Soyasapogenol B

Base Information

• Chemical Name: Soyasapogenol B
• CAS No.: 595-15-3
• Molecular Formula: C₃₀H₅₀O₃
• Molecular Weight: 458.725
• UNII: 1EZ10D7E2F
• DSSTox Substance ID: DTXSID10276153
• Nikkaji Number: J16.224H
• Wikidata: Q27108312
• Metabolomics Workbench ID: 53442
• ChEMBL ID: CHEMBL1762007
• Mol file: 595-15-3.mol

Synonyms:soyasapogenol B

Chemical Property of Soyasapogenol B

Chemical Property:

• Vapor Pressure: 1.18E-14mmHg at 25°C
• Melting Point: 258～259℃
• Boiling Point: 555.5°Cat760mmHg
• PKA: 14.91±0.70(Predicted)
• Flash Point: 226.6°C
• PSA: 60.69000
• Density: 1.1g/cm³
• LogP: 6.11210
• XLogP3: 7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 458.37599545
• Heavy Atom Count: 33
• Complexity: 848

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

SoyasapogenolB ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CC2C3=CCC4C5(CCC(C(C5CCC4(C3(CCC2(C(C1)O)C)C)C)(C)CO)O)C)C
• Isomeric SMILES: C[C@]12CC[C@@H]([C@]([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(CC[C@@]5([C@H]4CC(C[C@H]5O)(C)C)C)C)C)(C)CO)O
• Uses: Soyasapogenol B has been shown to attenuate lipopolysaccharide-induced memory impairment in mice.

Technology Process of Soyasapogenol B

There total 11 articles about Soyasapogenol B which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

soyasaponin I (51330-27-9) → D-Galactose (10257-28-0) + β-D-glucurono-6,3-lactone (18281-92-0) + L-rhamnose (73-34-7) + soyasapogenol B (124862-79-9,595-15-3)

Guidance literature:

With hydrogenchloride; In methanol; at 100 ℃; for 0.666667h;

DOI:10.1016/0031-9422(92)83294-9

Reference yield:

astragaloside VIII (55319-36-3,86361-64-0,119556-00-2) → soyasapogenol B (124862-79-9,595-15-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 mg / methanol; diethyl ether / 12 h

2: 15 mg / 2.) aq. 5 percent K₂CO₃ / methanol / 2 h / Irradiation

With potassium carbonate; In methanol; diethyl ether;

DOI:10.1248/cpb.31.716

Reference yield:

astragaloside VIII (55319-36-3,86361-64-0,119556-00-2) → methyl glucopyranosiduronic acid (4356-84-7,5155-45-3,5155-53-3,5241-02-1,5391-16-2,18486-39-0,46325-26-2,46325-27-3,73410-95-4,99094-38-9,134355-30-9,135414-77-6) + methyl xyloside (91-09-8,612-05-5,1825-00-9,2500-78-9,3867-83-2,3945-28-6,5328-63-2,6206-67-3,6207-01-8,6207-03-0,7404-24-2,17289-61-1,18449-76-8,33509-64-7,36793-06-3,41897-31-8,41897-32-9,41897-33-0,41897-34-1,41897-37-4,41897-38-5,41897-39-6,53448-52-5,65137-86-2,89615-04-3,89615-05-4,131233-91-5,14703-09-4) + methyl L-rhamnopyranoside (1128-40-1,1198-82-9,2592-55-4,5155-43-1,6340-52-9,10503-91-0,14009-07-5,14687-15-1,14917-55-6,15814-59-2,24332-98-7,34299-65-5,42214-00-6,42214-11-9,57783-34-3,57783-36-5,57783-38-7,57783-40-1,57783-42-3,58525-46-5,58525-47-6,58525-48-7,62182-01-8,62182-02-9,65310-00-1,65941-62-0,68069-80-7,71116-57-9,72274-54-5,72274-55-6,73036-22-3,83198-64-5,85505-15-3,102517-74-8,109718-80-1,109718-81-2,125280-09-3,129172-95-8,63864-94-8) + soyasapogenol B (124862-79-9,595-15-3)

Guidance literature:

With hydrogenchloride; methanol; for 2h; Heating;

DOI:10.1248/cpb.31.716

upstream raw materials:

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

soyasaponin I

Cloversaponin IV methyl ester

3-O-[β-D-glucopyranosyl(1->2)-β-D-glucuronopyranosyl]olean-12-en-3β,22β,24-triol

Downstream raw materials:

3,24-O-benzylidene soyasapogenol B

N-n-butyl-3β,22β-dibenzyloxyolean-12-ene-24-amide

sophoradiol

3β,22β-dibenzyloxyolean-12-ene

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