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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

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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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.
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)
Mc Murry JE
Organic Chemistry , Biological Approach (2016)
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