Cinnamic aldehyde
Cinnamaldehyde is an aldehyde organic compound, a yellow viscous liquid, which exists in large quantities in plants such as cinnamon. The naturally occurring cinnamaldehydes in nature are all trans-structures, and the molecule is a phenyl group attached to acrolein , so it can be considered as an acrolein derivative. The color of cinnamaldehyde is produced by the π→π* transition, and the existence of the conjugated structure makes the absorption spectrum of cinnamaldehyde enter the visible light band.
Preparation
Add 60 mL of 25% sulfuric acid and 13 g Ce(NO3)3.2H2O to the anode cell, and magnetically stir to dissolve the cerous salt. Add an appropriate amount of 25% sulfuric acid to the cathode chamber, turn on the DC power supply for electrolysis, control the relative density of the current to be 0.2A/20cm2, and electrolyze for 8.2h. Transfer the anolyte into a 250mL three-necked flask, add 1.349 cinnamyl alcohol, and stir the reaction at 5-10°C. When the bright yellow color of the solution subsides, it is the end point of the reaction. The reaction solution was extracted with ether (15 mL×3 times), the extracted reaction solution was used to regenerate Ce4+, the ether extract was dried with anhydrous sodium sulfate, filtered, and the ether was evaporated. Chromatographic analysis showed that the yield of cinnamaldehyde was 90%.
Application
Cinnamaldehyde is a synthetic fragrance for food specified in GB2760-2014, which can be used to prepare meat, condiments, oral care products, chewing gum, and candy flavors.
Physical and chemical indicators
Density: 1.046-1.052
Melting point (°C): -7.5°C.
Refractive index (20℃): 1.619-1.623
Specific gravity (25/25℃): 1.046-1.050
Acid value: ≤1.0%
Boiling point (℃): 253 (normal pressure).
Cinnamaldehyde molecular stereo model
Cinnamaldehyde molecular stereo model
Appearance: Colorless or pale yellow liquid.
Aroma: Strong aroma of cinnamon oil and cinnamon oil, mild spicy aroma, should not have spicy taste, strong and persistent aroma. Cinnamaldehyde has a stronger aroma than cinnamyl alcohol .
Solubility: insoluble in water and glycerol , easily soluble in alcohol, ether and petroleum ether . Can be volatile with water vapor.
Stability: unstable in strong acid or strong alkaline medium , easy to cause discoloration, easy to oxidize in the air.
Storage and transportation conditions
The warehouse is low temperature, ventilated and dry; fireproof; stored separately from oxidants and food raw materials.
Use
one. Application of cinnamaldehyde in medicine
1. Sterilization, disinfection and antisepsis, especially for fungi. For Escherichia coli , Bacillus subtilis and Staphylococcus aureus, Staphylococcus albus , Shigella Shigella, Typhoid and A. paratyphi, Pneumococcus , Aerobacter , Proteus , Bacillus anthracis , Salmonella Enteritidis , Vibrio cholera , etc. inhibition. And it has a significant bactericidal effect on Gram-positive bacteria , and can be used to treat a variety of diseases caused by bacterial infection. The minimum inhibitory concentration (MIC) is 0.02-0.07ul/ml, and for deep pathogenic fungi, the MIC is 0.1-0.3ul/ml. Japanese medical experts have found that cinnamaldehyde has a significant effect on fungi. The antifungal effect of cinnamaldehyde on 22 kinds of opportunistic fungi shows that cinnamaldehyde is an active antifungal substance, mainly by destroying the fungal cell wall and allowing drugs to penetrate In fungal cells, destroy organelles and play a bactericidal effect.
2. Anti-ulcer , strengthen stomach and intestinal movement. Its mechanism of action is due to the inhibition of ulcer active factors (gastric juice and pepsin) and the enhancement of defense factors (gastric mucosal blood flow rate), as well as inhibition of gastric mucosal potential reduction and mucosal protection. In addition, cinnamaldehyde can reduce pancreatic enzyme activity. Cinnamaldehyde is an aromatic stomach carminative, which has a mild stimulating effect on the stomach and intestines, can promote the secretion of saliva and gastric juice, enhance digestive function, relieve gastrointestinal smooth muscle spasm , and relieve intestinal spasm pain. For the treatment of stomach pain, flatulence and colic, it has significant stomach and carminative effects.
3. Lipolysis. Cinnamaldehyde can inhibit the release of adrenaline and ACTH to fatty acids, and promote the fat synthesis of glucose. Cinnamic acid also has such effects, but the effect of cinnamaldehyde is much greater than that of cinnamic acid. Therefore, it can be used in blood sugar control drugs to enhance the performance of insulin to replace glucose and prevent and treat diabetes.
4. Antiviral effect. For influenza virus, the tumor suppressor effect caused by SV10 virus is strong.
5. Anticancer effect. It can inhibit the occurrence of tumors, and has anti-mutagenic and anti-radiation effects.
6. Dilate blood vessels and lower blood pressure. It has antihypertensive effect on adrenal cortical hypertension.
7. Aphrodisiac effect. A study by the Chicago Center for Therapeutic Research shows that cinnamaldehyde has a certain effect on male aphrodisiac.
