127984-21-8

Basic information

• Product Name: N-((S)-mandeloyl)-L-phenylalanine
• Synonyms: N-((S)-mandeloyl)-L-phenylalanine
• CAS NO: 127984-21-8
• Molecular Weight: 299.326
• Mol File: 127984-21-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: N-((S)-mandeloyl)-L-phenylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: N-((S)-mandeloyl)-L-phenylalanine(127984-21-8)
• EPA Substance Registry System: N-((S)-mandeloyl)-L-phenylalanine(127984-21-8)

Safety Data

• Hazardous Substances Data: 127984-21-8(Hazardous Substances Data)

Upstream product

• 150-30-1 Phenylalanine 
• 4358-86-5 (S)-mandelamide 
• 21210-43-5 (S)-Methyl mandelate 
• 127984-14-9 2-(2-oxo-2-phenylacetamido)-3-phenylpropanoic acid 
• 63-91-2 L-phenylalanine 
• 17199-29-0 (S)-Mandelic acid 
• 51019-43-3 (R)-(-)-O-acetylmandelic acid 
• 611-71-2 (R)-Mandelic Acid 
• 49845-69-4 (R)-O-acetylmandeloyl chloride 

Downstream Products

• 63-91-2 L-phenylalanine 

Relevant articles and documents

Investigating chiral recognizability of diastereomeric crystallization of mandelic acid and L-phenylalanine

The present study investigated the mechanism of the chiral recognition of the resolving agent (L-phenylalanine) to the chiral isomers (D/L-mandelic acid). According the NMR analysis, the distinctive chemical shifts of between two diastereomer crystals (L-mandelic acid-L-phenlyalanine and D-mandelic acid-L-phenylalanine) were observed even though there was no difference of the chemicals shift of the two diastereomer solutions. This result indicated that the chiral recognition of the resolving agent mainly occurred during the crystallization of the diastereomers in the solution. Then, the chiral recognition of the diastereomers was confirmed by using thermal analysis and AFM. The diastereomer crystal of L-mandelic acid-L-phenylalanine was much more thermally stable due to the higher lattice energy than the diastereomer crystals of D-mamdelic acid-L-phenylalanine. Also, the adhesive force measured with AFM exhibited a stronger molecular interaction between L-mandelic acid and 4-amino-L-phenylalanine than between D-mandelic acid and 4-amino-L- phenylalanine. Plus, the AFM results implied that the hydroxyl group abundance on the mandelic acid surface was a possible explanation for the different chiral selectivity of the L-phenylalanine. Copyright

Asymmetric hydrogenation of α-keto acid derivatives with Rh(I)-chiral diphosphinite system. Effect of halide counterion on the asymmetric induction

A chiral diphosphinite ligand having dicyclo-hexylphosphinooxy and dimethylamino moieties (Cy-POP-AE) was effective for the asymmetric hydrogenation of N-(benzoylformyl) amino acids by a Rh(I) catalyst under mild conditions. A neutral rhodium(I) precursor enabled a double asymmetric induction in methanol, while a cationic precursor caused an asymmetric induction controlled mainly by the substrate chirality.