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Moligand™, analytical standard, ≥98% Analytical standard,Moligand™ for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Store at -20°C,Argon charged Ships Ice chest + Ice pads 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 26 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Silibinin, the main flavonoid extracted from the milk thistle Silybum marianum, displays hepatoprotective properties in acute and chronic liver injury.Silibinin itself is mixture of two diastereomers silibinin A and silybinin B in approximately equimolar ratio.
| Sonrisas canónicas | COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=C(C=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O |
|---|---|
| IUPAC Name | (2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one |
| InChIKey | SEBFKMXJBCUCAI-HKTJVKLFSA-N |
| INCHI | 1S/C25H22O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-16-5-3-12(7-18(16)34-24)25-23(31)22(30)21-15(29)8-13(27)9-19(21)35-25/h2-9,20,23-29,31H,10H2,1H3/t20-,23+,24-,25-/m1/s1 |
| Isómeros SMILES | COC1=C(C=CC(=C1)[C@@H]2[C@H](OC3=C(O2)C=C(C=C3)[C@@H]4[C@H](C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O |
| WGK Alemania | 3 |
| RTECS | DJ2981770 |
| CAS alternativo | 36804-17-8;142797-34-0 |
| PubChem CID | 31553 |
| Peso molecular | 482.44 |
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 | Lignans, neolignans and related compounds |
| Clase | Flavonolignans |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Flavonolignans |
| Alternative Parents | 3-hydroxyflavonoids 5-hydroxyflavonoids 7-hydroxyflavonoids Flavanonols Phenylbenzo-1,4-dioxanes Chromones Methoxyphenols Benzo-1,4-dioxanes Phenoxy compounds Anisoles Methoxybenzenes Aryl alkyl ketones 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Para dioxins Vinylogous acids Secondary alcohols Oxacyclic compounds Polyols Organic oxides Primary alcohols Hydrocarbon derivatives |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Flavonolignan - Hydroxyflavonoid - 3-hydroxyflavonoid - Flavanonol - Flavanone - 7-hydroxyflavonoid - 5-hydroxyflavonoid - Flavan - Phenylbenzodioxane - 2-phenylbenzo-1,4-dioxane - Chromone - 1-benzopyran - Methoxyphenol - Benzopyran - Chromane - Benzodioxane - Benzo-1,4-dioxane - Phenoxy compound - Anisole - Methoxybenzene - Aryl alkyl ketone - Aryl ketone - Phenol ether - Alkyl aryl ether - 1-hydroxy-2-unsubstituted benzenoid - Phenol - 1-hydroxy-4-unsubstituted benzenoid - Benzenoid - Para-dioxin - Monocyclic benzene moiety - Vinylogous acid - Secondary alcohol - Ketone - Polyol - Organoheterocyclic compound - Ether - Oxacycle - Alcohol - Organooxygen compound - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Primary alcohol - Aromatic heteropolycyclic compound |
| Descripción | This compound belongs to the class of organic compounds known as flavonolignans. These are non-conventional lignans that derived from flavonoids. They are characterized by a p-dioxin ring substituted at one carbon atom by a C3C6 (phenylpropan) group and fused to the B-ring of the 2-phenylchromene moiety. |
