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| Other Sizes |
| Targets |
Ketoisophorone does not have a defined biological or pharmacological target. It is not known to interact with specific receptors, enzymes, or cellular pathways in a therapeutic context. As a chemical intermediate and solvent, its biological effects are primarily related to its chemical properties rather than specific molecular interactions. It may cause irritation and other effects upon exposure, but it does not have a characterized mechanism of action as a drug. It is not used in pharmacological research as a tool compound.
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| ln Vitro |
In Vitro: Ketoisophorone (20 mg per 100 mL culture) was incubated with suspension cultured cells of Marchantia polymorpha and Nicotiana tabacum for 7 days. The biotransformation yielded five chiral products: (6R)-levodione (2), (4R,5S)-4-hydroxy-3,3,5-trimethylcyclohexanone (3), (4R,6R)-actinol (4), (4R)-hydroxyisophorone (5), and (4S)-phorenol (6). Conversion yields for M. polymorpha: 45% (2), 20.5% (3), 14.8% (4), 4.8% (5), 13.8% (6). For N. tabacum: 41.6% (2), 38.8% (3), 7.4% (4), 7.2% (5), 3.7% (6). Enantiomeric excess (e.e.) for actinol (4) was >99% in both plant species; for (6R)-levodione: 76.4% (M. polymorpha) and 77% (N. tabacum); for (4R,5S)-3: 17.5% and 56.6%; for (4R)-5: 55.7% and 9.6%; for (4S)-6: >99% and 9.1%, respectively [1].
Time-course study with M. polymorpha showed that ketoisophorone was initially reduced to (6R)-levodione (2), which was further reduced to compounds 3 and 4; direct carbonyl reduction of the substrate also produced compounds 5 and 6 [1]. Ketoisophorone does not exhibit significant in vitro biological activity relevant to pharmacology. It is not known to inhibit specific enzymes, modulate receptor activity, or affect cellular signaling pathways. Its primary applications are in industrial chemistry as a solvent and intermediate rather than in biological research. In vitro studies have focused on its chemical properties and potential toxicity rather than pharmacological activity. It is not used in cell-based assays for studying signaling pathways or therapeutic endpoints. |
| ln Vivo |
Ketoisophorone is not a therapeutic agent and does not have in vivo pharmacological activity. It is not administered to animals for therapeutic purposes. Its in vivo effects are primarily toxicological and relate to its use as an industrial chemical. Upon exposure, it may cause irritation to skin, eyes, and respiratory tract. Systemic effects would be related to its chemical properties rather than specific pharmacological activity. It is not used in animal models for studying disease or therapeutic efficacy.
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| Enzyme Assay |
In vitro assays for ketoisophorone are primarily conducted for safety assessment and regulatory compliance rather than pharmacological evaluation. Cytotoxicity assays using mammalian cell lines (e.g., HepG2, CHO, or 3T3 cells) involve exposing cells to various concentrations of the compound (typically 0.1-1000 μg/mL) for 24-48 hours, with cell viability assessed by MTT or neutral red uptake assays. Membrane integrity is evaluated by LDH release assays. For genotoxicity screening, the Ames test (bacterial reverse mutation assay) is performed using Salmonella typhimurium strains with and without metabolic activation, following OECD Test Guideline 471. Chemical characterization includes spectrophotometric analysis at characteristic wavelengths.
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| Cell Assay |
Cell Assay: Suspension cultured cells of Marchantia polymorpha (subcultured every 3 weeks in MSK‑II medium containing 2% glucose, 0.1% myo-inositol, 10 mM 2,4‑D) and Nicotiana tabacum (cultured in Murashige and Skoog medium with 1% sucrose, no auxin) were used. For biotransformation, approximately 20 g fresh weight of cells in 100 mL medium were treated with ketoisophorone (20 mg dissolved in 0.2 mL DMSO). Cultures were incubated at 25 °C on a rotary shaker (110 rpm for M. polymorpha, 75 rpm for N. tabacum) under illumination (4000 lx). After 7 days, cells and medium were separated by suction filtration. The medium was extracted with diethyl ether, concentrated, and products were purified by preparative TLC (diethyl ether/hexane, 3:1) followed by Sephadex LH‑20 chromatography. Conversion yields were determined by GLC. Product structures were identified by NMR and GC‑MS. For time‑course experiments, flasks were harvested at regular intervals, and conversion was determined by GLC peak ratios [1].
