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QUERCETIN-3-O-GLUCURONIDE

Product Name
QUERCETIN-3-O-GLUCURONIDE
CAS No.
22688-79-5
Chemical Name
QUERCETIN-3-O-GLUCURONIDE
Synonyms
CS-149;Miquelianin;Mikwelianin;Quercituron;Querciturone;Miquelianin?, >99%;Quercetin 3-O-ßQuercetol glucuronide;Quercetol 3-glucuronide;Fampridine Impurity 188
CBNumber
CB51484947
Molecular Formula
C21H18O13
Formula Weight
478.36
MOL File
22688-79-5.mol
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QUERCETIN-3-O-GLUCURONIDE Property

Melting point:
193～195℃
Boiling point:
927.8±65.0 °C(Predicted)
Density 
1.96±0.1 g/cm3(Predicted)
storage temp. 
-20°C
solubility 
DMSO (Slightly), Methanol (Slightly)
form 
Solid
pka
2.76±0.70(Predicted)
color 
Yellow to Very Dark Yellow
Stability:
Very Hygroscopic
Major Application
metabolomics
vitamins, nutraceuticals, and natural products
InChIKey
DUBCCGAQYVUYEU-UVXHTARINA-N
SMILES
O([C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](C(=O)O)O1)O)C1C(C2=C(C=C(O)C=C2OC=1C1C=CC(O)=C(O)C=1)O)=O |&1:1,2,3,5,7,r|
LogP
2.100 (est)
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Safety

Safety Statements 
24/25
WGK Germany 
3
Storage Class
11 - Combustible Solids
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H314Causes severe skin burns and eye damage

H317May cause an allergic skin reaction

H370Causes damage to organs

H372Causes damage to organs through prolonged or repeated exposure

H373May cause damage to organs through prolonged or repeated exposure

H402Harmful to aquatic life

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P272Contaminated work clothing should not be allowed out of the workplace.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P333+P313IF SKIN irritation or rash occurs: Get medical advice/attention.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
00310590
Product name
Quercetin 3-glucuronide
Purity
primary pharmaceutical reference standard
Packaging
25mg
Price
$765
Updated
2025/07/31
Sigma-Aldrich
Product number
90733
Product name
Quercetin 3-glucuronide
Purity
analytical standard
Packaging
5mg
Price
$777
Updated
2022/05/15
Cayman Chemical
Product number
21289
Product name
Quercetin 3-O-glucuronide
Purity
≥98%
Packaging
1mg
Price
$49
Updated
2024/03/01
Cayman Chemical
Product number
21289
Product name
Quercetin 3-O-glucuronide
Purity
≥98%
Packaging
5mg
Price
$202
Updated
2024/03/01
Sigma-Aldrich
Product number
SMB00149
Product name
Quercetin 3-glucuronide
Purity
≥95% (LC/MS-ELSD)
Packaging
1mg
Price
$343
Updated
2025/07/31
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QUERCETIN-3-O-GLUCURONIDE Chemical Properties,Usage,Production

Description

Quercetin 3-O-glucuronide is a pharmacologically active flavonol glucuronide isolated from H. perforatum (St. John’s wort) that inhibits the α2c adrenergic receptor (Ki = 4,060 nM in hα2c preparations). Quercetin 3-O-glucuronide (0.6 mg/kg) reduced the time rats spent immobile in the forced swim test, suggesting antidepressant-like properties, when given either acutely or chronically. It also reduced open field stress-induced hyperthermia in mice (at 1.2 mg/kg).

Chemical Properties

Yellow Solid

Uses

Quercetin 3-O-β-D-Glucuronide is the major metabolite of Quercetin (Q509500).

Definition

ChEBI: Miquelianin is a quercetin O-glycoside that consists of quercetin attached to a beta-D-glucuronopyranosyl moiety at position 3 via a glycosidic linkage. Isolated from Salvia and Phaseolus vulgaris, it exhibits antioxidant and antidepressant activities. It has a role as a metabolite, an antioxidant and an antidepressant. It is a beta-D-glucosiduronic acid and a quercetin O-glycoside.

