Quercetin 3-rhamnoside - ≥98% , CAS No.522-12-3

CAS: 522-12-3 Cat. No.: Q1492857 Peso molecular: 448.38 Beilstein Registry Number: 68135 Número EC: 208-322-5 PubChem CID: 5280459

GRADE & PURITY ≥98%

Storage

Store at 2-8°C,Protected from light

Shipped In

Wet ice

Specifications

Especificaciones y pureza

≥98%

Condiciones de almacenamiento de almacenamiento

Store at 2-8°C, Protected from light

Enviado en

Wet ice

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Pureza

≥98%

Nombres e identificadores

• Sonrisas canónicas: CC1C(C(C(C(O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C=C4)O)O)O)O)O
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
• InChIKey: OXGUCUVFOIWWQJ-HQBVPOQASA-N
• INCHI: 1S/C21H20O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-18,21-26,28-29H,1H3/t7-,15-,17+,18+,21-/m0/s1
• Isómeros SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C=C4)O)O)O)O)O
• WGK Alemania: 3
• RTECS: UZ5950000
• PubChem CID: 5280459
• Peso molecular: 448.38
• Beilstein: 68135

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Clase Flavonoids
      • Subclass Flavonoid glycosides
        • Level5 Flavonoid O-glycosides
          • Level6 Flavonoid-3-O-glycosides

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Clase: 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 Oxacyclic compounds Polyols Acetals Hydrocarbon derivatives Organic oxides
• 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 - Pyranone - 1-hydroxy-4-unsubstituted benzenoid - Phenol - Monocyclic benzene moiety - Benzenoid - Pyran - Monosaccharide - Oxane - Vinylogous acid - Heteroaromatic compound - Secondary alcohol - Organoheterocyclic compound - Oxacycle - Polyol - Acetal - Organic oxide - Organic oxygen compound - Alcohol - Hydrocarbon derivative - Organooxygen compound - Aromatic heteropolycyclic compound
• Descripción: 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

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Propiedades químicas y físicas

• Sensibilidad: light sensitive
• Peso molecular: 448.400 g/mol
• XLogP3: 0.900
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 3
• Exact Mass: 448.101 Da
• Monoisotopic Mass: 448.101 Da
• Topological Polar Surface Area: 186.000 Ų
• Heavy Atom Count: 32
• Formal Charge: 0
• Complexity: 741.000
• 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

Referencias

1. Junjie Liu, Jingjing Liu, Yuxin Qiao, Hanxin Zhong, Jiaoxia Wei, Dongyang Han, Jin Peng, Yongzhou Feng, Danni Wang, Yujie Cheng, Haitao Lu, Li Yao.  (2025)  Rhodiola crenulata extract inhibits cell pyroptosis to ameliorate pulmonary vascular remodeling in rats through the regulation of decadienylcarnitine/NLRP3/GSDMD axis.  JOURNAL OF ETHNOPHARMACOLOGY,      [PMID:40850654] [10.1016/j.jep.2025.120439]

2. Siming Nie, Xiaofei Xie, Mengying Zhang, Mengfei Tian, Qi Liang, Chunjian Zhao, Chunying Li.  (2025)  Extracting phytochemicals from Eleutherococcus senticosus using natural low-melting mixtures: Experimental and molecular simulation.  JOURNAL OF FOOD COMPOSITION AND ANALYSIS,      [PMID:] [10.1016/j.jfca.2025.108318]

3. Yu Zhang, Haitian Fang, Tong Wang, Zhigang Zhang, Tianxiang Zhu, Lei Xiong, Haiming Hu, Hongtao Liu.  (2023)  Lactobacillus acidophilus-Fermented Jujube Juice Ameliorates Chronic Liver Injury in Mice via Inhibiting Apoptosis and Improving the Intestinal Microecology.  MOLECULAR NUTRITION & FOOD RESEARCH,      [PMID:38150643] [10.1002/mnfr.202300334]

