778052

Sigma-Aldrich

(S)-(+)-Mandelic acid

ReagentPlus®, ≥99%

Synonym(s):
(S)-α-Hydroxyphenylacetic acid
Linear Formula:
C6H5CH(OH)CO2H
CAS Number:
Molecular Weight:
152.15
Beilstein/REAXYS Number:
2208678
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

product line

ReagentPlus®

Quality Level

assay

≥99%

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.

Packaging

25, 100 g in poly bottle

Legal Information

ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Precautionary Statements

hazcat

Eye Dam. 1

storage_class_code

11 - Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

374.0 °F

Flash Point(C)

> 190 °C

Certificate of Analysis

Certificate of Origin

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)
The Journal of Organic Chemistry, 58, 2313-2313 (1993)
Synthetic Communications, 23, 2761-2761 (1993)
A Lamouri et al.
Journal of medicinal chemistry, 36(8), 990-1000 (1993-04-16)
To further investigate our hypothesis on the structure of the platelet-activating factor (PAF) receptor, 35 compounds derived from 1,4-bis(3',4',5'-trimethoxybenzoyl)piperazine were synthesized and their in vitro antagonistic effect was measured. Substitution of the compounds in position 2, by ester or carbamate...

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