20-O-Acetylingenol-3-angelate

Base Information

• Chemical Name: 20-O-Acetylingenol-3-angelate
• CAS No.: 82425-35-2
• Molecular Formula: C₂₇H₃₆O₇
• Molecular Weight: 472.579
• Mol file: 82425-35-2.mol

Synonyms:

Chemical Property of 20-O-Acetylingenol-3-angelate

Chemical Property:

• PSA: 110.13000
• LogP: 2.90310

Purity/Quality:

98% ^*data from raw suppliers

20-O-Acetylingenol-3-angelate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 20-O-Acetylingenol-3-angelate is a molluscicidal agent present in extracts from Euphorbia conspicua N. E. Br. Anti-cancer agent. Cytostatic agent.

Technology Process of 20-O-Acetylingenol-3-angelate

There total 3 articles about 20-O-Acetylingenol-3-angelate 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: 100.0%

vinyl acetate (108-05-4,9003-20-7) + ingenol mebutate (75567-37-2,849146-39-0) → ingenol 20-acetate-3-angelate (82425-35-2)

Guidance literature:

With Candida antarctica lipase B (Novozyme 435); In tert-Amyl alcohol; at 37 ℃; for 7h; regioselective reaction; Enzymatic reaction;

DOI:10.1016/j.fitote.2009.02.001

Reference yield: 88.0%

acetic anhydride (108-24-7) + ingenol mebutate (75567-37-2,849146-39-0) → ingenol 20-acetate-3-angelate (82425-35-2)

Guidance literature:

With triethylamine; In dichloromethane;

DOI:10.1016/j.bmcl.2013.08.038

Reference yield:

3-O-angeloyl-5,20-O-isopropylideneingenol (87980-68-5) → ingenol 20-acetate-3-angelate (82425-35-2)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride / water

2: triethylamine / dichloromethane

With hydrogenchloride; triethylamine; In dichloromethane; water;

DOI:10.1016/j.bmcl.2013.08.038

upstream raw materials:

acetic anhydride

ingenol mebutate

vinyl acetate

3-O-angeloyl-5,20-O-isopropylideneingenol

Refernces

• 1、 Liang, Xifu,Grue-Sorensen, Gunnar,Mansson, Kristoffer,Vedso, Per,Soor, Anke,Stahlhut, Martin,Bertelsen, Malene,Engell, Karen Margrethe,Hoegberg, Thomas. "Syntheses, biological evaluation and SAR of ingenol mebutate analogues for treatment of actinic keratosis and non-melanoma skin cancer". . p. 5624 - 5629. Retrieved 2013/10/01.