p-Hydroxyphenethyl trans-ferulate

Base Information

• Chemical Name: p-Hydroxyphenethyl trans-ferulate
• CAS No.: 84873-15-4
• Molecular Formula: C18H18O5
• Molecular Weight: 314.338
• DSSTox Substance ID: DTXSID10348425
• Nikkaji Number: J637.872B,J2.482.384I
• Pharos Ligand ID: 92DKPWL9DRJC
• Metabolomics Workbench ID: 45744
• ChEMBL ID: CHEMBL481245
• Mol file: 84873-15-4.mol

Synonyms:hydroxyphenethylferulate;p-hydroxyphenethyl trans-ferulate

Chemical Property of p-Hydroxyphenethyl trans-ferulate

Chemical Property:

• Vapor Pressure: 7.43E-12mmHg at 25°C
• Melting Point: 168-169℃
• Boiling Point: 530.1°Cat760mmHg
• Flash Point: 193.3°C
• PSA: 75.99000
• Density: 1.265g/cm³
• LogP: 2.90550
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 314.11542367
• Heavy Atom Count: 23
• Complexity: 387

Purity/Quality:

≥95% ^*data from raw suppliers

p-Hydroxyphenethyltrans-ferulate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)C=CC(=O)OCCC2=CC=C(C=C2)O)O
• Isomeric SMILES: COC1=C(C=CC(=C1)/C=C/C(=O)OCCC2=CC=C(C=C2)O)O

Technology Process of p-Hydroxyphenethyl trans-ferulate

There total 3 articles about p-Hydroxyphenethyl trans-ferulate 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: 65.0%

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6,537-98-4) + p-hydroxyphenethyl alcohol (501-94-0) → (2E)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoic acid 2-(4-hydroxyphenyl)ethyl ester (84873-15-4)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20 ℃; chemoselective reaction; Inert atmosphere;

DOI:10.1016/j.bmc.2015.10.014

Reference yield:

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6,537-98-4) → (2E)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoic acid 2-(4-hydroxyphenyl)ethyl ester (84873-15-4)

Guidance literature:

Multi-step reaction with 2 steps

1: thionyl chloride / pyridine; diethyl ether / 0.17 h / 0 °C

2: pyridine; diethyl ether / 0.5 h / 40 °C

With thionyl chloride; In pyridine; diethyl ether;

DOI:10.1248/cpb.30.4554

Reference yield:

p-hydroxyphenethyl alcohol (501-94-0) + trans-4-hydroxy-3-methoxycinnamic acid chloride (138769-50-3,108608-04-4) → (2E)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoic acid 2-(4-hydroxyphenyl)ethyl ester (84873-15-4)

Guidance literature:

In pyridine; diethyl ether; at 40 ℃; for 0.5h;

DOI:10.1248/cpb.30.4554

upstream raw materials:

p-hydroxyphenethyl alcohol

trans-4-hydroxy-3-methoxycinnamic acid chloride

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

Downstream raw materials:

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

2-phenylethanol

Refernces

• 1、 Mohyeldin, Mohamed M.,Busnena, Belnaser A.,Akl, Mohamed R.,Dragoi, Ana Maria,Cardelli, James A.,El Sayed, Khalid A.. "Novel c-Met inhibitory olive secoiridoid semisynthetic analogs for the control of invasive breast cancer". supporting information. p. 299 - 315. Retrieved 2016/06/09.
• 2、 -. "PARA-COUMARIC ACID OR PARA-HYDROXYCINNAMIC ACID DERIVATIVES AND THEIR USE IN COSMETIC OR DERMATOLOGICAL COMPOSITIONS". Page/Page column 7. . Retrieved 2010/11/28.