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p-Coumaric Acid Ethyl Ester

Alias: pCoumaric Acid Ethyl Ester; p Coumaric Acid Ethyl Ester
Cat No.:V39897 Purity: ≥98%
p-Coumaric Acid Ethyl Ester (Ethyl (E)-p-hydroxycinnamate; Ethyl trans-4-hydroxycinnamate) is the ethyl ester form of p-Coumaric acid.
p-Coumaric Acid Ethyl Ester
p-Coumaric Acid Ethyl Ester Chemical Structure CAS No.: 7362-39-2
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
p-Coumaric Acid Ethyl Ester (Ethyl (E)-p-hydroxycinnamate; Ethyl trans-4-hydroxycinnamate) is the ethyl ester form of p-Coumaric acid. p-Coumaric Acid may be utilized in the research/study of autoimmune inflammatory diseases (like rheumatoid arthritis) and is an immunosuppressant.
p-Coumaric Acid Ethyl Ester (CAS 7362-39-2) is the ethyl ester form of p-coumaric acid, a naturally occurring phenolic acid found in various plants. This compound has molecular formula C₁₁H₁₂O₃ and molecular weight 192.21 g/mol. It appears as a solid and is soluble in organic solvents. p-Coumaric Acid Ethyl Ester serves as a non-competitive, reversible inhibitor of tyrosinase with an IC₅₀ of 4.89 μg/mL and a Ki of 1.83 μg/mL. The compound is known for its antioxidant properties and has applications in pharmaceuticals, cosmetics, and fruit preservation products. It is also investigated for its antimicrobial activity and potential therapeutic effects. This compound is intended for research use only as a biochemical tool and reference standard.
Biological Activity I Assay Protocols (From Reference)
Targets
p-Coumaric Acid Ethyl Ester primarily targets aldose reductase and tyrosinase. Aldose reductase is an enzyme involved in glucose metabolism; its inhibition is a strategy to alleviate symptoms of diabetic complications. Tyrosinase is a key enzyme in melanin production; its inhibition can lead to reduced pigmentation. The compound inhibits tyrosinase in a noncompetitive manner by inducing conformational changes within the catalytic domain without interfering with copper ion binding. It also exhibits notable antimicrobial activity against various pathogens and has been reported to modulate carbonic anhydrase, demonstrating multifaceted bioactive properties.
ln Vitro
In vitro, p-Coumaric Acid Ethyl Ester demonstrates potent tyrosinase inhibition with an IC₅₀ of 4.89 μg/mL and a Ki of 1.83 μg/mL as a non-competitive, reversible inhibitor. The compound quells the intrinsic fluorescence of tyrosinase and alters the binding affinity of L-tyrosine by inducing conformational changes within the catalytic domain. It has been shown to strongly inhibit aldose reductase with a half inhibitory concentration of 1.92 μM. The compound exhibits moderate free radical scavenging ability as evaluated by DPPH assays and demonstrates antimicrobial activity, effectively inhibiting the growth of Athelia rolfsii (8.0%-45.0%) and Pythium sp.. Its antioxidant properties contribute to potential uses in cosmetics and pharmaceuticals.
ln Vivo
In vivo data for p-Coumaric Acid Ethyl Ester are limited as the compound is primarily used as a research tool. As a derivative of p-coumaric acid, which has documented immunomodulatory properties for autoimmune inflammatory diseases such as rheumatoid arthritis, the ethyl ester may exhibit similar biological activities. The compound's antioxidant and anti-inflammatory properties suggest potential therapeutic applications. However, detailed in vivo pharmacokinetic and efficacy studies are not extensively reported. Further investigation is needed to establish its bioavailability, tissue distribution, and therapeutic potential in animal models. The compound is supplied for research purposes and is not intended for human therapeutic use.
Enzyme Assay
In vitro enzyme/receptor binding (non-cellular) assays for p-Coumaric Acid Ethyl Ester typically involve tyrosinase inhibition studies using mushroom tyrosinase and L-tyrosine or L-DOPA as substrates. The enzyme is incubated with varying concentrations of the compound in phosphate buffer (pH 6.8) at 25°C. The reaction is monitored spectrophotometrically by measuring the formation of dopachrome at 475 nm. IC₅₀ values are calculated from concentration-response curves, and the inhibition mechanism (competitive vs. non-competitive) is determined via Lineweaver-Burk plots. For aldose reductase inhibition, assays use purified enzyme with DL-glyceraldehyde as substrate, monitoring NADPH oxidation at 340 nm. DPPH radical scavenging assays evaluate antioxidant activity by measuring absorbance decrease at 517 nm.
Cell Assay
In vitro cellular experiments with p-Coumaric Acid Ethyl Ester are performed using various cell lines to assess its biological activities. Melanoma cells such as B16F10 are commonly used to evaluate tyrosinase inhibition and melanin production. Cells are cultured in DMEM with 10% FBS and treated with varying concentrations of the compound (typically 1-100 μg/mL) for 24-72 hours. Melanin content is measured spectrophotometrically after cell lysis, and tyrosinase activity is assessed using L-DOPA as substrate. Cell viability is evaluated using MTT assays to distinguish cytotoxic effects from melanin inhibition. For antimicrobial studies, bacterial or fungal cultures are treated with the compound, and growth inhibition is measured by optical density or colony counting. Cells are maintained at 37°C in 5% CO₂.
Animal Protocol
In vivo animal studies with p-Coumaric Acid Ethyl Ester have not been extensively reported in the literature. As a research compound primarily used for in vitro and biochemical studies, standard in vivo efficacy models have not been well established. However, for related phenolic acid derivatives, animal models of inflammation, diabetes, or skin pigmentation disorders may be employed. Typical studies would involve oral or topical administration of the compound to rodents, with endpoints including inflammatory markers, blood glucose levels, or skin pigmentation assessment. The compound's antioxidant properties suggest potential applications in oxidative stress models. Further preclinical investigations are needed to establish appropriate in vivo models and dosing regimens for this compound.
ADME/Pharmacokinetics
Comprehensive pharmacokinetic data for p-Coumaric Acid Ethyl Ester are not extensively reported in the available literature. The compound has a molecular weight of 192.21 g/mol and is soluble in organic solvents. As an ester derivative of p-coumaric acid, it is expected to be hydrolyzed by esterases to release the parent acid. Storage recommendations include -20°C for powder (3 years) and -20°C for solution (6 months). The compound shows moderate free radical scavenging ability. Detailed parameters such as half-life, bioavailability, clearance, and volume of distribution require further investigation from primary research publications. The compound is intended for research use only and is not approved for therapeutic applications.
Toxicity/Toxicokinetics
Toxicological information for p-Coumaric Acid Ethyl Ester is not extensively detailed. As a phenolic compound and ester derivative, standard safety precautions for handling research chemicals apply. The compound should be handled with appropriate personal protective equipment including gloves, safety goggles, and lab coat in a well-ventilated area. It is classified as a reference compound for research purposes and is not intended for human consumption. The compound should be stored at -20°C in powder form for up to 3 years or in solution at -20°C for 6 months. Based on its structural similarity to naturally occurring p-coumaric acid, it is expected to have a relatively favorable safety profile at research-use concentrations, though comprehensive toxicological studies have not been reported.
References

