20-deoxyingenol

Base Information

• Chemical Name: 20-deoxyingenol
• CAS No.: 54706-99-9
• Molecular Formula: C20H28O4
• Molecular Weight: 332.44
• Mol file: 54706-99-9.mol

Synonyms:1H-2,8a-Methanocyclopenta[a]cyclopropa[e]cyclodecen-11-one, 1a,2,5,5a,6,9,10,10a-octahydro-5,5a,6-trihydroxy-1,1,4,7,9-pentamethy l-, (1aR,2S,5R,5aS,6S,8aS,9R,10aR)-;

Chemical Property of 20-deoxyingenol

Chemical Property:

• Melting Point: 208-209℃ (分解)
• Boiling Point: 470.5±45.0 °C(Predicted)
• PKA: 12.21±0.70(Predicted)
• PSA: 77.76000
• Density: 1.26±0.1 g/cm3 (20 ºC 760 Torr)
• LogP: 1.84280

Purity/Quality:

98%,99%, ^*data from raw suppliers

20-deoxyingenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 20-Deoxyingenol is a diterpene derivative of Ingenol (I655795), the analogue of Ingenol 3-Angelate (I655800), which has anti-tumor activity when used topically for the treatment of actinic keratosis.

Technology Process of 20-deoxyingenol

There total 48 articles about 20-deoxyingenol 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: 92.0%

3,4-O-isopropylidene-20-deoxyingenol (91413-76-2) → (1aR,2S,5R,5aS,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-1,1,4,7,9-pentamethyl-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one (54706-99-9)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 20 ℃; for 5h;

DOI:10.1021/ja044123l

Reference yield: 82.0%

5-O-benzoyl-20-deoxyingenol → (1aR,2S,5R,5aS,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-1,1,4,7,9-pentamethyl-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one (54706-99-9)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 3h;

DOI:10.1016/j.ejmech.2018.07.020

Reference yield: 81.0%

(3S,3aS,6aR,7S,8R,9R,9aR,10aR,12R,12aS)-8-hydroxy-2,7,10,10,12pentamethyl-5,13-dioxo-6a,7,9,9a,10,10a,11,12-octahydro-3H,8H-9,12a-methanocyclopenta[1,10]cyclopropa[6,7]cyclodeca[1,2-d][1,3 ]dioxol-3-yl acetate (1453222-07-5) → (1aR,2S,5R,5aS,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-1,1,4,7,9-pentamethyl-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one (54706-99-9)

Guidance literature:

(3S,3aS,6aR,7S,8R,9R,9aR,10aR,12R,12aS)-8-hydroxy-2,7,10,10,12pentamethyl-5,13-dioxo-6a,7,9,9a,10,10a,11,12-octahydro-3H,8H-9,12a-methanocyclopenta[1,10]cyclopropa[6,7]cyclodeca[1,2-d][1,3 ]dioxol-3-yl acetate; With Martins sulfurane; In chloroform; at 60 ℃; for 3h; Inert atmosphere;

With sodium hydroxide; In tetrahydrofuran; water; for 1h; Inert atmosphere;

DOI:10.1021/ja501881p

upstream raw materials:

3-O-angeloyl-20-deoxyingenol

3,4-O-isopropylidene-20-deoxyingenol

C₂₃H₃₂O₅

C₂₈H₃₄O₄

Downstream raw materials:

ingenol

3-tigloyl-20-deoxyingenol

3-O-angeloyl-20-deoxyingenol

Refernces

• 1、 Uemura et al.. "". . p. 2527. Retrieved 1974.
• 2、 McKerrall, Steven J.,J?rgensen, Lars,Kuttruff, Christian A.,Ungeheuer, Felix,Baran, Phil S.. "Development of a concise synthesis of (+)-ingenol". supporting information. p. 5799 - 5810. Retrieved 2014/05/06.
• 3、 Jorgensen, Lars,McKerrall, Steven J.,Kuttruff, Christian A.,Ungeheuer, Felix,Felding, Jakob,Baran, Phil S.. "14-Step synthesis of (+)-ingenol from (+)-3-carene". . p. 878 - 882. Retrieved 2013/09/12.