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309974

Sigma-Aldrich

Ethyl (S)-(+)-mandelate

99%, optical purity ee: 99% (GLC)

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Linear Formula:
C6H5CH(OH)CO2C2H5
CAS Number:
Molecular Weight:
180.20
MDL number:
UNSPSC Code:
12352108
PubChem Substance ID:
NACRES:
NA.22

Assay

99%

form

solid

optical activity

[α]21/D +134°, c = 3 in chloroform

optical purity

ee: 99% (GLC)

bp

106-107 °C/4 mmHg (lit.)

mp

32-34 °C (lit.)

SMILES string

CCOC(=O)[C@@H](O)c1ccccc1

InChI

1S/C10H12O3/c1-2-13-10(12)9(11)8-6-4-3-5-7-8/h3-7,9,11H,2H2,1H3/t9-/m0/s1

InChI key

SAXHIDRUJXPDOD-VIFPVBQESA-N

Application

Ethyl (S)-(+)-mandelate can be used as a starting material for the preparation of N-benzyl 2-phenylacetamide derivatives, which are known as potent anticonvulsant agents.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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The anticonvulsant activities of functionalized N-benzyl 2-acetamidoacetamides. The importance of the 2-acetamido substituent
Choi D, et al.
Bioorganic & Medicinal Chemistry, 4(12), 2105-2114 (1996)
Asteriani R Dewanti et al.
Biochemistry, 43(7), 1883-1890 (2004-02-18)
(S)-Mandelate dehydrogenase (MDH) from Pseudomonas putida is a flavin mononucleotide (FMN)-dependent enzyme that oxidizes (S)-mandelate to benzoylformate. In this work, we show that the ethyl and methyl esters of (S)-mandelic acid are substrates for MDH. Although the binding affinity of

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