| External Descriptors | aromatic ether - polyphenol - benzodioxine - flavonolignan |
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| Sensibilidad | air sensitive;heat sensitive |
|---|---|
| Peso molecular | 482.400 g/mol |
| XLogP3 | 2.400 |
| Hydrogen Bond Donor Count | 5 |
| Hydrogen Bond Acceptor Count | 10 |
| Rotatable Bond Count | 4 |
| Exact Mass | 482.121 Da |
| Monoisotopic Mass | 482.121 Da |
| Topological Polar Surface Area | 155.000 Ų |
| Heavy Atom Count | 35 |
| Formal Charge | 0 |
| Complexity | 750.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 4 |
| 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. Shuai-Nan Zhang, Qi Liu, Xu-Zhao Li, Wu-De Yang, Ying Zhou. (2023) Liver protein and metabolite biolabels reveal hepatoprotective effects and active compounds of Eucommiae folium: Exploration of new application of herb based on multi-omics and bioinformatics. JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, [PMID:38008044] [10.1016/j.jpba.2023.115870] |
| 2. Yanan Wang, Huichao Wei, Keyang Li, Liru Liu, Yingfei Zhu, Xinyuan Wang, Jiahui Yan, Liangmin Yu, Xuefeng Yan, Zhiyu He. (2023) Ros-responsive dextran-phenylboronic acid-silibinin nanoparticles for targeting delivery of BAPTA-AM to effectively eliminate calcium overload-mediated inflammatory cascades and mitochondrial apoptosis: Alleviating acute liver injury. CHEMICAL ENGINEERING JOURNAL, [PMID:] [10.1016/j.cej.2023.148283] |
| 3. Guanglu Wang, Yue Xin, Kaixin Ping, Xuhui Xu, Ying Sun, Xing Li, Xinying Guan, Jingquan Dong. (2023) Silybin mitigates chronic Avermectin exposure-induced intestinal damage and growth inhibition in carp. ENVIRONMENTAL TOXICOLOGY AND PHARMACOLOGY, [PMID:38135203] [10.1016/j.etap.2023.104351] |
| 4. Pan En-Zhuang, Xin Yue, Li Xue-Qing, Wu Xin-Yu, Tan Xue-Lian, Dong Jing-Quan. (2023) Ameliorative effects of silybin against avermectin-triggered carp spleen mitochondrial dysfunction and apoptosis through inhibition of PERK-ATF4-CHOP signaling pathway. FISH PHYSIOLOGY AND BIOCHEMISTRY, [PMID:37542703] [10.1007/s10695-023-01228-y] |
| 5. Yanxia Liu, Minghuo Wu, Miaomiao Ren, Haijun Bao, Qing’an Wang, Nan Wang, Shibo Sun, Jianqiang Xu, Xiaojing Yang, Xu Zhao, Yongming Bao, Gaohong He, Weiping Xu. (2023) From Medical Herb to Functional Food: Development of a Fermented Milk Containing Silybin and Protein from Milk Thistle. Foods, 12 (6): (1308). [PMID:36981234] [10.3390/foods12061308] |
| 6. Qiang-Ming Li, Xiu-Rong Yang, Xue-Qiang Zha, Li-Hua Pan, Dan-Dan Zang, Feng-Yun Zhang, Jian-Ping Luo. (2022) Protective Effects of Three Flavonoids from Dendrobium huoshanense Flowers on Alcohol-Induced Hepatocyte Injury via Activating Nrf2 and Inhibiting NF-κB Pathways. CHEMISTRY & BIODIVERSITY, 19 (8): (e202200471). [PMID:35774029] [10.1002/cbdv.202200471] |
| 7. Rong Xu, Siyan Qiu, Jie Zhang, Xiaoli Liu, Ling Zhang, Haizhu Xing, Min You, Man Wang, Yuting Lu, Peng Zhang, Jing Zhu. (2022) Silibinin Schiff Base Derivatives Counteract CCl4-Induced Acute Liver Injury by Enhancing Anti-Inflammatory and Antiapoptotic Bioactivities. Drug Design Development and Therapy, [PMID:35601675] [10.2147/DDDT.S356847] |
