Ruscogenin

Base Information

• Chemical Name: Ruscogenin
• CAS No.: 472-11-7
• Deprecated CAS: 881025-73-6
• Molecular Formula: C27H42O4
• Molecular Weight: 430.628
• Hs Code.: 29389090
• European Community (EC) Number: 207-447-2
• UNII: BXI92R2VUJ
• DSSTox Substance ID: DTXSID401019319
• Nikkaji Number: J5.950A
• Wikidata: Q27108184
• Metabolomics Workbench ID: 35132
• ChEMBL ID: CHEMBL1169820
• Mol file: 472-11-7.mol

Synonyms:Ruscogenin(6CI,7CI);Spirost-5-ene-1b,3b-diol, (25R)- (8CI);Spiro[8H-naphth[2',1':4,5]indeno[2,1-b]furan-8,2'-[2H]pyran], spirost-5-ene-1,3-diolderiv.;25D-Spirost-5-ene-1β,3β-diol;

Chemical Property of Ruscogenin

Chemical Property:

• Vapor Pressure: 5.03E-15mmHg at 25°C
• Melting Point: 198-202oC
• Refractive Index: 1.576
• Boiling Point: 563.1 °C at 760 mmHg
• PKA: 14.56±0.70(Predicted)
• Flash Point: 294.3 °C
• PSA: 58.92000
• Density: 1.18 g/cm³
• LogP: 4.68470
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 430.30830982
• Heavy Atom Count: 31
• Complexity: 779

Purity/Quality:

99% ^*data from raw suppliers

Ruscogenin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

Useful:

• Canonical SMILES: CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CC=C6C5(C(CC(C6)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([C@@H](C[C@@H](C6)O)O)C)C)C)OC1
• Uses: A major steroidal sapogenin from Radix ophiopogon japonicus with robust anti-inflammatory and anti-thrombotic activities. Studies suggest that it inhibits adhesion of leukocytes to a human umbilical v ein endothelial cell line (ECV304) injured by tumor necrosis factor-α (TNF-α) in a concentration-dependent manner. A major steroidal sapogenin from Radix ophiopogon japonicus with robust anti-inflammatory and anti-thrombotic activities. Studies suggest that it inhibits adhesion of leukocytes to a human umbilical vein endothelial cell line (ECV304) injured by tumor necrosis factor-α (TNF-α) in a concentration-dependent manner.

Technology Process of Ruscogenin

There total 32 articles about Ruscogenin 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: 96.0%

3β-O-tert-butyldimethylsilyl-(25R)-ruscogenin (201858-23-3) → (25R)-ruscogenin (472-11-7,874485-32-2)

Guidance literature:

With hydrogenchloride; In acetone; for 1h; Ambient temperature;

DOI:10.1016/S0040-4039(97)10536-6

Reference yield: 66.0%

3β-acetoxyspirost-5-ene-1-one (90802-64-5) → (20S,22R,25R)-1α,3β-dihydroxyspirost-5-ene (79037-17-5,874485-32-2) + (25R)-ruscogenin (472-11-7,874485-32-2)

Guidance literature:

With lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; cooling 1 h, r.t., 1 h;

DOI:10.1016/S0040-4020(01)92435-4

Reference yield: 60.0%

spirost-5-ene-1-oxo-3β-ol (14414-62-1) → (20S,22R,25R)-1α,3β-dihydroxyspirost-5-ene (79037-17-5,874485-32-2) + (25R)-ruscogenin (472-11-7,874485-32-2)

Guidance literature:

With sodium tetrahydroborate; In methanol; for 2h; Ambient temperature;

DOI:10.1016/S0040-4020(01)92435-4

upstream raw materials:

spirosta-5(6),25(27)-diene-1β,3β-diol

spirost-5-ene-1-oxo-3β-ol

ophiopogonin B

(25R)-ruscogenin 1-O-α-L-rhamnopyranosyl-(1->2)-4-O-sulfo-β-D-arabinopyranoside

Downstream raw materials:

ruscogenin acetate

(20S,22R,25R)-1α,3β-dihydroxyspirost-5-ene

1β,3β,16β,26-tetrabenzoyloxycholest-5-ene

1β,3β,16β-tribenzoyloxycholest-5-ene

Refernces

• 1、 Napolitano, Assunta,Muzashvili, Tamar,Perrone, Angela,Pizza, Cosimo,Kemertelidze, Ether,Piacente, Sonia. "Steroidal glycosides from Ruscus ponticus". . p. 651 - 661. Retrieved 2011.
• 2、 Qu, Yuan,Zhang, Yang,Pei, Liang,Wang, Yan,Gao, Lijuan,Huang, Qianming,Ojika, Makoto,Sakagami, Youji,Qi, Jianhua. "New neuritogenic steroidal saponin from Ophiopogon japonicus (Thunb.) Ker-Gawl". . p. 1201 - 1204. Retrieved 2011.
• 3、 Tang, Liying,Wang, Zhuju,Wu, Hongwei,Yokosuka, Akihito,Mimaki, Yoshihiro. "Steroidal glycosides from the underground parts of Dracaena thalioides and their cytotoxic activity". . p. 102 - 110. Retrieved 2015/02/19.