8. Commonly used in external medicine and synthetic medicine. It can be used in massage liquids and beauty products to disperse congestion, promote blood circulation, warm the skin, and tighten skin tissue. External use in massage can make limbs and body comfortable and improve water retention. It is effective in softening and clearing skin scars and fibroids. It is also used in external medicines such as safflower oil , cooling oil , and active collateral oil . It mainly activates the muscles and bones, disperses congestion, and has the functions of sedation, analgesia, antipyretic , anticonvulsant , and regulation of the central nervous system . Platelet count. It also has a strong fungicidal effect and has a suppressive effect on skin fungi. In a word, cinnamaldehyde can not only be used as an API by itself, added to various external medicines and finished medicines, but also can be further processed and synthesized into many powerful medicines.
two. Application of cinnamaldehyde in chemical industry
2. In industry, it can also be used as color developer and experimental reagent.
3. Insecticides, mosquito repellents, refrigerator deodorants, preservatives, etc. It has a strong killing effect on Aedes mosquito larvae that spread yellow fever, and it will become a new type of insecticide. Cinnamaldehyde is not only safe and environmentally friendly, but also has a fragrant smell. It contains an antimicrobial agent of cinnamaldehyde that repels insects. It can be directly used in drainage pipes ( sewers ) or special flavors for automobiles, air fresheners, oxygen generators, refrigerator deodorants, preservatives, etc.
4. Cinnamaldehyde can also be used as bactericidal algaecide and acidifying corrosion inhibitor in oil exploitation, instead of traditional antiseptic bactericides such as glutaraldehyde, which can significantly increase oil production, improve oil quality and reduce production costs. It opens up an unprecedented broad space for the application of cinnamaldehyde. Significant progress has been made in the application of cinnamaldehyde in Hebei Oilfield and Shengli Oilfield, and the application test in Daqing Oilfield is also underway.
6. Cinnamaldehyde chewing gum is both sterilizing and deodorizing . According to reports, experts from the School of Dentistry of the University of Illinois at Chicago reported a new research result. Naturally flavored chewing gum containing plant extracts such as cinnamaldehyde can kill bacteria in the mouth. , and thus reduce the generation of bad breath. Cinnamaldehyde is a commonly used vegetable flavoring oil. In the experiment, 15 subjects chewed three kinds of chewing gum, cinnamon-flavored, other natural flavors and unflavored chewing gums, each for 20 minutes. Twenty minutes after the subjects stopped chewing, they were compared with their saliva before and after chewing the gum. Microbiological analysis found that the cinnamon-flavored gum reduced the concentration of anaerobic bacteria in saliva by 50 percent, and even the back of the tongue was cleared by 43 percent. These anaerobic bacteria break down spoilage proteins to produce volatile sulfides that lead to unpleasant bad breath, while unflavored chewing gum does little to reduce oral bacteria. Studies have shown that chewing gums containing cinnamaldehyde and other active plant extracts can be used as functional health foods, and they can have a positive impact on oral hygiene in the short term. And cinnamaldehyde chewing gum is not only useful for masking bad breath, it actually removes the bacteria that cause bad breath. The latest bird repellent colloids take active evacuation methods in response to field demand, and the products are constantly innovating. The use of natural spice---cinnamaldehyde as a bird repellent colloid came into being. The bird repellent active ingredient has high content of cinnamaldehyde and has a long aging time. The high-concentration product is used in airport fairways. The biological preparation bird repellent colloid with cinnamaldehyde as the main raw material can slowly and persistently release a gas that affects the central nervous system of birds. It not only effectively drives away birds, but also does not harm them. It is a kind of green and environmentally friendly bird repellent product, which solves the world-class problems of human beings.
three. Application in flavors and fragrances
Cinnamaldehyde, as a hydroxy acid aroma - containing compound, has a good aroma retention effect. It is used as a fragrance raw material in fragrance blending to make the aroma of the main spice more fragrant. Because its boiling point is higher than that of other organic compounds with similar molecular structures, it is often used as a fixative. It is often used in soap essences to prepare essences such as gardenia, frangipani, lily of the valley and rose, and can be used in apple, cherry and fruit essences in food spices.
The amount of addition can be referred to as follows:
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refreshing drink
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10ppm
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candy
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700ppm
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ice cream
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ice cream
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8ppm
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200ppm
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chewing gum
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5000ppm
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meat
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60ppm
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condiment
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20ppm
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|
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Because cinnamaldehyde can not only modulate the aroma of various flavors, but also play the dual effect of sterilization and deodorization on the oral cavity. Commonly used in oral care products such as toothpaste, chewing gum and breath freshener.
Four. Application of cinnamaldehyde in food industry
It is commonly used in edible spice, preservation, antiseptic and mildew-proof agent (paper), and is also a good seasoning (material) oil to improve the taste and flavor. Such as: instant noodles, chewing gum, betel nut and other foods and baked goods such as bread, cakes and pastries.
