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Malic acid is an organic compound with the molecular formula C₄H₆O₅. It is a dicarboxylic acid that is made by all living organisms, contributes to the pleasantly 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 an intermediate in the citric acid cycle.

Biochemistry

L-Malic acid is the naturally occurring form, whereas a mixture of L- and D-malic acid is produced synthetically.

L-Malic acid
D-Malic acid

Malate plays an important role in biochemistry. In the C4 carbon fixation process, malate is a source of CO₂ in the Calvin cycle. In the citric acid cycle, (S)-malate is an intermediate, formed by the addition of an -OH group on the si face of fumarate. It can also be formed from pyruvate via anaplerotic reactions.

Malate is also synthesized by the carboxylation of phosphoenolpyruvate in the guard cells of plant leaves. Malate, as a double anion, often accompanies potassium cations during the uptake of solutes into the guard cells in order to maintain electrical balance in the cell. The accumulation of these solutes within the guard cell decreases the solute potential, allowing water to enter the cell and promote aperture of the stomata.

Malic acid in food

Malic acid was first isolated from apple juice by Carl Wilhelm Scheele in 1785.^[3] Antoine Lavoisier in 1787 proposed the name acide malique which is derived from the Latin word for apple, mālum.^[4]^[5] In German it is named Äpfelsäure (or Apfelsäure) after plural or singular of the fruit apple, but the salt(s) Malat(e). Malic acid contributes to the sourness of green apples. It is present in grapes and in most wines with concentrations sometimes as high as 5 g/l.^[6] It confers a tart taste to wine, although the amount decreases with increasing fruit ripeness. The taste of malic acid is very clear and pure in rhubarb, a plant for which it is the primary flavor. It is also a component of some artificial vinegar flavors, such as "Salt and Vinegar" flavored potato chips.^[7]

The process of malolactic fermentation converts malic acid to much milder lactic acid. Malic acid occurs naturally in all fruits and many vegetables, and is generated in fruit metabolism.^[8]

Malic acid, when added to food products, is denoted by E number E296. Malic acid is the source of extreme tartness in USA-produced confectionery, the so-called extreme candy. It is also used with or in place of the less sour citric acid in sour sweets. These sweets are sometimes labeled with a warning stating that excessive consumption can cause irritation of the mouth. It is approved for use as a food additive in the EU,^[9] USA^[10] and Australia and New Zealand^[11] (where it is listed by its INS number 296).

Malic acid provides 10 kJ of energy per gram during digestion.^[12]

Production and main reactions

Racemic malic acid is produced industrially by the double hydration of maleic anhydride. In 2000, American production capacity was 5000 tons per year. Both enantiomers may be separated by chiral resolution of the racemic mixture, and the (S)- enantiomer may be specifically obtained by fermentation of fumaric acid.^[13]

Self-condensation of malic acid with fuming sulfuric acid gives the pyrone coumalic acid:^[14]

Malic acid was important in the discovery of the Walden inversion and the Walden cycle, in which (−)-malic acid first is converted into (+)-chlorosuccinic acid by action of phosphorus pentachloride. Wet silver oxide then converts the chlorine compound to (+)-malic acid, which then reacts with PCl₅ to the (−)-chlorosuccinic acid. The cycle is completed when silver oxide takes this compound back to (−)-malic acid.

Interactive pathway map

Click on genes, proteins and metabolites below to link to respective articles. ^{[§ 1]}

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|{{{bSize}}}px|alt=Glycolysis and Gluconeogenesis edit]]

File:WP534.png

Glycolysis and Gluconeogenesis edit

^ The interactive pathway map can be edited at WikiPathways: "GlycolysisGluconeogenesis_WP534".

Click on genes, proteins and metabolites below to link to respective articles. ^{[§ 1]}

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|{{{bSize}}}px|alt=TCA Cycle edit]]

File:TCACycle WP78.png

TCA Cycle edit

^ The interactive pathway map can be edited at WikiPathways: "TCACycle_WP78".

