20-Hydroxyecdysone 22-acetate

Base Information

• Chemical Name: 20-Hydroxyecdysone 22-acetate
• CAS No.: 22799-02-6
• Molecular Formula: C29H46 O8
• Molecular Weight: 522.67
• ChEMBL ID: CHEMBL2087165
• DSSTox Substance ID: DTXSID90575676
• Nikkaji Number: J528.455D
• Wikidata: Q82465092
• Mol file: 22799-02-6.mol

Synonyms:20-Hydroxyecdysone 22-acetate;22799-02-6;[(2R,3R)-2,6-dihydroxy-6-methyl-2-[(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]heptan-3-yl] acetate;CHEMBL2087165;DTXSID90575676;J-014861;(2beta,3beta,5beta,22R)-2,3,14,20,25-Pentahydroxy-6-oxocholest-7-en-22-yl acetate

Chemical Property of 20-Hydroxyecdysone 22-acetate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.58
• Boiling Point: 707.054°C at 760 mmHg
• Flash Point: 226.851°C
• PSA: 144.52000
• Density: 1.266g/cm³
• LogP: 2.42480
• Storage Temp.: −20°C
• XLogP3: 1
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 522.31926842
• Heavy Atom Count: 37
• Complexity: 975

Purity/Quality:

99%min ^*data from raw suppliers

20-Hydroxyecdysone22-acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC(CCC(C)(C)O)C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)O
• Isomeric SMILES: CC(=O)O[C@H](CCC(C)(C)O)[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
• Uses: 20-Hydroxyecdysone 22-Acetate is used in the preparation of steroidal ligands and their use in gene switch modulation.

Technology Process of 20-Hydroxyecdysone 22-acetate

There total 6 articles about 20-Hydroxyecdysone 22-acetate 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: 93.0%

20-hydroxyecdysone 22-acetate 2,3-acetonide (169901-90-0) → 20-Hydroxyecdysone-22-acetate (22799-02-6)

Guidance literature:

With acetic acid; for 2h;

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

Reference yield: 6.0%

20-Hydroxyecdysone (5289-74-7) + acetic anhydride (108-24-7) → 20-Hydroxyecdysone-2-acetate (19536-25-5) + 20-Hydroxyecdysone-22-acetate (22799-02-6) + 20-hydroxyecdysone 2,3-diacetate (22799-03-7) + 20-Hydroxyecdysone-3-acetate (22961-68-8)

Guidance literature:

With pyridine; In chloroform; for 5.5h; Further byproducts given;

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

Reference yield: 6.0%

20-Hydroxyecdysone (5289-74-7) + acetic anhydride (108-24-7) → 20-Hydroxyecdysone-2-acetate (19536-25-5) + 20-Hydroxyecdysone-22-acetate (22799-02-6) + 20-hydroxyecdysone 2,3-diacetate (22799-03-7) + 20-hydroxyecdysone 3,22-diacetate

Guidance literature:

With pyridine; In chloroform; for 5.5h; Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;

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

upstream raw materials:

20-Hydroxyecdysone

acetic anhydride

20-hydroxyecdysone 22-acetate 2,3-acetonide

ecdysterone 2,3-monoacetonide

Downstream raw materials:

C₃₅H₅₀O₁₀S

2-Deoxy-20-hydroxyecdysone-22-benzoate

Refernces

• 1、 Suksamrarn, Apichart,Pattanaprateep, Prasert. "Selective Acetylation of 20-Hydroxyecdysone. Partial Synthesis of Some Minor Ecdysteroids and Analogues". . p. 10633 - 10650. Retrieved 2007/10/02.