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436-77-1

(+)-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.

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  • 16H-1,24:6,9-Dietheno-11,15-metheno-2H-pyrido[2',3':17,18][1,11]dioxacycloeicosino[2,3,4-ij]isoquinolin-22-ol,3,4,4a,5,16a,17,18,19-octahydro-12,21,26-trimethoxy-4,17-dimethyl-, (4aS,16aS)-

    Cas No: 436-77-1

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  • 436-77-1 Structure

  • Basic information

    1. Product Name: (+)-FANGCHINOLINE
    2. 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
    3. CAS NO:436-77-1
    4. Molecular Formula: C37H40N2O6
    5. Molecular Weight: 608.72
    6. EINECS: N/A
    7. Product Categories: Alkaloids;reference substance
    8. Mol File: 436-77-1.mol

  • Chemical Properties

    1. Melting Point: 240～242℃
    2. Boiling Point: 709.7 °C at 760 mmHg
    3. Flash Point: 383 °C
    4. Appearance: /
    5. Density: 1.204 g/cm3
    6. Vapor Pressure: 8.25E-21mmHg at 25°C
    7. Refractive Index: 1.601
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. PKA: 9.38±0.20(Predicted)
    11. CAS DataBase Reference: (+)-FANGCHINOLINE(CAS DataBase Reference)
    12. NIST Chemistry Reference: (+)-FANGCHINOLINE(436-77-1)
    13. EPA Substance Registry System: (+)-FANGCHINOLINE(436-77-1)

  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 436-77-1(Hazardous Substances Data)

436-77-1 Usage

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)

Check Digit Verification of cas no

The CAS Registry Mumber 436-77-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,3 and 6 respectively; the second part has 2 digits, 7 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 436-77:
(5*4)+(4*3)+(3*6)+(2*7)+(1*7)=71
71 % 10 = 1
So 436-77-1 is a valid CAS Registry Number.
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

436-77-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name Fangchinoline

1.2 Other means of identification

Product number -
Other names d,l-Fangchinolin

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:436-77-1 SDS

436-77-1Downstream Products

436-77-1Relevant articles and documents

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

Gao, Xiu-zheng,Lv, Xu-tao,Zhang, Rui-rui,Luo, Yang,Wang, Mu-xuan,Chen, Jia-shu,Zhang, Yu-kai,Sun, Bin,Sun, Jin-yue,Liu, Yu-fa,Liu, Chao

, (2021/02/22)

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.

Bioactive bisbenzylisoquinoline alkaloids from the roots of Stephania tetrandra

Li, Jiayuan,Li, Li,Li, Xuyu,Liu, Yanfei,Shi, Guoru,Wang, Renzhong,Yu, Dequan,Yuan, Jiqiao,Zhou, Jie

, (2020/03/17)

Ten new bisbenzylisoquinoline alkaloids (1–10) and eight known analogues (11–18) were obtained from the roots of Stephania tetrandra. The structures of these compounds were determined by spectroscopic methods, single-crystal X-ray diffraction, electronic

REGIOSELECTIVE O-DEMETHYLATION OF BISBENZYLISOQUINOLINE ALKALOIDS

Kunitomo, Jun-ichi,Oshikata, Megumi,Akasu, Michinori,Ishii, Hisashi

, p. 937 - 942 (2007/10/02)

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

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