Epismilagenin

Base Information

• Chemical Name: Epismilagenin
• CAS No.: 16653-88-6
• Molecular Formula: C₂₇H₄₄O₃
• Molecular Weight: 416.645
• Nikkaji Number: J835.369G
• Mol file: 16653-88-6.mol

Synonyms:epi-sarsasapogenin;epismilagenin;PYM 50028;PYM-50028;PYM50028;sarsaponin;sarsasapogenin;sarsasapogenin, (3beta,5alpha,25R)-isomer;sarsasapogenin, (3beta,5alpha,25S)-isomer;sarsasapogenin, (3beta,5beta)-isomer;sarsasapogenin, (3beta,5beta,25R)-isomer;sarsasapogenin, (3beta,5beta,25S)-isomer;smilagenin;tigogenin

Chemical Property of Epismilagenin

Chemical Property:

• Vapor Pressure: 7.83E-13mmHg at 25°C
• Melting Point: 217-220 °C
• Boiling Point: 516.6°Cat760mmHg
• PKA: 15.14±0.70(Predicted)
• Flash Point: 266.2°C
• Density: 1.11g/cm³
• XLogP3: 6.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 416.32904526
• Heavy Atom Count: 30
• Complexity: 694

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CCC6C5(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[C@H]6[C@@]5(CC[C@H](C6)O)C)C)C)OC1

Technology Process of Epismilagenin

There total 50 articles about Epismilagenin 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: 62.0%

C27H43NO4 → Neotigogenin (77-60-1,126-18-1,126-19-2,428-41-1,470-00-8,470-01-9,470-03-1,546-41-8,6788-40-5,7050-46-6,16653-88-6,19043-98-2,20460-38-2,31356-48-6,36027-61-9,36136-35-3,75172-34-8,78964-18-8,82597-74-8,107380-02-9,119677-72-4) + neotigogenone (5159-14-8)

Guidance literature:

In solid; for 168h; Irradiation;

DOI:10.1246/cl.1996.217

Reference yield: 33.1%

26-O-β-D-glucopyransoyl-(25S)-5β-furostane-3β,22ξ,26-triol 3-O-[α-L-rhamnopyranosyl (1->)]-β-D-glucopyranside → Neotigogenin (77-60-1,126-18-1,126-19-2,428-41-1,470-00-8,470-01-9,470-03-1,546-41-8,6788-40-5,7050-46-6,16653-88-6,19043-98-2,20460-38-2,31356-48-6,36027-61-9,36136-35-3,75172-34-8,78964-18-8,82597-74-8,107380-02-9,119677-72-4)

Guidance literature:

With hydrogenchloride; In ethanol; for 3h; Heating;

DOI:10.1248/cpb.45.81

Reference yield:

tribulosin (79974-46-2) → D-xylose (58-86-6) + L-Rhamnose (3615-41-6,478518-52-4) + D-Galactose (59-23-4) + Neotigogenin (77-60-1,126-18-1,126-19-2,428-41-1,470-00-8,470-01-9,470-03-1,546-41-8,6788-40-5,7050-46-6,16653-88-6,19043-98-2,20460-38-2,31356-48-6,36027-61-9,36136-35-3,75172-34-8,78964-18-8,82597-74-8,107380-02-9,119677-72-4)

Guidance literature:

With hydrogenchloride; In ethanol; water; for 5h; Further byproducts given;

DOI:10.1039/P19810002405

upstream raw materials:

(25R)-5β-spirostan-3-one

(25R)-spirost-4-ene-3-one

diosgenin

(4S,5′S,6aS,8aS,9S,10R,11aS)-5′,6a,8a,9-tetramethyldocosahydrospiro[naphtho[2′,1′:4,5]indeno[2,1-b]furan-10,2′-pyran]-4-yl acetate

Downstream raw materials:

tigogenyl acetate

C₅₃H₇₈O₂₀

tomatidine acetate

tomatidine

Refernces

• 1、 Boudreault, Pierre-Luc,Normandin, Chad. "Concise large-scale synthesis of tomatidine, a potent antibiotic natural product". . . Retrieved 2021/10/12.
• 2、 -. "Diosgenin derivatives, and pharmaceutical compositions thereof and application thereof". . . Retrieved 2019/01/24.