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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:
17199-29-0
Molecular Weight:
152.15
Beilstein:
2208678
EC Number:
241-240-8
MDL number:
MFCD00004495
UNSPSC Code:
12352002
PubChem Substance ID:
329767945
NACRES:
NA.22

Quality Level

100

product line

ReagentPlus®

Assay

≥99%

form

crystals

mp

131-134 °C (lit.)
132-138 °C

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
GHS05

Signal Word

Danger

Hazard Statements

H318

Precautionary Statements

P280 - P305 + P351 + P338 + P310

Hazard Classifications

Eye Dam. 1

WGK

WGK 3

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 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)
The Journal of Organic Chemistry, 58, 2313-2313 (1993)
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