13408-56-5

Basic information

• Product Name: PONASTERONE A
• Synonyms: PONASTERONE A;2B,3B,14A,20R,22R-PENTAHYDROXY-5B-CHOLEST-7-EN-6-ONE;2BETA, 3BETA, 14ALPHA, 20R,22R-PENTAHYDROXY-5BETA-CHOLEST-7-EN-6-ONE;25-DEOXY-20-HYDROXYECDYSONE;25-DEOXYECDYSTERONE;2β,3β,14α,20r,22r-pentahydroxy-5β-cholest-7-en-6-one;25-Deoxy-20-hydroxyecdysone, 25-Deoxyecdysterone, 2β,3β,14α,20R,22R-Pentahydroxy-5β-cholest-7-en-6-one;(20R,22R)-2β,3β,14,20,22-Pentahydroxy-5β-cholesta-7-ene-6-one
• CAS NO: 13408-56-5
• Molecular Formula: C₂₇H₄₄O₆
• Molecular Weight: 464.63
• Product Categories: Steroids
• Mol File: 13408-56-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: 259-260° (dec)
• Boiling Point: 640.5 °C at 760 mmHg
• Flash Point: 355.2 °C
• Appearance: White Solid
• Density: 1.22 g/cm³
• Vapor Pressure: 4.19E-19mmHg at 25°C
• Refractive Index: 1.582
• Storage Temp.: −20°C
• Solubility: Methanol (Slightly, Sonicated), Pyridine (Slightly)
• PKA: 14.13±0.70(Predicted)
• CAS DataBase Reference: PONASTERONE A(CAS DataBase Reference)
• NIST Chemistry Reference: PONASTERONE A(13408-56-5)
• EPA Substance Registry System: PONASTERONE A(13408-56-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 13408-56-5(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 13408-56-5 differently. You can refer to the following data:
1. Ponasterone A is an Ecdysone analog.
2. Ponasterone A has been used to induce the expression of human huntingtin (HTT).

Biochem/physiol Actions

Ponasterone A is an analogue of ecdysone.

InChI:InChI=1/C27H44O6/c1-15(2)6-7-23(31)26(5,32)22-9-11-27(33)17-12-19(28)18-13-20(29)21(30)14-24(18,3)16(17)8-10-25(22,27)4/h12,15-16,18,20-23,29-33H,6-11,13-14H2,1-5H3/t16-,18-,20+,21-,22-,23+,24+,25+,26+,27+/m0/s1

Upstream product

• 84507-66-4 20-hydroxyecdysone 2,3:20,22-diacetonide 
• 19404-87-6 20-hydroxyecdysone-2,3,22-triacetate 
• 14188-76-2 2,3:20,22-di-O-isopropylideneponasterone A 
• 82413-55-6 25,26-didehydroponasterone A 
• 26362-25-4 Stachysterone C 

Downstream Products

• 5289-74-7 20-Hydroxyecdysone 
• 88980-54-5 inokosterone 
• 59971-16-3 25-deoxy-20-hydroxyecdyson-26-oic acid 
• 86583-58-6 20-hydroxyecdyson-26-oic acid 
• 19458-46-9 20,26-dihydroxyecdysone 

Related news

Biosynthesis of PONASTERONE A (cas 13408-56-5) and ecdysterone from cholesterol in Podocarpus macrophyllus08/02/2019

Administration of cholesterol-4-14C to Podocarpus macrophyllus seedlings resulted in the formation of the insect-metamorphosing substances ponasterone A and ecdysterone in radioactive form.detailed

The uptake and release of PONASTERONE A (cas 13408-56-5) by the Kc cell line of Drosophila melanogaster07/30/2019

The association of ponasterone A (PNA) and 20-hydroxyecdysone with Kc cells is commensurate with their biological activity on this Kc cell line, the physiological activity ratio for PNA, 20-hydroxyecdysone and ecdysone is 1:50:2000, resp. Both association and release of [3H]-PNA are temperature-...detailed

Synthesis of PONASTERONE A (cas 13408-56-5) derivatives with various steroid skeleton moieties and evaluation of their binding to the ecdysone receptor of Kc cells07/26/2019

A series of ponasterone A (PNA) derivatives with various steroid moieties were synthesized to measure their binding activity to the ecdysone receptors of Drosophila Kc cells. The activity of compounds was evaluated by determining the concentration required to give the 50% inhibition (IC50 in M) ...detailed

Relevant articles and documents

Efficient synthesis of ponasterone A by recombinant Escherichia coli harboring the glycosyltransferase GTBP1 with in situ product removal

A glycosyltransferase GTBP1 from Bacillus pumilus BF1 was isolated. Efficient production of ponasterone A was achieved by the recombinant E. coli/gtBP1 in a biphasic system with a molar yield of 92.7%. This in situ product removal provided the driving force for shifting the reaction equilibrium towards the synthesis of the product.

C-25 epimeric 26-haloponasterone A: Synthesis, absolute configuration and moulting activity

A convenient synthesis of inokosterone has been accomplished. Inokosterone exists as two C-25 epimers, which could be separated from each other through their diacetonide derivatives. The absolute configuration of these compounds was determined. Two C-25 epimers of 26-chloroponasterone A were synthesized from the respective C-25 epimeric inokosterone. Two epimeric 26-bromo and 26-iodoponasterone A compounds were also synthesized. Moulting activity of these compounds was evaluated using the Musca bioassay, and it was found that the (25S)-26-halo analogues were more active than the corresponding (25R)-26-halo analogues. Among the 25S series, an increase in activity with an increase in size of the halogen atom was observed, indicating that the steric factor was more important than the electronic factor in binding of these ecdysteroid analogues to the receptor. On the other hand, a decrease in activity with an increase in size of the halogen atom was noted in the 25R series, suggesting that the steric factor was less important than the electronic factor. The results indicated that the configuration at C-25 and the substituent at C-26 have significant influences on the interaction of ecdysteroids with their receptor.

Stereoselective catalytic hydrogenation of Δ7-6-ketosteroids in the presence of sodium nitrite

Catalytic hydrogenation with Pd-C as a catalyst in the presence of sodium nitrite is a simple, convenient and high yielding stereoselective reduction of olefinic function of Δ7-6-ketosteroids to the corresponding dihydro analogues.