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Atropic acid is an organic compound with the chemical formula C17H14O4, CAS 492-38-6, and a molecular weight of 282.29 g/mol. Exists in the form of a white crystalline solid. Its crystals are usually needle shaped or plate shaped, with a typical acidic taste of organic acids. It can be dissolved in a variety of organic solvents, such as ethanol, acetone and dichloromethane.
The solubility depends on the properties of the solvent. Its solubility in water is relatively low, approximately 1-10 mg/L. However, in many organic solvents, such as ethanol and acetone, it has good solubility. It is an organic acid, therefore it has obvious acidity. It can react with alkali in aqueous solution to produce salts and release hydrogen ions. It is one of the important intermediates for synthesizing various drugs.
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C.F |
C9H8O2 |
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E.M |
148 |
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M.W |
148 |
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m/z |
148 (100.0%), 149 (9.7%) |
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E.A |
C, 72.96; H, 5.44; O, 21.60 |
Mechanism of Action and Application Scenarios
Mechanism of Action and Application Scenarios of 2-Phenylacrylic Acid (Cinnamic Acid) as a Plant Growth Regulator
Mechanism of Action
Hormone Balance Regulation-2-Phenylacrylic acid optimizes plant growth cycles by regulating the synthesis and metabolism of endogenous plant hormones (such as auxin, cytokinin, and ethylene). For example:Promoting Cell Division and Elongation: In wheat trials, foliar application of a 0.1% cinnamic acid solution increased leaf area by 15%-20% and root dry weight by 25%, attributed to its enhancement of cytokinin activity.Regulates Flowering and Fruit Set: Cinnamic acid application during tomato flowering increased fruit set by 25%-30%, linked to enhanced pollen tube elongation and ovary development.Enhanced Stress Tolerance-Cinnamic acid induces stress-related proteins to improve tolerance against drought, salinity, and low temperatures.
Drought stress: Under simulated drought conditions, cinnamic acid-treated corn seedlings exhibited a 40% higher survival rate than controls, with stable leaf water content maintained.Salinity stress: In soils with 0.3%-0.5% salt content, combined application of atropic acid and humic acid increased corn emergence rate from 45% to 78% and boosted biomass accumulation by 65%.Photosynthesis Optimization-Cinnamic acid enhances photosynthetic efficiency by increasing chlorophyll content and photosystem II activity:Low-light Adaptation: Under low-light conditions, treated cucumber seedlings exhibited a 22% increase in net photosynthetic rate and significantly enhanced carbon assimilation capacity.
Chlorophyll Synthesis: Cinnamic acid treatment of tomato leaves increased chlorophyll a+b content by 18% and boosted photosystem activity.Antibacterial and Insecticidal Effects-Cinnamic acid induces systemic acquired resistance (SAR) in plants, inhibiting pathogen growth:Fungal Diseases: Exhibits 40%-50% efficacy against powdery mildew and gray mold. When applied at the onset of strawberry gray mold, disease index was 18 percentage points lower than the chemical treatment group.Insect Repellency: Repels pests like aphids and spider mites, reducing pesticide use by 30%-50%.
It can be used to synthesize anticholinergic drugs, such as Atropine and scopolamine. These drugs are often used to treat ophthalmic diseases, gastrointestinal spasms, and other neurological related diseases. Used as an additive in the food industry. It has antibacterial and antioxidant properties, which can extend the shelf life of food and improve the stability of the product.
As an organic compound, It has multiple uses, so researchers have conducted in-depth research on its synthesis route. Below are several common methods:
Chemical equation:
C17H21NO4 + HNO3 + HClO4 (oxidant) → C9H8O2
1. Dissolve anisodamine in hydrochloric acid (HCl) to obtain a solution.
2. Add a certain amount of nitric acid (HNO3) and Perchloric acid (HClO4) into the solution as oxidants.
3. Heat the solution at an appropriate temperature, usually between 40 and 60 degrees Celsius.
After the reaction is completed, completely convert the anisodamine in the solution into product.