4. Hao-Xiang Gao, Nan Chen, Qiang He, Bi Shi, Wei-Cai Zeng.  (2023)  Effects of structural characteristics of phenolic compounds on oxidation of glycerol trioleate: Action rule and mechanism.  FOOD CHEMISTRY,      [PMID:37688816] [10.1016/j.foodchem.2023.137361]

5. Linzi Li, Xueying Lei, Lin Chen, Ya Ma, Jun Luo, Xuebo Liu, Xinglian Xu, Guanghong Zhou, Xianchao Feng.  (2023)  Protective mechanism of quercetin compounds against acrylamide-induced hepatotoxicity.  Food Science and Human Wellness,      [PMID:] [10.26599/FSHW.2022.9250019]

6. Yuxi Wang, Bing Tan, Chi Chen, Xudong Zhang, Xiangjun Sun.  (2023)  The phenolic profile of walnut meal protein isolate and interaction of phenolics with walnut protein.  FOOD RESEARCH INTERNATIONAL,      [PMID:37316028] [10.1016/j.foodres.2023.113042]

7. 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,      [PMID:] [10.1016/j.fbio.2023.102508]

8. Min Fu, Lizhi Gao, Qin Geng, Ti Li, Taotao Dai, Chengmei Liu, Jun Chen.  (2023)  Noncovalent interaction mechanism and functional properties of flavonoid glycoside-β-lactoglobulin complexes.  Food & Function,  14  (3): (1357-1368).  [PMID:36648058] [10.1039/D2FO02791G]

9. Hongting Deng, Yuanju He, Hui Cao, Lei Chen, Hui Teng.  (2022)  New insight into the effect of hydroxyl substituted flavonoids on the cytotoxicity of 2-amino-3-methylimidazo[4,5-f]quinoline.  Food Frontiers,  4  (1): (289-296).  [PMID:] [10.1002/fft2.194]

10. 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).  [PMID:36264709] [10.1002/bmc.5536]

11. Jie Zhao, Lin Huang, Renjie Li, Zhuangwei Zhang, Jin Chen, Hongjin Tang.  (2022)  Insights from multi-spectroscopic analysis and molecular modeling to understand the structure–affinity relationship and the interaction mechanism of flavonoids with gliadin.  Food & Function,  13  (9): (5061-5074).  [PMID:35404372] [10.1039/D1FO03816H]

12. Ying Li, Haiming Hu, Huabing Yang, Aizhen Lin, Hui Xia, Xue Cheng, Mingwang Kong, Hongtao Liu.  (2022)  Vine Tea (Ampelopsis grossedentata) Extract Attenuates CCl4-Induced Liver Injury by Restoring Gut Microbiota Dysbiosis in Mice.  MOLECULAR NUTRITION & FOOD RESEARCH,  66  (9): (2100892).  [PMID:35188709] [10.1002/mnfr.202100892]

13. Jian Gao, Bingbing Cheng, Yufeng Liu, Meng M. Li, Guangyong Zhao.  (2021)  Dietary supplementation with red cabbage extract rich in anthocyanins increases urinary hippuric acid excretion and consequently decreases nitrous oxide emissions in beef bulls.  ANIMAL FEED SCIENCE AND TECHNOLOGY,      [PMID:] [10.1016/j.anifeedsci.2021.115075]

14. Di Wu, Ran Duan, Lan Tang, Xia Hu, Fang Geng, Qiaomei Sun, Yin Zhang, Hui Li.  (2021)  Binding mechanism and functional evaluation of quercetin 3-rhamnoside on lipase.  FOOD CHEMISTRY,      [PMID:33945987] [10.1016/j.foodchem.2021.129960]

15. Chaonan Su, Caihong Li, Kang Sun, Wenjing Li, Rongxia Liu.  (2020)  Quantitative analysis of bioactive components in walnut leaves by UHPLC-Q-Orbitrap HRMS combined with QAMS.  FOOD CHEMISTRY,      [PMID:32544651] [10.1016/j.foodchem.2020.127180]

