Cinnamamide, p-hydroxy-N-(p-hydroxyphenethyl)-

Base Information

• Chemical Name: Cinnamamide, p-hydroxy-N-(p-hydroxyphenethyl)-
• CAS No.: 20375-37-5
• Molecular Formula: C₁₇H₁₇NO₃
• Molecular Weight: 283.327
• DSSTox Substance ID: DTXSID20942534
• Wikidata: Q105247026,Q82919552
• Mol file: 20375-37-5.mol

Synonyms:20375-37-5;Cinnamamide, p-hydroxy-N-(p-hydroxyphenethyl)-;3-(4-hydroxyphenyl)-n-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide;MFCD20260399;N-p-Cumaroyltyramin;SCHEMBL2512193;DTXSID20942534;CHEBI:181326;NCI60_040967;SY110811;FT-0775631;B2703-179669;3-(4-Hydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid

Chemical Property of Cinnamamide, p-hydroxy-N-(p-hydroxyphenethyl)-

Chemical Property:

• Vapor Pressure: 2.35E-14mmHg at 25°C
• Melting Point: 247-248 °C
• Boiling Point: 586.5°Cat760mmHg
• PKA: 9.74±0.30(Predicted)
• Flash Point: 308.5°C
• PSA: 73.05000
• Density: 1.248g/cm³
• LogP: 3.31020
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 283.12084340
• Heavy Atom Count: 21
• Complexity: 340

Purity/Quality:

99% ^*data from raw suppliers

p-Coumaroyltyramine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1CCNC(=O)C=CC2=CC=C(C=C2)O)O
• Uses: p-Coumaroyltyramine is a metabolite isolated from Piper septuplinervium.

Technology Process of Cinnamamide, p-hydroxy-N-(p-hydroxyphenethyl)-

There total 6 articles about Cinnamamide, p-hydroxy-N-(p-hydroxyphenethyl)- 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:

p-Iodophenol (540-38-5) + N-(4-hydroxyphenethyl)acrylamide (80633-44-9) → paprazine (20375-37-5,111129-11-4,36417-86-4)

Guidance literature:

With tetrabutylammomium bromide; palladium diacetate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 130 - 140 ℃; Microwave irradiation; Continuous-flow conditions;

DOI:10.1002/chem.201002102

Reference yield:

tyrosamine (51-67-2) + 4-hydroxycinnamic acid N-hydroxysuccinimide ester (88492-43-7) → paprazine (20375-37-5,111129-11-4,36417-86-4)

Guidance literature:

With sodium hydrogencarbonate; In water; acetone; for 24h;

DOI:10.1016/0031-9422(96)00173-2

Reference yield:

N-<2-(4-Hydroxy-phenyl)-aethyl>-4-acetoxy-trans-zimtsaeureamid (20375-41-1) → paprazine (20375-37-5,111129-11-4,36417-86-4)

Guidance literature:

With sodium carbonate; In ethanol; for 2h; Yield given; Heating;

DOI:10.1248/cpb.40.396

upstream raw materials:

N-<2-(4-Hydroxy-phenyl)-aethyl>-4-acetoxy-trans-zimtsaeureamid

tyrosamine

4-hydroxycinnamic acid N-hydroxysuccinimide ester

tyramine hydrochloride

Downstream raw materials:

diacetyl N-trans-p-coumaroyl tyramine

Refernces

• 1、 Muehlenbeck, Ute,Kortenbusch, Albertus,Barz, Wolfgang. "Formation of hydroxycinnamoylamides and α-hydroxyacetovanillone in cell cultures of Solanum khasianum". . p. 1573 - 1579. Retrieved 2007/10/03.
• 2、 Slatkin,Doorenbos,Harris,Masoud,Quimby,Schiff Jr.. "Chemical constituents of Cannabis sativa L. root.". . p. 1891 - 1892. Retrieved 2007/10/12.