WordNet

street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
having the characteristics of an acid; "an acid reaction"

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酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/01/03 11:00:26」(JST)

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Not to be confused with maleic acid or malonic acid.

"Malate" redirects here. For the district in Manila, see Malate, Manila.

Malic acid is an organic compound with the formula HO₂CCH₂CHOHCO₂H. 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[edit]

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[edit]

Malic acid was first isolated from apple juice by Carl Wilhelm Scheele in 1785. Antoine Lavoisier in 1787 proposed the name acide malique which is derived from the Latin word for apple, mālum.^[3] 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.^[4] 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.

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.^[5]

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,^[6] USA^[7] and Australia and New Zealand^[8] (where it is listed by its INS number 296).

Production and main reactions[edit]

Racemic malic acid is produced industrially by the double hydration of maleic anhydride. In 2000, American production capacity was 5000 tonnes 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.^[9]

Self-condensation of malic acid with fuming sulfuric acid gives the pyrone coumalic acid:^[10]

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[edit]

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

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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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TCA Cycle edit

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

References[edit]

^ chemBlink Online Database of Chemicals from Around the World
^ Dawson, R. M. C. et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.
^ 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
^ 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.
^ 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: 201

External links[edit]

Calculator: Water and solute activities in aqueous malic acid

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. シェーグレン症候群における口内乾燥およびその他の非眼結膜炎症状の治療 treatment of dry mouth and other non ocular sicca symptoms in sjogrens syndrome
2. 小児のための菜食料理 vegetarian diets for children

English Journal

Physicochemical characterization of pomegranate wines fermented with three different Saccharomyces cerevisiae yeast strains.

Berenguer M1, Vegara S1, Barrajón E1, Saura D1, Valero M1, Martí N2.
Food chemistry.Food Chem.2016 Jan 1;190:848-55. doi: 10.1016/j.foodchem.2015.06.027. Epub 2015 Jun 10.
Three commercial Saccharomyces cerevisiae yeast strains: Viniferm Revelación, Viniferm SV and Viniferm PDM were evaluated for the production of pomegranate wine from a juice coupage of the two well-known varieties Mollar and Wonderfull. Further malolactic fermentation was carried out spontaneously.
PMID 26213048

A rapid qualitative and quantitative evaluation of grape berries at various stages of development using Fourier-transform infrared spectroscopy and multivariate data analysis.

Musingarabwi DM1, Nieuwoudt HH1, Young PR1, Eyéghè-Bickong HA1, Vivier MA2.
Food chemistry.Food Chem.2016 Jan 1;190:253-62. doi: 10.1016/j.foodchem.2015.05.080. Epub 2015 May 18.
Fourier transform (FT) near-infrared (NIR) and attenuated total reflection (ATR) FT mid-infrared (MIR) spectroscopy were used to qualitatively and quantitatively analyse Vitis vinifera L. cv Sauvignon blanc grape berries. FT-NIR and ATR FT-MIR spectroscopy, coupled with spectral preprocessing and mu
PMID 26212968

Chiral ligand-exchange separation and determination of malic acid enantiomers in apple juice by open-tubular capillary electrochromatography.

Aydoğan C1, Karakoç V2, Denizli A2.
Food chemistry.Food Chem.2015 Nov 15;187:130-4. doi: 10.1016/j.foodchem.2015.04.062. Epub 2015 Apr 22.
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
PMID 25977007

Japanese Journal

Growth behavior of anodic porous alumina formed in malic acid solution

Kikuchi Tatsuya,Yamamoto Tsuyoshi,Suzuki Ryosuke O.
Applied Surface Science 284, 907-913, 2013-11-00
… The growth behavior of anodic porous alumina formed on aluminum by anodizing in malic acid solutions was investigated. … High-purity aluminum plates were electropolished in CH3COOH/HClO4 solutions and then anodized in 0.5 M malic acid solutions at 293 K and constant cell voltages of 200–350 V. …
NAID 120005322433

紫黒米混合飯の色調と物性に与える有機酸の影響

岸本律子,長谷川悦子,中嶋加代子,森光寿,地上博子
日本調理科学会誌 46(2), 107-113, 2013-04-05
紫黒米混合飯(混合飯)の色調と物性に及ぼす有機酸の影響について検討した。白米ヒノヒカリ(H-rice)と紫黒米むらさきの舞(M-rice,搗精歩留まり90%,同95%,玄米)を重量比9:1の割合で混合し,炊飯溶液に0.2M有機酸(酢酸,乳酸,コハク酸,リンゴ酸またはクエン酸)を添加して混合飯を調製した。混合飯のL^*値は低下し,むらさきの舞の搗精歩留まりが高いものほど低下した。a^*値は添加した有 …
NAID 110009604206

有機酸および有機酸塩が昆布軟化に与える影響

山岸あづみ,青江誠一郎
International Journal of Human Culture Studies 2013(23), 176-178, 2013
昆布を各種有機酸（シュウ酸・クエン酸・乳酸・コハク酸・リンゴ酸）および有機酸塩（シュウ酸K・シュウ酸Na・クエン酸K・クエン酸Na・乳酸Na・コハク酸Na・リンゴ酸Na）溶液にて煮沸した．その結果，有機酸溶液のpHは3-4であり，有機酸塩溶液のpHは6前後であった．また，昆布は有機酸溶液ではシュウ酸溶液，有機酸塩溶液ではシュウ酸Naおよびシュウ酸K溶液と煮沸した際にもっとも軟化した．本結果から，溶 …
NAID 130003379423

Related Pictures

★リンクテーブル★

リンク元	「リンゴ酸」
関連記事	「malic」

「リンゴ酸」

Malic acid
	; DL-Malic acid
	IUPAC name hydroxybutanedioic acid
	Other names L-Malic acid; D-Malic acid; (–)-Malic acid; (+)-Malic acid; (S)-Hydroxybutanedioic acid; (R)-Hydroxybutanedioic acid
Identifiers
CAS number	6915-15-7
PubChem	525
ChemSpider	510 , 83793 D-(+)-malic acid , 193317 L-(–)-malic acid
UNII	817L1N4CKP
EC number	230-022-8
KEGG	C00149
ChEBI	CHEBI:6650
ChEMBL	CHEMBL1455497
Jmol-3D images	Image 1
	SMILES O=C(O)CC(O)C(=O)O ;
	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 ;
Properties
Molecular 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
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
	Infobox references

　　[★]

malic
英: malate malic acid
関

「malic」

　　[★]

ラテン語 malum = apple

adj.

リンゴの。(生化学)リンゴ酸の

[WikiPathways-11] The interactive pathway map can be edited at WikiPathways: "GlycolysisGluconeogenesis_WP534".

[WikiPathways-12] The interactive pathway map can be edited at WikiPathways: "TCACycle_WP78".

[1] Blink Online Database of Chemicals from Around the World

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

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

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

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

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

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

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

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

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

匿名

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案内

案内

malic acid