Berberrubine chloride

Base Information

• Chemical Name: Berberrubine chloride
• CAS No.: 15401-69-1
• Molecular Formula: C19H16 N O4 . Cl
• Molecular Weight: 357.793
• NSC Number: 96347
• Metabolomics Workbench ID: 122870
• ChEMBL ID: CHEMBL1223099
• Mol file: 15401-69-1.mol

Synonyms:5,6-dihydro-9-hydroxy-10-methoxybenzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium chloride;9-berberoline chloride;berberrubine;berberrubine chloride

Chemical Property of Berberrubine chloride

Chemical Property:

• Vapor Pressure: 4.28E-15mmHg at 25°C
• Melting Point: 245℃ (DEC.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 51.80000
• Density: g/cm³
• LogP: -0.20270
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 357.0767857
• Heavy Atom Count: 25
• Complexity: 474

Purity/Quality:

99% ^*data from raw suppliers

Berberrubine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC5=C(C=C4CC3)OCO5)O.[Cl-]
• Uses: Berberrubine Chloride is a novel alkaloid with novel nitric-oxide donating activity. Antitumor and an antimicrobial agent.

Technology Process of Berberrubine chloride

There total 14 articles about Berberrubine chloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

berberine chloride (633-65-8) → berberrubine chloride (15401-69-1)

Guidance literature:

at 180 ℃; for 0.333333h;

DOI:10.1016/j.bmcl.2014.02.032

Reference yield: 98.0%

berberrubine (108275-17-8,6847-93-4) → berberrubine chloride (15401-69-1)

Guidance literature:

With hydrogenchloride; In ethanol; water; at 20 ℃; for 8h;

Reference yield: 90.0%

berberrubine (17388-19-1) → berberrubine chloride (15401-69-1)

Guidance literature:

With hydrogenchloride; In water; acetonitrile; at 20 ℃; for 3h;

DOI:10.1080/14786419.2017.1350669

upstream raw materials:

berberrubine

berberine chloride

berberrubine

berberine chloride hydrate

Downstream raw materials:

2,3-methenedioxy-9-cinnamate-10-methoxyprotoberberine chloride

Refernces

• 1、 Jana, Gopal Chandra,Nayim, Sk,Sahoo, Nandan Kumar,Das, Somnath,Aktara, Mt Nasima,Patra, Anirudha,Islam, Md. Maidul,Hossain, Maidul. "Deciphering the positional impact of chlorine in a new series of berberine analogues towards the superb-selective "turn-on" hydrophobic signaling of bovine serum albumin at physiological pH". . p. 1761 - 1771. Retrieved 2020.
• 2、 Iwasa,Kamigauchi,Ueki,Taniguchi. "Antibacterial activity and structure-activity relationships of berberine analogs". . p. 469 - 478. Retrieved 1996.
• 3、 Sobolova, Katerina,Hrabinova, Martina,Hepnarova, Vendula,Kucera, Tomas,Kobrlova, Tereza,Benkova, Marketa,Janockova, Jana,Dolezal, Rafael,Prchal, Lukas,Benek, Ondrej,Mezeiova, Eva,Jun, Daniel,Soukup, Ondrej,Korabecny, Jan. "Discovery of novel berberine derivatives with balanced cholinesterase and prolyl oligopeptidase inhibition profile". . . Retrieved 2020.
• 4、 Nechepurenko,Shirokova,Khvostov,Frolova,Sinitsyna,Maksimov,Bredikhin,Komarova,Fadeev,Luzina,Tolstikova,Salakhutdinova. "Synthesis, hypolipidemic and antifungal activity of tetrahydroberberrubine sulfonates". . p. 1052 - 1060. Retrieved 2019.
• 5、 Qin, Qi-Pin,Wang, Zhen-Feng,Huang, Xiao-Ling,Tan, Ming-Xiong,Luo, Zhi-Hui,Wang, Shu-Long,Zou, Bi-Qun,Liang, Hong. "Two telomerase-targeting Pt(ii) complexes of jatrorrhizine and berberine derivatives induce apoptosis in human bladder tumor cells". . p. 15247 - 15254. Retrieved 2019.
• 6、 Duan, Jun-Rong,Liu, Han-Bo,Jeyakkumar, Ponmani,Gopala, Lavanya,Li, Shuo,Geng, Rong-Xia,Zhou, Cheng-He. "Design, synthesis and biological evaluation of novel Schiff base-bridged tetrahydroprotoberberine triazoles as a new type of potential antimicrobial agents". . p. 907 - 916. Retrieved 2017.
• 7、 Milata, Viktor,Svedova, Alexandra,Barbierikova, Zuzana,Holubkova, Eva,Cipakova, Ingrid,Cholujova, Dana,Jakubikova, Jana,Panik, Miroslav,Jantova, Sona,Brezova, Vlasta,Cipak, Lubos. "Synthesis and anticancer activity of novel 9-O-substituted berberine derivatives". . . Retrieved 2019.
• 8、 Gao, Yu,Li, Mingxin,Ruan, Shutang,Wang, Shifa,Wang, Zhonglong,Wu, Suzhen,Yang, Lijuan,Yang, Yiqin,Zhang, Yan. "A novel berberine-based colorimetric and fluorometric probe for Hg2+ detection and its applications in water samples". . . Retrieved 2021.
• 9、 Wang, Rongchun,Rostyslav, Stoyka,Li, Xiaobin,Lin, Houwen,Zhang, Xuanming,Zhang, Shanshan,Liu, Kechun,Wang, Lizhen. "Synthetic and antitumor comparison of 9-O-alkylated and carbohydrate-modified berberine derivatives". . p. 3251 - 3260. Retrieved 2020.
• 10、 Li, Yan,Yuan, Xiao,Rong, Xianglu,Gao, Ying,Qiu, Zhibin,Zhang, Zhipeng,Zhou, Dongbin,Li, Weimin. "Design, synthesis and biological evaluation of a hybrid compound of berberine and magnolol for improvement of glucose and lipid metabolism". . p. 81924 - 81931. Retrieved 2016.