Biochanin A - Moligand™, 10mM in DMSO , CAS No.491-80-5

CAS: 491-80-5 Cat. No.: B408800 Molecular Weight: 284.26 Beilstein Registry Number: 278107 EC Number: 207-744-7

GRADE & PURITY Moligand™, 10mM in DMSO

Synonyms

4-Methylgenistein | 4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-methoxyphenyl)-

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Information

Biochanin A Biochanin A (4-Methylgenistein), an O-methylated isoflavone from Trifolium pratense, inhibits protein tyrosine kinase (PTK) of epidermal growth factor receptor with IC50 values of 91.5 μM.
In vitro

Biochanin A has been reported to inhibit protein tyrosine kinase (PTK) of epidermal growth factor receptor with IC50 values of 91.5 μM Biochanin A inhibits the hydrolysis of 0.5 μM anandamide by mouse, rat and human fatty acid amide hydrolase (FAAH) with IC50 values of 1.8, 1.4 and 2.4 μM respectively. Biochanin A inhibits both serum and EGF-stimulated growth of LNCaP and DU-145 cells (IC50 values from 8.0 to 27 micrograms/ml for serum and 4.3 to 15 micrograms/ml for EGF), but has no significant effect of the EGF receptor tyrosine autophosphorylation.

In vivo

LD50: Mice 63mg/kg (i.p.)
Cell Data

cell lines：

Concentrations：

Incubation Time：

Powder Purity:≥99%

Specifications

Synonyms

4-Methylgenistein | 4H-1-Benzopyran-4-one, 5, 7-dihydroxy-3-(4-methoxyphenyl)-

Specifications & Purity

Moligand™, 10mM in DMSO

Biochemical and Physiological Mechanisms

Biochanin A (4-Methylgenistein), an O-methylated isoflavone from Trifolium pratense, inhibits protein tyrosine kinase (PTK) of epidermal growth factor receptor with IC50 values of 91.5 μM.

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Names and Identifiers

• Isomeric SMILES: COC1=CC=C(C=C1)C2=COC3=CC(=CC(=C3C2=O)O)O
• WGK Germany: 3
• Molecular Weight: 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=

Associated Targets(Human)

CA12 Tclin Carbonic anhydrase 12 (1 Activities)

Discover Target: CA12

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CA7 Tclin Carbonic anhydrase 7 (1 Activities)

Discover Target: CA7

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CYP19A1 Tclin Aromatase (1 Activities)

Discover Target: CYP19A1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

Chemical and Physical Properties

• Melt Point(°C): 212-216°C

References

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6. 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]

7. 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]

8. 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]

9. 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]

10. 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]

11. 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]

12. 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]

13. 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]

14. 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]

15. 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]

16. 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]