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(R)-Mandelic acid

$43

  • Brand : BIOFRON

  • Catalogue Number : BF-R3001

  • Specification : 98%

  • CAS number : 611-71-2

  • Formula : C8H8O3

  • Molecular Weight : 152.15

  • PUBCHEM ID : 11914

  • Volume : 100mg

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Catalogue Number

BF-R3001

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

152.15

Appearance

White crystalline powder

Botanical Source

Semen Armeniacae Amarum.

Structure Type

Others

Category

Standards;Natural Pytochemical;API

SMILES

C1=CC=C(C=C1)C(C(=O)O)O

Synonyms

(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

IUPAC Name

(2R)-2-hydroxy-2-phenylacetic acid

Density

1.3±0.1 g/cm3

Solubility

Methanol; Water; DMSO

Flash Point

162.6±18.8 °C

Boiling Point

321.8±22.0 °C at 760 mmHg

Melting Point

130-134ºC

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2918190000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

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

PMID

32193756

Abstract

(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.

KEYWORDS

(R)-mandelic acid; Enantioselective hydrolysis; Fermentation; Nitrilase; Upscale production

Title

Upscale production of (R)-mandelic acid with a stereospecific nitrilase in an aqueous system.

Author

Zhang XH1,2, Wang CY2, Cai X1, Xue YP1, Liu ZQ3, Zheng YG1.

Publish date

2020 Mar 20

PMID

28936681

Abstract

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.

KEYWORDS

Alcaligenes faecalis; Enantioselective hydrolysis; Immobilized cells; Nitrilase; R-mandelic acid; Tris(hydroxymethyl)phosphine

Title

Production of R-Mandelic Acid Using Nitrilase from Recombinant E. coli Cells Immobilized with Tris(Hydroxymethyl)Phosphine.

Author

Zhang XH1, Liu ZQ1, Xue YP1, Wang YS1, Yang B1, Zheng YG2.

Publish date

2018 Mar

PMID

29562093

Abstract

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.

Title

Investigation of Mechanistic Pathway for Trimethyl Borate Mediated Amidation of (R)-Mandelic Acid for the Synthesis of Mirabegron, an Antimuscarinic Agent.

Author

Deshmukh DG, Bangal MN, Patekar MR, Medhane VJ, Mathad VT.

Publish date

2018 Mar


Description :

D-(-)-Mandelic acid is a natural compound isolated from bitter almonds.