Skip to Content
Merck
All Photos(4)

Documents

M7397

Sigma-Aldrich

L-(−)-Malic acid

suitable for cell culture, BioReagent, suitable for insect cell culture

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:
12352205
PubChem Substance ID:
24897161
NACRES:
NA.75

biological source

microbial

product line

BioReagent

Assay

≥95% (titration)

form

powder

technique(s)

cell culture | insect: suitable
cell culture | mammalian: suitable

mp

101-103 °C (lit.)

solubility

water: 100 mg/mL, clear to 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

Related Categories

General description

Malic acid is used as a component of insect tissue culture. It is also useful as an acidulant in soft drinks, jams, fruit and vegetable juices.

Application

Malic acid has been used:
  • to induce basal respiration in mitochondrial cell culture
  • to measure the mitochondrial ETC (electron transport chain) activity
  • as a component of mitochondrial substrate stock

Biochem/physiol Actions

Malic acid is a part of cellular metabolism. Its application is recognized in pharmaceutics. It is useful in the treatment of hepatic malfunctioning, effective against hyper-ammonemia. It is used as a part of amino acid infusion. Malic acid also serves as a nanomedicine in the treatment of brain neurological disorders. A TCA (Krebs cycle) intermediate and partner in the malic acid aspartate shuttle.

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

Increased mitochondrial electron transport chain activity at complex I is regulated by N-acetylcysteine in lymphocytes of patients with systemic lupus erythematosus
Doherty E, et al.
Antioxidants & Redox Signaling, 21(1), 56-65 (2014)
Biotechnology, 238-238 (1990)
Inhibition of brain tumor growth by intravenous poly (beta-L-malic acid) nanobioconjugate with pH-dependent drug release
Ding H, et al.
Proceedings of the National Academy of Sciences of the USA, 107(42), 18143-18148 (2010)
Continuous production of L-malic acid by immobilized Brevibacterium ammoniagenes cells
Yamamoto K, et al.
Europ. J. Appl. Microbiol. Biotechnol., 3(3), 169-183 (1976)
Invertebrate Tissue Culture, 11-11 (2012)
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