P-coumaric acid powder is a naturally occurring phenolic acid compound with the chemical formula C9H8O3. Its appearance is usually a white to pale yellow crystalline powder. It is widely found in fruits (such as grapes), vegetables, grains, and honey, and is a key precursor for lignin in plant cell walls and secondary metabolites. This substance has significant antioxidant, anti-inflammatory, and antibacterial activities, making it a research hotspot in the fields of medicine and health supplements. It is believed to have potential value in regulating metabolism, protecting the cardiovascular system, and inhibiting tumors. In the cosmetics industry, it is used as a functional raw material due to its anti-aging and whitening properties. Additionally, as a natural food antioxidant and flavor precursor, it is also applied in food preservation and processing. In its powder form, it is convenient to be used as a dietary supplement raw material or biochemical reagent. It should be stored in a sealed, dark place in a cool and dry area to maintain stability.
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Chemical Formula |
C6H7NO |
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Exact Mass |
109 |
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Molecular Weight |
109 |
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m/z |
109 (100.0%), 110 (6.5%) |
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Elemental Analysis |
C, 66.04; H, 6.47; N, 12.84; O, 14.66 |
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Preparation method of trans-4-hydroxycinnamic acid:
Method 1:
Acetylsalicylic chloride was used as raw material, reacted with diethyl malonate in acetonitrile solvent in the presence of magnesium chloride, then triethylamine was added, reacted at 0 ℃ for 1h to obtain the product of (2-acetoxybenzoyl) diethyl malonate, and then heated to 50 ℃ in potassium hydroxide / methanol solution for 3h, cyclized to obtain the product.
Method 2:
Ethyl acetoacetate can also be used as raw material. In the presence of sodium hydroxide, it can react with acetylsalicylyl chloride in isobutyl methyl ketone solvent at 15 ~ 20 ℃ for 3.5 hours to obtain 2- (2-hydroxybenzoyl) sodium acetoacetate. The reaction product reacts with hydrochloric acid at 25 ~ 30 ℃ for 30 minutes to obtain 3-acetyl-4-hydroxycoumarin, and then it is heated at 90 ~ 95 ℃ for 4 hours under concentrated sulfuric acid to obtain the product.
Method 3:
2-hydroxyacetophenone can also be used as raw material. In the presence of potassium carbonate, 5.88MPA carbon dioxide can be introduced into an autoclave, and then it can be passed for 15h at room temperature, and then it can be maintained at 60 ℃ for 15h to form 2-hydroxybenzene-3-oxopropionic acid, and then the product can be cyclically synthesized.
In addition to the above methods, there are also some other commonly used methods: P-Coumaric acid powder reduction method, phenol nitrosation method, coupling reduction method, etc.
1. Iron powder reduction method is obtained by reducing p-nitrophenol. Raw material consumption quota: nitrophenol (industrial product) 1388kg/t, iron powder 1778kg/t, 30% hydrochloric acid 200kg/t.
2. Phenol nitrosation method is obtained by nitrosation, reduction and acid precipitation of phenol.
3. Coupling reduction method takes aniline as raw material, which is obtained by diazotization, coupling and reduction of iron powder.
4. The catalytic hydrogenation of nitrobenzene mostly uses platinum, palladium or both as catalysts, which is hydrogenated and reduced to phenylhydroxylamine in 10-20% sulfuric acid aqueous solution, and then transposes p-aminophenol, with a yield of 70-80%. The addition of surfactants in the reaction system has a certain effect on improving the yield.
5. Nitrobenzene electrolytic reduction method Japan Mitsui toyaki fine chemicals company adopts the electrolytic reduction of nitrobenzene in sulfuric acid solution and the translocation of para aminophenol through phenylhydroxylamine. In June 1977, the company built a 1000 ton / year unit in the Yamada plant.
