Sarsasapogenin

Base Information

• Chemical Name: Sarsasapogenin
• CAS No.: 126-19-2
• Molecular Formula: C27H44O3
• Molecular Weight: 416.645
• Hs Code.: 2932990090
• European Community (EC) Number: 204-776-3
• UNII: CFS802C28F
• DSSTox Substance ID: DTXSID00903921
• Nikkaji Number: J5.383J
• Wikipedia: Sarsasapogenin
• Wikidata: Q7424590
• NCI Thesaurus Code: C152305
• Pharos Ligand ID: 47JU6GNJUDWS
• Metabolomics Workbench ID: 35101
• ChEMBL ID: CHEMBL1171146
• Mol file: 126-19-2.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 Sarsasapogenin

Chemical Property:

• Appearance/Colour: white or off-withe powder
• Vapor Pressure: 7.83E-13mmHg at 25°C
• Melting Point: 194 °C
• Refractive Index: 1.552
• Boiling Point: 516.6 °C at 760 mmHg
• PKA: 15.14±0.70(Predicted)
• Flash Point: 266.2 °C
• PSA: 38.69000
• Density: 1.11 g/cm³
• LogP: 5.79380
• Storage Temp.: 2-8°C
• 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:

more than 98% ^*data from raw suppliers

Sarsasapogenin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

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
• Recent ClinicalTrials: Investigation of Cogane (PYM50028) in Early-stage Parkinson's Disease (CONFIDENT-PD)
• Description: Smilagengenin is a steroidal saponin with antitumor activity, which is mainly used in refreshing beverages, foaming sweets, mixed wine, etc.
• Uses: Sarsasapogenin has cytotoxic properties and is used to develop lead structures for cancer drugs. Sarsasapogenin is also identified to effectively lower the production of Aβ amyloids and stimulate neurite ogrowth in neuronal cell cultures.

Technology Process of Sarsasapogenin

There total 90 articles about Sarsasapogenin 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

smilagenin

sarsasapogenin acetate

Refernces

• 1、 Sharma, S. C.,Chand, R.,Sati, O. P.. "STEROIDAL SAPONINS OF ASPARAGUS ADSCENDENS". . p. 2075 - 2078. Retrieved 1982.
• 2、 Sharma,Thakur. "Oligofurostanosides and oligospirostanosides from roots of Asparagus filicinus". . p. 599 - 603. Retrieved 1996.
• 3、 Lajis, Nordin H.,Abdullah, A. Salam H.,Salim, S. Jalaludin S.,Bremner, John B.,Khan, Mohammad Niyaz. "Epi-Sarsasapogenin and epi-smilagenin: two sapogenins isolated from the rumen content of sheep intoxicated by Brachiaria decumbens". . p. 387 - 389. Retrieved 1993.
• 4、 Mandal, Debayan,Banerjee, Sukdeb,Mondal, Nirup B.,Chakravarty, Ajit K.,Sahu, Niranjan P.. "Steroidal saponins from the fruits of Asparagus racemosus". . p. 1316 - 1321. Retrieved 2006.
• 5、 Flueckinger. "-". . p. 532,540. Retrieved 1877.
• 6、 Boudreault, Pierre-Luc,Normandin, Chad. "Concise large-scale synthesis of tomatidine, a potent antibiotic natural product". . . Retrieved 2021/10/12.
• 7、 -. "Diosgenin derivatives, and pharmaceutical compositions thereof and application thereof". . . Retrieved 2019/01/24.