[1]. Hydroxycinnamic acid as a novel scaffold for the development of cyclooxygenase-2 inhibitors. RSC Advances. Issue 72, 2015.

[2]. Immunomodulatory and anti-inflammatory effect of p-coumaric acid, a common dietary polyphenol on experimental inflammation in rats. Inflammation. 2013 Feb;36(1):169-76.

Additional Infomation
Ethyl p-coumarate is a cinnamic ester. Ethyl (E)-3-(4-hydroxyphenyl)acrylate has been found in bees, and relevant data have been reported.
p-Coumaric Acid Ethyl Ester (CAS 7362-39-2) is a multifaceted bioactive agent demonstrating inhibitory activities across different biological systems. It serves as a non-competitive, reversible inhibitor of tyrosinase with an IC₅₀ of 4.89 μg/mL and a Ki of 1.83 μg/mL. The compound has molecular formula C₁₁H₁₂O₃ and molecular weight 192.21 g/mol. It exhibits antioxidant properties and has applications in pharmaceuticals, cosmetics, and fruit preservation products. p-Coumaric Acid Ethyl Ester is also investigated for its potential therapeutic effects in medicine. Purity is typically >98%. The compound is intended for research use only as a tyrosinase inhibitor and biochemical tool. Storage: powder at -20°C for 3 years; solution at -20°C for 6 months.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C₁₁H₁₂O₃
Molecular Weight
192.21
Exact Mass
192.078
CAS #
7362-39-2
PubChem CID
676946
Appearance
Light yellow to light brown solid powder
Density
1.2±0.1 g/cm3
Boiling Point
320.2±17.0 °C at 760 mmHg
Melting Point
65-68 °C
Flash Point
136.5±13.7 °C
Vapour Pressure
0.0±0.7 mmHg at 25°C
Index of Refraction
1.581
LogP
2.17
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
4
Heavy Atom Count
14
Complexity
203
Defined Atom Stereocenter Count
0
SMILES
CCOC(=O)/C=C/C1=CC=C(C=C1)O
InChi Key
ZOQCEVXVQCPESC-VMPITWQZSA-N
InChi Code
InChI=1S/C11H12O3/c1-2-14-11(13)8-5-9-3-6-10(12)7-4-9/h3-8,12H,2H2,1H3/b8-5+
Chemical Name
ethyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms
pCoumaric Acid Ethyl Ester; p Coumaric Acid Ethyl Ester
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~520.26 mM)
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 5.2026 mL 26.0132 mL 52.0264 mL
5 mM 1.0405 mL 5.2026 mL 10.4053 mL
10 mM 0.5203 mL 2.6013 mL 5.2026 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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