Chrysin-7beta-monoglucoside

Base Information

• Chemical Name: Chrysin-7beta-monoglucoside
• CAS No.: 31025-53-3
• Molecular Formula: C21H20 O9
• Molecular Weight: 416.384
• DSSTox Substance ID: DTXSID80184998
• Nikkaji Number: J94.444K
• Mol file: 31025-53-3.mol

Synonyms:5,7-dihydroxyflavone-7 beta-monoglucoside;chrysin-7 beta-monoglucoside

Chemical Property of Chrysin-7beta-monoglucoside

Chemical Property:

• Vapor Pressure: 8.74E-23mmHg at 25°C
• Boiling Point: 736.7°C at 760 mmHg
• Flash Point: 263.1°C
• PSA: 149.82000
• Density: 1.572g/cm³
• LogP: 0.34430
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 4
• Exact Mass: 416.11073221
• Heavy Atom Count: 30
• Complexity: 646

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=CC(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)O
• Isomeric SMILES: C1=CC=C(C=C1)C2=CC(=O)C3=C(C=C(C=C3O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
• Use Description: AEQUINETIN is a specialized chemical compound with distinct roles in various fields. In the realm of agriculture and plant science, it serves as a natural phytochemical found in certain plant species and plays a role in plant defense mechanisms against herbivores and pathogens. Its presence can deter herbivores and protect plants from potential threats, contributing to pest control and plant health. In medicinal chemistry and pharmaceuticals, AEQUINETIN may be explored for its potential pharmacological properties and used as a lead compound in drug discovery research. Its structural features and biological activities could aid in the development of novel therapeutic agents. Additionally, in chemical research, AEQUINETIN serves as an interesting target for the synthesis of complex molecules, contributing to advancements in organic chemistry and the exploration of diverse chemical reactions. Its applications in agriculture, pharmaceuticals, and organic synthesis underscore its significance in plant protection, drug development, and chemical innovation within these distinct domains.

Technology Process of Chrysin-7beta-monoglucoside

There total 9 articles about Chrysin-7beta-monoglucoside 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: 99.0%

5-hydroxy-2-phenyl-7-(tetra-O-acetyl-β-D-glucopyranosyloxy)-4H-1-benzopyran-4-one (62055-04-3) → 7-(β-D-glucopyranosyloxy)-5-hydroxy-2-phenyl-4H-1-benzopyran-4-one (31025-53-3)

Guidance literature:

With potassium hydroxide; In ethanol; for 3h; Heating;

DOI:10.1002/(SICI)1522-2675(19991215)82:12<2201::AID-HLCA2201>3.0.CO;2-4

Reference yield: 23.0%

5,7-dihydroxy-2-phenyl-chromen-4-one (480-40-0) → 7-(β-D-glucopyranosyloxy)-5-hydroxy-2-phenyl-4H-1-benzopyran-4-one (31025-53-3)

Guidance literature:

In dimethyl sulfoxide; for 168h; regioselective reaction; Microbiological reaction;

DOI:10.1016/j.bioorg.2019.01.046

Reference yield: 14.0%

5,7-dihydroxy-2-phenyl-chromen-4-one (480-40-0) → 7-(β-D-glucopyranosyloxy)-5-hydroxy-2-phenyl-4H-1-benzopyran-4-one (31025-53-3)

Guidance literature:

In dimethyl sulfoxide; for 168h; regioselective reaction; Microbiological reaction;

DOI:10.1016/j.bioorg.2019.01.046

upstream raw materials:

5-hydroxy-2-phenyl-7-(tetra-O-acetyl-β-D-glucopyranosyloxy)-4H-1-benzopyran-4-one

5,7-dihydroxy-2-phenyl-chromen-4-one

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

chrysin 7-O-α-L-arabinopyranosyl-(1->6)-β-D-glucopyranoside

Downstream raw materials:

5-acetoxy-2-phenyl-7-(tetra-O-acetyl-β-D-glucopyranosyloxy)-chromen-4-one

7-β-D-glucopyranosyloxy-5-methoxy-2-phenyl-chromen-4-one

5-hydroxy-2-phenyl-7-(tetra-O-acetyl-β-D-glucopyranosyloxy)-4H-1-benzopyran-4-one

Refernces

• 1、 Yang, Yan,Liu, Minzhi,Zhang, Wenxuan,Cao, Yunsong,Li, Changkun,Wang, Wei. "Identification and Characterization of Two New 1- O-Acyl-glucose-ester Forming Glucosyltransferases from Erigeron breviscapus". . p. 2848 - 2855. Retrieved 2019/03/19.
• 2、 Alluis, Bertrand,Dangles, Olivier. "Acylated flavone glucosides: Synthesis, conformational investigation, and complexation properties". . p. 2201 - 2212. Retrieved 2007/10/03.