2086-96-6

Basic information

• Product Name: (R)-(+)-Canadine
• Synonyms: (R)-(+)-Canadine;(R)-9,10-dimethoxy-6,8,13,13a-tetrahydro-5H-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinoline
• CAS NO: 2086-96-6
• Molecular Formula: C₂₀H₂₁NO₄
• Molecular Weight: 339.38504
• Product Categories: Aromatics, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 2086-96-6.mol
• Article Data: 13

Chemical Properties

• Melting Point: 132°
• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly, Heated)
• CAS DataBase Reference: (R)-(+)-Canadine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-Canadine(2086-96-6)
• EPA Substance Registry System: (R)-(+)-Canadine(2086-96-6)

Safety Data

• Hazardous Substances Data: 2086-96-6(Hazardous Substances Data)

Usage

Description

(R)-(+)-Canadine, a protoberberine alkaloid, is characterized by its central depressant action and adenylate cyclase inhibitor activity. It is a yellow solid with unique chemical properties that contribute to its various applications.

Uses

Used in Pharmaceutical Industry:
(R)-(+)-Canadine is used as a pharmaceutical compound for its central depressant action and adenylate cyclase inhibitor activity. These properties make it a potential candidate for the development of medications targeting conditions related to overexcitation or hyperactivity in the central nervous system.
Used in Research and Development:
In the field of research and development, (R)-(+)-canadine serves as a valuable compound for studying the effects of protoberberine alkaloids on adenylate cyclase and their potential applications in the treatment of various neurological and psychiatric disorders.
Used in Chemical Synthesis:
(R)-(+)-Canadine, due to its unique chemical structure, is used as a starting material or intermediate in the synthesis of other complex organic compounds, particularly those with potential applications in the pharmaceutical, agrochemical, and material science industries.
Used in Quality Control and Standardization:
As a reference compound, (R)-(+)-canadine is utilized in quality control and standardization processes to ensure the purity and potency of protoberberine alkaloids in various products, such as herbal medicines and dietary supplements.

Upstream product

• 29074-38-2 canadine 
• 1485-00-3 5-(2-nitrovinyl)benzo[1,3]dioxole 
• 1422431-13-7 6-(2-(2-(benzo[d][1,3]dioxol-5-yl)ethylamino)-2-oxoethyl)-2,3-dimethoxybenzyl acetate 
• 73168-77-1 N-<2-(3,4-methylenedioxyphenyl)ethyl>(3,4-dimethoxy-2-hydroxymethyl)-phenylacetamide 
• 120-57-0 piperonal 
• 4697-59-0 7,8-dimethoxyisochroman-3-one 
• 56201-87-7 8-hydroxy-7-methoxyisobenzofuranyltetrahydropyran-3-one 
• 1131-94-8 homoisovanillic acid 
• 19626-36-9 methyl 2-(3-bromo-4-methoxyphenyl)acetate 
• 34918-57-5 methyl 3-bromo-4-hydroxyphenylacetate 
• 14199-15-6 Methyl 4-hydroxyphenylacetate 
• 1429118-75-1 C₂₀H₂₃NO₅ 
• 1484-85-1 3,4-methylenedioxyphenylethylamine 
• 633-65-8 berberine chloride 

Downstream Products

• 483-15-8 7,8-dihydroberberine 
• 4263-84-7 berberine iodide 
• 117-74-8 berberine hydroxide 
• 47474-49-7 cis-N-Methylcanadine 
• 6880-91-7 12,13-dihydrochelerythrine 
• 485-91-6 allocryptopine 

Relevant articles and documents

Formation and conformation of baicalin-berberine and wogonoside-berberine complexes

It is well-known that baicalin-berberine complex (1) precipitates in the water decoction of numerous Chinese Medicinal formulae containing Radix Scutellariae and Rhizoma Coptidis or Cortex Phellodendri. In the current study, ionic interaction between the carboxylate ion of baicalin and the quaternary ammonium ion of berberine was revealed to be responsible for the formation of 1 and wogonoside-berberine (2) by using FAB-MS and NMR titration experiments. In addition, nuclear Overhauser effect spectroscopy (NOESY) correlations observed in 1 and 2 suggested quite different conformation of the two complexes, which was further supported by the fact that the [a]D of the canadine obtained by reduction of 1 is of an opposite sign to that obtained from 2. Partition coefficients (n-octanol/water) determination demonstrated 12-20 times larger partition coefficient of each complex (1, 2) than that of each single compound (baicalin, wogonoside, and berberine), indicating the significant role of the formation of the complex in the bioavailability enhancement of these pharmacologically active constituents.

Preparation and structural elucidation of (-)-tetrahydroberberine-(+)-2,3-di(p-toluyl) tartaric acid complex

A new (2:1) complex of (-)-13aS-tetrahydroberberine [(-)-13aS-THB] with (+)-2,3-di(p-toluyl) tartaric acid (DTTA), i.e. 5,8,13,13a-tetrahydro-9,10-dimethoxy-2,3-methylenedioxy-6H dibenzo[a,g] quinolizine·2,3-di(p-toluyl) tartaric acid [2C20H20NO4·C20H18O8], as well as its optical active component (-)-THB, has been obtained from the resolution process of (±)-THB in methanol. The structures of this complex and an enantiomer (-)-13aS-THB have been characterized by CD, IR and NMR spectroscopy as well as by X-ray single crystal diffraction.

Method for synthesizing tetrahydroberberine and derivatives thereof

The invention provides a method for synthesizing tetrahydroberberine and derivatives thereof. Specifically, in the presence of an iridium metal catalyst precursor, a chiral diphosphine ligand, an acid and a halogen-containing additive, in a hydrogen atmosphere, a compound (II) is subjected to an asymmetric catalytic hydrogenation reaction in an organic solvent so as to prepare the compound (I).

Compositions and methods for producing benzylisoquinoline alkaloids

The present invention relates to host cells that produce compounds that are characterized as benzylisoquinolines, as well as select precursors and intermediates thereof. The host cells comprise one, two or more heterologous coding sequences wherein each of the heterologous coding sequences encodes an enzyme involved in the metabolic pathway of a benzylisoquinoline, or its precursors or intermediates from a starting compound. The invention also relates to methods of producing the benzylisoquinoline, as well as select precursors and intermediates thereof by culturing the host cells under culture conditions that promote expression of the enzymes that produce the benzylisoquinoline or precursors or intermediates thereof.