Skip to Content
Merck
All Photos(1)

Documents

02288

Sigma-Aldrich

L-(−)-Malic acid

ReagentPlus®, ≥99%

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

Looking for similar products? Visit Product Comparison Guide

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
BCCH1350
BCCF5987
BCBW4666
BCBP3213V
BCBJ6832V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
Total syntheses of epothilones B and D.
Mulzer J, et al.
The Journal of Organic Chemistry, 65(22), 7456-7467 (2000)
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)
L C Katwa et al.
The Biochemical journal, 283 ( Pt 3), 727-735 (1992-05-01)
Certain nucleotides were found to regulate the binding of the Escherichia coli heat-stable enterotoxin (STa) to its receptor in pig intestinal brush border membranes. ATP and adenine nucleotide analogues inhibited 125I-STa binding, while guanine nucleotide analogues stimulated binding, with maximal
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)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service