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Trans-cinnamaldehyde, as the core aromatic component of cinnamon essential oil, has an α,β-unsaturated aldehyde functional group in its chemical structure, which is like a precise molecular key. It can penetrate the microbial cell membrane and irreversibly bind to the sulfhydryl groups on the membrane proteins, causing intracellular electrolyte imbalance and energy metabolism collapse. This unique mechanism makes it highly inhibitory against foodborne pathogenic bacteria such as Salmonella and Listeria, and even at sub-inhibitory concentrations, it can effectively interfere with the bacterial quorum sensing system and prevent the formation of biofilms. In the agricultural field, it activates the jasmonic acid signaling pathway related to plant defense, induces systemic resistance, and at the same time, its volatile characteristics make it an ideal post-harvest fumigation preservative. More strikingly, trans-cinnamaldehyde can specifically inhibit the activation of the NF-κB signaling pathway in tumor cells and induce apoptosis of cancer cells through the mitochondrial pathway. In the research on chemical prevention of colorectal cancer, it shows potential. This multi-dimensional biological activity from a flavoring spice to antibacterial preservation, from triggering plant immunity to tumor intervention, perfectly illustrates the infinite possibilities of natural small molecules in cross-application.
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Chemical Formula |
C9H8O |
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Exact Mass |
132 |
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Molecular Weight |
132 |
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m/z |
132 (100.0%), 133 (9.7%) |
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Elemental Analysis |
C, 81.79; H, 6.10; O, 12.11 |
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Trans-Cinnamaldehyde, also known as cinnamaldehyde, cinnamaldehyde, β - cinnamaldehyde, or 3-phenyl-2-acrolein, is an aldehyde organic compound widely present in essential oils such as cinnamon oil, rose oil, and patchouli oil. Its chemical name is triphenylacrolein, and its molecular formula is C9H8O. At atmospheric pressure, the melting point of cinnamaldehyde is -8 ℃, while its boiling point reaches 253 ℃, usually in liquid form. It is worth noting that all natural cinnamaldehyde exhibits a trans structure. This compound emits a rich and long-lasting cinnamon oil aroma, which is not only loved for its unique flavor, but also widely used in various fields such as medicine and food industry due to its multiple effects of antibacterial, anti mold, vasodilation, and blood pressure reduction.
The application of cinnamaldehyde in medicine
1.Sterilization, disinfection, and anti-corrosion, especially with significant therapeutic effects on fungi. It has inhibitory effects on Escherichia coli, Bacillus subtilis, Staphylococcus aureus, Staphylococcus aureus, Shigella dysenteriae, Salmonella typhi and paratyphoid, Streptococcus pneumoniae, Pseudomonas aeruginosa, Proteus mirabilis, Bacillus anthracis, Salmonella enterica, Vibrio cholerae, etc. And it has a significant bactericidal effect on Gram positive bacteria, which can be used to treat various diseases caused by bacterial infections. The minimum inhibitory concentration (MIC) is 0.02-0.07ul/ml, and for deep-seated pathogenic fungi, the MIC is 0.1-0.3ul/ml. Japanese medical experts have found that cinnamaldehyde has significant therapeutic effects on fungi. Studies on the antifungal effects of cinnamaldehyde on 22 conditionally pathogenic fungi have shown that cinnamaldehyde is an active substance against fungi, mainly by destroying the fungal cell wall, allowing drugs to penetrate into fungal cells, and disrupting organelles to exert bactericidal effects.
2.Anti ulcer, strengthen gastric and intestinal motility. Its mechanism of action is due to the inhibition of ulcer activity factors (gastric juice and pepsin) and the strengthening of defense factors (gastric mucosal blood flow rate), as well as the inhibition of gastric mucosal potential reduction and the protective effect on the mucosa. In addition, cinnamaldehyde can reduce pancreatic enzyme activity. Cinnamaldehyde is an aromatic stomach promoting and wind expelling agent that has a mild stimulating effect on the gastrointestinal tract. It can promote saliva and gastric juice secretion, enhance digestive function, relieve smooth muscle spasms in the gastrointestinal tract, and alleviate spasmodic pain in the intestines. Used for treating stomach pain, gastrointestinal bloating and colic, it has significant effects on strengthening the stomach and dispelling wind.
3. Fat breakdown function. Cinnamaldehyde has the ability to inhibit the free release of fatty acids by adrenaline and ACTH, promote the fat synthesis of glucose, and cinnamic acid also has such effects, but cinnamaldehyde has a much greater effect than cinnamic acid. Therefore, it can be used in blood glucose control drugs to enhance the ability of insulin to replace glucose and prevent diabetes.
4. Antiviral effect. The tumor suppressive effect caused by influenza virus and SV10 virus is strong.
5. Anti cancer effect. It can inhibit the occurrence of tumors and has anti mutagenic and anti radiation effects.
6. Expand blood vessels and reduce blood pressure. It has a hypotensive effect on adrenal cortical hypertension.
7. The function of enhancing male potency. A study by the Chicago Treatment Research Center in the United States shows that cinnamaldehyde has a certain effect on male impotence.
