59662-49-6

Basic information

• Product Name: 4'-N-OCTYLBIPHENYL-4-CARBOXYLIC ACID
• Synonyms: RARECHEM AL BO 1323;4'-N-OCTYLBIPHENYL-4-CARBOXYLIC ACID;4-N-OCTYLBIPHENYL-4'-CARBOXYLIC ACID;4'-OCTYL-[1,1'-BIPHENYL]-4-CARBOXYLIC ACID;4'-OCTYL-4-BIPHENYLCARBOXYLIC ACID;4-OCTYL-4'-BIPHENYLCARBOXYLIC ACID;8BCA;AC 55649
• CAS NO: 59662-49-6
• Molecular Formula: C₂₁H₂₆O₂
• Molecular Weight: 310.43
• Product Categories: Biphenyl & Diphenyl ether
• Mol File: 59662-49-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 148-152 °C(Solv: dichloromethane (75-09-2))
• Boiling Point: 462 °C at 760 mmHg
• Flash Point: 216.9 °C
• Appearance: /
• Density: 1.037 g/cm³
• Storage Temp.: Store at +4°C
• Solubility: DMSO: >7mg/mL
• PKA: 4.23±0.10(Predicted)
• CAS DataBase Reference: 4'-N-OCTYLBIPHENYL-4-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-N-OCTYLBIPHENYL-4-CARBOXYLIC ACID(59662-49-6)
• EPA Substance Registry System: 4'-N-OCTYLBIPHENYL-4-CARBOXYLIC ACID(59662-49-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 59662-49-6(Hazardous Substances Data)

Usage

Uses

AC 55649 is a potent and selective RARβ2 receptor agonist (1). RARβ2 receptor agonists are potential drug candidates for developing treatment for type 2 diabetes and hepatic steatosis (2).

Biological Activity

Potent, isoform-selective RAR β 2 receptor agonist (pEC 50 values are 6.9, 5.7 and 5.6 at RAR β 2, RAR β 1 and RAR α respectively) that displays 100-fold selectivity versus other retinoid receptors. Inhibits proliferation of the breast cancer cell line MCF-7.

Biochem/physiol Actions

AC-55649 is a subtype selective RAR (RARβ2) agonist. AC-55649 is a potent, orally available isoform selective Retinoic Acid Receptor β2. AC-55649 has high selectivity, 99% for RARβ2 and 31% for RARβ1. When compared to the gold standard AM-580 (Cat. No A8843), both isoform receptors were 100%. AC-55649 has a potent EC50 of 6.9 μM compared to an EC50 of 7.7 μM for AM-580.

Upstream product

• 52709-84-9 4-octyl-4'-cyanobiphenyl 
• 14047-29-1 4-carboxyphenylboronic acid 
• 252011-38-4 1-hexyl-2-(4-bromophenyl)acetylene 

Downstream Products

• 920270-45-7 3-(4'-octyl-biphenyl-4-yl)-3-oxo-2-(triphenyl-λ5-phosphanylidene)-propionitrile 

Relevant articles and documents

Improvement in Aqueous Solubility of Retinoic Acid Receptor (RAR) Agonists by Bending the Molecular Structure

Aqueous solubility is a key requirement for many functional molecules, e. g., drug candidates. Decrease of the partition coefficient (log P) by chemical modification, i.e., introduction of hydrophilic group(s) into molecules, is a classical strategy for improving aqueous solubility. We have been investigating alternative strategies for improving the aqueous solubility of pharmaceutical compounds by disrupting intermolecular interactions. Here, we show that introducing a bend into the molecular structure of retinoic acid receptor (RAR) agonists by changing the substitution pattern from para to meta or ortho dramatically enhances aqueous solubility by up to 890-fold. We found that meta analogs exhibit similar hydrophobicity to the parent para compound, and have lower melting points, supporting the idea that the increase of aqueous solubility was due to decreased intermolecular interactions in the solid state as a result of the structural changes.

COMPOUNDS WITH ACTIVITY AT RETINOIC ACID RECEPTORS

Disclosed herein are novel compounds with activity at RARβ 2 receptors. Further disclosed are the use of such compounds for treatment of or to alleviate symptoms of cancer, neurological disorders such as memory deficits and schizophrenia, neurodegenerative disorders such as Parkinson's and Alzheimer's diseases, inflammatory disorders such as psoriasis and rheumatoid arthritis, eye disorders and depression.