29271-49-6

Usage

Uses

Used in Pharmaceutical Industry:
16,28-Secosolanida-5,22(28)-diene-3β,16α-diol is used as a pharmaceutical compound for its potential therapeutic applications. 16,28-Secosolanida-5,22(28)-diene-3β,16α-diol's unique structure and properties make it a promising candidate for the development of new drugs targeting various health conditions.
Used in Chemical Research:
In the field of chemical research, 16,28-Secosolanida-5,22(28)-diene-3β,16α-diol serves as a valuable subject for studying the properties and behavior of cholestanol type alkaloids. This can lead to a better understanding of their interactions with biological systems and the development of novel applications in medicine and other industries.
Used in Plant Biology:
16,28-Secosolanida-5,22(28)-diene-3β,16α-diol is also used in plant biology to study the metabolic pathways and biosynthesis of alkaloids in plants like Veratrum album subsp. lobelianum. This knowledge can be applied to improve the cultivation and production of these plants for various purposes, including their use in traditional medicine and the development of new pharmaceutical compounds.
Used in Toxicology Studies:
Due to its presence in Veratrum album subsp. lobelianum, a plant known for its toxic properties, 16,28-Secosolanida-5,22(28)-diene-3β,16α-diol is used in toxicology studies to investigate its potential toxic effects and mechanisms of action. This research can contribute to the development of antidotes and safer handling practices for plants containing this alkaloid.

References

Khashmirov, Shakirov, Yunusov., Khim. Prir. Soedin, 6,339 (1970) Khashmirov, Shakirov, Yunusov., ibid, 7,779 (1971)

InChI:InChI=1/C27H43NO2/c1-16-5-8-23(28-15-16)17(2)25-24(30)14-22-20-7-6-18-13-19(29)9-11-26(18,3)21(20)10-12-27(22,25)4/h6,16-17,19-22,24-25,29-30H,5,7-15H2,1-4H3/t16-,17+,19-,20+,21-,22-,24+,25?,26-,27-/m0/s1

Upstream product

• 546-40-7 (25S)-3β-hydroxy-22βN-spirosol-5-ene 
• 129850-54-0 (22R,25S)-N-Benzyloxycarbonyl-22,26-epimino-3β-hydroxycholest-5-en-16-one 
• 129938-50-7 (22R,25S)-N-Benzyloxycarbonyl-22,26-epiminocholest-5-ene-3β,16α-diol 
• 4847-09-0 (3S,8S,9S,10R,13S,14S,17R)-17-[(S)-1-((2S,5S)-1-Chloro-5-methyl-piperidin-2-yl)-ethyl]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,16-diol 
• 35410-24-3 (22R,25S)-22,26-Epiminocholest-5-ene-3β,16β-diol 
• 65027-00-1 22-Isoteimine 
• 1176-36-9 (3S,8S,9S,10R,13S,14S,17R)-10,13-Dimethyl-17-[(S)-1-((2S,5S)-5-methyl-piperidin-2-yl)-ethyl]-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,16-diol 
• 129938-52-9 (22R,25S)-N-Chloro-22,26-epiminocholest-5-ene-3β,16α-diol 

Relevant academic research and scientific papers

Partial Synthesis of the Steroid Alkaloids Teinemine, 22-Isoteinemine, Etioline, and 25-Isoetioline

The rare 16α-hydroxylated steroid alkaloids teinemine , 22-isoteinemine , etioline , and 25-isoetioline are synthesized from the abundant spirosolane alkaloids tomatid-5-en-3β-ol and solasodine , respectively.The crucial stages of these syntheses are the conversion of 1 or 15 into the N-protected (22S,25S)-, (22R,25S)-, and (22S,25R) -22,26-epimino-3β-hydroxycholest-5-en-16-ones 6, 7, and 18 as well as their reductions with sodium/2-propanol to the 16α-hydroxy compounds teinemine (8), 22-isoteinemine (10), and (22S,25R)-22,26-epiminocholest-5-ene-3β,16α-diol (19), respectively.By treatment with sodium methanolate the N-chloro derivatives 9 and 11 of 8 and 10 afford etioline (12).In an analogous manner, the N-chloro derivative 20 of 19 is converted into 25-isoetioline (21).