A natural alkaloid with anti-inflammatory and anti-oxidant properties
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Active Metabolite(s)
31139Dihydrosanguinarine
Technical Support & Resources

Information provided in the product description is from published literature. Due to the nature of scientific experimentation, your results (e.g., selectivity and effective concentrations) or specific application for this product may differ. If you have questions about how this product fits your application, please contact our technical support staff.

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Sanguinarine (chloride)

Item No. 16951

Technical Information
Formal Name
13-methyl-[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium, monochloride
CAS Number
5578-73-4
Molecular Formula
C20H14NO4 • Cl
Formula Weight
Purity
≥98%
A crystalline solid
Methanol: 5 mg/ml
λmax
216, 235, 276, 328, 402, 472 nm
SMILES
C[N+]1=CC2=C(C=CC3=C2OCO3)C4=C1C5=CC(OCO6)=C6C=C5C=C4.[Cl-]
InChi Code
InChI=1S/C20H14NO4.ClH/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;1H/q+1;/p-1
InChi Key
GIZKAXHWLRYMLE-UHFFFAOYSA-M
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

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    Product Description

    Sanguinarine is a benzylisoquinoline alkaloid isolated from plants belonging to the family Papaveraceae.1 It exhibits antimicrobial, anti-inflammatory, and anti-oxidant properties and demonstrates antiproliferative and pro-apoptotic effects in some cancer cell lines. Sanguinarine suppresses NF-κB activation by blocking the degradation of IκBα and sensitizes cancer cells to apoptosis by inducing ROS generation and activating TNF-related apoptosis-inducing ligand.2 Furthermore, sanguinarine has been shown to reduce cancer cell metastasis though the inhibition of MMP-2 and MMP-9 activation and to exhibit antiangiogenic activity by downregulating VEGF-induced Akt activation.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ziegler, J., and Facchini, P.J. Alkaloid biosynthesis: Metabolism and trafficking. Annu. Rev. Plant Biol. 59, 735-769 (2008).

    2. Gupta, S.C., Kim, J.H., Prasad, S., et al. Regulation of survival, proliferation, invasion, angiogenesis, and metastasis of tumor cells through modulation of inflammatory pathways by nutraceuticals. Cancer Metastasis Rev. 29(3), 405-434 (2010).