Amorphigenin

Base Information

• Chemical Name: Amorphigenin
• CAS No.: 4208-09-7
• Molecular Formula: C₂₃H₂₂O₇
• Molecular Weight: 410.423
• DSSTox Substance ID: DTXSID70962267
• Nikkaji Number: J15.134C
• Wikidata: Q63396516
• ChEMBL ID: CHEMBL465552
• Mol file: 4208-09-7.mol

Synonyms:8'-hydroxyrotenone;amorphigenin

Chemical Property of Amorphigenin

Chemical Property:

• Vapor Pressure: 7.05E-16mmHg at 25°C
• Melting Point: 191-192 °C
• Boiling Point: 612.9°Cat760mmHg
• PKA: 14.43±0.10(Predicted)
• Flash Point: 215.2°C
• PSA: 83.45000
• Density: 1.333g/cm³
• LogP: 2.67570
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 410.13655304
• Heavy Atom Count: 30
• Complexity: 681

Purity/Quality:

99% ^*data from raw suppliers

AMORPHIGENIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C2C(=C1)C3C(CO2)OC4=C(C3=O)C=CC5=C4CC(O5)C(=C)CO)OC
• Isomeric SMILES: COC1=C(C=C2C(=C1)[C@H]3[C@@H](CO2)OC4=C(C3=O)C=CC5=C4C[C@@H](O5)C(=C)CO)OC

Technology Process of Amorphigenin

There total 18 articles about Amorphigenin 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: 73.0%

amorphigenin acetate enol acetate (142050-36-0) → amorphigenin (4208-09-7)

Guidance literature:

With hydrogenchloride; In methanol; for 2h; Heating;

Reference yield: 67.0%

(6aS,12aS,5'R)-amorphigenin enol acetate → amorphigenin (4208-09-7)

Guidance literature:

With hydrogenchloride; In methanol; for 2h; Heating;

Reference yield: 33.0%

rotenone (83-79-4) → amorphigenin (4208-09-7)

Guidance literature:

rotenone; With N-phenylselanylphthalimide; (1S)-10-camphorsulfonic acid; water; In dichloromethane; at 20 ℃; for 72h; Inert atmosphere; Darkness;

With dihydrogen peroxide; In pyridine; water; at 0 - 20 ℃; for 2h;

DOI:10.1021/acs.jnatprod.9b01224

upstream raw materials:

sodium [1,2-13C₂]acetate

amorphigenin acetate enol acetate

amorphin

(6aS,12aS,5′R)-rotenone-6′-norketone

Downstream raw materials:

rotenonic acid

Refernces

• 1、 Russell, David A.,Bridges, Hannah R.,Serreli, Riccardo,Kidd, Sarah L.,Mateu, Natalia,Osberger, Thomas J.,Sore, Hannah F.,Hirst, Judy,Spring, David R.. "Hydroxylated Rotenoids Selectively Inhibit the Proliferation of Prostate Cancer Cells". . p. 1829 - 1845. Retrieved 2020/06/05.
• 2、 Crombie, Leslie,Holden, Ian,Kilbee, Geoffrey W.,Whiting, Donald A.. "Biosynthesis of Rotenoids by Amorpha fruticosa: Sequence, Specificity, and Stereochemistry in the Development of the Hemiterpenoid Segment". . p. 789 - 798. Retrieved 2007/10/02.