Art. -Nr.: HY-141462

2',4-Dihydroxychalcone

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2',4-Dihydroxychalcone is an orally active natural chalcone flavonoid. 2',4-Dihydroxychalcone restores intestinal barrier integrity by upregulating tight junction proteins, regulates intestinal flora balance and alleviates inflammation. 2',4-Dihydroxychalcone induces GPX4 degradation, ferroptosis and apoptosis, triggers cell cycle arrest, and exhibits broad anti-tumor activity. 2',4-Dihydroxychalcone also possesses antifungal activity, antileishmanial activity, and reduces the hemolytic effect and virulence of Vibrio vulnificus.

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CAS. Nr.: 13323-66-5
Formel: C₁₅H₁₂O₃
Molecular Weight:240.25

Speicherung:

4°C, stored under nitrogen

* In solvent : -80°C, 6 months; -20°C, 1 month (stored under nitrogen)

2',4-Dihydroxychalcone Chemical Structure

CAS. Nr.: 13323-66-5

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Biologische Aktivität
- Beschreibung
- Cellular Effect
- In Vitro
- In Vivo
Chemical Information
Reinheit & Dokumentation
Verweise
Calculators
Help & FAQs
Bioz

Biologische Aktivität

Beschreibung

Cellular Effect

Cell Line	Type	Value	Description	References
HL-60	IC₅₀	7.1 μM Compound: 5	Cytotoxicity against human HL60 cells by MTT assay Cytotoxicity against human HL60 cells by MTT assay	[PMID: 25091929]
NALM-6	IC₅₀	40.6 μM Compound: 5	Cytotoxicity against human NALM6 cells by MTT assay Cytotoxicity against human NALM6 cells by MTT assay	[PMID: 25091929]
Neutrophil	IC₅₀	1.5 μM Compound: 22	Inhibition of PMA-induce ROS/RNS generation in human neutrophils measured up to 30 mins in presence of 30 mM glucose by luminol-amplified chemiluminescence method Inhibition of PMA-induce ROS/RNS generation in human neutrophils measured up to 30 mins in presence of 30 mM glucose by luminol-amplified chemiluminescence method	[PMID: 33006891]
Neutrophil	IC₅₀	1.6 μM Compound: 22	Inhibition of PMA-induce ROS/RNS generation in human neutrophils measured up to 30 mins in presence of 5.5 mM glucose by luminol-amplified chemiluminescence method Inhibition of PMA-induce ROS/RNS generation in human neutrophils measured up to 30 mins in presence of 5.5 mM glucose by luminol-amplified chemiluminescence method	[PMID: 33006891]
RBL-1	IC₅₀	42 μM Compound: 4	Inhibition of 5-lipoxygenase in rat RBL1 cells Inhibition of 5-lipoxygenase in rat RBL1 cells	10.1007/s00044-013-0745-7
RBL-1	IC₅₀	42 μM Compound: 5	In vitro inhibition against 5-lipoxygenase in RBL-1 cells was determined In vitro inhibition against 5-lipoxygenase in RBL-1 cells was determined	[PMID: 8254620]
WM-115	IC₅₀	69.1 μM Compound: 5	Cytotoxicity against human WM115 cells by MTT assay Cytotoxicity against human WM115 cells by MTT assay	[PMID: 25091929]

