Malic Acid

Base Information

• Chemical Name: Malic Acid
• CAS No.: 6915-15-7
• Deprecated CAS: 41308-42-3,617-48-1,623158-98-5,879715-44-3,1334703-48-8,1334703-48-8,617-48-1,879715-44-3
• Molecular Formula: C₄H₆O₅
• Molecular Weight: 134.089
• Hs Code.: H6O5 MOL WT. 134.09
• European Community (EC) Number: 230-022-8, 210-514-9, 202-601-5,210-514-9,690-607-2
• NSC Number: 25941
• UNII: 817L1N4CKP
• DSSTox Substance ID: DTXSID0027640
• Nikkaji Number: J3.091K
• Wikipedia: Malic_acid
• Wikidata: Q190143
• NCI Thesaurus Code: C80654
• RXCUI: 29209
• Metabolomics Workbench ID: 123508
• ChEMBL ID: CHEMBL1455497
• Mol file: 6915-15-7.mol

Synonyms:calcium (hydroxy-1-malate) hexahydrate;malate;malic acid;malic acid, (R)-isomer;malic acid, calcium salt, (1:1), (S)-isomer;malic acid, disodium salt;malic acid, disodium salt, (R)-isomer;malic acid, disodium salt, (S)-isomer;malic acid, magnesium salt (2:1);malic acid, monopotassium salt, (+-)-isomer;malic acid, potassium salt, (R)-isomer;malic acid, sodium salt, (+-)-isomer

Chemical Property of Malic Acid

Chemical Property:

• Appearance/Colour: White to nearly white crystals or crystal powder
• Vapor Pressure: <0.1 mm Hg ( 20 °C)
• Melting Point: 131-133 °C(lit.)
• Refractive Index: 1.3920 (estimate)
• Boiling Point: 306.4 °C at 760 mmHg
• PKA: 3.4(at 25℃)
• Flash Point: 153.4 °C
• PSA: 94.83000
• Density: 1.641 g/cm³
• LogP: -1.09340
• Storage Temp.: 2-8°C
• Solubility.: methanol: 0.1 g/mL, clear, colorless
• Water Solubility.: 558 g/L (20 ºC)
• XLogP3: -1.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 134.02152329
• Heavy Atom Count: 9
• Complexity: 129

Purity/Quality:

99% ^*data from raw suppliers

DL-Malic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-37/38-41-36/37/38-42/43-34
• Safety Statements: 26-39-37/39-36-36/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: C(C(C(=O)O)O)C(=O)O
• Recent ClinicalTrials: Malic Acid in Treatment of Xerostomia
• Recent EU Clinical Trials: Sympthomatic and prophylactic treatment of drug induced oral dryness in elderly patients with high drug consumption.
• Recent NIPH Clinical Trials: Effect of supplements containing malic acid and magnesium oxide on sleeping - a parallel randomized trial-.
• Description: Malic acid, an organic acid rich in nature, is of excellent chelating ability. It's molecule contains two carboxyl bridging groups and one hydroxyl, which can serve as ligand to coordinate with metal ions to form stable complex. In nature, malic acid can be found in three forms, namely D-malic acid, L-malic acid and the mixture DL-malic acid. However, with respect to preparation, DL-malic acid can be synthesized through industrial synthesis with a low cost, which makes it suitable for large-scale industrial application.^[2]; Malic acid is recognized for its potential to become a crucial platform chemical in a post-fossil fuel era, being identified as one of the 12 most important platform chemicals from biomass by the US Department of Energy in 2004.^[1]
• Production Methods: Occurrence and Natural Production: ; Malic acid is naturally found in various fruits, being the predominant organic acid in apples, bananas, litchis, and plums, among others. It is an intermediate in the tricarboxylic acid cycle (TCA) and can be naturally accumulated by microorganisms and plants.; ; Production from Fossil Resources: ; Currently, most malic acid is produced from fossil resources through chemical synthesis, resulting in racemic dl-malic acid. The dominant method involves the conversion of maleic anhydride, which is produced from hydrocarbons like n-butane.; ; Biotechnological Production: ; There is a significant interest in producing L-malic acid, the physiologically active form, through biotechnological methods. This approach has the advantage of producing enantiopure L-malic acid, which is preferred for certain applications over the racemic mixture. Microbial fermentation is a key method being explored for L-malic acid production. ^[1]
• Uses: The primary use of malic acid is in the food and beverage industry, where it serves as an acidulant and taste enhancer. It is also used in personal care and cleaning products as a buffering and chelating agent, in pharmaceuticals (e.g., as a component of migraine drugs), and as a material in semiconductor fabrication and animal feed additives. ^[1]; Malic acid, specifically bio-fermented malic acid (BFMA), has a strong antioxidant capacity, which can be beneficial for the health of broilers. It can potentially reduce oxidative stress and enhance the overall well-being of the animals. It is used as a feed additive to promote the health, performance, and meat quality of broilers.^[3]; Beyond it's traditional uses, malic acid is eyed for its role in low transition temperature mixtures and polymer production. Its dicarboxylic nature makes it a suitable building block for synthesizing various polymers with tailored hydrophobic/hydrophilic properties. Specific examples include its use in nanoparticles for stem cell labeling and as an enteric coating material. ^[1]
• Market and Production Capacity: The global production capacity for malic acid is between 80,000 and 100,000 tons per year, with the market volume ranging between 60,000 and 200,000 tons per year. ; Major malic acid manufacturers include Bartek, Fuso Chemical, Mitsubishi Corporation Life Sciences, Isegen, Polynt, Thirumalai Chemicals, Changmao Biochemical Engineering Company, Anhui Sealong Biotechnology, Jinhu Lile Biotechnology Industry, Tate & Lyle and Yongsan Chemicals, etc.
• References: [1] Malic acid production from renewables: a review (DOI 10.1002/jctb.6269); [2] Study on the characteristics and mechanism of DL-malic acid in inhibiting spontaneous combustion of lignite and bituminous coal (DOI 10.1016/j.fuel.2021.122012); [3] Bio-Fermented Malic Acid Facilitates the Production of High-Quality Chicken via Enhancing Muscle Antioxidant Capacity of Broilers (DOI 10.3390/antiox11122309)

Technology Process of Malic Acid

There total 2 articles about Malic Acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(S)-1-(4-Isopropyl-phenyl)-ethylamine; compound with 2-hydroxy-succinic acid (98571-19-8,98571-20-1) → L-(-)-malic acid (97-67-6,617-48-1,636-61-3,6915-15-7,78644-42-5)

Guidance literature:

With sodium hydroxide; Amberlite 120B;

DOI:10.1055/s-1985-31162

Reference yield:

(S)-1-(4-Isopropyl-phenyl)-ethylamine; compound with 2-hydroxy-succinic acid (98571-19-8,98571-20-1) → (+)-Malic acid (97-67-6,617-48-1,636-61-3,6915-15-7,78644-42-5)

Guidance literature:

With sodium hydroxide; Amberlite 120B;

DOI:10.1055/s-1985-31162

Reference yield:

(+)-Malic acid (97-67-6,617-48-1,636-61-3,6915-15-7,78644-42-5) → α-malate radical (15906-66-8,78644-42-5)

Guidance literature:

With water; dinitrogen monoxide; at 25.1 ℃; Irradiation;

upstream raw materials:

(S)-1-(4-Isopropyl-phenyl)-ethylamine; compound with 2-hydroxy-succinic acid

Downstream raw materials:

α-malate radical

Refernces