Genistein

• CAS: 446-72-0
• Catalog Number: ACM446720-2
• Category: Main Products
• Molecular Weight: 270.24
• Molecular Formula: C15H10O5
• Description: Having property of female hormone and antiestrogenic; Having oxidation resistance effect; Control activity of PTK; Control activity of topoisomeraseII
• Synonyms: Sophoricol
• IUPAC Name: 5,7-Dihydroxy-3-(4-hydroxyphenyl)chromen-4-one
• SMILES: C1=CC(=CC=C1C2=COC3=CC(=CC(=C3C2=O)O)O)O
• InChI: InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-7,16-18H
• InChI Key: TZBJGXHYKVUXJN-UHFFFAOYSA-N
• Boiling Point: 333.35 °C
• Melting Point: 297-298 °C
• Flash Point: 217.1 °C
• Density: 1.2319 g/cm³
• Solubility: Insoluble in water
• Appearance: Off-white powder
• Storage: -20 °C
• Active Content: 95%
• Complexity: 411
• Effective Constituent: Genistein
• Exact Mass: 270.05282342
• MDL Number: MFCD00016952
• Monoisotopic Mass: 270.05282342
• Physical State: Solid
• pKa: 6.51±0.20(Predicted)
• Plant Origin: dried flower of Sophora japonica L. or mature fruit
• Refractive Index: 1.6000
• Size: 1g,5g,25g
• Solubility In Water: Insoluble
• Topological Polar Surface Area: 87 Ų

Case Study

Genistein for the Mitigation of Renal Fibrosis via Inhibition of HIF-1α-Mediated EMT and Glycolysis

Jiang T, et al. Food Bioscience, 2025, 71, 107172.

In a diabetic nephropathy model, genistein was experimentally validated for its therapeutic potential against renal fibrosis. C57BL/6 mice were induced with diabetes using a high-fat, high-sugar diet plus streptozotocin. Following genistein administration, renal injury and fibrosis were assessed histologically. ELISA and immunoblotting quantified glycolytic enzyme activity and epithelial-mesenchymal transition (EMT) markers. Genistein treatment markedly suppressed EMT and glycolytic flux, evidenced by reduced lactate accumulation. Molecular docking revealed strong binding affinity between genistein and hypoxia-inducible factor-1α (HIF-1α), implicating direct molecular interaction. Overexpression studies in renal epithelial cells confirmed that HIF-1α promotes glycolysis and EMT under hyperglycemic conditions, while genistein downregulates HIF-1α, thereby mitigating these pathological processes.

Synergistic Chemotherapy Enhancement by Genistein through Metabolic Reprogramming in Breast Cancer Cells

Tobón-Cornejo S, et al. Life Sciences, 2025, 370, 23562.

Genistein was experimentally applied to modulate metabolism and potentiate chemotherapy in breast cancer (BCa) cells. Two human BCa cell lines-MCF7 (ER+) and MDA-MB-231 (ER-)-were treated with low-dose genistein alone or combined with chemotherapeutics. Cell viability assays and clonogenic assays assessed cytotoxicity and colony formation capacity. ATP quantification and Seahorse XF analysis evaluated energy metabolism shifts, revealing reduced ATP production and mitochondrial respiration in MCF7 cells. Western blotting measured CPT1 expression, demonstrating suppressed fatty acid oxidation, while intracellular lipid accumulation was confirmed via lipid staining. Wound healing assays further indicated impaired cell migration. The combinatorial treatment induced pronounced cytotoxicity and senescence compared to monotherapies. This study highlights genistein's metabolic reprogramming capacity and its synergistic enhancement of chemotherapy efficacy in BCa models.

Genistein for Alleviation of Colitis via Microbiota Modulation and Anti-Inflammatory Mechanisms

He Y, et al. Current Research in Food Science, 2025, 10, 101016.

In a DSS-induced colitis mouse model, genistein was evaluated for its therapeutic efficacy through microbiota-mediated mechanisms. Mice received genistein treatment following DSS administration, with additional groups receiving antibiotics to deplete gut microbiota, confirming the dependency of genistein's effects on microbial presence. Genistein supplementation significantly restored gut microbial alpha diversity, notably enhancing Marvinbryantia formatexigens and Lachnospiraceae abundance. Targeted microbial modulation was validated by colonizing mice with live M. formatexigens, which elevated short-chain fatty acids (SCFAs) and ameliorated colitis. Mechanistically, genistein suppressed the NF-κB and COX-2/PGE2 inflammatory pathways and reduced Mucin 2 secretion, mitigating colonic injury. The antibiotic-treated cohort exhibited no genistein benefit, underscoring the microbiota's critical role.

