Determine the necessary mass, volume, or concentration for preparing a solution.
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Moligand™, analytical standard, ≥99% Analytical standard,Moligand™ for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Protected from light,Argon charged,Room temperature Ships Normal Check lot-specific COA for exact specifications.
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 31 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
| Canonical Smiles | C1=CC=C(C=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O |
|---|---|
| IUPAC Name | 3,5,7-trihydroxy-2-phenylchromen-4-one |
| InChIKey | VCCRNZQBSJXYJD-UHFFFAOYSA-N |
| INCHI | 1S/C15H10O5/c16-9-6-10(17)12-11(7-9)20-15(14(19)13(12)18)8-4-2-1-3-5-8/h1-7,16-17,19H |
| Isomeric SMILES | C1=CC=C(C=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O |
| WGK Germany | 3 |
| RTECS | LK9275500 |
| Molecular Weight | 270.24 |
| Beilstein | 272179 |
| Reaxy-Rn | 272179 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=272179&ln= |
Comprehensive hazard, handling, storage, and regulatory compliance document.
Download SDS →Lot-specific quality data. Enter your lot number to retrieve the exact COA.
Look up COA →Full quality attributes and acceptance criteria for this grade.
View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Phenylpropanoids and polyketides |
| Class | Flavonoids |
| Subclass | Flavones |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Flavonols |
| Alternative Parents | 7-hydroxyflavonoids 5-hydroxyflavonoids 3-hydroxyflavonoids Chromones Pyranones and derivatives 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Benzene and substituted derivatives Vinylogous acids Heteroaromatic compounds Polyols Oxacyclic compounds Organic oxides Hydrocarbon derivatives |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | 3-hydroxyflavone - 3-hydroxyflavonoid - 5-hydroxyflavonoid - 7-hydroxyflavonoid - Hydroxyflavonoid - Chromone - Benzopyran - 1-benzopyran - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Pyranone - Monocyclic benzene moiety - Benzenoid - Pyran - Vinylogous acid - Heteroaromatic compound - Organoheterocyclic compound - Oxacycle - Polyol - Organooxygen compound - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as flavonols. These are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. |
| External Descriptors | Flavones and Flavonols |
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| Sensitivity | Light sensitive;Air sensitive |
|---|---|
| Melt Point(°C) | 218-228℃ |
| Molecular Weight | 270.240 g/mol |
| XLogP3 | 2.300 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 1 |
| Exact Mass | 270.053 Da |
| Monoisotopic Mass | 270.053 Da |
| Topological Polar Surface Area | 87.000 Ų |
| Heavy Atom Count | 20 |
| Formal Charge | 0 |
| Complexity | 424.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| 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. Zheyuan Ren, Yang Yu, Zhongyao Ji, Huitao Li, Xiaoheng Li, Han Lin, Renshan Ge, Qiqi Zhu. (2023) Structure-activity relationship and docking analysis of nature flavonoids as inhibitors of human and rat gonadal 3β-hydroxysteroid dehydrogenases for therapeutic purposes. JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY, [PMID:38143010] [10.1016/j.jsbmb.2023.106450] |
| 2. Xiangrong Li, Ruonan Xu, Li Shi, Tianjun Ni. (2023) Design of flavonol-loaded cationic gold nanoparticles with enhanced antioxidant and antibacterial activities and their interaction with proteins. INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, [PMID:37769767] [10.1016/j.ijbiomac.2023.127074] |
