2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one

Base Information

• Chemical Name: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• CAS No.: 482-35-9
• Molecular Formula: C21H20 O12
• Molecular Weight: 464.383
• Hs Code.: 29389090
• NSC Number: 115918,407304
• DSSTox Substance ID: DTXSID60859399
• Wikidata: Q104193829
• NCI Thesaurus Code: C99879
• Metabolomics Workbench ID: 131078
• ChEMBL ID: CHEMBL33027
• Mol file: 482-35-9.mol

Synonyms:2-(3,4-dihydroxyphenyl)-3-(beta-D-glucofuranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-one;4H-1-benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3-(beta-D-glucofuranosyloxy)-5,7-dihydroxy;flavone, 3,3',4',5,7-pentahydroxy-, 3-beta-D-glucofuranoside;isoquercetin;isoquercitin;isoquercitrin;isoquercitroside;isotrifoliin;quercetin 3-(beta-D-glucofuranoside);quercetin 3-O-beta-D-glucofuranoside;quercetin-3-glucoside;quercetin-3-O-beta-glucoside;quercetin-3-O-glucoside;trifoliin;trifoliin A

Chemical Property of 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 230 °C
• Boiling Point: 872.6°Cat760mmHg
• PKA: 6.17±0.40(Predicted)
• Flash Point: 307.4°C
• PSA: 210.51000
• Density: 1.87g/cm³
• LogP: -0.53890
• Storage Temp.: −20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 4
• Exact Mass: 464.09547607
• Heavy Atom Count: 33
• Complexity: 758

Purity/Quality:

95%-98% ^*data from raw suppliers

Quercetin 3-O-β-D Glucoside ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)CO)O)O)O)O)O
• Uses: Isoquercitrin was used as standard to compare the retention time of samples for identifying chromatographic peaks during flavonoid identification by Orbitrap UHPLC-MS/MS analysis. Quercetin 3-β-D-glucoside has been used:as a dietary flavonoid supplement to check its binding capacity with human small ubiquitin-related modifier 1 (SUMO1) protein using surface plasmon resonance (SPR)as an inhibitor for Escherichia coli adenosine triphosphate (ATP) synthaseas an anti-aggregation agent to test its activity against β-amyloid, green fluorescent protein?(GFP), and chymotrypsinogen proteins

Technology Process of 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one

There total 43 articles about 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one 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%

rutin (153-18-4) → isoquercetin (482-35-9)

Guidance literature:

With Aspergillus niger crude enzyme extract; In methanol; at 60 ℃; for 4h; pH=6; aq. piperazine-HCl buffer; Enzymatic reaction;

DOI:10.1021/jf102871g

Reference yield: 98.8%

rutin → isoquercetin (482-35-9)

Guidance literature:

With disodium hydrogen phosphate-sodium citrate buffer; rhamnosidase; at 45 ℃; for 24h; pH=6; Enzymatic reaction;

Reference yield: 98.0%

4',7-di-O-benzyl-3-O-(β-D-glucopyranosyl)quercetin (6743-87-9) → isoquercetin (482-35-9)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; ethyl acetate; at 20 ℃; Inert atmosphere;

DOI:10.1080/07328303.2011.616979

upstream raw materials:

UDP-glucose

quercetol

3,,4,,5,7-tetrahydroxyflavonol 3-O-β-D-glucopyranosyl (2->1) O-β-D-xylopyranoside

6''-O-<2-(methoxycarbonyl)acetyl>isoquercitrin

Downstream raw materials:

3',4',5,7-tetra-O-acetylquercetin 3-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranoside)

6''-O-<2-(methoxycarbonyl)acetyl>isoquercitrin

quercetol

D-Glucose

Refernces

• 1、 Hori, Yuichiro,Miki, Yoshinobu,Morikawa, Toshio,Muraoka, Osamu,Nagatomo, Akifumi,Ninomiya, Kiyofumi,Oka, Takahiro,Shibano-Kitahara, Megumi,Taira, Norihisa. "Glucose tolerance-improving activity of helichrysoside in mice and its structural requirements for promoting glucose and lipid metabolism". . . Retrieved 2019.
• 2、 Bae, Jae Yoon,Darsandhari, Sumangala,Han, Jang Mi,Jung, Hye Jin,Pandey, Ramesh Prasad,Rha, Chan-Su,Shrestha, Biplav,Sohng, Jae Kyung,Yamaguchi, Tokutaro. "Enzymatic synthesis of novel quercetin sialyllactoside derivatives". . p. 1944 - 1952. Retrieved 2019.