Methyl p-coumarate (Methyl 4-hydroxycinnamate), an esterified analogue of p-coumaric acid (pCA) extracted from the flowers of Trixis michuacana var longifolia. Methyl p-coumarate inhibits melanin formation in B16 mouse melanoma cells. Methyl p-coumarate also has strong in vitro inhibitory effects against Alternaria and other pathogens.

Physicochemical Properties

Molecular Formula	C10H10O3
Molecular Weight	178.18
Exact Mass	178.062
CAS #	3943-97-3
Related CAS #	(E)-Methyl 4-coumarate;19367-38-5
PubChem CID	5319562
Appearance	Off-white to light yellow solid powder
Density	1.2±0.1 g/cm3
Boiling Point	306.6±17.0 °C at 760 mmHg
Melting Point	144-145ºC
Flash Point	132.8±13.7 °C
Vapour Pressure	0.0±0.7 mmHg at 25°C
Index of Refraction	1.593
LogP	1.64
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	3
Heavy Atom Count	13
Complexity	190
Defined Atom Stereocenter Count	0
SMILES	COC(=O)/C=C/C1=CC=C(C=C1)O
InChi Key	NITWSHWHQAQBAW-QPJJXVBHSA-N
InChi Code	InChI=1S/C10H10O3/c1-13-10(12)7-4-8-2-5-9(11)6-3-8/h2-7,11H,1H3/b7-4+
Chemical Name	methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
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)

Biological Activity

References

[1]. Methyl p-coumarate, a melanin formation inhibitor in B16 mouse melanoma cells. Bioorg Med Chem. 2004 Oct 15;12(20):5349-54. [2]. Defense Responses, Induced by p-Coumaric Acid and Methyl p-Coumarate, of Jujube ( Ziziphus jujuba Mill.) Fruit against Black Spot Rot Caused by Alternaria alternate. J Agric Food Chem. 2019 Mar 13;67(10):2801-2810. [3]. Methyl P-Coumarate Ameliorates the Inflammatory Response in Activated-Airway Epithelial Cells and Mice with Allergic Asthma. Int J Mol Sci. 2022 Nov 28;23(23):14909.

Additional Infomation

4-coumaric acid methyl ester is a cinnamate ester that is the methyl ester of 4-coumaric acid. It has a role as a melanin synthesis inhibitor, a fungal metabolite, an anti-inflammatory agent, an antifungal agent and a plant metabolite. It is a cinnamate ester, a member of phenols and a methyl ester. It is functionally related to a 4-coumaric acid. Methyl 4-hydroxycinnamate has been reported in Alpinia blepharocalyx, Gmelina asiatica, and other organisms with data available.

Solubility Data

Solubility (In Vitro)

DMSO : 100 mg/mL (561.23 mM)

Solubility (In Vivo)

Solubility in Formulation 1: 2.5 mg/mL (14.03 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (14.03 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. 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. Solubility in Formulation 3: ≥ 2.5 mg/mL (14.03 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	5.6123 mL	28.0615 mL	56.1230 mL
	5 mM	1.1225 mL	5.6123 mL	11.2246 mL
	10 mM	0.5612 mL	2.8062 mL	5.6123 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.