512-06-1

Basic information

• Product Name: (20α,22R,25S)-Spirosta-5-ene-3β-ol
• Synonyms: (20α,22R,25S)-Spirosta-5-ene-3β-ol;(25S)-Spirost-5-en-3β-ol;Yamogenin;Diosgenin;Nsc 226132;Spirost-5-en-3-ol, (3beta,25S)-;Neodiosgenin
• CAS NO: 512-06-1
• Molecular Formula: C27H42O3
• Molecular Weight: 414.626
• EINECS: 208-134-3
• Product Categories: Herb extract
• Mol File: 512-06-1.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 527.1oC at 760 mmHg
• Flash Point: 272.6oC
• Appearance: White Solid
• Density: 1.13g/cm3
• Vapor Pressure: 2.59E-13mmHg at 25°C
• Refractive Index: 1.564
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Sparingly), Ethyl Acetate (Slightly), Methanol (Slightly), Pyridine
• CAS DataBase Reference: (20α,22R,25S)-Spirosta-5-ene-3β-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (20α,22R,25S)-Spirosta-5-ene-3β-ol(512-06-1)
• EPA Substance Registry System: (20α,22R,25S)-Spirosta-5-ene-3β-ol(512-06-1)

Safety Data

• Hazardous Substances Data: 512-06-1(Hazardous Substances Data)

Usage

Uses

Yamogenin is a sapogenin compound found in the plant amber fenugreek, with steroid framework, that maintains antidiabetogenic activity. They also provide framework for the synthesis of a potential inhibitor of metallo-β-lactamase-1 which is a major target in the treatment of diseases involving gram-negative bacteria.

InChI:InChI=1/C27H42O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h5,16-17,19-24,28H,6-15H2,1-4H3/t16-,17-,19-,20+,21-,22-,23-,24-,25-,26-,27+/m0/s1

Upstream product

• 1180-12-7 Diosgeninmonoacetat 
• 54522-52-0 26-O-β-D-glucopyranosyl-22-O-methylfurost-5-ene-3β,26-diol 3-O-β-chacotrioside 
• 91327-42-3 (25S)-spirost-5-en-3β-yl O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside 
• 94805-85-3 melongoside F 
• 89203-43-0 melongoside H 
• 91574-93-5 afromontoside 
• 65604-83-3 C₅₂H₈₆O₁₆ 
• 65604-80-0 mixture of 3-O-<α-L-rhamnopyranosyl-(1->2)><β-D-xylopyranosyl(1->3)>-β-D-glucopyranosides of diosgenin and yamogenin 
• 290809-76-6 (25S)-26-[(β-D-glucopyranosyl)oxy]-22α-methoxyfurost-5-en-3β-yl O-α-L-rhamnopyranosyl-(1->2)-O-[O-β-D-glucopyranosyl-(1->4)-α-L-rhamnopyranosyl-(1->3)]-β-D-glucopyranoside 
• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 
• 125710-71-6 cyclopseudoyamogenin 
• 67-56-1 methanol 

Downstream Products

• 6808-14-6 pseudodiosgenin 
• 4965-78-0 O-(toluene-4-sulfonyl)-yamogenin 
• 512-04-9 diosgenin 
• 151534-39-3 3-tert-butyldiphenylsilyldiosgenin 
• 6870-79-7 (25R)-spirost-4-ene-3-one 
• 2137-22-6 (20S,22S,25R)-spirosol-1,4-dien-3-one 
• 13095-61-9 (25R)-cholest-5-ene-3β,26-diol 
• 77-60-1 Neotigogenin 
• 105078-98-6 (25S)-3β-acetoxy-26-trityloxycholest-5-ene 
• 113917-72-9 (25S)-3-acetoxy-26-tosyloxycholest-5-ene 
• 96481-07-1 (25S)-3β,26-dihydroxycholest-5-en-16-one 
• 113917-68-3 C₄₇H₆₀F₆O₆ 

Relevant articles and documents

Spirostanol saponins from the rhizomes of Tacca chantrieri and their cytotoxic activity.

The rhizomes of Tacca chantrieri have been analysed for steroidal saponin constituents, resulting in the isolation of four new spirostanol saponins (1-4), along with one known saponin (5); their structures were elucidated on the basis of extensive spectro

Steroidal and pregnane glycosides from the rhizomes of Tacca chantrieri

The rhizomes of Tacca chantrieri have been analyzed as part of a systematic study on saponin constituents of medicinal plants. This has resulted in the isolation of three new bisdesmosidic furostanol saponins (1-3), two new bisdesmosidic pseudofurostanol saponins (4, 5), and two new pregnane glycosides (6, 7). Their structures were determined on the basis of extensive spectroscopic studies and a few chemical transformations.

Mild and selective deprotection method of acetylated steroids and diterpenes by dibutyltin oxide

Dibutyltin oxide (DBTO) was first utilized for the deacetylation of steroid and diterpene esters. The results showed the deprotection of acetylated steroids and diterpenes separately with moderate catalysis dibutyltin oxide in methanol selectively removed part acetyl groups of these substrates, whereas several functional groups of the steroids and diterpenes were retained and neither isomerization nor degradation of these substrates was observed. It seems that the acetyl groups with lower steric hindrance or near carbonyl, alkoxy, or hydroxyl groups can be cleaved by the reaction, whereas the acetyl groups with higher steric hindrance or without carbonyl, alkoxy, or hydroxyl groups neighboring were retained under the same conditions. One of the interesting results obtained was the selective hydrolysis of the 3β-O-acetyl group in the presence of the 6β group in 3β,6β-Di-O-acetyl-5α-hydroxypregn-16-en-20-one. This allows for subsequent introduction of one unit at C-3 and the other unit at C-6. This procedure is useful for the synthesis of a series of closely related isomers of 3β,5α,6β-trihydroxypregn-16-en-20-one and other widespread polyhydroxysteroids in marine organisms and some terrestrial species.