69956-77-0

Basic information

• Product Name: Pelubiprofen
• Synonyms: Pelubiprofen;2-(4-((2-oxocyclohexylidene)methyl)phenyl)propionic acid;RS-2131;α-Methyl-4-[((E)-2-oxocyclohexylidene)methyl]benzeneacetic acid;α-Methyl-4-[((E)-2-oxocyclohexylidene)methyl]phenylacetic acid;2-[4-[(E)-(2-oxocyclohexylidene)methyl]phenyl]propanoic acid;AUZUGWXLBGZUPP-GXDHUFHOSA-N
• CAS NO: 69956-77-0
• Molecular Formula: C₁₆H₁₈O₃
• Molecular Weight: 258.315
• Mol File: 69956-77-0.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 457.4°C at 760 mmHg
• Flash Point: 244.5°C
• Appearance: /
• Density: 1.199g/cm³
• Vapor Pressure: 3.7E-09mmHg at 25°C
• Refractive Index: 1.604
• PKA: 4.27±0.10(Predicted)
• CAS DataBase Reference: Pelubiprofen(CAS DataBase Reference)
• NIST Chemistry Reference: Pelubiprofen(69956-77-0)
• EPA Substance Registry System: Pelubiprofen(69956-77-0)

Safety Data

• Hazardous Substances Data: 69956-77-0(Hazardous Substances Data)

Usage

General Description

Pelubiprofen is a non-steroidal anti-inflammatory drug (NSAID) that is used to alleviate pain and reduce inflammation. It belongs to the propionic acid class of NSAIDs and has been shown to have potent analgesic and anti-inflammatory properties. Pelubiprofen works by inhibiting the production of prostaglandins, which are hormone-like substances that play a key role in the body's inflammatory response. It is commonly used to treat conditions such as arthritis, muscle pain, and other inflammatory disorders. Pelubiprofen has been shown to be effective in reducing pain and inflammation with a relatively low risk of side effects, making it a valuable option for managing various painful conditions.

InChI:InChI=1/C16H18O3/c1-11(16(18)19)13-8-6-12(7-9-13)10-14-4-2-3-5-15(14)17/h6-11H,2-5H2,1H3,(H,18,19)/b14-10+

Synthetic route

4-cyclohexen-1-ylmorpholine (670-80-4) + ethyl 2-(4-formylphenyl)propionate (43153-04-4) → 2-[4-(2-oxo-1-cyclohexyliden methyl)-phenyl]propionic acid (69956-77-0)

Conditions	Yield
With hydrogenchloride; potassium carbonate Yield given. Multistep reaction;

(S)-1-phenyl-ethylamine (2627-86-3) + 2-[4-(2-oxo-1-cyclohexyliden methyl)-phenyl]propionic acid (69956-77-0) → (-)-N-<(1S)-1-Phenylethyl>-(2S)-<4-(2-oxocyclohexylidenemethyl)phenyl>propionamide (133883-81-5, 133883-82-6) + (-)-N-<(1S)-1-Phenylmethyl>-(2R)-<4-(2-oxocyclohexylidenemethyl)phenyl>propionamide (133883-81-5, 133883-82-6)

Conditions	Yield
With 2,2'-dipyridyldisulphide; triphenylphosphine In dichloromethane at 0℃; for 0.5h;	A 0.75 g B 0.8 g

2-[4-(2-oxo-1-cyclohexyliden methyl)-phenyl]propionic acid (69956-77-0) → (+)-(2S)-2-<4-(2-Oxocyclohexylidenemethyl)phenyl>propionic acid (133908-75-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 0.75 g / 2,2'-dipyridyl disulfide, triphenylphosphine / CH2Cl2 / 0.5 h / 0 °C 2: 1.) N2O4, sodium acetate / 1.) CCl4, 0 deg C, 2 h, 2.) CCl4, reflux, 1 h View Scheme

2-[4-(2-oxo-1-cyclohexyliden methyl)-phenyl]propionic acid (69956-77-0) → (-)-(2R)-2-<4-(2-Oxocyclohexylidenemethyl)phenyl>propionic acid (133963-62-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 0.8 g / 2,2'-dipyridyl disulfide, triphenylphosphine / CH2Cl2 / 0.5 h / 0 °C 2: 1.) N2O4, sodium acetate / 1.) CCl4, 0 deg C, 2 h, 2.) CCl4, reflux, 1 h View Scheme

Upstream product

• 670-80-4 4-cyclohexen-1-ylmorpholine 
• 43153-04-4 ethyl 2-(4-formylphenyl)propionate 

Downstream Products

• 133963-62-9 (-)-(2R)-2-<4-(2-Oxocyclohexylidenemethyl)phenyl>propionic acid 
• 133908-75-5 (+)-(2S)-2-<4-(2-Oxocyclohexylidenemethyl)phenyl>propionic acid 
• 133883-81-5 (-)-N-<(1S)-1-Phenylethyl>-(2S)-<4-(2-oxocyclohexylidenemethyl)phenyl>propionamide 
• 133883-81-5 (-)-N-<(1S)-1-Phenylmethyl>-(2R)-<4-(2-oxocyclohexylidenemethyl)phenyl>propionamide 

Relevant articles and documents

Synthesis and Antiinflammatory Activity of acetic Acids and Related Compounds

acetic acid derivatives and related compounds were synthesized to test their antiinflammatory and analgesic activities.Some of the compounds in this series were found to have good activity in the carrageenan edema test.Among them, sodium 2-phenyl>propionate dihydrate (15) and 2-phenyl>propionic acid (13b) showed potent analgesic and antiadjuvant arthritis activities with excellent antipyretic properties.