222555-06-8

Basic information

• Product Name: (S)-2-ETHOXY-3-(4-HYDROXY-PHENYL)-PROPIONIC ACID ETHYL ESTER
• Synonyms: Ethyl (S)-2-Ethoxy-3-(4-hydroxyphenyl)propionate;Benzenepropanoic acid, .alpha.-ethoxy-4-hydroxy-, ethyl ester, (.alpha.S)-;(S)-Ethyl 2-ethoxy-3-(4-hydroxyphenyl)propanoate
• CAS NO: 222555-06-8
• Molecular Formula: C₁₃H₁₈O₄
• Molecular Weight: 238.28
• Mol File: 222555-06-8.mol

Chemical Properties

• Boiling Point: 367.296 °C at 760 mmHg
• Flash Point: 134.932 °C
• Appearance: /
• Density: 1.116g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.515
• Storage Temp.: 2-8°C
• PKA: 9.75±0.15(Predicted)
• CAS DataBase Reference: (S)-2-ETHOXY-3-(4-HYDROXY-PHENYL)-PROPIONIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-ETHOXY-3-(4-HYDROXY-PHENYL)-PROPIONIC ACID ETHYL ESTER(222555-06-8)
• EPA Substance Registry System: (S)-2-ETHOXY-3-(4-HYDROXY-PHENYL)-PROPIONIC ACID ETHYL ESTER(222555-06-8)

Safety Data

• Hazardous Substances Data: 222555-06-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl (S)-2-Ethoxy-3-(4-hydroxyphenyl)propionate is used as an intermediate in the synthesis of glitazars for their potent antidiabetic and lipid-lowering properties. These glitazars, as PPARα/γ dual agonists, help regulate glucose and lipid metabolism, providing an effective treatment option for patients with diabetes and dyslipidemia.
Used in Drug Development:
(S)-2-ETHOXY-3-(4-HYDROXY-PHENYL)-PROPIONIC ACID ETHYL ESTER is utilized in the development of novel pharmaceuticals targeting metabolic disorders. Its role in the synthesis of glitazars allows for the creation of drugs that can potentially improve the management of diabetes and related conditions, offering a promising avenue for researchers and pharmaceutical companies in the development of innovative treatments.

InChI:InChI=1/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

Upstream product

• 481072-39-3 3-(4-benzyloxy-phenyl)-2-(tert-butyl-dimethyl-silanyloxy)-propionic acid ethyl ester 
• 251454-49-6 (2S)-3-[4-(benzyloxy)phenyl]-2-ethoxypropanoic acid 
• 64-17-5 ethanol 
• 251454-50-9 ethyl (2S)-3-[4-(benzyloxy)phenyl]-2-ethoxypropanoate 
• 64-67-5 diethyl sulfate 
• 162919-37-1 (S)-3-[4-(benzyloxy)phenyl]-2-hydroxypropanoic acid 
• 222835-03-2 3-(4-benzyloxy-phenyl)-2-ethoxy-acrylic acid ethyl ester 
• 197299-16-4 ethyl 2-ethoxy-3-(4-hydroxy-phenyl)-propionate 
• 123-08-0 4-hydroxy-benzaldehyde 
• 441351-28-6 (4-(bromomethyl)phenoxy)(tert-butyl)diphenylsilane 
• 116748-06-2 (4-(hydroxymethyl)phenoxy)(tert-butyl)diphenylsilane 
• 116748-05-1 4-(tert-butyldiphenylsilyloxy)benzaldehyde 
• 4397-53-9 p-benzyloxybenzaldehyde 
• 17640-26-5 Ethoxyessigsaeure-methylester 

