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Moligand™, 10mM in DMSO Moligand™ for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Store at -80°C Ships Dry ice packs + Cold packs Check lot-specific COA for exact specifications.
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 8 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Product Describtion:
Sanguinarine (Sanguinarin), a benzophenanthridine alkaloid derived from the root of Sanguinaria Canadensis, can stimulate apoptosis via activating the production of reactive oxygen species (ROS). Sanguinarine-induced apoptosis is associated with the activation of JNK and NF-κB. Sanguinarine (Pseudochelerythrine, Sanguinarin, Sanguinarium), a benzophenanthridine alkaloid known as an anti-inflammatory agent, is a potent inhibitor of NF-κB activation.
| Canonical Smiles | C[N+]1=C2C(=C3C=CC4=C(C3=C1)OCO4)C=CC5=CC6=C(C=C52)OCO6 |
|---|---|
| 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 |
| InChIKey | INVGWHRKADIJHF-UHFFFAOYSA-N |
| 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 |
| Isomeric SMILES | C[N+]1=C2C(=C3C=CC4=C(C3=C1)OCO4)C=CC5=CC6=C(C=C52)OCO6 |
| PubChem CID | 5154 |
| Molecular Weight | 332.33 |
Comprehensive hazard, handling, storage, and regulatory compliance document.
Download SDS →Lot-specific quality data. Enter your lot number to retrieve the exact COA.
Look up COA →Full quality attributes and acceptance criteria for this grade.
View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Alkaloids and derivatives |
| Class | Benzophenanthridine alkaloids |
| Subclass | Quaternary benzophenanthridine alkaloids |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Quaternary benzophenanthridine alkaloids |
| Alternative Parents | Phenanthridines and derivatives Naphthalenes Isoquinolines and derivatives Benzodioxoles Pyridinium derivatives Heteroaromatic compounds Oxacyclic compounds Azacyclic compounds Acetals Organopnictogen compounds Organonitrogen compounds Hydrocarbon derivatives Organic cations |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Quaternary benzophenanthridine alkaloid skeleton - Benzoquinoline - Phenanthridine - Isoquinoline - Naphthalene - Quinoline - Benzodioxole - Pyridine - Benzenoid - Pyridinium - Heteroaromatic compound - Azacycle - Oxacycle - Acetal - Organoheterocyclic compound - Organooxygen compound - Organonitrogen compound - Hydrocarbon derivative - Organic oxygen compound - Organic nitrogen compound - Organopnictogen compound - Organic cation - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as quaternary benzophenanthridine alkaloids. These are alkaloids containing a quaternary N-demethylbenzophenanthridine skeleton, where the nitrogen atom of the phenanthridine moiety is part of four bonds. |
| External Descriptors | a small molecule |
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| Molecular Weight | 332.300 g/mol |
|---|---|
| XLogP3 | 4.400 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 0 |
| Exact Mass | 332.092 Da |
| Monoisotopic Mass | 332.092 Da |
| Topological Polar Surface Area | 40.800 Ų |
| Heavy Atom Count | 25 |
| Formal Charge | 1 |
| Complexity | 530.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |
| 1. Xiang Zhou, Haojie Ye, Xiuhui Gao, Yumei Feng, Wubin Shao, Puying Qi, Zhibing Wu, Liwei Liu, Peiyi Wang, Song Yang. (2021) The discovery of natural 4'-demethylepipodophyllotoxin from renewable Dysosma versipellis species as a novel bacterial cell division inhibitor for controlling intractable diseases in rice. INDUSTRIAL CROPS AND PRODUCTS, [PMID:] [10.1016/j.indcrop.2021.114182] |
| 2. Chao Fan, Hao Tang, Licheng Wang, Yijing Li, Xusheng Wang, Shuai Wang, Xiaojing Liang. (2020) The preparation of a core–shell stationary phase by the in situ polymerization of a hydrophilic polymer on the surface of silica and its chromatographic performance. NEW JOURNAL OF CHEMISTRY, 44 (27): (11704-11709). [PMID:] [10.1039/D0NJ01197E] |
| 3. Yingzhi Hu, Huaidong Peng, Youshao Yan, Shuyu Guan, Shumei Wang, Paul C.H. Li, Yue Sun. (2017) Integration of laminar flow extraction and capillary electrophoretic separation in one microfluidic chip for detection of plant alkaloids in blood samples. ANALYTICA CHIMICA ACTA, [PMID:28864182] [10.1016/j.aca.2017.05.036] |
| 4. Ting Tan, Mingliang Zhang, Yiqun Wan, Hongdeng Qiu. (2015) Utilization of deep eutectic solvents as novel mobile phase additives for improving the separation of bioactive quaternary alkaloids. TALANTA, [PMID:26717817] [10.1016/j.talanta.2015.11.041] |
| 5. Yue Sun, Yuanyuan Li, Jiajian Zeng, Qixian Lu, Paul C.H. Li. (2015) Microchip electrophoretic separation and fluorescence detection of chelerythrine and sanguinarine in medicinal plants. TALANTA, [PMID:26003696] [10.1016/j.talanta.2015.04.008] |
| 6. Jing Zhu, Qing Hong Zhang, Wen Wu Wang. (2024) Pattern Recognition of Alkaloids by Inhibiting the Catalytic Activity of Dopzymes for Dopamine. ANALYTICAL CHEMISTRY, [PMID:39014901] [10.1021/acs.analchem.4c01920] |
| 7. Yaxuan Yue, Jing Liu, Chen Li, Fengfeng Chen, Cheng Yang, Bingtian Zhao. (2025) Pinosylvin and Sanguinarine Combination to Enhance Antifungal Activity against Candida albicans. JOURNAL OF MICROBIOLOGY AND BIOTECHNOLOGY, [PMID:40374536] [10.4014/jmb.2412.12055] |
| 8. Wen-Jing Zhao, Xin-Yue Wang, Jin-Shuang Wang, Yuan-Yuan Cui, Cheng-Xiong Yang. (2026) Efficient solid-phase extraction of quaternary ammonium alkaloids from traditional Chinese medicines on a novel sulfonic acid group functionalized microporous organic network coated SiO2 composite. JOURNAL OF CHROMATOGRAPHY A, [PMID:41621247] [10.1016/j.chroma.2026.466756] |
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