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
Beilstein/REAXYS Number:
2691094
EC Number:
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.22
Quality Level
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
signalword
Danger
hcodes
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
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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)
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
Liang Jin et al.
Zeitschrift fur Naturforschung. C, Journal of biosciences, 66(9-10), 499-506 (2011-12-24)
To study the effects of mandelic acid (MA) on the brown planthopper (BPH), Nilaparvata lugens, the survival rate and behaviour of BPH fed on an artificial diet with different dosages of MA was observed. The survival rate of BPH decreased
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
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
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