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Merck
CN

M2004

(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
EC Number:
241-240-8
UNSPSC Code:
12352200
PubChem Substance ID:
Beilstein/REAXYS Number:
2208678
MDL number:
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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%

optical activity

[α]20/D +154°, c = 2.8 in H2O

optical purity

ee: 99% (GLC)

mp

131-134 °C (lit.)

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General description

N-Methyl-D-glucamine (Meglumine) is a sorbitol derivative in which one of the hydroxyl groups has been replaced with a methylamino group. Meglumine is widely used with iodinated organic compounds as a contrast media.

Application

N-Methyl-D-glucamine can be used as a co-crystal conformer as well as a salt-forming agent due to its hydrophilic nature and ability to modify the crystalline structure of the drug molecule to improve solubility.
It is also used to functionalize polymers and resins to develop chelating agents for the removal of boron and arsenic from wastewater.
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

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

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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The Journal of Organic Chemistry, 58, 2313-2313 (1993)
Tetrahedron, 50, 5049-5049 (1994)
Melanie Balbach et al.
Frontiers in cell and developmental biology, 8, 572735-572735 (2020-09-29)
Mammalian oocytes are enveloped by the zona pellucida (ZP), an extracellular matrix of glycoproteins. In sperm, stimulation with ZP proteins evokes a rapid Ca2+ influx via the sperm-specific, pH-sensitive Ca2+ channel CatSper. However, the physiological role and molecular mechanisms underlying
Synthetic Communications, 23, 2761-2761 (1993)
Janine Obendorf et al.
Stem cell research & therapy, 11(1), 525-525 (2020-12-11)
Mesenchymal stem cells (MSCs) were shown to harbor therapeutic potential in models of respiratory diseases, such as bronchopulmonary dysplasia (BPD), the most common sequel of preterm birth. In these studies, cells or animals were challenged with hyperoxia or other injury-inducing

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