8. Commonly used in topical and synthetic drugs. Applied in massage fluids and beauty products, it helps to disperse blood stasis, promote blood circulation, warm the skin, and tighten skin tissue. External use in massage can make the limbs and body feel comfortable, and improve water retention. Trans-Cinnamaldehyde has an effect on softening and removing scars and fibroids on the skin. It is also used in external medicines such as safflower oil, cooling oil, and activating collaterals oil. It mainly functions to activate collaterals and bones, disperse congestion, and has sedative, analgesic, antipyretic, anticonvulsant, and central nervous system regulating effects. It can also increase white blood cell and platelet counts. It also has a strong antifungal effect and a suppressive effect on skin fungi. In short, cinnamaldehyde can not only be used as a raw material and added to various external and finished drugs, but also further processed and synthesized into many powerful drugs.
Application of Cinnamaldehyde in Chemical Industry
1. Organic chemical synthesis. Used for synthesizing a series of products such as α - bromocinnamaldehyde, cinnamic acid, cinnamyl alcohol, cinnamonitrile, etc.
In industry, it can also be used as a color developer and experimental reagent.
3. Insecticides, mosquito repellents, refrigerator deodorizers, preservatives, etc. It has a strong killing effect on Aedes mosquitoes larvae that spread yellow fever and will become a new type of insecticide. Cinnamaldehyde is not only safe and environmentally friendly, but also has a fragrant odor. It is an antimicrobial agent containing cinnamaldehyde that can repel insects. It can be directly used for drainage pipes (sewers) or essence, air fresheners, oxygen generators, refrigerator deodorants, preservatives, etc.
4. Cinnamaldehyde can also be used as a bactericidal and algicidal agent, acidification inhibitor in petroleum extraction, replacing traditional anti-corrosion and bactericidal agents such as glutaraldehyde. It can significantly increase petroleum production, improve petroleum quality, and reduce extraction costs. This has opened up unprecedented opportunities for the application of cinnamaldehyde. Significant progress has been made in the application of cinnamaldehyde in Hebei Oilfield and Shengli Oilfield, and application trials in Daqing Oilfield are also underway.
5. Unlike sodium benzoate, the application of cinnamaldehyde is not affected by pH value. It has strong sterilization and disinfection functions for acidic or alkaline substances, and can also be widely used for anti-corrosion, mold prevention, and preservation. With the continuous extension of the application field of cinnamaldehyde, Dr. Zolads and others from Wheeling Jesuit University in the United States reported their new findings at the annual meeting of the Chemical Induction Federation; Cinnamaldehyde can enhance brain function and help improve memory. This research result has a very promising prospect and will bring new development and leaps to the cinnamon series products.
6. Cinnamaldehyde chewing gum can kill bacteria and reduce bad breath. According to reports, experts from the School of Dentistry at the University of Illinois at Chicago reported a new research result that natural flavored chewing gum containing plant extracts such as cinnamaldehyde can kill bacteria in the mouth and thus reduce the production of bad breath. Cinnamaldehyde is a commonly used vegetable seasoning oil.
In the experiment, 15 participants chewed three types of chewing gum, namely cinnamon flavored, other natural flavored, and non flavored chewing gum, each lasting for 20 minutes. 20 minutes after the subjects stopped chewing, a comparative test was conducted on their saliva before and after chewing gum. Microbial analysis found that cinnamon flavored chewing gum reduced the concentration of anaerobic bacteria in saliva by 50%, and even cleared anaerobic bacteria behind the tongue by 43%. These anaerobic bacteria decompose and decay proteins to produce volatile sulfides, leading to unpleasant bad breath, while chewing gum without any seasoning has little function in reducing oral bacteria.
Research has shown that chewing gum containing cinnamaldehyde and other active plant extracts can be used as functional health foods, which can have a positive impact on oral hygiene in the short term. Cinnamaldehyde gum can not only be used to mask bad breath, but it can truly eliminate the bacteria that cause bad breath.
The latest bird repellent colloid agent meets the demand of the field, adopts active evacuation methods, and constantly introduces new products. The use of natural spice cinnamaldehyde as a bird repellent colloid has emerged. The effective ingredient for bird repellent, cinnamaldehyde, has a high content and long shelf life. High concentration products are used in airport waterways. The biological preparation bird repellent colloid, mainly made of cinnamaldehyde, can slowly and persistently release a gas that affects the central nervous system of birds. Birds fly away immediately after hearing it and will not come back during their memory period. It is a green and environmentally friendly bird repellent product that effectively drives away birds without harming them, solving a world-class problem for humans.
Application in essence
Trans-Cinnamaldehyde, as a hydroxy acid containing aromatic compound, has a good fragrance holding effect and is used as a flavoring ingredient in fragrance adjustment, making the main fragrance more fragrant. Due to its higher boiling point than other organic compounds with similar molecular structures, it is commonly used as a fragrance fixative. It is commonly used in soap essence, and can be used to make gardenia, jasmine, lily of the valley, rose and other essence. It can be used in apple, cherry, and fruit essence in food spices. The addition amount can be referred to as follows: 10ppm for refreshing drinks, 700ppm for candies, 8ppm for ice cream, 200ppm for chewing gum, 5000ppm for meat, 60ppm for seasonings, and 20ppm for cinnamaldehyde. Cinnamaldehyde can not only mix various flavors of fragrances, but also has dual effects of sterilization and deodorization on the oral cavity. Commonly used in oral care products such as toothpaste, chewing gum, and breath fresheners.
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