ingenol 3-benzoate

Base Information

• Chemical Name: ingenol 3-benzoate
• CAS No.: 83036-64-0
• Molecular Formula: C₂₇H₃₂O₆
• Molecular Weight: 452.547
• Mol file: 83036-64-0.mol

Synonyms:ingenol 3-benzoate

Chemical Property of ingenol 3-benzoate

Chemical Property:

Purity/Quality:

≥98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ingenol 3-benzoate

There total 5 articles about ingenol 3-benzoate 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: 42.0%

ingenol (30220-46-3) + benzoic acid (65-85-0,8013-63-6) → Ingenol-3-benzoate (83036-64-0) + Ingenol dibenzoate (59086-90-7)

Guidance literature:

With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; at -18 ℃; for 72h;

DOI:10.1002/(SICI)1099-0690(199912)1999:12<3413::AID-EJOC3413>3.0.CO;2-S

Reference yield:

C30H36O6 → Ingenol-3-benzoate (83036-64-0)

Guidance literature:

With perchloric acid; In methanol; for 0.75h; Yield given;

Reference yield:

(6S,6aR,7aR,9R,9aS,12S,12aR,12bR)-12,12a-dihydroxy-2,2,7,7,9,11-hexamethyl-4,6,6a,7,7a,8,9,12,12a,12b-decahydro-6,9a-methanocyclopenta[9,10]cyclopropa[5,6]cyclodeca[1,2-d][1,3]dioxin-13-one (77573-43-4) → Ingenol-3-benzoate (83036-64-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 4-(N,N-dimethylamino)pyridine / toluene / 2 h

2: 70 percent HClO₄ / methanol / 0.75 h

With dmap; perchloric acid; In methanol; toluene;

upstream raw materials:

ingenol

benzoic acid

benzoyl chloride

(6S,6aR,7aR,9R,9aS,12S,12aR,12bR)-12,12a-dihydroxy-2,2,7,7,9,11-hexamethyl-4,6,6a,7,7a,8,9,12,12a,12b-decahydro-6,9a-methanocyclopenta[9,10]cyclopropa[5,6]cyclodeca[1,2-d][1,3]dioxin-13-one

Downstream raw materials:

Ingenol dibenzoate

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.
• 2、 Sorg, Bernd,Hecker, Erich. "On the Chemistry of Ingenol, II. Esters of Ingenol and δ7,8-Isoingenol". . p. 748 - 756. Retrieved 2007/10/02.