Quercetin

Base Information

• Chemical Name: Quercetin
• CAS No.: 117-39-5
• Deprecated CAS: 73123-10-1,74893-81-5,74893-81-5
• Molecular Formula: C15H10O7
• Molecular Weight: 302.24
• Hs Code.: 29329990
• European Community (EC) Number: 204-187-1
• NSC Number: 9219
• UN Number: 2811
• UNII: 9IKM0I5T1E
• DSSTox Substance ID: DTXSID4021218
• Nikkaji Number: J2.907F
• Wikipedia: Quercetin
• Wikidata: Q409478
• NCI Thesaurus Code: C792
• RXCUI: 9060
• Pharos Ligand ID: 5HV9TPVV1DM6
• Metabolomics Workbench ID: 23089
• ChEMBL ID: CHEMBL50
• Mol file: 117-39-5.mol

Synonyms:3,3',4',5,7-pentahydroxyflavone;dikvertin;Quercetin

Chemical Property of Quercetin

Chemical Property:

• Appearance/Colour: Yellow to green yellow crystalline powde
• Melting Point: 314-317 ºC
• Refractive Index: 1.4790 (estimate)
• Boiling Point: 642.4 ºC at 760 mmHg
• PKA: 6.31±0.40(Predicted)
• Flash Point: 248.1 ºC
• PSA: 131.36000
• Density: 1.799 g/cm³
• LogP: 1.98800
• Storage Temp.: Store at 0-5°C
• Solubility.: insoluble in H2O; ≥15.1 mg/mL in DMSO; ≥3.28 mg/mL in EtOH
• Water Solubility.: <0.1 g/100 mL at 21 oC
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 302.04265265
• Heavy Atom Count: 22
• Complexity: 488
• Transport DOT Label: Poison

Purity/Quality:

98% ^*data from raw suppliers

Quercetin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,Xi
• Hazard Codes: T,Xi
• Statements: 25-36/37/38
• Safety Statements: 45-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Herbal and Dietary Supplements
• Canonical SMILES: C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O)O
• Recent ClinicalTrials: Dasatinib Plus Quercetin for Accelerated Aging in Mental Disorders
• Recent NIPH Clinical Trials: The pharmacokinetic study of co-administration of polyphenols
• Uses: 1. It can be used as a kind of antioxidant which is mainly used for oil, drinks, cold drinks, meat processing products. 2. It has good effects of expectorant, anti-cough, anti-asthma and can be used for treating chronic bronchitis as well as for adjuvant therapy of coronary heart disease and high blood pressure. 3. It can also be used as analytical standards Medicine, reported formation of epoxy resins on mixing with epichlorohydrin. Quercetin has been used as an antioxidant which reversed the immunosuppressive effects of high glucose and hyperglycemic sera in type 2 diabetic patients.It has been used as a detoxifying phytochemical in Apis mellifera.It has been used as a positive control in DPPH (2,2- diphenyl-1-picryhydrazyl) radical scavenging assay. It has also been used for the preparation of calibration curve to determine total flavonoid content.
• Production method: 1. Crash the bark of trees in Fagaceae Quercus (Quercus) into powder, wash with hot brine, extract with dilute ammonia before neutralization with dilute sulfuric acid. Boil the filtrate and separate crystals. 2. It can be obtained by extracting Liliaceae onion (Alliumcepa) with 95% ethanol; it can also be produced from rutin (rutin) extract, quercetin, isoquercitrin, fennel glycosides, hyperoside, quercimeritrin, bloom glycosides through rutin degrading enzyme or hydrolysis with acidic aqueous solution.
• Description: The name of quercetin has been used since 1857, which is derived from quercetum (oak forest) after Quercus. Quercetin is widely found in flowers, leaves, and fruits of various plants. Vegetables (such as onions, ginger, celery, etc.), fruits (such as apples, strawberries, etc.), beverages (such as tea, coffee, red wine, fruit juice, etc.), and more than 100 kinds of Chinese herbal medicines (such as Threevein Aster, mountain white chrysanthemum, Huai rice, Apocynum, Ginkgo biloba, etc.) contain this ingredient. Threevein Aster is a Chinese herbal medicine and used in Jiangxi province, China, for more than 30 years. Its plant name is three veins Mala, Compositae. It is rich in drug sources, which can be found in Southern provinces of China. Clinical practice proved that it has significant anti-inflammatory and expectorant effects, and it is a good prescription for the treatment of elderly chronic bronchitis.
• Physical properties: Appearance: yellow needle-like crystalline powder. Solubility: slightly soluble in water; soluble in ethanol, acetone, pyridine, and acetic acid; easily soluble in ether and methanol. Melting point: 314–317 °C.
• Indications: It is mainly used for the treatment of chronic bronchitis.
• Clinical Use: Since the first clinical phase I trial of quercetin in 1996 found that it had antitumor activity, quercetin has also been reported in early clinical trials of cardiovascular disease, diabetes, and other diseases. However, there is still insufficient evidence shown that quercetin has a significant effect on the treatment of the disease in clinic.The US FDA has issued a warning, emphasizing that quercetin is not a definite nutrient, unable to determine its content in the diet, nor can it be used as a drug. China’s Threevein Aster consists of a single Chinese herb, which was released by the Pharmacopoeia of the People’s Republic of China (1977) Part I. One of the main active ingredients obtained following the hydrolysis of Threevein Aster is quercetin, which has the function of relieving cough and eliminating phlegm and can be used for the treatment of chronic bronchitis. The anti-inflammatory effect of Threevein Aster is poor. Side effects after use include stomach discomfort, dizziness, and abdominal pain, while withdrawal can make them disappear.

