Yamogenin

Base Information

• Chemical Name: Yamogenin
• CAS No.: 512-06-1
• Molecular Formula: C27H42O3
• Molecular Weight: 414.629
• UNII: M487OD4XW3
• DSSTox Substance ID: DTXSID60903922
• Nikkaji Number: J6.273A
• Wikipedia: Yamogenin
• Wikidata: Q8048088
• Metabolomics Workbench ID: 35139
• ChEMBL ID: CHEMBL400807
• Mol file: 512-06-1.mol

Synonyms:Yamogenin

Chemical Property of Yamogenin

Chemical Property:

• Appearance/Colour: White Solid
• Vapor Pressure: 2.59E-13mmHg at 25°C
• Melting Point: 193-199°C
• Refractive Index: 1.564
• Boiling Point: 527.1oC at 760 mmHg
• Flash Point: 272.6oC
• PSA: 38.69000
• Density: 1.13g/cm3
• LogP: 5.71390
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Sparingly), Ethyl Acetate (Slightly), Methanol (Slightly), Pyridine
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 414.31339520
• Heavy Atom Count: 30
• Complexity: 746

Purity/Quality:

99%, ^*data from raw suppliers

Yamogenin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CC=C6C5(CCC(C6)O)C)C)C)OC1
• Isomeric SMILES: C[C@H]1CC[C@@]2([C@H]([C@H]3[C@@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC=C6[C@@]5(CC[C@@H](C6)O)C)C)C)OC1
• 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.

Technology Process of Yamogenin

There total 31 articles about Yamogenin 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: 68.3%

pseudodiosgenin (6808-14-6,7662-13-7) → (3β,20R,22R,25R)-spirosol-5-en-3-ol (470-05-3,470-06-4,512-04-9,512-06-1,31356-47-5,51195-66-5,66289-52-9,89299-45-6,125710-71-6) + diosgenin (512-04-9)

Guidance literature:

With acetic acid; at 20 ℃;

DOI:10.1016/S0223-5234(00)00151-3

Reference yield: 15.0%

Diosgeninmonoacetat (1180-12-7) → yamogenin (512-06-1)

Guidance literature:

With di(n-butyl)tin oxide; In methanol; chloroform; for 18h; Heating;

DOI:10.1016/j.steroids.2006.10.004

Reference yield:

C63H106O22 → yamogenin (512-06-1)

Guidance literature:

With sulfuric acid; In methanol; water; for 8h; Reflux;

DOI:10.1007/s10600-016-1859-1

upstream raw materials:

(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

methanol

hydrogenchloride

ethanol

Downstream raw materials:

dehydrodiosgenin

Diosgenin monoacetate

yamogenin-acetate

diosgenin acetate

Refernces

• 1、 Sharma, S. C.,Sharma, H. C.. "OLIGOFURO- AND SPIRO-STANOSIDES OF ASPARAGUS ADSCENDENS". . p. 645 - 648. Retrieved 1984.
• 2、 Gvazava,Skhirtladze. "Steroidal saponin from Polygonatum verticillatum". . p. 1052 - 1055. Retrieved 2018/03/21.
• 3、 Farid, Huda,Haslinger, Ernst,Kunert, Olaf,Wegner, Christian,Hamburger, Matthias. "New steroidal glycosides from Balanites aegyptiaca". . p. 1019 - 1026. Retrieved 2007/10/03.