Berberine Chloride Hydrate - analytical standard , CAS No.141433-60-5

CAS: 141433-60-5 Cat. No.: B107341 Peso molecular: 371.81 Beilstein Registry Number: 3836585 Número EC: 211-195-9

GRADE & PURITY Analytical standard

Synonyms

MFCD00149997 | Natural Yellow 18 | AC-4573 | 16,17-dimethoxy-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(13),2,4(8),9,14,16,18,20-octaene;chloride;hydrate | Kyoberin (TN) | FT-0631162 | Berberinium chloride hydrate | BCP28194 | SCHEM

Storage

Room temperature

Shipped In

Normal

Specifications

Sinónimos

MFCD00149997 | Natural Yellow 18 | AC-4573 | 16, 17-dimethoxy-5, 7-dioxa-13-azoniapentacyclo[11.8.0.02, 10.04, 8.015, 20]henicosa-1(13), 2, 4(8), 9, 14, 16, 18, 20-octaene;chloride;hydrate | Kyoberin (TN) | FT-0631162 | Berberinium chloride hydrate | BCP28194 | SCHEM

Especificaciones y pureza

analytical standard

Condiciones de almacenamiento de almacenamiento

Room temperature

Enviado en

Normal

Grado

Analytical standard

Nombres e identificadores

• Sonrisas canónicas: COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC5=C(C=C4CC3)OCO5)OC.O.[Cl-]
• IUPAC Name: 16,17-dimethoxy-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(13),2,4(8),9,14,16,18,20-octaene;chloride;hydrate
• InChIKey: BPNJXFPOPCFZOC-UHFFFAOYSA-M
• INCHI: 1S/C20H18NO4.ClH.H2O/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2;;/h3-4,7-10H,5-6,11H2,1-2H3;1H;1H2/q+1;;/p-1
• Isómeros SMILES: COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC5=C(C=C4CC3)OCO5)OC.O.[Cl-]
• WGK Alemania: 2
• CAS alternativo: 2086-83-1;633-65-8;68030-18-2
• Peso molecular: 371.81
• Beilstein: 3836585
• Reaxy-Rn: 14849287
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=14849287&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Alkaloids and derivatives
    • Clase Protoberberine alkaloids and derivatives

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• Clase: Protoberberine alkaloids and derivatives
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Protoberberine alkaloids and derivatives
• Alternative Parents: Isoquinolines and derivatives Benzodioxoles Anisoles Alkyl aryl ethers Pyridinium derivatives Heteroaromatic compounds Oxacyclic compounds Azacyclic compounds Acetals Organopnictogen compounds Organonitrogen compounds Organic oxides Organic chloride salts Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Protoberberine skeleton - Isoquinoline - Benzodioxole - Anisole - Alkyl aryl ether - Benzenoid - Pyridinium - Pyridine - Heteroaromatic compound - Oxacycle - Azacycle - Organoheterocyclic compound - Ether - Acetal - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organic chloride salt - Organic salt - Organooxygen compound - Organonitrogen compound - Aromatic heteropolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Propiedades químicas y físicas

• Punto de fusión (°C): 200°C
• Peso molecular: 389.800 g/mol
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 389.103 Da
• Monoisotopic Mass: 389.103 Da
• Topological Polar Surface Area: 41.800 Ų
• Heavy Atom Count: 27
• Formal Charge: 0
• Complexity: 488.000
• 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: 3

XLogP3

Referencias

1. Lijuan Xu, Xinzhong Hu, Liang Zou, Tian Ren.  (2023)  Preparation of photosensitive antibacterial nanocomposite film and its preservation effect on pork loin.  LWT-FOOD SCIENCE AND TECHNOLOGY,      [PMID:] [10.1016/j.lwt.2023.115586]

2. Li Chen, Meng Tian, Jing Yang, Zhenxu Wu.  (2023)  Berberine-Encapsulated Poly(lactic-co-glycolic acid)–Hydroxyapatite (PLGA/HA) Microspheres Synergistically Promote Bone Regeneration with DOPA-IGF-1 via the IGF-1R/PI3K/AKT/mTOR Pathway.  INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES,  24  (20): (15403).  [PMID:37895083] [10.3390/ijms242015403]

3. Peng Xiong, Yang Yuping, Guo Chenqi, He Qin, Li Yan, Gong Tao, Li Jia.  (2023)  A sustained-release phospholipid-based phase separation gel loaded with berberine for treating rheumatoid arthritis.  Frontiers in Pharmacology,      [PMID:37547331] [10.3389/fphar.2023.1210129]