Cell-based assays for ketoisophorone are typically conducted to assess its potential for cytotoxicity and irritation rather than therapeutic activity. Human keratinocyte or fibroblast cell lines are exposed to the compound at various concentrations for 24-72 hours. Cell viability is measured using MTT, Alamar Blue, or neutral red uptake assays. Inflammatory responses may be evaluated by measuring IL-1α, IL-6, and TNF-α release via ELISA. Skin irritation potential is assessed using reconstructed human epidermis models (e.g., EpiSkin) according to OECD Test Guideline 439, where tissue viability after compound exposure is compared to negative and positive controls. The compound's effects on cell membrane integrity can be assessed by LDH release assays. |
| Animal Protocol |
In vivo animal studies for ketoisophorone are primarily toxicological and conducted according to regulatory guidelines for industrial chemicals. OECD Test Guideline 401 (Acute Oral Toxicity) involves administering the compound to rats by oral gavage at graded doses and monitoring for mortality and clinical signs over 14 days to determine the LD₅₀. OECD TG 402 (Acute Dermal Toxicity) and TG 403 (Acute Inhalation Toxicity) assess other routes of exposure. For repeated-dose toxicity, rats are administered ketoisophorone by oral gavage for 28 or 90 days, with histopathological examination of organs, hematology, clinical chemistry, and urinalysis. Genotoxicity is assessed using the Ames test (OECD TG 471) and micronucleus test (OECD TG 474). Reproductive toxicity studies may also be conducted.
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| ADME/Pharmacokinetics |
Ketoisophorone does not have established pharmacokinetic properties in the context of therapeutic use. As a small lipophilic molecule (log P ~1.5-2.0), it would be expected to be absorbed through the gastrointestinal tract and distributed to tissues. Metabolism likely occurs via cytochrome P450-mediated oxidation and conjugation, with subsequent renal excretion. However, specific pharmacokinetic parameters have not been characterized as this is not a therapeutic agent. Its chemical properties are well-documented for industrial applications.
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| Toxicity/Toxicokinetics |
Ketoisophorone is classified as an industrial chemical with potential toxicity upon exposure. It may cause skin, eye, and respiratory tract irritation. At high concentrations, it may cause central nervous system depression, and effects on liver and kidneys may occur. It is not classified as a carcinogen or mutagen based on available data, but comprehensive toxicological data may be limited. Proper handling procedures should be followed, including the use of personal protective equipment and adequate ventilation. The compound is not intended for human or veterinary therapeutic use.
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| References | |
| Additional Infomation |
2,6,6-Trimethyl-2-cyclohexene-1,4-dione is a type of cyclohexene ketone compound. It has been reported that 2,6,6-trimethyl-2-cyclohexene-1,4-dione exists in tea plants (Camellia sinensis), Artemisia judaica, and other organisms with relevant data.
Additional Info: Ketoisophorone is a prochiral compound used as a starting material for chiral synthesis. This study reports for the first time its biotransformation by cultured plant cells (Marchantia polymorpha and Nicotiana tabacum), producing chiral hydroxycyclohexanone derivatives. Compounds 3 and 4 are reported here as novel biotransformation products from microbial/plant transformation. The stereospecific reductions (C=C and C=O) by plant cells offer a potential biocatalytic route to optically pure intermediates for carotenoid and flavor synthesis [1]. Ketoisophorone (CAS# 1125-21-9) is an organic compound with the molecular formula C₉H₁₂O₂. It is a cyclic ketone and a derivative of isophorone. It is primarily used as a chemical intermediate in organic synthesis and as a starting material for the production of fragrances, flavors, and pharmaceuticals. It is also used as a solvent and in the production of polymers. It is not a pharmaceutical agent and does not have therapeutic applications. It is not approved for human or veterinary use. This compound is for research and industrial use only. Standard safety precautions should be followed when handling this chemical. |
| Molecular Formula |
C9H12O2
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|---|---|
| Molecular Weight |
152.19
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| Exact Mass |
152.083
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| CAS # |
1125-21-9
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| PubChem CID |
62374
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| Appearance |
Light yellow to yellow liquid
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| Density |
1.0±0.1 g/cm3
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| Boiling Point |
214.2±0.0 °C at 760 mmHg
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| Melting Point |
26-28 °C(lit.)
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| Flash Point |
96.1±0.0 °C
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| Vapour Pressure |
0.2±0.4 mmHg at 25°C
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| Index of Refraction |
1.469
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| LogP |
0.76
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
11
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| Complexity |
246
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O=C1C(C([H])([H])[H])=C([H])C(C([H])([H])C1(C([H])([H])[H])C([H])([H])[H])=O
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| InChi Key |
AYJXHIDNNLJQDT-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C9H12O2/c1-6-4-7(10)5-9(2,3)8(6)11/h4H,5H2,1-3H3
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| Chemical Name |
2,6,6-trimethylcyclohex-2-ene-1,4-dione
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| Synonyms |
Keto isophorone OxopholoneKetoisophorone Oxophorone 6-Oxoisophorone
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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 (~657.07 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (16.43 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 (16.43 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 (16.43 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 | 6.5707 mL | 32.8537 mL | 65.7073 mL | |
| 5 mM | 1.3141 mL | 6.5707 mL | 13.1415 mL | |
| 10 mM | 0.6571 mL | 3.2854 mL | 6.5707 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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