Sanguinarine

Catalog Number	ACM2447543-2
CAS Number	2447-54-3
Structure
Description	Sanguinarine is a natural compound that has shown pro-apoptotic properties in vitro. It also induces apoptosis in human osteosarcoma cells by binding to the pro-apoptotic protein, Bax, and releasing cytochrome c from mitochondria. Sanguinarine also inhibits dextran sulfate induced erythrocyte hemolysis by blocking the synthesis of DNA and protein. The chemical structure of sanguinarine is similar to that of pyrrolizidine alkaloids, which are known carcinogens and mutagens. These compounds have shown cytotoxic effects on human lymphocytes, monocytes, and erythrocytes at concentrations of 10 μg/ml or higher. Sanguinarine has been shown to inhibit the growth of Staphylococcus aureus cells in a dose-dependent manner when used at concentrations between 0.01 mM and 1 mM.
Synonyms	Dimethylenedioxybenzphenanthridine
IUPAC Name	24-Methyl-5,7,18,20-tetraoxa-24-azoniahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-1(24),2,4(8),9,11,13,15,17(21),22-nonaene
Molecular Weight	332.33 g/mol
Molecular Formula	C20H14NO4
Canonical SMILES	C[N+]1=C2C(=C3C=CC4=C(C3=C1)OCO4)C=CC5=CC6=C(C=C52)OCO6
InChI	InChI=1S/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
InChI Key	INVGWHRKADIJHF-UHFFFAOYSA-N
Boiling Point	483.53 °C
Melting Point	205-215 °C
Purity	98%
Density	1.35 g/ml
Appearance	Red powder
Storage	store at 2℃-8℃, protect from light
Complexity	530
Covalently-Bonded Unit Count	1
Defined Atom Stereocenter Count	0
Exact Mass	332.09228293
Harmonized Tariff Code	Switzerland: 29420090 - USA: 2942005000 - Slovakia: 2942000090 - UK: 2942000000 - China: 2942000000
Heavy Atom Count	25
Hydrogen Bond Acceptor Count	4
Hydrogen Bond Donor Count	0
MDL Number	MFCD00064925
Monoisotopic Mass	332.09228293
PhysicalState	Powder
Rotatable Bond Count	0
Topological Polar Surface Area	40.8 Ų

Custom Q&A

What is the chemical formula for Sanguinarine?

The chemical formula for Sanguinarine is C20H14NO4+.

What is the molecular weight of Sanguinarine?

The molecular weight of Sanguinarine is 332.33.

At what temperature does Sanguinarine melt?

Sanguinarine melts at a temperature range of 205-215°C.

What are some of the chemical properties of Sanguinarine?

Some chemical properties of Sanguinarine include its white color, solubility in chloroform and DMSO, and a melting point range of 205-215°C.

What are the safety precautions associated with Sanguinarine?

Sanguinarine is associated with risk statements 25 and safety statements 13-45. The LD50 oral toxicity in rats is 1660mg/kg.

How is Sanguinarine used traditionally by Native Americans?

Sanguinarine was used by Native Americans for warts and as a blood purifier.

What potential therapeutic uses have been explored for Sanguinarine?

Sanguinarine has shown potential as a treatment for cancer, with modes of action including inhibition of metastasis and angiogenesis, promotion of apoptosis, anti-inflammatory, anti-oxidant, and anti-microbial properties, as well as applications in veterinary medicine.

Where is Sanguinarine derived from in nature?

Sanguinarine is a naphthoisoquinoline alkaloid that occurs in the roots of plants such as Chelidonium majus L., Glaucium fimbrilligerum, and Sanguinaria canadensis L.

What is the chemical structure of Sanguinarine?

Sanguinarine is a benzophenanthridine alkaloid with a specific chemical structure derived from the root of Sanguinaria canadendid.

How does Sanguinarine potentially prevent and treat UV-induced skin damage?

Limited evidence suggests that Sanguinarine may be used to prevent and treat UV-induced skin damage by inhibiting MMP-9 and COX-2 expression in TPA-induced breast cancer cells, leading to lower skin edema, hyperplasia, leukocyte infiltration, and oxidative stress markers after UVB irradiation.

※ Please kindly note that our products are for research use only.