475-83-2 Usage
Description
Nuciferine is an aporphine alkaloid derived from Nelumbo lutea, which yields colorless crystals when crystallized from ethanol. It is laevorotatory, with specific rotations recorded at [α]22D -157.5° and -215°. The ultraviolet spectrum of nuciferine exhibits three absorption maxima at 230, 272, and 310 nm. The presence of two methoxyl groups and one methylimino group characterizes this alkaloid. Nuciferine can be identified as the hydrochloride, with a melting point of 241°C (in vacuo), and the methiodide, with a melting point of 177-8°C. The optically inactive base of nuciferine has been synthesized, with a melting point of 136-7°C, and its hydrochloride form appears as small colorless prisms from H2O, with a melting point of 258°C (dec.).
Uses
Used in Pharmaceutical Industry:
Nuciferine is used as a bioactive compound for its potential weight loss and lipid reduction effects. It can be employed in the development of pharmaceutical products aimed at managing obesity and related metabolic disorders.
Used in Research and Development:
Nuciferine serves as a valuable subject for content determination, identification, and pharmacological experiments. Its unique properties and alkaloid structure make it an interesting candidate for further research in understanding its therapeutic potential and possible applications in medicine.
Safety Profile
Poison by ingestion andintraperitoneal routes. When heated to decomposition itemits toxic fumes of NOx.
References
Gulland, Haworth., J. Chern. Soc., 590 (1928)Yunusov, Konovalova, Orekhov., Bull. Soc. Chim. Fr., 70 (1940)Arthur, Cheung., J. Chern. Soc., 2306 (1959)Kupchan et al., Tetrahedron, 19, 227 (1963)
Check Digit Verification of cas no
The CAS Registry Mumber 475-83-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,7 and 5 respectively; the second part has 2 digits, 8 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 475-83:
(5*4)+(4*7)+(3*5)+(2*8)+(1*3)=82
82 % 10 = 2
So 475-83-2 is a valid CAS Registry Number.
InChI:InChI=1/C19H21NO2/c1-20-9-8-13-11-16(21-2)19(22-3)18-14-7-5-4-6-12(14)10-15(20)17(13)18/h4-7,11,15H,8-10H2,1-3H3
475-83-2Relevant articles and documents
Stereoselective total synthesis of (S)- and (R)-nuciferine using benzyne chemistry
Casagrande, Gleison A.,Deflon, Victor M.,Martins, Gabriel R.,Oliveira-Silva, Diogo,Perecim, Givago P.,Pinto, Leandro M. C.,Raminelli, Cristiano
, (2020/08/13)
Total syntheses of (S)- and (R)-nuciferine were accomplished through approach involving diastereoselective reaction between a chiral dihydroisoquinoline enamide and 2-(trimethylsilyl)phenyl trifluoromethanesulfonate promoted by CsF, affording a separable mixture of diastereoisomers, which provided (S)- and (R)-nuciferine via simple and efficient transformations.
Aporphine alkaloid synthesis and diversification via direct arylation
Lafrance, Marc,Blaquiere, Nicole,Fagnou, Keith
, p. 811 - 825 (2008/02/12)
Palladium-catalyzed direct arylation of aryl chlorides, bromides and iodides has been applied to the preparation of new aporphine analogues including C2-substituted aporphines by reaction with benzodioxole, pyridine N-oxide and pyrazine N-oxide. Successful application of direct arylation in these diversification reactions highlights its utility not only in convergent, but also in divergent synthesis. We also describe enantioselective syntheses of (R)-nornuciferine and (R)-nuciferine employing a catalytic asymmetric transfer hydrogenation in high yield and excellent enantiomeric excess. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