Genistein for the Inhibition of Androgen Receptor Pathway in Castration-Resistant Prostate Cancer

Yu X-P, et al. Journal of Asian Natural Products Research, 2025.

In vivo studies demonstrated genistein's efficacy against castration-resistant prostate cancer (CRPC) by targeting androgen biosynthesis and receptor signaling. CRPC cells were treated with genistein, followed by qRT-PCR and Western blot analyses, revealing significant downregulation of AKR1C3, SRD5A2, CYP11A1, and 3βHSD involved in de novo androgen synthesis. Immunofluorescence and nuclear fractionation assays confirmed genistein's inhibition of androgen receptor (AR) activation and nuclear translocation. These results position genistein as a promising therapeutic candidate, effectively suppressing both androgen production and AR-mediated transcriptional activity in CRPC.

Genistein for the Reversal of Estrogen-Exacerbated Chronic Masseter Hyperalgesia via ERK1/2 Pathway Suppression

Mo S, et al. European Journal of Pharmacology, 2025, 998, 177544.

In a rat model of experimental occlusal interference (EOI)-induced chronic masseter hyperalgesia, genistein demonstrated efficacy in counteracting the exacerbating effects of 17β-estradiol (E2). Ovariectomized rats were pretreated with genistein or genistin, followed by E2 replacement and EOI induction. Pain sensitivity was quantified via bilateral head withdrawal thresholds. Molecular assessments involved immunofluorescence and Western blotting of spinal trigeminal nucleus (Sp5) tissues to evaluate phosphorylation of ERK1/2 and protein tyrosine kinases (YAP, Src). Intrathecal injection of the ERK inhibitor PD98059 further elucidated pathway involvement. Results revealed that genistein suppressed PTK activity and p-ERK1/2 expression in Sp5, partially reversing E2-aggravated hyperalgesia. This study underscores genistein's experimental utility in modulating pain pathways via ERK1/2 signaling inhibition.

Genistein for Modulating Gut Microbiota and Glutamate Pathways in a Depression Rat Model

Ma C, et al. Current Research in Food Science, 2025, 10, 101020.

In a rat model of depression, genistein (20-40 mg/kg) was administered via oral gavage to investigate its antidepressant mechanism through gut microbiota modulation and neurotransmitter regulation. Behavioral assessments included body weight, glucose preference, immobility time, body temperature, and serum 5-HT levels, alongside ACTH and corticosterone quantification. High-throughput 16S rRNA sequencing revealed that genistein treatment increased Firmicutes and Actinobacteriota abundance, particularly elevating Bifidobacterium, while reducing Bacteroidota. Metagenomic analysis demonstrated upregulation of glutamate metabolism genes, notably enhancing glutamic acid decarboxylase (GAD) expression to boost GABA synthesis. This biochemical shift indirectly elevated 5-HT levels, comparable to fluoxetine treatment. The study highlights genistein's potential as a microbiota-targeting antidepressant, mediated via metabolic and neurotransmitter pathways.

Custom Q&A

What is the PubChem CID of genistein?

The PubChem CID of genistein is 5280961.

What is the molecular formula of genistein?

The molecular formula of genistein is C15H10O5.

What are the synonyms of genistein?

The synonyms of genistein include genistein, Prunetol, 4',5,7-Trihydroxyisoflavone, and Genisterin.

What is the molecular weight of genistein?

The molecular weight of genistein is 270.24 g/mol.

What is the IUPAC name of genistein?

The IUPAC name of genistein is 5,7-dihydroxy-3-(4-hydroxyphenyl)chromen-4-one.

What is the InChI of genistein?

The InChI of genistein is InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-7,16-18H.

What is the InChIKey of genistein?

The InChIKey of genistein is TZBJGXHYKVUXJN-UHFFFAOYSA-N.

What is the canonical SMILES of genistein?

The canonical SMILES of genistein is C1=CC(=CC=C1C2=COC3=CC(=CC(=C3C2=O)O)O)O.

What is the CAS number of genistein?

The CAS number of genistein is 446-72-0.

What are the natural sources of genistein?

The natural sources of genistein include tofu, fava beans, soybeans, kudzu, and lupin.