Gitogenin

Base Information

• Chemical Name: Gitogenin
• CAS No.: 511-96-6
• Molecular Formula: C27H44 O4
• Molecular Weight: 432.644
• European Community (EC) Number: 866-822-4
• UNII: 60ZMY8IH51
• DSSTox Substance ID: DTXSID101023656
• Nikkaji Number: J6.270G
• Wikidata: Q5880476
• Metabolomics Workbench ID: 35104
• ChEMBL ID: CHEMBL1770687
• Mol file: 511-96-6.mol

Synonyms:gitogenin

Chemical Property of Gitogenin

Chemical Property:

• Vapor Pressure: 1.22E-13mmHg at 25°C
• Melting Point: 272-273oC
• Refractive Index: 1.4840 (estimate)
• Boiling Point: 534.2oC at 760 mmHg
• PKA: 14.62±0.70(Predicted)
• Flash Point: 276.9oC
• PSA: 58.92000
• Density: 1.16g/cm3
• LogP: 4.76460
• XLogP3: 5.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 432.32395988
• Heavy Atom Count: 31
• Complexity: 726

Purity/Quality:

99%, ^*data from raw suppliers

Gitogenin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CCC6C5(CC(C(C6)O)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(C[C@H]([C@@H](C6)O)O)C)C)C)OC1
• Uses: Gitogenin is isolated from a methanolic extract of the whole plant of Tribulus longipetalus which exhibits inhibitory activities against α-glucosidase, lipoxygenase, acetylcholinesterase and butyrylcholinesterase.

Technology Process of Gitogenin

There total 14 articles about Gitogenin 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:

(25R)-2α-hydroxy-5α-spirostan-3β-yl O-β-D-galactopyranosyl-(1 → 2)-O-[β-D-glucopyranosyl-(1 → 3)]-O-β-D-glucopyranosyl-(1 → 4)-β-D-galactopyranoside (1499187-77-7) → D-glucose (50-99-7) + D-Galactose (59-23-4) + gitogenin (511-96-6)

Guidance literature:

With naringinase; potassium acetate; acetic acid; In aq. buffer; at 20 ℃; for 49h; pH=4.3; Enzymatic reaction;

DOI:10.1016/j.phytochem.2013.09.023

Reference yield:

(25R)-26-[(β-D-glucopyranosyl)oxy]-2α,22α-dihydroxy-5α-furostan-3β-yl O-β-D-galactopyranosyl-(1 → 2)-O-[β-D-glucopyranosyl-(1 → 3)]-O-β-D-glucopyranosyl-(1 → 4)-β-D-galactopyranoside (1499190-07-6) → D-glucose (50-99-7) + D-Galactose (59-23-4) + gitogenin (511-96-6)

Guidance literature:

With naringinase; potassium acetate; acetic acid; In aq. buffer; at 20 ℃; for 49h; pH=4.3; Enzymatic reaction;

DOI:10.1016/j.phytochem.2013.09.023

Reference yield:

(25R)-26-[(β-D-glucopyranosyl)oxy]-2α-hydroxy-5α-furost-20(22)-en-3β-yl O-β-D-galactopyranosyl-(1 → 2)-O-[β-D-xylopyranosyl-(1 → 3)]-O-β-D-glucopyranosyl-(1 → 4)-β-D-galactopyranoside → D-xylose (58-86-6) + D-glucose (50-99-7) + D-Galactose (59-23-4) + gitogenin (511-96-6)

Guidance literature:

With naringinase; potassium acetate; acetic acid; In aq. buffer; at 20 ℃; for 49h; pH=4.3; Enzymatic reaction;

DOI:10.1016/j.phytochem.2013.09.023

upstream raw materials:

26-O-β-D-glucopyranosyl-(25R)-5α-furostan-2α,3β,22α,26-tetraol 3-O-[β-D-glucopyranosyl-(1->2)-[β-D-xylopyranosyl-(1->3)]-β-D-glucopyranosyl-(1->4)]-β-D-galactopyranoside

(25R)-2α-hydroxy-5α-spirostan-3β-yl O-β-D-galactopyranosyl-(1 → 2)-O-[β-D-glucopyranosyl-(1 → 3)]-O-β-D-glucopyranosyl-(1 → 4)-β-D-galactopyranoside

(25R)-26-[(β-D-glucopyranosyl)oxy]-2α,22α-dihydroxy-5α-furostan-3β-yl O-β-D-galactopyranosyl-(1 → 2)-O-[β-D-glucopyranosyl-(1 → 3)]-O-β-D-glucopyranosyl-(1 → 4)-β-D-galactopyranoside

(25R)-5β-spirost-2-ene

Downstream raw materials:

markogenin

Refernces

• 1、 Matsuo, Yukiko,Akagi, Nana,Hashimoto, Chisato,Tachikawa, Fumito,Mimaki, Yoshihiro. "Steroidal glycosides from the bulbs of Bessera elegans and their cytotoxic activities". . p. 244 - 256. Retrieved 2014/01/06.