68573-23-9

Basic information

• Product Name: N-FERULOYLSEROTONIN
• Synonyms: N-FERULOYLSEROTONIN;N-[2-(5-Hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxy-3-Methoxyphenyl)-2-propenaMide;NSC 369502;Moschamine
• CAS NO: 68573-23-9
• Molecular Formula: C₂₀H₂₀N₂O₄
• Molecular Weight: 352.3838
• Product Categories: Aromatics;Heterocycles;Indole Derivatives;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 68573-23-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 110-114 °C
• Boiling Point: 705.6°Cat760mmHg
• Flash Point: 380.5°C
• Appearance: /
• Density: 1.338g/cm³
• Vapor Pressure: 1.43E-20mmHg at 25°C
• Refractive Index: 1.703
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 9.78±0.35(Predicted)
• CAS DataBase Reference: N-FERULOYLSEROTONIN(CAS DataBase Reference)
• NIST Chemistry Reference: N-FERULOYLSEROTONIN(68573-23-9)
• EPA Substance Registry System: N-FERULOYLSEROTONIN(68573-23-9)

Safety Data

• Hazardous Substances Data: 68573-23-9(Hazardous Substances Data)

Usage

Chemical Properties

Pale Beige Solid

Uses

N-Feruloylserotonin is a conjugated serotonin compound that has been identified as the antioxidative component from the seed of Carthamus tinctorius. N-Feruloylserotonin displayed protective effects on oxidative damage in rat pheochromocytoma cells.

InChI:InChI=1/C20H20N2O4/c1-26-19-10-13(2-6-18(19)24)3-7-20(25)21-9-8-14-12-22-17-5-4-15(23)11-16(14)17/h2-7,10-12,22-24H,8-9H2,1H3,(H,21,25)

Upstream product

• 50-67-9 3-(2-aminoethyl)-1H-indol-5-ol 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 153-98-0 serotonin hydrochloride 
• 61-54-1 tryptamine 
• 212707-64-7 (E)-N-[2-(2,3-Dihydro-1H-indol-3-yl)-ethyl]-3-(4-hydroxy-3-methoxy-phenyl)-acrylamide 
• 96014-22-1 (E)-N-(2-(1H-indol-3-yl)ethyl)-3-(4-hydroxy-3-methoxyphenyl)acrylamide 
• 212707-69-2 (E)-N-[2-(1-Hydroxy-1H-indol-3-yl)-ethyl]-3-(4-hydroxy-3-methoxy-phenyl)-acrylamide 

Downstream Products

• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 76410-51-0 N-feruloylserotonin diacetate 

Relevant articles and documents

Synthesis of amide and ester derivatives of cinnamic acid and its analogs: Evaluation of their free radical scavenging and monoamine oxidase and cholinesterase inhibitory activities

A series of cinnamic acid derivatives, amides (1–12) and esters (13–22), were synthesized, and structure–activity relationships for antioxidant activity, and monoamine oxidases (MAO) A and B, acetylcholinesterase, and butyrylcholinesterase (BChE) inhibitory activities were analyzed. Among the synthesized compounds, compounds 1–10, 12–18, and rosmarinic acid (23), which contained catechol, o-methoxyphenol or 5-hydroxy-indole moieties, showed potent 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity. Compounds 9–11, 15, 17–22 showed potent and selective MAO-B inhibitory activity. Compound 20 was the most potent inhibitor of MAO-B. Compounds 18 and 21 showed moderate BChE inhibitory activity. In addition, compound 18 showed potent antioxidant activity and MAO-B inhibitory activity. In a comparison of the cinnamic acid amides and esters, the amides exhibited more potent DPPH free radical scavenging activity, while the esters showed stronger inhibitory activities against MAO-B and BChE. These results suggested that cinnamic acid derivatives such as compound 18, p-coumaric acid 3,4-dihydroxyphenethyl ester, and compound 20, p-coumaric acid phenethyl ester, may serve as lead compounds for the development of novel MAO-B inhibitors and candidate lead compounds for the prevention or treatment of Alzheimer’s disease.

N-[(Dihydroxyphenyl)acyl]serotonins as potent inhibitors of tyrosinase from mouse and human melanoma cells

A series of N-acyl derivatives of tyramine, tryptamine, and serotonin were synthesized and tested on anti-melanogenic activity. The serotonin derivatives such as N-caffeoylserotonin (3) and N-protocatechuoylserotonin (9) were inhibitory to tyrosinase from

Serotonin derivatives, major safflower (Carthamus tinctorius L.) seed antioxidants, inhibit Low-Density Lipoprotein (LDL) oxidation and atherosclerosis in apolipoprotein E-deficient mice

The effects of defatted safflower seed extract and its phenolic constituents, serotonin derivatives, on atherosclerosis were studied. Ethanol-ethyl acetate extract of safflower seeds (SSE) inhibited low-density lipoprotein (LDL) oxidation induced in vitro