| Size | Price | Stock | Qty |
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| 500mg |
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| 1g |
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| Other Sizes |
| Targets |
The primary mechanism of action of Precocene I is the inhibition of juvenile hormone (JH) biosynthesis in insects. It exerts a cytotoxic action specifically on the corpora allata (CA) cells, which is mediated by oxidative bioactivation in vivo. This activation involves cytochrome P450 enzymes, which convert the relatively inert chromene into highly reactive intermediates, specifically the 3,4-epoxide. This reactive epoxide then alkylates cellular macromolecules, leading to irreversible necrosis and degeneration of the CA, effectively eliminating the source of JH.
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| ln Vitro |
Precocene I demonstrates potent anti-juvenile hormone activity in vitro. In bioassays against the Sunn pest (Eurygaster integriceps), it exhibited LC50 values of 15.4 ug/mL and 15 ug/mL against 2- and 5-day-old eggs, respectively. In filter paper bioassays with Formosan subterranean termites, a dose of 100 ug/dish significantly delayed the formation of presoldiers and soldiers. However, in acaricidal tests against Rhipicephalus annulatus, it showed very low adult mortality and fecundity inhibition.
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| ln Vivo |
In vivo animal studies have extensively investigated the hepatotoxicity of Precocene I in male Sprague-Dawley rats. A single intraperitoneal dose (300 mg/kg) caused extensive hepatic damage, characterized by severe centrolobular necrosis and a marked increase in serum glutamic pyruvic transaminase (GPT) levels. This toxicity is dose- and time-dependent, mediated by reactive metabolites formed via cytochrome P450. Moreover, in insects such as Oncopeltus fasciatus and Locusta migratoria, treatment leads to precocious metamorphosis, sterility, and reduced survival rates.
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| Enzyme Assay |
The in vitro metabolism of Precocene I is studied using liver microsomes from control and treated rats. Typically, liver microsomes (1-2 mg protein/mL) are incubated with the compound (usually 50-500 uM) in a Tris-HCl or phosphate buffer (pH 7.4) containing an NADPH-generating system (e.g., NADPH, glucose-6-phosphate, and glucose-6-phosphate dehydrogenase) at 37degC for 30-60 minutes. The reaction is terminated by adding an organic solvent, and metabolites are extracted and analyzed via HPLC or LC-MS. The major metabolites (80-90% of total) are the cis- and trans-3,4-diols of Precocene I, with a cis/trans isomer ratio of 1:2, which arise from the spontaneous hydrolysis of the reactive 3,4-oxide. 6-Hydroxyprecocene I is a minor metabolite (5-17% of total metabolites). CYP isoform-specific inhibitors can be co-incubated to determine the specific P450 enzymes involved.
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| Cell Assay |
For in vitro cell-based studies, precision-cut rat liver slices (approx. 200-300 um thickness) are prepared from male Sprague-Dawley rats and incubated in supplemented Williams' Medium E. The slices are treated with Precocene I (typically 25-500 uM) and co-incubated with or without CYP inhibitors (such as ABT or piperonyl butoxide) at 37degC under a 95% O2/5% CO2 atmosphere. Cytotoxicity is assessed by measuring the release of lactate dehydrogenase (LDH) into the medium. The effects are dose- and time-dependent, with ABT decreasing toxicity and increasing exposure to the parent compound.
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| Animal Protocol |
In vivo animal experiments are typically conducted in male Sprague-Dawley rats. A single intraperitoneal dose of Precocene I (50, 150, or 300 mg/kg) is administered in a vehicle such as corn oil or DMSO. Animals are sacrificed at various time points (e.g., 2, 4, 6, 12, and 24 hours) post-dose. Hepatotoxicity is evaluated by measuring plasma alanine aminotransferase (ALT/GPT) levels and by histopathological examination of liver sections for centrolobular necrosis. Liver glutathione (GSH) depletion is measured as an indicator of oxidative stress. The involvement of metabolic activation is confirmed by pre-treating animals with piperonyl butoxide or diethyl maleate before Precocene I administration.
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| ADME/Pharmacokinetics |
Precocene I is predicted to have a bioavailability score of 0.55 (SwissADME) and is classified as soluble in ESOL solubility class. The compound has limited water solubility (approx. 0.118 g/L) but is readily soluble in organic solvents such as ethanol and acetone, which facilitates its use in biological assays. It is metabolized primarily by cytochrome P450 enzymes to reactive epoxides that are responsible for both its allatocidal and toxic effects. In rats, the major pathway involves the formation of precocene I 3,4-oxide, which is either detoxified by epoxide hydrolase to form 3,4-diols or covalently binds to cellular macromolecules. Co-administration of CYP inhibitors like piperonyl butoxide increases the exposure to the parent compound while decreasing metabolite levels and toxicity, establishing the essential role of metabolic activation in its bioactivity.
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| Toxicity/Toxicokinetics |
Precocene I is classified as an acute oral toxicant (Acute Tox. 4 Oral). It is a hepatotoxic compound that causes severe centrolobular necrosis, glutathione depletion, and elevated transaminase levels in rats at a single i.p. dose of 300 mg/kg. The toxicity is mediated by reactive metabolites formed via cytochrome P450 metabolism, with the 3,4-oxide identified as the key hepatotoxic intermediate. Depletion of glutathione prior to treatment dramatically increases the severity of hepatic insult, while pre-treatment with cysteamine or the mixed-function oxidase inhibitor piperonyl butoxide blocks the damage. Its safety classification includes a GHS signal word of "Warning" with hazard classifications for acute toxicity. The compound has a flash point of 113degC (closed cup), a water hazard class (WGK) of 3, and is categorized as a combustible liquid (Storage Class 10).
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| Additional Infomation |
Precocene I is a chiral molecule, and the epoxidation reaction at the 3,4-double bond is highly stereospecific in certain biological systems, leading to the formation of specific enantiomers. It has been studied as an antifeedant against various insect species, including storage pests and aphids. Precocene I has moderate antifeedant activity against the Colorado potato beetle (Leptinotarsa decemlineata). The compound exhibits stability at room temperature but is sensitive to light and heat. It is available in 99% purity, with a density of 1.052 g/mL at 25degC and a boiling point of 68degC at 0.1 mmHg. Its refractive index (n20/D) is 1.56. The compound is considered for research use only and is not intended for human or veterinary applications. It is available for purchase from various chemical suppliers.
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| Molecular Formula |
C12H14O2
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| Molecular Weight |
190.24
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| Exact Mass |
190.099
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| CAS # |
17598-02-6
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| Related CAS # |
Precocene II; 644-06-4
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| PubChem CID |
28619
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| Appearance |
Typically exists as solids at room temperature
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| Density |
1.052 g/mL at 25 °C
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| Boiling Point |
68 °C0.1 mm Hg
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| Flash Point |
>230 °F
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| LogP |
3.3
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
14
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| Complexity |
232
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| SMILES |
CC1(C=CC2=C(O1)C=C(C=C2)OC)C
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| Chemical Name |
7-methoxy-2,2-dimethylchromene
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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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.2565 mL | 26.2826 mL | 52.5652 mL | |
| 5 mM | 1.0513 mL | 5.2565 mL | 10.5130 mL | |
| 10 mM | 0.5257 mL | 2.6283 mL | 5.2565 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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