Ethyl (S)-2-Ethoxy-3-(4-hydroxyphenyl)propionate

• CAT Number: R020268
• CAS Number: 222555-06-8
• Molecular Formula: C13H18O4
• Molecular Weight: 238.283
• Purity: ≥95%
• Synonyms: (2S)-2-Ethoxy-3-(4-hydroxyphenyl)propionic Acid Ethyl Ester; (S)-(-)-Ethyl 2-Ethoxy-3-(4-hydroxyphenyl)propanoate; (S)-(-)-Ethyl 2-Ethoxy-3-(4-hydroxyphenyl)propionate; Ethyl (2S)-2-Ethoxy-3-(4-hydroxyphenyl)propanoate; Ethyl (S)-3-(4-Hydroxyphenyl)-
• Storage: -20°C
• IUPAC Name: ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoate
• InChI: InChI=1S/C13H18O4/c1-3-16-12(13(15)17-4-2)9-10-5-7-11(14)8-6-10/h5-8,12,14H,3-4,9H2,1-2H3/t12-/m0/s1
• InChIKey: NEJJCKFYYBEQRQ-LBPRGKRZSA-N
• SMILES: CCOC(CC1=CC=C(C=C1)O)C(=O)OCC

Ethyl (S)-2-Ethoxy-3-(4-hydroxyphenyl)propionate is a high-purity compound essential for advanced pharmaceutical and biochemical research. This ester is crucial for studies involving chiral synthesis, drug development, and metabolic pathways. Known for its stability and specific (S)-configuration, it integrates seamlessly into experimental protocols, providing reliable and consistent results for high-precision investigations in various scientific applications.

Reference

[1]. Facile synthesis of optically pure (S)-3-p-hydroxyphenyllactic acid derivatives
Q. L. Zeng, H. Q. Wang, Z. R. Liu, B. G. Li & Y. F. Zhao; Amino Acids volume 33, pages 537–541 (2007)
Optically pure (S)-3-p-hydroxyphenyllactic acid derivatives are important intermediates of peroxisome proliferator-activated receptor α/γ dual agonists and heteropeptides. Many efforts have been made for synthesis of those intermediates, but there exist some flaws yet. We observed that dielectric constants of organic solvents drastically affected diazotization of O-benzyl-L-tyrosine. Optically pure (S)-3-p-benzyloxyphenyllactic acid was obtained by simple recrystallization when DMF or DMSO of higher dielectric constant was used as a co-solvent in diazotization of O-benzyl-L-tyrosine. It was easily turned into various optically pure (S)-3-p-hydroxyphenyllactic acid derivatives.
https://doi.org/10.1007/s00726-006-0451-6