N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxyphenyl)prop-2-enamide

Base Information

• Chemical Name: N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxyphenyl)prop-2-enamide
• CAS No.: 68573-24-0
• Molecular Formula: C19H18N2O3
• Molecular Weight: 322.364
• DSSTox Substance ID: DTXSID901313118
• Wikidata: Q105308384,Q105308386
• Mol file: 68573-24-0.mol

Synonyms:N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxyphenyl)prop-2-enamide;DTXSID901313118;AKOS030242666;FT-0665200

Chemical Property of N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxyphenyl)prop-2-enamide

Chemical Property:

• Vapor Pressure: 6.53E-20mmHg at 25°C
• Melting Point: 192-194?C
• Boiling Point: 694.2°Cat760mmHg
• PKA: 9.74±0.30(Predicted)
• Flash Point: 373.6°C
• PSA: 85.35000
• Density: 1.346g/cm³
• LogP: 3.34210
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 322.13174244
• Heavy Atom Count: 24
• Complexity: 446

Purity/Quality:

≥98% ^*data from raw suppliers

N-(p-Coumaroyl)Serotonin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C=CC(=O)NCCC2=CNC3=C2C=C(C=C3)O)O
• Uses: N-(p-Coumaroyl) serotonin is an antioxidative phenolic naturally found in plants, including safflower seed and millet grain. It ameliorates atherosclerosis in vivo, reducing lesion area in mice and rabbits. N-(p-Coumaroyl) serotonin also suppresses inflammatory cytokine generation by human monocytes, augments fibroblast proliferation, and promotes relaxation of vascular smooth muscle cells in vitro.

Technology Process of N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxyphenyl)prop-2-enamide

There total 7 articles about N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxyphenyl)prop-2-enamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

3-(2-aminoethyl)-1H-indol-5-ol (50-67-9) + p-Coumaric Acid (7400-08-0,50940-26-6) → N-p-coumaroylserotonin (68573-24-0)

Guidance literature:

p-Coumaric Acid; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 0.5h;

3-(2-aminoethyl)-1H-indol-5-ol; With triethylamine; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; Inert atmosphere;

DOI:10.1248/cpb.c17-00416

Reference yield: 62.0%

→ N-p-coumaroylserotonin (68573-24-0)

Guidance literature:

Reference yield: 5.0%

(E)-N-[2-(1-Hydroxy-1H-indol-3-yl)-ethyl]-3-(4-hydroxy-phenyl)-acrylamide (212707-68-1) → N-p-coumaroylserotonin (68573-24-0)

Guidance literature:

With formic acid;

DOI:10.3987/COM-98-8156

upstream raw materials:

3-(2-aminoethyl)-1H-indol-5-ol

p-Coumaric Acid

(E)-N-[2-(1-Hydroxy-1H-indol-3-yl)-ethyl]-3-(4-hydroxy-phenyl)-acrylamide

tryptamine

Downstream raw materials:

N-(p-coumaroyl)serotonin diacetate

Refernces

• 1、 -. "TRYPTAMINE DERIVATIVES, THEIR PREPARATION AND THEIR USE IN GASTROPATHY". Paragraph 0101; 0107; 0108; 0111. . Retrieved 2013/08/14.
• 2、 Tanaka, Eiji,Tanaka, Chihiro,Mori, Naoki,Kuwahara, Yasumasa,Tsuda, Mitsuya. "Phenylpropanoid amides of serotonin accumulate in witches' broom diseased bamboo". . p. 965 - 969. Retrieved 2007/10/03.