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| Other Sizes |
| Targets |
The primary target of 2-Naphthoxyacetic acid is the auxin receptor, for which it acts as an auxin antagonist. By binding to the auxin receptor, the compound impedes the binding of auxin, thereby disrupting the downstream signaling pathway of auxin and leading to the suppression of auxin-mediated plant growth and development. The compound also acts as an inhibitor of firefly luciferase with a potency of 40 μM. Additionally, it targets DUSP6 (dual specificity protein phosphatase 6). These targets make it valuable for studying auxin signaling pathways and plant developmental processes.
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| ln Vitro |
In vitro, 2-Naphthoxyacetic acid demonstrates auxin antagonist activity by binding to the auxin receptor and inhibiting auxin-dependent plant growth. It inhibits firefly luciferase with a potency of 40 μM. The compound is used in plant cell culture systems to study the effects of auxin signaling on cell elongation, fruit development, and other physiological processes. As a matrix effect agent, it is utilized in analytical methods such as synchronous fluorescence spectroscopy. These in vitro activities support its applications in plant physiology research and analytical chemistry.
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| ln Vivo |
In vivo, 2-Naphthoxyacetic acid functions as a plant growth regulator that promotes seed germination, early flowering, and improved fruit size and color in tomatoes and other crops. It is used in agricultural research to enhance fruit set and regulate growth in pineapples, strawberries, and tomatoes. The compound is applied to plants to modulate auxin responses and influence various developmental processes. Its in vivo effects are primarily studied in plant models to understand auxin signaling and its applications in crop improvement.
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| Enzyme Assay |
In vitro enzyme/receptor binding assays for 2-Naphthoxyacetic acid involve auxin receptor binding studies using plant membrane preparations or heterologously expressed auxin receptors. The compound is incubated with the receptor and labeled auxin (e.g., [3H]-IAA) at concentrations ranging from 0.1 nM-100 μM. Binding affinity is determined by competitive displacement curves. Luciferase inhibition assays are performed using firefly luciferase and ATP/luciferin substrates, with compound concentrations ranging from 0.1-1000 μM to determine IC50 values. All assays include appropriate controls and reference compounds such as IAA.
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| Cell Assay |
In vitro cell-based assays for 2-Naphthoxyacetic acid are conducted using plant cell cultures (e.g., tobacco BY-2 cells or Arabidopsis seedlings). Cells or tissues are treated with compound concentrations ranging from 0.1-100 μM for 24-72 hours. Auxin-responsive gene expression is measured by qPCR or reporter gene assays (e.g., DR5::GUS). Cell elongation and proliferation are assessed by measuring cell length and counting cell numbers. For luciferase inhibition studies, cell lysates or purified enzyme are used. Experiments include vehicle controls and positive controls (e.g., IAA or NAA).
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| Animal Protocol |
In vivo animal studies are not typically conducted with 2-Naphthoxyacetic acid, as it is a plant growth regulator rather than a therapeutic agent. However, plant studies are performed using various crop species including tomatoes, strawberries, and pineapples. The compound is applied as a foliar spray or soil drench at concentrations ranging from 10-100 ppm. Fruit set, seed germination, and flowering are monitored over several weeks. Each treatment group consists of 10-20 plants with appropriate vehicle controls. Data are analyzed using standard statistical methods.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of 2-Naphthoxyacetic acid in plants include its absorption through leaves and roots, followed by systemic distribution throughout the plant. As a small, polar molecule (MW 202.21, C12H10O3), it is readily taken up by plant tissues. The compound is metabolized through conjugation and degradation pathways typical of auxin analogs. In mammalian systems, it is an endogenous metabolite and would be expected to undergo hepatic metabolism and renal excretion. Detailed PK parameters in animals are limited, as the compound is primarily used for plant research.
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| Toxicity/Toxicokinetics |
Toxicological data for 2-Naphthoxyacetic acid indicate that it is generally considered safe for agricultural use at recommended concentrations. As an endogenous metabolite, it is expected to have a favorable safety profile. However, comprehensive toxicological studies in mammals are limited. The compound is intended for research use only and is not approved for diagnostic or therapeutic applications. As with all research chemicals, appropriate safety precautions should be taken during handling to avoid inhalation, ingestion, or skin contact.
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| Additional Infomation |
2-Naphthoxyacetic acid is a naphthoxyacetic acid.
2-Naphthoxyacetic acid is a phytohormone and auxin antagonist used primarily in plant physiology research and agricultural applications. It promotes seed germination, early flowering, and improved fruit size and color in crops such as tomatoes and strawberries. The compound is also an inhibitor of firefly luciferase (potency 40 μM) and a matrix effect agent in analytical chemistry. It is not intended for diagnostic or therapeutic use and is available for research purposes only. The compound serves as a valuable tool for studying auxin signaling pathways. |
| Molecular Formula |
C₁₂H₁₀O₃
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|---|---|
| Molecular Weight |
202.21
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| Exact Mass |
202.062
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| CAS # |
120-23-0
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| PubChem CID |
8422
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| Appearance |
White to off-white solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
388.7±15.0 °C at 760 mmHg
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| Melting Point |
151-154 °C(lit.)
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| Flash Point |
155.8±13.9 °C
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| Vapour Pressure |
0.0±0.9 mmHg at 25°C
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| Index of Refraction |
1.637
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| LogP |
2.57
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
15
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| Complexity |
227
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
RZCJYMOBWVJQGV-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C12H10O3/c13-12(14)8-15-11-6-5-9-3-1-2-4-10(9)7-11/h1-7H,8H2,(H,13,14)
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| Chemical Name |
2-naphthalen-2-yloxyacetic acid
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| Synonyms |
2Naphthoxyacetic acid; 2 Naphthoxyacetic acid
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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 (~494.54 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (12.36 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 (12.36 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 (12.36 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 | 4.9454 mL | 24.7268 mL | 49.4535 mL | |
| 5 mM | 0.9891 mL | 4.9454 mL | 9.8907 mL | |
| 10 mM | 0.4945 mL | 2.4727 mL | 4.9454 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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