3090-70-8

Basic information

• Product Name: (3S,5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate
• Synonyms: (3S,5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate
• CAS NO: 3090-70-8
• Molecular Weight: 334.499
• Mol File: 3090-70-8.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: (3S,5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate(3090-70-8)
• EPA Substance Registry System: (3S,5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate(3090-70-8)

Safety Data

• Hazardous Substances Data: 3090-70-8(Hazardous Substances Data)

Usage

General Description

(3S,5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate is a chemical compound with a complex and lengthy name. It is an acetate derivative of a steroid compound, which means it contains a hydroxyl group and an acetate ester group. The presence of the cyclopenta[a]phenanthren structure indicates that it is a type of steroid hormone. (3S,5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate likely has physiological effects on the body due to its steroid nature, potentially influencing processes such as inflammation, immune response, and metabolism. The specific stereochemistry indicated by the (3S,5S,8R,9S,10S,13S,14S,17S) prefix suggests a highly specific three-dimensional arrangement of atoms in the molecule, which can influence its biological activity and function.

Upstream product

• 1639-43-6 androstenediol-3-acetate 
• 1239-31-2 3β-acetoxy-5α-androstan-17-one 
• 481-29-8 Epiandrosterone 
• 95043-80-4 Acetic acid (3S,8R,9S,10S,13S,14S)-10,13-dimethyl-17-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester 
• 95119-02-1 Acetic acid (3R,8R,9S,10S,13S,14S)-10,13-dimethyl-17-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester 
• 17291-39-3 p-toluenesulfonate of 3β-acetoxy-5α-androstan-17β-ol 
• 1098-12-0 3β-acetoxy-5α-androstan-17-one 
• 1600-76-6 3β-acetoxy-5α-androstan-17β-ol 
• 111712-88-0 3β-acetoxy-17β-methylsulfonyloxy-5α-androstane 
• 853-23-6 prasterone acetate 
• 104597-49-1 3-acetoxy-androst-5-en-17-one 
• 101033-92-5 3β-acetoxy-20-hydroximino-5α-pregn-16-en-20-one 
• 1169-20-6 3β-acetoxy-5α-pregn-16-en-20-one 
• 77-60-1 tigogenin 

Downstream Products

• 2722-91-0 17α-amino-5α-androstan-3β-ol 
• 1600-76-6 3β-acetoxy-5α-androstan-17α-ol 
• 61894-45-9 3β-acetoxy-17β-benzoyloxy-5α-androstane 
• 114552-86-2 17β-(toluene-4-sulfonyloxy)-5α-androstan-3β-ol 
• 571-20-0 5-androgen-3,17-diol 
• 17291-39-3 p-toluenesulfonate of 3β-acetoxy-5α-androstan-17β-ol 
• 17291-39-3 3β-acetoxy-17β-p-toluenesulfonyloxy-5α-androstan 

Relevant articles and documents

Steroid–Fullerene Hybrids from Epiandrosterone: Synthesis, Characterization and Theoretical Study

New hybrid fullerene–steroid derivatives were prepared by using the Bingel–Hirsch protocol, by treatment of [60]fullerene with malonates bearing the appropriate steroid moieties obtained, in turn, from the functionalization of epiandrosterone, an important naturally occurring steroid hormone. Monocycloadduct C60-steroid conjugates were obtained by functionalization of ring A or ring D of the steroid moiety. We have also described the multistep preparation of a [60]fullerene hybrid dumbbell endowed with two fullerene units connected through an epiandrosterone molecule by a cyclopropanation reaction. The new compounds have been spectroscopically characterized and their redox potentials, determined by cyclic voltammetry, reveal three reversible reduction waves for monocycloadducts (8, 9 and 11, 12), whereas dumbbell-type derivative 10 exhibits the best electron-accepting abilities of the Bingel-type fullerene–steroid series. Theoretical calculations at semiempirical (AM1) and single point B3LYP-D3/6-31G+(d,p) levels have predicted the most stable conformations for the hybrid compounds and allow explaining the observed regioselectivity in the cyclopropanation reaction with dimalonate 7 during the synthesis of the dumbbell derivative.

Silver-mediated oxidative aliphatic C-H trifluoromethylthiolation

The first example of a practical and direct trifluoromethylthiolation reaction of unactivated aliphatic C-H bonds employs a silver-based reagent. The reaction is operationally simple, scalable, and proceeds under aqueous conditions in air. Furthermore, its broad scope and good functional-group compatibility were demonstrated by applying this method to the selective trifluoromethylthiolation of natural products and natural-product derivatives.

Synthesis of 5α-androstan-3β,17β-diol from tigogenin

5α-Androstan-3β,17β-diol (3b-adiol), a known inhibitor of prostate cancer cell growth, was synthesized from tigogenin. Its structure was confirmed by NMR and IR spectroscopy and mass spectroscopy. Springer Science+Business Media, Inc. 2007.