| 8. Xinran Shi, Liang Ji, Yuanyuan Hu, Jinyu Gu, Liming Wang, Wenwen Lu, Jiali Meng, Yan Du, Lingzhong Huang, Dongxia Nie, Yanyan Yu. (2022) Dual-responsive zeolitic imidazolate framework-90 for the combined detection and intracellular imaging of ATP and ROS. SENSORS AND ACTUATORS B-CHEMICAL, [PMID:] [10.1016/j.snb.2022.131848] |
| 9. Bai Yang, Chen Jiaqi, Hu Weijian, Wang Lei, Wu Yulian, Yu Shi’an. (2022) Silibinin Therapy Improves Cholangiocarcinoma Outcomes by Regulating ERK/Mitochondrial Pathway. Frontiers in Pharmacology, [PMID:35401195] [10.3389/fphar.2022.847905] |
| 10. Yan Huang, Dandan Pu, Zhilin Hao, Xiao Yang, Yuyu Zhang. (2021) The Effect of Prickly Ash (Zanthoxylum bungeanum Maxim) on the Taste Perception of Stewed Sheep Tail Fat by LC-QTOF-MS/MS and a Chemometrics Analysis. Foods, 10 (11): (2709). [PMID:34828990] [10.3390/foods10112709] |
| 11. Jichen Yang, Huan Li, Xiaoli Wang, Chuanying Zhang, Guo Feng, Xin Peng. (2021) Inhibition Mechanism of α-Amylase/α-Glucosidase by Silibinin, Its Synergism with Acarbose, and the Effect of Milk Proteins. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, [PMID:34463509] [10.1021/acs.jafc.1c01765] |
| 12. Meirong Huo, Honglan Wang, Ying Zhang, Han Cai, Pan Zhang, Lingchao Li, Jianping Zhou, Tingjie Yin. (2020) Co-delivery of silybin and paclitaxel by dextran-based nanoparticles for effective anti-tumor treatment through chemotherapy sensitization and microenvironment modulation. JOURNAL OF CONTROLLED RELEASE, [PMID:32044390] [10.1016/j.jconrel.2020.02.017] |
| 13. Sun Hui-ping, Su Jing-han, Meng Qing-shuo, Yin Qi, Zhang Zhi-wen, Yu Hai-jun, Zhang Peng-cheng, Wang Si-ling, Li Ya-ping. (2016) Silibinin and indocyanine green-loaded nanoparticles inhibit the growth and metastasis of mammalian breast cancer cells in vitro. ACTA PHARMACOLOGICA SINICA, 37 (7): (941-949). [PMID:27133295] [10.1038/aps.2016.20] |
| 14. Yong Li, Youdong Zhou, Yinqiu Tan, Gang Deng. (2025) Anti-Inflammatory Treatment of Subarachnoid Hemorrhage by Self-Assembled Silymarin Nanoparticles. Small Science, [PMID:40657200] [10.1002/smsc.202400322] |
| 15. Shuai-nan Zhang, Qi Liu, Xu-zhao Li. (2024) Combination of omics, bioinformatics, molecular docking, and experimental validation to elucidate the hepatoprotective effects, mechanisms, and active compounds of Shandougen. BIOMEDICAL CHROMATOGRAPHY, 38 (7): (e5887). [PMID:38751131] [10.1002/bmc.5887] |
| 16. Yuanbin Li, Wu Yi, Haowei Chen, Bao Han, Bo Ruan, Zhong Xiaoyu, Li ShanShan, Yifan Chen, Tao Peng, Jiaheng Zhang, Fang Wang. (2024) Enhancement of silymarin solubility and bioactivities using betaine/ascorbyl glucoside DES. NEW JOURNAL OF CHEMISTRY, [PMID:] [10.1039/D4NJ03748K] |
| 17. Jianying Liu, Yan Chen, Zhifeng Cen, Meiqi Hong, Binzhi Zhang, Xia Luo, Leqi Wang, Shasha Li, Xue Xiao, Qinqiang Long. (2025) Ganoderma lucidum spore oil attenuates acute liver injury by modulating lipid metabolism and gut microbiota. JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, [PMID:39842075] [10.1016/j.jpba.2025.116674] |
