Sanguinarine

Base Information

• Chemical Name: Sanguinarine
• CAS No.: 2447-54-3
• Deprecated CAS: 18203-15-1,857014-91-6,1265889-92-6
• Molecular Formula: C20H14NO4
• Molecular Weight: 332.335
• European Community (EC) Number: 219-503-3
• UNII: AV9VK043SS
• DSSTox Substance ID: DTXSID0045204
• Nikkaji Number: J7.576K
• Wikipedia: Sanguinarine
• Wikidata: Q347392
• NCI Thesaurus Code: C81358
• Pharos Ligand ID: 6USDFPNJFGLF
• Metabolomics Workbench ID: 43793
• ChEMBL ID: CHEMBL417799
• Mol file: 2447-54-3.mol

Synonyms:pseudo-chelerythrine;pseudochelerythrine;sanguinarin;sanguinarine;sanguinarine chloride;sanguinarine hydroxide;sanguinarine nitrate;sanguinarine sulfate (1:1);sanguinarine sulfate (2:1);sanguiritrin;sangvinarin;Veadent;Viadent

Chemical Property of Sanguinarine

Chemical Property:

• Melting Point: 205-215 °C
• Refractive Index: 1.5180 (estimate)
• Boiling Point: 483.53°C (rough estimate)
• PSA: 40.80000
• Density: 1.3463 (rough estimate)
• LogP: 3.42810
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), DMSO (Slightly)
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 332.09228293
• Heavy Atom Count: 25
• Complexity: 530

Purity/Quality:

Macleaya cordata extract,60% Sanguinarine, ^*data from raw suppliers

Sanguinarium ^*data from reagent suppliers

Safty Information:

• Statements: 25
• Safety Statements: 13-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[N+]1=C2C(=C3C=CC4=C(C3=C1)OCO4)C=CC5=CC6=C(C=C52)OCO6
• Description: Sanguinarine, a DNA intercalator extracted from the bloodroot plant of the poppy family, was used by Native Americans for warts and as a blood purifier. In modern use, although banned by the FDA for its association with epidemic dropsy and other toxic effects, it has shown potential as a treatment for cancer, with modes of action including inhibition of metastasis and angiogenesis, and promotion of apoptosis. It also has anti-inflammatory, anti-oxidant, and anti-microbial properties, and several applications in veterinary medicine. A naphthoisoquinoline alkaloid, this base occurs in the roots of Chelidonium majus L., Glaucium fimbrilligerum and Sanguinaria canadensis L. The alkaloid was stated by Schmidt, Konig and Tietz to crystallize from EtOH or AcOEt as colourless needles, m.p. 213°C but this low melting point was found to be due to the presence of chelerythrine as an impurity. Once this is removed as the pseudocyanide, the base crystallizes from Et20 and has the above melting point or 242-3°C on slow heating. Obtained from EtOH it forms the alcoholate, m.p. 195-7°C. The hydrochloride forms long, slender, bloodred needles. On distillation with Zn dust, the alkaloid furnishes a-naphthaphenanthridine and the structure given above has been further confirmed by synthesis.
• Uses: Sanguinarium induces HO-1 expression thus inhibiting MMP-9 and COX-2 expression in TPA-induced breast cancer cells.

Technology Process of Sanguinarine

There total 6 articles about Sanguinarine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 58.0%

dihydrosanguinarine (3606-45-9) + ethyl bromoacetate (105-36-2) → Sanguinarine (2447-54-3)

Guidance literature:

With tris[2-phenylpyridinato-C₂,N]iridium(III); disodium hydrogenphosphate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In N,N-dimethyl-formamide; at 20 ℃; for 24h; Irradiation; Inert atmosphere;

DOI:10.1039/c6ra05927a

Reference yield: 24.0%

protopine N-oxide (87264-51-5) → Sanguinarine (2447-54-3) + dibenzooxazacycloundecine (87284-53-5)

Guidance literature:

In methanol; Irradiation;

Reference yield:

dihydrosanguinarine (3606-45-9) → Sanguinarine (2447-54-3)

Guidance literature:

With oxidase enzyme;

DOI:10.1016/S0040-4039(00)80829-1

upstream raw materials:

dihydrosanguinarine

protopine N-oxide

protopine

(S)-N-methylstylopine

Downstream raw materials:

dihydrosanguinarine

6-acetonyldihydrosanguinarine

oxysanguinarine

Refernces

• 1、 Sandor, Roman,Slanina, Jiri,Midlik, Adam,Sebrlova, Kristyna,Novotna, Lucie,Carnecka, Martina,Slaninova, Iva,Taborsky, Petr,Taborska, Eva,Pes, Ondrej. "Sanguinarine is reduced by NADH through a covalent adduct". . p. 77 - 84. Retrieved 2018.
• 2、 Beaudoin, Guillaume A.W.,Facchini, Peter J.. "Isolation and characterization of a cDNA encoding (S)-cis-N-methylstylopine 14-hydroxylase from opium poppy, a key enzyme in sanguinarine biosynthesis". . p. 597 - 603. Retrieved 2013/05/08.