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112577

L-(−)-Malic acid

Name: <SC>L</SC>-(−)-Malic acid
Brand: ALDRICH

97%, optical purity ee: 99% (GLC)

Synonym(s):

(S)-(−)-2-Hydroxysuccinic acid, L-Hydroxybutanedioic acid

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About This Item

Linear Formula:

HO₂CCH₂CH(OH)CO₂H

CAS Number:

97-67-6

Molecular Weight:

134.09

UNSPSC Code:

12352106

NACRES:

NA.22

PubChem Substance ID:

24847101

EC Number:

202-601-5

Beilstein/REAXYS Number:

1723541

MDL number:

MFCD00064213

Assay:

97%

Form:

powder

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Properties

Quality Level

200

assay

97%

form

powder

optical activity

[α]20/D −27°, c = 5.5 in pyridine

optical purity

ee: 99% (GLC)

mp

101-103 °C (lit.)

functional group

carboxylic acid, hydroxyl

SMILES string

O[C@@H](CC(O)=O)C(O)=O

InChI

1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m0/s1

InChI key

BJEPYKJPYRNKOW-REOHCLBHSA-N

Description

General description

L-(-)-Malic acid is an organic acid that is commonly found in wine. It plays an important role in wine microbiological stability.

Application

L-(-)-Malic acid is a selective α-amino protecting reagent for amino acid derivatives. It is also a versatile synthon for the preparation of chiral compounds including κ-opioid receptor agonists, 1α,25-dihydroxyvitamin D₃ analogue, and phoslactomycin B.

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pictograms

GHS07

signalword

Warning

hcodes

H315,H319

pcodes

P264 - P280 - P302 + P352 - P305 + P351 + P338 - P332 + P313 - P337 + P313

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Bioorganic & Medicinal Chemistry Letters, 2, 1713-1713 (1992)

Tetrahedron Letters, 48, 5601-5601 (2007)

Reversible enzymic protection of the alpha-amino group of amino acid derivatives using an aminopeptidase A.

I Yoshpe-Besançon et al.

Biotechnology and applied biochemistry, 18 ( Pt 1), 93-102 (1993-08-01)

In previous papers we have reported that an aminopeptidase A (EC 3.4.11.7) purified from Staphylococcus chromogenes was able to catalyse the introduction of L-malic acid at the N-terminus of Tyr and Phe derivatives. We now show that this enzyme can

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Global Trade Item Number

SKU	GTIN
112577-100G	04061838700049
112577-25G	04061838700056