778052
(S)-(+)-Mandelic acid
ReagentPlus®, ≥99%
Synonym(s):
(S)-α-Hydroxyphenylacetic acid
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About This Item
Linear Formula:
C6H5CH(OH)CO2H
CAS Number:
Molecular Weight:
152.15
UNSPSC Code:
12352002
NACRES:
NA.22
PubChem Substance ID:
EC Number:
241-240-8
Beilstein/REAXYS Number:
2208678
MDL number:
Product Name
(S)-(+)-Mandelic acid, ReagentPlus®, ≥99%
InChI key
IWYDHOAUDWTVEP-ZETCQYMHSA-N
InChI
1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/t7-/m0/s1
SMILES string
O[C@H](C(O)=O)c1ccccc1
product line
ReagentPlus®
assay
≥99%
form
crystals
mp
131-134 °C (lit.)
132-138 °C
functional group
carboxylic acid
hydroxyl
phenyl
Quality Level
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Application
(S)-(+)-Mandelic acid can be used as a starting material to synthesize (S)-cyclohexenyl phenyl glycoxilic acid, an optically active tertiary α-hydroxy acid component of (S)-oxybutynin.
It is a versatile reagent used in the resolution of racemates and the preparation of amides.
Legal Information
ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany
signalword
Danger
hcodes
Hazard Classifications
Eye Dam. 1
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
>374.0 °F
flash_point_c
> 190 °C
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The Journal of Organic Chemistry, 58, 2313-2313 (1993)
Chiral mandelic acid template provides a highly practical solution for (S)-oxybutynin synthesis.
Grover P T, et al.
The Journal of Organic Chemistry, 65(19), 6283-6287 (2000)
Tetrahedron, 50, 5049-5049 (1994)
Mara Reifenrath et al.
Metabolic engineering communications, 7, e00079-e00079 (2018-10-30)
Mandelic acid is an important aromatic fine chemical and is currently mainly produced via chemical synthesis. Recently, mandelic acid production was achieved by microbial fermentations using engineered Escherichia coli and Saccharomyces cerevisiae expressing heterologous hydroxymandelate synthases (hmaS). The best-performing strains
Synthetic Communications, 23, 2761-2761 (1993)
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