White crystalline powder
Semen Armeniacae Amarum.
(S)-(+)-2-hydroxy-2-phenylacetic acid/S-mandelic acid/(-)-mandelic acid/(S)-2-Hydroxy-2-phenylacetic acid/(2R)-hydroxy(phenyl)ethanoic acid/D-mandelic acid/(S)-(+)-Amygdalic Acid/R-(-)-Mandelic acid/L-MANDELIC ACID/(R)-(-)-Mandelic acid/(R)-(-)-Amygdalic Acid/(S)-mandelic acid/L-mandelate/S-(+)-Mandelic acid/(2R)-Hydroxy(phenyl)acetic acid/Benzeneacetic acid, α-hydroxy-, (αS)-/(S)-α-Hydroxyphenylacetic acid/(-)-(R)-mandelic acid/2-phenyl-2-hydroxyethanoic acid/Benzeneacetic acid, α-hydroxy-, (αR)-/(+)-L-MANDELIC ACID/(+)-MANDELIC ACID/(S)-Mandelate/(R)-MANDELIC ACID/(2S)-Hydroxy(phenyl)acetic acid/Mandelic acid/Benzeneacetic acid, α-hydroxy-, (R)-/(+)-(S)-MANDELIC ACID/hydroxyphenylacetic acid/(S)-(+)-Mandelic acid/Benzeneacetic acid, α-hydroxy-, (S)-/phenyl-hydroxy-acetic acid/D-(-)-Mandelic acid/benzeneacetic acid, a-hydroxy-, (aR)-/(R)-(-)-Mandelicacid/L-(+)-Mandelic Acid/(R)-(−)-Mandelic acid/(2S)-hydroxy(phenyl)ethanoic acid/(D)-(-)-Mandelicacid
Methanol; Water; DMSO
321.8±22.0 °C at 760 mmHg
HS Code Reference
Personal Projective Equipment
For Reference Standard and R&D, Not for Human Use Directly.
provides coniferyl ferulate(CAS#:611-71-2) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate
(R)-Mandelic acid (R-MA) is a key precursor for the synthesis of semi-synthetic penicillin, cephalosporin, anti-obesity drugs, antitumor agents, and chiral resolving agents for the resolution of racemic alcohols and amines. In this study, an enzymatic method for the large-scale production of R-MA by a stereospecific nitrilase in an aqueous system was developed. The nitrilase activity of the Escherichia coli BL21(DE3)/pET-Nit whole cells reached 138.6 U/g in a 20,000-L fermentor. Using recombinant E. coli cells as catalyst, 500 mM R,S-mandelonitrile (R,S-MN) was resolved into 426 mM (64.85 g/L) R-MA within 8 h, and the enantiomeric excess (ee) value of R-MA reached 99%. During the purification process, pure R-MA with a recovery rate of 78.8% was obtained after concentration and crystallization. This study paved the foundation for the upscale production of R-MA using E. coli whole cells as biocatalyst.
(R)-mandelic acid; Enantioselective hydrolysis; Fermentation; Nitrilase; Upscale production
Upscale production of (R)-mandelic acid with a stereospecific nitrilase in an aqueous system.
Zhang XH1,2, Wang CY2, Cai X1, Xue YP1, Liu ZQ3, Zheng YG1.
2020 Mar 20
ecombinant Escherichia coli cells harboring nitrilase from Alcaligenes faecalis were immobilized using tris(hydroxymethyl)phosphine (THP) as the coupling agent. The optimal pH and temperature of the THP-immobilized cells were determined at pH 8.0 and 55 °C. The half-lives of THP-immobilized cells measured at 35, 40, and 50 °C were 1800, 965, and 163 h, respectively. The concentration of R-mandelic acid (R-MA) reached 358 mM after merely 1-h conversion by the immobilized cells with 500 mM R,S-mandelonitrile (R,S-MN), affording the highest productivity of 1307 g L-1 day-1 and the space-time productivity of 143.2 mmol L-1 h-1 g-1. The immobilized cells with granular shape were successfully recycled for 60 batches using 100 mM R,S-MN as substrate at 40 °C with 64% of relative activity, suggesting that the immobilized E. coli cells obtained in this study are promising for the production of R-MA.
Alcaligenes faecalis; Enantioselective hydrolysis; Immobilized cells; Nitrilase; R-mandelic acid; Tris(hydroxymethyl)phosphine
Production of R-Mandelic Acid Using Nitrilase from Recombinant E. coli Cells Immobilized with Tris(Hydroxymethyl)Phosphine.
Zhang XH1, Liu ZQ1, Xue YP1, Wang YS1, Yang B1, Zheng YG2.
The present work describes investigation of mechanistic pathway for trimethyl borate mediated amidation of (R)-mandelic acid (3) with 4-nitophenylethylamine (2) to provide (R)-2-hydroxy-N-[2-(4-nitrophenyl)ethyl]-2-phenylacetamide (4) during mirabegron synthesis. Plausible reaction mechanism is proposed by isolating and elucidating the active α-hydroxy ester intermediate 16 from the reaction mass. Trimethyl borate mediated approach proved to be selective in providing 4 without disturbing α-hydroxyl group and stereochemistry of the chiral center, and is also a greener, more economic and production friendly over the reported methods. The developed approach is rapid and efficient for the preparation of 4 with an overall yield of 85-87% and around 99.0% purity by HPLC at scale.
Investigation of Mechanistic Pathway for Trimethyl Borate Mediated Amidation of (R)-Mandelic Acid for the Synthesis of Mirabegron, an Antimuscarinic Agent.
Deshmukh DG, Bangal MN, Patekar MR, Medhane VJ, Mathad VT.
D-(-)-Mandelic acid is a natural compound isolated from bitter almonds.