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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.)

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

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’.

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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)
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)
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)
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
Benedict T Green et al.
The Journal of pharmacology and experimental therapeutics, 344(1), 295-307 (2012-10-23)
Coniine is an optically active toxic piperidine alkaloid and nicotinic acetylcholine receptor (nAChR) agonist found in poison hemlock (Conium maculatum L.). Coniine teratogenicity is hypothesized to be attributable to the binding, activation, and prolonged desensitization of fetal muscle-type nAChR, which
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