Technology Process of Quercetin

There total 187 articles about Quercetin 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: 47.0%

rutin (153-18-4) → L-Rhamnose (3615-41-6,478518-52-4) + D-glucose (50-99-7) + quercetol (117-39-5,74893-81-5)

Guidance literature:

With sulfuric acid; water;

DOI:10.1007/s10600-009-9287-0

Reference yield:

(2R,3S,4R)-(+)-3,4,5,7,3',4'-hexahydroxyflavan (69256-15-1) → cyanidin (13306-05-3) + quercetol (117-39-5,74893-81-5) + 2R,4R-flavan-3,3,4-triol + (-)-epitaxifolin (480-18-2,24198-97-8,98006-93-0,111003-33-9,114761-89-6,17654-26-1,5117-01-1) + taxifolin (480-18-2,17654-26-1,5117-01-1)

Guidance literature:

With anthocyanidin synthase from Vitis vinifera; water; In aq. acetate buffer; at 35 ℃; for 0.5h; pH=6.3; Mechanism; Enzymatic reaction;

DOI:10.1021/acs.jafc.8b06968

Reference yield:

rutin (153-18-4) → β-D-glucose (492-61-5) + L-rhamnose (6014-42-2) + quercetol (117-39-5,74893-81-5)

Guidance literature:

With Novosphingobium sp. PP₁Y protein extract; In aq. phosphate buffer; at 35 ℃; for 24h; pH=7; Enzymatic reaction;

DOI:10.1016/j.molcatb.2014.04.002

upstream raw materials:

tamarixetin

3,3'-di-O-methylquercetin

2-benzo[1,3]dioxol-5-yl-3-hydroxy-5,7-dimethoxy-chromen-4-one

rhamnetin

Downstream raw materials:

isoquercetin

6-C-α-L-arabinopyranosylquercetine

6-C-β-D-xylopyranosylquercetine

3,4-Dihydroxybenzoic acid

Refernces

• 1、 Pakudina,Sadykov. "-". . . Retrieved 1967.
• 2、 Zapesochnaya et al.. "-". . . Retrieved 1969.
• 3、 Wu, Chun,Wei, Chun-Shan,Yu, Shao-Fu,Liu, Bai-Lian,Li, Yao-Lan,Ye, Wen-Cai,Tong, Guang-Dong,Zhou, Guang-Xiong. "Two new acetylated flavonoid glycosides from Phyllanthus urinaria". . p. 703 - 707. Retrieved 2013.
• 4、 Bencheraiet, Reguia,Kabouche, Ahmed,Kabouche, Zahia,Touzani, Rachid,Jay, Maurice. "Flavonoids from physospermum acteaefolium". . p. 480 - 481. Retrieved 2012.
• 5、 Xiao,Wu,Wu,Shi,Hang,Aisa. "Kaempferol and quercetin flavonoids from Rosa rugosa". . p. 736 - 737. Retrieved 2006.
• 6、 Ozhanashiya,Glyzin. "-". . . Retrieved 1970.
• 7、 Pereya de Santiago,Juliani. "-". . p. 380. Retrieved 1972.
• 8、 Lee, Viola Szu-Yuan,Chen, Chiy-Rong,Liao, Yun-Wen,Tzen, Jason Tze-Cheng,Chang, Chi-I.. "Structural determination and DPPH radical-scavenging activity of two acylated flavonoid tetraglycosides in oolong tea (Camellia sinensis)". . p. 851 - 853. Retrieved 2008.
• 9、 Karni?ová Potocká, Elena,Mastihuba, Vladimír,Mastihubová, Mária. "Transrutinosylation of tyrosol by flower buds of Sophora japonica". . . Retrieved 2021.
• 10、 Sergeeva. "-". . . Retrieved 1974.