522-30-5

Basic information

• Product Name: Norsanguinarine
• Synonyms: [1,3]Benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridine;13-Demethylsanguinarine;Norsanguinarine
• CAS NO: 522-30-5
• Molecular Formula: C₁₉H₁₁NO₄
• Molecular Weight: 317.29494
• Mol File: 522-30-5.mol
• Article Data: 9

Chemical Properties

• Melting Point: 279-280 °C
• Boiling Point: 574.6°Cat760mmHg
• Flash Point: 200.4°C
• Appearance: /
• Density: 1.53g/cm³
• Vapor Pressure: 1.3E-12mmHg at 25°C
• Refractive Index: 1.819
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), DMSO (Slightly, Heated), Methanol (Slightly, Heated)
• PKA: 3.84±0.20(Predicted)
• CAS DataBase Reference: Norsanguinarine(CAS DataBase Reference)
• NIST Chemistry Reference: Norsanguinarine(522-30-5)
• EPA Substance Registry System: Norsanguinarine(522-30-5)

Safety Data

• Hazardous Substances Data: 522-30-5(Hazardous Substances Data)

Usage

Description

Furuya, Ikuta, Syono., Phytochem., 11,3041 (1972)

Uses

Norsanguinarine is an intermediate in the synthesis of Sanguinarium-13CD3 Chloride (S112502). Sanguinarium-13CD3 Chloride is the labeled analogue of Sanguinarium Chloride (S112500). Sanguinarium Chloride is a natural product with antimicrobial, anti-inflammatory, and anti-oxidant properties.

References

Furuya, Ikuta, Syono., Phytochem., 11,3041 (1972)

InChI:InChI=1/C19H11NO4/c1-2-12-11-3-4-15-19(24-9-21-15)14(11)7-20-18(12)13-6-17-16(5-10(1)13)22-8-23-17/h1-7H,8-9H2

Upstream product

• 5578-73-4 sanguinarine chloride 
• 100-51-6 benzyl alcohol 
• 93666-99-0 N-(6'-bromo-2',3'-methylenedioxybenzyl)-6,7-methylenedioxy-1-naphthylamine 
• 76786-86-2 (+)-chelidonine N-oxide 
• 3606-45-9 dihydrosanguinarine 
• 476-32-4 chelidonine 
• 53811-49-7 naphtho[2,3-d][1,3]dioxol-5-amine 
• 53811-53-3 7,8-Dihydro-6H-naphtho[2,3-d][1,3]dioxol-5-one oxime 
• 93666-98-9 N-(6'-bromo-2',3'-methylenedioxybenzal)-6,7-methylenedioxy-1-naphthylamine 
• 72744-54-8 5-bromo-benzo[1,3]dioxole-4-carbaldehyde 
• 1114515-47-7 3,4-dihydro-6,7-methylenedioxy-2-trifluoromethanesulfonyloxynaphthalene 
• 1114515-36-4 2-(6,7-methylenedioxy-3,4-diydronaphthyl)boronic acid pinacol ester 
• 1114515-40-0 1-allyl-3,4-methylenedioxy-6-trifluoromethanesulfonyloxybenzene 
• 1114515-42-2 1,2-diallyl-4,5-methylenedioxybenzene 

Downstream Products

• 5578-73-4 sanguinarine chloride 
• 3606-45-9 dihydrosanguinarine 

Relevant articles and documents

The synthesis of sanguinarine.

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The synthesis and biological evaluation of sanguinarine derivatives as anti-non-small cell lung cancer agents

A novel series of sanguinarine (SA) derivatives were synthesized and evaluated as anti-non-small cell lung cancer (NSCLC) agents. The compounds inhibited A549 and H1975 NSCLC cells with IC50 values of 0.96->30 ΜM and 0.79->30 ΜM, respectively. Compounds 8d-8j exhibited low micromolar inhibitory activity and indicated that the C6-position of SA was tolerated to be substituted by hydrophilic groups and CN. Further investigation of their mechanism of action showed that compound 8h induced apoptosis of A549 and H1975 cells by inhibiting the Akt signaling pathway and elevating the reactive oxygen species (ROS). This study provided a strategy for developing new anti-cancer agents.

SANGUINARINE ANALOG PP2C INHIBITORS FOR CANCER TREATMENT

Sanguinarine analogs as PP2C inhibitors are disclosed for the treatment of various cancers, as well as methods of synthesizing such analogs.