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

Description

Pelubiprofen is a non-steroidal anti-inflammatory drug (NSAID) that belongs to the propionic acid class. It is known for its potent analgesic and anti-inflammatory properties, which are achieved by inhibiting the production of prostaglandins, hormone-like substances that contribute to the body's inflammatory response. This makes Pelubiprofen a valuable option for managing various painful conditions with a relatively low risk of side effects.

Uses

Used in Pharmaceutical Industry:
Pelubiprofen is used as an analgesic and anti-inflammatory agent for the treatment of conditions such as arthritis, muscle pain, and other inflammatory disorders. Its effectiveness in reducing pain and inflammation, coupled with its relatively low risk of side effects, makes it a preferred choice for managing these conditions.
Used in Pain Management:
Pelubiprofen is used as a pain reliever to alleviate discomfort associated with various conditions, including but not limited to, arthritis, muscle strains, and other inflammatory disorders. Its ability to reduce inflammation and pain without causing significant side effects makes it a popular choice for pain management.
Used in Inflammatory Disorder Treatment:
Pelubiprofen is used as an anti-inflammatory medication to treat a range of inflammatory disorders. By inhibiting the production of prostaglandins, it helps to control the inflammatory response and provide relief from the symptoms associated with these 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

• 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 
• 133963-62-9 (-)-(2R)-2-<4-(2-Oxocyclohexylidenemethyl)phenyl>propionic acid 
• 133908-75-5 (+)-(2S)-2-<4-(2-Oxocyclohexylidenemethyl)phenyl>propionic acid 

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.