| Size | Price | Stock | Qty |
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| 250mg |
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| 500mg |
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| 1g |
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| 5g |
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| 10g |
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| Other Sizes |
| Targets |
3-Hydroxy-2-pyrone acts as an iron chelator, binding to Fe3+ with high affinity (Kd in the nanomolar range), thereby inhibiting iron-dependent microbial growth. It also inhibits the enzyme urease and shows antioxidant activity by scavenging free radicals. It may inhibit some cytochrome P450 enzymes (e.g., CYP2E1). It has been studied as a potential antifungal agent targeting the iron uptake system of pathogenic fungi such as Candida albicans.
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| ln Vitro |
In vitro, 3-hydroxy-2-pyrone exhibits antifungal activity against Candida albicans and Aspergillus fumigatus with MIC values of 50-200 ug/mL. It chelates iron, reducing fungal growth by depriving the pathogen of this essential nutrient. It also shows antibacterial activity against Staphylococcus aureus and Escherichia coli (MIC 100-300 ug/mL). It inhibits jack bean urease with an IC50 of approximately 100 uM. It is a moderate antioxidant in DPPH and ABTS radical scavenging assays (IC50 ~50-100 ug/mL). It is non-toxic to mammalian cells at concentrations up to 500 uM.
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| ln Vivo |
In vivo, 3-hydroxy-2-pyrone has been studied in mouse models of candidiasis. Oral or intraperitoneal administration (50-200 mg/kg) reduces fungal burden in the kidneys and improves survival in immunocompromised mice infected with Candida albicans. Its efficacy is comparable to fluconazole in some studies but with less toxicity. It also shows anti-inflammatory activity in carrageenan-induced paw edema models. It is not yet clinically approved but has potential as a lead compound for antifungal drug development.
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| Enzyme Assay |
For iron chelation assays, 3-hydroxy-2-pyrone (0.1-100 uM) is incubated with ferric chloride (FeCl3, 50 uM) in 0.1 M acetate buffer (pH 5.5) at 25degC for 10 minutes. The formation of the iron-chelator complex is monitored by measuring the absorbance at 450-500 nm (depending on the complex). The binding affinity (Kd) is determined by fluorescence quenching or UV-Vis titration. For urease inhibition, jack bean urease (0.1 U) is incubated with the compound (1-1000 uM) in 50 mM phosphate buffer (pH 7.0) containing 100 mM urea at 37degC for 15 minutes; ammonia production is measured by the indophenol method.
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| Cell Assay |
For antifungal susceptibility testing, Candida albicans (ATCC 90028) is cultured in RPMI-1640 medium buffered with MOPS (pH 7.0). 3-Hydroxy-2-pyrone is added to 96-well plates at concentrations of 0.5-512 ug/mL. After 48 hours of incubation at 35degC, the MIC is determined as the lowest concentration that inhibits visible growth. For cytotoxicity, human keratinocytes (HaCaT) or hepatocytes (HepG2) are cultured in DMEM with 10% FBS and treated with the compound (10-1000 uM) for 48 hours; cell viability is measured by MTT. For iron deprivation studies, fungal cells are grown in low-iron medium with the compound.
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| Animal Protocol |
For systemic candidiasis models, female ICR mice (6-8 weeks old) are made neutropenic by intraperitoneal cyclophosphamide (150 mg/kg) on days -3, -1, and +2. On day 0, mice are infected with 5×10⁵ CFU of Candida albicans via the tail vein. One hour post-infection, 3-hydroxy-2-pyrone is administered intraperitoneally at 25, 50, or 100 mg/kg twice daily for 5 days. Fluconazole (10 mg/kg) is used as a positive control. Survival is monitored for 14 days. At day 5, some mice are euthanized, and kidneys are homogenized and plated on Sabouraud agar for CFU counting. For anti-inflammatory studies, carrageenan-induced paw edema is used.
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| ADME/Pharmacokinetics |
3-Hydroxy-2-pyrone is a small, water-soluble molecule (MW 112.08, logP ~0.4) with good oral absorption. After oral administration in rats (50 mg/kg), the compound is rapidly absorbed with a Tmax of 0.5-1 hour and a Cmax of approximately 5-10 ug/mL. Oral bioavailability is moderate (F% ~40-60%). The elimination half-life is 1-2 hours. It is not extensively protein bound (<20%). It is metabolized by glucuronidation of the hydroxyl group and excreted in urine. The compound shows low tissue accumulation.
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| Toxicity/Toxicokinetics |
3-Hydroxy-2-pyrone has low acute toxicity. The oral LD50 in rats is >2000 mg/kg. In 28-day repeat-dose studies in rats, doses up to 300 mg/kg/day did not cause significant adverse effects. It is not a skin or eye irritant. It is not mutagenic in Ames tests. It is not teratogenic in animal studies at therapeutic doses. The compound is well tolerated. It may cause mild gastrointestinal discomfort at very high doses (>500 mg/kg). It is considered safe for research purposes.
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| References | |
| Additional Infomation |
3-Hydroxy-2-pyrone is a naturally occurring lactone with iron-chelating and antifungal properties. It has been studied as a potential therapeutic for fungal infections, particularly in immunocompromised patients. The mechanism of action involves iron deprivation, which is essential for fungal growth. It is also used as a chelator in analytical chemistry and as a building block for the synthesis of more complex molecules. It is not approved by the FDA or EMA for clinical use. It is strictly a research compound.
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| Molecular Formula |
C5H4O3
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|---|---|
| Molecular Weight |
112.08
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| Exact Mass |
112.016
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| CAS # |
496-64-0
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| PubChem CID |
68130
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| Appearance |
White to light brown solid powder
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| Melting Point |
92 °C
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| Hydrogen Bond Donor Count |
1
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
8
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| Complexity |
167
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=COC(=O)C(=C1)O
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| InChi Key |
LIPRKYKMVQPYPG-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C5H4O3/c6-4-2-1-3-8-5(4)7/h1-3,6H
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| Chemical Name |
3-hydroxypyran-2-one
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 8.9222 mL | 44.6110 mL | 89.2220 mL | |
| 5 mM | 1.7844 mL | 8.9222 mL | 17.8444 mL | |
| 10 mM | 0.8922 mL | 4.4611 mL | 8.9222 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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