In Vitro

2',4-Dihydroxychalcone (1.25-40 μM; 1-2 h) selectively inhibits NLRP3 inflammasome activation in THP-1-derived macrophages and 774A.1 macrophages by blocking the cleavage of caspase-1 and Gasdermin D, and exhibits no cytotoxicity at concentrations up to 40 μM^[1].
2',4-Dihydroxychalcone (25 μM; 1 h) potently inhibits Nigericin (HY-127019)-induced IL-1β secretion in THP-1-derived macrophages^[1].
2',4-Dihydroxychalcone (12.5-50 µM; 24-72 h) potently inhibits the proliferation of HuCCT1 and QBC939 cholangiocarcinoma cells in a concentration-dependent manner^[2].
2',4-Dihydroxychalcone (12.5-50 µM; 14 days) inhibits the colony-forming ability of HuCCT1 and QBC939 cholangiocarcinoma cells in a concentration-dependent manner^[2].
2',4-Dihydroxychalcone (25 µM; 24 h) inhibits the proliferation of HuCCT1 and QBC939 cholangiocarcinoma cells by reducing EdU incorporation^[2].
2',4-Dihydroxychalcone (12.5-50 µM; 48 h) inhibits horizontal and vertical migration of HuCCT1 and QBC939 cholangiocarcinoma cells in a concentration-dependent manner^[2].
2',4-Dihydroxychalcone (12.5-50 µM; 24 h) increases intracellular ROS levels in HuCCT1 and QBC939 cholangiocarcinoma cells in a concentration-dependent manner^[2].
2',4-Dihydroxychalcone (12.5-50 µM; 24 h) induces ferroptosis in HuCCT1 and QBC939 cholangiocarcinoma cells^[2].
2',4-Dihydroxychalcone (12.5-50 µM; 24 h) inhibits epithelial-mesenchymal transition in HuCCT1 and QBC939 cholangiocarcinoma cells, while downregulating the PI3K/AKT/mTOR signaling pathway and ferroptosis-related markers SLC7A11 and GPX4^[2].
2',4-Dihydroxychalcone (12.5-50 µM) downregulates the expression of ERO1A in HuCCT1 and QBC939 cholangiocarcinoma cells in a concentration-dependent manner^[2].
2',4-Dihydroxychalcone (0.06-256 μg/mL; 48 h) inhibits the metabolic activity and hyphal growth of Aspergillus fumigatus Af293, with an MIC₅₀ ranging from 64 to 128 μg/mL, and significantly reduces hyphal growth at a concentration of 256 μg/mL^[3].
2',4-Dihydroxychalcone (8 μg/mL; 48 h) inhibits the radial growth of Aspergillus fumigatus Af293 by 20%, blocks its sporulation process, and reduces the expression levels of sporulation-related genes brlA, abaA and wetA by 3-5 folds^[3].
2',4-Dihydroxychalcone (8 μg/mL; 48 h) reduces the expression levels of calcineurin pathway genes cnaA and crzA in Aspergillus fumigatus Af293^[3].
2',4-Dihydroxychalcone (4-256 μg/mL; 48 h) enhances the antifungal activity of Itraconazole (HY-17514) and Caspofungin (HY-17006A) against Aspergillus fumigatus Af293^[3].
2',4-Dihydroxychalcone (0.195-100.0 µg/mL; 72 h) potently inhibits the growth of Leishmania amazonensis promastigotes, with an IC₅₀ of 0.4 μM, and this compound shows high selectivity for parasites over mammalian cells^[4].
2',4-Dihydroxychalcone (24 h) exhibits low cytotoxicity against mouse peritoneal macrophages, with a CC₅₀ of 416.7 μM^[4].
2',4-Dihydroxychalcone (5-20 μg/mL; 48 h) induces morphological changes associated with apoptosis in human gastric cancer MGC-803 cells, with severe cell detachment and nuclear damage observed at the highest concentration^[5].
2',4-Dihydroxychalcone (5-20 μg/mL; 48 h) induces cell cycle arrest in human gastric cancer MGC-803 cells: it triggers S-phase arrest at 5 μg/mL, induces G2/M-phase arrest in a dose-dependent manner as the concentration increases to 10 μg/mL, while the G2/M-phase arrest effect attenuates at 20 μg/mL^[5].
2',4-Dihydroxychalcone (2.5-20 μg/mL; 48 h) increases the activity of caspase-3 in human gastric cancer MGC-803 cells in a dose-dependent manner^[5].
2',4-Dihydroxychalcone (5-20 μg/mL; 48 h) downregulates the expression of survivin mRNA in human gastric cancer MGC-803 cells in a dose-dependent manner^[5].
2',4-Dihydroxychalcone (0.2-5 μM; cultured to an OD₆₀₀ of 1.8-2.0) potently reduces the transcription levels of HlyU-regulated toxin genes rtxA1 and vvhA in wild-type Vibrio vulnificus MO6-24/O, without altering the expression of hlyU or hns^[6].
2',4-Dihydroxychalcone (2-8 μM) inhibits the hemolytic activity of wild-type *Vibrio vulnificus* MO6-24/O in a concentration-dependent manner, and at the concentration of 8 μM, the hemolysis level decreases to a level comparable to that of the ΔhlyU mutant^[6].
2',4-Dihydroxychalcone exhibits low cytotoxicity against HeLa and HEK293 cells, with IC₅₀ values of 100.3 μM and 60.0 μM, respectively, which are much higher than the maximum working concentration of 8 μM^[6].
2',4-Dihydroxychalcone (150-300 μM) inhibits the specific DNA-binding activity of purified wild-type Vibrio vulnificus HlyU protein with the P_rtxA1 promoter, and prevents the formation of specific high-mobility DNA-protein complexes^[6].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Cell Proliferation Assay^[2]

Cell Line:

Human cholangiocarcinoma HuCCT1 and QBC939 cells
Concentration:

12.5, 25 and 50 µM
Incubation Time:

24 h, 48 h, 72 h
Result:

Resulted in significant, concentration-dependent inhibition of HuCCT1 and QBC939 cell proliferation at all time points, compared to untreated controls.

Cell Proliferation Assay^[2]

Cell Line:

Human cholangiocarcinoma HuCCT1 and QBC939 cells
Concentration:

12.5, 25 and 50 µM
Incubation Time:

14 days
Result:

Caused a significant, concentration-dependent reduction in colony number for both HuCCT1 and QBC939 cells, compared to untreated controls.

