Vitexin

Base Information

• Chemical Name: Vitexin
• CAS No.: 3681-93-4
• Deprecated CAS: 521-33-5
• Molecular Formula: C₂₁H₂₀O₁₀
• Molecular Weight: 432.384
• Hs Code.: 29389090
• European Community (EC) Number: 222-963-8
• UNII: 9VP70K75OK
• ChEMBL ID: CHEMBL487417
• DSSTox Substance ID: DTXSID90190287
• Metabolomics Workbench ID: 50716
• Nikkaji Number: J14.961F
• Wikidata: Q259075
• Wikipedia: Vitexin
• Mol file: 3681-93-4.mol

Synonyms:8-glycosyl-apigenin;8-glycosylapigenin;apigenin 8-C-glucoside;vitexin

Chemical Property of Vitexin

Chemical Property:

• Appearance/Colour: Yellow powder
• Vapor Pressure: 8.68E-25mmHg at 25°C
• Melting Point: 256-257 °C
• Refractive Index: 1.743
• Boiling Point: 767.7 °C at 760 mmHg
• PKA: 6.27±0.40(Predicted)
• Flash Point: 273.1 °C
• PSA: 181.05000
• Density: 1.686 g/cm³
• LogP: 0.09170
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: DMSO (Slightly), Pyridine (Slightly)
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 3
• Exact Mass: 432.10564683
• Heavy Atom Count: 31
• Complexity: 690

Purity/Quality:

95%-98% ^*data from raw suppliers

Vitexin ^*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: C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)C4C(C(C(C(O4)CO)O)O)O)O
• Isomeric SMILES: C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
• Uses: Vitexin is a phenolic glycoside drug that shows anti-stress activity. It also shows possible application as an anti-diabetic.

Technology Process of Vitexin

There total 23 articles about Vitexin 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: 89.0%

7-benzyloxy-2-(4-benzyloxyphenyl)-5-hydroxy-8-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-4H-1-benzopyran-4-one → vitexin (29774-67-2,35013-07-1,53152-15-1,55555-34-5,104371-58-6,3681-93-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; ethyl acetate; for 12h; under 750.06 Torr;

Reference yield: 65.0%

5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-8-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)-4H-chromen-4-one (1154756-98-5) → vitexin (29774-67-2,35013-07-1,53152-15-1,55555-34-5,104371-58-6,3681-93-4)

Guidance literature:

With hydrogen; palladium(II) hydroxide; In 1,4-dioxane; methanol; for 1h;

DOI:10.1016/j.bmcl.2010.06.077

Reference yield: 53.0%

UDP-glucose + 2,4’,5,7-tetrahydroxyflavanone → isovitexin (29702-25-8,29774-68-3,36025-68-0,38953-85-4,47678-46-6,53152-14-0,70116-01-7) + vitexin (29774-67-2,35013-07-1,53152-15-1,55555-34-5,104371-58-6,3681-93-4)

Guidance literature:

With recombinant Oryza sativa C-glycosyltransferase; In ethanol; at 30 ℃; pH=7.5; Enzymatic reaction;

DOI:10.1016/j.phytochem.2016.02.013

upstream raw materials:

isovitexin

5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-8-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)-4H-chromen-4-one

vitexin 2-O-sulfate

1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone

Downstream raw materials:

4-hydroxy-3,5-dinitrobenzoic acid

vitexin-4',7-di-O-methyl ether

7-ethoxy-2-(4-ethoxy-phenyl)-8-β-D-glucopyranosyl-5-hydroxy-chromen-4-one

5,7-diethoxy-2-(4-ethoxy-phenyl)-8-β-D-glucopyranosyl-chromen-4-one

Refernces

• 1、 Liu, Shike,Lyu, Yunbin,Yu, Shiqin,Cheng, Jie,Zhou, Jingwen. "Efficient Production of Orientin and Vitexin from Luteolin and Apigenin Using Coupled Catalysis of Glycosyltransferase and Sucrose Synthase". . p. 6578 - 6587. Retrieved 2021/06/28.
• 2、 Matos, Ana M. de,Martins, Alice,Man, Teresa,Evans, David,Walter, Magnus,Oliveira, Maria Concei??o,López, óscar,Fernandez-Bola?os, José G.,D?twyler, Philipp,Ernst, Beat,Macedo, M. Paula,Contino, Marialessandra,Colabufo, Nicola A.,Rauter, Amélia P.. "Design and Synthesis of CNb-targeted Flavones and Analogues with Neuroprotective Potential Against H2O2- and Aβ1-42-Induced Toxicity in SH-SY5Y Human Neuroblastoma Cells". . . Retrieved 2019/08/30.