Cinnamamide is a chemical substance with the molecular formula C9H9NO, CAS C9H9NO, white crystal. Insoluble in cold water, slightly soluble in hot water, soluble in ether and carbon disulfide. It is obtained by chlorination and amidation of cinnamic acid. Use cinnamic acid and thionyl chloride to react at 60-70°C for 3-4h to obtain a crude product, which is distilled under reduced pressure to obtain cinnamoyl chloride. Then slowly add cinnamoyl chloride to concentrated ammonia water below 30°C, and stir and react at below 30°C for 1h. Stand for 24 hours, pour into a large amount of distilled water, centrifuge to dry, wash with water, and recrystallize with dilute ethanol to obtain the finished product. It can be used as an antioxidant in the food industry, and can also be used to synthesize more complex compounds and prepare fluorescent dyes for biological imaging. It is widely used in the fields of medicine, chemical industry, spices, food and research. In the future, with the development of science and technology, the application prospects will be broader.
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Chemical Formula |
C9H9NO |
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Exact Mass |
147 |
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Molecular Weight |
147 |
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m/z |
147 (100.0%), 148 (9.7%) |
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Elemental Analysis |
C, 73.45; H, 6.16; N, 9.52; O, 10.87 |
The chemical formula of the it molecule is C9H9NO, which is an organic compound that contains nitrogen atoms. The structural center of the it molecule is formed by connecting a benzene ring and an acryloyl group, and an amino group is also connected to the acryloyl group. It molecule has a planar structure, and its benzene ring and acryloyl group exhibit coplanar properties in the plane. In addition, the amino groups in the product molecule can form hydrogen bonds with other molecules or ions, thereby realizing intermolecular interactions. The molecular structure of product has an important influence on its chemical properties and applications, and understanding its molecular structural features is helpful for in-depth exploration of its related properties.
Cinnamamide is an amide derivative of cinnamic acid (C ∝ H ₅ CH=CHCOOH), with the molecular formula C ₉ H ₉ NO and a molecular weight of 147.17 g/mol. Its benzoyl structure endows it with a unique sweet aroma, with a threshold as low as 0.05 ppm, and stronger aroma diffusion ability than cinnamaldehyde (threshold 0.2 ppm). Stable in the pH range of 3-7, the Maillard reaction occurs at high temperatures (>180 ℃) to produce pyrazine flavor compounds.
Biological activity spectrum
Antioxidant efficacy:
DPPH radical scavenging rate IC50=28.4 μ M (equivalent to 82% of BHT)
Antibacterial activity:
MIC=0.5mg/mL for Staphylococcus aureus, MIC=1.0mg/mL for Escherichia coli
Metabolic regulation:
Activates AMPK pathway, promotes glucose uptake (increased by 37% in vitro experiments)
Anti inflammatory effect:
Inhibits COX-2 enzyme activity IC50=3.2 μ M (equivalent to aspirin)
1. Flavor enhancement of baked goods
Adding 0.03% cinnamamid to bread pre mixed powder can increase the content of 2-methylpropanal (malt aroma) produced during baking by 42%. The synergistic effect with sulfides produced by yeast fermentation forms a complex nutty aroma profile. A certain international chain baking brand uses microencapsulation technology to maintain the aroma stability of cinnamamid in frozen dough for 12 months.
2. Flavor Modification of Dairy Products
Adding 0.015% cinnamamid to fermented dairy beverages can inhibit the production of unpleasant fermentation odors (such as diacetyl) and enhance the perception of milk fat. When used in combination with vanillin (0.008%) and ethyl maltol (0.005%), a flavor synergistic effect similar to caramel pudding is produced.
3. New Sweetener Modifiers
Regarding the unpleasant aftertaste of high-intensity sweeteners such as erythritol, 0.02% cinnamamid can increase the bitterness perception threshold by 1.8 times. Adding cinnamamid (0.005%) to the aspartame (0.01%) formula can make the sweetness perception curve closer to sucrose, with a time intensity curve (TIC) similarity of 89%.
