4-[2-(2-methylphenyl)ethynyl]-benzenepropanoicacid Chemical Properties

Boiling point:

448.1±38.0 °C(Predicted)

Density 

1.17±0.1 g/cm3(Predicted)

storage temp. 

Store at +4°C

solubility 

DMSO: >10mg/mL

pka

4.62±0.10(Predicted)

form 

A crystalline solid

color 

White to off-white

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

SMILES

Cc1ccccc1C#Cc2ccc(CCC(O)=O)cc2

Safety Information

Hazard Codes 

Xi,N

Risk Statements 

36-50/53

Safety Statements 

26-60-61

RIDADR 

UN 3077 9 / PGIII

WGK Germany 

3

Storage Class

11 - Combustible Solids

Hazard Classifications

Aquatic Acute 1
Aquatic Chronic 1
Eye Irrit. 2

4-[2-(2-methylphenyl)ethynyl]-benzenepropanoicacid Usage And Synthesis

Uses

TUG-424 is a potent and selective free fatty acid receptor 1 (FFA1/GPR40) agonist with an EC50 of 32 nM. TUG-424 significantly increases glucose-stimulated insulin secretion at 100 nM. TUG-424 may serve to explore the role of FFA1 in metabolic diseases such as diabetes or obesity[1]. TUG-424 is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.

Biological Activity

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 r at 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.

References

[1] Discovery of Potent and Selective Agonists for the Free Fatty Acid Receptor 1 (FFA1/GPR40), a Potential Target for the Treatment of Type II Diabetes J. Med. Chem., 2008, 51 (22), pp 7061-7064
[2] Christiansen E, et al. Discovery of potent and selective agonists for the free fatty acid receptor 1 (FFA(1)/GPR40), a potential target for the treatment of type II diabetes. J Med Chem. 2008 Nov 27;51(22):7061-4. DOI:10.1021/jm8010178

4-[2-(2-methylphenyl)ethynyl]-benzenepropanoicacid(1082058-99-8)Related Product Information

• TUG 891
• TUG-770
• TUG-469