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727075

Sigma-Aldrich

(R)-(−)-Mandelic acid

ChiPros®, produced by BASF, 99%

Synonym(s):

(R)-α-Hydroxyphenylacetic acid

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About This Item

Linear Formula:
C6H5CH(OH)CO2H
CAS Number:
611-71-2
Molecular Weight:
152.15
Beilstein:
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.)

functional group

carboxylic acid
hydroxyl
phenyl

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

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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

Signal Word

Danger

Hazard Statements

H318

Precautionary Statements

P280 - P305 + P351 + P338

Hazard Classifications

Eye Dam. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

>374.0 °F

Flash Point(C)

> 190 °C

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK8655
BCCH9458
BCBH7332V
BCBH7332

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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)
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
Shimin Mao et al.
Journal of separation science, 35(17), 2273-2281 (2012-07-19)
Resolution of racemic mandelic acid ((R,S)-MA) and numerical determination of binary competitive isotherm of (R,S)-MA on Chiralcel-OD column have been investigated in this study. The effects of the alcohol modifier and acidic additive in the mobile phase on the retention
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