References

^ "chemBlink Database of Chemicals from Around the World". chemblink.com.
^ Dawson, R. M. C. et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.
^ Carl Wilhelm Scheele (1785) "Om Frukt- och Bår-syran" (On fruit and berry acid), Kongliga Vetenskaps Academiens Nya Handlingar (New Proceedings of the Royal Academy of Science), 6 : 17-27. From page 21: " … vil jag hådanefter kalla den Åple-syran." ( … I will henceforth call it apple acid.)
^ de Morveau, Lavoisier, Bertholet, and de Fourcroy, Méthode de Nomenclature Chimique (Paris, France: Cuchet, 1787), p. 108.
^ The Origin of the Names Malic, Maleic, and Malonic Acid Jensen, William B. J. Chem. Educ. 2007, 84, 924. Abstract
^ "Methods For Analysis of Musts and Wines", Ough and Amerine, John Wiley and Sons, 2nd Edition, 1988, page 67
^ "The Science Behind Salt and Vinegar Chips". seriouseats.com.
^ Malic Acid, Bartek Ingredients (retrieved 2 February 2012)
^ UK Food Standards Agency: "Current EU approved additives and their E Numbers". Retrieved 2011-10-27.
^ US Food and Drug Administration: "Listing of Food Additives Status Part II". Retrieved 2011-10-27.
^ Australia New Zealand Food Standards Code"Standard 1.2.4 - Labelling of ingredients". Retrieved 2011-10-27.
^ Greenfield, Heather; Southgate, D.A.T. (2003). Food composition data: production, management and use (2 ed.). Rome: Food and Agriculture Organization of the United Nations. p. 146. ISBN 9789251049495. Retrieved 10 February 2014.
^ Karlheinz Miltenberge (2005), "Hydroxycarboxylic Acids, Aliphatic", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a13_507
^ Richard H. Wiley and Newton R. Smith (1963). "Coumalic acid". Org. Synth. ; Coll. Vol. 4, p. 201

External links

Malic acid MS Spectrum
Calculator: Water and solute activities in aqueous malic acid

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Food chemistry.Food Chem.2015 Nov 15;187:563-71. doi: 10.1016/j.foodchem.2015.04.002. Epub 2015 Apr 7.
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Chiral ligand-exchange separation and determination of malic acid enantiomers in apple juice by open-tubular capillary electrochromatography.

Aydoğan C1, Karakoç V2, Denizli A2.
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This study describes the application of an open tubular capillary column for chiral ligand-exchange separation and determination of malic acid enantiomers in apple juice by open-tubular capillary electrochromatography (OT-CEC). The open tubular column was prepared by in-situ grafting polymerization
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Enhancement of malate-production and increase in sensitivity to dimethyl succinate by mutation of the VID24 gene in Saccharomyces cerevisiae

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Properties of Geobacillus stearothermophilus malate dehydrogenase used as a diagnostic reagent and its characterization by molecular modeling

International journal of analytical bio-science 4(2), 21-27, 2016-06
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リンゴ酸生産能の増強を目的とした耐熱性マリックエンザイムの改変(2015生物工学論文賞)

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NAID 110010039561

「解糖系」

Malic acid
	; DL-Malic acid
Names
	IUPAC name 2-hydroxybutanedioic acid
	Other names L-Malic acid; D-Malic acid; (–)-Malic acid; (+)-Malic acid; (S)-Hydroxybutanedioic acid; (R)-Hydroxybutanedioic acid
Identifiers
CAS Registry Number	617-48-1 ; 6915-15-7
ChEBI	CHEBI:6650
ChEMBL	ChEMBL1455497
ChemSpider	510 ; 83793 D-(+)-malic acid ; 193317 L-(–)-malic acid
EC number	230-022-8
	InChI InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9) ; Key: BJEPYKJPYRNKOW-UHFFFAOYSA-N ; InChI=1/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9); Key: BJEPYKJPYRNKOW-UHFFFAOYAM ;
IUPHAR/BPS	2480
Jmol-3D images	Image
KEGG	C00149
PubChem	525
	SMILES O=C(O)CC(O)C(=O)O ;
UNII	817L1N4CKP
Properties
Chemical formula	C4H6O5
Molar mass	134.09 g·mol−1
Density	1.609 g cm−3
Melting point	130 °C (266 °F; 403 K)
Solubility in water	558 g/L (at 20 °C)
Acidity (pKa)	pKa1 = 3.40, pKa2 = 5.20
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).
	verify (what is: /?)
	Infobox references

　　[★]

英: glycolytic pathway
同: エムデン-マイヤーホフ経路 Embden-Meyerhof pathway
関: 解糖、TCA回路

CH(OH)-CH(OH)-C(OH)H-CH(OH)-C(CH2OH)H-O- グルコース (OHが↓↓↑↓↑)
CH(OH)-CH(OH)-C(OH)H-CH(OH)-C(CH2O-PO3)H-O- グルコース-6-リン酸 (OHが↓↓↑↓↑)
C(CH2OH)OH-C(OH)H-CH(OH)-C(CH2O-PO3)H-O- フルクトース-6-リン酸
C(CH2O-PO3)OH-C(OH)H-CH(OH)-C(CH2O-PO3)H-O- フルクトース-1,6-リン酸

glucose
↓-hexokinase/glucokinase(liver)
glucose 6-phosphate
↓-phosphohexose isomerase
fructose 6-phosphate
↓-phosphofructokinase
fructose 1,6-bisphosphate
↓-aldolase
glyceraldehyde 3-phosphate
↓-glyceraldehyde-3-phosphate dehydrogenase
1,3-bisphosphoglycerate
↓-phosphoglycerate kinase →ATP
3-phosphoglycerate
↓-phosphoglyceate mutase
2-phosphoglycerate
↓-enolase
phosphoenolpyruvate
↓-pyruvate kinase → ATP
pyruvate
　－(pyruvate dehydrogenase)→acetyl-CoA
　－(pyruvate carboxylase)→oxaloacetate－(NADH+H+)→malate

