87226-41-3

Basic information

• Product Name: RAK 593
• Synonyms: (-)-(R)-Etodolac;Pyrano[3,4-b]indole-1-acetic acid, 1,8-diethyl-1,3,4,9-tetrahydro-, (1R)-;Pyrano[3,4-b]indole-1-acetic acid, 1,8-diethyl-1,3,4,9-tetrahydro-, (R)-;RAK 593;R-Etodolac;SDX 101
• CAS NO: 87226-41-3
• Molecular Formula: C₁₇H₂₁NO₃
• Molecular Weight: 287.35
• Product Categories: Chiral Reagents;Heterocycles;Indole Derivatives;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 87226-41-3.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 452.6°C at 760 mmHg
• Flash Point: 227.5°C
• Appearance: /
• Density: 1.165g/cm³
• Vapor Pressure: 2.22E-08mmHg at 25°C
• Refractive Index: 1.581
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Sparingly), DMSO (Slightly) Methanol (Slightly)
• CAS DataBase Reference: RAK 593(CAS DataBase Reference)
• NIST Chemistry Reference: RAK 593(87226-41-3)
• EPA Substance Registry System: RAK 593(87226-41-3)

Safety Data

• Hazardous Substances Data: 87226-41-3(Hazardous Substances Data)

Usage

Uses

The R-enantiomer of Etodolac (E933090). Anti-inflammatory; analgesic.

InChI:InChI=1/C17H21NO3/c1-3-11-6-5-7-12-13-8-9-21-14(10-15(19)20-4-2)17(13)18-16(11)12/h5-7,14,18H,3-4,8-10H2,1-2H3/t14-/m1/s1

Upstream product

• 41340-25-4 etodolac 
• 87249-11-4 (S)-etodolac 
• 2627-86-3 (S)-1-phenyl-ethylamine 

Downstream Products

• 41340-25-4 etodolac 

Relevant articles and documents

Resolution of Etodolac and Antiinflammatory and Prostaglandin Synthetase Inhibiting Properties of the Enantiomers

Etodolac, 1,8-diethyl-1,3,4,9-tetrahydropyranoindole-1-acetic acid, a clinically effective analgesic and antiinflammatory agent, has been resolved via a chromatographic separation of its diastereoisomeric esters with (-)-borneol.The effects of the enantiomers were studied in vitro on prostaglandin synthetase and on adjuvant-induced arthritis in rats.The biochemical and pharmacological results show that virtually all of the effects of etodolac are due to the (+) enantiomer.

Evaluation of the Edman degradation product of vancomycin bonded to core-shell particles as a new HPLC chiral stationary phase

A modified macrocyclic glycopeptide-based chiral stationary phase (CSP), prepared via Edman degradation of vancomycin, was evaluated as a chiral selector for the first time. Its applicability was compared with other macrocyclic glycopeptide-based CSPs: TeicoShell and VancoShell. In addition, another modified macrocyclic glycopeptide-based CSP, NicoShell, was further examined. Initial evaluation was focused on the complementary behavior with these glycopeptides. A screening procedure was used based on previous work for the enantiomeric separation of 50 chiral compounds including amino acids, pesticides, stimulants, and a variety of pharmaceuticals. Fast and efficient chiral separations resulted by using superficially porous (core-shell) particle supports. Overall, the vancomycin Edman degradation product (EDP) resembled TeicoShell with high enantioselectivity for acidic compounds in the polar ionic mode. The simultaneous enantiomeric separation of 5 racemic profens using liquid chromatography-mass spectrometry with EDP was performed in approximately 3?minutes. Other highlights include simultaneous liquid chromatography separations of rac-amphetamine and rac-methamphetamine with VancoShell, rac-pseudoephedrine and rac-ephedrine with NicoShell, and rac-dichlorprop and rac-haloxyfop with TeicoShell.

Synthesis of diastereomeric anhydrides of (RS)-ketorolac and (RS)-etodolac, semi-preparative HPLC enantioseparation, establishment of molecular asymmetry and recovery of pure enantiomers

Herein, enantioseparation of two anti-inflammatory drugs, namely, (RS)-ketorolac and (RS)-etodolac, commonly marketed and administered as racemates, was achieved by RP-HPLC. This method provided very low limit of detection values (3.69 and 3.02 ng mL-1 for diastereomeric derivatives of (R)- and (S)-Ket, respectively) as compared to those reported in literature. (S)-Naproxen benzotriazole ester, which was used as a chiral reagent, was synthesized and characterized by UV, IR, and 1H NMR spectroscopies, elemental analysis, and polarimetry. The diastereomeric derivatives were synthesized via microwave irradiation, separated on an analytical scale by RP-HPLC, and then isolated by preparative HPLC. The use of a mobile phase containing methanol and aqueous triethylamine phosphate (TEAP) in the isocratic mode was found to be successful for the separation of diastereomeric derivatives, and the separation conditions with respect to pH, flow rate, and buffer concentration were optimized. The diastereomeric derivatives were characterized, and their absolute configuration was established. Hydrolysis of the derivatives provided native enantiomers under mild reaction conditions. This study describes the successful enantioseparation of the above mentioned two analytes by semi-preparative HPLC with easy recovery of the native enantiomers without racemization and with the establishment of molecular asymmetry.

Direct racemization of indole derivatives

The present invention discloses processes for the racemization of enantiomers of etodolac and other tetra-hydropyrano indole derivatives.