L-(-)-Malic acid

SKU: orb1221405

Description

Malic acid is a tart-tasting organic dicarboxylic acid that plays a role in many sour or tart foods. Apples contain malic acid which contributes to the sourness of a green apple. Malic acid can make a wine taste tart although the amount decreases with increasing fruit ripeness. (wikipedia). In its ionized form malic acid is called malate. Malate is an intermediate of the TCA cycle along with fumarate. It can also be formed from pyruvate as one of the anaplerotic reactions. In humans malic acid is both derived from food sources and synthesized in the body through the citric acid cycle or Krebs cycle which takes place in the mitochondria. Malate's importance to the production of energy in the body during both aerobic and anaerobic conditions is well established. Under aerobic conditions the oxidation of malate to oxaloacetate provides reducing equivalents to the mitochondria through the malate-aspartate redox shuttle. During anaerobic conditions where a buildup of excess of reducing equivalents inhibits glycolysis malic acid's simultaneous reduction to succinate and oxidation to oxaloacetate is capable of removing the accumulating reducing equivalents. This allows malic acid to reverse hypoxia's inhibition of glycolysis and energy production. In studies on rats it has been found that only tissue malate is depleted following exhaustive physical activity. Other key metabolites from the citric acid cycle needed for energy production were found to be unchanged. Because of this a deficiency of malic acid has been hypothesized to be a major cause of physical exhaustion. Notably the administration of malic acid to rats has been shown to elevate mitochondrial malate and increase mitochondrial respiration and energy production.

Key Properties

• CAS Number: 97-67-6
• MW: 134.09
• Purity: >98% (HPLC)
• Formula: C₄H₆O₅
• SMILES: O[C@@H](CC(O)=O)C(O)=O
• Target: Endogenous Metabolite
• Solubility: DMSO: 10 mM

Bioactivity

• In Vitro:
  It is showed that ME is essential for (S)-2-Hydroxysuccinic acid (L-malic acid) utilization in L. casei. Furthermore, deletion of either the gene encoding the histidine kinase or the response regulator of the TC system resulted in the loss of the ability to grow on (S)-2-Hydroxysuccinic acid, thus indicating that the cognate TC system regulates and is essential for the expression of ME. Transcriptional analyses shows that expression of maeE is induced in the presence of (S)-2-Hydroxysuccinic acid and repressed by glucose, whereas TC system expression is induced by (S)-2-Hydroxysuccinic acid and is not repressed by glucose.

Storage & Handling

• Storage: Storage temperature: -20°C. Stability: ≥ 2 years
• Expiration Date: 12 months from date of receipt.
• Disclaimer: For research use only

Alternative Names

(S)-2-Hydroxysuccinic acid | (S)-(-)-HYDROXYSUCCINIC ACID

Quick Database Links

Gene Symbol

Endogenous Metabolite