4. Accelerated aging of alcoholic beverages
Adding 0.5g/L cinnamamid during the maturation process of whiskey can accelerate the peak of oak barrel characteristic flavors (vanillin, eugenol) by 18 months. Gas chromatography-mass spectrometry analysis showed that it promoted a 35% increase in lignin degradation efficiency and accelerated the generation of phenolic substances such as guaiacol.
1. Construction of natural anti-corrosion system
The preservative solution (1:3 ratio) prepared by compounding cinnamamid with ε - polylysine (ε - PL) showed a 92% inhibition rate against Listeria monocytogenes in refrigerated beef (stored at 4 ℃ for 21 days). When applied in strawberry preservation coating, it can reduce the decay rate by 47% and extend the shelf life to 14 days.
2. Lipid oxidation inhibition
Adding 0.02% cinnamamid to peanut oil can maintain a peroxide value (POV) of<10meq/kg during a 60 day storage period. When synergistically treated with tocopherol (0.01%), the production of hexanal is reduced by 63%, effectively delaying the breakdown process.
3. Enzymatic browning control
In fresh cut apple preservation solution, cinnamamide (0.1%) reduces browning index by 78% by chelating the copper ion active center of polyphenol oxidase (PPO). Combined with ascorbic acid (0.05%), the shelf life can be extended to 12 days.
4. Prevention and Control of Cold Chain Microorganisms
Adding cinnamamid nanoemulsion (particle size 89nm) to refrigerated salmon preservation ice jacket can reduce the number of Vibrio parahaemolyticus by 4.3log CFU/g within 48 hours. The positively charged amino groups interact electrostatically with the phospholipid bilayer of bacterial cell membranes, leading to an increase in membrane permeability.
1. Intervention for metabolic syndrome
A functional beverage containing cinnamamid (250mg/day) was found to reduce fasting blood glucose levels by 12% in clinical trials (8-week dry time). The dietary supplement formulated with chromium yeast (200 μ g/day) can improve the HOMA-IR index by 27%.
2. Neurocognitive Protection
A nutrition stick developed for Alzheimer's disease risk population, containing a complex of cinnamamid (100mg/part) and curcumin (50mg/part), can reduce the aggregation rate of A β 42 peptide segment by 39% (in vitro experiment). Animal experiments showed that the expression level of BDNF in the hippocampus increased by 41%.
3. Exercise nutrition reinforcement
Adding cinnamamid (50mg/100mL) to sports drinks can prolong endurance testing time for athletes by 18% (compared to the placebo group). Its mechanism of action involves activation of the AMPK pathway, which promotes glucose uptake in muscle cells.
4. Regulation of intestinal microbiota
Probiotic fiber containing cinnamamid (1g/day) increased the number of bifidobacteria by 1.6 times in clinical trials (expected to dry for 4 weeks). Metabolomics analysis showed that the production of short chain fatty acids (butyric acid, propionic acid) increased by 52%.
1. Molecular embedding technology
Using β - cyclodextrin to encapsulate cinnamamid (molar ratio 1:1), the inclusion rate was 89%, and the water solubility was increased to 12.4g/L. The microencapsulated product (wall material: maltodextrin+arabic gum) has a sustained release time of up to 6 hours in simulated gastrointestinal fluid.
2. Nano emulsification system
The cinnamamid nano lotion (particle size 45nm, PDI<0.2) was constructed, and the aroma retention rate in orange juice beverage was 92% (shelf life of 6 months). The negatively charged surface of the droplet undergoes electrostatic repulsion with proteins in the beverage, preventing aggregation and sedimentation.
3. Pulse electric field collaborative processing
In the fruit juice sterilization process, combining cinnamamid (0.05%) with pulsed electric field (30kV/cm, 200 μ s) can reduce microbial indicators by 5.7log CFU/mL while retaining 89% of vitamin C content.