解糖系の酵素 (first aid step1 2006 p.87, FASTEP1_87_酵素一覧.xls)

1	galactokinase	キナーゼ
2	galactose-1-phosphate uridyltransferase	転移酵素
3	hexokinase/glucokinase	キナーゼ
4	glucose-6-phosphatase	ホスファターゼ
5	glucose-6-phosphate dehydrogenase	脱水素酵素
6	transketolase
7	phosphofructokinase	キナーゼ
8	fructose-1,6-bisphosphatase	ホスファターゼ
9	fructokinase	キナーゼ	フルクトキナーゼ
10	aldolase B		アルドラーゼ
11	pyruvate kinase	キナーゼ	ピルビン酸キナーゼ
12	pyruvate dehydrogenase	脱水素酵素	ピルビン酸デヒドロゲナーゼ
13	HMG-CoA reductase	還元酵素	HMG-CoA還元酵素
14	pyruvate carboxylase	カルボキシラーゼ	ピルビン酸カルボキシラーゼ
15	PEP carboxykinase	キナーゼ	PEPカルボキシキナーゼ
16	citrate synthase	合成酵素	クエン酸合成酵素
17	α-ketoglutarate dehydrogenase	脱水素酵素	α-ケトグルタミン酸脱水素酵素
18	ornithine transcarbamylase	転移酵素	オルニチンカルバモイルトランスフェラーゼ

「リンゴ酸塩」

　　[★]

英: malate
関: リンゴ酸、リンゴ酸エステル

「リンゴ酸エステル」

　　[★]

英: malate
関: リンゴ酸、リンゴ酸塩

「リンゴ酸」

　　[★]

malic
英: malate malic acid
関

「2-isopropylmalate synthase」

　　[★]

2-イソプロピルリンゴ酸合成酵素、2-イソプロピルリンゴ酸シンターゼ

「thiethylperazine malate」

　　[★]

リンゴ酸チエチルペラジン

関: thiethylperazine、thiethylperazine maleate

「malate dehydrogenase」

　　[★]

リンゴ酸脱水素酵素、リンゴ酸デヒドロゲナーゼ

[WikiPathways-15] The interactive pathway map can be edited at WikiPathways: "GlycolysisGluconeogenesis_WP534".

[WikiPathways-16] The interactive pathway map can be edited at WikiPathways: "TCACycle_WP78".

[1] "chemBlink Database of Chemicals from Around the World". chemblink.com.

[2] Dawson, R. M. C. et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.

[3] Carl Wilhelm Scheele (1785) "Om Frukt- och Bår-syran" (On fruit and berry acid), Kongliga Vetenskaps Academiens Nya Handlingar (New Proceedings of the Royal Academy of Science), 6 : 17-27. From page 21: " … vil jag hådanefter kalla den Åple-syran." ( … I will henceforth call it apple acid.)

[4] Morveau, Lavoisier, Bertholet, and de Fourcroy, Méthode de Nomenclature Chimique (Paris, France: Cuchet, 1787), p. 108.

[5] The Origin of the Names Malic, Maleic, and Malonic Acid Jensen, William B. J. Chem. Educ. 2007, 84, 924. Abstract

[6] "Methods For Analysis of Musts and Wines", Ough and Amerine, John Wiley and Sons, 2nd Edition, 1988, page 67

[7] "The Science Behind Salt and Vinegar Chips". seriouseats.com.

[8] Malic Acid, Bartek Ingredients (retrieved 2 February 2012)

[9] UK Food Standards Agency: "Current EU approved additives and their E Numbers". Retrieved 2011-10-27.

[10] US Food and Drug Administration: "Listing of Food Additives Status Part II". Retrieved 2011-10-27.

[11] Australia New Zealand Food Standards Code"Standard 1.2.4 - Labelling of ingredients". Retrieved 2011-10-27.

[FAO-12] Greenfield, Heather; Southgate, D.A.T. (2003). Food composition data: production, management and use (2 ed.). Rome: Food and Agriculture Organization of the United Nations. p. 146. ISBN 9789251049495. Retrieved 10 February 2014.

[13] Karlheinz Miltenberge (2005), "Hydroxycarboxylic Acids, Aliphatic", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a13_507

[14] Richard H. Wiley and Newton R. Smith (1963). "Coumalic acid". Org. Synth. ; Coll. Vol. 4, p. 201

リンク元	「解糖系」「リンゴ酸塩」「リンゴ酸エステル」「リンゴ酸」
拡張検索	「2-isopropylmalate synthase」「thiethylperazine malate」「malate dehydrogenase」

匿名

検索

案内

案内

malate