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M7397

Sigma-Aldrich

L-(−)-Malic acid

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

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

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This Item
M1000112577M6413
L-(−)-Malic acid BioReagent, suitable for cell culture, suitable for insect cell culture

Sigma-Aldrich

M7397

L-(−)-Malic acid

-
L-(−)-Malic acid ≥95% (titration)

Sigma-Aldrich

M1000

L-(−)-Malic acid

-
L-(−)-Malic acid 97%, optical purity ee: 99% (GLC)

Sigma-Aldrich

112577

L-(−)-Malic acid

-
L-(−)-Malic acid BioXtra, ≥95%

Sigma-Aldrich

M6413

L-(−)-Malic acid

Premium Grade
form

powder

form

powder

form

powder

form

powder

mp

101-103 °C (lit.)

mp

101-103 °C (lit.)

mp

101-103 °C (lit.)

mp

101-103 °C (lit.)

solubility

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

solubility

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

solubility

-

solubility

H2O: 0.5 M at 20 °C, clear, colorless

Quality Level

200

Quality Level

200, 300

Quality Level

200

Quality Level

200

biological source

microbial

biological source

-

biological source

-

biological source

-

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

Signal Word

Warning

Hazard Statements

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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25G
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USP

1374601

Malic acid

Analysis of regional brain mitochondrial bioenergetics and susceptibility to mitochondrial inhibition utilizing a microplate based system
Sauerbeck A, et al.
Journal of Neuroscience Methods, 198(1), 36-43 (2011)
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)
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)

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