4-(4-octylphenyl)benzoic acid

• ChemBase ID: 153144
• Molecular Formular: C21H26O2
• Molecular Mass: 310.42994
• Monoisotopic Mass: 310.19328007
• SMILES: CCCCCCCCc1ccc(cc1)c1ccc(cc1)C(=O)O
• Canonical SMILES: CCCCCCCCc1ccc(cc1)c1ccc(cc1)C(=O)O
• InChI: InChI=1S/C21H26O2/c1-2-3-4-5-6-7-8-17-9-11-18(12-10-17)19-13-15-20(16-14-19)21(22)23/h9-16H,2-8H2,1H3,(H,22,23)
• InChIKey: HXBKPYIEQLLNBK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(4-octylphenyl)benzoic acid
• IUPAC Traditional name: 4-(4-octylphenyl)benzoic acid
• Synonyms: 4′-Octyl-4-biphenylcarboxylic acid, 4′-n-octylbiphenyl-4-carboxylic acid; 8BCA; AC-55649

Database IDs

• CAS Number: 59662-49-6
• MDL Number: MFCD00157040
• PubChem SID: 162247284; 24724405
• PubChem CID: 1714884

CALCULATED PROPERTIES

• Acid pKa: 4.0761123
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 5.4668975
• LogD (pH = 7.4): 3.789655
• Log P: 6.903456
• Molar Refractivity: 95.6986 cm^3
• Polarizability: 38.33508 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >7 mg/mL
• Apperance: solid

Safety Information

• German water hazard class: 3
• GHS Hazard statements: H413
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... RARB(5915)

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C21H26O2

DETAILS

Sigma Aldrich - A9480

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.