Ecdysterone 20,22-monoacetonide

Base Information

• Chemical Name: Ecdysterone 20,22-monoacetonide
• CAS No.: 22798-96-5
• Molecular Formula: C₃₀H₄₈O₇
• Molecular Weight: 520.707
• DSSTox Substance ID: DTXSID501346563
• Nikkaji Number: J416.586A
• Wikidata: Q105023223
• ChEMBL ID: CHEMBL2087536
• Mol file: 22798-96-5.mol

Synonyms:Ecdysterone 20,22-monoacetonide;22798-96-5;20-Hydroxyecdysone 20,22-acetonide;CHEMBL2087536;DTXSID501346563;STL564977;AKOS037623238;FS-9622;(22R)-2beta,3beta,14,25-Tetrahydroxy-20,22-(isopropylidenedioxy)-5beta-cholest-7-en-6-one;(2beta,3beta,5beta,17beta)-2,3,14-trihydroxy-17-[(4R,5R)-5-(3-hydroxy-3-methylbutyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl]androst-7-en-6-one

Chemical Property of Ecdysterone 20,22-monoacetonide

Chemical Property:

• Melting Point: 222 °C
• Boiling Point: 641.0±55.0 °C(Predicted)
• PKA: 13.92±0.70(Predicted)
• PSA: 116.45000
• Density: 1.23±0.1 g/cm3(Predicted)
• LogP: 3.65230
• XLogP3: 2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 520.34000387
• Heavy Atom Count: 37
• Complexity: 988

Purity/Quality:

Analysis control,HPLC≥98% ^*data from raw suppliers

Ecdysterone20,22-monoacetonide 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC(C(O1)(C)C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)O)CCC(C)(C)O)C
• Isomeric SMILES: C[C@]12CC[C@H]3C(=CC(=O)[C@H]4[C@@]3(C[C@@H]([C@@H](C4)O)O)C)[C@@]1(CC[C@@H]2[C@@]5([C@H](OC(O5)(C)C)CCC(C)(C)O)C)O

Technology Process of Ecdysterone 20,22-monoacetonide

There total 12 articles about Ecdysterone 20,22-monoacetonide 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: 97.0%

20-Hydroxyecdysone (5289-74-7) + acetone (67-64-1) → 20-hydroxyecdysone 20,22-acetonide (84507-68-6,22798-96-5)

Guidance literature:

With tetrafluoroboric acid; at 25 ℃; for 0.166667h;

DOI:10.1023/A:1022433423370

Reference yield: 48.0%

20-hydroxyecdysone 2,3:20,22-diacetonide (84507-66-4,22798-98-7) → 20-hydroxyecdysone 20,22-acetonide (84507-68-6,22798-96-5) + podecdysone B 20,22-acetonide (650140-19-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In chloroform; at 20 ℃; for 168h;

DOI:10.1023/B:RUJO.0000003183.84168.79

Reference yield: 38.0%

20-Hydroxyecdysone (5289-74-7) + acetone (67-64-1) → ecdysterone 2,3-monoacetonide (84507-67-5,113866-76-5) + 20-hydroxyecdysone 20,22-acetonide (84507-68-6,22798-96-5)

Guidance literature:

With pyridinium p-toluenesulfonate; In methanol; for 3h;

DOI:10.1016/0040-4020(95)00635-L

upstream raw materials:

20-hydroxyecdysone-2,3:20,22-diacetonide

20-Hydroxyecdysone

acetone

20-hydroxyecdysone 2,3:20,22-diacetonide

Downstream raw materials:

20-hydroxyecdysone

14-dehydro-20-hydroxyecdysone

20-Hydroxyecdysone

2,3-O-[2-(6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl)ethylidene]-20,22-O-isopropylidenestachysterone

Refernces

• 1、 Bobaev,Zavarzin,Blinnikov,Bobakulov, Kh. M.,Ramazanov, N. Sh.,Abdullaev. "Synthesis of 20-Hydroxyecdysone Carboxylate Esters". . p. 1088 - 1092. Retrieved 2017/12/04.
• 2、 Martins, Ana,Csabi, Jozsef,Balazs, Attila,Kitka, Diana,Amaral, Leonard,Molnar, Jozsef,Simon, Andras,Toth, Gabor,Hunyadi, Attila. "Synthesis and structure-activity relationships of novel ecdysteroid dioxolanes as MDR modulators in cancer". . p. 15255 - 15275. Retrieved 2014/01/17.