16. Hongjin Tang, Lin Huang, Dongsheng Zhao, Chunyong Sun, Ping Song.  (2020)  Interaction mechanism of flavonoids on bovine serum albumin: Insights from molecular property-binding affinity relationship.  SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY,      [PMID:32480277] [10.1016/j.saa.2020.118519]

17. Ruocong Yang, Hao Liu, Chen Bai, Yingchao Wang, Xiaohui Zhang, Rui Guo, Siying Wu, Jianxun Wang, Elaine Leung, Hang Chang, Peng Li, Tiegang Liu, Yi Wang.  (2020)  Chemical composition and pharmacological mechanism of Qingfei Paidu Decoction and Ma Xing Shi Gan Decoction against Coronavirus Disease 2019 (COVID-19): In silico and experimental study.  PHARMACOLOGICAL RESEARCH,      [PMID:32360484] [10.1016/j.phrs.2020.104820]

18. Jie Zhao, Lin Huang, Chunyong Sun, Dongsheng Zhao, Hongjin Tang.  (2020)  Studies on the structure-activity relationship and interaction mechanism of flavonoids and xanthine oxidase through enzyme kinetics, spectroscopy methods and molecular simulations.  FOOD CHEMISTRY,      [PMID:32330646] [10.1016/j.foodchem.2020.126807]

19. Yan Dong, Jun Yang, Liyuan Yang, Ping Li.  (2020)  Quercetin Inhibits the Proliferation and Metastasis of Human Non-Small Cell Lung Cancer Cell Line: The Key Role of Src-Mediated Fibroblast Growth Factor-Inducible 14 (Fn14)/Nuclear Factor kappa B (NF-κB) pathway.  MEDICAL SCIENCE MONITOR,      [PMID:32225128] [10.12659/MSM.920537]

20. Rongxia Liu, Chaonan Su, Yumeng Xu, Kangle Shang, Kang Sun, Caihong Li, Jing Lu.  (2020)  Identifying potential active components of walnut leaf that action diabetes mellitus through integration of UHPLC-Q-Orbitrap HRMS and network pharmacology analysis.  JOURNAL OF ETHNOPHARMACOLOGY,      [PMID:32058009] [10.1016/j.jep.2020.112659]

21. 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).  [PMID:31510022] [10.3390/ma12182923]

22. Chen Haiming, Liu Huazhen, Lu Chuanjian, Wang Maojie, Li Xiong, Zhao Hui, Yan Yuhong, Yu Wanling, Han Ling, Dai Zhenhua.  (2018)  PSORI-CM02 Formula Increases CD4+ Foxp3+ Regulatory T Cell Frequency and Ameliorates Imiquimod-Induced Psoriasis in Mice.  Frontiers in Immunology,      [PMID:29358932] [10.3389/fimmu.2017.01767]

23. Guan-Lin Chen, Song-Gen Chen, Yi Xiao, Nan-Lin Fu.  (2017)  Antioxidant capacities and total phenolic contents of 30 flowers.  INDUSTRIAL CROPS AND PRODUCTS,      [PMID:] [10.1016/j.indcrop.2017.10.051]

24. 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,      [PMID:] [10.1016/j.jff.2017.01.011]

25. Wang Huaqian, Li Dongli, Du Zhiyun, Huang Mou-Tuan, Cui Xiaoxing, Lu Yujing, Li Chenyue, Woo Swee Lian, Conney Allan H., Zheng Xi, Zhang Kun.  (2015)  Antioxidant and anti-inflammatory properties of Chinese ilicifolius vegetable (Acanthopanax trifoliatus (L) Merr) and its reference compounds.  FOOD SCIENCE AND BIOTECHNOLOGY,  24  (3): (1131-1138).  [PMID:] [10.1007/s10068-015-0144-6]