Synthesis

Overnight cultures of E. coli containing specific genes were inoculated into 50 mL of fresh LB medium containing appropriate antibiotics. Isopropyl -D-1-thiogalactopyranoside (IPTG) was added to the mixture to a final concentration of 1 mM. the transformants were incubated for an additional 20 h at 18C. The cells were then incubated with the antibiotic for a further 20 h. The transformants were then incubated with the antibiotic. Cells were harvested by centrifugation and resuspended in fresh M9 medium containing 2% glucose and antibiotics and 1 mM isopropyl -D-1-thiogalactopyranoside. The cell density was adjusted to an OD600 value of 2. A total reaction volume of 2 mL was maintained in a test tube (14 mm x 145 mm). one hundred micromoles of lignocaine was added to the reaction mixture. The mixture was incubated at 25C for 1.5 hrs. An additional 100 M lignocaine was added to the reaction mixture. The mixture was incubated for another 1.5 hours. 200 M lignocaine was added to the mixture to determine the optimal cell concentration. 2 hours later, another 200 M lignocaine was added to the mixture. The reaction mixture was incubated for 2 hours. The cell density was adjusted to an OD600 value of 3. 200 M quercetin was added to the reaction for 2 hours. One hundred micromoles of quercetin was added to the mixture. The mixture was shaken at 30C for 1.5 h to obtain 2-(3,4dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-3-yl-BETA-D-glucopyranosiduronic acid

in vivo

Miquelianin treatment, compared to vehicle-control treatment, significantly improves AD-type deficits in hippocampal formation basal synaptic transmission and long-term potentiation[3].

References

[1] A NAHRSTEDT  V B. Biologically active and other chemical constituents of the herb of Hypericum perforatum L.[J]. Pharmacopsychiatry, 1997, 30 Suppl 2: 129-134. DOI: 10.1055/s-2007-979533
[2] ADOLF NAHRSTEDT*  Veronika B. Lessons Learned from Herbal Medicinal Products: The Example of St. John’s Wort⊥[J]. Journal of Natural Products , 2010, 73 5: 1015-1021. DOI: 10.1021/np1000329
[3] V BUTTERWECK. Flavonoids from Hypericum perforatum show antidepressant activity in the forced swimming test.[J]. Planta medica, 2000, 66 1: 3-6. DOI: 10.1055/s-2000-11119
[4] OLIVER GRUNDMANN  Veronika B  Olaf Kelber. Effects of St. John’s wort extract and single constituents on stress-induced hyperthermia in mice.[J]. Planta medica, 2006, 72 15: 1366-1371. DOI: 10.1055/s-2006-951710

QUERCETIN-3-O-GLUCURONIDE Preparation Products And Raw materials

Raw materials

Preparation Products

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QUERCETIN-3-O-GLUCURONIDE Suppliers

Canada 1 China 169 France 3 India 3 United Kingdom 3 United States 11 USA 1 Global 191
Nanning Saifir Biotechnology Co., Ltd.
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18877121284
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1309367106@qq.com
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China
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Shanghai Standard Technology Co.,Ltd.
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021-021-57127007-6622-6622 17621252073
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+86 (21) 5132-0077
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luzh@nature-standard.com
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China
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Nanjing Yiming Pharmaceutical Technology Co., Ltd.
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19850700912
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13851286085@163.com
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China
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J & K SCIENTIFIC LTD.
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18210857532; 18210857532
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86-10-82849933
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jkinfo@jkchemical.com
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China
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Chemsky（shanghai）International Co.,Ltd.
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021-50135380
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shchemsky@sina.com
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China
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32321
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Shanghai Sphchem Co., Ltd.
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021-56491756 13512199871
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2819742715@qq.com
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China
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ShangHai YuanYe Biotechnology Co., Ltd.
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021-61312847 13636370518
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021-55068248
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shyysw007@163.com
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China
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Chengdu Biopurify Phytochemicals Ltd.
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+86-028-82633397 18982077548
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+86-28-82633165
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cwb1@biopurify.cn
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China
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Shanghai Winherb Medical Technology Co., Ltd.
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17301719108 13341702378
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QQ：190129269
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winherb@126.com
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China
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MedChemexpress LLC
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021-58955995
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609-228-5909
Email
sales@medchemexpress.cn
Country
United States
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4861
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View Lastest Price from QUERCETIN-3-O-GLUCURONIDE manufacturers

