475-83-2 Usage
Uses
The lotus leaf alkaloid has the effect of weight loss and lipid reduction, and can be used for content determination/identification/pharmacological experiments.
Description
Nuciferine is an aporphine alkaloid from Nelumbo lutea, the ba~e yields colourless crystals
when crystallized from EtOH. It is laevorotatory, the following specific rotations
having been recorded; [α] 22D- 157.5° and - 215°. The ultraviolet spectrum has
three absorption maxima at 230, 272 and 310 mp. Two methoxyl groups and
one methylimino group are present and the alkaloid may be characterized as the
hydrochloride, m.p. 241°C (in vacuo) and the methiodide, m.p. 177-8°C. The
optically inactive base has been synthesized and has m.p. 136-7°C, giving a
hydrochloride in the form of small colourless prisms from H20, m.p. 258°C
(dec.).
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.
