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Moligand™, analytical standard Analytical standard,Moligand™ for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
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 16 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Biochanin A, an isoflavone, is a natural plant phytoestrogen which has been reported to be an antiproliferative and anti-inflammatory agent. Studies show that this compound inhibits iNOS expression and lipopolysacharide (LPS)-induced nitric oxide production in macrophages. Additionally, Biochanin A displays the ability to block phosphorylation of IκBα and p38 MAPK, which prevents NF-κB activation. Furthermore, Biochanin A has been observed to suppress IL-6, IL-1β, and TNF-α production.
| Sonrisas canónicas | COC1=CC=C(C=C1)C2=COC3=CC(=CC(=C3C2=O)O)O |
|---|---|
| IUPAC Name | 5,7-dihydroxy-3-(4-methoxyphenyl)chromen-4-one |
| InChIKey | WUADCCWRTIWANL-UHFFFAOYSA-N |
| INCHI | 1S/C16H12O5/c1-20-11-4-2-9(3-5-11)12-8-21-14-7-10(17)6-13(18)15(14)16(12)19/h2-8,17-18H,1H3 |
| Isómeros SMILES | COC1=CC=C(C=C1)C2=COC3=CC(=CC(=C3C2=O)O)O |
| WGK Alemania | 3 |
| Peso molecular | 284.26 |
| Beilstein | 278107 |
| Reaxy-Rn | 278107 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=278107&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 |
| Clase | Isoflavonoids |
| Subclass | O-methylated isoflavonoids |
| Intermediate Tree Nodes | 4'-O-methylated isoflavonoids |
| Direct Parent | 4'-O-methylisoflavones |
| Alternative Parents | Isoflavones Hydroxyisoflavonoids Chromones Phenoxy compounds Methoxybenzenes Anisoles Pyranones and derivatives Alkyl aryl ethers 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Vinylogous acids Heteroaromatic compounds Oxacyclic compounds Organic oxides Hydrocarbon derivatives |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | 4p-o-methylisoflavone - Isoflavone - Hydroxyisoflavonoid - Chromone - Benzopyran - 1-benzopyran - Anisole - Phenoxy compound - Phenol ether - Methoxybenzene - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Pyranone - Alkyl aryl ether - Monocyclic benzene moiety - Benzenoid - Pyran - Vinylogous acid - Heteroaromatic compound - Ether - Organoheterocyclic compound - Oxacycle - Organooxygen compound - Organic oxygen compound - Hydrocarbon derivative - Organic oxide - Aromatic heteropolycyclic compound |
| Descripción | This compound belongs to the class of organic compounds known as 4'-o-methylisoflavones. These are isoflavones with methoxy groups attached to the C4' atom of the isoflavone backbone. |
| External Descriptors | Isoflavonoids |
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| Punto de fusión (°C) | 212-216°C |
|---|---|
| Peso molecular | 284.260 g/mol |
| XLogP3 | 3.000 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 2 |
| Exact Mass | 284.068 Da |
| Monoisotopic Mass | 284.068 Da |
| Topological Polar Surface Area | 76.000 Ų |
| Heavy Atom Count | 21 |
| 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. Li Xigong, Fu Jing, Guan Ming, Shi Haifei, Pan Wenming, Lou Xianfeng. (2023) Biochanin A attenuates spinal cord injury in rats during early stages by inhibiting oxidative stress and inflammasome activation. Neural Regeneration Research, 19 (9): (2050). [PMID:38227535] [10.4103/1673-5374.390953] |
| 2. Yufeng Chen, Guobin Xia, Chunfeng Wang, Huawei Wu, Xiaogang Xu, Genxiang Mao, Jiong Wu, Zhenlei Zhao. (2023) Impact of dietary plant flavonoids on 7,8-dihydroxyflavone transepithelial transport in human intestinal Caco-2 cells. Food Science & Nutrition, [PMID:37970375] [10.1002/fsn3.3581] |
| 3. Lei He, Qian Hu, Liyang Wei, Xuliyang Ge, Ning Yu, Ying Chen. (2023) Unravelling dynamic changes in non-volatile and volatile metabolites of pulses during soaking: An integrated metabolomics approach. FOOD CHEMISTRY, [PMID:37141754] [10.1016/j.foodchem.2023.136231] |
| 4. Zili Guo, Yilin Liu, Jiani Xiang, Xianrui Liang. (2023) Mechanochemical preparation of red clover extract/β-cyclodextrin dispersion: Enhanced water solubility and activities in alleviating high-fat diet-induced lipid accumulation and gut microbiota dysbiosis in mice. FOOD CHEMISTRY, [PMID:37060670] [10.1016/j.foodchem.2023.136084] |
| 5. Wenjie Yu, Fengjie Sun, Ruixin Xu, Meng Cui, Yongquan Liu, Quanyuan Xie, Limin Guo, Chenxian Kong, Xin Li, Xiali Guo, Liping Luo. (2022) Chemical composition and anti-inflammatory activities of Castanopsis honey. Food & Function, 14 (1): (250-261). [PMID:36484340] [10.1039/D2FO02233H] |
| 6. 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] |
| 7. Junying Xu, Xuejing Yang, Jiadong Pan, Honghong Fan, Jie Mei, Dong Hua. (2022) Biochanin A Suppresses Tumor Progression and PD-L1 Expression via Inhibiting ZEB1 Expression in Colorectal Cancer. Journal of Oncology, [PMID:35242187] [10.1155/2022/3224373] |
| 8. Liuying Zhu, Wenting Li, Zeyuan Deng, Hongyan Li, Bing Zhang. (2020) The Composition and Antioxidant Activity of Bound Phenolics in Three Legumes, and Their Metabolism and Bioaccessibility of Gastrointestinal Tract. Foods, 9 (12): (1816). [PMID:33297502] [10.3390/foods9121816] |
| 9. 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] |
| 10. 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] |
| 11. Xiafen Xu, Xinhui Li, Xianrui Liang. (2017) Application of ultra-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry in identification of three isoflavone glycosides and their corresponding metabolites. RAPID COMMUNICATIONS IN MASS SPECTROMETRY, 32 (3): (262-268). [PMID:29222826] [10.1002/rcm.8038] |
| 12. 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] |
| 13. Mengying He, Ting Wu, Siyi Pan, Xiaoyun Xu. (2014) Antimicrobial mechanism of flavonoids against Escherichia coli ATCC 25922 by model membrane study. APPLIED SURFACE SCIENCE, [PMID:] [10.1016/j.apsusc.2014.03.125] |
| 14. Hui Cao, Xiaohui Jing, Donghui Wu, Yujun Shi. (2013) Methylation of genistein and kaempferol improves their affinities for proteins. INTERNATIONAL JOURNAL OF FOOD SCIENCES AND NUTRITION, [PMID:23311465] [10.3109/09637486.2012.759186] |
| 15. Yu-Qing Li, Xin-Ming Yu, Xue-Mei Shang, Jing-Yi Lin, Rui-Zhi Tan, Jian-Chun Li, Hong-Wei Su, Hong-Ping Shen, Hong-Lian Wang, Li Wang. (2024) Biochanin A Suppresses Klf6-mediated Smad3 Transcription to Attenuate Renal Fibrosis in UUO mice. PHYTOMEDICINE, [PMID:39326137] [10.1016/j.phymed.2024.156067] |
| 16. You Zhou, You Wu, Rui Zhu. (2025) KLF6 enhances ferroptosis in S-AKI through the NCOA4/ACSL4/LPCAT3 axis. INTERNATIONAL IMMUNOPHARMACOLOGY, [PMID:40811945] [10.1016/j.intimp.2025.115376] |
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