(S)-2-Ethoxy-3-(4-hydroxy-phenyl)-propionic acid

Base Information

• Chemical Name: (S)-2-Ethoxy-3-(4-hydroxy-phenyl)-propionic acid
• CAS No.: 325793-65-5
• Molecular Formula: C11H14 O4
• Molecular Weight: 210.23
• Hs Code.: 2918990090
• European Community (EC) Number: 676-074-9
• DSSTox Substance ID: DTXSID70431569
• Nikkaji Number: J2.803.853D
• Wikidata: Q76414558
• Mol file: 325793-65-5.mol

Synonyms:325793-65-5;(S)-2-Ethoxy-3-(4-hydroxy-phenyl)-propionic acid;(S)-2-ethoxy-3-(4-hydroxyphenyl)propanoic acid;(2s)-2-ethoxy-3-(4-hydroxyphenyl)propanoic acid;(S)-2-Ethoxy-3-(4-hydroxyphenyl)propanoicacid;(s)-2-ethoxy-3-(4-hydroxyphenyl)propionic acid;SCHEMBL3233074;DTXSID70431569;FMJUDUJLTNVWCH-JTQLQIEISA-N;MFCD06796579;AKOS015891394;AS-37398;CS-0172245;A13356;(S)-alpha-Ethoxy-4-hydroxybenzenepropionic acid;(2S)-2-ethoxy-3-(4-hydroxyphenyl)-propionic acid;J-018792;(S)-2-ethoxy-3-(4-hydroxy-phenyl)-propionic acid, AldrichCPR

Chemical Property of (S)-2-Ethoxy-3-(4-hydroxy-phenyl)-propionic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.552
• Boiling Point: 390.8°Cat760mmHg
• Flash Point: 153.4°C
• PSA: 66.76000
• Density: 1.225g/cm³
• LogP: 1.42440
• Storage Temp.: 2-8°C
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 210.08920892
• Heavy Atom Count: 15
• Complexity: 197

Purity/Quality:

98% ^*data from raw suppliers

(S)-2-Ethoxy-3-(4-hydroxyphenyl)propionicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(CC1=CC=C(C=C1)O)C(=O)O
• Isomeric SMILES: CCO[C@@H](CC1=CC=C(C=C1)O)C(=O)O
• Uses: (S)-2-Ethoxy-3-(4-hydroxyphenyl)propionic Acid, is used in the synthesis of the human peroxisome proliferator-activated receptor (PPAR) agonist ragaglitazar.

Technology Process of (S)-2-Ethoxy-3-(4-hydroxy-phenyl)-propionic acid

There total 30 articles about (S)-2-Ethoxy-3-(4-hydroxy-phenyl)-propionic acid 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: 80.0%

(S)-2-ethoxy-3-(4-methoxyphenyl)propanoic acid (343880-41-1) → (S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2) + (2S)-2-Ethoxy-3-(4-hydroxyphenyl)propanoic acid (325793-65-5)

Guidance literature:

With hydrogen iodide; In water;

DOI:10.1021/op040006z

Reference yield: 52.0%

(S)-2-ethoxy-3-(4-methoxyphenyl)propanoic acid (343880-41-1) + Octanethiol (111-88-6) → (2S)-2-Ethoxy-3-(4-hydroxyphenyl)propanoic acid (325793-65-5)

Guidance literature:

With sodium hydroxide; In water; ethyl acetate;

Reference yield: 48.0%

ethyl 2-ethoxy-3-(4-hydroxy-phenyl)-propionate (197299-16-4) → ethyl (2R)-2-ethoxy-3-(4-hydroxyphenyl)propanoate (222555-05-7) + (2S)-2-Ethoxy-3-(4-hydroxyphenyl)propanoic acid (325793-65-5)

Guidance literature:

With Aspergillus oryzae hydrolytic enzyme mixture; In aq. phosphate buffer; at 20 ℃; for 16h; pH=7; Reagent/catalyst; Time; Concentration; Solvent; enantioselective reaction; Catalytic behavior; Resolution of racemate; Large scale; Enzymatic reaction;

DOI:10.1021/op0256035

upstream raw materials:

ethyl 2-ethoxy-3-(4-hydroxy-phenyl)-propionate

p-benzyloxybenzaldehyde

3-(4-benzyloxy-phenyl)-2-ethoxy-acrylic acid ethyl ester

3-(4-benzyloxyphenyl)-(S)-2-ethoxy-N-(2-hydroxy-(R)-1-phenylethyl)propanoic amide

Downstream raw materials:

(S)-2-ethoxy-3-(4-((5-(3-methoxyphenyl)-3-methylthiophen-2-yl)methoxy)phenyl)propionic acid ethyl ester

(S)-2-ethoxy-3-(4-((5-(3-methoxyphenyl)-3-methylthiophen-2-yl)methoxy)phenyl)propionic acid

(S)-3-(4-((5-bromo-3-methylthiophen-2-yl)methoxy)phenyl)-2-ethoxypropionic acid ethyl ester

(S)-2-ethoxy-3-(4-((3-methylthiophen-2-yl)methoxy)phenyl)propionic acid ethyl ester

Refernces

• 1、 Mujahid,Kunte,Muthukrishnan. "A new enantioselective synthesis of (S)-2-ethoxy-3-(4-hydroxyphenyl) propanoic acid esters (EEHP and IEHP), useful pharmaceutical intermediates of PPAR agonists". supporting information. p. 3223 - 3226. Retrieved 2014/06/09.
• 2、 -. "NOVEL PHENYLPROPIONIC ACID DERIVATIVES AS PEROXISOME PROLIFERATOR-ACTIVATED GAMMA RECEPTOR MODULATORS, METHOD OF THE SAME, AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME". Page/Page column 29; 30. . Retrieved 2010/04/23.