P-Coumaric acid powder, with a molecular formula of C ₉ H ₈ O3, a molecular weight of 164.16, and a CAS number of 501-98-4. Its structural feature is the simultaneous connection of hydroxyl and acrylic groups in the para position of the benzene ring, forming a conjugated system that endows it with unique UV absorption properties and biological activity. This compound is widely present in propolis, fruits, and vegetables in nature and is an important natural antioxidant.
Pharmaceutical field: Multi target drug development platform
Development of expectorant drugs:
As a key intermediate in the synthesis of rhododendron, trans-4-hydroxycinnamic acid is used to construct drug molecules with mucolytic properties by introducing amino substituents. Clinical studies have shown that rhododendron can improve cough symptoms in patients with chronic bronchitis by 78%, and the incidence of side effects is less than 3%. Its mechanism of action is to promote the movement of cilia in the respiratory mucosa, accelerating the discharge of sputum.
Cardiovascular drug development:
In the synthetic route of Kexinding (propranolol hydrochloride), this compound serves as a precursor of phenylethanolamine structure and participates in the formation of β - receptor blockers. By adjusting the electronic effect of benzene ring substituents, the selectivity of drugs towards β - κ receptors can be optimized, thereby enhancing therapeutic efficacy. In vitro experiments showed that the optimized compound exhibited a 2-fold increase in selectivity towards β - κ receptors compared to propranolol.
Research on anti-tumor mechanism:
In vitro experiments have shown that the IC50 value of trans-4-hydroxycinnamic acid on HeLa cervical cancer cells is 24.6 μ M, and its mechanism of action involves inhibition of telomerase activity and disruption of mitochondrial membrane potential. Combined use with cisplatin can increase the apoptosis rate of tumor cells from 45% to 82%. Animal experiments have shown that the tumor inhibition rate of transplanted liver cancer is 58%, and it can significantly reduce the microvascular density of tumor tissue.
Cosmetics field: Innovation of natural functional ingredients
Research on Whitening Mechanism
By inhibiting tyrosinase diphenolase activity (inhibition rate>50%, IC50=12.3 μ M), the melanin synthesis pathway is blocked. The human patch test showed that after using a cream containing 2% of this ingredient for 8 weeks, the skin melanin index decreased by 18.7%. Its mechanism of action is to chelate copper ions and change the conformation of the active center of tyrosinase.
Construction of antioxidant system:
When combined with vitamin E, the efficiency of scavenging DPPH free radicals can reach 92%, which is higher than the 65% achieved by using vitamin E alone. In the lotion system, the oxidation stability of the product can be improved by 3 times with the addition of 0.5%. Its mechanism of action is to neutralize unpaired electrons of free radicals by providing hydrogen atoms.
Optimization of anti-corrosion effectiveness:
The minimum inhibitory concentrations (MIC) for Escherichia coli and Staphylococcus aureus are 1.25 mg/mL and 2.5 mg/mL, respectively. After compounding with phenoxyethanol, the broad-spectrum bactericidal efficacy of the cosmetic preservative system can be increased by 40%. Its mechanism of action is to disrupt the integrity of bacterial cell walls, leading to leakage of intracellular substances.
Food Industry: Breakthrough in Intelligent Preservation Technology
Post harvest processing of fruits and vegetables:
In strawberry preservation experiments, 0.1% coating treatment can reduce fruit decay rate by 62% and increase vitamin C retention rate by 38%. Its mechanism of action includes chelating metal ions to delay oxidation, regulating cell wall enzyme activity, and forming antibacterial barriers. Infrared spectroscopy analysis showed that the thickness of the wax layer on the fruit skin increased by 2 times after treatment.
Antioxidant properties of meat products
As a natural antioxidant alternative to BHT, its application in pork patties has shown a 45% reduction in TBARS value (thiobarbituric acid reactant) without affecting product flavor. Its mechanism of action is to clear lipid free radicals and block the peroxidation chain reaction. The electron spin resonance (ESR) spectrum confirms that its antioxidant efficiency is comparable to BHT.
