17388-19-1

Basic information

• Product Name: 10-Methoxy-5,6-dihydrobenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium-9-ol
• Synonyms: 10-Methoxy-5,6-dihydrobenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium-9-ol;5,6-Dihydro-2,3-(methylenedioxy)-9-hydroxy-10-methoxydibenzo[a,g]quinolizinium;5,6-Dihydro-9-hydroxy-10-methoxybenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium;9-Berberoline;Berberrubin
• CAS NO: 17388-19-1
• Molecular Formula: C₁₉H₁₆NO₄
• Molecular Weight: 0
• Mol File: 17388-19-1.mol
• Article Data: 16

Chemical Properties

• Melting Point: 255-259 °C
• Appearance: /
• CAS DataBase Reference: 10-Methoxy-5,6-dihydrobenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium-9-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 10-Methoxy-5,6-dihydrobenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium-9-ol(17388-19-1)
• EPA Substance Registry System: 10-Methoxy-5,6-dihydrobenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium-9-ol(17388-19-1)

Safety Data

• Hazardous Substances Data: 17388-19-1(Hazardous Substances Data)

Usage

Chemical structure

A quinolizinium derivative with a methoxy group at the 10th position.

Molecular weight

Approximately 357.38 g/mol (calculated from the molecular formula)

Functional groups

Quinolizinium core, methoxy group, benzodioxole ring, and hydroxyl group.

Potential applications

Pharmaceutical and medicinal properties, including possible use in the treatment of neurological disorders or as an analgesic agent.

Research status

Further research and testing are needed to fully understand the potential uses and effects of this chemical compound.

Solubility

Unknown, but may be influenced by the presence of polar functional groups (methoxy and hydroxyl groups).

Stability

Unknown, but the presence of multiple aromatic rings and heteroatoms may contribute to its stability.

Reactivity

Unknown, but the compound may undergo reactions typical of its functional groups, such as nucleophilic substitution or electrophilic aromatic substitution.

Synthesis

The synthesis of this compound is not described in the provided material, but it likely involves the formation of the quinolizinium core, followed by the introduction of the methoxy and hydroxyl groups, and the benzodioxole ring.

InChI:InChI=1/C19H15NO4/c1-22-16-3-2-11-6-15-13-8-18-17(23-10-24-18)7-12(13)4-5-20(15)9-14(11)19(16)21/h2-3,6-9H,4-5,10H2,1H3/p+1

Upstream product

• 880344-86-5 2-[(2-benzo[1,3]dioxol-5-yl-ethylamino)-methyl]-6-methoxy-phenol 
• 131543-46-9 Glyoxal 
• 633-65-8 berberine chloride 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 1484-85-1 3,4-methylenedioxyphenylethylamine 
• 880344-81-0 2-{[(E)-2-Benzo[1,3]dioxol-5-yl-ethylimino]-methyl}-6-methoxy-phenol 
• 2086-83-1 berberine 

Downstream Products

• 15401-69-1 berberrubine chloride 

Relevant articles and documents

Berberrubine attenuates mucosal lesions and inflammation in dextran sodium sulfate-induced colitis in mice

Ulcerative colitis (UC) is a chronic relapsing disease without satisfactory treatments, in which intestinal inflammation and disrupted intestinal epithelial barrier are two main pathogeneses triggering UC. Berberrubine (BB) is deemed as one of the major active metabolite of berberine (BBR), a naturally-occurring isoquinoline alkaloid with appreciable anti-UC effect. This study aimed to comparatively investigate the therapeutic effects of BB and BBR on dextran sodium sulfate (DSS)-induced mouse colitis model, and explore the potential underlying mechanism. Results revealed that BB (20 mg/kg) produced a comparable therapeutic effect as BBR (50 mg/kg) and positive control sulfasalazine (200 mg/kg) by significantly reducing the disease activity index (DAI) with prolonged colon length and increased bodyweight as compared with the DSS group. BB treatment was shown to significantly ameliorate the DSS-induced colonic pathological alternations and decreased histological scores. In addition, BB markedly attenuated colonic inflammation by alleviating inflammatory cell infiltration and inhibiting myeloperoxidase (MPO) and cytokines (TNF-α, IFN-γ, IL-1β, IL-6, IL-4 and IL-10) productions in DSS mice. Furthermore, BB treatment substantially upregulated the expression of tight junction (TJ) proteins (zonula occludens-1, zonula occludens-2, claudin-1, occludin) and mRNA expression of mucins (mucin-1 and mucin-2), and decreased the Bax/Bcl-2 ratio. In summary, BB exerted similar effect to its analogue BBR and positive control in attenuating DSS-induced UC with much lower dosage and similar mechanism. The protective effect observed may be intimately associated with maintaining the integrity of the intestinal mucosal barrier and mitigating intestinal inflammation, which were mediated at least partially, via favorable modulation of TJ proteins and mucins and inhibition of inflammatory mediators productions in the colonic tissue. This is the first report to demonstrate that BB possesses pronounced anti-UC effect similar to BBR and sulfasalazine with much smaller dosage. BB might have the potential to be further developed into a promising therapeutic option in the treatment of UC.

