595-15-3

Basic information

• Product Name: SOYASAPOGENOL B(P)
• Synonyms: SOYASAPOGENOL B(P);(4S)-Olean-12-ene-3β,22β,24-triol;Sapogenol B;(3S,4S,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,9-diol;(3S,4S,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-4,6a,6b,8a,11,11,14b-heptamethyl-4-methylol-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,9-diol;Soyasapogel B;Soyasapogenol M2;Soyasapogenol B, 98%, from Glycine max (L.) Merr.
• CAS NO: 595-15-3
• Molecular Formula: C₃₀H₅₀O₃
• Molecular Weight: 458.722
• Product Categories: Sapogenins
• Mol File: 595-15-3.mol
• Article Data: 8

Chemical Properties

• Melting Point: 258～259℃
• Boiling Point: 555.5°Cat760mmHg
• Flash Point: 226.6°C
• Appearance: /
• Density: 1.1g/cm³
• Vapor Pressure: 1.18E-14mmHg at 25°C
• Refractive Index: 1.562
• PKA: 14.91±0.70(Predicted)
• CAS DataBase Reference: SOYASAPOGENOL B(P)(CAS DataBase Reference)
• NIST Chemistry Reference: SOYASAPOGENOL B(P)(595-15-3)
• EPA Substance Registry System: SOYASAPOGENOL B(P)(595-15-3)

Safety Data

• Hazardous Substances Data: 595-15-3(Hazardous Substances Data)

Usage

Uses

Soyasapogenol B has been shown to attenuate lipopolysaccharide-induced memory impairment in mice.

Definition

ChEBI: A pentacyclic triterpenoid that is oleanane containing a double bond between positions 12 and 13 and substituted by hydroxy groups at the 3beta, 22beta and 24-positions.

InChI:InChI=1/C30H50O3/c1-25(2)16-20-19-8-9-22-27(4)12-11-23(32)28(5,18-31)21(27)10-13-30(22,7)29(19,6)15-14-26(20,3)24(33)17-25/h8,20-24,31-33H,9-18H2,1-7H3/t20-,21+,22+,23-,24+,26+,27-,28+,29+,30+/m0/s1

Upstream product

• 67-56-1 methanol 
• 51330-27-9 soyasaponin I 
• 100201-60-3 sophoraflavoside I 
• 55319-36-3 astragaloside VIII 
• 82793-05-3 3-O-[α-L-rhamnopyranosyl(1->2)-β-D-glucopyranosyl(1->2)-β-D-glucuronopyranosyl]olean-12-en-3β,22β,24-triol 
• 82793-03-1 3-O-[β-D-glucopyranosyl(1->2)-β-D-glucuronopyranosyl]olean-12-en-3β,22β,24-triol 
• 143519-29-3 Cloversaponin IV methyl ester 
• 142750-17-2 3-O-α-L-rhamnopyranosyl(1->2)-β-D-xylopyranosyl(1->2)-6-O-methyl-β-D-glucuronopyranosyl-soyasapogenol B 22-O-β-D-glucopyranoside 
• 100201-62-5 prosapogenol 

Downstream Products

• 83689-13-8 (3S,4S,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-4,6a,6b,8a,11,11,14b-Heptamethyl-4-trityloxymethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picene-3,9-diol 
• 195155-81-8 N-n-butyl-3β,22β-dibenzyloxyolean-12-ene-24-amide 
• 6822-47-5 sophoradiol 
• 862248-29-1 3β,22β-dibenzyloxyolean-12-ene 
• 186415-73-6 ((3S,4S,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-3,9-Bis-benzyloxy-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picen-4-yl)-methanol 
• 186415-78-1 (3S,4S,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-9-Benzyloxy-4-benzyloxymethyl-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picen-3-ol 
• 187394-37-2 3β,22β-dibenzyloxy-24-methoxyolean-12-ene 
• 187394-40-7 22β,24-dibenzyloxy-3β-methoxyolean-12-ene 
• 186415-77-0 C₄₄H₆₀O₃ 
• 186415-74-7 (3S,4R,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-3,9-Bis-benzyloxy-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picene-4-carbaldehyde 
• 187393-82-4 (3S,4R,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-3,9-Bis-benzyloxy-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picene-4-carboxylic acid 
• 187394-34-9 24-acetoxy-3β,22β-dibenzyloxyolean-12-ene 
• 186415-79-2 (4R,4aR,6aS,6bR,8aR,9S,12aR,12bR,14bS)-4-Benzyloxy-9-benzyloxymethyl-2,2,4a,6a,6b,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,12,12a,12b,13,14b-octadecahydro-picene 
• 187394-39-4 Acetic acid (3S,4S,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-9-benzyloxy-4-benzyloxymethyl-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picen-3-yl ester 

Relevant articles and documents

Artefact formation during acid hydrolysis of saponins from Medicago spp.

Artefact compounds obtained during acid hydrolysis of saponins from Medicago spp. (Fabaceae), have been monitored and evaluated by GC-FID. Their identification has been performed by GC-MS and 1H and 13C NMR. Saponins with different substituents on the triterpenic pentacyclic aglycones were considered, and their hydrolysis products were detected and quantified during 10?h of time course reaction. From soyasapogenol B glycoside the well known soyasapogenols B, C, D and F were obtained together with a previously undescribed sapogenol artefact identified as 3β,22β,24-trihydroxyolean-18(19)-en and named soyasapogenol H. From a zanhic acid saponin two major artefact compounds identified as 2β,3β,16α-trihydroxyolean-13(18)-en-23,28-dioic acid and 2β,3β,16α-trihydroxyolean-28,13β-olide-23-oic acid were obtained, together with some zanhic acid. Other compounds, detected in very small amount in the reaction mixture, were also tentatively identified based on their GC-MS and UV spectra. The other most characteristic saponins in Medicago spp., hederagenin, bayogenin and medicagenic acid glycosides, under acidic condition of hydrolysis, released instead the correspondent aglycones and generated a negligible amount of artefacts. Nature of artefacts and mechanism of their formation, involving a stable tertiary carbocation, is here proposed and discussed for the first time.

Four new oleanene derivatives from the sseeds of Astragalus complanatus

Four new methyl ester derivatives of oleanene glycosides (3-6) were isolated from the seeds of Astragalus complanatus R. BR. together with two known triterpene glycosides, astragaloside VIII methyl ester (1) and soyasaponin I methyl ester (2) after treatment with diazomethane during separation procedure. The structures of 3-6 were elucidated as 3-O-α-L-rhamnopyranosyl(1→2)-β-D-xylopyranosyl(1→2)-6-O-methy-β-D- glucuronopyranosyl-soyasapogenol B 22-O-β-D-glucopyranoside, 3-O-α-L-rhamnopyranosyl(1 →2)-β-D-galactopyranosyl(1→2)-6-O-methyl-β-D-glucuronopyranosyl-soy asapogenol B 22-O-β-D-glucopyranoside, 3-O-α-L-rhamnopyranosyl(1→2)-β-D-xylopyranosyl(1→2)-6-O-methyl-β-D -glucuronopyranosyl 3β,22β,24-trihydroxy-11-oxo-olean-12-ene and 3-O-α-L-rhamnopyranosyl (1→2)-β-D-galactopyranosyl(1→2)-6-O-methyl-β-D-glucuronopyranosyl 3β,22β,24-trihydroxy-11-oxo-olean-12-ene, respectively.

Saponin and sapogenol. XL. Structure of sophoraflavoside I, a bisdesmoside of soyasapogenol B, from Sophorae radix, the root of Sophora flavescens Aiton

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