N-(p-Coumaroyl) Serotonin is a polyphenol extracted from safflower seeds that displays antioxidant, antiatherogenic, and anti-inflammatory activities. N-(p-Coumaroyl) Serotonin reduces the PDGF-induced effects on PDGFR tyrosine phosphorylation and Ca2+ release in the sarcoplasmic reticulum. N-(p-Coumaroyl) Serotonin can improve atherosclerosis and aortic wall enlargement and is widely utilized in atherosclerosis research.

Physicochemical Properties

Molecular Formula	C19H18N2O3
Molecular Weight	322.36
Exact Mass	322.132
CAS #	68573-24-0
PubChem CID	5458879
Appearance	Off-white to light yellow solid powder
Density	1.346g/cm3
Boiling Point	694.2ºC at 760 mmHg
Melting Point	205 - 206 °C
Flash Point	373.6ºC
Index of Refraction	1.73
LogP	3.342
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	5
Heavy Atom Count	24
Complexity	446
Defined Atom Stereocenter Count	0
SMILES	C1=CC(=CC=C1/C=C/C(=O)NCCC2=CNC3=C2C=C(C=C3)O)O
InChi Key	WLZPAFGVOWCVMG-FPYGCLRLSA-N
InChi Code	InChI=1S/C19H18N2O3/c22-15-4-1-13(2-5-15)3-8-19(24)20-10-9-14-12-21-18-7-6-16(23)11-17(14)18/h1-8,11-12,21-23H,9-10H2,(H,20,24)/b8-3+
Chemical Name	(E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxyphenyl)prop-2-enamide
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]. Effect of N-(p-coumaroyl)serotonin and N-feruloylserotonin, major anti-atherogenic polyphenols in safflower seed, on vasodilation, proliferation and migration of vascular smooth muscle cells. Mol Nutr Food Res. 2011 Oct;55(10):156. [2]. Safflower seed polyphenols (N-(p-coumaroyl)serotonin and N-feruloylserotonin) ameliorate atherosclerosis and distensibility of the aortic wall in Kurosawa and Kusanagi-hypercholesterolemic (KHC) rabbits.Hypertens Res.

Additional Infomation

N6-cis-p-Coumaroylserotonin is a member of hydroxyindoles and a carboxamide. It is functionally related to a serotonin. N-Coumaroyl serotonin has been reported in Ipomoea obscura, Carthamus tinctorius, and other organisms with data available.

Solubility Data

Solubility (In Vitro)

DMSO: 250 mg/mL (775.53 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.08 mg/mL (6.45 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% 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 20.8 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: ≥ 2.08 mg/mL (6.45 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 20.8 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: ≥ 2.08 mg/mL (6.45 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 20.8 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	3.1021 mL	15.5106 mL	31.0212 mL
	5 mM	0.6204 mL	3.1021 mL	6.2042 mL
	10 mM	0.3102 mL	1.5511 mL	3.1021 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.