcoal; In ethanol; at 20 ℃;

DOI:10.1016/j.tet.2005.03.003

Reference yield:

hederagenin 3-O- 2)-α-L-arabinopyranoside> 28-O- 4)-O-β-D-glucopyranosyl-(1-> 6)-β-D-glucopyranoside> (60454-69-5) → hederagenin 3-O-β-D-glucopyranosyl-(1->2)-O-α-L-arabinopyranoside (20853-58-1)

Guidance literature:

With potassium hydroxide; In methanol; water; at 100 ℃; for 2h;

DOI:10.1023/A:1002891507725

upstream raw materials:

C₅₃H₈₆O₂₃

hederagenin 3-O- 2)-α-L-arabinopyranoside> 28-O- 4)-O-β-D-glucopyranosyl-(1-> 6)-β-D-glucopyranoside>

Medicoside C

allyl 3-O-[2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1->2)-3,4-di-O-benzoyl-β-L-arabinopyranosyl]-23-O-benzoylhederagenate

Downstream raw materials:

β-D-glucose

L-arabinose

hedaragenin

D-Glucose

Refernces

• 1、 Kumekawa,Itokawa,Fujita. "The study on the constituents of Clematis and Akebia sp. III. The study on the structures of akebosides isolated from the stem of Akebia quinata Decne". . p. 2294 - 2300. Retrieved 1974.
• 2、 Plé, Karen,Chwalek, Martin,Voutquenne-Nazabadioko, Laurence. "Synthesis of L-arabinopyranose containing hederagenin saponins". . p. 4347 - 4362. Retrieved 2007/10/03.
• 3、 Sobolev,Grishkovets,Shashkov,Tolkacheva,Chirva, V. Ya.. "Triterpenoid glycosides of Fatsia japonica. III. Isolation and structure of glycosides from fruit pericarp". . p. 538 - 539. Retrieved 2007/10/03.