3-{4-[2-(2-methylphenyl)ethynyl]phenyl}propanoic acid

• ChemBase ID: 154377
• Molecular Formular: C18H16O2
• Molecular Mass: 264.31844
• Monoisotopic Mass: 264.11502975
• SMILES: Cc1ccccc1C#Cc1ccc(cc1)CCC(=O)O
• Canonical SMILES: OC(=O)CCc1ccc(cc1)C#Cc1ccccc1C
• InChI: InChI=1S/C18H16O2/c1-14-4-2-3-5-17(14)12-10-15-6-8-16(9-7-15)11-13-18(19)20/h2-9H,11,13H2,1H3,(H,19,20)
• InChIKey: FODHWOBAQBTTFS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{4-[2-(2-methylphenyl)ethynyl]phenyl}propanoic acid
• IUPAC Traditional name: 3-{4-[2-(2-methylphenyl)ethynyl]phenyl}propanoic acid
• Synonyms: 3-(4-(o-Tolylethynyl)phenyl)propanoic acid; TUG-424

Database IDs

• CAS Number: 1082058-99-8
• MDL Number: MFCD12912449
• PubChem SID: 162248516
• PubChem CID: 25150014

CALCULATED PROPERTIES

• Acid pKa: 3.9124851
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.09639
• LogD (pH = 7.4): 1.4829574
• Log P: 4.6900535
• Molar Refractivity: 74.8444 cm^3
• Polarizability: 30.29906 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL; H2O: insoluble

Safety Information

• European Hazard Symbols: Nature polluting (N); Irritant (Xi)
• UN Number: 3077
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 36-50/53
• Safety Statements: 26-60-61
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H319-H410
• GHS Precautionary statements: P273-P305 + P351 + P338-P501
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• RID/ADR: UN 3077 9/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C18H16O2

DETAILS

Sigma Aldrich - T6829

Biochem/physiol Actions
TUG-424 is expected to be useful in the exploration of FFA1 and may also be valuable as a lead structure for new potential antidiabetic therapeutics. TUG-424 significantly increased glucose-stimulated insulin secretion at 100 nM and may serve to explore the role of FFA1 in metabolic diseases such as diabetes or obesity. It enhanced glucose-stimulated insulin secretion in a rat beta-cell line already at 100 nM and from isolated mouse islets through FFA1.GPR40 (now FFA1) was formerly an orphan GPCR whose endogenous ligands have recently been identified as free fatty acids (FFAs). The receptor appears to be involved in the pathophysiology of type 2 diabetes and is a drug target because of its role in FFA-mediated enhancement of glucose-stimulated insulin release.