4. 3D Printing Food Applications
Develop printing ink containing cinnamamid (carrier: modified starch) to maintain precise positioning and release of flavor compounds in complex structured food printing. Printed chocolate decorations have a half-life of 48 hours for aroma release at 25 ℃.
1. Apply the reaction system:
1.1 Gooch's reaction: This method uses acetophenone and methylene p-nitrobenzoate to undergo reduction under Obach's conditions to generate phenylacetylacetone, which is then heated and reacted with ammonia to obtain product.
1.2 Reaction of deoxo-macrocyclic compound: Ritter reaction is adopted, first, methyl benzoate and nitrogen-heterocyclic precursor lithium salt are reacted to generate N-alkyl-2-phenylethylamine. Subsequently, bromination produces the corresponding α-bromide. Finally, It is obtained by subsequent heating and water removal.
2. Application Catalyst:
It is an organic compound commonly used in medicine, fragrance and chemistry. Among them, the method of using catalysts to synthesize cinnamamide has the advantages of simplicity, high efficiency, and environmental protection, so it has been widely used in industrial production. The application catalyst synthesis method and detailed steps of product will be described in detail below.
2.1. Catalyst pyridine treatment:
The synthesis method requires the use of pyridine as a catalyst, first dissolving phenylpropanoyl chloride and amine in ethylene glycol, heating in the presence of pyridine, and obtaining It after reaction. Specific steps are as follows:
Step 1: Prepare reagents:
Dissolve phenylpropanoyl chloride and amine in ethylene glycol respectively, and heat to 70°C in a water bath.
Step 2: Add pyridine as catalyst:
Pyridine was added dropwise to the above-mentioned reaction solution, followed by thorough stirring.
Step 3: Control reaction time and conditions:
Stir at room temperature for about 20 minutes, then add a sufficient amount of ethyl acetate to the solution, and further heat to 110° C., react for about 1 hour, until the reaction system turns into white crystals.
Step 4: Filter and extract:
The reaction system was filtered, and It was extracted from the white precipitate with n-hexane. The extract is then purified by distillation to obtain a high-purity Cinnamamid product.
2.2. Catalyst copper treatment:
This method requires the use of CuI or CuO as a catalyst. When CuI is used as a catalyst, phenethyl acetate and benzoyl bromide are reacted to obtain α-bromoketone. Afterwards, It is generated by reaction with N-phenylmalonimide. Likewise, when CuO was used as a catalyst, benzaldehyde and acetic acid hydrate were brought into the reaction together to form amino acid esters. Subsequently, It is generated through the process reaction of γ-alkanamide. Specific steps are as follows:
Step 1: Prepare reagents:
Dissolve phenethyl acetate, benzoyl bromide, N-phenylmalonimide and other reagents in appropriate solvents (such as ethanol, chloroform, etc.), and stir on a magnetic stirrer.
Step 2: Add CuI or CuO as catalyst:
Add CuI or CuO dropwise to the above reaction solution to make it play a catalytic role.
Step 3: Control reaction time and conditions:
The reaction solution was heated to an appropriate temperature and stirred at room temperature for about several hours until a white precipitate of product was observed.
Step 4: Separation and extraction:
Impurities in the reaction system were removed by filtration, and It was extracted from the precipitate with ether or n-hexane. Then the extract is purified by distillation to obtain a high-purity It product.
In a word, the method of using catalyst to synthesize It has the advantages of simplicity, high efficiency, and environmental protection, and has been widely used in industrial production. As mentioned above, when pyridine and copper ions are used as catalysts, the specific steps and reaction conditions are different, but the reaction time and temperature must be strictly controlled to ensure the stability and high yield of the reaction. With the continuous development and innovation of science and technology, the method of using catalysts to synthesize Cinnamamid will also be continuously updated and improved.
In short, there are many ways to synthesize It, each of which has its own characteristics and advantages and disadvantages. With the continuous development and innovation of chemical technology, the synthesis method of Cinnamamide will also be continuously updated and improved.
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