ECDYSONE-2-ACETATE, BETA-(SH)

Base Information

• Chemical Name: ECDYSONE-2-ACETATE, BETA-(SH)
• CAS No.: 19536-25-5
• Molecular Formula: C29H46O8
• Molecular Weight: 522.67
• Mol file: 19536-25-5.mol

Synonyms:ECDYSONE-2-ACETATE, BETA-(SH)

Chemical Property of ECDYSONE-2-ACETATE, BETA-(SH)

Chemical Property:

• Melting Point: 218-220 °C
• Boiling Point: 707.3±60.0 °C(Predicted)
• PKA: 13.96±0.70(Predicted)
• PSA: 144.52000
• Density: 1.26±0.1 g/cm3(Predicted)
• LogP: 2.42480

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

2-O-Acetyl-20-hydroxyecdysone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: 2-O-Acetyl-20-hydroxyecdysone is an ecdysone steroid hormone that has been found in plants and animals. It completely inhibits the growth of the bacteria S. aureus, E. coli, and P. vulgaris, as well as the fungi C. albicans, A. alternata, and F. solani when used at a concentration of 10 μg/ml. 2-O-Acetyl-20-hydroxyecdysone (50 μM) increases aggregation of amyloid-β (1-42) (Aβ42), increases fibril formation by 60%, and decreases oligomer levels in cell-free assays. It reduces Aβ42-induced cytotoxicity of SH-SY5Y cells when used at concentrations of 5 and 10 μM.

Technology Process of ECDYSONE-2-ACETATE, BETA-(SH)

There total 8 articles about ECDYSONE-2-ACETATE, BETA-(SH) 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: 90.0%

vinyl acetate (108-05-4,9003-20-7) + 20-Hydroxyecdysone (5289-74-7) → 20-Hydroxyecdysone-2-acetate (19536-25-5)

Guidance literature:

In pyridine; tert-Amyl alcohol; at 45 ℃; for 168h; Candida antarctica lipase B supported on acrylic resin (Novozym 435);

DOI:10.1016/S0040-4020(97)00245-7

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:

2β,3β,14,20,22α_F,25-hexahydroxy-(5β)-cholest-7-en-6-one

acetic anhydride

20-hydroxyecdysone

20-Hydroxyecdysone

Refernces

• 1、 Danieli, Bruno,Lesma, Giordano,Luisetti, Monica,Rivo, Sergio. "Candida antarctica lipase B catalyzes the regioselective esterification of ecdysteroids at the C-2 OH". . p. 5855 - 5862. Retrieved 1997.
• 2、 Suksamrarn, Apichart,Pattanaprateep, Prasert. "Selective Acetylation of 20-Hydroxyecdysone. Partial Synthesis of Some Minor Ecdysteroids and Analogues". . p. 10633 - 10650. Retrieved 2007/10/02.