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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
2887:
2810:
2736:
2848:
2936:
1878:
1416:
2109:
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".
2857:
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2745:
3047:
695:
1951:
1489:
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Rosskopf, Erin; Di Gioia, Francesco; Hong, Jason C.; Pisani, Cristina; Kokalis-Burelle, Nancy (2020-08-25). "Organic
Amendments for Pathogen and Nematode Control".
1225:
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
1953:
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to the (â)-chlorosuccinic acid. The cycle is completed when silver oxide takes this compound back to (â)-malic acid.
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1195:, a plant for which it is the primary flavor. It is also the compound responsible for the tart flavor of
480:
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2017:
1214:. Malic acid occurs naturally in all fruits and many vegetables, and is generated in fruit metabolism.
714:
647:
3164:
1380:
311:
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44:
1183:
and in most wines with concentrations sometimes as high as 5 g/L. It confers a tart taste to
1002:
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1207:
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that is made by all living organisms, contributes to the sour taste of fruits, and is used as a
3159:
2905:
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2296:
2196:
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707:
1127:) after plural or singular of a sour thing from the apple fruit, but the salt(s) are called
276:
2258:
1379:
increases microbial synthesis of malic acid. This is thought to occur naturally as part of
1274:
1084:
468:
264:
82:
2469:(2 ed.). Rome: Food and Agriculture Organization of the United Nations. p. 146.
149:
8:
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1067:
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139:
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200:
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1340:, in which (â)-malic acid first is converted into (+)-chlorosuccinic acid by action of
1119:
1025:
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193:
2651:
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then converts the chlorine compound to (+)-malic acid, which then reacts with PCl
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1973:
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Click on genes, proteins and metabolites below to link to respective articles.
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2012:
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Malic acid contains 10 kJ (2.39 kilocalories) of energy per gram.
1230:
1229:
in the EU, US and
Australia and New Zealand (where it is listed by its
1176:
942:, which includes all apples and crabapples; and is the origin of other
597:
345:
312:
248:
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1251:. In 2000, American production capacity was 5,000 tons per year. The
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800:
Except where otherwise noted, data are given for materials in their
2802:
2708:
1376:
1218:
1144:
394:
382:
375:
329:
1171:, and is present in lower concentrations in other fruits, such as
969:-Malic acid is the naturally occurring form, whereas a mixture of
172:
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2847:
2531:
1244:
1200:
1192:
1132:
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malic acid is produced industrially by the double hydration of
1168:
955:
745:
228:
2647:
Calculator: Water and solute activities in aqueous malic acid
2497:
Karlheinz
Miltenberge. "Hydroxycarboxylic Acids, Aliphatic".
1221:
E296. It is sometimes used with or in place of the less sour
1196:
1180:
1156:
1148:
1113:
1108:
1098:
1071:
water to enter the cell and promote aperture of the stomata.
938:
905:
897:
184:
162:
485:
2532:
Richard H. Wiley, Newton R. Smith (1951). "Coumalic acid".
2462:
1992:
The interactive pathway map can be edited at WikiPathways:
1388:
1203:
flavors, such as "salt and vinegar" flavored potato chips.
1184:
1164:
1160:
525:
InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)
366:
2585:
1055:
face of fumarate. It can also be formed from pyruvate via
1047:)-malate is an intermediate, formed by the addition of an
535:
InChI=1/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)
2408:
2247:"The Origin of the Names Malic, Maleic, and Malonic Acid"
936:, meaning 'apple tree', is used as the name of the genus
739:
30:"Malate" redirects here. For the district in Manila, see
1131:. Malic acid is the main acid in many fruits, including
2681:
2559:
A. W. Ingersoll (1937). "D- and l-α-Phenylethylamine".
2054:"chemBlink Database of Chemicals from Around the World"
1217:
Malic acid, when added to food products, is denoted by
1179:
contain high proportions of the acid. It is present in
2466:
Food composition data: production, management and use
330:
1191:. The taste of malic acid is very clear and pure in
2579:
2396:"Current EU approved additives and their E Numbers"
2228:de Morveau, Lavoisier, Bertholet, and de Fourcroy,
2203:(New Proceedings of the Royal Academy of Science),
354:
2496:
1332:Malic acid was important in the discovery of the
1199:spice. It is also a component of some artificial
1175:It contributes to the sourness of unripe apples.
3121:
2324:(2nd ed.). New York: J. Wiley. p. 67.
1367:, a versatile resolving agent in its own right.
1239:
442:
430:
423:
2558:
2463:Greenfield, Heather; Southgate, D.A.T. (2003).
2080:(3rd ed.). Oxford: Clarendon Press. 1986.
1880:
1418:
148:
16:Dicarboxylic acid responsible for apple acidity
2500:Ullmann's Encyclopedia of Industrial Chemistry
2173:"Peffley: Crabapples steal the show in autumn"
2108:
1329:and water are liberated during this reaction.
