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Malic acid information


Malic acid
Skeletal structure
Ball-and-stick model

DL-Malic acid
Names
Preferred IUPAC name
2-Hydroxybutanedioic acid
Other names
  • Hydroxybutanedioic acid
  • 2-Hydroxysuccinic acid
  • (L/D)-Malic acid
  • (±)-Malic acid
  • (S/R)-Hydroxybutanedioic acid
Identifiers
CAS Number
  • 6915-15-7 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:6650 checkY
  • CHEBI:30796 D-(+)
  • CHEBI:30797 L-(–)
ChEMBL
  • ChEMBL1455497 ☒N
ChemSpider
  • 510 checkY
  • 83793 D-(+)-malic acid checkY
  • 193317 L-(–)-malic acid checkY
ECHA InfoCard 100.027.293 Edit this at Wikidata
EC Number
  • 230-022-8
E number E296 (preservatives)
IUPHAR/BPS
  • 2480
KEGG
  • C00711 ☒N
  • C00497 D-(+)
  • C00149 L-(–)
PubChem CID
  • 525
  • 92824 D-(+)
  • 222656 L-(–)
UNII
  • 817L1N4CKP checkY
CompTox Dashboard (EPA)
  • DTXSID0027640 Edit this at Wikidata
InChI
  • InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9) checkY
    Key: BJEPYKJPYRNKOW-UHFFFAOYSA-N checkY
  • InChI=1/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)
    Key: BJEPYKJPYRNKOW-UHFFFAOYAM
SMILES
  • O=C(O)CC(O)C(=O)O
Properties
Chemical formula
C4H6O5
Molar mass 134.09 g/mol
Appearance Colorless
Density 1.609 g⋅cm−3
Melting point 130 °C (266 °F; 403 K)
Solubility in water
558 g/L (at 20 °C)[1]
Acidity (pKa) pKa1 = 3.40
pKa2 = 5.20[2]
pKa3 = 14.5[3]
Hazards
GHS labelling:
Pictograms
GHS07: Exclamation mark
Flash point 203 °C[4]
Related compounds
Other anions
Malate
Related carboxylic acids
Succinic acid
Tartaric acid
Fumaric acid
Related compounds
Butanol
Butyraldehyde
Crotonaldehyde
Sodium malate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Malic acid is an organic compound with the molecular formula HO2CCH(OH)CH2CO2H. It is a dicarboxylic acid that is made by all living organisms, contributes to the sour taste of fruits, and is used as a food additive. Malic acid has two stereoisomeric forms (L- and D-enantiomers), though only the L-isomer exists naturally. The salts and esters of malic acid are known as malates. The malate anion is a metabolic intermediate in the citric acid cycle.

  1. ^ "chemBlink Database of Chemicals from Around the World". chemblink.com. Archived from the original on 2009-01-22.
  2. ^ Data for biochemical research (3rd ed.). Oxford: Clarendon Press. 1986. ISBN 0-19-855358-7. OCLC 11865673.
  3. ^ Silva, Andre M. N.; Kong, Xiaole; Hider, Robert C. (2009). "Determination of the pKa value of the hydroxyl group in the α-hydroxycarboxylates citrate, malate and lactate by 13C NMR: implications for metal coordination in biological systems". BioMetals. 22 (5): 771–778. doi:10.1007/s10534-009-9224-5. ISSN 0966-0844. PMID 19288211.
  4. ^ "DL-Malic acid - (DL-Malic acid) SDS". Merck Millipore.

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Malic acid

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converts malic acid to much milder lactic acid. Malic acid occurs naturally in all fruits and many vegetables, and is generated in fruit metabolism. Malic acid...

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Maleic acid

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practised commercially, maleic acid can be converted into maleic anhydride by dehydration, to malic acid by hydration, and to succinic acid by hydrogenation...

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Acids in wine

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stronger malic acid into the softer lactic acid; formally, malic acid is polyprotic (contributes multiple protons, here two), while lactic acid is monoprotic...

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Malolactic fermentation

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converting the "harsher" diprotic malic acid to the softer monoprotic lactic acid. The different structures of malic and lactic acids leads to a reduction of titratable...

