| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
|
||
| 10mg | |||
| 100mg | |||
| Other Sizes |
| Targets |
(+)-Isomenthone targets transient receptor potential (TRP) channels, particularly TRPM8 (menthol receptor) and possibly TRPA1, producing cooling and sensory effects. It may also modulate GABAergic and serotonergic systems. It interacts with bacterial membranes, causing disruption and antimicrobial activity. As an antioxidant, it scavenges free radicals. Its anti-inflammatory action is mediated through inhibition of prostaglandin synthesis and NF-κB.
|
|---|---|
| ln Vitro |
In vitro studies have shown that (+)-Isomenthone exhibits antimicrobial activity against various bacteria (S. aureus, E. coli) and fungi (C. albicans) with MIC values of 100-500 μg/mL. It demonstrates DPPH radical scavenging activity with IC₅₀ ~ 200 μM. It reduces LPS-induced NO production in macrophages (IC₅₀ ~ 50 μM). The compound also activates TRPM8 channels in HEK293 cells, eliciting calcium influx (EC₅₀ ~ 30 μM). It shows cytotoxicity against some cancer cell lines at high concentrations (>100 μM).
|
| ln Vivo |
In vivo studies are limited. In mice, topical application of (+)-Isomenthone (5-10%) reduces carrageenan-induced paw edema, indicating anti-inflammatory activity. In an insect repellent assay, it shows moderate repellency against mosquitoes. In a rat model, oral administration (100 mg/kg) produced a mild sedative effect, possibly via GABA modulation. However, most uses are in flavor and fragrance, not therapeutic.
|
| Enzyme Assay |
In vitro enzyme/receptor binding (non-cell) assays for (+)-Isomenthone: For antimicrobial, broth microdilution MIC determination. Antioxidant: DPPH, ABTS, and FRAP assays. Anti-inflammatory: COX-1/COX-2 inhibition using colorimetric kits (e.g., Cox inhibitor screening kit). TRPM8 activation can be assessed using calcium flux assays in cells, but for cell-free, receptor binding with ³H-icilin can be used for competition. However, binding assays are not well-established.
|
| Cell Assay |
For in vitro cell-based assays, HEK293 cells expressing TRPM8 are loaded with Fluo-4 AM, and calcium influx induced by (+)-Isomenthone is measured by fluorescence. Macrophages (RAW 264.7) are stimulated with LPS (1 μg/mL) and treated with compound (10-100 μM); NO (Griess) and cytokines (ELISA) measured. Cytotoxicity: MTT assay. Antimicrobial: bacterial suspension treated with compound, and OD600 monitored.
|
| Animal Protocol |
In vivo animal studies: Anti-inflammatory: mice are given carrageenan in paw, and compound is applied topically or given orally (50-200 mg/kg) 1 hour before; paw volume measured. For insect repellent, arm-in-cage test with mosquitoes. For sedation, mice are given compound and locomotor activity measured in open field. Toxicity: acute oral LD₅₀ in rats is estimated >2000 mg/kg.
|
| ADME/Pharmacokinetics |
(+)-Isomenthone (MW 154.25, formula C₁₀H₁₈O) is a volatile oil, insoluble in water, soluble in ethanol and oils. After ingestion, it is metabolized by cytochrome P450 to menthone and other metabolites, conjugated and excreted in urine. Half-life short (~1-2 h). It is rapidly eliminated.
|
| Toxicity/Toxicokinetics |
In acute toxicity, the oral LD₅₀ in rats is ~1-2 g/kg, indicating low toxicity. Skin and eye irritation may occur at high concentrations. No carcinogenicity reported. It is considered safe as a flavor additive (GRAS).
|
| References | |
| Additional Infomation |
(+)-Ismenthone is an isomenthone. It is the enantiomer of (-)-isomenthone. (+)-Isomenthone has been reported in Clinopodium douglasii, Mentha arvensis, and other organisms with relevant data. See also: Isomenthone, (+/-)- (Note moved to).
(+)-Isomenthone is a natural mint ketone used in flavor and fragrance. It has mild biological activities. It is a chiral compound, the (1S,4S)-enantiomer. It is used as a research chemical and a standard in essential oil analysis. Not a drug. |
| Molecular Formula |
C10H18O
|
|---|---|
| Molecular Weight |
154.24932
|
| Exact Mass |
154.136
|
| CAS # |
1196-31-2
|
| Related CAS # |
(-)-Isomenthone;18309-28-9;(±)-Isomenthone;491-07-6
|
| PubChem CID |
70962
|
| Appearance |
Colorless to light yellow liquid
|
| Density |
0.881±0.06 g/cm3
|
| Boiling Point |
204 °C
|
| LogP |
2.647
|
| Hydrogen Bond Donor Count |
0
|
| Hydrogen Bond Acceptor Count |
1
|
| Rotatable Bond Count |
1
|
| Heavy Atom Count |
11
|
| Complexity |
149
|
| Defined Atom Stereocenter Count |
2
|
| SMILES |
C[C@@H]1CC[C@H](C(C)C)C(=O)C1
|
| InChi Key |
NFLGAXVYCFJBMK-RKDXNWHRSA-N
|
| 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
|
| Chemical Name |
(2R,5R)-5-methyl-2-propan-2-ylcyclohexan-1-one
|
| HS Tariff Code |
2934.99.9001
|
| 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)
|
| Solubility (In Vitro) |
DMSO : ≥ 100 mg/mL (~648.30 mM)
|
|---|---|
| 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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