The design and synthesis of a novel compound of berberine and baicalein that inhibits the efficacy of lipid accumulation in 3T3-L1 adipocytes

The combination of berberine and baicalein may have a better therapeutic effect against disease. To explore the combined effect of baicalein and berberine in the treatment of obesity, we designed and synthesized a hybrid compound, and its biological activities were evaluated in 3T3-L1 adipocytes. The structures of the berberine-baicalein (BBS) compounds were confirmed by 1H NMR, 13C NMR, ultraviolet spectroscopy and high resolution mass spectrometry (HRMS). The present study showed that the IC50 values of the inhibitory effects of baicalein, berberine and BBS against 3T3-L1 cells were 29.81 ± 0.90, 21.84 ± 1.67 and 9.42 ± 0.60 μM, respectively. The expression of mRNAs related to lipolysis and lipogenesis were examined by quantitative real-time PCR. The results showed that BBS could up-regulate the expression of the Atgl gene and down-regulate the mRNA expression of Srebp-1c, Fasn, Scd1, and Acc in 3T3-L1 adipocytes. These results indicate that BBS may have a stronger effect than baicalein and berberine on the viability of 3T3-L1 preadipocytes. In addition, BBS may have therapeutic effects and pharmacological activities against obesity. This “medicine couple” may be beneficial for studies of traditional Chinese medicine.

Method for synthesizing benzophenanthridine and protoberberine alkaloids through modular diversity regulation and control

The invention discloses a method for synthesizing benzophenanthridine and protoberberine alkaloids through modular diversity regulation and control. The method comprises the following steps: improving a substituent group of a high-iodine salt leaving group, generating pyridine alkyne under the action of relatively mild potassium tert-butoxide, and carrying out [4 + 2] cycloaddition reaction on the pyridine alkyne and diene to obtain polysubstituted isoquinoline ring precursor compounds. Ring opening and aromatization of the isoquinoline ring precursor are realized by developing a novel iridium-catalyzed cross-coupling method, polysubstituted isoquinoline ring compounds with connecting capacity are efficiently synthesized, and then the polysubstituted isoquinoline ring compounds are coupled with a high-activity polysubstituted cyclic boric acid to obtain 3-aryl isoquinoline high-grade intermediates. Through application of two different chemical principles, regulation and control of the 3-aryl isoquinoline high-grade intermediates are realized, and benzophenanthridine and protoberberine alkaloids are modularly, diversely and efficiently synthesized.

A protoberberine alkaloid based ratiometric pH-responsive probe for the detection of diabetic ketoacidosis

Herein we report a ratiometric naturally occurring fluorescent pH probe, berberrubine (BBn) for the direct detection of diabetic ketoacidosis (DKA) conditions of patients having type I diabetes mellitus. The photophysical properties of the probe during pH titrations showed remarkable changes in absorption spectra where two absorption bands at 377 and 326 nm have disappeared followed by the emergence of an absorption maxima at 346 nm in highly acidic conditions. In addition, a fluorescence enhancement effect was observed in the alkaline pH, with a bathochromic shift of 33 nm. Moreover, the solution switches the color from light yellow to light pink with the change of pH from acidic to basic. A pKa value of 7.57 and a good linearity between pH 5.0–9.0 indicate that the probe can be used efficiently for the DKA condition, where pH variations are in the range of 6–7. The excellent water solubility, photostability, reversibility, and selectivity of BBn make it a potential pH sensing agent for acidic microenvironments. The reversible sensing of pH variations during DKA could be effective in primary detection and diagnosis which can assist in avoiding further complications of acidosis.