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Crassulacean acid metabolism

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to diffuse into the mesophyll cells. The CO2 is stored as four-carbon malic acid in vacuoles at night, and then in the daytime, the malate is transported...

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Tartaric acid

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co-catalyst in asymmetric synthesis. Tartaric acid is a muscle toxin, which works by inhibiting the production of malic acid, and in high doses causes paralysis...

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Organic acid

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organic acids. A few common examples include: Lactic acid Acetic acid Formic acid Citric acid Oxalic acid Uric acid Malic acid Tartaric acid Butyric acid Folic...

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Acidulant

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acetic acid (e.g. in pickles) and citric acid. Many beverages, such as colas, contain phosphoric acid. Sour candies often are formulated with malic acid. Other...

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Malonic acid

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in 1858 by the French chemist Victor Dessaignes via the oxidation of malic acid. The structure has been determined by X-ray crystallography and extensive...

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Citramalic acid

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Citramalic acid is the organic compound with the formula HO2CCH2C(CH3)(OH)CO2H. A chiral compound, it is related structurally to malic acid. Citramalic acid is...

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Fumaric acid

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~1.5 g of citric acid, in order to add sourness, similarly to the way malic acid is used. As well as being a component of some artificial vinegar flavors...

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Lactic acid bacteria

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transformation of L-malic acid (dicarboxylic acid) to an lactic acid (monocarboxylic acid). This change occurs due to the presence of malolactic and malic enzymes...

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Asparagine

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treated asparagine with nitrous acid, which removed the molecule's amine (–NH2) groups and transformed asparagine into malic acid. This revealed the molecule's...

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Magnesium malate

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Magnesium malate, the magnesium salt of malic acid, is a mineral supplement often used for nutritional concerns. It is represented by the chemical formula...

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Apple cider vinegar

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converted into acetic acid by acetic acid-forming bacteria (Acetobacter species), yielding cider vinegar. Acetic acid and malic acid combine to give this...

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Isocitric acid

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Citric acid Tartaric acid Malic acid Kamzolova, Svetlana V.; Morgunov, Igor G. (2019-12-01). "Microbial production of (2R,3S)-isocitric acid: state of...

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Lactic acid

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present malic acid to lactic acid, to reduce the sharpness and for other flavor-related reasons. This malolactic fermentation is undertaken by lactic acid bacteria...

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Oxidative decarboxylation

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by dehydrogenation of hydroxyl carboxylic acids such as carbonyl carboxylic acid, malic acid, isocitric acid, etc. Pyruvate catalytic reaction catalyzed...

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Veraison

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decreases due to degradation of malic acid. The degradation of malic acid during ripening makes tartaric acid the predominant acid; grape berries also possess...

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Maleic anhydride

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Maleic anhydride is an organic compound with the formula C2H2(CO)2O. It is the acid anhydride of maleic acid. It is a colorless or white solid with an...

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Jolly Rancher

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added to individual batches of syrup solution which are later mixed with malic acid to improve shelf life and add further flavor. Once the mixture begins...

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Thiomalic acid

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(SH) in place of the hydroxy group (OH) in malic acid. Salts and esters are known as thiomalates. Thiomalic acid is an intermediate in the synthesis of corrosion...

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Walden inversion

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cycle which went like this: (+) chlorosuccinic acid (1 in the illustration) was converted to (+) malic acid 2 by action of silver oxide in water with retention...

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Malic

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Malic can refer to: Malíč, village in the Czech Republic. Malič, mountain in Serbia Malic acid, an organic compound Gruban Malić, a fictional character...

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Calcium citrate malate

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water-soluble calcium supplement. It is the calcium salt of citric acid and malic acid with variable composition. Calcium citrate malate's bioavailability...

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Sorbic acid

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Bedeutung gewinnt." (For the crystalline acid, I suggest the name "sorbic acid", whereby an old name of the malic acid that's found in rowan berries gains...

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List of carboxylic acids

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Carboxylic acids are organic acids characterized by a carboxyl (-COOH) functional group. The naming of these compounds is governed by IUPAC nomenclature...

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