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Key Documents

778052

Sigma-Aldrich

(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
Beilstein:
2208678
EC Number:
MDL number:
UNSPSC Code:
12352002
PubChem Substance ID:
NACRES:
NA.22

product line

ReagentPlus®

Assay

≥99%

form

crystals

mp

131-134 °C (lit.)
132-138 °C

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-/m0/s1

InChI key

IWYDHOAUDWTVEP-ZETCQYMHSA-N

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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

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

Eye Dam. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

>374.0 °F

Flash Point(C)

> 190 °C


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Tetrahedron, 50, 5049-5049 (1994)
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)
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)
The Journal of Organic Chemistry, 58, 2313-2313 (1993)

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