| Size | Price | |
|---|---|---|
| Other Sizes |
Purity: ≥98%
| Targets |
Insect olfactory receptors (anti-aggregation pheromone effects) - acts as an insect semiochemical.
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|---|---|
| ln Vitro |
In vitro studies on verbenone are primarily focused on its role as an insect semiochemical rather than as a pharmacological agent with direct effects on mammalian systems. As a naturally occurring terpene, verbenone has been studied for its effects on insect behavior, specifically its ability to interrupt the attraction of bark beetles to their aggregation pheromones. This anti-aggregation pheromone effect is mediated through insect olfactory receptors, which detect verbenone and trigger behavioral responses that disrupt aggregation and colonization. The compound's activity as a pheromone has been extensively studied in the context of forest pest management and bark beetle ecology.
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| ln Vivo |
In vivo studies have demonstrated that verbenone functions as an anti-aggregation pheromone in bark beetles, interrupting their attraction to aggregation pheromones and reducing tree colonization. Field studies in forests have shown that verbenone can be used as a semiochemical to protect trees from bark beetle infestations by disrupting the beetles' ability to aggregate and mass-attack trees. The compound has been studied in various bark beetle species including the mountain pine beetle (Dendroctonus ponderosae) and the southern pine beetle (Dendroctonus frontalis). Its effectiveness in reducing beetle attacks has made it a valuable tool in integrated pest management strategies for forest protection.
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| Enzyme Assay |
For insect behavioral assays, verbenone is tested in laboratory and field settings to assess its effects on bark beetle behavior. Laboratory assays include olfactometer studies where beetles are presented with a choice between aggregation pheromone alone and aggregation pheromone combined with verbenone. The attraction of beetles to the different treatments is recorded, and the reduction in attraction is calculated. Field studies involve deploying verbenone-releasing devices in forests and monitoring beetle trap catches, tree attacks, and colonization rates. The compound's effectiveness as an anti-aggregation pheromone is quantified by comparing beetle behavior in treated and untreated areas.
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| Cell Assay |
Cellular assays for verbenone are not commonly performed, as the compound's primary biological activity is as an insect semiochemical rather than as a pharmacological agent with effects on mammalian cells. In insect physiology studies, olfactory receptor neurons from bark beetles may be used to study the electrophysiological responses to verbenone. Single sensillum recording or electroantennography (EAG) techniques are used to measure the response of antennal olfactory receptors to verbenone and other semiochemicals. These studies help elucidate the molecular basis of pheromone perception and the mechanisms of anti-aggregation pheromone effects.
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| Animal Protocol |
In vivo efficacy of verbenone is evaluated in field studies in forests and in laboratory behavioral assays with bark beetles. For field studies, verbenone-releasing devices (such as pouches, flakes, or beads) are deployed in forest stands, and beetle attacks on trees are monitored. Tree mortality, pitch tube formation, and beetle gallery construction are assessed. Trap catch studies are conducted using baited traps with aggregation pheromone and verbenone to measure the reduction in beetle attraction. The compound's effectiveness in reducing tree mortality and protecting forests from bark beetle infestations has been demonstrated in numerous field studies across different bark beetle species and forest types.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of verbenone have been studied in the context of its environmental fate and persistence rather than for pharmaceutical applications. As a volatile terpene ketone, verbenone is released into the atmosphere where it undergoes photochemical degradation and can be transported over long distances. Its half-life in the environment depends on factors such as temperature, sunlight, and atmospheric chemistry. In biological systems such as insects, verbenone is detected by olfactory receptors and metabolized by detoxification enzymes. Studies on its metabolism and clearance in insects help understand the duration of its behavioral effects.
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| Toxicity/Toxicokinetics |
Toxicological evaluation of verbenone is conducted in the context of its use as a forest pest management tool. The compound is generally considered to have low toxicity to mammals and non-target organisms, as it is a naturally occurring terpene found in plants. Standard toxicology assessments include acute toxicity studies in mammals, birds, and aquatic organisms, as well as environmental fate and persistence studies. The compound's favorable environmental profile supports its use in integrated pest management programs. As a naturally occurring compound with low toxicity, verbenone is considered safe for use in forest protection applications when used according to established guidelines.
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| References |
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| Additional Infomation |
(S)-(-)-Verbenaone is a 4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one in which both chiral centers are in the S configuration. It has expectorant properties. It is the enantiomer of (R)-(+)-Verbenaone. (-)-Verbenaone has been reported in Artemisia judaica, Artemisia annua, and other organisms with relevant data.
Verbenone is a naturally occurring terpene ketone that functions as an anti-aggregation pheromone in bark beetles, interrupting their attraction to aggregation pheromones and reducing tree colonization. The compound is used in forest pest management as a semiochemical to protect trees from bark beetle infestations, particularly in the context of integrated pest management programs. Its mechanism of action involves activation of olfactory receptors in bark beetles that detect verbenone and trigger behavioral responses that disrupt aggregation and mass-attack behavior. Verbenone is not used as a drug or therapeutic agent and is not approved for human use. It is primarily used in ecological and entomological research and in forest protection applications. |
| Molecular Formula |
C10H14O
|
|---|---|
| Molecular Weight |
150.2176
|
| Exact Mass |
150.104
|
| CAS # |
1196-01-6
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| PubChem CID |
92874
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| Appearance |
Colorless to light yellow liquid
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| Density |
1.0±0.1 g/cm3
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| Boiling Point |
227.5±0.0 °C at 760 mmHg
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| Flash Point |
85.0±0.0 °C
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| Vapour Pressure |
0.1±0.4 mmHg at 25°C
|
| Index of Refraction |
1.494
|
| LogP |
1.97
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| Hydrogen Bond Donor Count |
0
|
| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
0
|
| Heavy Atom Count |
11
|
| Complexity |
248
|
| Defined Atom Stereocenter Count |
2
|
| SMILES |
O=C1C([H])=C(C([H])([H])[H])[C@]2([H])C([H])([H])[C@@]1([H])C2(C([H])([H])[H])C([H])([H])[H]
|
| InChi Key |
DCSCXTJOXBUFGB-JGVFFNPUSA-N
|
| InChi Code |
InChI=1S/C10H14O/c1-6-4-9(11)8-5-7(6)10(8,2)3/h4,7-8H,5H2,1-3H3/t7-,8+/m0/s1
|
| Chemical Name |
(1S,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one
|
| 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)
|
| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~665.69 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (16.64 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 (16.64 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 (16.64 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 | 6.6569 mL | 33.2845 mL | 66.5690 mL | |
| 5 mM | 1.3314 mL | 6.6569 mL | 13.3138 mL | |
| 10 mM | 0.6657 mL | 3.3285 mL | 6.6569 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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