Skip to Content
MilliporeSigma
All Photos(1)

Documents

727075

Sigma-Aldrich

(R)-(−)-Mandelic acid

ChiPros®, produced by BASF, 99%

Synonym(s):

(R)-α-Hydroxyphenylacetic acid

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Linear Formula:
C6H5CH(OH)CO2H
CAS Number:
611-71-2
Molecular Weight:
152.15
Beilstein/REAXYS Number:
2691094
EC Number:
210-276-6
MDL number:
MFCD00064251
UNSPSC Code:
12352106
PubChem Substance ID:
329764292
NACRES:
NA.22

grade

produced by BASF

assay

≥98.5%
99%

form

crystals

optical purity

enantiomeric excess: ≥98.5%

mp

131-133 °C (lit.)

SMILES string

O[C@@H](C(O)=O)c1ccccc1

InChI

1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/t7-/m1/s1

InChI key

IWYDHOAUDWTVEP-SSDOTTSWSA-N

Looking for similar products? Visit Product Comparison Guide

General description

(R)-(−)-Mandelic acid is a chiral resolving agent, which is also used as a chiral building block in the preparation of semisynthetic cephalosporins, antitumor agents, and penicillins.

Application

(R)-(−)-Mandelic acid can be used:
  • As a chiral acid in the separation of diastereomeric salts for the synthesis of chiral pyridoindole based building block.
  • In the study of chiral acid selectivity of poly(3,4-ethylenedioxythiophene) (PEDOT) based chiral conducting polymers.

Legal Information

ChiPros is a registered trademark of BASF SE

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H318

Hazard Classifications

Eye Dam. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

>374.0 °F

flash_point_c

> 190 °C

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Chiral acid selectivity displayed by PEDOT electropolymerised in the presence of chiral molecules
Sulaiman Y and Kataky R
Analyst, 137(10), 2386-2393 (2012)
Biocatalytic synthesis of (R)-(−)-mandelic acid from racemic mandelonitrile by a newly isolated nitrilase-producer Alcaligenes sp. ECU0401
He YC, et al.
Chinese Chemical Letters = Zhongguo Hua Xue Kuai Bao, 18(6), 677-680 (2007)
A Short Synthesis of the 2-Bromo-N, 9-dimethyl-6, 7, 8, 9-tetrahydro-5 H-pyrido [2, 3-b] indol-6-amine Building Block
Sreenivasachary N, et al.
Organic Process Research & Development, 23(11), 2521-2526 (2019)
M Monier et al.
International journal of biological macromolecules, 55, 207-213 (2013-01-30)
An enantioselective S-mandelic acid (S-MA) imprinted chitosan (SMIC) was prepared by cross-linking of chitosan using formaldehyde cross-linker, in the presence of S-MA as an imprint template molecule and 0.5% acetic acid solution as a solvent. Non-imprinted cross-linked chitosan (NIC) as
Ling-Bo Gao et al.
Chirality, 24(1), 86-95 (2011-12-06)
Mandelic acid (MA) is generally used as a biological indicator of occupational exposure to styrene, which is classified as a class of hazardous environmental pollutants. It was found to undergo one-directional chiral inversion (S-MA to R-MA) in Wistar and Sprague-Dawley
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service