M1000

Sigma-Aldrich

L-(−)-Malic acid

≥95% (titration)

Synonym(s):
L-Hydroxybutanedioic acid, (S)-(−)-2-Hydroxysuccinic acid
Linear Formula:
HO2CCH2CH(OH)CO2H
CAS Number:
Molecular Weight:
134.09
Beilstein/REAXYS Number:
1723541
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥95% (titration)

form

powder

pKa (25 °C)

(1) 3.46, (2) 5.10

mp

101-103 °C (lit.)

solubility

water: 100 mg/mL, clear to very slightly hazy, colorless

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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General description

L-Malic acid is the naturally occurring isomer of malic acid, found mainly in sour and unripe fruits.

Application

L-(-)-Malic acid may be used to prepare:
  • diethyl (S)-malate
  • ethyl (R)-2-hydroxyl-4-phenylbutanoate
  • ethyl (S)-2-hydroxyl-4-phenylbutanoate
  • D-homophenylalanine ethyl ester hydrochloride
  • furo[3,2-i]indolizines

Packaging

1 kg in poly bottle
100, 500 g in poly bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

hazcat

Eye Irrit. 2

storage_class_code

11 - Combustible Solids

WGK Germany

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Lei Shi et al.
Science (New York, N.Y.), 368(6497) (2020-05-23)
Although perovskite solar cells have produced remarkable energy conversion efficiencies, they cannot become commercially viable without improvements in durability. We used gas chromatography-mass spectrometry (GC-MS) to reveal signature volatile products of the decomposition of organic hybrid perovskites under thermal stress....
A stereospecific synthesis of (-)-Bestatin from L-malic acid.
Norman BH and Morris ML.
Tetrahedron Letters, 33(45), 6803-6806 (1992)
Asymmetric synthesis of furo [3, 2-i] indolizines from L-malic acid.
Lee YS, et al.
Tetrahedron, 55(15), 4631-4636 (1999)
A practical synthesis of ethyl (R)-and (S)-2-hydroxy-4-phenylbutanoate and D-homophenylalanine ethyl ester hydrochloride from L-malic acid.
Lin WQ, et al.
Tetrahedron Asymmetry, 12(11), 1583-1587 (2001)
Mc Murry JE
Organic Chemistry , Biological Approach (2016)
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