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240176

Sigma-Aldrich

DL-Malic acid

ReagentPlus®, ≥99%

Synonym(s):

(±)-2-Hydroxysuccinic acid, DL-Hydroxybutanedioic acid

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About This Item

Linear Formula:
HO2CCH2CH(OH)CO2H
CAS Number:
6915-15-7
Molecular Weight:
134.09
Beilstein:
1723539
EC Number:
230-022-8
MDL number:
MFCD00064212
UNSPSC Code:
12352100
PubChem Substance ID:
24854408
NACRES:
NA.22

vapor density

4.6 (vs air)

vapor pressure

<0.1 mmHg ( 20 °C)

product line

ReagentPlus®

Assay

≥99%

form

solid

autoignition temp.

644 °F

mp

131-133 °C (lit.)

solubility

acetone: soluble 17.75g/100g at 20 °C(lit.)
diethyl ether: soluble 0.84g/100g at 20 °C(lit.)
dioxane: soluble 22.7 g/100g at 20 °C(lit.)
ethanol: soluble 45.53g/100g at 20 °C(lit.)
methanol: soluble 82.7 g/100g at 20 °C(lit.)
water: soluble 55.8g/100g at 20 °C(lit.)
benzene: insoluble(lit.)

SMILES string

OC(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)

InChI key

BJEPYKJPYRNKOW-UHFFFAOYSA-N

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General description

The chiral resolution of DL-malic acid by ligand-exchange capillary electrophoresis was studied.

Application

DL-Malic acid (MA) can be used:
  • As a dopant in the ammonium dihydrogen phosphate (ADP) crystal to improve the properties of ADP crystals.
  • To form a water-soluble complex, Nb-MA which can further react with LiCl to form lithium niobate (LiNbO3) powders.
  • As a monomer to synthesize a co-polymer, poly(DL-lactic acid-co-α,β-malic acid) (PLMA) with DL-lactic acid which can be coated over magnetic Fe3O4 nanoparticles after functionalizing with fluorescein isothiocyanate (FITC), to be used as a MRI T2-contrast agent.

Legal Information

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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319

Hazard Classifications

Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

397.4 °F

Flash Point(C)

203 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Chemical synthesis of lithium niobate powders (LiNbO3) prepared from water-soluble DL-malic acid complexes
Camargo ER and Kakihana M
Chemistry of Materials, 13(5), 1905-1909 (2001)
Biodegradable magnetic-fluorescent magnetite/poly (DL-lactic acid-co-?, ?-malic acid) composite nanoparticles for stem cell labeling
Wang L, et al.
Biomaterials, 31(13), 3502-3511 (2010)
Growth of DL-malic acid-doped ammonium dihydrogen phosphate crystal and its characterization
Rajesh P and Ramasamy P
Journal of Crystal Growth, 311(13), 3491-3497 (2009)
S Kodama et al.
Electrophoresis, 22(15), 3286-3290 (2001-10-09)
Chiral resolution of native DL-malic acid was achieved by ligand-exchange capillary electrophoresis using copper(II)-L-tartrate as a chiral selector. Factors affecting chiral resolution, migration time, and peak area of malic acid were studied. The running conditions for optimum separation of malic
G Anneroth et al.
Scandinavian journal of dental research, 88(3), 214-218 (1980-06-01)
Two saliva stimulating drugs, solutions of Hybrin and malic acid were in an in vitro study found to have a heavy demineralizing effect on the root surface of the dental hard tissue. Consequently the drugs cannot be recommended to patients
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