Dihydrochelerythrine

Base Information

• Chemical Name: Dihydrochelerythrine
• CAS No.: 6880-91-7
• Molecular Formula: C21H19NO4
• Molecular Weight: 349.386
• Hs Code.: 2933990090
• European Community (EC) Number: 807-650-1
• DSSTox Substance ID: DTXSID70218913
• Nikkaji Number: J391.781I
• Wikidata: Q72464723
• Metabolomics Workbench ID: 133588
• ChEMBL ID: CHEMBL400359
• Mol file: 6880-91-7.mol

Synonyms:dihydrochelerythrine

Chemical Property of Dihydrochelerythrine

Chemical Property:

• Vapor Pressure: 7.92E-13mmHg at 25°C
• Melting Point: 164-165 °C
• Boiling Point: 565.9°Cat760mmHg
• PKA: 2.36±0.20(Predicted)
• Flash Point: 171.6°C
• PSA: 40.16000
• Density: 1.291g/cm³
• LogP: 4.26750
• Storage Temp.: 2-8°C
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 349.13140809
• Heavy Atom Count: 26
• Complexity: 516

Purity/Quality:

≥98% ^*data from raw suppliers

Dihydrochelerythrine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CC2=C(C=CC(=C2OC)OC)C3=C1C4=CC5=C(C=C4C=C3)OCO5
• Description: Dihydrochelerythrine is a benzophenanthridine alkaloid that has been found in Bocconia arborea and has diverse biological activities. It is active against S. aureus, S. faecalis, and C. albicans (MIC = 1.87 μg/ml for all). Dihydrochelerythrine inhibits secretion of the hepatitis B virus (HBV) antigens HBsAg and HBeAg from HepG2 2.2.15 cells (IC50s = <0.05 μM for both). It is cytotoxic to HCT8, BGC-823, and A2780 cancer cells (IC50s = 1.4, 0.4, and 3.5 μM, respectively).
• Uses: Dihydrochelerythrine is synthesized as a potential G-quadrulpex DNA stabilizing agent. It is used in phamacokinetic study of chelerythrine metabolites in agro-products.

Technology Process of Dihydrochelerythrine

There total 3 articles about Dihydrochelerythrine 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: 96.0%

6-hydroxy-5,6-dihydrochelerythrine (4070-42-2) → 12,13-dihydrochelerythrine (6880-91-7)

Guidance literature:

With sodium tetrahydroborate; In methanol; for 0.5h; Ambient temperature;

Reference yield: 1.4%

(+/-)-cis-N-methyl-7,8,13,13a-tetrahydroberberinium chloride (16211-68-0,24031-76-3,37791-14-3,57089-29-9,59895-76-0,85888-53-5,85888-54-6) → 12,13-dihydrochelerythrine (6880-91-7) + allocryptopine (485-91-6,24240-04-8)

Guidance literature:

In water; at 24 ℃; for 192h; incorporation experiment on Macleaya cordata in Murashige and Skoog's medium;

DOI:10.1002/hlca.19830660208

Reference yield: 0.4%

canadine (522-97-4,2086-96-6,5096-57-1,29074-38-2) → 12,13-dihydrochelerythrine (6880-91-7) + berberine iodide (4263-84-7) + allocryptopine (485-91-6,24240-04-8)

Guidance literature:

In water; at 24 ℃; for 144h; incorporation experiment on Macleaya cordata in Murashige and Skoog's medium;

DOI:10.1002/hlca.19830660208

upstream raw materials:

6-hydroxy-5,6-dihydrochelerythrine

canadine

(+/-)-cis-N-methyl-7,8,13,13a-tetrahydroberberinium chloride

Downstream raw materials:

chelerythrinium

6-acetonyldihydrochelerythrine

chelerythrine chloride

oxychelerythrine

Refernces

• 1、 Hanaoka, Miyoji,Motonishi, Toshio,Mukai, Chisato. "A Biomimetic Conversion of Berberine into Chelerythrine and Dihydrochelerythrine". . p. 718 - 719. Retrieved 2007/10/02.