474-08-8

Usage

Uses

Used in Agricultural Industry:
Demissidine is used as a fungicide for controlling a wide range of fungal diseases in crops, thereby protecting plants and improving agricultural yields.
Used in Pharmaceutical Industry:
Demissidine is used as an active pharmaceutical ingredient in the development of antifungal medications, targeting various fungal infections in humans and animals.
Used in Laboratory Research:
Demissidine serves as a valuable research tool in laboratories, aiding scientists in studying fungal biology, pathogenesis, and the development of new antifungal agents.
Used in Environmental Control:
Demissidine is employed in environmental control applications to manage fungal growth in various settings, such as in soil, water systems, and industrial processes, to prevent contamination and maintain ecosystem balance.

InChI:InChI=1/C27H45NO/c1-16-5-8-23-17(2)25-24(28(23)15-16)14-22-20-7-6-18-13-19(29)9-11-26(18,3)21(20)10-12-27(22,25)4/h16-25,29H,5-15H2,1-4H3

Upstream product

• 80-78-4 solanidine 
• 4847-18-1 Δ⁴-Solaniden-3-one 
• 1449-16-7 16,28-seco-5α-solanidane-3β,16β-diol 
• 107297-20-1 5α,22αH,25βH-solanidan-3-one 
• 77-59-8 tomatidine 
• 1430077-87-4 (3S,16R)-3-(tert-butyldiphenylsilyloxy)-16-((tert-butyldimethylsilyl)oxy)isoandrosterone 
• 1430077-91-0 C₄₅H₆₈N₂O₅Si₂ 
• 1430077-95-4 C₃₉H₅₂O₄Si 
• 109152-46-7 (+)-(S)-3-methylpiperidine-(+)-mandelate 
• 1430077-85-2 (3S,16R)-3-(tert-butyldiphenylsilyloxy)-16-hydroxyisoandrosterone 
• 1430078-02-6 (2R,5S)-1-(tert-butoxycarbonyl)-5-methylpiperidine-2-carboxylic acid 
• 1430078-06-0 (2R,5S)-2-carboxy-5-methylpiperidin-1-ium 2,2,2-trifluoroacetate 
• 1430078-05-9 (2R,5S)-5-methylpiperidine-2-carboxylic acid 
• 1430078-13-9 (2R,5S)-trimethylsilyl 5-methylpiperidine-2-carboxylate 

Relevant academic research and scientific papers

Synthesis of Demissidine and Solanidine

Demissidine and solanidine, two steroidal alkaloids, are synthesized in eight steps from tigogenin acetate and diosgenin acetate, respectively, which involve the replacement of three C-O bonds with C-N bonds. Key transformations include a cascade ring-switching process of furostan-26-acid, an epimerization of C25, an intramolecular Schmidt reaction, and an imine reduction/intramolecular aminolysis process.

Synthesis of demissidine by a ring fragmentation 1,3-dipolar cycloaddition approach

A synthesis of the steroidal alkaloid demissidine from epiandrosterone is reported. A ring fragmentation reaction that efficiently ruptured the D-ring of a diazo ester derivative of epiandrosterone to provide an aldehyde tethered ynoate product was key to this sequence. Incorporation of the indolizidine framework was achieved by an azomethine ylide 1,3-dipolar cycloaddition.

Confirmation of Structure of Isosolacapine: Stereochemistry at Ring Juncture of Indolizidine Moiety of 22βH Solanidanes by 13C and 1H NMR Spectroscopy

Isosolacapine, a minor steroidal alkaloid of Solanum pseudocapsicum, earlier assigned structure 3, possesses a novel 22β N stereochemistry in a 22,26-epiminocholestane skeleton.This alkaloid has now been isolated from Solanum capsicastrum and its structure confirmed by its conversion to solanogantamine (8), a 22αH solanidane derivative ex Solanum giganteum.The ring-juncture stereochemistry of the indolizidine moiety of 22β H solanidanes, in general, has been elucidated on 13C and 1H NMR spectral evidences.