2447-54-3

Basic information

• Product Name: SANGUINARINE
• Synonyms: PSEUDOCHELERYTHRINE;SANGUINARIN;SANGUINARINE;3)-benzodioxolo(5,6-c)-1,3-dioxolo(4,5-i)phenanthridinium,13-methyl-(;dimethylenedioxybenzphenanthridine;SANGUINARINE CHLORIDE ISOLATED FROM MACL EAY;SANGUINARINE, 98+% BY HPLC;SANGUINARINE, 40+% BY UV
• CAS NO: 2447-54-3
• Molecular Formula: C₂₀H₁₄NO₄
• Molecular Weight: 332.33
• EINECS: 219-503-3
• Product Categories: Alkaloids;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;natural product;Inhibitors
• Mol File: 2447-54-3.mol
• Article Data: 6

Chemical Properties

• Melting Point: 205-215°C
• Boiling Point: 483.53°C (rough estimate)
• Appearance: /
• Density: 1.3463 (rough estimate)
• Refractive Index: 1.5180 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), DMSO (Slightly)
• CAS DataBase Reference: SANGUINARINE(CAS DataBase Reference)
• NIST Chemistry Reference: SANGUINARINE(2447-54-3)
• EPA Substance Registry System: SANGUINARINE(2447-54-3)

Safety Data

• Statements: 25
• Safety Statements: 13-45
• RIDADR: 1544
• Hazardous Substances Data: 2447-54-3(Hazardous Substances Data)

Usage

Description

Sanguinarine, a benzophenanthridine alkaloid, is derived from the bloodroot plant of the poppy family, known as Sanguinaria canadensis L. It has been traditionally used by Native Americans for treating warts and as a blood purifier. Despite being banned by the FDA due to its association with toxic effects, sanguinarine has demonstrated potential in various applications, including cancer treatment, anti-inflammatory, anti-oxidant, and anti-microbial properties.

Uses

Used in Cancer Treatment:
Sanguinarine is used as an anticancer agent for its potential in inhibiting metastasis and angiogenesis, and promoting apoptosis. It has shown effectiveness in inducing HO-1 expression, thus inhibiting MMP-9 and COX-2 expression in TPA-induced breast cancer cells.
Used in Skin Protection:
Sanguinarine is used as a protective agent for preventing and treating UV-induced skin damage. Topical application of sanguinarine on the skin of SKH-1 hairless mice before or after UVB irradiation has resulted in significantly lower UVB-mediated skin edema, skin hyperplasia, infiltration of leukocytes, and markers of oxidative stress (e.g., H2O2).
Used in Veterinary Medicine:
Sanguinarine is used in various applications within the veterinary medicine industry, taking advantage of its anti-inflammatory, anti-oxidant, and anti-microbial properties to treat and prevent various conditions in animals.
Used in Drug Delivery Systems:
Although not explicitly mentioned in the provided materials, sanguinarine's potential applications in drug delivery systems could be explored due to its various biological activities and properties. This may involve the development of novel drug delivery systems to enhance its efficacy and bioavailability in targeted treatments.

Sources

https://en.wikipedia.org/wiki/Sanguinarine https://pubchem.ncbi.nlm.nih.gov/compound/sanguinarine#section=Human-Metabolite-Information https://www.essense-of-life.com/healthtopics/A-513/Sanguinarine-Health-Topic.html https://www.caymanchem.com/product/16951 https://www.sciencedirect.com/topics/nursing-and-health-professions/sanguinarine

References

Dana., Mag. Pharm., 23, 125 (1829) Bruchhausen, Bersch., Ber., 63, 2520 (1930) Spath, Kuffner., ibid, 64, 370, 1123, 2034 (1931) Synthesis: Dyke, Moon, Sainsbury., Tetrahedron Lett., 3933 (1968)

InChI:InChI=1/C20H14NO4/c1-21-8-15-12(4-5-16-20(15)25-10-22-16)13-3-2-11-6-17-18(24-9-23-17)7-14(11)19(13)21/h2-8H,9-10H2,1H3/q+1

Upstream product

• 3606-45-9 dihydrosanguinarine 
• 87264-51-5 protopine N-oxide 
• 130-86-9 protopine 
• 203926-50-5 (S)-N-methylstylopine 
• 105-36-2 ethyl bromoacetate 

Downstream Products

• 3606-45-9 dihydrosanguinarine 
• 72401-54-8 8-methoxydihydrosanguinarine 
• 28342-31-6 6-Ethoxy-5,6-dihydrosanguinarine 
• 548-30-1 oxysanguinarine 
• 37687-34-6 6-acetonyldihydrosanguinarine 

Relevant articles and documents

One step enzymatic synthesis of dihydrosanguinarine from protopine

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A novel C-C radical-radical coupling reaction promoted by visible light: Facile synthesis of 6-substituted: N -methyl 5,6-dihydrobenzophenanthridine alkaloids

A novel photoredox-mediated direct intermolecular C-H functionalization of N-methyl 5,6-dihydrobenzophenanthridine is developed utilizing the visible light-induced reductive quenching pathway of photocatalyst Ir(ppy)3. In the proposed coupling mechanism, an α-amino C-radical is generated at the 6-position of N-methyl 5,6-dihydrobenzophenanthridine which is capable of coupling with α-EWG (electron withdrawing group) substituted C-radicals. The utility of this methodology has been demonstrated via rapid access to the analogue of natural 6-substituted N-methyl 5,6-dihydrobenzophenanthridine alkaloids.

Characterization of a flavoprotein oxidase from opium poppy catalyzing the final steps in sanguinarine and papaverine biosynthesis

Benzylisoquinoline alkaloids are a diverse class of plant specialized metabolites that includes the analgesic morphine, the antimicrobials sanguinarine and berberine, and the vasodilator papaverine. The two-electron oxidation of dihydrosanguinarine catalyzed by dihydrobenzophenanthridine oxidase (DBOX) is the final step in sanguinarine biosynthesis. The formation of the fully conjugated ring system in sanguinarine is similar to the four-electron oxidations of (S)-canadine to berberine and (S)-tetrahydropapaverine to papaverine. We report the isolation and functional characterization of an opium poppy (Papaver somniferum) cDNA encoding DBOX, a flavoprotein oxidase with homology to ( S)-tetrahydroprotoberberine oxidase and the berberine bridge enzyme. A query of translated opium poppy stem transcriptome databases using berberine bridge enzyme yielded several candidate genes, including an (S)-tetrahydroprotoberberine oxidase-like sequence selected for heterologous expression in Pichia pastoris. The recombinant enzyme preferentially catalyzed the oxidation of dihydrosanguinarine to sanguinarine but also converted (RS)-tetrahydropapaverine to papaverine and several protoberberine alkaloids to oxidized forms, including (RS)-canadine to berberine. The Km values of 201 and 146 μM for dihydrosanguinarine and the protoberberine alkaloid (S)-scoulerine, respectively, suggested high concentrations of these substrates in the plant. Virus-induced gene silencing to reduce DBOX transcript levels resulted in a corresponding reduction in sanguinarine, dihydrosanguinarine, and papaverine accumulation in opium poppy roots in support of DBOX as a multifunctional oxidative enzyme in BIA metabolism.