436-77-1

Basic information

• Product Name: (+)-FANGCHINOLINE
• Synonyms: (+)-limacine;(1-beta)-2,2’-dimethyl-6,6’,12-trimethoxyberbaman-7-ol;2’-dimethyl-6,6’,12-trimethoxy-(1-beta)-berbaman-7-o;7-o-demethyltetrandrine;6,6',12-TRIMETHOXY-2,2'-DIMETHYLBERBAMAN-7-OL;(+)-FANGCHINOLINE;FANGCHINO-LINE;Fangchinoline, Demethyltetrandrine
• CAS NO: 436-77-1
• Molecular Formula: C₃₇H₄₀N₂O₆
• Molecular Weight: 608.72
• Product Categories: Alkaloids;reference substance
• Mol File: 436-77-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: 240～242℃
• Boiling Point: 709.7 °C at 760 mmHg
• Flash Point: 383 °C
• Appearance: /
• Density: 1.204 g/cm³
• Vapor Pressure: 8.25E-21mmHg at 25°C
• Refractive Index: 1.601
• PKA: 9.38±0.20(Predicted)
• CAS DataBase Reference: (+)-FANGCHINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-FANGCHINOLINE(436-77-1)
• EPA Substance Registry System: (+)-FANGCHINOLINE(436-77-1)

Safety Data

• Hazardous Substances Data: 436-77-1(Hazardous Substances Data)

Usage

Description

(+)-Fangchinoline is a bisbenzylisoquinoline alkaloid obtained from Limacia cuspidata and Stephania tetrandra. It is strongly laevorotatory and has been shown to possess diverse biological activities, including anti-inflammatory, neuroprotective, and anticancer properties. It is characterized by its long, colorless needles and has been found to inhibit the activity of sheep COX, decrease IL-6-induced proliferation of MH60 mouse hybridoma cells, reduce cyanide-induced increases in secreted glutamate levels and cell death in primary neonatal rat cerebellar granule neurons, and decrease proliferation of PC3 human prostate cancer cells.

Uses

Used in Anticancer Applications:
(+)-Fangchinoline is used as an anticancer agent for its ability to inhibit breast adenocarcinoma proliferation through apoptosis induction. It has also been shown to inhibit HIV-Type 1 replication.
Used in Neuroprotection:
(+)-Fangchinoline is used as a neuroprotective agent for its ability to reduce cyanide-induced increases in secreted glutamate levels and cell death in primary neonatal rat cerebellar granule neurons.
Used in Anti-inflammatory Applications:
(+)-Fangchinoline is used as an anti-inflammatory agent for its ability to inhibit the activity of sheep COX and decrease IL-6-induced proliferation of MH60 mouse hybridoma cells.
Used in Prostate Cancer Treatment:
(+)-Fangchinoline is used as a treatment for prostate cancer, as it has been shown to decrease the proliferation of PC3 human prostate cancer cells by 63 and 86% when used at concentrations of 20 and 30 μM, respectively.
Used in Tumor Growth Inhibition:
(+)-Fangchinoline is used to inhibit tumor growth in a PC3 mouse xenograft model when administered at a dose of 5 mg/kg per day for 12 days.

References

Tomita, Furukawa., Tetrahedron Lett., 4293 (1966)

InChI:InChI=1/C37H40N2O6/c1-38-14-12-24-19-31(42-4)33-21-27(24)28(38)16-22-6-9-26(10-7-22)44-32-18-23(8-11-30(32)41-3)17-29-35-25(13-15-39(29)2)20-34(43-5)36(40)37(35)45-33/h6-11,18-21,28-29,40H,12-17H2,1-5H3

Upstream product

• 477-57-6 (+)-isotetrandrine 
• 518-34-3 Tetrandrin 

Downstream Products

• 6681-13-6 Hernandezine 
• 118160-59-1 7-ethoxy fangchinoline 

Relevant articles and documents

Design, synthesis and in vitro anticancer research of novel tetrandrine and fangchinoline derivatives

Cancer treatment is one of the major public health issues in the world. Tetrandrine (Tet) and fangchinoline (d-Tet) are two bis-benzyl isoquinoline alkaloids extracted from Stephania tetrandra S. Moore, and their antitumor activities have been confirmed.

REGIOSELECTIVE O-DEMETHYLATION OF BISBENZYLISOQUINOLINE ALKALOIDS

The cleavage of methyl ethers of several bisbenzylisoquinoline alkaloids was studied and regioselective O-demethylation was observed.