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| Other Sizes |
| Targets |
(-)-Menthone functions as an epigenetic modulator with the potential to inhibit fungal growth, potentially acting as an HDAC activator. It has antimicrobial activity, particularly against methicillin-resistant Staphylococcus aureus (MRSA). Its metabolite is (+)-Neomenthyl-β-d-glucoside.
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| ln Vitro |
In vitro, (-)-Menthone exhibits antimicrobial activity, including potent antibacterial effects against MRSA. It has been shown to inhibit mycelial growth of fungi. At a concentration of around 45 ppm, it showed 27.67% and 94.92% mortality against two strains of Anopheles stephensi mosquitoes. It functions as an epigenetic modulator.
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| ln Vivo |
In vivo, high doses of menthone have a good compensatory effect with significant reduction in DNA damage in sperm cells by reversing the adverse effect of ACV on the reproductive system in male rats. It also exhibits antimicrobial and potential anti-inflammatory effects.
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| Enzyme Assay |
Cell-free assays for (-)-Menthone: antimicrobial activity is assessed by agar diffusion or broth microdilution assays against bacterial and fungal strains. The compound is incubated with microorganisms, and growth inhibition is measured. IC50 or MIC values are calculated. Epigenetic modulation is assessed by measuring HDAC activity using fluorogenic substrates. The compound is incubated with HDAC enzymes, and deacetylase activity is measured.
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| Cell Assay |
Cellular assays for (-)-Menthone: microbial cells or mammalian cells are treated with (-)-Menthone at concentrations of 0.1-100 µM for 1-24 hours. Cell viability is measured. Antimicrobial effects are assessed by measuring microbial growth. In mammalian cells, DNA damage is assessed by comet assay or γ-H2AX staining. Epigenetic effects are evaluated by measuring histone acetylation levels by Western blot.
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| Animal Protocol |
In vivo animal studies for (-)-Menthone: male rat models are used to study its effects on the reproductive system. Animals are administered (-)-Menthone at high doses, and sperm cell DNA damage is assessed. Antimicrobial efficacy is evaluated in animal models of infection. Anti-inflammatory effects are assessed in models of inflammation.
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| ADME/Pharmacokinetics |
Metabolism / Metabolites
... Ketones (such as carvone and menthone) are reduced to secondary alcohols and then excreted as glucuronides. Menthone undergoes asymmetric reduction to generate neomenthol, which then combines with glucuronides to form menthol glucuronide. Pharmacokinetic properties of (-)-Menthone: it is a small, lipophilic molecule (MW 154.25) with expected good oral bioavailability and tissue penetration. It is metabolized to (+)-Neomenthyl-β-d-glucoside. It is soluble in DMSO (40 mg/mL). Storage: powder at -20°C for up to 3 years; in solvent at -80°C for 1 year. |
| Toxicity/Toxicokinetics |
Non-Human Toxicity Values
Oral LD50 in rats: 500 mg/kg Subcutaneous LD50 in mice: 2180 mg/kg Toxicity of (-)-Menthone: at high doses, it may cause effects on the reproductive system, though it has a compensatory effect on ACV-induced damage. It is generally recognized as safe (GRAS) as a food additive at low concentrations. It is for research use only and not for human therapeutic use. |
| References |
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| Additional Infomation |
(-)-Menthone is a cyclohexanone with methyl and isopropyl groups substituted at positions 5 and 2, respectively (2S,5R-stereoisomer). It is the enantiomer of (+)-menthone. Menthone has been reported in Minthostachys mollis, Swertia japonica, and other organisms with relevant data. Menthone is a metabolite found or produced in Saccharomyces cerevisiae.
(-)-Menthone is a research compound with applications in antimicrobial, antifungal, and epigenetic research. It is a major component of peppermint essential oil and is used in the fragrance and flavor industries. It is also used as an insect repellent. No clinical trials or FDA approvals have been reported. |
| Molecular Formula |
C10H18O
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|---|---|
| Molecular Weight |
154.25
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| Exact Mass |
154.136
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| CAS # |
14073-97-3
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| PubChem CID |
26447
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| Appearance |
Colorless to light yellow solid
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| Density |
0.89
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| Boiling Point |
207-210ºC
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| Melting Point |
-6 °C
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| Flash Point |
72ºC
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| Vapour Pressure |
0.256mmHg at 25°C
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| Index of Refraction |
n20/D 1.45(lit.)
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| LogP |
2.647
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
11
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| Complexity |
149
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| Defined Atom Stereocenter Count |
2
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| SMILES |
CC(C)[C@@H]1CC[C@@H](C)CC1=O
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| InChi Key |
NFLGAXVYCFJBMK-BDAKNGLRSA-N
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| InChi Code |
InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-9H,4-6H2,1-3H3/t8-,9+/m1/s1
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| Chemical Name |
(2S,5R)-5-methyl-2-propan-2-ylcyclohexan-1-one
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| Synonyms |
(-)-Menthone
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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) |
DMSO: 100 mg/mL (648.30 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (16.21 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (16.21 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (16.21 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.4830 mL | 32.4149 mL | 64.8298 mL | |
| 5 mM | 1.2966 mL | 6.4830 mL | 12.9660 mL | |
| 10 mM | 0.6483 mL | 3.2415 mL | 6.4830 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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