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| Synonyms | Isoquercetin | Isoquercitrin | 482-35-9 | Hirsutrin | 3-Glucosylquercetin | Quercetin 3-glucoside | Quercetin 3-o-glucopyranoside | Quercetin 3-D-glucoside | Quercetol 3-monoglucoside | Quercetin 3-O-glucoside | Quercetol 3-glucoside | CONTIGOSIDE B | Isotrifoliin | quercetin-3-O- |
|---|---|
| Specifications & Purity | 10mM in DMSO |
| Storage Temp | Store at -80°C |
| Shipped In |
Ice chest + Ice pads This product requires cold chain shipping. Ground and other economy services are not available. |
| Product Description |
Quercetin 3-β-D-glucoside can be used to study cell biology, bioactive small molecules, biochemicals found in plants and nutrition. Quercetin-3-β-d-glucoside?, a glucoside form of quercetin, significantly reduced the replication of influenza viruses in vitro and in vivo. Quercetin-3-β-d-glucoside has been used in a study to compare the anti-proliferative activities of quercetin derivatives using six different cancer cell lines (colon, breast, hepatocellular and lung cancer). |
Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Phenylpropanoids and polyketides |
| Class | Flavonoids |
| Subclass | Flavonoid glycosides |
| Intermediate Tree Nodes | Flavonoid O-glycosides |
| Direct Parent | Flavonoid-3-O-glycosides |
| Alternative Parents | 3'-hydroxyflavonoids 4'-hydroxyflavonoids 5-hydroxyflavonoids 7-hydroxyflavonoids Flavones Hexoses O-glycosyl compounds Chromones Catechols 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Pyranones and derivatives Oxanes Benzene and substituted derivatives Vinylogous acids Heteroaromatic compounds Secondary alcohols Acetals Oxacyclic compounds Polyols Organic oxides Primary alcohols Hydrocarbon derivatives |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Flavonoid-3-o-glycoside - Hydroxyflavonoid - 3'-hydroxyflavonoid - 4'-hydroxyflavonoid - 5-hydroxyflavonoid - 7-hydroxyflavonoid - Flavone - Hexose monosaccharide - Chromone - Glycosyl compound - O-glycosyl compound - Benzopyran - 1-benzopyran - Catechol - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Pyranone - 1-hydroxy-4-unsubstituted benzenoid - Monocyclic benzene moiety - Benzenoid - Pyran - Monosaccharide - Oxane - Vinylogous acid - Heteroaromatic compound - Secondary alcohol - Organoheterocyclic compound - Oxacycle - Polyol - Acetal - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Alcohol - Primary alcohol - Organooxygen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. |
| External Descriptors | flavonols - Flavones and Flavonols |
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| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
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| IUPAC 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 |
|---|---|
| INCHI | InChI=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 |
| InChIKey | OVSQVDMCBVZWGM-QSOFNFLRSA-N |
| 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 |
| Isomeric SMILES | C1=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 |
| Alternate CAS | 21637-25-2 |
| PubChem CID | 5280804 |
| Molecular Weight | 464.38 |
| Beilstein | 100989 |
| Molecular Weight | 464.400 g/mol |
|---|---|
| XLogP3 | 0.400 |
| Hydrogen Bond Donor Count | 8 |
| Hydrogen Bond Acceptor Count | 12 |
| Rotatable Bond Count | 4 |
| Exact Mass | 464.095 Da |
| Monoisotopic Mass | 464.095 Da |
| Topological Polar Surface Area | 207.000 Ų |
| Heavy Atom Count | 33 |
| Formal Charge | 0 |
| Complexity | 758.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 5 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |
| 1. Tian Yang, Zhong Zhang, Fangjian Ning, Li Yuan, Xingbin Yang, Liping Luo. (2024) New theoretical perspective for easy evaluation of the antioxidant properties of typical flavonoids. MICROCHEMICAL JOURNAL, 197 (109786). |
| 2. Guanghe Zhao, Ruifen Zhang, Lihong Dong, Mei Deng, Yanxia Chen, Mingwei Zhang. (2023) The effects of different enzymes on the liberation of bound phenolics from rice bran dietary fibre and their antioxidant activities. Food Bioscience, 56 (103449). |
| 3. Linzi Li, Xueying Lei, Lin Chen, Ya Ma, Jun Luo, Xuebo Liu, Xinglian Xu, Guanghong Zhou, Xianchao Feng. (2024) Protective mechanism of quercetin compounds against acrylamide-induced hepatotoxicity. Food Science and Human Wellness, 13 (225). |
| 4. Huiqun Fan, Mingshun Chen, Taotao Dai, Lizhen Deng, Chengmei Liu, Wei Zhou, Jun Chen. (2023) Phenolic compounds profile of Amomum tsaoko Crevost et Lemaire and their antioxidant and hypoglycemic potential. Food Bioscience, 52 (102508). |
