122674-96-8

Basic information

• Product Name: Propanoic acid, 2-(2,4-dichlorophenoxy)-, methyl ester, (R)-
• CAS NO: 122674-96-8
• Molecular Formula: C10H10Cl2O3
• Molecular Weight: 249.094
• Mol File: 122674-96-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Propanoic acid, 2-(2,4-dichlorophenoxy)-, methyl ester, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Propanoic acid, 2-(2,4-dichlorophenoxy)-, methyl ester, (R)-(122674-96-8)
• EPA Substance Registry System: Propanoic acid, 2-(2,4-dichlorophenoxy)-, methyl ester, (R)-(122674-96-8)

Safety Data

• Hazardous Substances Data: 122674-96-8(Hazardous Substances Data)

Upstream product

• 27871-49-4 (S)-Methyl lactate 
• 120-83-2 2,4-dichlorophenol 
• 23844-57-7 2-(2,4-dichlorophenoxy)propanoic acid methyl ester 
• 186581-53-3 diazomethane 
• 120-36-5 (R)-dichlorprop 

Downstream Products

• 120-36-5 (R)-dichlorprop 

Relevant articles and documents

Structural insights into the differences among lactisole derivatives in inhibitory mechanisms against the human sweet taste receptor

Lactisole, an inhibitor of the human sweet taste receptor, has a 2-phenoxypropionic acid skeleton and has been shown to interact with the transmembrane domain of the T1R3 subunit (T1R3-TMD) of the receptor. Another inhibitor, 2,4-DP, which shares the same molecular skeleton as lactisole, was confirmed to be approximately 10-fold more potent in its inhibitory activity than lactisole; however the structural basis of their inhibitory mechanisms against the receptor remains to be elucidated. Crystal structures of the TMD of metabotropic glutamate receptors, which along with T1Rs are categorized as class C G-protein coupled receptors, have recently been reported and made it possible to create an accurate structural model for T1R3-TMD. In this study, the detailed structural mechanism underlying sweet taste inhibition was characterized by comparing the action of lactisole on T1R3-TMD with that of 2,4-DP. We first performed a series of experiments using cultured cells expressing the sweet taste receptor with mutations and examined the interactions with these inhibitors. Based on the results, we next performed docking simulations and then applied molecular dynamics-based energy minimization. Our analyses clearly revealed that the (S)-isomers of both lactisole and 2,4-DP, interacted with the same seven residues in T1R3-TMD and that the inhibitory potencies of those inhibitors were mainly due to stabilizing interactions mediated via their carboxyl groups in the vertical dimension of the ligand pocket of T1R3-TMD. In addition, 2,4-DP engaged in a hydrophobic interaction mediated by its o-Cl group, and this interaction may be chiefly responsible for the higher inhibitory potency of 2,4-DP.

Enantioselective inhibition: a strategy for improving the enantioselectivity of biocatalytic systems

Dextromethorphan (DM) and levomethorphan (LM) were found to be effective enantioselective inhibitors of Candida cylindracea lipase-catalyzed hydrolysis of a variety of (±)-arlypropionic and (±)-(arloxy)propionic esters. The enantioselectivity of the biocatalytic resolution of (±)-methyl 2-(2,4-dichlorophenoxy)propionate (DCPP) was enhanced 20-fold in the presence of either DM or LM. A general model for enantioselective inhibition has been developed, and a quantitative expression has been derived to show the underlying parameters that govern enantioselective inhibition. To define the mechanism of action of DM, a series of kinetic inhibition experiments was conducted with enantiomerically pure (R)-(+)-DCPP and (S)-(-)-DCPP. The observed inhibition pattern was that of partial noncompetitive inhibition for (R)-(+)-DCPP and that of pure noncompetitive inhibition for (S)-(-)-DCPP.