5. Obtain pure products through crystallization purification or recrystallization.
Chemical equation:
C4H2O3 + H2SO4 (catalyst) → C9H8O2
1. First, dissolve an appropriate amount of maleic anhydride in dry dichloromethane (CH2Cl2) or tetrahydrofuran (THF).
2. Add a small amount of acidic catalysts such as sulfuric acid (H2SO4) or phosphoric acid (H3PO4) to the solution.
3. Stir the reactants at room temperature for a period of time, usually taking several hours to several days.
4. After the reaction is completed, filter the solution to remove any precipitates generated, and neutralize the acidity of the solution with a saturated sodium carbonate solution.
5. Extract the organic phase and purify it through distillation or crystallization to obtain a pure atropic acid product.
Application Scenarios
Crop Yield Enhancement and Quality Improvement
Rice: Spraying a 50-100 mg/L cinnamic acid solution during tillering increases effective panicle number by 12%, raises thousand-grain weight by 8%, and boosts yield by 15%-18%.
Wheat: Application during regreening increases tiller number by 15%-20% and grain number per ear by 10%-15%.
Corn: Application during the large whorl stage increases ear length by 5%-8% and reduces tip-drying by 20%-30%.
Economic Crop Profitability Enhancement
Cotton: Application during the budding stage increases bolls per plant by 20%, extends fiber length by 0.8-1.2 mm, and boosts fiber strength by 15%.
Rapeseed: Application during pod development increases pod count by 18%-25% and oil content by 1.5-2.0 percentage points.
Tobacco: Post-topping application expands upper leaf area by 10%-15%, reduces nicotine content by 0.5%-1.0%, and significantly improves quality.
Optimized Fruit Tree Production
Apple: Application during flowering increases fruit set by 25%-30% and raises soluble solids content by 1.5-2.0 percentage points.Citrus: Application during fruit enlargement increases fruit diameter by 8%-12%, reduces peel thickness by 10%-15%, and enhances storage tolerance.Grapes: Application during color change stage boosts color index by 20%-25%, optimizes sugar-acid ratio, and enhances flavor quality.
Vegetable Quality Improvement
Tomatoes: Application during fruiting stage increases individual fruit weight by 10%-15% and elevates vitamin C content by 8%-12%.
Cucumbers: After 2-3 consecutive applications, deformed fruit rate decreases by 30%-40% with significantly improved marketability.Peppers: Application during peak fruiting stage increases pungency (Scoville units) by 15%-20%, boosting market value.
Stress Tolerance Enhancement
Saline-alkali soil remediation: In soils with 0.3%-0.5% salt content, combined application of cinnamic acid and humic acid elevates corn germination rate from 45% to 78%.Cold Protection: When applied to winter greenhouse cucumbers, electrolyte leakage in leaves at 5°C decreased by 30%, with enhanced cell membrane stability.Drought Recovery: When applied before rewatering after drought, corn leaf regrowth accelerated by 40%-50% compared to the control group.
Scope of international sales channels
Direct model-Large suppliers such as Sigma Aldrich and Merck typically adopt a direct sales model, establishing direct contact with customers, understanding their needs, and providing customized products and services. This model helps suppliers better control product quality and sales channels, and improve customer satisfaction. Some suppliers also conduct direct sales through their online sales platforms, where customers can browse product information, place orders, and enjoy convenient logistics and delivery services. This model reduces sales costs and improves sales efficiency.
Distribution model-Many suppliers choose to collaborate with local distributors and agents to bring their products to market through their sales networks. Distributors and agents usually have rich market experience and customer resources, which can help suppliers quickly open up the market and increase product awareness.Some large suppliers also set up regional distribution centers in major global markets, responsible for product sales and logistics distribution in the region. This model helps suppliers better manage inventory, improve logistics efficiency, and reduce transportation costs.
plant growth regulators
Atropic acid (also known as cinnamic acid) has significant applications in the field of plant growth regulators, with the following mechanisms of action and effects:
Core Mechanism of Action
(1) Hormone Balance Regulation
2-Phenylacrylic acid promotes cell division and elongation by regulating the synthesis and distribution of endogenous plant hormones (such as auxin and cytokinin). For instance, in wheat trials, foliar application of a 0.1% cinnamic acid solution increased leaf area by 15%-20% and root dry weight by 25%, significantly enhancing nutrient uptake capacity.
