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

Different sources of media describe the Description of 436-77-1 differently. You can refer to the following data:
1. A bisbenzylisoquino!ine alkaloid obtained from Limacia cuspidata (Miers.) Hook. f. et Thorn., the base crystallizes from Me2CO in the form of long, colourless needles. It is strongly laevorotatory with [α]D - 2120 (CHCI3) and has been shown to be the optical antipode of fanchinoline (q.v.).
2. Fangchinoline is an alkaloid that has been found in S. tetrandrae and has diverse biological activities, including anti-inflammatory, neuroprotective, and anticancer properties. It inhibits the activity of sheep COX and decreases IL-6-induced proliferation of MH60 mouse hybridoma cells with IC50 values of 129 and 3.7 μM, respectively. Fangchinoline (1 and 10 μM) reduces cyanide-induced increases in secreted glutamate levels and cell death in primary neonatal rat cerebellar granule neurons. It decreases proliferation of PC3 human prostate cancer cells by 63 and 86% when used at concentrations of 20 and 30 μM, respectively. Fangchinoline reduces tumor growth in a PC3 mouse xenograft model when administered at a dose of 5 mg/kg per day for 12 days.

Uses

(+)-Fangchinoline is an isolate from Stephania Tetrandra that shows anti-cancer activity. It inhibits breast adenocarcinoma proliferation through apoptosis induction. In addition, it has been shown to inhibit HIV-Type 1 replication.

Definition

ChEBI: A bisbenzylisoquinoline alkaloid that is (1beta)- berbaman which has been substituted by methyl groups at the 2 and 2' positions, by methoxy groups at the 6, 6', and 12 positions, and by a hydroxy group at position 7. Isolated from S ephania tetrandra, it has been found to possess neuroprotective and anti-tumour activity.

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

• 477-57-6 (+)-isotetrandrine 
• 6681-13-6 Hernandezine 

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.