5-(tetradecyloxy)furan-2-carboxylic acid

• ChemBase ID: 153681
• Molecular Formular: C19H32O4
• Molecular Mass: 324.45498
• Monoisotopic Mass: 324.2300595
• SMILES: CCCCCCCCCCCCCCOc1ccc(o1)C(=O)O
• Canonical SMILES: CCCCCCCCCCCCCCOc1ccc(o1)C(=O)O
• InChI: InChI=1S/C19H32O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-16-22-18-15-14-17(23-18)19(20)21/h14-15H,2-13,16H2,1H3,(H,20,21)
• InChIKey: CZRCFAOMWRAFIC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(tetradecyloxy)furan-2-carboxylic acid
• IUPAC Traditional name: 5-(tetradecyloxy)furan-2-carboxylic acid
• Synonyms: 5-(Tetradecyloxy)-2-furoic acid; TOFA

Database IDs

• CAS Number: 54857-86-2
• MDL Number: MFCD01726059
• PubChem SID: 162247820
• PubChem CID: 115175

CALCULATED PROPERTIES

• Acid pKa: 3.1461303
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.0645523
• LogD (pH = 7.4): 2.9378335
• Log P: 6.3922806
• Molar Refractivity: 91.3052 cm^3
• Polarizability: 35.989334 Å^3
• Polar Surface Area: 59.67 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >2 mg/mL; H2O: insoluble
• Apperance: tan solid
• Melting Point: 112-115 °C

Safety Information

• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C19H32O4

DETAILS

Sigma Aldrich - T6575

Biochem/physiol Actions
A cell-permeable, potent, reversible, and competitive inhibitor of acetyl-CoA carboxylase (ACC). Key enzyme involved in fatty acid biosynthesis. Inhibits cellular fatty acid synthesis in a dose-dependent manner (IC50 = 4 mM in human breast cancer cell line MCF7).