Isovitexin

Base Information

• Chemical Name: Isovitexin
• CAS No.: 38953-85-4
• Deprecated CAS: 61383-34-4,29702-25-8,3681-94-5,36025-68-0
• Molecular Formula: C₂₁H₂₀O₁₀
• Molecular Weight: 432.384
• Hs Code.: 29329990
• European Community (EC) Number: 609-600-2
• UNII: KTQ9R9MS0Q
• DSSTox Substance ID: DTXSID60952152
• Nikkaji Number: J16.502F
• Wikipedia: Isovitexin
• Wikidata: Q3155636
• ChEMBL ID: CHEMBL465360
• Mol file: 38953-85-4.mol

Synonyms:6-glucosyl-apigenin;6-glucosylapigenin;apigenin 6-C-glucoside;isovitexin

Chemical Property of Isovitexin

Chemical Property:

• Vapor Pressure: 1.68E-27mmHg at 25°C
• Melting Point: 257-258 °C
• Refractive Index: 1.743
• Boiling Point: 807 °C at 760 mmHg
• PKA: 5.93±0.40(Predicted)
• Flash Point: 287.1 °C
• PSA: 181.05000
• Density: 1.686g/cm³
• LogP: 0.09170
• Storage Temp.: ?20°C
• 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:

≥98% ^*data from raw suppliers

Isovitexin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C=C(C(=C3O)C4C(C(C(C(O4)CO)O)O)O)O)O
• Isomeric SMILES: C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C=C(C(=C3O)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O
• Uses: Isovitexin is known as a flavones, a class of flavonoids. Isovitexin have been studied for their antiradical activities in the process of metabolisms. Isovitexin have also been studied for beneficial effcts against atherosclerosis, osteoporosis and certain cancers. Isovitexin can be used to study biochemicals found in plants and nutrition. Isovitexin has been used in a study to assess collagenase inhibitors from Viola yedoensis. Isovitexin has also been used in a study to investigate the inhibitory activity of Gentiana lutea extracts on the enzyme myeloperoxidase (MPO), as well as the antioxidant activity of these extracts and their correlation with the total polyphenol content.

Technology Process of Isovitexin

There total 24 articles about Isovitexin 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: 88.0%

7-benzyloxy-2-(4-benzyloxyphenyl)-5-hydroxy-6-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-4H-1-benzopyran-4-one → isovitexin (29702-25-8,29774-68-3,36025-68-0,38953-85-4,47678-46-6,53152-14-0,70116-01-7)

Guidance literature:

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

Reference yield: 87.0%

5,7,4'-trihydroxy-6-C-(β-D-glucopyranosyl)flavone peracetate (10515-29-4) → isovitexin (29702-25-8,29774-68-3,36025-68-0,38953-85-4,47678-46-6,53152-14-0,70116-01-7)

Guidance literature:

5,7,4'-trihydroxy-6-C-(β-D-glucopyranosyl)flavone peracetate; With sodium methylate; In methanol; at 25 ℃; for 5h;

In methanol;

DOI:10.1039/c0ob00011f

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 2-O-sulfate

5,7,4'-trihydroxy-6-C-(β-D-glucopyranosyl)flavone peracetate

vitexin

5,7,4'-trihydroxyflavone 6-C-(2''-O-β-D-glucopyranosyl-β-D-glucopyranoside)

Downstream raw materials:

C₂₈H₂₄O₁₃S

C₂₈H₂₄O₁₀

isovitexin 2-O-sulfate

chafuroside B

Refernces

• 1、 Olennikov,Chirikova. "C-Glycosyl Flavones from Two Eastern Siberian Species of Silene". . p. 642 - 647. Retrieved 2019/08/08.
• 2、 Hao,Caulfield,Hamilton,Pickett,Midega,Khan,Wang,Hooper. "Biosynthesis of natural and novel C-glycosylflavones utilising recombinant Oryza sativa C-glycosyltransferase (OsCGT) and Desmodium incanum root proteins". . p. 73 - 87. Retrieved 2016/04/06.