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02288

Sigma-Aldrich

L-(−)-Malic acid

ReagentPlus®, ≥99%

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
Beilstein:
1723541
EC Number:
202-601-5
MDL number:
MFCD00064213
UNSPSC Code:
51113400
PubChem Substance ID:
329747409
NACRES:
NA.22

Quality Level

100

product line

ReagentPlus®

Assay

≥99%

optical activity

[α]20/D −30±2°, c = 5.5% in pyridine

impurities

≤0.3% water

ign. residue

≤0.1% (as SO4)

mp

101-103 °C (lit.)

cation traces

Fe: ≤10 mg/kg

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

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Application

L-(−)-Malic acid can be used:
  • As a carboxylate ligand in the preparation of a variety of chiral metal malates and coordination polymers.
  • In the preparation of poly(malic acid), which is a biodegradable, bioabsorbable and water-soluble polymer.
  • As a key ingredient in the total synthesis of (+)-australine, (+)-brasilenyne, epothilones B and D.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCH1350
BCCF5987
BCBW4666
BCBP3213V
BCBJ6832V

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Total syntheses of epothilones B and D.
Mulzer J, et al.
The Journal of Organic Chemistry, 65(22), 7456-7467 (2000)
Synthesis, Structure and Magnetic properties of Chiral and Nonchiral Transition?Metal Malates.
Beghidja A, et al.
Chemistry?A European Journal , 12(29), 7627-7638 (2006)
Coordination polymers built with a linear bis-imidazole and different dicarboxylates: unusual entanglement and emission properties.
Singh R and Bharadwaj P K
Crystal Growth & Design, 13(8), 3722-3733 (2013)
Synthesis of polyhydroxylated pyrrolizidine alkaloids of the alexine family by tandem ring-closing metathesis? transannular cyclization.(+)-Australine.
White J D and Hrnciar P
The Journal of Organic Chemistry, 65(26), 9129-9142 (2000)
Improved synthesis with high yield and increased molecular weight of poly (α, β-malic acid) by direct polycondensation.
Kajiyama T, et al.
Biomacromolecules, 5(1), 169-174 (2004)
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