| 3. Xiangrong Li, Tianjun Ni, Ruonan Xu. (2023) Study on the preparation of novel flavonol-gold nanoparticles antioxidants and the mechanism of protein corona formation. JOURNAL OF MOLECULAR STRUCTURE, [PMID:] [10.1016/j.molstruc.2023.136413] |
| 4. Shaoyan Zhang, Jinfeng Ning, Qingqing Wang, Wei Wang. (2023) Fluorescence enhancement of flavonoids and its application in ingredient determination for some traditional Chinese medicines by CE-LIF. Analytical Methods, 15 (24): (2964-2970). [PMID:37309583] [10.1039/D3AY00486D] |
| 5. Xiangrong Li, Ruonan Xu, Tianjun Ni. (2023) Effects of B-ring structures on binding behavior of flavonols with proteins: Experimental and molecular docking approaches. JOURNAL OF MOLECULAR STRUCTURE, [PMID:] [10.1016/j.molstruc.2023.135614] |
| 6. Chun Xiao Li, Fu Rong Wang, Bing Zhang, Ze Yuan Deng, Hong Yan Li. (2023) Stability and antioxidant activity of phenolic compounds during in vitro digestion. JOURNAL OF FOOD SCIENCE, 88 (2): (696-716). [PMID:36617678] [10.1111/1750-3841.16440] |
| 7. 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] |
| 8. Xijuan Tu, Fengjie Yu, Qian Jin, Chunping Du, Jiaxu Chen, Ji Yang, Yuchang He, Shaokang Huang, Wenbin Chen. (2022) A Simple High-Throughput Field Sample Preparation Method Based on Matrix-Induced Sugaring-Out for the Simultaneous Determination of 5-Hydroxymethylfurfural and Phenolic Compounds in Honey. MOLECULES, 27 (23): (8373). [PMID:36500464] [10.3390/molecules27238373] |
| 9. Xiangrong Li, Linyu Han, Zhizhi Song, Ruonan Xu, Lixia Wang. (2022) Comparative study on the interaction between transferrin and flavonols: Experimental and computational modeling approaches. SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, [PMID:36455462] [10.1016/j.saa.2022.122128] |
| 10. 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] |
| 11. Jie Zhao, Lin Huang, Renjie Li, Zhuangwei Zhang, Jin Chen, Hongjin Tang. (2022) Multispectroscopic and computational evaluation of the binding of flavonoids with bovine serum albumin in the presence of Cu2+. FOOD CHEMISTRY, [PMID:35279499] [10.1016/j.foodchem.2022.132656] |
| 12. Yajing Fang, Fuqiang Liang, Mengmeng Xia, Weiwei Cao, Siyi Pan, Ting Wu, Xiaoyun Xu. (2021) Structure-activity relationship and mechanism of flavonoids on the inhibitory activity of P-glycoprotein (P-gp)-mediated transport of rhodamine123 and daunorubicin in P-gp overexpressed human mouth epidermal carcinoma (KB/MDR) cells. FOOD AND CHEMICAL TOXICOLOGY, [PMID:34217736] [10.1016/j.fct.2021.112381] |
| 13. Yuanguo Xiong, Hao Lu, Hanlin Xu. (2020) Galangin Reverses Hepatic Fibrosis by Inducing HSCs Apoptosis via the PI3K/Akt, Bax/Bcl-2, and Wnt/β-catenin Pathway in LX-2 Cells. BIOLOGICAL & PHARMACEUTICAL BULLETIN, [PMID:32893252] [10.1248/bpb.b20-00258] |
| 14. 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] |
| 15. 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] |
| 16. Hao Lu, Hui Yao, Rong Zou, Xiwen Chen, Hanlin Xu. (2019) Galangin Suppresses Renal Inflammation via the Inhibition of NF-κB, PI3K/AKT and NLRP3 in Uric Acid Treated NRK-52E Tubular Epithelial Cells. Biomed Research International, [PMID:31240210] [10.1155/2019/3018357] |
| 17. Li Zeng, Huafang Ding, Xing Hu, Guowen Zhang, Deming Gong. (2018) Galangin inhibits α-glucosidase activity and formation of non-enzymatic glycation products. FOOD CHEMISTRY, [PMID:30236734] [10.1016/j.foodchem.2018.07.148] |
| 18. Shuzhen Yang, Jie Zhou, Dongmei Li, Chunyu Shang, Litao Peng, Siyi Pan. (2016) The structure-antifungal activity relationship of 5,7-dihydroxyflavonoids against Penicillium italicum. FOOD CHEMISTRY, [PMID:28159264] [10.1016/j.foodchem.2016.12.001] |