Now the United States and Japan have researched and developed the application of cinnamaldehyde in food additives , mainly using its sterilization, disinfection and antiseptic functions. As a food antifungal agent, cinnamaldehyde is non-toxic or low-toxic to the human body, and has a strong inhibitory effect on the reproduction of microorganisms. Soluble in alcohol , ether , chloroform , grease, etc. It has bacteriostatic effect. When the concentration is 2.5×10-4, it has strong bacteriostatic effect on Aspergillus flavus , Aspergillus niger, Penicillium citri, Fusarium moniliformes, Alternaria alternaria, Geotrichum candidum and yeast .
Cinnamaldehyde has a very good anti-fungal effect. Inhibit mold growth, strong antibacterial effect. Can effectively kill bacteria, Escherichia coli. Cinnamaldehyde is an antifungal active substance. Foreign researchers have studied the antifungal effect of cinnamaldehyde on 22 opportunistic pathogenic fungi. The results showed that cinnamaldehyde had antibacterial effect on all tested bacteria. In the research on the anti-Aspergillus flavus effect and ultrastructure of cinnamaldehyde, it was found that cinnamaldehyde has obvious anti-Aspergillus flavus effect.
5. Application of cinnamaldehyde in feed
Cinnamaldehyde itself is a kind of spice. It has the functions of promoting growth, improving feed efficiency and controlling bacterial diarrhea of poultry and livestock, and can increase the aroma of feed, induce animals to eat, and prevent mildew of feed for a long time. Adding cinnamaldehyde No need to add other preservatives afterwards. Experts further study found that cinnamaldehyde also has the following properties.
1. In terms of promoting growth:
Cinnamaldehyde not only has good effect in pigs, but also can be used in chicken, duck and cattle feed, which is of great help in shortening the time to market. What's more worth mentioning is that even at high doses (25/50/100/200 ppm), it will not harm the intestinal villi.
2. Improve feed efficiency:
Different from general growth promoters, cinnamaldehyde can indeed increase the nitrogen retention in the animal body (about 7%) and nitrogen is the main component of synthesizing animal muscle cells, so it can improve carcass quality. positive impact.
3. The test shows that cinnamaldehyde has the function of killing hemolytic Escherichia coli that causes diarrhea in pigs, but has no effect on the harmless non-hemolytic Escherichia coli in the intestine. It is safe and has no concerns about reproductive obstacles. It can also be safely used in feed.
4. No residual problem:
Although cinnamaldehyde is absorbed after 24 hours, 90% is excreted in urine and 5% is excreted in feces, and the remaining 5% is decomposed into nutrients after being absorbed for 24 hours. There are no residues that are harmful to the human body.
In addition, in pig farms and chicken farms that use cinnamaldehyde for a long time, the soil mixed with manure has been tested and found that 90-99% of cinnamaldehyde has been decomposed and disappeared after 24 hours after cinnamaldehyde is excreted into the soil.
5. General usage and dosage:
Pigs: 5-20 kg 100 ppm
20-60 kg 50 100 ppm
60-100 kg 50 ppm
Chicken: Chick Feed 40 ppm
Big Chicken Feed 20 ppm
Duck: 50 ppm
6. Application in health care and antiseptic
People in the industry generally believe that the world of Jingjiu is supported by cinnamaldehyde! Jingjiu is based on Xiaoqu Baijiu and is made of selected authentic medicinal materials. It has the health care functions of anti-fatigue and immune regulation. Among the several medicinal materials with aphrodisiac effects in Jingjiu, cinnamaldehyde is the main medicinal material. It has a good effect of dilating blood vessels, promoting blood circulation, and exciting. Compared with the western aphrodisiac ingredient sildenafil (commonly known as "Viagra"), cinnamaldehyde has a milder effect and has no toxic side effects on the human body. For China's plant-based "Viagra". The success of Jingjiu also lies in the fact that cinnamaldehyde can make people develop harmless spiritual dependence. Once it is consumed, it will not be abandoned for life, so it has a large number of loyal markets. The re-emergence strategy of Dongjiu, a famous Chinese wine that has declined, will also choose the successful route of Jingjiu, using cinnamaldehyde as the main medicinal material.
The antiseptic effect of cinnamaldehyde has also been strongly confirmed in betel nut processed products. In the streets and alleys of Xiangtan, Hunan Province, betel nut can be sold in the open without any packaging, and it will not deteriorate for a long time. The important reason is that betel nut has been soaked in cinnamaldehyde solution. As a preservative, cinnamaldehyde can not only greatly extend the shelf life, but also degrade into the nutrients needed by the human body in the intestinal tract after entering the human body, which is harmless and beneficial to the human body. Cinnamaldehyde can not only enhance the medicinal effect of betel nut, make betel nut more pure, its unique cinnamon fragrance, but also enhance the taste of betel nut.
