4947-75-5

Basic information

• Product Name: SMILAGENIN ACETATE
• Synonyms: SMILAGENIN ACETATE;25R,5BETA-SPIROSTAN-3BETA-OL 3-ACETATE;5-BETA, 20-ALPHA, 22-ALPHA, 25D-SPIROSTAN-3-BETA-OL ACETATE;Nsc15488
• CAS NO: 4947-75-5
• Molecular Formula: C₂₉H₄₆O₄
• Molecular Weight: 458.67
• Mol File: 4947-75-5.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 527.5°Cat760mmHg
• Flash Point: 221.8°C
• Appearance: /
• Density: 1.11g/cm³
• Vapor Pressure: 3.23E-11mmHg at 25°C
• Refractive Index: 1.539
• CAS DataBase Reference: SMILAGENIN ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: SMILAGENIN ACETATE(4947-75-5)
• EPA Substance Registry System: SMILAGENIN ACETATE(4947-75-5)

Safety Data

• Hazardous Substances Data: 4947-75-5(Hazardous Substances Data)

Usage

General Description

Smilagenin acetate is a naturally occurring chemical compound found in the Smilax species of plants, which are commonly known as greenbriers or sarsaparilla. It is a steroidal sapogenin, a type of steroid precursor that can be converted into various hormones and other biologically active compounds in the body. Smilagenin acetate has been studied for its potential therapeutic properties, including anti-inflammatory, antioxidant, and anticancer effects. It is also being investigated for its ability to modulate the immune system and improve overall health. Additionally, smilagenin acetate has been used in traditional medicine as a natural remedy for various ailments, although more research is needed to fully understand its benefits and potential applications.

InChI:InChI=1/C29H46O4/c1-17-8-13-29(31-16-17)18(2)26-25(33-29)15-24-22-7-6-20-14-21(32-19(3)30)9-11-27(20,4)23(22)10-12-28(24,26)5/h17-18,20-26H,6-16H2,1-5H3/t17-,18+,20-,21+,22-,23+,24+,25+,26+,27+,28+,29-/m1/s1

Upstream product

• 117019-62-2 (25R)-3β-hydroxy-5α14β-spirostan-11-one 
• 54965-96-7 (25R)-3β-hydroxy-5α,14β-spirost-8-en-11-one 
• 116949-76-9 (25R)-3β-acetoxy-5α,14β-spirost-8-en-11-one 
• 108-24-7 acetic anhydride 
• 77-60-1 3-epismilagenin 
• 512-07-2 (25R)-5β-spirostan-3-one 
• 126-18-1 smilagenin 
• 126-19-2 sarsasapogenin 
• 838087-02-8 (25S)-5β-furost-20(22)-ene-3β,26-diyl diacetate 
• 75-36-5 acetyl chloride 
• 92052-38-5 4-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl trichloracetimidate 
• 77-60-1 tigogenin 
• 74808-10-9 2,3,4,6-tetra-O-acetyl-d-glucopyranosyl trichloroacetimidate 
• 88908-42-3 C₂₉H₄₇IO₄ 

Downstream Products

• 2601-07-2 3β-acetoxy-5β-pregn-16-en-20-one 
• 5355-51-1 acetic acid-((23R,25R)-23-bromo-5β-spirostan-3β-yl ester) 
• 5380-57-4 acetic acid-((23S,25R)-23-bromo-5β-spirostan-3β-yl ester) 
• 469-00-1 sarsasapogeninoic acid 
• 16787-53-4 (25S)-3β-hydroxy-5β-spirostan-23-one 
• 289042-56-4 3-O-p-bromobenzoylsarsasapogenin 
• 511-92-2 (25S)-5β-Spirostan 
• 126-19-2 sarsasapogenin 
• 35319-92-7 (25S)-3β-acetoxy-5β-spirostan-23-one 
• 359416-36-7 3β-acetoxy-16β-hydroxy-5β-bisnorcholanoic acid 22->16 lactone 
• 914477-77-3 (23R,25S)-3β-acetoxy-16β,23:23,26-diepoxy-5β-cholestan-22-one 
• 1236306-02-7 (23R,25S)-23-phenylseleno-5β-spirostan-3β-ol acetate 
• 1380412-89-4 [23(23')E, 25S]-23(23')-benzylidene-5β-spirostan-3β-ol acetate 

Relevant articles and documents

Sarsasapogenin-structure-modified derivatives, pharmaceutical compositions thereof and applications of the compositions

The invention relates to sarsasapogenin-structure-modified derivatives. The derivatives are characterized in that the structure formulas of the derivatives are shown as (I) and (II); pharmaceutical compositions of the derivatives and applications thereof are also provided; and many of the newly synthesized compounds show activity superior to activity of lead compounds through activity testing aiming at AD related targets. The compositions have high practical value for treating senile dementia. Defects of sarsasapogenin-structure-modified derivatives in the prior art are made up. The derivatives and the compositions are of great significance.

Epimerization of C-22 in (25R)- and (25S)-sapogenins

Most of the naturally occurring steroidal sapogenins (C-23 non-substituted frameworks), possess an R configuration at the spiro C-22 center. Their C-22 epimers have become important targets in biological research. This paper describes a procedure to obtain 22S-spirostans from 22R-sapogenins and pseudosapogenin skeletons, without affecting the chirality at either C-25 or C-20. An optimal way to synthesize the pair of C-22 stereoisomers of 23-acetyldiosgenin is also reported. The latter was obtained from a 22,26-epoxycholestane or from 23-acetylfurostene compounds.

Steroidal sapogenins from rhizomes of Yucca gloriosa

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