Skip to Content
Merck
All Photos(4)

Documents

M1000

Sigma-Aldrich

L-(−)-Malic acid

≥95% (titration)

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(4)

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

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

Looking for similar products? Visit Product Comparison Guide

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

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
A stereospecific synthesis of (-)-Bestatin from L-malic acid.
Norman BH and Morris ML.
Tetrahedron Letters, 33(45), 6803-6806 (1992)
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)
Mc Murry JE
Organic Chemistry , Biological Approach (2016)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service