| 19. Xiaodan Liu, Xia Wu. (2014) Fluorescence enhancement of fisetin by silver nanoparticles with cetyltrimethyl ammonium bromide micelles. RSC Advances, 5 (10): (7433-7439). [PMID:] [10.1039/C4RA12726A] |
| 20. Ting Wu, Xixi Zang, Mengying He, Siyi Pan, Xiaoyun Xu. (2013) Structure–Activity Relationship of Flavonoids on Their Anti-Escherichia coli Activity and Inhibition of DNA Gyrase. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, [PMID:23926942] [10.1021/jf402222v] |
| 21. Yanan Zhao, Bin Li, Jiang Liu, Lei Chen, Hui Teng. (2024) Galangin Prevents Against Ethanol-Induced Intestinal Barrier Dysfunction and NLRP3 Inflammasome Activation via NF-κB/MAPK Signaling Pathways in Mice and Caco-2 Cells. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, [PMID:38602402] [10.1021/acs.jafc.4c00747] |
| 22. Xia Yang, Yun Wang, Yan Sun, Jiali Guo, Zhaojun Geng, Bingyao Wei, Peiqin Li, Guanghui Tang. (2025) Integrated transcriptomics and metabolomics revealed the role of the flavonoid pathway in the resistance of Zanthoxylum bungeanum against leaf rust. SCIENTIA HORTICULTURAE, [PMID:] [10.1016/j.scienta.2025.113990] |
| 23. Daermu Qumu, Mu Tian, Hengxi Li, Xiujuan Yang, Binhui Han, Lanting Wei, Bo Li, Mengxue Ma, Junjie He, Xiaoni Shao. (2025) Study on the Mechanism of Galangin on Hyperuricemic Nephropathy Based on Metabolomics and Network Pharmacology. MOLECULAR NUTRITION & FOOD RESEARCH, [PMID:40150835] [10.1002/mnfr.70029] |
| 24. Kaiwen Lin, Zhongtao Wang, Erhao Wang, Xueer Zhang, Xiaofei Liu, Faming Feng, Xiaodan Yu, Guohui Yi, Yan Wang. (2024) Targeting TRPV1 signaling: Galangin improves ethanol-induced gastric mucosal injury. JOURNAL OF ETHNOPHARMACOLOGY, [PMID:39047882] [10.1016/j.jep.2024.118605] |
| 25. Haolin Zhang, Jingjing Zhang, Hui Cao, Petra Högger, Randolph Arroo, Mohamed A. Farag, Avi Shpigelman, Jianbo Xiao, Chunlin Li. (2025) Amination of Flavonoids Possessing a Pyrogallol Group in Cell Culture Medium at 37°C. Food Frontiers, 6 (2): (1058-1078). [PMID:] [10.1002/fft2.70002] |
| 26. Tongtong Ma, Qiao Huang, Lei Yuan, Shugang Yan, Yalin Mo, Yibin Ying, Yingchun Fu, Jinming Pan. (2025) Tailored Fluorescent Metal–Organic Frameworks Hybrid Membrane Sensor Arrays: Simultaneous and Selective Quantification of Multiple Antibiotics. Advanced Science, [PMID:40285681] [10.1002/advs.202502452] |
| 27. Yanan Zhao, Rui Wang, Ran Cao, Leyao Chen, Lei Chen, Hui Teng. (2025) Galangin Protects against Hyperuricemia via Ameliorating Gut–Kidney Axis Dysfunction in Mice. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, [PMID:40388492] [10.1021/acs.jafc.5c01260] |
| 28. Jianglin Zhang, Fan Yang, Xia Sun, Lingyu Gao, Jing Yan, Xiuxian Chen, Yuhua Gu, Shuaijie Song, Fuliang Hu, Xu'’ai Lin, Simon Duttwyler, Hao Cheng, Stijn van der Veen. (2025) 2-Hydroxychalcone is a gonococcal-specific antimicrobial with activity against elongation factor Tu and butanediol dehydrogenase. LIFE SCIENCES, [PMID:41015385] [10.1016/j.lfs.2025.123994] |
| 29. Yanan Zhao, Rui Wang, Ziyang Huang, Siting Ju, Binghua Dong, Hui Teng, Lei Chen. (2026) Galangin Mitigates Alcohol-Induced Intestinal Damage by Suppressing Ferroptosis via the SESN2/KEAP1/NRF2 Pathway in Mice and Caco-2 Cells. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, [PMID:41605867] [10.1021/acs.jafc.5c11761] |
| 30. Zheng Li, Mengrong Hu, Siyu Hou, Shufang Gao, Ziyi Wang, Jian Luo. (2026) Turning on the Fluorescence of Flavonoid Anions: Synergistic Roles of Spatial Constraints and Microbasicity in Poly(vinyl alcohol)/DMSO Films. JOURNAL OF PHYSICAL CHEMISTRY B, [PMID:41685506] [10.1021/acs.jpcb.5c08688] |
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