Sophoricoside

Base Information

• Chemical Name: Sophoricoside
• CAS No.: 152-95-4
• Deprecated CAS: 100455-45-6
• Molecular Formula: C21H20O10
• Molecular Weight: 432.384
• Hs Code.: 29329990
• UNII: J0407L5MGM
• DSSTox Substance ID: DTXSID601017840
• Nikkaji Number: J5.870J
• Wikipedia: Sophoricoside
• Wikidata: Q7563141
• Metabolomics Workbench ID: 138537
• ChEMBL ID: CHEMBL486626
• Mol file: 152-95-4.mol

Synonyms:sophoricoside

Chemical Property of Sophoricoside

Chemical Property:

• Appearance/Colour: off-white powder
• Melting Point: 285oC
• Refractive Index: 1.5376 (estimate)
• Boiling Point: 763.3 °C at 760 mmHg
• PKA: 6.45±0.20(Predicted)
• Flash Point: 271.5 °C
• PSA: 170.05000
• Density: 1.642 g/cm³
• LogP: 0.04990
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: Aqueous Base (Slightly), DMSO (Slightly, Heated), Pyridine (Slightly, Sonicated)
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 4
• Exact Mass: 432.10564683
• Heavy Atom Count: 31
• Complexity: 675

Purity/Quality:

Sophoricoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,C
• Hazard Codes: T,C
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C2=COC3=CC(=CC(=C3C2=O)O)O)OC4C(C(C(C(O4)CO)O)O)O
• Isomeric SMILES: C1=CC(=CC=C1C2=COC3=CC(=CC(=C3C2=O)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
• Uses: Genistein 4''-β-D-glucopyranoside is a metabolite of Genistein (G350000), which exhibits specific inhibitory activity against tyrosine kinases,including autophosphorylation of epidermal growth factor receptor kinase (IC50 - 2.6uM). Also inhibits other protein kinases through competitive inhibition of ATP. Inhibits tumor cell proliferation and induces tumor cell differentiation.

Technology Process of Sophoricoside

There total 8 articles about Sophoricoside 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:

UDP-glucose (133-89-1) + 5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on (446-72-0) → sophoricoside (152-95-4) + genistin (529-59-9) + Genistein 7-O-β-D-glucopyranoside-4'-O-β-D-glucopyranoside

Guidance literature:

With glycosyltransferases YojK bacillus licheniformi; magnesium chloride; In dimethyl sulfoxide; at 30 ℃; for 3h; pH=8.8; Enzymatic reaction;

DOI:10.1021/acs.orglett.9b03040

Reference yield:

Acetic acid (2R,3S,4R,5S,6S)-4,5-diacetoxy-6-acetoxymethyl-2-[4-(5,7-dihydroxy-4-oxo-4H-chromen-3-yl)-phenoxy]-tetrahydro-pyran-3-yl ester → 5,7-dihydroxy-3-[4-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one (152-95-4)

Guidance literature:

With sodium methylate; In methanol; Yield given;

DOI:10.1016/S0040-4039(98)02124-8

Reference yield:

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on (446-72-0) → 5,7-dihydroxy-3-[4-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one (152-95-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) t-BuOK, 2.) 18-crown-6 / 1.) acetonitrile, 12 h, 25 deg C, 2.) acetonitrile, 3.) acetonitrile, 5 h

2: NaOMe / methanol

With 18-crown-6 ether; potassium tert-butylate; sodium methylate; In methanol;

DOI:10.1016/S0040-4039(98)02124-8

upstream raw materials:

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on

5-hydroxy-3-(4-hydroxy-phenyl)-7-(4-nitro-benzyloxy)-chromen-4-one

UDP-glucose

2,3,4,6-tetra-O-acetyl-α-L-glucopyranosyl bromide

Downstream raw materials:

hexaacetylsophoricoside

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on

4-{5,7-dihydroxy-6,8-bis[(4-methylpiperidin-1-yl)methyl]-4-oxo-4H-chromen-3-yl}phenyl-β-D-glucopyranoside

4-{5,7-dihydroxy-6,8-bis[(3-methylpiperidin-1-yl)methyl]-4-oxo-4H-chromen-3-yl}phenyl-β-D-glucopyranoside

Refernces

• 1、 Pandey, Ramesh Prasad,Bashyal, Puspalata,Parajuli, Prakash,Yamaguchi, Tokutaro,Sohng, Jae Kyung. "Two trifunctional leloir glycosyltransferases as biocatalysts for natural products glycodiversification". supporting information. p. 8058 - 8064. Retrieved 2019/10/14.