68422-03-7

Basic information

• Product Name: 17-[1-(5-methylpiperidin-2-yl)ethyl]androst-5-ene-3,16-diol
• CAS NO: 68422-03-7
• Molecular Formula: C₂₇H₄₅NO₂
• Molecular Weight: 415.6517
• Mol File: 68422-03-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 544.2°C at 760 mmHg
• Flash Point: 59°C
• Density: 1.09g/cm³
• Vapor Pressure: 4.09E-14mmHg at 25°C
• Refractive Index: 1.563
• CAS DataBase Reference: 17-[1-(5-methylpiperidin-2-yl)ethyl]androst-5-ene-3,16-diol(CAS DataBase Reference)
• NIST Chemistry Reference: 17-[1-(5-methylpiperidin-2-yl)ethyl]androst-5-ene-3,16-diol(68422-03-7)
• EPA Substance Registry System: 17-[1-(5-methylpiperidin-2-yl)ethyl]androst-5-ene-3,16-diol(68422-03-7)

Safety Data

• Hazardous Substances Data: 68422-03-7(Hazardous Substances Data)

Usage

Chemical class

Androstane steroids

Derivative of

Testosterone

Role

Development and maintenance of male reproductive tissues

Structural feature

Methylpiperidine group attached to the steroid backbone

Receptor binding

Potential binding affinity to androgen receptors

Hydroxyl groups

Presence at the 3 and 16 positions in the steroid backbone

Metabolic and biological activity

Similar to natural androgens

Pharmaceutical or research applications

Not widely known

Androgenic properties

Potentially valuable for studying and manipulating hormonal signaling pathways in the human body

Upstream product

• 129939-91-9 (22S,25S)-N-Benzyloxycarbonyl-22,26-epimino-3β-hydroxycholest-5-en-16-one 
• 143235-56-7 (22R,25R)-3β,16β-diacetoxy-22,26-epiminocholest-5-ene 
• 126-17-0 solasodine 
• 991-62-8 (3b,25R)-3-hydroxyfurosta-5,20⁽²²⁾-dien-26-yl 4-Methylbenzenesulfonate 
• 514-32-9 C₂₇H₄₃NO₂ 
• 1000612-48-5 C₂₇H₄₁N₃O₂ 
• 30040-85-8 (25R)-22,26-epiminocholesta-5,22(N)-diene-3β,16β-diol diacetate 
• 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 
• 129850-53-9 (22S,25S)-N-Benzyloxycarbonyl-22,26-epiminocholest-5-ene-3β,16β-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 

Downstream Products

• 29271-49-6 Etioline 
• 65027-01-2 deacetylmuldamine 
• 65027-00-1 22-Isoteimine 
• 129938-50-7 (22R,25S)-N-Benzyloxycarbonyl-22,26-epiminocholest-5-ene-3β,16α-diol 
• 129850-54-0 (22R,25S)-N-Benzyloxycarbonyl-22,26-epimino-3β-hydroxycholest-5-en-16-one 

Relevant articles and documents

Synthesis and evaluation of in vitro anticancer activity of novel solasodine derivatives

Solasodine 11 is a steroidal alkaloid with various biological activities. Herein, 8 novel solasodine derivatives were synthesized and their effect on prostate cancer cell proliferation was assessed in vitro. Significant improvement in antiproliferative activity was achieved among some of the synthetic analogs. In particular, 19 exhibited the most potent inhibitory effect against the proliferation of PC-3 cell line (IC50=3.91μmol/L).

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).

Synthesis of the veratrum alkaloids verazin from tomatid-5-en-3-beta-ol

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