Dihydroberberine

Base Information

• Chemical Name: Dihydroberberine
• CAS No.: 483-15-8
• Molecular Formula: C20H19 N O4
• Molecular Weight: 337.375
• Hs Code.: 2934999090
• European Community (EC) Number: 683-111-2
• NSC Number: 331264
• DSSTox Substance ID: DTXSID70197476
• Nikkaji Number: J126.057J
• Wikidata: Q72466426
• Metabolomics Workbench ID: 46087
• ChEMBL ID: CHEMBL11848
• Mol file: 483-15-8.mol

Synonyms:dihydroberberine;dihydroberberine hydrochloride

Chemical Property of Dihydroberberine

Chemical Property:

• Vapor Pressure: 1.77E-12mmHg at 25°C
• Melting Point: 223-224ºC (dec.)
• Boiling Point: 557.8°Cat760mmHg
• PKA: 3.08±0.20(Predicted)
• Flash Point: 170.7°C
• PSA: 40.16000
• Density: 1.37g/cm³
• LogP: 3.24020
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 337.13140809
• Heavy Atom Count: 25
• Complexity: 538

Purity/Quality:

99%, ^*data from raw suppliers

Dihydroberberine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C2=C(C=C1)C=C3C4=CC5=C(C=C4CCN3C2)OCO5)OC
• Uses: Dihydroberberine is a derivative Berberine (B318150), an isoqinoline alkaloid shown to have a chemopreventive property against colon tumor formation by inhibiting the enzyme cyclooxygenase-2 (cox-2) which is abundantly expressed in colon cancer cells.

Technology Process of Dihydroberberine

There total 56 articles about Dihydroberberine 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) → 7,8-dihydroberberine (483-15-8)

Guidance literature:

With sodium tetrahydroborate; potassium carbonate; In methanol; at 0 ℃;

DOI:10.1016/j.bmcl.2008.11.088

Reference yield: 95.0%

Berberine acetate (36378-29-7) → 7,8-dihydroberberine (483-15-8)

Guidance literature:

With 10% Pt/activated carbon; hydrogen; sodium hydroxide; In tetrahydrofuran; at 20 - 30 ℃; for 8h; under 760.051 Torr;

Reference yield: 95.0%

Berberine nitrate → 7,8-dihydroberberine (483-15-8)

Guidance literature:

With potassium carbonate; isopropyl alcohol; at 20 - 80 ℃; for 12h; Inert atmosphere;

upstream raw materials:

Berberinol

berberine chloride

(R)-(+)-canadine

diethyl ether

Downstream raw materials:

(9,10-Dimethoxy-5,8,13,13a-tetrahydro-6H-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizin-13-yl)-acetic acid

C₂₃H₂₅NO₆

13-(2-bromobenzyl)berberine bromide

13-(3-bromobenzyl)berberine bromide

Refernces

• 1、 Tan,Wang, Yongfu,Ai, Gaoxiang,Luo, Chaodan,Chen, Hanbin,Li, Cailan,Zeng, Huifang,Xie, Jianhui,Chen, Jiannan,Su. "Dihydroberberine, a hydrogenated derivative of berberine firstly identified in Phellodendri Chinese Cortex, exerts anti-inflammatory effect via dual modulation of NF-κB and MAPK signaling pathways". . . Retrieved 2019.
• 2、 Fu, Shengnan,Xie, Yanqi,Tuo, Jue,Wang, Yalong,Zhu, Wenbo,Wu, Sihan,Yan, Guangmei,Hu, Haiyan. "Discovery of mitochondria-targeting berberine derivatives as the inhibitors of proliferation, invasion and migration against rat C6 and human U87 glioma cells". . p. 164 - 173. Retrieved 2015.
• 3、 Olleik, Hamza,Yacoub, Taher,Hoffer, Laurent,Gnansounou, Senankpon Martial,Benhaiem‐henry, Kehna,Nicoletti, Cendrine,Mekhalfi, Malika,Pique, Valérie,Perrier, Josette,Hijazi, Akram,Baydoun, Elias,Raymond, Josette,Piccerelle, Philippe,Maresca, Marc,Robin, Maxime. "Synthesis and evaluation of the antibacterial activities of 13‐substituted berberine derivatives". . p. 1 - 31. Retrieved 2020.
• 4、 Tang, Xuemei,Zhang, Jianhui,Liu, Liyan,Yang, Depo,Wang, Huaqiao,He, Feng. "Synthesis of 13-substituted derivatives of berberine: Aggregation-induced emission enhancement and pH sensitive property". . p. 71 - 81. Retrieved 2017.
• 5、 Fan, Tian–Yun,Wang, Yan–Xiang,Tang, Sheng,Hu, Xin–Xin,Zen, Qing–Xuan,Pang, Jing,Yang, Yuan–Shuai,You, Xue–Fu,Song, Dan–Qing. "Synthesis and antibacterial evaluation of 13-substituted cycloberberine derivatives as a novel class of anti-MRSA agents". . p. 877 - 886. Retrieved 2018.
• 6、 Bhowmik, Debipreeta,Buzzetti, Franco,Fiorillo, Gaetano,Orzi, Fabrizio,Syeda, Tanjia Monir,Lombardi, Paolo,Suresh Kumar, Gopinatha. "Synthesis of new 13-diphenylalkyl analogues of berberine and elucidation of their base pair specificity and energetics of DNA binding". . p. 226 - 231. Retrieved 2014.
• 7、 Li, Dong-Dong,Yu, Pan,Xu, Hui,Wang, Zhen-Zhong,Xiao, Wei,Zhao, Lin-Guo. "Discovery of C-9 modified berberine derivatives as novel lipid-lowering agents". . p. 59 - 66. Retrieved 2021/01/06.
• 8、 -. "Method for preparing 5, 8-dihydro-6H-isoquinoline [3, 2-alpha] isoquinoline based on micro-reaction system". Paragraph 0119; 0134-0135; 0136; 0150-0151; 0152; 0166; .... . Retrieved 2021/07/08.