4. Lin Yang, Chun-Feng Cheng, Zhi-Fang Li, Xiao-Jing Huang, Shao-Qing Cai, Shan-Yu Ye, Li-Jun Zhao, Yi Xiong, Dong-Feng Chen, He-Lu Liu, Zhen-Xing Ren, Hong-Cheng Fang.  (2023)  Berberine blocks inflammasome activation and alleviates diabetic cardiomyopathy via the miR‑18a‑3p/Gsdmd pathway.  INTERNATIONAL JOURNAL OF MOLECULAR MEDICINE,  51  (6): (1-13).  [PMID:37114562] [10.3892/ijmm.2023.5252]

5. Jin Pian, Zhu Fucheng, Jiang Mi, Takafuji Makoto, Ihara Hirotaka, Nie Lei, Liu Houmei.  (2022)  Carbonized π-conjugated polymer-coated porous silica: preparation and evaluating its extraction ability for berberine.  MICROCHIMICA ACTA,  189  (11): (1-15).  [PMID:36190563] [10.1007/s00604-022-05496-y]

6. Shuai Wang, Yifan Zhang, Jianwei Lou, Hui Yong, Shulin Shan, Zhidan Liu, Mingxue Song, Cuiqin Zhang, Ruirui Kou, Zhaoxiong Liu, Wenhao Yu, Xiulan Zhao, Fuyong Song.  (2022)  The therapeutic potential of berberine chloride against SARM1-dependent axon degeneration in acrylamide-induced neuropathy.  PHYTOTHERAPY RESEARCH,  37  (1): (77-88).  [PMID:36054436] [10.1002/ptr.7594]

7. Hu Hong, Xu Kexing, Wang Kunping, Zhang Feng, Bai Xi.  (2022)  Dissecting the Effect of Berberine on the Intestinal Microbiome in the Weaned Piglets by Metagenomic Sequencing.  Frontiers in Microbiology,      [PMID:35464928] [10.3389/fmicb.2022.862882]

8. Ying-kun Zhi, Jing Li, Lang Yi, Rui-li Zhu, Jin-fang Luo, Qing-ping Shi, Sha-sha Bai, Yan-wu Li, Qun Du, Jia-zhong Cai, Liang Liu, Pei-xun Wang, Hua Zhou, Yan Dong.  (2022)  Sinomenine inhibits macrophage M1 polarization by downregulating α7nAChR via a feedback pathway of α7nAChR/ERK/Egr-1.  PHYTOMEDICINE,      [PMID:35397284] [10.1016/j.phymed.2022.154050]

9. Hao Yuan, Wan Li, Chengwu Song, Rongzeng Huang.  (2022)  An injectable supramolecular nanofiber-reinforced chitosan hydrogel with antibacterial and anti-inflammatory properties as potential carriers for drug delivery.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:35149101] [10.1016/j.ijbiomac.2022.02.015]

10. Xiao Tu, Chenxi Duan, Siwei Wu, Shengli Fu, Jianmin Ye.  (2021)  Identification of plumbagin as an effective chemotherapeutic agent for treatment of Gyrodactylus infections.  AQUACULTURE,      [PMID:] [10.1016/j.aquaculture.2021.736372]

11. Shen Zhu-qing, Wang Juan, Tan Wen-fu, Huang Tao-min.  (2020)  Berberine inhibits colorectal tumor growth by suppressing SHH secretion.  ACTA PHARMACOLOGICA SINICA,  42  (7): (1190-1194).  [PMID:32958873] [10.1038/s41401-020-00514-2]

12. Zhen Cheng, Hongcen Dong, Jiaman Liang, Fang Zhang, Xianping Chen, Lingling Du, Kejun Tan.  (2018)  Highly selective fluorescent visual detection of perfluorooctane sulfonate via blue fluorescent carbon dots and berberine chloride hydrate.  SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY,      [PMID:30253323] [10.1016/j.saa.2018.09.028]

13. Lu Jianrao, Yi Yang, Pan Ronghua, Zhang Chuanfu, Han Haiyan, Chen Jie, Liu Wenrui.  (2017)  Berberine protects HK-2 cells from hypoxia/reoxygenation induced apoptosis via inhibiting SPHK1 expression.  Journal of Natural Medicines,  72  (2): (390-398).  [PMID:29260413] [10.1007/s11418-017-1152-z]

14. Yuhan Yang, Feifei Han, Jin Ouyang, Yunling Zhao, Juan Han, Na Na.  (2015)  In-situ nanoelectrospray for high-throughput screening of enzymes and real-time monitoring of reactions.  ANALYTICA CHIMICA ACTA,      [PMID:26703263] [10.1016/j.aca.2015.10.032]

15. Shaoqi Qu, Shuo Yang, Qingjun Xu, Mengying Zhang, Feng Gao, Yongning Wu, Lin Li.  (2024)  A Milk Extracellular Vesicle-Based Nanoplatform Enhances Combination Therapy Against Multidrug-Resistant Bacterial Infections.  Advanced Science,      [PMID:39721033] [10.1002/advs.202406496]

