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.: 482-36-0
• Molecular Formula: C21H20O12
• 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: 482-36-0.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: 225-226 °C
• Refractive Index: 1.803
• Boiling Point: 872.6 °C at 760 mmHg
• PKA: 6.17±0.40(Predicted)
• Flash Point: 307.4 °C
• PSA: 210.51000
• Density: 1.87 g/cm³
• LogP: -0.53890
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)
• 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:

99%, ^*data from raw suppliers

Quercetin 3-b-D-galactoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-40
• Safety Statements: 22-45-36-24/25

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
• Description: Hypericin, which is widely found in various plants, such as Hypericum, Rosaceae, Campanulaceae, Labiatae, Rhododendron, Asteraceae Kwai, Garciniaceae, Leguminosae, Euonymus, and other fruits and whole grass, is a flavonoid compound.
• Physical properties: Appearance: yellowish needlelike crystals. Melting point: 227–229 °C. Specific optical rotation: ?83° (c = 0.2, pyridine). Solubility: soluble in ethanol, methanol, acetone, and pyridine. Hydrochloric acid–magnesium powder reaction yielded formation of cherry red; ferric chloride reaction was green; α-naphthol reaction was positive.
• Uses: It may be used as calibration standard solutions in method validation of polyphenols from leaf extracts using HPLC method. Hyperoside is used as a primary reference standard in the analysis of herbal medicinal products. It may be used as a calibration standard in method validation of polyphenols from leaf extracts using HPLC method. A major flavonoid in apple peels; a bioactive constituent of apple peels
• Indications: This product is available in the British Pharmacopoeia (2017) and the European Pharmacopoeia (9.0th ed.). Monomeric compounds are currently used clinically. In clinical practice, hypericin is the main active ingredient of proprietary Chinese medicines, such as Acanthopanax capsules, of which Acanthopanax stem and leaf extract are the raw materials for the preparation. Xin’an capsules, prepared with hawthorn leaf extract, are rich in flavonoids, in which hyperoside, a kind of flavonoid, is one of the main components. Qi yue lipid-lowering tablets are prepared from the effective parts of Chinese medicinal herbs such as hawthorn (Nucleation) and Astragalus membranaceus. Flavonoid is one of the main active ingredients in hawthorn, in which hyperoside content is higher. Xinxuening tablets, containing ursolic acid, vitexin rhamnoside, hyperoside, citric acid, and others, is a preparation made from hawthorn and pueraria and other traditional Chinese medicines, in which hawthorn enhances the actions of the medicine. Clinical indications of Xinxuening tablets are coronary heart disease, angina pectoris, chest tightness, palpitations, high blood pressure, arrhythmia, hyperlipidemia, and mental depression.

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 12 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: 87.0%

3-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-galactopyranosyl)-3',4',5,7-tetrahydroxyflavonol (161126-00-7) → Hyperoside (482-36-0)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 0.5h;

DOI:10.1021/acs.jnatprod.6b00274

Reference yield:

UDP-glucose (133-89-1) + quercetol (117-39-5,74893-81-5) → quercetin-3-O-glucoside (482-35-9,482-36-0,64052-89-7,65549-68-0,90327-16-5,112457-37-1)

Guidance literature:

With Glycine max (L_.) Merr_. cv. Clark His₆-UDP-glucose:flavonoid 3-O-glucosyltransferase; at 30 ℃; for 0.05h; pH=8; regiospecific reaction; aq. buffer;

DOI:10.1016/j.phytochem.2010.05.009

Reference yield:

UDP-glucose (133-89-1) + quercetol (117-39-5,74893-81-5) → quercetin-3-O-glucoside (482-35-9,482-36-0,64052-89-7,65549-68-0,90327-16-5,112457-37-1) + quercetin-3-O-D-glucoside-7-O-D-glucoside (6892-74-6,30311-60-5,56782-99-1,116004-33-2,125591-69-7)

Guidance literature:

With phosphate buffer; at 30 ℃; for 0.5h; Further Variations:; Reagents; Enzyme kinetics;

DOI:10.1016/j.phytochem.2006.06.026

upstream raw materials:

UDP-glucose

quercetol

quercetin-3-O-(2″-O-galloyl)-β-galactopyranoside

quercetin-3-O-(6-O-galloyl)-β-gallcopyranoside

Downstream raw materials:

D-Galactose

quercetol

hyperoside octaacetate

D-Galactose

Refernces

Studies on plants containing indole alkaloids. VIII. Indole alkaloid glycosides and other constituents of the leaves of Uncaria rhynchophylla Miq

10.1248/cpb.30.4046

This study investigated the glycosides and other polar components of Uncaria rhynchophylla, a plant used in traditional Chinese medicine. The researchers isolated a new glycoalkaloid named rhynchophylline (IV), which was identified as 6'-feruloylvinblastine lactam. They achieved a partial synthesis of rhynchophylline using vinblastine lactam as a starting material. In addition, they isolated five new compounds from the plant: valerine, vinblastine lactam, isofructoside, hyperoside, and trilobite. The study focused on the extraction and characterization of these compounds, using techniques such as UV spectroscopy, H-NMR, and 13C-NMR to elucidate their structures. These findings help understand the chemical composition of Uncaria rhynchophylla, which may have implications for its medicinal applications.

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