2667:
2201:Kongliga Vetenskaps Academiens Nya Handlingar
1187:; the amount decreases with increasing fruit
1986:
2443:"Standard 1.2.4 - Labelling of ingredients"
2354:"The Science Behind Salt and Vinegar Chips"
1263:-Malic acid is obtained by fermentation of
931:
925:
2674:
2660:
1394:
930:, meaning 'apple'. The related Latin word
500:
302:
275:
263:
256:
2440:Australia New Zealand Food Standards Code
467:
2301:Wissenschaft Online Lexikon der Biologie
2321:Methods for analysis of musts and wines
2035:, resulting from malic acid dehydration
977:-malic acid is produced synthetically.
924:The word 'malic' is derived from Latin
496:
3122:
2244:
630:130 °C (266 °F; 403 K)
293:
2655:
2154:"DL-Malic acid - (DL-Malic acid) SDS"
1963:|alt=Glycolysis and Gluconeogenesis
528:Key: BJEPYKJPYRNKOW-UHFFFAOYSA-N
236:
211:
199:
192:
2317:
2606:10.1146/annurev-phyto-080516-035608
2456:
2209:" ... vil jag hÄdanefter kalla den
2170:
1381:soil microbe suppression of disease
1210:converts malic acid to much milder
1079:Malic acid was first isolated from
538:Key: BJEPYKJPYRNKOW-UHFFFAOYAM
414:
393:
381:
374:
13:
2307:from the original on May 15, 2016.
1876:
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1509:
1504:
1499:
1414:
1062:Malate is also synthesized by the
1020:Malate plays an important role in
14:
3186:
2640:
1995:"GlycolysisGluconeogenesis_WP534"
1273:of malic acid in the presence of
3094:
3084:
3056:
3046:
3017:
3007:
2975:
2965:
2934:
2904:
2897:
2885:
2856:
2846:
2818:
2808:
2779:
2769:
2744:
2734:
2707:
2245:Jensen, William B. (June 2007).
2232:(Paris, France: Cuchet, 1787),
2230:MĂ©thode de Nomenclature Chimique
2215:( ... I will henceforth call it
2207: : 17-27. From page 21:
1976:Glycolysis and Gluconeogenesis
1370:
1001:
982:
808:
713:
61:
52:
43:
2589:Annual Review of Phytopathology
2552:
2525:
2490:
2434:
2387:
2364:
2346:
2311:
1387:with molasses can be used as a
1028:process, malate is a source of
961:
888:-enantiomers), though only the
804:(at 25 °C , 100 kPa).
2285:
2238:
2222:
2189:
2164:
2146:
2068:
2046:
892:-isomer exists naturally. The
1:
2251:Journal of Chemical Education
2077:Data for biochemical research
2039:
1240:Production and main reactions
642:558 g/L (at 20 °C)
123:(S/R)-Hydroxybutanedioic acid
2195:Carl Wilhelm Scheele (1785)
2023:Crassulacean acid metabolism
1097:, which is derived from the
919:
7:
3135:Citric acid cycle compounds
2416:"Food Additive Status List"
2384:(retrieved 2 February 2012)
2199:(On fruit and berry acid),
2006:
1391:treatment in horticulture.
900:of malic acid are known as
10:
3191:
2393:UK Food Standards Agency:
1375:Soil supplementation with
1091:in 1787 proposed the name
1074:
602:134.09 g/mol
29:
18:
2930:
2903:
2896:
2723:
2697:
2692:
2197:"Om Frukt- och BĂ„r-syran"
2177:Lubbock Avalanche-Journal
2124:10.1007/s10534-009-9224-5
798:
731:
694:
689:
567:
547:
512:
132:
93:
87:2-Hydroxybutanedioic acid
81:
76:
60:
51:
42:
2573:10.15227/orgsyn.017.0080
2546:10.15227/orgsyn.031.0023
2509:10.1002/14356007.a13_507
2028:Malateâaspartate shuttle
1342:phosphorus pentachloride
1259:of the racemic mixture.
1117:. In German it is named
946:classifications such as
19:Not to be confused with
3175:Metabolic intermediates
3150:Food acidity regulators
2503:. Weinheim: Wiley-VCH.
1395:Interactive pathway map
1360:-malic acid is used to
1208:malolactic fermentation
100:Hydroxybutanedioic acid
2018:Citrateâmalate shuttle
1957:
1495:
932:
926:
910:metabolic intermediate
105:2-Hydroxysuccinic acid
2865:CoA + ATP (GTP)
1956:
1494:
1057:anaplerotic reactions
876:. Malic acid has two
3130:Cellular respiration
2318:Ough, C. S. (1988).
