Mitraphylline

Base Information

• Chemical Name: Mitraphylline
• CAS No.: 509-80-8
• Molecular Formula: C21H24N2O4
• Molecular Weight: 368.433
• European Community (EC) Number: 208-106-0
• NSC Number: 717700
• UNII: 1H9SRL2456
• DSSTox Substance ID: DTXSID50198926
• Nikkaji Number: J12.205J
• Wikipedia: Mitraphylline
• Wikidata: Q10859059
• Metabolomics Workbench ID: 126911
• ChEMBL ID: CHEMBL2135897
• Mol file: 509-80-8.mol

Synonyms:methyl (19alpha)-19-methyl-2-oxoformosanan-16-carboxylate;mitraphylline

Chemical Property of Mitraphylline

Chemical Property:

• Melting Point: 265～266℃
• Boiling Point: 555.2 °C at 760 mmHg
• PKA: 13.56±0.60(Predicted)
• Flash Point: 289.6 °C
• PSA: 67.87000
• Density: 1.33 g/cm³
• LogP: 2.13840
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 368.17360725
• Heavy Atom Count: 27
• Complexity: 692

Purity/Quality:

≥98% ^*data from raw suppliers

Mitraphyllin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2CN3CCC4(C3CC2C(=CO1)C(=O)OC)C5=CC=CC=C5NC4=O
• Isomeric SMILES: C[C@H]1[C@H]2CN3CC[C@]4([C@@H]3C[C@@H]2C(=CO1)C(=O)OC)C5=CC=CC=C5NC4=O
• Uses: Mitraphyllin is used in studies to evaluate isoniazid resistance and antibiotic activity potentiation in Mycobacterium using antibiotic combinations.

Technology Process of Mitraphylline

There total 17 articles about Mitraphylline 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:

ajmalicine (483-04-5) → mitraphylline (509-80-8)

Guidance literature:

Reference yield:

2-methoxy-19α-methyl-(7ξC2)-formosan-1-ene-16-carboxylic acid methyl ester (106654-59-5) → mitraphylline (509-80-8)

Guidance literature:

With acetic acid; Heating;

DOI:10.1021/ja00879a016

Reference yield:

7-chloro-19α-methyl-(7ξ)-7H-18-oxa-yohimb-16-ene-16-carboxylic acid methyl ester (94898-18-7) → mitraphylline (509-80-8)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. KOH / Heating

2: aq. AcOH / Heating

With potassium hydroxide; acetic acid;

DOI:10.1021/ja00879a016

upstream raw materials:

rauniticine-allo-oxindole A

2-methoxy-19α-methyl-(7ξC²)-formosan-1-ene-16-carboxylic acid methyl ester

ajmalicine

isomitraphylline

Downstream raw materials:

Mitraphyllic acid

ajmalicine

isomitraphylline

Refernces

• 1、 Pousset,Poisson,Shine,Shamma. "Stereochemistry of oxindole alkaloids". . p. 2766 - 2779. Retrieved 2007/10/04.