Cell Proliferation Assay^[2]

Cell Line:

Human cholangiocarcinoma HuCCT1 and QBC939 cells
Concentration:

25 µM
Incubation Time:

24 h
Result:

Inhibited DNA synthesis (EdU incorporation) in CCA cells, indicating reduced proliferation.

Cell Migration Assay^[2]

Cell Line:

Human cholangiocarcinoma HuCCT1 and QBC939 cells
Concentration:

12.5, 25 and 50 µM
Incubation Time:

48 h
Result:

Caused a significant, concentration-dependent reduction in wound closure (horizontal migration) for both HuCCT1 and QBC939 cells, compared to untreated controls.\nCaused a significant, concentration-dependent reduction in the number of migrated cells (vertical migration) for both HuCCT1 and QBC939 cells, compared to untreated controls.

Western Blot Analysis^[2]

Cell Line:

Human cholangiocarcinoma HuCCT1 and QBC939 cells
Concentration:

12.5, 25 and 50 µM
Incubation Time:

24 h
Result:

Caused a significant, concentration-dependent increase in epithelial marker E-cadherin levels in both HuCCT1 and QBC939 cells, compared to untreated controls.
Caused a significant, concentration-dependent decrease in mesenchymal markers (Vimentin, Snail, Slug) and matrix metalloproteinases (MMP2, MMP9) levels in both HuCCT1 and QBC939 cells, compared to untreated controls.
Reduced protein levels of phosphorylated PI3K, AKT, and mTOR in both HuCCT1 and QBC939 cells, compared to untreated controls.
Downregulated ferroptosis-related markers SLC7A11 and GPX4 in both HuCCT1 and QBC939 cells, compared to untreated controls.

Apoptosis Analysis^[5]

Cell Line:

human gastric cancer MGC-803 cells
Concentration:

5 μg/mL, 10 μg/mL, 20 μg/mL
Incubation Time:

48 h
Result:

Induced marked nuclear condensation, nuclear fragmentation, and apoptotic body formation at 5 μg/mL and 10 μg/mL.
Caused most cells to detach from coverslips and float in the medium, with complete destruction of nuclear morphology in remaining adherent cells at 20 μg/mL.

Cell Cycle Analysis^[5]

Cell Line:

human gastric cancer MGC-803 cells
Concentration:

5 μg/mL, 10 μg/mL, 20 μg/mL
Incubation Time:

48 h
Result:

Increased the percentage of cells in S-phase from 30.51% (control) to 44.72%, and increased the percentage of cells in G2/M phase from 18.36% (control) to 26.71% at 5 μg/mL.
Caused a dose-dependent increase in G2/M phase cells to 60.53%, with a corresponding decrease in S-phase cells to 8.92% at 10 μg/mL.
Reduced the percentage of G2/M phase cells to 30.60%, with S-phase cells at 23.90% at 20 μg/mL.

RT-PCR^[5]

Cell Line:

human gastric cancer MGC-803 cells
Concentration:

5 μg/mL, 10 μg/mL, 20 μg/mL
Incubation Time:

48 h
Result:

Reduced survivin mRNA expression to ~85% of control at 5 μg/mL.
Reduced survivin mRNA expression to ~40% of control (P < 0.05) at 10 μg/mL.
Reduced survivin mRNA expression to ~15% of control (P < 0.05) at 20 μg/mL.
Decreased expression in a dose-dependent manner.

Real Time qPCR^[6]

Cell Line:

wild-type Vibrio vulnificus MO6-24/O cells
Concentration:

0.2, 0.5, 1, 2 and 5 μM.
Incubation Time:

grown to OD₆₀₀ 1.8-2.0
Result:

Reduced rtxA1 transcript levels by more than 30-fold compared to the DMSO control at 5 μM.
Caused concentration-dependent reductions in the transcript levels of rtxA1 and vvhA at 0.2, 0.5, 1, and 2 μM.
Left hlyU transcript levels unchanged at 0.2, 0.5, 1, and 2 μM.
Caused no significant change in hns gene expression at 0.2, 0.5, 1, and 2 μM.