Downstream Products

• 303110-67-0 (2S)-3-[4-(3,3-Di-p-tolyl-allyloxy)-phenyl]-2-ethoxy-propionic acid ethyl ester 
• 477546-90-0 4-((S)-2-(ethoxycarbonyl)-2-ethoxyethyl)phenyl trifluoromethanesulfonate 
• 1056456-28-0 (S)-2-ethoxy-3-(4-((3-methylthiophen-2-yl)methoxy)phenyl)propionic acid ethyl ester 
• 1055303-89-3 (S)-2-ethoxy-3-(4-hydroxy-phenyl)-propionic acid benzyl ester 
• 1055303-33-7 (S)-2-ethoxy-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-acetoxy]-phenyl}-propionic acid 
• 1055303-91-7 (S)-2-ethoxy-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-acetoxy]-phenyl}-propionic acid benzyl ester 
• 1055303-90-6 (S)-3-{4-[2-(4-tert-butoxycarbonylamino-phenyl)-acetoxy]-phenyl}-2-ethoxy-propionic acid benzyl ester 
• 1056456-04-2 (S)-3-(4-((5-bromo-3-methylthiophen-2-yl)methoxy)phenyl)-2-ethoxypropionic acid ethyl ester 
• 1056455-43-6 (S)-2-ethoxy-3-(4-((5-(3-methoxyphenyl)-3-methylthiophen-2-yl)methoxy)phenyl)propionic acid 
• 1056456-02-0 (S)-2-ethoxy-3-(4-((5-(3-methoxyphenyl)-3-methylthiophen-2-yl)methoxy)phenyl)propionic acid ethyl ester 
• 516518-18-6 (E)(E)(S)(S) 2-ethoxy-3-{4-[5-(3-{5-[4-(2-ethoxy-2-ethoxycarbonyl-ethyl)-phenoxy]-3-methyl-pent-3-en-1-ynyl}-phenyl)-3-methyl-pent-2-en-4-ynyloxy]-phenyl}-propionic acid ethyl ester 
• 516518-10-8 (E)(E)(S)(S) 2-Ethoxy-3-{4-[5-(4-{5-[4-(2-ethoxy-2-ethoxycarbonylethyl)-phenoxy]-3-methyl-pent-3-en-1-ynyl}-phenyl)-3-methyl-pent-2-en-4-ynyloxy]-phenyl}-propionic acid ethyl ester 
• 516518-03-9 (E)(E)(S)(S) 2-Ethoxy-3-{4-[5-(4'-{5-[4-(2-ethoxy-2-ethoxycarbonylethyl)-phenoxy]-3-methyl-pent-3-en-1-ynyl}-biphenyl-4-yl)-3-methyl-pent-2-en-4-ynyloxy]-phenyl}-propionic acid ethyl ester 
• 516517-25-2 (E)(E)(S)(S) 2-ethoxy-3-{4-[5-(4-{5-[4-(2-ethoxy-2-ethoxycarbonyl-ethyl)-phenoxy]-pent-3-en-1-ynyl}-phenyl)-pent-2-en-4-ynyloxy]-phenyl}-propionic acid ethyl ester 

Relevant articles and documents

COMPOSITION COMPRISING HIGH PURITY PYRROLE DERIVATIVE AND METHOD FOR PREPARATION THEREOF

The present invention relates to a composition comprising high purity pyrrole derivative and method for preparation thereof. The present invention particularly relates to compositions comprising Saroglitazar magnesium having purity of 99.0% or more, and one or more of an aldehyde compound of Formula (II), diketo oxirane compound of Formula (III), hydroxy methyl compound of Formula (IV) or dimer compound of Formula (V), relative to saroglitazar magnesium, each present in an amount of about 0.15% or less, respectively, by weight, when measured by area percentage of HPLC.

A highly efficient and enantioselective synthesis of EEHP and EMHP: intermediates of PPAR agonists

Glycolate alkylation reactions of (S)-4-isopropyl-1-[(R)-1-phenylethyl]imidazolidin-2-one auxiliary has been optimised with high yields and diastereoselectivity on substituted benzyl and allyl bromides. The standardised reaction condition was employed for the stereoselective synthesis of EEHP and EMHP intermediates of PPAR agonists.

PPAR-SPARING COMPOUNDS FOR THE TREATMENT OF METABOLIC DISEASES

The present invention relates to hydroxamate compounds and pharmaceutical compositions that are useful for treating and/or preventing metabolic inflammation mediated diseases such as diabetes, obesity, hypertension, dyslipidemia, a neurodegenerative disorder (e.g., Alzheimer's disease, Parkinson's disease, or Huntington's disease), or any combination thereof. Moreover, the present invention also provides methods of treatment for these diseases or disorders.

