| Size | Price | Stock | Qty |
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| 25g |
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| Targets |
D-Malic acid is a competitive inhibitor of L-(-)-malic acid transport. It interacts with malate transporters and enzymes involved in the tricarboxylic acid (TCA) cycle. As a chiral compound, D-malic acid serves as a versatile chiral building block for the synthesis of various pharmaceuticals and biologically active molecules. Its stereochemistry plays a critical role in its biological activity and its use as a chiral synthon. The compound's ability to inhibit malate transport suggests potential applications in studies of cellular metabolism and metabolic disorders.
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| ln Vitro |
Certain species of bacteria from the genera Arthrobacter, Brevibacterium, Corynebacterium, Pseudomonas, Bacillus, and Acinetobacter produce D-(+)-malic acid (D-malic acid) from maleic acid in pH 7.0 phosphate buffer containing 0.1% sodium chloride when cells grown in media containing citraconic acid react aerobically with maleic acid [2].
In vitro, D-malic acid is a competitive inhibitor of L-(-)-malic acid transport. It is used as a chiral building block for the synthesis of chiral compounds, including δ-opioid receptor agonists and 1α,25-dihydroxyvitamin D₃ analogues. The compound's effects on cellular metabolism can be studied in cell culture models, where it may influence TCA cycle activity and energy metabolism. D-Malic acid is also used as a selective amino-protecting reagent for amino acid derivatives. Its mild acidity and high solubility make it suitable for various biochemical applications. |
| ln Vivo |
In vivo, D-malic acid is a naturally occurring compound that is metabolized through the TCA cycle. It is an active isomer of malic acid, which is found in apples and many other fruits and plants. The compound is widely used in the food and beverage industry as an acidulant and flavor enhancer. Its role in the TCA cycle suggests that it may have effects on energy metabolism and cellular respiration. As a chiral building block, D-malic acid is used in the synthesis of pharmaceuticals and other biologically active compounds.
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| Enzyme Assay |
In vitro enzyme/receptor binding assays for D-malic acid are not extensively documented, as the compound is primarily used as a chiral building block and metabolic intermediate rather than a pharmacologically active agent. However, its ability to competitively inhibit L-(-)-malic acid transport can be assessed using transport assays in cells or membrane preparations expressing malate transporters. The compound's effects on TCA cycle enzymes can be evaluated using standard enzyme activity assays. These assays provide insights into the compound's interactions with metabolic pathways.
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| Cell Assay |
In vitro cell-based assays for D-malic acid evaluate its effects on cellular metabolism and transport. Cells are cultured in appropriate media and treated with D-malic acid, and the uptake of L-malic acid or other substrates is measured using radiolabeled or fluorescent tracers. The compound's effects on TCA cycle activity and energy metabolism are assessed by measuring oxygen consumption, ATP production, or metabolite levels. Cell viability is assessed using MTT or LDH release assays. These assays provide insights into the compound's metabolic effects.
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| Animal Protocol |
In vivo animal experiments for D-malic acid have not been extensively reported, as the compound is primarily used as a food additive and chiral building block rather than a therapeutic agent. For potential in vivo studies, D-malic acid can be administered orally or via intraperitoneal injection in animal models of metabolic disorders. The compound's effects on metabolism and energy homeostasis would be assessed by measuring blood glucose, lactate, and other metabolite levels. Comprehensive in vivo studies are needed to fully characterize the compound's pharmacological effects.
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| ADME/Pharmacokinetics |
Pharmacokinetic (PK) data for D-malic acid are limited. The compound has a molecular weight of 134.09 g/mol and is highly soluble in water. As a small, hydrophilic molecule that is a normal metabolite, D-malic acid is expected to be rapidly absorbed, distributed, and metabolized through the TCA cycle. The compound is likely excreted as carbon dioxide and water. Comprehensive ADME studies are needed to fully characterize its pharmacokinetic profile.
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| Toxicity/Toxicokinetics |
The toxicity profile of D-malic acid is generally considered favorable, as it is a naturally occurring compound and is widely used as a food additive. It has low toxicity and is generally recognized as safe (GRAS) for use in food and beverages. However, like other acids, it can cause irritation at high concentrations. It should be used with appropriate safety precautions in laboratory settings. For research use only, not for human or veterinary therapeutic use.
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| References | |
| Additional Infomation |
(R)-malic acid is an optically active malic acid with the (R)-configuration. It is the conjugate acid of (R)-malate (2-) and the enantiomer of (S)-malic acid. (R)-malic acid is found in or produced by Escherichia coli (strains K12 and MG1655). D-malic acid has been reported in blueberry, Arabidopsis thaliana, and other organisms with relevant data. See also: malic acid (note moved here); ammonium malate (note moved here).
D-Malic acid (D-(+)-Malic acid) is the (R)-enantiomer of malic acid with a molecular formula of C₄H₆O₅ and a molecular weight of 134.09 g/mol. It is a competitive inhibitor of L-(-)-malic acid transport. The compound is widely used in food, beverage, pharmaceutical, and cosmetic industries as an acidulant, flavor enhancer, and pH regulator. It is also used as a chiral synthon for the preparation of chiral compounds, including δ-opioid receptor agonists and vitamin D₃ analogues. D-Malic acid is highly soluble in water and has low toxicity. |
| Molecular Formula |
C4H6O5
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|---|---|
| Molecular Weight |
134.0874
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| Exact Mass |
134.021
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| CAS # |
636-61-3
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| PubChem CID |
92824
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| Appearance |
White to off-white solid powder
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| Density |
1.6±0.1 g/cm3
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| Boiling Point |
306.4±27.0 °C at 760 mmHg
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| Melting Point |
98-104ºC
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| Flash Point |
153.4±20.2 °C
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| Vapour Pressure |
0.0±1.5 mmHg at 25°C
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| Index of Refraction |
1.529
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| LogP |
-1.26
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
9
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| Complexity |
129
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| Defined Atom Stereocenter Count |
1
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| SMILES |
C([C@H](C(=O)O)O)C(=O)O
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| InChi Key |
BJEPYKJPYRNKOW-UWTATZPHSA-N
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| InChi Code |
InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m1/s1
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| Chemical Name |
(2R)-2-hydroxybutanedioic acid
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~745.77 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (18.64 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (18.64 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (18.64 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 7.4577 mL | 37.2884 mL | 74.5768 mL | |
| 5 mM | 1.4915 mL | 7.4577 mL | 14.9154 mL | |
| 10 mM | 0.7458 mL | 3.7288 mL | 7.4577 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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