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M1000

Sigma-Aldrich

L-(−)-Malic acid

≥95% (titration)

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:
12352106
PubChem Substance ID:
24896463
NACRES:
NA.22

Quality Level

300

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

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
0000316178
0000263708
0000314592
0000305346
0000287921

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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)
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.
Asymmetric synthesis of furo [3, 2-i] indolizines from L-malic acid.
Lee YS, et al.
Tetrahedron, 55(15), 4631-4636 (1999)
A stereospecific synthesis of (-)-Bestatin from L-malic acid.
Norman BH and Morris ML.
Tetrahedron Letters, 33(45), 6803-6806 (1992)
Mc Murry JE
Organic Chemistry , Biological Approach (2016)
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