In simulated drought tests, cinnamic acid-treated corn seedlings exhibited a 40% higher survival rate than controls, with stable leaf water content maintained.(3) Optimized Photosynthesis-Cinnamic acid enhances photosynthetic efficiency by increasing chlorophyll content (experiments showed an 18% rise in chlorophyll a+b in tomato leaves) and photosystem II activity. Under low-light conditions, treated cucumber seedlings exhibited a 22% increase in net photosynthetic rate and significantly enhanced carbon assimilation capacity.
Specific Application Scenarios
(1) Crop Yield and Quality Enhancement-Grain Crops: Applying cinnamic acid (50-100 mg/L) during rice tillering increases effective panicle number by 12%, raises thousand-grain weight by 8%, and boosts yield by 15%-18%.Cash Crops: Application during cotton budding stage increases bolls per plant by 20%, extends fiber length by 0.8–1.2 mm, and boosts fiber strength by 15%.Fruit Trees: Spraying during apple blossom stage improves fruit set by 25–30% and increases soluble solids content in fruit by 1.5–2.0 percentage points.
(2) Stress Tolerance Enhancement-Saline-alkali soil remediation: In soils with 0.3%-0.5% salt content, combined application of cinnamic acid and humic acid boosts corn germination rate from 45% to 78% and increases biomass accumulation by 65%.Cold protection: Winter greenhouse cucumbers treated with the spray exhibit a 30% reduction in leaf electrolyte leakage at 5°C, indicating significantly enhanced cell membrane stability.(3) Auxiliary Pest and Disease Control-Cinnamic acid induces systemic acquired resistance (SAR) in plants, achieving 40%-50% efficacy against fungal diseases like powdery mildew and gray mold. For instance, early-stage application on strawberry gray mold reduced disease index by 18 percentage points compared to chemical treatments.
Key Application Techniques
(1) Concentration Control-Recommended foliar spray concentration: 50–200 mg/L. For soil application, dilute to 10–50 mg/kg. Excessive use (>500 mg/L) may cause leaf margin scorching and inhibit growth.
(2) Application Timing
Nutrient Growth Stage: Promotes root development and tillering (e.g., wheat tillering stage, rice regreening stage).Reproductive Growth Stage: Enhances fruit set (e.g., tomato flowering stage, apple peak flowering stage).
Pre-Adverse Conditions: Strengthens resistance (e.g., 7 days before cold snap, early drought stage).
3) Blending Recommendations
Blending with 0.1% urea increases absorption efficiency by 30%.
Combining with alginate (0.05%) enhances stress resistance by 25%.
Avoid mixing with alkaline pesticides to prevent structural damage and loss of efficacy.
FAQ
Its synthesis: Tropic acid forms benzoic acid on oxidation with hot KMnO4. Tropic acid also reacts with HBr to form C9H9O2Br, C9H9O2Br reacts with alcoholic KOH to giveit, C9H8O2. On catalytic hydrogenation, this forms hydratropicacid, C9H10O2.
Mainly used in organic synthesis and fragrance raw material preparation.
This acid contains carbon-carbon double bond and carboxyl group, which can undergo common reactions such as esterification, addition, polymerization and decarboxylation. It is sensitive to high temperature, strong light and humid environment, and is easy to oxidize or deteriorate if exposed to air for a long time. It should be stored in a sealed, dry, cool and dark place, kept away from strong oxidants and heat sources, and avoid prolonged exposure to light to maintain its chemical purity and structural stability.
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