+86-28-82633987
Product name: p-Coumaric acid ethyl ester
Synonym name:
Catalogue No.: SBP01659
Cas No.: 7362-39-2
Formula: C11H12O3
Mol Weight: 192.214
Botanical Source:
Physical Description: Powder
Type of Compound: Phenylpropanoids
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
The product could be supplied from milligrams to grams. Inquire for bulk scale.
We provide solution to improve the water-solubility of compounds, thereby facilitating the variety of activity tests and clinic uses.
For Reference Standard and R&D, Not for Human Use Directly.
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
46.5300
2.5930
2.5883
.5818
4.0022
29.3848
High
80.4680
1.7993
Yes
No
Yes
No
Yes
Yes
0.0
No
Yes
Yes
Yes
Ethyl (E)-p-hydroxycinnamate, CAS No.: 7362-39-2) is a naturally occurring phenolic compound belonging to coumaric acid and its ester derivatives. As a non-competitive reversible inhibitor of tyrosinase (TYR), it demonstrates significant pharmacological potential for ethyl coumarate in antioxidant, anti-melanin production, and related disease prevention and treatment. In recent years, with the deepening development of natural product pharmacology, ethyl coumarate has gradually become a research hotspot in drug development, cosmetics, and food preservation due to its unique enzyme inhibition mechanism and excellent druggability.
This paper will systematically review the chemical structure and physicochemical properties of ethyl coumarate, plant origin and extraction methods, pharmacological activity and mechanism of action, druggability evaluation and pharmacokinetic characteristics, combined with its clinical application prospects and future development directions, aiming to provide comprehensive and in-depth reference materials for researchers in related fields.
The chemical name of ethyl paracoumarate is Ethyl(E)-p-hydroxycinnamate, with the molecular formula C11H12O3 and a molecular weight of 192.2140. Its structural features include a para-hydroxyl-substituted benzene ring and a cis-4-hydroxycinnamate ethyl backbone, making it a typical hydroxycinnamate compound. In the structural formula, the hydroxyl group (-OH) on the benzene ring imparts strong antioxidant activity, while the ethyl ester group enhances the molecule's lipid solubility and enhances cell membrane permeability.
In terms of physicochemical properties, the LogP value of ethyl coumarate is 2.5930, indicating moderate lipophilicity, which facilitates transmembrane absorption and distribution in the body. The topological pole surface area (TPSA) is 46.53 Ų, further supporting its good bioavailability. Its water solubility is 0.5818, indicating a certain solubility in water, but it is more suitable for lipid environments. The high permeability of the blood-brain barrier suggests its potential for central nervous system function. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. Ames-induced mutagenic test results were zero, supporting its good safety.
Ethyl coumarate is widely present in various plants, especially in pollen, flowers, and fruits. Common plants rich in ethyl coumarate include Nepenthes spp., certain orchids, and various pollen samples. Its natural form is mostly free esters or bound states, and extraction and purification techniques are crucial for maintaining its yield and activity.
Traditional extraction methods mainly use organic solvent extraction methods, such as ethanol, methanol, or ethyl acetate, combined with ultrasound-assisted extraction (UAE) or microwave-assisted extraction (MAE) technologies, which can improve extraction efficiency and purity. The extract undergoes liquid-liquid separation, column chromatography, and high-performance liquid chromatography (HPLC) purification, ultimately yielding high-purity ethyl coumarate. In recent years, green extraction technologies such as supercritical CO2 extraction have also been applied to extract ethyl coumarate, balancing environmental friendliness with efficient recovery.
Ethyl coumarate, as a non-competitive reversible tyrosinase inhibitor, has an IC50 of 4.89 μg/mL and a Ki of 1.83 μg/mL, demonstrating strong enzyme activity inhibition. Tyrosinase is a key enzyme in melanin biosynthesis, catalyzing the conversion of L-tyrosine to dopa and dopaquinone, regulating skin pigmentation. By inhibiting tyrosinase activity, ethyl coumarate can effectively reduce melanin production, offering potential for whitening and preventing pigmentation spots.
Ethyl coumarate exhibits significant antioxidant activity, scavenging free radicals and reducing cell damage caused by oxidative stress. Its antioxidant mechanism involves activating the NFE2L2/NRF2 signaling pathway, promoting the expression of downstream antioxidant enzymes such as superoxide dismutase (SOD1, SOD2), catalase peroxide (CAT), glutathione peroxidase (GPX1), and heme oxygenase 1 (HMOX1), thereby enhancing cellular antioxidant defense capabilities. Additionally, ethyl coumarate regulates the activity of matrix metalloproteinases (MMP1, MMP3), slows down tissue matrix degradation, and has anti-inflammatory and anti-aging potential.
