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

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

Used in Pharmaceutical Industry:
Yamogenin is used as a pharmaceutical compound for its antidiabetogenic properties, potentially aiding in the development of treatments for diabetes and related metabolic disorders. Its steroid framework also serves as a foundation 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.
Used in Antimicrobial Applications:
In the field of antimicrobial research, Yamogenin is utilized as a key component in the development of inhibitors for metallo-β-lactamase-1. This enzyme is associated with antibiotic resistance in gram-negative bacteria, and Yamogenin's potential to inhibit this enzyme could lead to the creation of novel treatments for antibiotic-resistant infections.

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

• 67-56-1 methanol 
• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 
• 125710-71-6 cyclopseudoyamogenin 
• 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 
• 54522-52-0 26-O-β-D-glucopyranosyl-22-O-methylfurost-5-ene-3β,26-diol 3-O-β-chacotrioside 
• 1180-12-7 Diosgeninmonoacetat 
• 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 

Downstream Products

• 6808-14-6 pseudodiosgenin 
• 4965-78-0 O-(toluene-4-sulfonyl)-yamogenin 
• 512-04-9 diosgenin 
• 151534-39-3 3-tert-butyldiphenylsilyldiosgenin 
• 1061-54-7 Diosgenin monoacetate 
• 1061-54-7 yamogenin-acetate 
• 13095-61-9 (25R)-cholest-5-ene-3β,26-diol 
• 113917-66-1 (25S)-3β,26-bis-p-nitrobenzoyloxycholest-5-en-16β-ol 
• 113917-67-2 (25S)-3,26-bis-p-nitrobenzoylcholest-5-en-16-one 
• 113917-68-3 C₄₇H₆₀F₆O₆ 
• 113917-68-3 C₄₇H₆₀F₆O₆ 
• 96481-07-1 (25S)-3β,26-dihydroxycholest-5-en-16-one 
• 113917-72-9 (25S)-3-acetoxy-26-tosyloxycholest-5-ene 
• 105078-98-6 (25S)-3β-acetoxy-26-trityloxycholest-5-ene 

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

OLIGOFURO- AND SPIRO-STANOSIDES OF ASPARAGUS ADSCENDENS

Two oligofurostanosides and two spirostanosides, isolated from a methanol extract of Asparagus adscendens (leaves), were characterized as 3-O-4)>6)-β-D-glucopyranosyl>-26-O--22α-methoxy-(25S)-furost-5-en-3β,26-diol (Adscendoside A), 3-O-4)>6)>-β-D-glucopyranosyl>-26-O--(25S)-furost-5-en-3β,22α,26-triol (Adscendoside B), 3-O-6)>-β-D-glucopyranosyl>-(25S)-spirostan-5-en-3β-ol (Adscendin A) and 3-O-4)>6)>-β-D-glucopyranosyl>-(25S)-spirostan-5-en-3β-ol (Adscendin B), respectively.Adscendin B and Adscendoside A are the artefacts of Ascendoside B formed through hydrolysis and methanol extraction respectively.Key Word Index - Asparagus adscendens; Liliaceae; saponins; oligofurostanosides; spirostanosides.

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.

Steroidal saponin from Polygonatum verticillatum

New steroidal glycoside 1 was isolated by fractionation of total extracted compounds from rhizomes of Polygonatum verticillatum (Convallariaceae). Chemical transformations, physical constants, and spectral data characterized its structure as (25S)-spirost

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.

New steroidal glycosides from Balanites aegyptiaca

Five new steroidal glycosides were isolated from the roots of Balanites aegyptiaca, a widely used African medicinal plant. On the basis of spectroscopic and chemical evidence, their structures were determined as (3β,12α,14β, 16β)-12-hydroxycholest-5-ene-3,16-diyl bis(β-D-glucopyranoside) (1), (3β,20S,22R,25R)- and (3β,20S,22R,25S)-26-(β-D-glucopyranosyloxy)-22-methoxyurost -5-en-3-yl βD-xylopyranosyl-(1 → 3)-β-D-glucopyranosyl-(1 → 4)[α-L-rhamnopyranosyl-(1 → 2)]-β-D-glucolpyranoside (2 and 3, resp.), and (3β,20S,22R,25S)- and (3β,20S,22R,25S)-spirost-5-en-3-yl 3β-D-xylopyranosyl-(1 → 3)-β-D-glucopyranosyl-(1→4)[α-L-rhamnopyranosyl-(1 → 2)]-β-D-glucopyranoside (4 and 5, resp.).

Spirostanols obtained by cyclization of pseudosaponin derivatives and comparison of anti-platelet agglutination activities of spirostanol glycosides

Naturally occurring saponins 3 and 4 have a normal type F ring and α- arranged CH3-21 group. Treatments of pseudosaponin peracetates 18 and 19 derived from 3 and 4, respectively, with alcoholic KOH, followed by acidification with acetic acid, gave spirostanols 20 and 22 having iso type F rings as major products. Structural analyses of sapogenins and saponins derived from pseudo derivatives 11, 12, 18 and 19 were performed by comparisons of their 1H-NMR spectral data and the X-ray analytical data of 3-O-p-bromobenzoyl sarsasapogenin 7, 3-O-acetyl diosgenin 13 and saponin 20. The mechanisms of ring-closure reaction of the side chain at C-22 of pseudosapogenins and pseudosaponins were deduced using stereomodels of the spirostanols derived from 11 under various reaction conditions. Inhibitory activities of saponin diglycosides 3, 4, 20, 21 and 25 on human platelet agglutinations induced by ADP and ristocetin were compared. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

Medicinal foodstuffs. VIII.1 Fenugreek seed. (2) : Structures of six new furostanol saponins, trigoneosides IVa, Va, Vb, VI, VIIb, and VIIIb, from the seeds of indian trigonella foenum-graecum L

Following the characterization of trigoneosides Ia, Ib, IIa, IIb; IIIa, and IIIb, seven new steroidal saponins called trigoneosides IVa, Va, Vb, VI, VIIb, VIIIb, and IX were isolated from a medicinal foodstuff fenugreek seed, the seeds of Trigonella foenum-graecum L. (Leguminosae) originating from India. The structures of trigoneosides IVa, Va, Vb, VI, VIIb, and VIIIb were elucidated on the basis of chemical and physicochemical evidence.

Spirostanol glycosides from Asparagus plumosus

Three spirostanol glycosides were isolated from a methanol extract of the leaves of Asparagus plumosus and characterized.

STEROID GLYCOSIDES OF THE SEEDS OF Solanum melongena. STRUCTURES OF MELONGOSIDES A, B, E, F, AND H

Three chromatographically individual fractions, each containing tigogenin glycosides and diosgenin glycosides have been isolated by chromatography on a silica gel column from a methanolic extract of eggplant seeds.To separate the mixture of two difficultly separable glycosides into individual components, each fraction was acetylated and epoxidated, and the derivatives obtained were separated chromatographically.The tigogenin glycoside peracetates isolated were saponified, and the diosgenin epoxide glycoside acetates were de-epoxidated and saponified, to give the individual glycosides, melongosides A, B, E, F, and H.The complete chemical structure of each melongoside has been shown with the aid of acid hydrolysis, methylation, and periodate oxidation followed by a study of the products obtained.