483-15-8

Basic information

• Product Name: dihydroberberine
• Synonyms: dihydroberberine;5,8-Dihydro-9,10-dimethoxy-6H-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine;9,10-Dimethoxy-2,3-(methylenedioxy)-13,13a-didehydroberbine;Nsc331264;DihydrouMbellatine;9,10-DiMethoxy-6,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinoline;Dihydroberberine/Dihydroumbellatine;9,10-Dimethoxy-2,3-(methylenedioxy)-13,13a-didehydrob
• CAS NO: 483-15-8
• Molecular Formula: C₂₀H₁₉NO₄
• Molecular Weight: 337.37
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 483-15-8.mol
• Article Data: 45

Chemical Properties

• Melting Point: 223-224℃ (dec.)
• Boiling Point: 557.8°Cat760mmHg
• Flash Point: 170.7°C
• Appearance: /
• Density: 1.37±0.1 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 1.77E-12mmHg at 25°C
• Refractive Index: 1.678
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 3.08±0.20(Predicted)
• CAS DataBase Reference: dihydroberberine(CAS DataBase Reference)
• NIST Chemistry Reference: dihydroberberine(483-15-8)
• EPA Substance Registry System: dihydroberberine(483-15-8)

Safety Data

• Hazardous Substances Data: 483-15-8(Hazardous Substances Data)

Usage

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.

InChI:InChI=1/C20H19NO4/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/h3-4,7-9H,5-6,10-11H2,1-2H3

Upstream product

• 10134-52-8 Berberinol 
• 633-65-8 berberine chloride 
• 264625-29-8 2-(benzo[d][1,3]dioxol-5-yl)-N-(2,3-dimethoxybenzyl)ethan-1-amine 
• 131543-46-9 Glyoxal 
• 36378-29-7 Berberine acetate 
• 1484-85-1 3,4-methylenedioxyphenylethylamine 
• 549-21-3 oxyberberine 
• 75767-29-2 Oxyberberine-13-carboxaldehyde 
• 53811-50-0 6-bromo-2,3-dimethoxybenzaldehyde 
• 94143-83-6 5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline 
• 2086-83-1 berberine 
• 86-51-1 2,3-dimethyoxybenzaldehyde 
• 113557-39-4 2-(2-bromo-4,5-methylenedioxyphenethyl)-7,8-dimethoxy-4-methylthio-1,2,3,4-tetrahydroisoquinolin-3-one 

Downstream Products

• 248261-91-8 13-(4-t-butylbenzyl)dihydroberberine 
• 54260-73-0 2,3-methylenedioxy-9,10-dimethoxy-13-ethylprotoberberine chloride 
• 54260-74-1 2,3-methylenedioxy-9,10-dimethoxy-13-n-propylprotoberberine chloride 
• 1261594-79-9 (9,10-Dimethoxy-5,8,13,13a-tetrahydro-6H-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizin-13-yl)-acetic acid 
• 1307911-33-6 C₂₃H₂₅NO₆ 
• 1390654-18-8 13-(2-bromobenzyl)berberine bromide 
• 1390654-16-6 13-(3-bromobenzyl)berberine bromide 
• 1390654-15-5 13-(4-bromobenzyl)berberine bromide 
• 1390654-28-0 13-(2-fluorobenzyl)-9,10-dimethoxy-5H-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinoline-7-iumbromide 
• 1390654-45-1 13-(4-methoxybenzyl)berberine bromide 
• 1390654-24-6 13-(4-fluorobenzyl)berberine bromide 
• 1390654-32-6 13-(3-nitrobenzyl)berberine bromide 
• 1390654-36-0 13-(3-methylbenzyl)berberine bromide 
• 1390654-33-7 13-(2-nitrobenzyl)berberine bromide 

Relevant articles and documents

Synthesis of new dihydroberberine and tetrahydroberberine analogues and evaluation of their antiproliferative activity on NCI-H1975 cells

Dihydroberberine (DHBER), the partially reduced form of the alkaloid berberine (BER), is known to exhibit important biological activities. Despite this fact, there have been only few studies that concern the biological properties of functionalized DHBER.

A new fluorescent probe for sensing of biothiols and screening of acetylcholinesterase inhibitors

A new N2O-type BODIPY probe (LF-Bop) has been proposed for the selective and sensitive detection of biologically relevant small molecular thiols. This detection is based on the Michael addition reaction between the thiol and nitrostyrene groups in the probe, which decreases the quenching effect from the nitro group, thus resulting in the recovery of the deep-red fluorescence from the BODIPY structure. The results show that LF-Bop is able to detect all tested free thiols through a fluorescence turn-on assay. The lowest limit of detection (LOD) for glutathione was found to be down to nanomolar levels (220 nM). Based on this probe, we have developed a new fluorescence assay for the screening of acetylcholinesterase inhibitors. In total, 11 natural and synthetic alkaloids have been evaluated. Both experimental measurements and theoretical molecular docking results reveal that both natural berberine and its synthetic derivative dihydroberberine are potential inhibitors of acetylcholinesterase.

