Butein

• CAS: 487-52-5
• Catalog Number: ACM487525-1
• Category: Main Products
• Molecular Weight: 272.25
• Molecular Formula: C15H12O5
• Synonyms: 2',3,4,4'-Tetrahydroxychalcone
• SMILES: C1=CC(=C(C=C1/C=C/C(=O)C2=C(C=C(C=C2)O)O)O)O
• Boiling Point: 560.92 °C at 760 mmHg (Predicted)
• Melting Point: 215 °C (lit.)
• Appearance: Solid
• Refractive Index: 1.75 (Predicted)

Case Study

Butein for the Inhibition of Lipoxygenase-5 and Hyaluronidase in Skin Carcinoma Cells

Raza W, et al. Biochemical and Biophysical Research Communications, 2025, 152047.

Butein was investigated for its anticancer potential against human skin carcinoma cells through a series of mechanistic and cytotoxicity assays. The compound exhibited potent antiproliferative effects, as demonstrated by Sulphorhodamine B (SRB), Neutral Red Uptake (NRU), and MTT assays, indicating concentration-dependent cytotoxicity. Experimental evaluation of enzyme inhibition showed that butein effectively inhibited lipoxygenase-5 (LOX-5) and hyaluronidase activities-two key enzymes implicated in tumor progression and extracellular matrix remodeling. Reactive oxygen species (ROS) quantification revealed significant intracellular ROS accumulation following butein treatment. Concurrently, mitochondrial membrane potential (MMP) disruption was observed via fluorescence-based assays, confirming the induction of mitochondrial-mediated apoptosis. Cell cycle analysis using flow cytometry showed G2/M arrest, highlighting butein's regulatory effect on cell cycle progression. Moreover, butein reduced cell motility, underscoring its anti-metastatic properties. Importantly, ex vivo hemolysis assays confirmed butein's hemocompatibility by preserving erythrocyte membrane integrity. Additionally, in silico ADME profiling predicted favorable oral bioavailability and high gastrointestinal absorption.

Butein for the Modulation of Adipogenesis, Inflammatory Response, and Glucose Metabolism in LPS-Stimulated Co-Culture Models

Ohmoto M, et al. Food Chemistry Advances, 2024, 5, 100851.

This study explores the experimental application of butein in modulating key cellular pathways associated with obesity and metabolic dysfunction using in vitro co-culture systems. Butein was investigated for its role in adipogenic differentiation, oxidative stress regulation, inflammatory response, and glucose metabolism across 3T3-L1 adipocytes and RAW264 macrophage cells.
To evaluate adipogenesis, 3T3-L1 preadipocytes were induced to differentiate in the presence of butein. Although lipid accumulation was not significantly altered, quantitative RT-PCR analysis showed marked upregulation of adipogenic marker genes, indicating enhanced transcriptional differentiation activity. Additionally, intracellular reactive oxygen species (ROS) were quantified using fluorescent probes, revealing that butein significantly reduced ROS levels in differentiated adipocytes.
For inflammation studies, a co-culture model of 3T3-L1 adipocytes and LPS-stimulated RAW264 macrophages was established to mimic the inflamed adipose microenvironment. Butein treatment resulted in a dose-dependent suppression of pro-inflammatory cytokine gene expression, as measured by real-time PCR.
To assess glucose metabolism, GLUT1 expression was analyzed in RAW264 cells following LPS stimulation and butein treatment. Butein significantly downregulated GLUT1 mRNA levels, indicating its regulatory role in glucose transporter expression under inflammatory conditions.

Butein for the Inhibition of Colorectal Cancer via p38-Mediated Apoptosis and Metastasis Suppression

Wang H, et al. Journal of Functional Foods, 2024, 119, 106293.