Efficient Synthesis of Differentiated syn-1,2-Diol Derivatives by Asymmetric Transfer Hydrogenation-Dynamic Kinetic Resolution of α-Alkoxy-Substituted β-Ketoesters

Asymmetric transfer hydrogenation was applied to a wide range of racemic aryl α-alkoxy-β-ketoesters in the presence of well-defined, commercially available, chiral catalyst RuII-(N-p-toluenesulfonyl-1,2-diphenylethylenediamine) and a 5:2 mixture of formic acid and triethylamine as the hydrogen source. Under these conditions, dynamic kinetic resolution was efficiently promoted to provide the corresponding syn α-alkoxy-β-hydroxyesters derived from substituted aromatic and heteroaromatic aldehydes with a high level of diastereoselectivity (diastereomeric ratio (d.r.)>99:1) and an almost perfect enantioselectivity (enantiomeric excess (ee)>99>). Additionally, after extensive screening of the reaction conditions, the use of RuII- and RhIII-tethered precatalysts extended this process to more-challenging substrates that bore alkenyl-, alkynyl-, and alkyl substituents to provide the corresponding syn α-alkoxy-β-hydroxyesters with excellent enantiocontrol (up to 99‰ee) and good to perfect diastereocontrol (d.r.>99:1). Lastly, the synthetic utility of the present protocol was demonstrated by application to the asymmetric synthesis of chiral ester ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)-propanoate, which is an important pharmacophore in a number of peroxisome proliferator-activated receptor α/γ dual agonist advanced drug candidates used for the treatment of type-II diabetes. RuII-catalyzed asymmetric transfer hydrogenation with dynamic kinetic resolution was successfully applied to a wide variety of racemic α-alkoxy-β-ketoesters derived from substituted aromatic and heteroaromatic benzaldehydes and cinnamaldehydes (see scheme; PMB=p-methoxybenzyl, S/C=substrate/catalyst ratio).

PPAR-SPARING THIAZOLIDINEDIONES AND COMBINATIONS FOR THE TREATMENT OF NEURODEGENERATIVE DISEASES

The present invention relates to PPARy- sparing compounds and pharmaceutical compositions formulated with such compounds that are useful for treating, delaying the onset of, or reducing the symptoms of a neurodegenerative disorder including Huntington's disease, epilepsy, AMS, and MS.

A PROCESS FOR PREPARATION OF PYRROLES HAVING HYPOLIPIDEMIC HYPOCHOLESTEREMIC ACTIVITIES

The present invention provides pyrroles having hypolipidemic hypocholesteremic activities. The invention provides saroglitazar and its pharmaceutically acceptable salts, hydrates, solvates, polymorphs or intermediates thereof. The invention also provides a process for the preparation of saroglitazar. The invention further provides intermediates as well process for preparation thereof.

A new enantioselective synthesis of (S)-2-ethoxy-3-(4-hydroxyphenyl) propanoic acid esters (EEHP and IEHP), useful pharmaceutical intermediates of PPAR agonists

A new enantioselective synthetic route to the title compounds has been developed in a simple and practical way with high enantiopurity using commercially available starting material.

A PROCESS FOR THE PREPARATION OF 3-ARYL-2-HYDROXY PROPANOIC ACID COMPOUNDS

The present disclosure provides a process for synthesis of 3-aryl-2-hydroxy propanoic acid derivatives of formula (S)-1. wherein R1 represents H or (C1-C5) alkyl groups and R2 represents (C1-C5) alkyl groups.

PPAR-SPARING COMPOUNDS FOR USE IN THE TREATMENT OF DIABETES AND OTHER METABOLIC DISEASES

The present invention relates to compounds and pharmaceutical compositions that are useful for treating and/or preventing diabetes or other metabolic diseases, optionally in combination with a second therapy such an active pharmaceutical agent or diet restriction or an increase in duration or exertion in physical activity.

NOVEL PHENYLPROPIONIC ACID DERIVATIVES AS PEROXISOME PROLIFERATOR-ACTIVATED GAMMA RECEPTOR MODULATORS, METHOD OF THE SAME, AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME

The present invention provides a novel phenylpropionic acid derivative and a PPAR-γ modulator comprising the same as an active ingredient. The phenylpropionic acid derivative of the present invention has modulatory action on function of PPAR-γ and then exhibits hypoglycemic, hypolipidemic and insulin resistance-reducing effects on PPAR-mediated diseases or disorders. Therefore, the present invention is prophylactically or therapeutically effective for diabetes and metabolic diseases.