In Vivo

2',4-Dihydroxychalcone (10-30 mg/kg; i.g.; daily; 10 days) significantly alleviates DSS (HY-116282C)-induced acute ulcerative colitis in C57BL/6J mice by inhibiting NLRP3 inflammasome activation, restoring gut barrier integrity, and balancing gut microbiota, with no observed organ toxicity^[1].
2',4-Dihydroxychalcone (6.25-12.5 mg/kg; i.p.; repeated dosing schedule) significantly inhibits cholangiocarcinoma xenograft tumor growth with minimal organ toxicity^[2].
2',4-Dihydroxychalcone (15 mg/kg; injection; single dose) provides ~50% protection to Galleria mellonella larvae against Vibrio vulnificus infection^[6].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:

C57BL/6J (6-week-old male, specific pathogen-free, DSS-induced acute ulcerative colitis)^[1]
Dosage:

10 mg/kg; 30 mg/kg
Administration:

i.g.; daily; 10 days
Result:

Significantly mitigated body weight loss (30 mg/kg group showed greater preservation) and reduced disease activity index (DAI) scores compared to DSS model group.
Preserved colon length, alleviated colon mucosal ulceration, crypt loss, and epithelial damage, and reduced histological scores.
Inhibited NLRP3 inflammasome activation in colon tissue, as shown by reduced NLRP3, cleaved caspase-1, cleaved Gasdermin D, IL-1β, and IL-6 levels.
Increased mRNA and protein levels of tight junction proteins occludin and ZO-1, restoring gut barrier integrity.
Showed no abnormal lesions in major organs (heart, liver, spleen, lung, kidney), indicating no organ toxicity.

Animal Model:

BALB/c nude (female, 4 weeks old, specific pathogen-free housing)^[2]
Dosage:

6.25 mg/kg; 12.5 mg/kg
Administration:

i.p.; repeated dosing schedule
Result:

Significantly reduced tumor weight and volume compared to the control group.
Produced a more pronounced reduction in tumor weight and volume at 12.5 mg/kg than at 6.25 mg/kg.
Markedly decreased Ki-67 and ERO1A expression in tumor tissues, with greater reduction in the 12.5 mg/kg group than the 6.25 mg/kg group.
Showed no histopathological changes in liver and kidney tissues, indicating minimal toxicity.

Animal Model:

wax-worm larvae (130 mg)^[6]
Dosage:

15 mg/kg
Administration:

injection; single dose
Result:

Increased larval survival to ~50% by 30 hours post-infection, compared to 10% in the untreated infected group.
Improved health index based on motility, cocoon formation, melanization, and survival.

Chemical Information

CAS. Nr. 13323-66-5
Appearance Solid
Molecular Weight 240.25
Formel C₁₅H₁₂O₃
SMILES

O=C(C1=CC=CC=C1O)/C=C/C2=CC=C(O)C=C2
Structure Classification
- Phenols
- Polyphenols
Initial Source
Versand

Room temperature in continental US; may vary elsewhere.
Speicherung

4°C, stored under nitrogen

* In solvent : -80°C, 6 months; -20°C, 1 month (stored under nitrogen)

Reinheit & Dokumentation

Handling Instructions (2659 KB)

Verweise

[1]. Zhang G, et al. 2',4'-dihydroxychalcone alleviates inflammatory bowel disease by inhibiting NLRP3 inflammasome and modulating gut microbiota. Frontiers in immunology. 2026;17:1751218. [Content Brief]

[2]. Wang T, et al. 2',4'-dihydroxychalcone induces ferroptosis through ERO1A/GPX4 regulatory axis in cholangiocarcinoma. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2025 Nov;147:157192. [Content Brief]

[3]. Seo YH, et al. In Vitro Antifungal Activity and Mode of Action of 2',4'-Dihydroxychalcone against Aspergillus fumigatus. Mycobiology. 2015 Jun;43(2):150-6. [Content Brief]

[4]. Passalacqua TG, et al. The 2',4'-dihydroxychalcone could be explored to develop new inhibitors against the glycerol-3-phosphate dehydrogenase from Leishmania species. Bioorganic & medicinal chemistry letters. 2015 Sep 01;25(17):3564-8. [Content Brief]

[5]. Lou C, et al. 2',4'-Dihydroxychalcone-induced apoptosis of human gastric cancer MGC-803 cells via down-regulation of survivin mRNA. Toxicology in vitro : an international journal published in association with BIBRA. 2010 Aug;24(5):1333-7. [Content Brief]

[6]. Imdad S, et al. Identification of 2',4'-Dihydroxychalcone as an Antivirulence Agent Targeting HlyU, a Master Virulence Regulator in Vibrio vulnificus. Molecules. 2018 Jun 20;23(6):1492.
[Content Brief]

Calculators

Molaritätsrechner

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass

Konzentration

Volumen

Molecular Weight

Verdünnungsrechner

Konzentration _{(Stammlösung)} × Volumen _{(Stammlösung)} = Konzentration _{(Ziellösung)} × Volumen _{(Ziellösung)}

Konzentration _{(Stammlösung)}

Volumen _{(Stammlösung)}

Konzentration _{(Ziellösung)}

Volumen _{(Ziellösung)}

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

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2',4-Dihydroxychalcone

Biologische Aktivität

Chemical Information

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2',4-Dihydroxychalcone Related Classifications

Art. -Nr.: HY-141462