Isoannonacin

Base Information

• Chemical Name: Isoannonacin
• CAS No.: 123266-22-8
• Molecular Formula: C₃₅H₆₄O₇
• Molecular Weight: 596.889
• NSC Number: 618571
• DSSTox Substance ID: DTXSID50937857
• Wikidata: Q57617619
• Metabolomics Workbench ID: 75595
• ChEMBL ID: CHEMBL446074
• Mol file: 123266-22-8.mol

Synonyms:annonacin-A-one;annonacin-A-one, ((2,4-cis)-10R)-isomer

Chemical Property of Isoannonacin

Chemical Property:

• PSA: 113.29000
• LogP: 7.34940
• XLogP3: 8.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 26
• Exact Mass: 596.46520438
• Heavy Atom Count: 42
• Complexity: 714

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCC(C1CCC(O1)C(CCCCC(CCCCCC2CC(C(=O)O2)CC(=O)C)O)O)O

Technology Process of Isoannonacin

There total 3 articles about Isoannonacin 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: 75.0%

Annonacine → isoannonacin (123266-22-8)

Guidance literature:

With sodium hydroxide; In methanol; Reflux;

DOI:10.1002/pca.2700

Reference yield:

annonacin A (129212-95-9,129212-96-0,152985-32-5) → isoannonacin (123266-22-8)

Guidance literature:

With potassium hydroxide; In tert-butyl alcohol;

DOI:10.1021/jo00284a006

Reference yield:

annonacinone (123266-21-7) → isoannonacin (123266-22-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 40 percent / NaBH₄

2: KOH / 2-methyl-propan-2-ol

With potassium hydroxide; sodium tetrahydroborate; In tert-butyl alcohol;

DOI:10.1021/jo00284a006

upstream raw materials:

annonacin A

annonacinone

Refernces

• 1、 Laboureur, Laurent,Bonneau, Natacha,Champy, Pierre,Brunelle, Alain,Touboul, David. "Structural Characterisation of Acetogenins from Annona muricata by Supercritical Fluid Chromatography Coupled to High-Resolution Tandem Mass Spectrometry". . p. 512 - 520. Retrieved 2017.