| Targets |
(3E)-4,8-Dimethylnona-1,3,7-triene has no biological target as a drug. It is a plant signaling molecule. It is an insect semiochemical. DMNT is detected by olfactory receptors (ORs) in the antennae of insects. It acts as a repellent for some herbivores (e.g., aphids) and as an attractant for parasitoid wasps (e.g., Cotesia marginiventris) and predatory mites (e.g., Phytoseiulus persimilis). It induces a defensive response in neighboring plants, upregulating the expression of defense-related genes, including those involved in the jasmonic acid (JA) pathway. It is a key component of the indirect defense mechanism of plants against insect herbivory.
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| ln Vitro |
In vitro, (3E)-4,8-Dimethylnona-1,3,7-triene is not a drug and has no direct biological activity in mammalian systems. It is used in electroantennogram (EAG) assays to measure the olfactory response of insects. Insect antennae are excised and mounted between two electrodes. DMNT (10 ng to 100 ug) is puffed onto the antenna. The depolarization of the olfactory receptor neurons is recorded as a voltage change. The amplitude of the EAG response is dose-dependent. It also activates the expression of plant defense genes in plant tissue culture. In Arabidopsis cell cultures, DMNT (10-100 uM) induces the expression of the marker gene PDF1.2 (plant defensin) and other genes involved in the jasmonic acid pathway. The EC₅0 for gene induction is in the low micromolar range.
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| ln Vivo |
In vivo, (3E)-4,8-Dimethylnona-1,3,7-triene is an insect semiochemical used in agricultural research. It is not a drug. In field trials, DMNT (1-100 mg) dispensed from a slow-release lure is used to attract natural enemies (parasitoids and predators) for the biological control of aphids and mites in crop fields. It can also be used as a repellent to reduce herbivore colonization of plants. The compound is volatile and disperses quickly. It is not administered to animals. The compound is a natural product and is considered safe for use in research.
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| Enzyme Assay |
(3E)-4,8-Dimethylnona-1,3,7-triene is not an enzyme inhibitor. It is a volatile chemical. For analytical method development (AMV), the compound is used as a reference standard in GC-MS. For the analysis of HIPVs in plant headspace, a solid-phase microextraction (SPME) fiber (e.g., PDMS/DVB) is exposed to the air surrounding the plant for 1-4 h. The fiber is then inserted into the GC injector port. The compound is separated on a DB-5 column. The oven temperature program is 40degC (5 min) to 250degC at 10degC/min. Detection is by electron impact (EI) mass spectrometry. The compound is identified by comparing its mass spectrum and retention index (RI) to an authentic standard. Quantification is performed by spiking the sample with an internal standard (e.g., 1-bromo-4-fluorobenzene).
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| Cell Assay |
(3E)-4,8-Dimethylnona-1,3,7-triene is not used in standard cell-based assays for drug discovery. For toxicity screening, HepG2 or HEK293 cells are seeded in 96-well plates (1×10⁴ cells/well) and treated with DMNT (1-1000 uM) for 24-72 h. Cell viability is measured by MTT assay. The CC₅0 is expected to be > 1000 uM, indicating very low cytotoxicity. For insect cell cultures, Sf9 cells are used. The compound may cause a change in membrane potential. However, the primary use of DMNT is as a semiochemical, not in cell-based assays. It is not used in drug discovery.
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| Animal Protocol |
In vivo insect behavioral assays are used to study the effects of DMNT. For a Y-tube olfactometer assay, laboratory-reared female parasitic wasps (e.g., Cotesia marginiventris) are placed in the base of a Y-tube. One arm of the Y-tube is connected to a chamber containing a rubber septum with DMNT (10-100 ug), and the other arm contains a control chamber (solvent only). The number of wasps that enter each arm is counted over 10-15 min. A significant preference for the DMNT arm indicates that the compound is an attractant. For field trials, traps baited with DMNT (50-100 mg) are placed in a crop field. The number of natural enemies (e.g., ladybugs, lacewings) captured per trap is counted weekly. This protocol is for biological control research.
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| ADME/Pharmacokinetics |
(3E)-4,8-Dimethylnona-1,3,7-triene is a volatile terpene (MW 150.26, LogP ~ 4.6). It is not a drug, and its PK is not studied therapeutically. In plants, it is synthesized de novo via the terpenoid pathway. In the environment, it has a short half-life (hours) due to photodegradation and oxidation by ozone and hydroxyl radicals. For research use, it is stored as a liquid at -20degC. It is volatile and should be handled in a fume hood. It is soluble in ethanol and hexane. The compound is a reference standard for analytical chemistry and chemical ecology.
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| Toxicity/Toxicokinetics |
For (3E)-4,8-Dimethylnona-1,3,7-triene, hazard statements: H315 (Causes skin irritation), H319 (Causes serious eye irritation), H335 (May cause respiratory irritation), H226 (Flammable liquid and vapor). Signal word: Warning. Precautionary statements: P210 (Keep away from heat/sparks/open flames/hot surfaces-No smoking), P261 (Avoid breathing dust/fume/gas/mist/vapors/spray), P280 (Wear protective gloves/protective clothing/eye protection/face protection), P305+P351+P338 (IF IN EYES: Rinse cautiously with water for several minutes). For research use only.
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| References |
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| Additional Infomation |
(3E)-4,8-Dimethylnona-1,3,7-triene (DMNT; CAS# 19945-61-0) is a research-grade herbivore-induced plant volatile (HIPV) standard. It is not an FDA-approved drug. It is used as a reference standard for the analysis of plant volatiles by GC-MS, as a positive control in insect olfactometer assays, and in studies of tritrophic interactions (plant-herbivore-natural enemy) for biological control. For research use only, not for diagnostic or therapeutic applications.
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| Molecular Formula |
C11H18
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|---|---|
| Molecular Weight |
150.26
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| Exact Mass |
150.141
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| CAS # |
19945-61-0
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| PubChem CID |
6427110
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| Appearance |
Oil
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| Hydrogen Bond Donor Count |
0
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
11
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| Complexity |
166
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC(=CCC/C(=C/C=C)/C)C
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| InChi Key |
LUKZREJJLWEWQM-YRNVUSSQSA-N
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| InChi Code |
InChI=1S/C11H18/c1-5-7-11(4)9-6-8-10(2)3/h5,7-8H,1,6,9H2,2-4H3/b11-7+
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| Chemical Name |
(3E)-4,8-dimethylnona-1,3,7-triene
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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 Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
| 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 | 6.6551 mL | 33.2757 mL | 66.5513 mL | |
| 5 mM | 1.3310 mL | 6.6551 mL | 13.3103 mL | |
| 10 mM | 0.6655 mL | 3.3276 mL | 6.6551 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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