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S5890

Sigma-Aldrich

Sanguinarine chloride hydrate

≥98% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C20H14ClNO4 · xH2O
CAS Number:
Molecular Weight:
367.78 (anhydrous basis)
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98% (HPLC)

solubility

H2O: slightly soluble <0.3 mg/mL
methanol: 3.8 mg/mL

SMILES string

[Cl-].C[n+]1cc2c3OCOc3ccc2c4ccc5cc6OCOc6cc5c14

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

Application

Sanguinarine chloride hydrate was tested for anti-schistosomal activities against Schistosoma mansoni.9 It was tested for anti-lipase activity against Candida rugosa lipase.10
Sanguinarine chloride hydrate yields clear, orange solution in methanol at 20 mg/ml.

Biochem/physiol Actions

A natural product with antimicrobial, anti-inflammatory, and anti-oxidant properties. Has antiproliferative, pro-apoptosis effects in some cancer cell lines.
Sanguinarine is a benzophenanthridine alkaloid isolated from plants belonging to the family Papaveracea. It exhibits anti-bacterial, anti-fungal, anti-inflammatory and anti-cancer properties. It induces cell cycle arrest and sensitizes cancer cells to apoptosis by activating TNF-related apoptosis inducing ligand.6,7 It inhibits STAT3, MMP-2, MMP-9, interacts with glutathione, induces generation of ROS, disrupts the microtubule assembly and causes DNA damage resulting the death of the cancer cells.6,7,8

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves


Certificates of Analysis (COA)

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Jin-Jian Lu et al.
Evidence-based complementary and alternative medicine : eCAM, 2012, 485042-485042 (2012-09-19)
Alkaloids are important chemical compounds that serve as a rich reservoir for drug discovery. Several alkaloids isolated from natural herbs exhibit antiproliferation and antimetastasis effects on various types of cancers both in vitro and in vivo. Alkaloids, such as camptothecin
Siraj Pallichankandy et al.
Free radical biology & medicine, 89, 708-720 (2015-10-17)
Malignant gliomas are notoriously resistant to therapies that induce apoptosis, but are less resistant to therapies that induce autophagy. Therefore, drugs targeting autophagy are promising candidates in the treatment of malignant gliomas. In this study, we investigated the anti-glioma potential
Matthew Mendoza Barker et al.
Journal of fungi (Basel, Switzerland), 10(2) (2024-02-23)
Coccidioidomycosis (CM) can manifest as respiratory and disseminated diseases that are caused by dimorphic fungal pathogens, such as Coccidioides species. The inhaled arthroconidia generated during the saprobic growth phase convert into multinucleated spherules in the lungs to complete the parasitic
Hieu Huu Le et al.
Antioxidants (Basel, Switzerland), 9(10) (2020-10-25)
Heat stress (HS) compromises productivity of pork production, in part as a result of increased oxidative stress and inflammatory responses, particularly within the gastrointestinal tract. This study aimed to investigate whether plant-derived betaine and isoquinoline alkaloids could ameliorate HS in
Min Ho Han et al.
Toxicology letters, 220(2), 157-166 (2013-05-11)
We examined the effects of sanguinarine, a benzophenanthridine alkaloid, on reactive oxygen species (ROS) production and the association of these effects with apoptotic cell death in a human colorectal cancer HCT-116 cell line. Sanguinarine generated ROS, which was followed by

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