Laxogenin

Base Information

• Chemical Name: Laxogenin
• CAS No.: 1177-71-5
• Deprecated CAS: 20470-24-0
• Molecular Formula: C₂₇H₄₂O₄
• Molecular Weight: 430.628
• UNII: HT7W184YG4
• Wikidata: Q27280083
• Metabolomics Workbench ID: 199184
• Mol file: 1177-71-5.mol

Synonyms:laxogenin

Chemical Property of Laxogenin

Chemical Property:

• Vapor Pressure: 2.45E-14mmHg at 25°C
• Melting Point: 210-212℃
• Refractive Index: 1.558
• Boiling Point: 548.924 °C at 760 mmHg
• Flash Point: 177.82 °C
• PSA: 55.76000
• Density: 1.16 g/cm³
• LogP: 4.97280
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 430.30830982
• Heavy Atom Count: 31
• Complexity: 766

Purity/Quality:

≥98% ^*data from raw suppliers

Laxogenine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CC(=O)C6C5(CCC(C6)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(=O)[C@@H]6[C@@]5(CC[C@@H](C6)O)C)C)C)OC1
• Uses: Laxogeninen has been used in the synthesis of brassinosteroid analogues from laxogenin and their plant growth promotion; spirostanic analogs of brassinolide and castasterone

Technology Process of Laxogenin

There total 18 articles about Laxogenin 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: 92.0%

3-O-benzyl laxogenin (210687-07-3) → (25R)-3β-hydroxy-5α-spirostan-6-one (20470-24-0,62212-10-6,1177-71-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; dichloromethane; at 20 ℃; for 12h; under 760.051 Torr;

DOI:10.1021/jo026103c

Reference yield: 92.0%

(3β,5α,6β,25R)-spirostan-3,6-diol (41743-71-9) → (25R)-3β-hydroxy-5α-spirostan-6-one (20470-24-0,62212-10-6,1177-71-5)

Guidance literature:

With N-Bromosuccinimide; water; acetic acid; In acetone; for 0.75h;

DOI:10.1039/b007656m

Reference yield: 89.0%

(25R)-6-oxo-5α-spirostan-3β-yl tosylate → (25R)-3β-hydroxy-5α-spirostan-6-one (20470-24-0,62212-10-6,1177-71-5)

Guidance literature:

With naphthalene radical anion sodium salt; at -80 ℃;

DOI:10.1016/j.steroids.2017.06.004

upstream raw materials:

(25R)-3β-acetoxy-5α-spirostan-6-one

(25R)-5α-spirostan-3,6-dione

(25R)-spirostan-3β-ol-6-one-3-O-<β-D-glucopyranosyl(1->4)><α-L-arabinopyranosyl(1->6)>-β-D-glucopyranoside

laxogenin 3-O-4)-O-<α-L-arabinopyranosyl-(1->6)>-β-D-glucopyranoside>

Downstream raw materials:

(3β,5α,6β,25R)-spirostan-3,6-diol

laxogenin 3-O-(3,6-di-O-benzoyl-2,4-di-O-levulinoyl-β-D-glucopyranoside)

laxogenin 3-O-(3,6-di-O-benzoyl-β-D-glucopyranoside)

laxogenin-3-yl 2,3-di-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-L-arabinopyranosyl)-D-glucopyranoside

Refernces

• 1、 Valeri, Brigita De,Usubillaga, Alfredo. "SAPOGENINS FROM SOLANUM MERIDENSE". . p. 2509 - 2511. Retrieved 1989.
• 2、 Ding, Ning,Chen, Qing,Zhang, Wei,Ren, Sumei,Guo, Ying,Li, Yingxia. "Structure-activity relationships of saponin derivatives: A series of entry inhibitors for highly pathogenic H5N1 influenza virus". scheme or table. p. 316 - 326. Retrieved 2012/08/08.
• 3、 Iglesias-Arteaga, Martin A.,Perez Gil, Roxana,Perez Martinez, Carlos S.,Coll Manchado, Francisco. "Spirostanic analogues of teasterone. Synthesis, characterisation and biological activity of laxogenin, (23S)-hydroxylaxogenin and 23-ketolaxogenin (23-oxolaxogenin)". . p. 261 - 266. Retrieved 2007/10/03.