Shaanxi Dideu New Materials Co. Ltd
Product
QUERCETIN-3-O-GLUCURONIDE 22688-79-5
Price
US $0.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
1000kg
Release date
2025-09-28
Shanghai Standard Technology Co., Ltd.
Product
Quercetin-3-O-glucuronide 22688-79-5
Price
US $0.00/mg
Min. Order
20mg
Purity
≥98%(HPLC)
Supply Ability
100 g
Release date
2020-08-13

22688-79-5, QUERCETIN-3-O-GLUCURONIDERelated Search:

quercetin 3-sambubioside 2-(3,4-Dihydroxyphenyl)-8-(2-O-beta-L-galactopyranosyl-beta-D-glucopyranosyl)-5,7-dihydroxy-4H-1-Benzopyran-4-one MEDICAGOL Isofraxidin Quercetin-7-O-β-D-glucopyranoside 4',5-DIHYDROXY-7-METHOXYFLAVONE MOSLOFLAVONE hydroxygenkwanin Naringenin 7-O-β-D-Glucuronide (Mixture of Diastereomers) Naringenin GARDENIN B PONCIRIN Quercetin 3-O-neohesperidoside Resorcinol 3-(3,5-Di-tert-butyl-4-hydroxyphenyl)propionic acid Dihydrocaffeic acid Diphenylphosphine oxide Quercetagetin-7-O-glucoside

  • 3,3′,4′,5,7-Pentahydroxyflavone 3-glucuronide
  • Quercetol 3-O-glucuronide
  • Quercetol glucuronide
  • Quercetin 3-glucuronide ,>=99%
  • Quercetin 3-D-glucuronide
  • 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-3-yl β-D-Glucopyranosiduronic Acid
  • Mikwelianin
  • Miquelianin
  • Quercetin 3-O-β-D-Glucuronopyranoside
  • Quercituron
  • QUERCETIN-3-O-GLUCURONIDE(RG)
  • β-D-Glucopyranosiduronic acid, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-3-yl
  • 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-(β-D-glucopyranuronosyloxy)-4H-1-benzopyran-4-one
  • 3',4',5,7-Tetrahydroxyflavon-3-yl β-D-glucopyranosiduronic acid
  • Quercetin 3-O-β-D-glucuronide
  • Quercetol 3-glucuronide
  • Querciturone
  • 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-3-yl-beta-D-glucopyranosiduronic acid
  • Quercetin 3-glucuronide, 98%, from Bupleurum chinense DC.
  • QUERCETIN 3-O-GLUCURONIDE; QUERCETIN 3-GLUCURONIDE
  • Miquelianin?, >99%
  • Miquelianin (Quercetin 3-O-glucuronide)
  • CS-149
  • Quercetin 3-O-&szlig
  • b-D-Glucopyranosiduronic acid,2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-3-yl
  • Quercetin-β-O-β-D-Glucuronide
  • 3'-O-Methyl Quercetin 3-O-?-D-Glucuronide-d3
  • QUERCETIN-3-O-GLUCURONIDE
  • (2S,3S,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
  • Quercetin 3-glucuronide-RM
  • Fampridine Impurity 188
  • Miquelianin, 10 mM in DMSO
  • Quercetin 3-O-β-D-glucuronide
  • 22688-79-5
  • Miscellaneous Natural Products