548-30-1

Basic information

• Product Name: 13-Methyl[1,3]benzodioxolo[5,6-c][1,3]dioxolo[4,5-i]phenanthridine-14(13H)-one
• Synonyms: 13-Methyl[1,3]benzodioxolo[5,6-c][1,3]dioxolo[4,5-i]phenanthridine-14(13H)-one;13-Methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridin-14(13H)-one;Oxosanguinarine;Oxysanguinarine;Hydroxysanguinarine
• CAS NO: 548-30-1
• Molecular Formula: C₂₀H₁₃NO₅
• Molecular Weight: 347.3209
• Mol File: 548-30-1.mol
• Article Data: 17

Chemical Properties

• Melting Point: 223-224 °C
• Boiling Point: 628.7°Cat760mmHg
• Flash Point: 334.1°C
• Appearance: /
• Density: 1.509g/cm³
• Vapor Pressure: 1.01E-15mmHg at 25°C
• Refractive Index: 1.735
• PKA: -1.58±0.20(Predicted)
• CAS DataBase Reference: 13-Methyl[1,3]benzodioxolo[5,6-c][1,3]dioxolo[4,5-i]phenanthridine-14(13H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 13-Methyl[1,3]benzodioxolo[5,6-c][1,3]dioxolo[4,5-i]phenanthridine-14(13H)-one(548-30-1)
• EPA Substance Registry System: 13-Methyl[1,3]benzodioxolo[5,6-c][1,3]dioxolo[4,5-i]phenanthridine-14(13H)-one(548-30-1)

Safety Data

• Hazardous Substances Data: 548-30-1(Hazardous Substances Data)

Usage

Description

An a-naphthaphenanthridine alkaloid, this base occurs in the roots of Sanguinaria canadensis. It is separated from the remaining bases by chromatography and purified by crystallization from CHC13 followed by sublimation in a high vacuum. It is optically inactive and may also be prepared by oxidation of sanguinarine nitrate by potassium ferricyanide in alkaline solution. No salts of this alkaloid have been prepared.

Uses

Hydroxysanguinarine can be used to treat coronavirus infection.

References

Spiithetal., Ber., 70, 1677 (1936) Schlemmer, Gempp., Arch. Pharm., 276,506 (1938)

InChI:InChI=1/C20H13NO5/c1-21-18-12(3-2-10-6-15-16(7-13(10)18)25-8-24-15)11-4-5-14-19(26-9-23-14)17(11)20(21)22/h2-7H,8-9H2,1H3

Upstream product

• 5578-73-4 sanguinarine chloride 
• 4070-41-1 8-hydroxydihydosanguinarine 
• 1207666-53-2 C₉H₈BrNO₂ 
• 72744-54-8 5-bromo-benzo[1,3]dioxole-4-carbaldehyde 
• 6412-87-9 5,6-methylenedioxy-1-indanone 
• 1620903-00-5 6-bromo-2,3-methylenedioxy-N-methyl-N-(6,7-methylenedioxynaphthalen-1-yl)benzamide 
• 1620902-99-9 6-bromo-2,3-methylenedioxy-N-(6,7-methylenedioxynaphthalen-1-yl)benzamide 
• 53811-49-7 naphtho[2,3-d][1,3]dioxol-5-amine 
• 1620902-98-8 6,7-methylenedioxy-1-(2,2,2-trichloromethylcarbonylamino)naphthalene 
• 1620902-92-2 6,7-methylenedioxy-1-(2,2,2-trichloromethylcarbonylamino)-1,4-dihydronaphthalene 
• 1620902-84-2 (2E)-3-(2-allyl-4,5-methylenedioxyphenyl)prop-2-en-1-ol 
• 1620902-77-3 ethyl (2E)-3-(2-allyl-4,5-methylenedioxyphenyl)prop-2-enoate 
• 86838-09-7 ethyl (2E)-3-(2-bromo-4,5-methylenedioxyphenyl)prop-2-enoate 
• 957765-79-6 6-bromo-2,3-(methylenedioxy)benzoyl chloride 

Downstream Products

• 5578-73-4 sanguinarine chloride 

Relevant articles and documents

Photooxidation of alkaloids: Considerable quantum yield enhancement by rose bengal-sensitized singlet molecular oxygen generation

The photooxidation of sanguinarine, coralyne and berberine was studied in oxygenated alkaline methanol solutions. Rose bengal as photosensitizer significantly accelerates the process, indicating the importance of singlet molecular oxygen in the reaction mechanism. The quantum yield of sensitized oxidation was found to increase significantly with pH and reaches 0.4 for berberine at pH 13.8. The direct oxidation of alkaloids is less efficient, the quantum yield does not exceed 0.01 even in oxygen-saturated solutions. The photoinduced electron ejection does not play a role in the oxidation. The uncharged pseudobase forms, which are present in alkaline medium, are oxidized much more easily than the alkaloid cations. The quantum yield of rose bengal-sensitized photooxidation of berberine and coralyne alkaloids increases significantly with pH. Singlet molecular oxygen plays an important role in the reaction mechanism.

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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.

Preparation of amino-substituted indenes and 1,4-dihydronaphthalenes using a one-pot multireaction approach: Total synthesis of oxybenzo[c]phenanthridine alkaloids

Allylic trichloroacetimidates bearing a 2-vinyl or 2-allylaryl group have been designed as substrates for a one-pot, two-step multi-bond-forming process leading to the general preparation of aminoindenes and amino-substituted 1,4-dihydronaphthalenes. The synthetic utility of the privileged structures formed from this one-pot process was demonstrated with the total synthesis of four oxybenzo[c]phenanthridine alkaloids, oxychelerythrine, oxysanguinarine, oxynitidine, and oxyavicine. An intramolecular biaryl Heck coupling reaction, catalyzed using the Hermann-Beller palladacycle was used to effect the key step during the synthesis of the natural products.