Cimigenol xyloside

Base Information

• Chemical Name: Cimigenol xyloside
• CAS No.: 27994-11-2
• Molecular Formula: C35H56 O9
• Molecular Weight: 620.824
• UNII: 1CW26VCP4H
• ChEMBL ID: CHEMBL218613
• DSSTox Substance ID: DTXSID0033334
• Metabolomics Workbench ID: 198802
• Nikkaji Number: J17.167K
• Wikidata: Q27138585
• Mol file: 27994-11-2.mol

Synonyms:beta-D-Xylopyranoside, (3beta,15alpha,16alpha,23R,24S)-16,23-16,24-diepoxy-15,25-dihydroxy-9,19-cyclolanostan-3-yl;cimigenoside

Chemical Property of Cimigenol xyloside

Chemical Property:

• Melting Point: 269-271 °C
• Boiling Point: 740.3±60.0 °C(Predicted)
• PKA: 13.03±0.70(Predicted)
• PSA: 138.07000
• Density: 1.32±0.1 g/cm3(Predicted)
• LogP: 3.12140
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 3
• Exact Mass: 620.39243336
• Heavy Atom Count: 44
• Complexity: 1210

Purity/Quality:

98% ^*data from raw suppliers

CiMigenol 3-beta-D-xylopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2C(OC3(C1C4(CCC56CC57CCC(C(C7CCC6C4(C3O)C)(C)C)OC8C(C(C(CO8)O)O)O)C)O2)C(C)(C)O
• Isomeric SMILES: C[C@@H]1C[C@@H]2[C@H](O[C@]3([C@H]1[C@]4(CC[C@@]56C[C@@]57CC[C@@H](C([C@@H]7CC[C@H]6[C@@]4([C@H]3O)C)(C)C)O[C@H]8[C@@H]([C@H]([C@@H](CO8)O)O)O)C)O2)C(C)(C)O
• Uses: Cimigenoside exhibits cytotoxicity against five human tumor cell lines.

Technology Process of Cimigenol xyloside

There total 2 articles about Cimigenol xyloside 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:

2'-O-acetylcimigenol-3-O-β-D-xylopyranoside (1316305-70-0) → cimigenol 3-O-β-D-xylopyranoside (27994-11-2)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃;

DOI:10.1016/j.phytochem.2011.03.022

Reference yield:

24-O-acetylhydroshengmanol 3-O-β-D-xylopyranoside (78213-32-8) → cimigenol xyloside (27994-11-2,62498-89-9,70518-90-0)

Guidance literature:

With sulfuric acid; water; In methanol; for 26h; Ambient temperature;

DOI:10.1248/cpb.29.955

Reference yield:

cimigenol 3-O-β-D-xylopyranoside (27994-11-2) → D-Xylose (87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2)

Guidance literature:

With hydrogenchloride; water; In methanol; for 4h; Reflux;

DOI:10.1016/j.phytochem.2011.03.022

upstream raw materials:

24-O-acetylhydroshengmanol 3-O-β-D-xylopyranoside

2'-O-acetylcimigenol-3-O-β-D-xylopyranoside

Downstream raw materials:

D-Xylose

Refernces

• 1、 Sagurai,Kimura,Inoue,Nagai. "Studies on the Chinese crude drug 'shoma.' V. Structures of 24-O-acetylhydroshengmanol xyloside and 22-hydroxycimigenol xyloside". . p. 955 - 960. Retrieved 2007/10/02.