In addition to tyrosinase inhibition and antioxidant effects, ethyl coumarate also exhibits multiple biological activities including anti-inflammatory, antibacterial, and neuroprotective effects. Its high permeability to the blood-brain barrier gives it potential application value in the prevention and treatment of neurodegenerative diseases. In addition, research on ethyl coumarate in enhancing the medicinal value of plant pollen, cosmetic whitening formulations, and fruit preservation is also increasing.
Ethyl coumarate induces conformational changes in the tyrosinase catalytic region, altering the binding strength between L-tyrosine and enzymes, thereby achieving non-competitive inhibition. Its inhibitory mechanism does not rely on direct binding to intrazymatic copper ions, distinguishing it from traditional copper-chelated tyrosinase inhibitors and reducing potential metal ion-related side effects.
In terms of antioxidant mechanisms, ethyl coumarate activates the NFE2L2/NRF2 signaling pathway, promoting transcription and expression of antioxidant enzyme genes, and enhancing the cell's ability to clear reactive oxygen species (ROS). By regulating the expression of MMP1 and MMP3, it inhibits collagen degradation, delaying tissue aging and inflammatory responses. Additionally, its regulation of antioxidant enzymes such as SOD1, SOD2, CAT, and GPX1 helps maintain intracellular redox balance.
Molecular docking and fluorescence quenching experiments showed that the binding of ethyl coumarate to tyrosinase led to changes in enzyme conformation, effectively quenching the enzyme's intrinsic fluorescence, supporting its mode of action as a non-competitive inhibitor.
Druggability evaluation of ethyl coumarate shows it has good pharmacokinetic characteristics. Molecular weight 192.2140 complies with the Lipinski rule, LogP value is 2.5930, moderate, favorable for oral absorption and cell membrane penetration. The TPSA is 46.53 Ų, supporting its good bioavailability and blood-brain barrier permeability, suggesting its potential in treating central nervous system diseases.
It has moderate water solubility (0.5818), ensuring a certain plasma solubility in vivo distribution while facilitating the penetration of fat-soluble tissues. hERG channel inhibition negative, reducing the risk of cardiotoxicity. The Ames test was negative, indicating low genotoxicity risk and relatively high safety.
Pharmacokinetic studies show that ethyl coumarate is rapidly absorbed orally, plasma concentration peaks are short, widely distributed, and the metabolic pathway mainly involves hepatic enzyme systems for ester bond hydrolysis and corresponding phase I and phase II metabolic reactions. Its metabolites have certain biological activity and may work synergistically.
Ethyl coumarate shows broad application prospects in multiple fields due to its remarkable tyrosinase inhibition and antioxidant activity.
As a non-competitive tyrosinase inhibitor, ethyl coumarate has potential in treating pigmentation, melasma, and other skin diseases. Its good safety and druggability provide ideal candidate molecules for developing new whitening drugs. Moreover, their antioxidant and neuroprotective effects make them worthy of in-depth research in adjunctive therapy for neurodegenerative diseases such as Parkinson's and Alzheimer's.
Ethyl coumarate has been used in many whitening skincare products, effectively inhibiting melanin production, reducing skin spots, and improving uneven skin tone. Its natural source and safety advantages meet modern consumers' demand for green and natural cosmetics.
By utilizing the antioxidant properties of ethyl coumarate, we have developed pollen-based natural preservatives, effectively extending the shelf life of fruits and agricultural products, reducing oxidation and spoilage, and improving food safety and quality.
In the future, pharmacokinetics, toxicology, and preclinical evaluations of ethyl coumarate should be strengthened to improve its safety and efficacy data. Based on its mechanism of action, structural modifications and derivative synthesis are designed to enhance activity and selectivity, expanding its applications in anti-inflammatory and antitumor fields. At the same time, by combining nanocarrier technology, its bioavailability and targeting are improved to promote clinical translation.
Ethyl coumarate, as a non-competitive reversible tyrosinase inhibitor of natural origin, demonstrates broad application potential due to its unique mechanism of action, good pharmacological activity, and druggability. Its research in antioxidant, whitening, anti-inflammatory, and food preservation has deepened, providing new ideas for the development of natural product pharmacology and related industries. In the future, through multidisciplinary collaboration, optimizing its structure and formulations, and promoting the translation of ethyl coumarate for clinical applications, it will contribute greater value to human health.
Shenshuai
Wenjing
Hedandan