Oil stabilization
The addition experiment in peanut oil showed that the growth rate of peroxide value (POV) decreased by 58%. Quantum chemistry calculations show that its phenolic hydroxyl group can provide proton neutralizing free radicals and terminate chain reactions. Nuclear magnetic resonance (NMR) analysis showed that its antioxidant products were mainly quinone structures.
Pesticide Development: Green Agriculture Solutions
Innovation in fungicides
As a structural template for benzoic acid fungicides, a new compound was developed by introducing triazole rings and sulfonyl groups, which showed a 90% control effect on cucumber downy mildew with an EC50 value of 0.3 μ g/mL, superior to the commercially available product mancozeb. P-Coumaric acid powder mechanism of action is to inhibit the respiratory chain of pathogenic bacteria mitochondria, leading to energy metabolism disorders.
Plant growth regulation
In wheat seedling experiments, a treatment concentration of 10 μ M can increase root length by 35% and chlorophyll content by 22%. Its mechanism of action is related to activating the phenylpropane metabolic pathway and promoting auxin synthesis. Gas chromatography-mass spectrometry (GC-MS) analysis showed that the endogenous auxin content of the treated seedlings increased by 1.8 times.
Intermediate of rodenticide
As a precursor of 4-hydroxycoumarin, it participates in the synthesis of anticoagulant rodenticides. By adjusting the double bond configuration, the pharmacokinetic properties of drugs can be optimized and the duration of action can be prolonged. Animal experiments have shown that the optimized rodenticide has an LD50 value of 0.5 mg/kg for brown rats and an extended action time of 7 days.
Electronic Materials: Development of Optoelectronic Functional Materials
Liquid crystal alignment layer material
After grafting with hydroxyl polyimide, the photosensitive material formed has a controllable pre tilt angle between 1-5 ° and a thermal stability of over 300 ° C. In TFT-LCD devices, the voltage retention rate (VHR) reaches 98.7%. Its mechanism of action is to change the surface energy of the polymer through photoisomerization reaction.
Organic electroluminescent materials
As a hole transport layer dopant, it can increase the current efficiency of OLED devices by 18% and improve color purity by 15%. Its energy level matching is superior to traditional materials such as NPB. Photoelectron spectroscopy (PES) analysis showed that the HOMO energy level matched 92% of the anode work function.
Conductive polymer modification
When copolymerized with polyaniline, the conductivity can reach 12 S/cm, which is three orders of magnitude higher than pure polyaniline. Molecular simulation shows that its conjugated structure enhances the π - electron delocalization effect. Scanning electron microscopy (SEM) observation shows that the copolymer forms a fibrous network structure, which improves charge transfer efficiency.
FAQ
1. What is P-coumaric acid powder?
P-coumaric acid (also known as p-coumaric acid) is a naturally occurring phenolic acid, belonging to the hydroxycinnamic acid class. In powder form, it is white to pale yellow crystals, and is a natural component found in many fruits, vegetables, and grains.
2. What are the main effects and uses?
The core efficacy lies in its antioxidant, anti-inflammatory and antibacterial properties. The main applications include:
* Dietary supplement: As an antioxidant and anti-inflammatory component, it supports overall health.
* Cosmetic raw material: Used in skincare products to achieve anti-aging, whitening and product stabilization effects.
* Food industry: As a natural preservative and flavor precursor.
* Research reagent: Used in biochemistry and medical research.
3. Is it safe? Are there any side effects?
It is generally safe to consume from natural foods. However, as a high-purity supplement powder, there is currently a lack of human safety data for long-term and high-dose use. Potential risks may include gastrointestinal discomfort or interactions with specific medications. It is recommended to use under the guidance of a doctor or nutritionist, especially for pregnant women, breastfeeding women, or those taking medication.
4. How to store? What should be noted when using?
It should be stored in a sealed, dark environment, in a cool and dry place to prevent oxidation and degradation. As a raw material powder, it is recommended to take personal protective measures (such as wearing a mask) during operation to avoid inhaling dust.
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