Ponasterone A

Base Information

• Chemical Name: Ponasterone A
• CAS No.: 13408-56-5
• Molecular Formula: C₂₇H₄₄O₆
• Molecular Weight: 464.643
• UNII: 84986BG3NG
• DSSTox Substance ID: DTXSID0040595
• Nikkaji Number: J15.367B
• Wikidata: Q27103520
• Metabolomics Workbench ID: 34485
• ChEMBL ID: CHEMBL549789
• Mol file: 13408-56-5.mol

Synonyms:2 beta,3 beta,14,20,22-pentahydroxy-5 beta- cholest-7-en-6-one;25-deoxy-20-ecdysone;25-deoxyecdysterone;25d20E;ponasterone A;ponasterone A, ponasterone B (2alpha,3alpha,5beta,22R)-isomer

Chemical Property of Ponasterone A

Chemical Property:

• Appearance/Colour: White Solid
• Vapor Pressure: 4.19E-19mmHg at 25°C
• Melting Point: 259-260° (dec)
• Refractive Index: 1.582
• Boiling Point: 640.5 °C at 760 mmHg
• PKA: 14.13±0.70(Predicted)
• Flash Point: 355.2 °C
• PSA: 118.22000
• Density: 1.22 g/cm³
• LogP: 2.73910
• Storage Temp.: −20°C
• Solubility.: Methanol (Slightly, Sonicated), Pyridine (Slightly)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 464.31378912
• Heavy Atom Count: 33
• Complexity: 823

Purity/Quality:

98%,99%, ^*data from raw suppliers

Ponasterone A ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)CCC(C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)O)O
• Isomeric SMILES: CC(C)CC[C@H]([C@@](C)([C@H]1CC[C@@]2([C@@]1(CC[C@H]3C2=CC(=O)[C@H]4[C@@]3(C[C@@H]([C@@H](C4)O)O)C)C)O)O)O
• Uses: Ponasterone A is an Ecdysone analog. Ponasterone A has been used to induce the expression of human huntingtin (HTT).

Technology Process of Ponasterone A

There total 9 articles about Ponasterone A 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: 91.0%

25,26-didehydroponasterone A (82413-55-6) → ponasterone A (13408-48-5,19338-77-3,78148-78-4,13408-56-5)

Guidance literature:

With sodium nitrite; palladium on activated charcoal; In ethanol; water; for 0.5h; under 760 Torr;

DOI:10.1016/S0040-4020(02)00580-X

Reference yield: 90.0%

Stachysterone C (26362-25-4) → ponasterone A (13408-48-5,19338-77-3,78148-78-4,13408-56-5)

Guidance literature:

With sodium nitrite; palladium on activated charcoal; In ethanol; water; for 0.416667h; under 760 Torr;

DOI:10.1016/S0040-4020(02)00580-X

Reference yield: 24.0%

2,3:20,22-di-O-isopropylideneponasterone A (14188-76-2) → ponasterone A (13408-48-5,19338-77-3,78148-78-4,13408-56-5) + 20,22-acetonide of ponasterone A

Guidance literature:

2,3:20,22-di-O-isopropylideneponasterone A; With acetic acid; at 20 ℃; for 1.5h;

With zinc(II) chloride; at 20 ℃; for 5h;

DOI:10.1023/A:1016547122573

upstream raw materials:

Stachysterone C

25,26-didehydroponasterone A

2,3:20,22-di-O-isopropylideneponasterone A

20-hydroxyecdysone-2,3,22-triacetate

Downstream raw materials:

20-Hydroxyecdysone

inokosterone

25-deoxy-20-hydroxyecdyson-26-oic acid

20-hydroxyecdyson-26-oic acid

Refernces

• 1、 Harmatha, Juraj,Budesinsky, Milos,Vokac, Karel,Dinan, Laurence,Lafont, Rene. "Dimeric ecdysteroid analogues and their interaction with the Drosophila ecdysteroid receptor". . p. 1229 - 1238. Retrieved 2008/03/28.
• 2、 Suksamrarn, Apichart,Tanachatchairatana, Tanud,Sirigarn, Chana. "Stereoselective catalytic hydrogenation of Δ7-6-ketosteroids in the presence of sodium nitrite". . p. 6033 - 6037. Retrieved 2007/10/03.