16. Min Du, Xinran Liu, Xu Ji, Yue Wang, Xiaodan Liu, Chunfang Zhao, Erhui Jin, Youfang Gu, Hongyu Wang, Feng Zhang.  (2025)  Berberine alleviates enterotoxigenic Escherichia coli-induced intestinal mucosal barrier function damage in a piglet model by modulation of the intestinal microbiome.  Frontiers in Nutrition,      [PMID:39877539] [10.3389/fnut.2024.1494348]

17. Wang Yue, Zhang Ziting, Du Min, Ji Xu, Liu Xiaodan, Zhao Chunfang, Pang Xunsheng, Jin Erhui, Wen Aiyou, Li Shenghe, Zhang Feng.  (2024)  Berberine alleviates ETEC-induced intestinal inflammation and oxidative stress damage by optimizing intestinal microbial composition in a weaned piglet model.  Frontiers in Immunology,      [PMID:39351242] [10.3389/fimmu.2024.1460127]

18. Lu Li, Bo Lin, Yu Ting, Maohui Li, Jinjin Hu, Jingjing Song, Yingjuan Yan, Jiaxin Chen, Hong Xiao, Nengguo Tao.  (2024)  Berberine hydrochloride delays citrus sour rot mainly by disrupting carbohydrate and energy metabolism of Geotrichum citri-aurantii spores.  PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY,      [PMID:38879325] [10.1016/j.pestbp.2024.105933]

19. Lijuan Xu, Rongqiang Chen, Tian Ren.  (2025)  Fabrication of gelatin-based photodynamic food packaging with dual-antimicrobial activity for enhanced pork preservation.  FOOD HYDROCOLLOIDS,      [PMID:] [10.1016/j.foodhyd.2025.111361]

20. Li Wei, Jiao Ruofeng, Luo Shiyi, Liu Zefei, Song Jukun, Chen Zhu.  (2024)  Mechanism of action of Coptidis Rhizome in treating periodontitis based on network pharmacology and in vitro validation.  BMC Oral Health,  24  (1): (1-12).  [PMID:38704553] [10.1186/s12903-024-04311-9]

21. Hao Yuan, Zhaoxiang Zeng, Dongru Li, Rongzeng Huang, Wan Li.  (2024)  Multifunctional thiolated chitosan/puerarin composite hydrogels with pH/glutathione dual responsiveness for potential drug carriers.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:38553389] [10.1016/j.ijbiomac.2024.130841]

22. Ting Li, Shaojiao Song, Wei Lu, Yu Cao, Xin Zheng, Qiuyue Zhao, Hailong Wang.  (2025)  Nanopore characterization of DNA–COR–DNA duplex and the sensitive detection of coralyne.  SENSORS AND ACTUATORS B-CHEMICAL,      [PMID:] [10.1016/j.snb.2025.137407]

23. Yu Cheng, Zhenning Yan, Liuyang Hu.  (2025)  Unveiling the binding details of berberine mid-chain fatty acid salts on lysozyme: Multi-spectroscopy and molecular docking.  SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY,      [PMID:40925067] [10.1016/j.saa.2025.126902]

24. Wenxian Chen, Tongzhu Jin, Yilin Xie, Changsheng Zhong, Huiying Gao, Lei Zhang, Jin Ju, Ting Cheng, Mengyang Li, Huifang Wang, Zhenbo Yang, Qin Deng, Zhimin Du, Haihai Liang.  (2025)  Berberine partially ameliorates cardiolipotoxicity in diabetic cardiomyopathy by modulating SIRT3-mediated lipophagy to remodel lipid droplets homeostasis.  BRITISH JOURNAL OF PHARMACOLOGY,      [PMID:40222752] [10.1111/bph.70035]

25. Chen Zhang, Junyu Qian, Yuanhao Wang, Binbin Wang, Deli Wang, Sheng Dai, Haotian Qin.  (2025)  An injectable phosphocreatine-grafted gelatin hydrogel incorporating berberine-loaded copper-carbon dot nanozymes for osteoporotic bone regeneration.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2025.169983]

26. Li Jiameng, Liu Xiaodan, Sun Chaofan, Wang Mingyang, Zhang Qianqian, Wang Hongyu, Ji Xu, Jin Erhui, Zhang Feng.  (2025)  Metabolomics reveals the hindgut metabolic changes and physiological impacts in weaned piglets subjected to ETEC infection and berberine intervention.  Scientific Reports,  15  (1): (1-15).  [PMID:41131200] [10.1038/s41598-025-21011-8]

27. Houyin Zhou, Kun Guo, Jingzhi Yang, Gul Umair, Xianhui Yin, Yue Ma, Jun Yuan.  (2025)  First report of Fusarium oxysporum causing fruit spot disease on Prunus salicina in China and evaluation of effective fungicides for control.  PHYSIOLOGICAL AND MOLECULAR PLANT PATHOLOGY,      [PMID:] [10.1016/j.pmpp.2025.103041]