26. Miao He, Zhezhi Wang.  (2013)  Genetic diversity of Hypericum perforatum collected from the Qinling Mountains of China.  BIOCHEMICAL SYSTEMATICS AND ECOLOGY,      [PMID:] [10.1016/j.bse.2013.03.051]

27. Shengming Zhao, Liu Yang, Mengran Hei, Yanan Zhao, Mingming Zhu, Hui Wang, Haixu Zhou, Hanjun Ma.  (2024)  Conformation and functional modification of porcine myofibrillar protein by pepper leaf polyphenols under oxidative condition.  LWT-FOOD SCIENCE AND TECHNOLOGY,      [PMID:] [10.1016/j.lwt.2024.116017]

28. Yue Li, Hongmei Liu, Sikai Wang, Wei Fang, Xinxin Jiang, Guoqi Zhang, Yan Zhao.  (2024)  Fast screening of α-glucosidase inhibitors from Ginkgo biloba leaf by using α-glucosidase immobilized on magnetic metal-organic framework.  JOURNAL OF SEPARATION SCIENCE,  47  (14): (2400342).  [PMID:39031453] [10.1002/jssc.202400342]

29. Jingyu Wang, Lei Zhou, Lujuan Xing, Guanghong Zhou, Wangang Zhang.  (2024)  Mechanism of Toona sinensis seed polyphenols inhibiting oxidation and modifying physicochemical and gel properties of pork myofibrillar protein under oxidation system.  FOOD CHEMISTRY,      [PMID:39432947] [10.1016/j.foodchem.2024.141666]

30. Huan Fang, Tong Wang, Lan Chen, Xiao-Zhi Wang, Hai-Long Wu, Yao Chen, Ru-Qin Yu.  (2024)  Rapid authenticity identification of high-quality Wuyi Rock tea by multidimensional fluorescence spectroscopy coupled with chemometrics.  JOURNAL OF FOOD COMPOSITION AND ANALYSIS,      [PMID:] [10.1016/j.jfca.2024.106632]

31. Xijin Yang, Ying Li, Qiju Shao, Zhirong Li, Zeli Chun, Yan Wang, Yaping Zhou, Rongxiang Chen.  (2024)  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,      [PMID:39579741] [10.1016/j.jchromb.2024.124387]

32. Hanli Guo, Weifeng Yin, Ziling Zou, Chao Zhang, Minghui Sun, Lingtian Min, Lei Yang, Lingyi Kong.  (2020)  Quercitrin alleviates cartilage extracellular matrix degradation and delays ACLT rat osteoarthritis development: An in vivo and in vitro study.  Journal of Advanced Research,      [PMID:33364061] [10.1016/j.jare.2020.06.020]

33. Yu Meng, Wenhao Zou, Tingting Guo, Lin Zhang, Pengpai Zhang, Penghua Shu.  (2025)  Optimization of ultrasound-assisted deep eutectic solvent extraction, characterization, and bioactivities of flavonoids from Cercis glabra leaves.  ULTRASONICS SONOCHEMISTRY,      [PMID:40543485] [10.1016/j.ultsonch.2025.107434]

34. Jiafei Qian, Wenwen You, Yicheng Wang, Yunlin Cao, Xiaoyong Zhao, Hongxia Xu, Hang Ge, Xiaoying Li, Di Wu, Junwei Chen, Xian Li.  (2025)  Transcription factor EjMYBF1 positively regulates flavonol biosynthesis in loquat (Eriobotrya japonica).  PLANT PHYSIOLOGY AND BIOCHEMISTRY,      [PMID:41106234] [10.1016/j.plaphy.2025.110633]

35. Tianze Xin, Yuqing Xu, Bixian Han, Zuoqing Li, Quansheng Liu, Hanxiang Li, Bingqiang Xu.  (2026)  Chemophenetic characterization of Pleuropterus multiflorus and Pleuropterus angulatus based on UPLC-MS/MS and molecular networking.  BIOCHEMICAL SYSTEMATICS AND ECOLOGY,      [PMID:] [10.1016/j.bse.2026.105238]