SANGUINARINE Chemical Properties

Melting point:

205-215°C

Boiling point:

483.53°C (rough estimate)

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)

form 

Solid

color 

White

LogP

-0.653 (est)

Safety Information

Risk Statements 

25

Safety Statements 

13-45

RIDADR 

1544

Toxicity

LD50 oral in rat: 1660mg/kg

SANGUINARINE Usage And Synthesis

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.

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

Description

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.

Definition

Sanguinarine is a benzophenanthridine alkaloid derived from the root of Sanguinaria canadendid. Limited available evidence indicates that it may be used to prevent and treat UV-induced skin damage. Specifically, topical application of sanguinarine on the skin of SKH-1 hairless mice before or after UVB irradiation resulted in significantly lower UVB-mediated skin edema, skin hyperplasia and infiltration of leukocytes, and markers of oxidative stress (e.g., H2O2).

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)

SANGUINARINE(2447-54-3)Related Product Information

• JATRORRHIZINE HCL(RG)
• Coptisine chloride
• CUCURBITACIN IIA
• Berberine
• Ferulic Acid
• Celastrus angulatus
• Spatholobi Caulis
• Capillary Wormwood Herb Extract
• Sanguinarine citrate
• chelerythrine chloride-sanguinarine chloride mixt.
• SANGUINARINE HCl hplc,SANGUINARINE(SH),SANGUINARINE CHLORIDE,SANGUINARINE HCL
• SANGUINARINE CHLORIDE(RG)
• Ethoxysanguinarine
• DIHYDROSANGUINARINE(P)
• SANGUINARINE NITRATE,SANGUINARINE NITRATE(RG)
• SANGUINARINE CHLORIDE HYDRATE
• SANGUINARINE SULFATE
• SANGUINARINE HCL DIHYDRATE