| 5. Qi Dong, Na Hu, Huilan Yue, Honglun Wang, Yue Wei. (2022) Rapid screening of α-glucosidase inhibitors in Hypericum perforatum L. using bio-affinity chromatography coupled with UPLC/MS. BIOMEDICAL CHROMATOGRAPHY, 37 (2): (e5536). |
| 6. Guanghe Zhao, Ruifen Zhang, Lihong Dong, Lei Liu, Fei Huang, Xuchao Jia, Mei Deng, Jianwei Chi, Yongxuan Ma, Yanxia Chen, Qin Ma, Mingwei Zhang. (2022) Bound phenolics in rice bran dietary fibre released by different chemical hydrolysis methods: content, composition and antioxidant activities. INTERNATIONAL JOURNAL OF FOOD SCIENCE AND TECHNOLOGY, 57 (9): (5909-5916). |
| 7. Ye Hangyu, Li Xiaojun, Li Luyuan, Zhang Yinjun, Zheng Jianyong. (2022) Homologous Expression and Characterization of α-L-rhamnosidase from Aspergillus niger for the Transformation of Flavonoids. APPLIED BIOCHEMISTRY AND BIOTECHNOLOGY, 194 (8): (3453-3467). |
| 8. Qi-rui Hu, Peng-wei Lai, Fang Chen, Yan-fang Yu, Bing Zhang, Hongyan Li, Rong Liu, Yawei Fan, Ze-yuan Deng. (2022) Whole mulberry leaves as a promising functional food: From the alteration of phenolic compounds during spray drying and in vitro digestion. JOURNAL OF FOOD SCIENCE, 87 (3): (1230-1243). |
| 9. Shuai Zhang, Qin Ma, Lihong Dong, Xuchao Jia, Lei Liu, Fei Huang, Guang Liu, Zhida Sun, Jianwei Chi, Mingwei Zhang, Ruifen Zhang. (2022) Phenolic profiles and bioactivities of different milling fractions of rice bran from black rice. FOOD CHEMISTRY, 378 (132035). |
| 10. Wenhui Zhang, Xican Li, Yujie Hua, Zhen Li, Ban Chen, Aijun Liu, Wenbiao Lu, Xiaojun Zhao, Yuanming Diao, Dongfeng Chen. (2021) Antioxidant product analysis of Hulu Tea (Tadehagi triquetrum). NEW JOURNAL OF CHEMISTRY, 45 (43): (20257-20265). |
| 11. Li Jun Li, Xiao Qing Liu, Xi Ping Du, Ling Wu, Ze Dong Jiang, Hui Ni, Qing Biao Li, Feng Chen. (2020) Preparation of isoquercitrin by biotransformation of rutin using α-L-rhamnosidase from Aspergillus niger JMU-TS528 and HSCCC purification. PREPARATIVE BIOCHEMISTRY & BIOTECHNOLOGY, |
| 12. Yuhuan Chen, Qiwen Chen, Xiaozhong Wang, Fan Sun, Yawei Fan, Xiaoru Liu, Hongyan Li, Zeyuan Deng. (2020) Hemostatic action of lotus leaf charcoal is probably due to transformation of flavonol aglycons from flavonol glycosides in traditional Chinses medicine. JOURNAL OF ETHNOPHARMACOLOGY, 249 (112364). |
| 13. You Luo, Haiqing Liu, Shanzhong Yang, Jiarui Zeng, Zhenqiang Wu. (2019) Sodium Alginate-Based Green Packaging Films Functionalized by Guava Leaf Extracts and Their Bioactivities. Materials, 12 (18): (2923). |
| 14. Yanhua Tu, Beixuan He, Songyan Gao, Dandan Guo, Xinlei Jia, Xin Dong, Meili Guo. (2019) CtACO1 Overexpression Resulted in the Alteration of the Flavonoids Profile of Safflower. MOLECULES, 24 (6): (1128). |
| 15. Lei Zhang, Shi-Tao Zhang, Yan-Chun Yin, Shu Xing, Wan-Nan Li, Xue-Qi Fu. (2018) Hypoglycemic effect and mechanism of isoquercitrin as an inhibitor of dipeptidyl peptidase-4 in type 2 diabetic mice. RSC Advances, 8 (27): (14967-14974). |
| 16. Guan-Lin Chen, Song-Gen Chen, Yi Xiao, Nan-Lin Fu. (2018) Antioxidant capacities and total phenolic contents of 30 flowers. INDUSTRIAL CROPS AND PRODUCTS, 111 (430). |
| 17. Guan-Lin Chen, Xin Zhang, Song-Gen Chen, Men-Di Han, Yong-Qing Gao. (2017) Antioxidant activities and contents of free, esterified and insoluble-bound phenolics in 14 subtropical fruit leaves collected from the south of China. Journal of Functional Foods, 30 (290). |
| 18. Shuzhen Yang, Jie Zhou, Dongmei Li, Chunyu Shang, Litao Peng, Siyi Pan. (2017) The structure-antifungal activity relationship of 5,7-dihydroxyflavonoids against Penicillium italicum. FOOD CHEMISTRY, 224 (26). |
| 19. HanLiang Guan, Dawei Qian, Hao Ren, Wei Zhang, Hui Nie, Erxing Shang, Jinao Duan. (2014) Interactions of pharmacokinetic profile of different parts from Ginkgo biloba extract in rats. JOURNAL OF ETHNOPHARMACOLOGY, 155 (758). |
| 20. Linling Lu, Dawei Qian, Jianming Guo, Yefei Qian, Boyi Xu, Mei Sha, Jinao Duan. (2013) Abelmoschi Corolla non-flavonoid components altered the pharmacokinetic profile of its flavonoids in rat. JOURNAL OF ETHNOPHARMACOLOGY, 148 (804). |
| 21. Linling Lu, Dawei Qian, Jing Yang, Shu Jiang, Jianming Guo, Er-xin Shang, Jin-ao Duan. (2012) Identification of isoquercitrin metabolites produced by human intestinal bacteria using UPLC-Q-TOF/MS. BIOMEDICAL CHROMATOGRAPHY, 27 (4): (509-514). |
| 22. Xijin Yang, Ying Li, Qiju Shao, Zhirong Li, Zeli Chun, Yan Wang, Yaping Zhou, Rongxiang Chen. (2025) Screening, fingerprinting, and identification of phenolic antioxidants in Persicaria chinensis (L.) H. Gross by liquid chromatography – electrochemical detection and liquid chromatography – tandem mass spectrometry. JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES, 1250 (124387). |