| 18. Ling Jiang, Cai-Bo Tian, Rui-Han Ye, Nian Shi, Xing-Chao He, Yun-Li Zhao, Xiao-Dong Luo. (2024) Kakuol and asarinin protecting liver injury via HSP90AA1/CDK2/mTOR signaling pathway. FITOTERAPIA, [PMID:39551106] [10.1016/j.fitote.2024.106297] |
| 19. Jie Li, Xiujuan Yang, Xiaolong Lian, Baojian Li, Quhuan Ma, Lingling Yang, Guangmiao Gao, Yi Deng, Zhijun Yang. (2025) Licorice attenuates cisplatin-induced hepatotoxicity by alleviating endoplasmic reticulum stress and apoptosis. Frontiers in Pharmacology, [PMID:40183095] [10.3389/fphar.2025.1557125] |
| 20. Yifu Lyu, Xiuyi Yang, Lei Yang, Jinyu Dai, Huanyu Qin, Yunuo Zhou, Yunan Huang, Yanmei Wang, Di Wu, Qindai Shuai, Qilong Li, Xiaofei Xin, Lifang Yin. (2024) Lipid nanoparticle-mediated hepatocyte delivery of siRNA and silibinin in metabolic dysfunction-associated steatotic liver disease. JOURNAL OF CONTROLLED RELEASE, [PMID:38972640] [10.1016/j.jconrel.2024.07.011] |
| 21. Xinyu Wu, Jiawei Chen, Kaixin Ping, Yan Xia, Mengxin Li, Yannan Xiang, Huimao Feng, Jingquan Dong. (2024) Silybin mitigated liver and brain damage after difenoconazole exposure: Crosstalk between oxidative stress, inflammation, ferroptosis and apoptosis. PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY, [PMID:38879300] [10.1016/j.pestbp.2024.105942] |
| 22. Yan Baofei, Zheng Xian, Lu Danya, Li Ting, Chen Xi, Shao Zhitao, Fu Tingming. (2025) Silibinin-drived microbiota enrich (R)-2,3-dihydroxy-isovalerate and ameliorate colitis via the GAT-3/RARβ/RORγt axis. ISME Journal, [PMID:40801260] [10.1093/ismejo/wraf175] |
| 23. Pengfei Xu, Qi Yin, Jianan Shen, Lingli Chen, Haijun Yu, Zhiwen Zhang, Yaping Li. (2013) Synergistic inhibition of breast cancer metastasis by silibinin-loaded lipid nanoparticles containing TPGS. INTERNATIONAL JOURNAL OF PHARMACEUTICS, [PMID:23830941] [10.1016/j.ijpharm.2013.06.053] |
| 24. Xiaowen Wang, Xia Jiang, Jinjing Yang, Michael Adu-Frimpong, Mingjie Gong, Qinyang Hua, Tingyuan Li, Jiaying Li, Pengfei Pan, Elmurat Toreniyazov, Xia Cao, Jiangnan Yu, Qilong Wang, Ximing Xu. (2025) Preparation of chitosan-modified Moringa A liposomes and its protective effect on acute alcoholic liver injury. JOURNAL OF LIPOSOME RESEARCH, [PMID:40538369] [10.1080/08982104.2025.2516033] |
| 25. Tao Sheng, Shuai Xia, Jia-Min Li, Ruo-bin Peng, Pingbo Yan, Bing-Feng Zhang. (2025) Hybrid prodrug-nanoassemblies coated by chitosan exerted antioxidant and anti-inflammatory effect on liver fibrosis. INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, [PMID:41482224] [10.1016/j.ijbiomac.2025.149981] |
| 26. Bailin Li, Fen Liu, Yaoguang Huang, Sui Kiat Chang, Chenqi Niu, Pu Liu, Xiancai Li, Liyuan Yao, Sheng-Xiang Qiu. (2026) Cajanstilbenoid A from Pigeon Pea: A Functional Food Component for Managing High-Fat Diet-Induced Hepatic Steatosis via PPARα Activation. Journal of Future Foods, [PMID:] [10.1016/j.jfutfo.2026.03.004] |
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