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482-35-9 , Hirsutrin ,Isoquercetin, CAS:482-35-9

482-35-9, Hirsutrin ,
Isoquercetin,
CAS:482-35-9
C21H20O12 / 464.38
MFCD00017746

陆地棉苷, Hirsutrin , Isoquercetin

Quercetin 3-b-D-glucopyranoside

Mitochondrial ATPase and phosphodiesterase inhibitor.

Isoquercetin is a type of flavonoid compound naturally found in various fruits and vegetables, such as apples, onions, and red grapes. It has been shown to possess a wide range of biological activities, including antioxidant, anti-inflammatory, and antimicrobial effects. Isoquercetin has been used extensively in scientific research, and it has shown promising results in various fields, including biomedicine, agriculture, and food technology.

Definition and Background:

Isoquercetin, also known as quercetin-3-glucoside, is a flavonoid glycoside belonging to the group of flavonoids called flavonols. It is structurally similar to quercetin, another flavonoid, with the difference being that isoquercetin has a glucose molecule attached to it. Isoquercetin has been extensively studied for its health benefits, and it has been found to possess potent antioxidant and anti-inflammatory properties.

Physical and Chemical Properties:

Isoquercetin is a yellow crystalline powder with a bitter taste. Its molecular formula is C21H20O12, and its molecular weight is 464.38 g/mol. Isoquercetin is a water-soluble compound, and it has a melting point of 376-377°C. Its solubility in water is 1.5% (w/v) at 25°C.

Synthesis and Characterization:

Isoquercetin can be synthesized using various methods, including enzymatic, chemical, and microbial synthesis. Enzymatic synthesis involves the use of enzymes, such as glucosyltransferases, to transfer a glucose molecule to quercetin, forming isoquercetin. Chemical synthesis involves the use of chemical reagents, such as glucosyl donors, to synthesize isoquercetin. Microbial synthesis involves the use of microorganisms, such as Escherichia coli, to produce isoquercetin. The synthesized isoquercetin can be characterized using various analytical methods, such as HPLC, NMR, and IR spectroscopy.

Analytical Methods:

Isoquercetin can be quantified using various analytical methods, such as HPLC, LC-MS, and UV spectroscopy. HPLC is the most commonly used method for the analysis of isoquercetin due to its high sensitivity and selectivity. LC-MS provides additional information on the structure of isoquercetin, and UV spectroscopy is used to quantify isoquercetin in plant extracts.

Biological Properties:

Isoquercetin has been shown to possess a wide range of biological activities, including antioxidant, anti-inflammatory, and antimicrobial effects. It has been found to scavenge free radicals, protect against oxidative damage, inhibit inflammation, and prevent the growth of bacteria and fungi. Isoquercetin has also been shown to modulate various cell signaling pathways and gene expression, affecting cell proliferation, differentiation, and apoptosis.

Toxicity and Safety in Scientific Experiments:

Isoquercetin has been extensively studied for its toxicity and safety in scientific experiments. It has been found to be generally safe, with a low toxicity profile. Studies have shown that isoquercetin does not cause significant toxicity or adverse effects, even at high doses. However, some studies have reported mild side effects, such as gastrointestinal discomfort, in certain individuals.

Applications in Scientific Experiments:

Isoquercetin has been used extensively in scientific research, and it has shown promising results in various fields, including biomedicine, agriculture, and food technology. In biomedicine, isoquercetin has been studied for its potential use in the treatment of various diseases, such as cancer, diabetes, and neurodegenerative disorders. In agriculture, isoquercetin has been studied for its potential use as a natural pesticide, and in food technology, it has been studied for its potential use as a natural food preservative.

Current State of Research:

The current state of research on isoquercetin is highly promising, with numerous studies demonstrating its potential applications in various fields. Isoquercetin has been found to possess potent antioxidant, anti-inflammatory, and antimicrobial properties, making it a promising natural compound for use in the prevention and treatment of various diseases. However, further research is needed to explore its full therapeutic potential and mechanism of action.

Potential Implications in Various Fields of Research and Industry:

Isoquercetin has potential implications in various fields of research and industry, including biomedicine, agriculture, and food technology. In biomedicine, isoquercetin has the potential to become a safe and effective natural therapeutic agent for the treatment of various diseases. In agriculture, isoquercetin has the potential to become a natural alternative to synthetic pesticides, thereby reducing environmental pollution and promoting sustainable agriculture. In food technology, isoquercetin has the potential to become a natural additive for the preservation of food products, thus reducing the need for synthetic preservatives.

Limitations and Future Directions:

Despite the promising results of isoquercetin in various studies, there are still some limitations and future directions that need to be addressed. First, the mechanisms of action of isoquercetin need to be fully understood in order to optimize its therapeutic potential. Second, the safety and efficacy of isoquercetin need to be investigated further in clinical studies. Third, the synthesis of isoquercetin needs to be optimized to ensure its scalability and cost-effectiveness. Fourth, the potential interactions of isoquercetin with other drugs need to be studied further to ensure its safe use. Finally, the potential applications of isoquercetin in other fields, such as cosmetics and environmental remediation, need to be explored further.

CAS Number482-35-9
Product NameIsoquercetin
IUPAC Name2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Molecular FormulaC21H20O12
Molecular Weight464.38 g/mol
InChIInChI=1S/C21H20O12/c22-6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-18,21-27,29-30H,6H2/t13-,15-,17+,18-,21?/m1/s1
InChI KeyOVSQVDMCBVZWGM-CAWYGJOUSA-N
SMILESC1=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
SolubilityREADILY SOL IN WATER
Insol in alc. Sol in glycerol and in propylene glycol, but prolonged heating (several days) may be necessary for complete soln (about 5%)
Almost completely sol in twice its weight of water.
INSOL IN MOST ORGANIC SOLVENTS
Completely soluble in hot and cold water; yielding a viscous solution of mucilage; insoluble in alcohol.
Synonyms2-(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
Canonical SMILESC1=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
Isomeric SMILESC1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O


CAS No: 21637-25-2,482-35-9 Synonyms: IsoquercitrinQuercetin 3-b-D-glucoside MDL No: MFCD00017746 Chemical Formula: C21H20O12 Molecular Weight: 464.38


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