Isosalipurposide

Base Information

• Chemical Name: Isosalipurposide
• CAS No.: 4547-85-7
• Molecular Formula: C₂₁H₂₂O₁₀
• Molecular Weight: 434.4
• DSSTox Substance ID: DTXSID801316840
• Nikkaji Number: J365.718C,J107.406G
• Wikidata: Q27149537
• ChEMBL ID: CHEMBL2430461
• Mol file: 4547-85-7.mol

Synonyms:iso-salipurposide;isosalipurposide;phlorizin chalcone

Chemical Property of Isosalipurposide

Chemical Property:

• Vapor Pressure: 4.64E-25mmHg at 25°C
• Melting Point: 172-173 °C
• Boiling Point: 771.8°Cat760mmHg
• PKA: 6.93±0.40(Predicted)
• Flash Point: 272.2°C
• PSA: 177.14000
• Density: 1.595g/cm³
• LogP: -0.12180
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 6
• Exact Mass: 434.12129689
• Heavy Atom Count: 31
• Complexity: 619

Purity/Quality:

98.5% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C=CC(=O)C2=C(C=C(C=C2OC3C(C(C(C(O3)CO)O)O)O)O)O)O
• Isomeric SMILES: C1=CC(=CC=C1/C=C/C(=O)C2=C(C=C(C=C2O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O)O
• Uses: Isosalipurposide is a plant metabolite and an antioxidant. A beta-D-glucoside and a monosaccharide derivative. Isosalipurposide has a cytoprotective effect against oxidative damage mediated through Nrf2 activation.

Technology Process of Isosalipurposide

There total 6 articles about Isosalipurposide 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: 40.8%

4-O-Benzoylphloracetophenone 2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside) (130471-79-3) → 2,4,4',6-Tetrahydroxychalcone 2'-O-α-D-mannopyranoside (4547-85-7,72843-28-8,114612-67-8,121545-97-9,130549-92-7,138665-97-1,20565-42-8,26107-98-2,28757-26-8)

Guidance literature:

With potassium hydroxide; In ethanol; Ambient temperature;

Reference yield:

2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl chloride (572-10-1,4451-35-8,4451-36-9,14227-52-2,14227-87-3,14227-88-4,14257-40-0,17081-03-7,19186-60-8,57237-01-1,65982-17-4,65982-18-5,65982-19-6,66966-08-3,144299-57-0) → 2,4,4',6-Tetrahydroxychalcone 2'-O-α-D-mannopyranoside (4547-85-7,72843-28-8,114612-67-8,121545-97-9,130549-92-7,138665-97-1,20565-42-8,26107-98-2,28757-26-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 29.2 percent / mercuric cyanide / nitromethane / Heating

2: 40.8 percent / 60 percent aq. KOH / ethanol / Ambient temperature

With potassium hydroxide; mercury(II) cyanide; In nitromethane; ethanol;

Reference yield:

ο-Benzoyloxy-phloracetophenon (130471-75-9) → 2,4,4',6-Tetrahydroxychalcone 2'-O-α-D-mannopyranoside (4547-85-7,72843-28-8,114612-67-8,121545-97-9,130549-92-7,138665-97-1,20565-42-8,26107-98-2,28757-26-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 29.2 percent / mercuric cyanide / nitromethane / Heating

2: 40.8 percent / 60 percent aq. KOH / ethanol / Ambient temperature

With potassium hydroxide; mercury(II) cyanide; In nitromethane; ethanol;

upstream raw materials:

naringenin-5-O-glucoside

4-hydroxy-benzaldehyde

4-O-Benzoylphloracetophenone 2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside)

ο-Benzoyloxy-phloracetophenon

Downstream raw materials:

naringenin-5-O-glucoside

phloridizin

phloretin 2'-O-β-L-glucopyranoside

5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on

Refernces