Butein was experimentally validated for its anti-cancer potential in colorectal cancer (CRC) through a combination of pharmacological and molecular approaches. In vitro assays using CRC cell lines demonstrated that Butein significantly inhibited cellular proliferation, induced apoptosis, and suppressed epithelial-mesenchymal transition (EMT), thereby reducing migration and invasion capabilities. These effects were assessed using standard proliferation assays, flow cytometry for apoptosis quantification, and transwell migration/invasion assays.
To elucidate the underlying mechanisms, molecular docking and network pharmacology analyses predicted the involvement of the p38 MAPK signaling pathway. This was experimentally confirmed through western blotting, which revealed increased phosphorylation of p38 following Butein treatment, and immunohistochemistry in tumor tissues, supporting its role in pathway activation. In vivo studies further corroborated these findings, with Butein-treated xenograft models exhibiting reduced tumor growth and decreased metastatic potential.

Butein for the Functional Reactivation of Mutant p53 in Cancer Cells

Song B, et al. Biomedicine & Pharmacotherapy, 2023, 163, 114773.

In this study, Butein was investigated for its ability to restore wild-type p53 function in cancer cells harboring the p53-R175H and p53-R273H mutations. Cellular thermal shift assays (CETSA) demonstrated that Butein enhanced the thermal stability of both mutant and wild-type p53, indicating direct binding and conformational stabilization. DNA-binding activity was evaluated using electrophoretic mobility shift assays (EMSAs), confirming that Butein reinstated the functional DNA-binding conformation of mutant p53. Furthermore, immunoprecipitation assays revealed that Butein disrupted the interaction between mutant p53 and heat shock protein 90 (Hsp90), a chaperone known to stabilize mutant p53 in an inactive state. Luciferase reporter assays showed increased transactivation of p53-responsive genes upon Butein treatment. Structural insights from molecular docking demonstrated that Butein binds allosterically near the DNA-binding loop-sheet-helix motif of mutant p53-R175H, promoting a shift toward wild-type-like conformation. Cell viability assays confirmed the selective induction of apoptosis in p53-mutant cancer cells following Butein treatment.

Butein for the Prevention of Corticosterone-Induced Apoptosis in Neuro2A Cells via MEK-ERK Signaling Modulation

Ohmoto M, et al. IBRO Neuroscience Reports, 2023, 14, 447-452.

Butein was evaluated for its neuroprotective role against corticosterone (CORT)-induced apoptosis in mouse Neuro2A (N2A) neuroblastoma cells. In this study, N2A cells were pretreated with 0.5 μM butein in serum-free DMEM for 30 minutes, followed by continued incubation with 0.5 μM butein and 50 μM CORT, either alone or in combination with 50 μM LY294002 (a PI3K inhibitor) or 50 μM PD98059 (a MEK inhibitor) for 24 hours. Cell viability was assessed using the MTT assay, and apoptotic markers were analyzed via western blotting. CORT significantly decreased N2A cell viability and ERK/AKT phosphorylation, while increasing cleaved caspase-3 levels. Butein pretreatment attenuated these apoptotic effects, particularly by partially restoring ERK phosphorylation. Notably, cotreatment with LY294002 and butein further enhanced ERK activation, while cotreatment with PD98059 and butein elevated AKT phosphorylation, indicating reciprocal regulation between MEK-ERK and PI3K-AKT pathways. The neuroprotective effect of butein was abolished by MEK inhibition, highlighting ERK signaling as the critical axis.

Custom Q&A

What is the PubChem CID for butein?

The PubChem CID for butein is 5281222.

What is the molecular formula of butein?

The molecular formula of butein is C15H12O5.

What is the molecular weight of butein?

The molecular weight of butein is 272.25 g/mol.

What is the IUPAC name of butein?

The IUPAC name of butein is (E)-1-(2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one.

What is the InChIKey of butein?

The InChIKey of butein is AYMYWHCQALZEGT-ORCRQEGFSA-N.

What are the synonyms of butein?

The synonyms of butein include butein, 487-52-5, 2',3,4,4'-Tetrahydroxychalcone, and 2',4',3,4-Tetrahydroxychalcone.

Is butein a natural product?

Yes, butein is a natural product found in Dahlia pinnata, Calanticaria bicolor, and other organisms.

What is the CAS number of butein?

The CAS number of butein is 487-52-5.

What is the ChEBI ID of butein?

The ChEBI ID of butein is CHEBI:128000.

What is the XLogP3-AA value of butein?

The XLogP3-AA value of butein is 2.8.