Bayogenin

Base Information

• Chemical Name: Bayogenin
• CAS No.: 6989-24-8
• Molecular Formula: C₃₀H₄₈O₅
• Molecular Weight: 488.708
• ChEMBL ID: CHEMBL1797308
• DSSTox Substance ID: DTXSID30861949
• Metabolomics Workbench ID: 28746
• Nikkaji Number: J13.338H
• Wikidata: Q27122087
• Mol file: 6989-24-8.mol

Synonyms:bayogenin;6989-24-8;2beta,23-dihydroxyoleanolic acid;CHEMBL1797308;CHEBI:50481;2beta,3beta,23-trihydroxyolean-12-en-28-oic acid;(2beta,3beta,4alpha)-2,3,23-trihydroxyolean-12-en-28-oic acid;(4aS,6aR,6aS,6bR,8aR,9R,10R,11S,12aR,14bS)-10,11-dihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid;SCHEMBL1048748;DTXSID30861949;HY-N1932;2,3,23-Trihydroxyolean-12-en-28-oic acid (2beta,3beta,4alpha)-;BDBM50346623;MFCD09954365;AKOS037514561;Olean-12-en-28-oic acid, 2,3,23-trihydroxy-, (2beta,3beta,4alpha)-;LMPR0106150007;AC-34021;MS-29091;CS-0018244;NS00093730;Q-100781;Q27122087

Chemical Property of Bayogenin

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: >300 °C (decomp)
• Boiling Point: 605.956oC at 760 mmHg
• PKA: 4.62±0.70(Predicted)
• Flash Point: 334.295oC
• PSA: 97.99000
• Density: 1.192g/cm3
• LogP: 5.17680
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Pyridine (Slightly, Sonicated)
• XLogP3: 5.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 488.35017463
• Heavy Atom Count: 35
• Complexity: 941

Purity/Quality:

99% ^*data from raw suppliers

Bayogenin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CC(C(C5(C)CO)O)O)C)C)C2C1)C)C(=O)O)C
• Isomeric SMILES: C[C@@]12CC[C@@H]3[C@@]([C@H]1CC=C4[C@]2(CC[C@@]5([C@H]4CC(CC5)(C)C)C(=O)O)C)(C[C@@H]([C@@H]([C@@]3(C)CO)O)O)C

Technology Process of Bayogenin

There total 55 articles about Bayogenin 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: 71.7%

bayogenin {28-O-α-L-rhamnopyranosyl-(1->2)-[β-D-galactopyranosyl(1->3)]-[β-D-glucopyranosyl-(1->6)]-β-D-glucopyranosyl} ester → D-quionovose (7658-08-4,478518-52-4) + D-glucose (50-99-7) + D-Galactose (59-23-4) + bayogenin (465-00-9,6989-24-8,87392-68-5,102519-34-6,106293-97-4,118711-55-0,150821-16-2)

Guidance literature:

bayogenin {28-O-α-L-rhamnopyranosyl-(1->2)-[β-D-galactopyranosyl(1->3)]-[β-D-glucopyranosyl-(1->6)]-β-D-glucopyranosyl} ester; With sulfuric acid; In 1,4-dioxane; for 1h; Reflux;

In 1,4-dioxane;

DOI:10.1248/cpb.59.889

Reference yield: 61.4%

desacylperennisoside XI → D-quionovose (7658-08-4,478518-52-4) + D-glucose (50-99-7) + D-Galactose (59-23-4) + bayogenin (465-00-9,6989-24-8,87392-68-5,102519-34-6,106293-97-4,118711-55-0,150821-16-2)

Guidance literature:

desacylperennisoside XI; With sulfuric acid; In 1,4-dioxane; for 1h; Reflux;

In 1,4-dioxane;

DOI:10.1248/cpb.59.889

Reference yield: 52.2%

desacyl-perennisoside VIII → D-quionovose (7658-08-4,478518-52-4) + D-Fucose (3615-37-0,478518-52-4) + D-glucose (50-99-7) + bayogenin (465-00-9,6989-24-8,87392-68-5,102519-34-6,106293-97-4,118711-55-0,150821-16-2)

Guidance literature:

desacyl-perennisoside VIII; With sulfuric acid; In 1,4-dioxane; for 1h; Reflux;

In 1,4-dioxane;

DOI:10.1248/cpb.59.889

upstream raw materials:

3-O-<α-L-arabinopyranosyl(1->2)-β-D-glucopyranosyl>-bayogenin

lobatoside C

undeca-acetate of medicoside J

3-O-β-D-glucopyranosyl-2β,3β,23-trihydroxyolean-12-en-28-oic acid-28-O-β-D-xylopyranosyl-(1→6)-[β-D-glucopyranosyl-(1→2)]-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranoside

Downstream raw materials:

C₃₂H₄₈O₆

C₃₀H₄₆O₅

olean-12-ene-2β,3β,23,28-tetraol

Barringtogenol

Refernces

• 1、 Tava, Aldo,Biazzi, Elisa,Mella, Mariella,Quadrelli, Paolo,Avato, Pinarosa. "Artefact formation during acid hydrolysis of saponins from Medicago spp.". . p. 116 - 127. Retrieved 2017/04/13.
• 2、 Scognamiglio, Monica,D'Abrosca, Brigida,Fiumano, Vittorio,Chambery, Angela,Severino, Valeria,Tsafantakis, Nikolaos,Pacifico, Severina,Esposito, Assunta,Fiorentino, Antonio. "Oleanane saponins from Bellis sylvestris Cyr. and evaluation of their phytotoxicity on Aegilops geniculata Roth". . p. 125 - 134,10. Retrieved 2012/12/12.