Synthesis and structure of dihydroberberine nitroaryl derivatives – Potential ligands for G-quadruplexes

(Figure Presented) A method was developed for the synthesis of dihydroberberine nitroaryl derivatives on the basis of dihydroberberine reactions with aromatic electrophiles (picryl chloride, 4-chloro-7-nitrobenzofurazan, 4-chloro-5,7-dinitrobenzofurazan, and 7-chloro-4,6-dinitrobenzofuroxan). The obtained 13-substituted dihydroberberine derivatives represent structures with significant intramolecular charge transfer and, according to the results of molecular docking analysis, can effectively bind with G-quadruplexes of telomeric DNA fragments.

Visualizing semipermeability of the cell membrane using a pH-responsive ratiometric AIEgen

In clinical chemotherapy, some basic drugs cannot enter the hydrophobic cell membrane because of ionization in the acidic tumor microenvironment, a phenomenon known as ion trapping. In this study, we developed a method to visualize this ion trapping phenomenon by utilizing a pH-responsive ratiometric AIEgen, dihydro berberine (dhBBR). By observing the intracellular fluorescence ofdhBBR, we found that non-ionizeddhBBRcan enter cells more easily than ionized forms, which is in accordance with the concept of ion trapping. In addition,dhBBRshows superior anti-photobleaching ability toCurcuminthanks to its AIE properties. These results suggest thatdhBBRcan serve as a bioprobe for ion trapping.

Solution and Solid-State Analysis of Binding of 13-Substituted Berberine Analogues to Human Telomeric G-quadruplexes

The interaction between 13-phenylalkyl and 13-diphenylalkyl berberine derivatives (NAX) and human telomeric DNA G4 structures has been investigated by both spectroscopic and crystallographic methods. NAX042 and NAX053 are the best compounds improving the performance of the natural precursor berberine. This finding is in agreement with the X-ray diffraction result for the NAX053-Tel12 adduct, showing the ligand which interacts via π-stacking, sandwiched at the interface of two symmetry-related quadruplex units, with its benzhydryl group contributing to the overall stability of the adduct by means of additional π-stacking interactions with the DNA residues. The berberine derivatives were also investigated for their cytotoxic activity towards a panel of human cancer cell lines. Compounds NAX042 and NAX053 affect the viability of cancer cell lines in a dose-dependent manner.

Synthesis and anticancer activity of novel 9,13-disubstituted berberine derivatives

Novel berberine derivatives with disubstituents on positions C9 and C13 were synthesized and evaluated for antiproliferative activities against human prostate cancer cell lines (PC3 and DU145), breast cancer cell line (MDA-MB-231) and human colon cancer cell lines (HT29 and HCT116). All compounds showed significantly enhanced antiproliferative activities compared with berberine. Notably, compound 18e exhibited the strongest cytotoxicity against PC3 cells with an IC50 value of 0.19 μM, and the highest selectivity index (SIPC3 > 20). Further studies showed that 18e could arrest the cell cycle at G1 phase, and significantly inhibit tumor cell colony forming and migration even at low concentrations. Interestingly, 18e could significantly induce cytoplasmic vacuolation, suggesting a different mode of action from berberine.

Method for preparing 5, 8-dihydro-6H-isoquinoline [3, 2-alpha] isoquinoline based on micro-reaction system

The invention provides a method for preparing 5, 8-dihydro-6H-isoquinoline [3, 2-alpha] isoquinoline based on a micro-reaction system. A first solution and a second solution are introduced into a first micro-mixer through a feeding pump to be mixed; a mixture of an arylethylamine solution and an aryl aldehyde solution is pumped into a first fixed bed reactor through the first micro-mixer to be subjected to a dehydration condensation reaction; the mixture subjected to the dehydration condensation reaction is introduced into a second fixed bed reactor through a second micro-mixer for catalytic hydrogenation; the mixed material subjected to catalytic hydrogenation and a methanol solution of saturated hydrochloric acid are introduced into a micro-channel reactor through a third micro-mixer for a salt forming reaction, and vacuum concentration, pulping and purification are carried out to obtain secondary amine hydrochloride; and in the presence of acid, a dehydrating agent and an additive, the secondary amine hydrochloride and a glyoxal solution are subjected to Pictet-Spengler reaction and Friedel-Crafts hydroxyalkylation and dehydration cascade reaction, so as to obtain the 5, 8-dihydro-6H-isoquinoline [3, 2-alpha] isoquinoline compound.

Stereoselective Cycloaddition of Alkanesulfonyl Chlorides to Dihydroberberine

Novel berberine derivatives with annelated four-membered sulfone rings were synthesized. Cycloaddition of alkanesulfonyl chlorides to dihydroberberine occurred with high stereoselectivity and formed a single stereoisomer.