727075
(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:
Molecular Weight:
152.15
UNSPSC Code:
12352106
NACRES:
NA.22
PubChem Substance ID:
EC Number:
210-276-6
Beilstein/REAXYS Number:
2691094
MDL number:
Product Name
(R)-(−)-Mandelic acid, ChiPros®, produced by BASF, 99%
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
SMILES string
O[C@@H](C(O)=O)c1ccccc1
assay
≥98.5%
99%
form
crystals
optical purity
enantiomeric excess: ≥98.5%
mp
131-133 °C (lit.)
functional group
carboxylic acid
hydroxyl
phenyl
Quality Level
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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.
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.
Legal Information
ChiPros is a registered trademark of BASF SE
signalword
Danger
hcodes
Hazard Classifications
Eye Dam. 1
Storage Class
11 - Combustible Solids
wgk
WGK 1
flash_point_f
>374.0 °F
flash_point_c
> 190 °C
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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)
Zhoutong Sun et al.
Microbial cell factories, 10, 71-71 (2011-09-14)
Mandelic acid (MA), an important component in pharmaceutical syntheses, is currently produced exclusively via petrochemical processes. Growing concerns over the environment and fossil energy costs have inspired a quest to develop alternative routes to MA using renewable resources. Herein we
Chao Ma et al.
Chirality, 23(5), 379-382 (2011-04-14)
This work reports the chiral separation of D,L-mandelic acid with cellulose membranes. Cellulose was chosen as membrane material because it possesses multichiral carbon atoms in its molecular structure unit. The flux and permselective properties of membrane using aqueous solutions of
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