Ingenol

Base Information

• Chemical Name: Ingenol
• CAS No.: 30220-46-3
• Molecular Formula: C20H28O5
• Molecular Weight: 348.439
• Hs Code.: 2914409000
• European Community (EC) Number: 636-889-2
• UNII: IC77UZI9G8
• Nikkaji Number: J315.813F
• Wikidata: Q27106930
• Metabolomics Workbench ID: 53228
• ChEMBL ID: CHEMBL2165402
• Mol file: 30220-46-3.mol

Synonyms:ingenol

Chemical Property of Ingenol

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 153 °C
• Refractive Index: 1.625
• Boiling Point: 523.785 °C at 760 mmHg
• PKA: 12.06±0.70(Predicted)
• Flash Point: 284.654 °C
• PSA: 97.99000
• Density: 1.33 g/cm³
• LogP: 0.81520
• Storage Temp.: −20°C
• Solubility.: DMSO: soluble
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 348.19367399
• Heavy Atom Count: 25
• Complexity: 707

Purity/Quality:

95%-98% ^*data from raw suppliers

Ingenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 38-41
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2C(C2(C)C)C3C=C(C(C4(C1(C3=O)C=C(C4O)C)O)O)CO
• Isomeric SMILES: C[C@@H]1C[C@@H]2[C@@H](C2(C)C)[C@@H]3C=C([C@H]([C@]4([C@@]1(C3=O)C=C([C@@H]4O)C)O)O)CO
• Description: Ingenol is a diterpenoid related to phorbol, derived from the milkweed plant E. peplus.1 It is a protein kinase C activator that displays a Ki value of 30 μM and an ED50 value of 27 μM in vitro. Most ingenol esters are tumor-promoting. However, ingenol mebutate possesses anti-tumor activity when used topically for actinic keratosis. Ingenol is a diterpenoid related to phorbol, derived from the milkweed plant E. peplus. It is a protein kinase C activator that displays a Ki value of 30 μM and an ED50 value of 27 μM in vitro. Most ingenol esters are tumor-promoting. However, ingenol mebutate possesses anti-tumor activity when used topically for actinic keratosis.
• Uses: Ingenol, is the analogue of Ingenol 3-Angelate (I655800), which has anti-tumor activity when used topically for the treatment of actinic keratosis.

Technology Process of Ingenol

There total 62 articles about Ingenol 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: 76.0%

(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) → ingenol (30220-46-3)

Guidance literature:

With selenium(IV) oxide; formic acid; In 1,4-dioxane; at 80 ℃; for 1.25h;

DOI:10.1126/science.1241606

Reference yield: 74.0%

ingenol monoacetate (64280-37-1) → ingenol (30220-46-3)

Guidance literature:

With potassium hydroxide; In methanol; water; at 0 - 20 ℃; Temperature; Solvent; Inert atmosphere;

DOI:10.1016/j.tetlet.2017.02.078

Reference yield:

20-O-acetylingenol-3-O-(2E,4Z)-decadienoate (158850-76-1,466663-12-7) → ingenol (30220-46-3)

Guidance literature:

With acetic acid; In tetrahydrofuran; at 120 ℃; for 3h;

DOI:10.3390/molecules24203806

upstream raw materials:

C₄₃H₄₇N₃O₉

ingenol 3-(2,4,6,8,10)-tetradecapentaenoate

ingenol 3,5,20-triacetate

(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 3,5,20-triacetate

ingenol 20-trityl ether

Ingenol dibenzoate

ingenol-3,4:5,20-diacetonide

Refernces

• 1、 McKerrall, Steven J.,J?rgensen, Lars,Kuttruff, Christian A.,Ungeheuer, Felix,Baran, Phil S.. "Development of a concise synthesis of (+)-ingenol". . p. 5799 - 5810. Retrieved 2014.
• 2、 Pospí?il, Ji?í,Béres, Tibor,Strnad, Miroslav. "A convenient method for the preparation of 20-[18O]-labeled ingenol". . p. 1421 - 1424. Retrieved 2017.
• 3、 -. "A CONTINUOUS FLOW PROCESS FOR THE PREPARATION OF INGENOL-3-MEBUTATE". Paragraph 0088-0091. . Retrieved 2015/12/08.