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Merck

02288

L-(−)-Malic acid

ReagentPlus®, ≥99%

Synonym(s):

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

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10 G

¥2,200

50 G

¥5,872

¥2,200

List Price¥2,980Save 26%

Estimated to ship onDecember 01, 2025Details


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About This Item

Linear Formula:
HO2CCH2CH(OH)CO2H
CAS Number:
Molecular Weight:
134.09
Beilstein:
1723541
EC Number:
MDL number:
UNSPSC Code:
51113400
PubChem Substance ID:
NACRES:
NA.22

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Quality Level

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

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

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1 of 4

This Item
M6413112577M7397
assay

≥99%

assay

≥95%

assay

97%

assay

≥95% (titration)

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

200

mp

101-103 °C (lit.)

mp

101-103 °C (lit.)

mp

101-103 °C (lit.)

mp

101-103 °C (lit.)

product line

ReagentPlus®

product line

BioXtra

product line

-

product line

BioReagent

optical activity

[α]20/D −30±2°, c = 5.5% in pyridine

optical activity

-

optical activity

[α]20/D −27°, c = 5.5 in pyridine

optical activity

-

impurities

≤0.3% water

impurities

≤0.01% Phosphorus (P), ≤0.1% Insoluble matter

impurities

-

impurities

-

Application

L-(−)-Malic acid can be used:
  • As a carboxylate ligand in the preparation of a variety of chiral metal malates and coordination polymers.[1][2]
  • In the preparation of poly(malic acid), which is a biodegradable, bioabsorbable and water-soluble polymer.[3]
  • As a key ingredient in the total synthesis of (+)-australine[4], (+)-brasilenyne[5], epothilones B and D.[6]

Legal Information

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

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

02288-VAR:
02288-50G:
02288-10G:
02288-BULK:


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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
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)
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)

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