Tropinone Powder CAS 532-24-1

Product Introduction

About Tropinone powder:leaves reach maximal alkaloid content when the plant is budding and flowering, and roots are most poisonous in the end of the plant's vegetation period (Raetsch, 2005). Belladonna nectar is transformed by bees into honey that also contains tropane alkaloids (Hazlinsky, 1956). They are traditionally obtained by extraction from the leaves of cultured plants. An alternative to extraction from plant tissue could be the use of cell suspension cultures (Fuyita and Tabata, 1987).
Tropane is a bicyclic amine that has a pyrrolidine and a piperidine ring sharing a common nitrogen atom and two carbon atoms. It is the common structural element of all tropane alkaloids. All parts of the plant contain tropane alkaloids ("Committee for Veterinary Medicinal Products, A. belladonna, Summary Report". The European Agency for the Evaluation of Medicinal Products.
1998. Archived from the original on 2006-07-18. Retrieved 2008-07-08.) Roots have up to 1.3%, leaves 1.2%, stalks 0.65%, flowers 0.6%, ripe berries 0.7%, and seeds 0.4% tropane alkaloids; However, it has been shown that tropane alkaloid biosynthesis was correlated with root differentiation (Endo and Yamada, 1985). For this reason, hairy root formation offers an interesting approach to produce these secondary metabolites (Hamill et al., 1987; Verpoorte et al., 1999).

Tropane was synthesized from reduction of Tropinone powder by using ptO2in the presence of 2 N HCl(Scheme 10.4). The synthesis of tropinone done by Robinson was considered a classic in total synthesis (Birch, 1993) due to its simplicity and biomimetic approach. Tropinone powder is a bicyclic molecule, but the reactants used in its preparation are fairly simple: succinaldehyde, methylamine, and acetonedicarboxylic acid (or even acetone). The synthesis is a good example of a biomimetic reaction or biogenetic-type synthesis because biosynthesis makes use of the same building blocks. It also demonstrates a tandem reaction in a one-pot synthesis.

Tropinone powder Picture	Tropinone MF

Product Application

The mechanism of the reaction is:
1: Nucleophilic addition of primary amine to aldehyde, followed by dehydration to form imine;
2: Nucleophilic addition within the imine molecule to construct the first ring;
3: Intermolecular Mannich reaction between the enolate anion and the acetone dicarboxylate anion
4: Dehydration to form a new enolate anion and a new imine;
5: Intramolecular Mannich reaction to form the second ring;
6: Removal of two carboxyl groups to form Tropinone powder;

 

 

product key technologies

01.

Tropinone powder is a tropane alkaloid, usually in the form of needle-shaped crystals, used as an intermediate for the synthesis of atropine sulfate. It is an alkaloid molecule worth mentioning in the history of organic synthesis. It is prepared by heating cyclization of succinaldehyde with methylamine and acetone dicarboxylic acid under alkaline conditions.

02.

Recently, K. C. Nicolaou used an excess of 2-iodoacylbenzoic acid (IBX) reagent and a one-pot reaction to oxidize the alcohol (cycloheptanol) to a ketone while forming an α,β-unsaturated structure. Further addition of methylamine can directly generate tropinone and its analogues. The reaction process is shown in the figure.

Product Specification

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kindly note: Use Tropinone powder for research purposes only. All compounds have risks. Please consult your doctor and learn about available studies before use. In addition, the above description of the compound comes from online literature. If there is any infringement, please contact us to delete it.

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