M6413

L-(−)-Malic acid

Name: <SC>L</SC>-(−)-Malic acid
Brand: SIGMA

BioXtra, ≥95%

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:

24897010

NACRES:

NA.25

Key Documents

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grade

BioPerformance Certified

Quality Level

200

product line

BioXtra

Assay

≥95%

form

powder

impurities

≤0.01% Phosphorus (P)
≤0.1% Insoluble matter

ash

<0.1%

mp

101-103 °C (lit.)

solubility

H₂O: 0.5 M at 20 °C, clear, colorless

anion traces

chloride (Cl^-): ≤0.05%
sulfate (SO₄^2-): ≤0.05%

cation traces

Al: ≤0.0005%
Ca: ≤0.0005%
Cu: ≤0.0005%
Fe: ≤0.0005%
K: ≤0.005%
Mg: ≤0.0005%
NH₄⁺: ≤0.05%
Na: ≤0.005%
Pb: ≤0.001%
Zn: ≤0.0005%

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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Biochemicals

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Show Differences

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This Item	M1000	112577	M7397
Sigma-Aldrich M6413 L-(−)-Malic acid	Sigma-Aldrich M1000 L-(−)-Malic acid	Sigma-Aldrich 112577 L-(−)-Malic acid	Sigma-Aldrich M7397 L-(−)-Malic acid
assay ≥95%	assay ≥95% (titration)	assay 97%	assay ≥95% (titration)
Quality Level 200	Quality Level 300	Quality Level 200	Quality Level 200
form powder	form powder	form powder	form powder
solubility H₂O: 0.5 M at 20 °C, clear, colorless	solubility water: 100 mg/mL, clear to very slightly hazy, colorless	solubility -	solubility water: 100 mg/mL, clear to slightly hazy, colorless
impurities ≤0.01% Phosphorus (P), ≤0.1% Insoluble matter	impurities -	impurities -	impurities -
anion traces chloride (Cl^-): ≤0.05%, sulfate (SO₄^2-): ≤0.05%	anion traces -	anion traces -	anion traces -

Pictograms

GHS07

Signal Word

Warning

Hazard Statements

H315,H319

Precautionary Statements

P264 - P280 - P302 + P352 - P305 + P351 + P338 - P332 + P313 - P337 + P313

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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Premature synaptic mitochondrial dysfunction in the hippocampus during aging contributes to memory loss.

Margrethe A Olesen et al.

Redox biology, 34, 101558-101558 (2020-05-25)

Aging is a process characterized by cognitive impairment and mitochondrial dysfunction. In neurons, these organelles are classified as synaptic and non-synaptic mitochondria depending on their localization. Interestingly, synaptic mitochondria from the cerebral cortex accumulate more damage and are more sensitive

Fecal IgA Levels Are Determined by Strain-Level Differences in Bacteroides ovatus and Are Modifiable by Gut Microbiota Manipulation.

Chao Yang et al.

Cell host & microbe, 27(3), 467-475 (2020-02-23)

Fecal IgA production depends on colonization by a gut microbiota. However, the bacterial strains that drive gut IgA production remain largely unknown. Here, we assessed the IgA-inducing capacity of a diverse set of human gut microbial strains by monocolonizing mice

Isolation and functional analysis of peridroplet mitochondria from murine brown adipose tissue.

Jennifer Ngo et al.

STAR protocols, 2(1), 100243-100243 (2021-01-19)

Mitochondria play a central role in lipid metabolism and can bind to lipid droplets. However, the role and functional specialization of the population of peridroplet mitochondria (PDMs) remain unclear, as methods to isolate functional PDMs were not developed until recently.

Isotopically nonstationary 13C flux analysis of cyanobacterial isobutyraldehyde production.

Lara J Jazmin et al.

Metabolic engineering, 42, 9-18 (2017-05-10)

We applied isotopically nonstationary 13C metabolic flux analysis (INST-MFA) to compare the pathway fluxes of wild-type (WT) Synechococcus elongatus PCC 7942 to an engineered strain (SA590) that produces isobutyraldehyde (IBA). The flux maps revealed a potential bottleneck at the pyruvate

Target Discovery of Selective Non-Small-Cell Lung Cancer Toxins Reveals Inhibitors of Mitochondrial Complex I.

Nikhil Madhusudhan et al.

ACS chemical biology, 15(1), 158-170 (2019-12-25)

Selective toxicity among cancer cells of the same lineage is a hallmark of targeted therapies. As such, identifying compounds that impair proliferation of a subset of non-small-cell lung cancer (NSCLC) cell lines represents one strategy to discover new drugs for

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