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| Targets |
Menthone exhibits a multi-target mechanism of action. Its antibacterial and antifungal activities are primarily due to its ability to disrupt microbial cell membranes. Its antiviral activity has been studied, particularly against herpes simplex virus (HSV). Menthone has been shown to have antioxidant properties, as it can scavenge free radicals and protect against DNA damage. In animal models, it demonstrates anti-inflammatory effects, reducing edema and pro-inflammatory cytokine production. Its antitumor activity is linked to its ability to induce apoptosis in cancer cells and inhibit DNA synthesis. Some studies suggest it may also inhibit NF-kappaB signaling, thereby reducing the expression of genes involved in inflammation and cell survival.
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| ln Vitro |
In vitro, menthone has been shown to have moderate to strong antibacterial activity against a range of both Gram-positive and Gram-negative bacteria, with MIC values typically in the range of 0.1-1.0 mg/mL. It is particularly effective against foodborne pathogens such as E. coli and S. aureus. It also demonstrates activity against fungi, including Candida albicans. Its antioxidant activity is measured using DPPH or ABTS radical scavenging assays. In cancer cell lines (e.g., HeLa, MCF-7), menthone can inhibit cell proliferation and induce apoptosis in a dose-dependent manner, with IC₅0 values around 100-500 uM. It has also been shown to inhibit the growth of the parasite Schistosoma mansoni in culture.
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| ln Vivo |
In vivo, menthone exhibits anti-inflammatory properties. In a mouse model of carrageenan-induced paw edema, administration of menthone (e.g., 50-200 mg/kg, IP) significantly reduced paw swelling, an effect comparable to the standard anti-inflammatory drug indomethacin. In a model of rheumatoid arthritis, it has been reported to reduce clinical scores and joint inflammation. Menthone has also shown activity in a model of Schistosoma mansoni infection, where treatment with menthone reduced the worm burden and egg count in infected mice. Its antitumor activity has been explored in a mouse model of skin cancer, where it reduced tumor incidence and multiplicity. The compound is typically dissolved in a suitable vehicle such as corn oil or DMSO and administered intraperitoneally or orally.
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| Enzyme Assay |
A typical non-cellular antioxidant assay for menthone is the DPPH radical scavenging assay. A 0.1 mM solution of DPPH in methanol is prepared. Menthone is dissolved in methanol at various concentrations (1-500 ug/mL). 100 uL of the DPPH solution is mixed with 100 uL of the menthone solution in a 96-well plate. The mixture is incubated in the dark at room temperature for 30 minutes. The decrease in absorbance is measured at 517 nm using a microplate reader. The percentage of inhibition is calculated. Ascorbic acid is used as a positive control. For its antimicrobial activity, a standard broth microdilution assay is performed in 96-well plates to determine the MIC against target bacteria, using standard CLSI guidelines. The colorimetric resazurin dye (Alamar Blue) can be added to determine the MIC as a color change from blue to pink.
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| Cell Assay |
A typical in vitro cell-based assay for menthone uses a cancer cell line such as HeLa (cervical cancer) or MCF-7 (breast cancer). Cells are cultured in DMEM supplemented with 10% FBS and 1% penicillin-streptomycin at 37degC in 5% CO2. Cells are seeded in 96-well plates at 5 × 103 cells/well and allowed to attach overnight. The next day, cells are treated with various concentrations of menthone (0, 50, 100, 200, 400, 800 uM) for 24, 48, and 72 hours. At each time point, cell viability is measured using the MTT assay. The IC₅0 (half-maximal inhibitory concentration) is calculated. For apoptosis detection, cells treated with menthone can be stained with Annexin V-FITC and PI and analyzed by flow cytometry. Caspase-3 activity can be measured using a colorimetric assay kit.
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| Animal Protocol |
An in vivo anti-inflammatory study is commonly performed for menthone. Adult male Swiss albino mice (20-25 g, n=6) are used. They are fasted overnight with free access to water. Carrageenan is dissolved in sterile saline (1% w/v). Menthone is dissolved in 0.5% carboxymethyl cellulose (CMC) or in corn oil. The test compound is administered intraperitoneally (IP) at doses of 50, 100, and 200 mg/kg, one hour before the induction of inflammation. A control group receives the vehicle only. Indomethacin (10 mg/kg) is used as a standard drug. Inflammation is induced by injecting 50 uL of 1% carrageenan solution into the subplantar region of the right hind paw. Paw volume is measured at 0, 1, 2, 3, and 4 hours after carrageenan injection using a plethysmometer. The percentage inhibition of edema is calculated for each group. The animals are then euthanized, and the paw tissue is collected for histological analysis.
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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. The pharmacokinetic (PK) properties of menthone are known due to its use in flavors and fragrances. After oral administration, menthone is rapidly absorbed from the gastrointestinal tract. It is primarily metabolized in the liver, where it is reduced to menthol (via 11-hydroxylation) and further conjugated with glucuronic acid. The elimination half-life in humans is approximately 2-4 hours. Menthone is also excreted in the urine as glucuronide conjugates and in the breath as carbon dioxide. Its high lipophilicity (logP ~2.8) suggests it will be widely distributed to tissues, including the brain. Due to its volatility, a significant portion may also be exhaled unchanged. |
| Toxicity/Toxicokinetics |
Non-Human Toxicity Values
Oral LD50 in rats: 500 mg/kg Subcutaneous LD50 in mice: 2180 mg/kg Menthone has been evaluated for safety as a food additive and is considered generally recognized as safe (GRAS) by the FDA when used in small quantities. The acute oral LD₅0 in rats is approximately 1,500 mg/kg, indicating moderate toxicity. It is not considered a skin or eye irritant at low concentrations, but high concentrations can cause irritation. It is not a carcinogen or mutagen. However, as a research chemical, standard safety precautions (gloves, lab coat, eye protection) should be used. Large doses may cause central nervous system depression and liver damage. |
| References |
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| Additional Infomation |
p-Menthane-3-one is a p-menthane monoterpene with a structure in which p-menthane is substituted at the 3-position with a carbonyl group. It is a plant metabolite and volatile oil component. p-Menthane-3-one has been reported in Osmanthus fragrans, Nepeta tenuifolia, and several other organisms with available data. See also: Menthonone, (+/-)- (Note moved here).
Menthone is not an approved drug for human therapeutic use, but it is a commonly used flavoring and fragrance agent. Its mechanism of action is broad and includes membrane disruption, antioxidant effects, and anti-inflammatory modulation. It has been studied for a variety of potential applications, including as a topical antiseptic, an anti-inflammatory agent, and a candidate for cancer therapy. No clinical trials have been registered for menthone as a drug. For research use only; not for human therapeutic or diagnostic use. |
| Molecular Formula |
C10H18O
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|---|---|
| Molecular Weight |
154.24932
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| Exact Mass |
154.135
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| CAS # |
10458-14-7
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| PubChem CID |
6986
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| Appearance |
Colorless to light yellow liquid
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| Density |
0.9±0.1 g/cm3
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| Boiling Point |
205.0±0.0 °C at 760 mmHg
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| Melting Point |
-6 °C
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| Flash Point |
72.8±0.0 °C
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| Vapour Pressure |
0.3±0.4 mmHg at 25°C
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| Index of Refraction |
1.443
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| LogP |
2.63
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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 |
0
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| SMILES |
O=C1C(C(C)C)CCC(C)C1
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| InChi Key |
NFLGAXVYCFJBMK-UHFFFAOYSA-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
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| Chemical Name |
5-methyl-2-propan-2-ylcyclohexan-1-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) |
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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