6880-91-7

Basic information

• Product Name: Dihydrochelerythrine
• Synonyms: Dihydrochelerythrine;12,13-Dihydro-1,2-dimethoxy-12-methyl-[1,3]benzodioxolo[5,6-c]phenanthridine;12,13-Dihydro-1,2-dimethoxy-12-methyl[1,3]benzodioxolo[5,6-c]phenanthridine;12,13-Dihydrochelerythrine
• CAS NO: 6880-91-7
• Molecular Formula: C₂₁H₁₉NO₄
• Molecular Weight: 349.37986
• EINECS: 200-258-5
• Mol File: 6880-91-7.mol
• Article Data: 3

Chemical Properties

• Melting Point: 164-165 °C
• Boiling Point: 565.9°Cat760mmHg
• Flash Point: 171.6°C
• Appearance: /
• Density: 1.291g/cm³
• Vapor Pressure: 7.92E-13mmHg at 25°C
• Refractive Index: 1.656
• Storage Temp.: 2-8°C
• PKA: 2.36±0.20(Predicted)
• CAS DataBase Reference: Dihydrochelerythrine(CAS DataBase Reference)
• NIST Chemistry Reference: Dihydrochelerythrine(6880-91-7)
• EPA Substance Registry System: Dihydrochelerythrine(6880-91-7)

Safety Data

• Hazardous Substances Data: 6880-91-7(Hazardous Substances Data)

Usage

Description

Dihydrochelerythrine is a benzophenanthridine alkaloid found in Bocconia arborea, exhibiting a range of biological activities. It demonstrates potent antimicrobial properties against S. aureus, S. faecalis, and C. albicans, with a minimum inhibitory concentration (MIC) of 1.87 μg/ml for all. Additionally, it effectively inhibits the secretion of hepatitis B virus (HBV) antigens HBsAg and HBeAg from HepG2 2.2.15 cells, with IC50 values of less than 0.05 μM for both. Dihydrochelerythrine also exhibits cytotoxicity against various cancer cell lines, including HCT8, BGC-823, and A2780, with IC50 values of 1.4, 0.4, and 3.5 μM, respectively.

Uses

Used in Antimicrobial Applications:
Dihydrochelerythrine is used as an antimicrobial agent for its effectiveness against S. aureus, S. faecalis, and C. albicans, with a minimum inhibitory concentration (MIC) of 1.87 μg/ml for all.
Used in Antiviral Applications:
Dihydrochelerythrine is used as an antiviral agent, specifically inhibiting the secretion of hepatitis B virus (HBV) antigens HBsAg and HBeAg from HepG2 2.2.15 cells, with IC50 values of less than 0.05 μM for both.
Used in Anticancer Applications:
Dihydrochelerythrine is used as an anticancer agent, exhibiting cytotoxicity against various cancer cell lines such as HCT8, BGC-823, and A2780, with IC50 values of 1.4, 0.4, and 3.5 μM, respectively.
Used in Pharmaceutical Research:
Dihydrochelerythrine is synthesized as a potential G-quadruplex DNA stabilizing agent, which can be utilized in the development of new drugs targeting specific genetic sequences.
Used in Pharmacokinetic Studies:
Dihydrochelerythrine is used in pharmacokinetic studies of chelerythrine metabolites in agro-products, aiding in understanding the absorption, distribution, metabolism, and excretion of these compounds in the body.

InChI:InChI=1/C21H19NO4/c1-22-10-16-13(6-7-17(23-2)21(16)24-3)14-5-4-12-8-18-19(26-11-25-18)9-15(12)20(14)22/h4-9H,10-11H2,1-3H3

Upstream product

• 16211-68-0 (+/-)-cis-N-methyl-7,8,13,13a-tetrahydroberberinium chloride 
• 522-97-4 canadine 
• 4070-42-2 6-hydroxy-5,6-dihydrochelerythrine 

Downstream Products

• 15575-49-2 6-acetonyldihydrochelerythrine 
• 34316-15-9 chelerythrinium 
• 3895-92-9 chelerythrine chloride 
• 28342-33-8 oxychelerythrine 

Relevant articles and documents

Chemical Transformation of Protoberberines. Part 9. A Biomimetic Synthesis of Oxychelerythrine, Dihydrochelerythrine, and Chelerythrine from Berberine

Fully aromatised benzophenanthridine alkaloids, oxychelerythrine (4), dihydrochelerythrine (9), and chelerythrine (10) have been efficiently synthesized from berberine (1), a protoberberine alkaloid, via oxidative C(6)-N bond cleavage, followed by recyclisation betwen the C-6 and C-13 positions of (1) by a biogenetic process.

Biosynthesis of benzo[c]phenanthridine alkaloids sanguinarine, chelirubine and macarpine

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