1275:fuming sulfuric acid
1255:may be separated by
1085:Carl Wilhelm Scheele
83:Preferred IUPAC name
3155:Alpha hydroxy acids
3140:Cosmetics chemicals
2263:2007JChEd..84..924J
1068:phosphoenolpyruvate
637:Solubility in water
39:
3170:E-number additives
3145:Dicarboxylic acids
2445:. 8 September 2011
2382:Bartek Ingredients
2376:2018-06-25 at the
1958:
1496:
1365:α-phenylethylamine
1026:C4 carbon fixation
831:Infobox references
732:Related compounds
37:
3117:
3116:
3112:
3111:
2872:+ ADP (GDP)
2686:metabolic pathway
2683:Citric acid cycle
2561:Organic Syntheses
2534:Organic Syntheses
2476:978-92-5-104949-5
2271:10.1021/ed084p924
1271:Self-condensation
1257:chiral resolution
1107:—as is its
1089:Antoine Lavoisier
1041:citric acid cycle
1010:
991:
976:
972:
968:
914:citric acid cycle
891:
887:
883:
870:dicarboxylic acid
851:molecular formula
839:Chemical compound
837:
836:
776:Related compounds
559:O=C(O)CC(O)C(=O)O
481:CompTox Dashboard
450:
438:
401:
389:
283:
271:
219:
207:
174:Interactive image
112:
70:
3182:
3165:Chelating agents
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2422:. 26 August 2021
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2065:
2060:. Archived from
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1998:
1990:
1872:
1867:
1862:
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1852:
1847:
1842:
1837:
1832:
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1727:
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1672:
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1647:
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1527:
1522:
1517:
1512:
1507:
1502:
1359:
1358:
1334:Walden inversion
1322:
1249:maleic anhydride
1101:word for apple,
1008:
1005:
989:
986:
974:
970:
966:
935:
929:
889:
885:
881:
867:
847:organic compound
821:
815:
812:
811:
755:carboxylic acids
717:
620:1.609 gâ
cm
575:Chemical formula
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504:
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487:
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2378:Wayback Machine
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2358:seriouseats.com
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338:(preservatives)
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2598:Annual Reviews
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2518:978-3527306732
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2297:"FruchtsÀuren"
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2118:(5): 771â778.
2101:
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2064:on 2009-01-22.
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3160:Acids in wine
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2911:NADH + H + CO
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2058:chemblink.com
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2034:
2031:
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2019:
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2014:
2013:Acids in wine
2011:
2010:
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1371:Plant defense
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1282:coumalic acid
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1060:
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1051:group on the
1050:
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1011:-Malic acid (
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992:-Malic acid (
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904:. The malate
903:
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879:
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874:food additive
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852:
848:
844:
832:
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803:
797:
794:
793:Sodium malate
790:
786:
785:Butyraldehyde
782:
779:
774:
773:
770:
766:
765:Tartaric acid
762:
761:Succinic acid
759:
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626:Melting point
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294:ECHA InfoCard
291:
290:
278:
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266:
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238:ChEMBL1455497
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55:
50:
46:
41:
33:
26:
22:
3101:
3063:
3024:
2982:
2941:
2880:Succinyl-CoA
2878:
2839:
2801:
2762:
2729:Oxaloacetate
2727:
2700:
2593:
2587:
2581:
2564:
2560:
2554:
2537:
2533:
2527:
2498:
2492:
2480:. Retrieved
2465:
2458:
2447:. Retrieved
2436:
2424:. Retrieved
2419:
2410:
2399:. Retrieved
2389:
2366:
2357:
2348:
2320:
2313:
2300:
2287:
2254:
2250:
2240:
2229:
2224:
2216:
2212:
2208:
2204:
2200:
2191:
2180:. Retrieved
2176:
2166:
2157:
2148:
2115:
2111:
2104:
2076:
2070:
2062:the original
2057:
2048:
1988:
1399:
1398:
1374:
1354:
1346:silver oxide
1338:Walden cycle
1331:
1325:
1269:
1265:fumaric acid
1260:
1243:
1235:
1216:
1205:
1137:blackberries
1128:
1124:
1118:
1112:
1102:
1092:
1078:
1061:
1052:
1044:
1037:Calvin cycle
1022:biochemistry
1019:
1012:
993:
965:
962:Biochemistry
937:
923:
901:
842:
841:
769:Fumaric acid
696:
679:
670:
661:
651:
133:Identifiers
122:
117:
109:
104:
99:
94:Other names
25:malonic acid
2600:: 277â311.
2482:10 February
2033:Maleic acid
1253:enantiomers
1223:citric acid
1212:lactic acid
1177:Sour apples
1141:blueberries
1081:apple juice
723:Flash point
607:Appearance
568:Properties
300:100.027.293
213:CHEBI:30797
201:CHEBI:30796
113:-Malic acid
71:-Malic acid
38:Malic acid
21:maleic acid
3124:Categories
3037:NAD(P)H +
3026:Isocitrate
2702:Acetyl-CoA
2449:2011-10-27
2401:2011-10-27
2371:Malic Acid
2257:(6): 924.
2217:apple acid
2211:Ă
ple-syran
2182:2022-08-08
2040:References
1277:gives the
1231:INS number
1153:mirabelles
1125:ApfelsÀure
1120:ĂpfelsĂ€ure
868:. It is a
843:Malic acid
708:Pictograms
610:Colorless
598:Molar mass
469:817L1N4CKP
346:IUPHAR/BPS
249:ChemSpider
194:CHEBI:6650
161:3D model (
140:CAS Number
2985:Aconitate
2841:Succinate
2630:221360634
2614:0066-4286
2292:Tabelle I
2279:0021-9584
2132:0966-0844
2112:BioMetals
1301:H â HO
1293:CCH(OH)CH
1087:in 1785.
1039:. In the
1024:. In the
948:Maloideae
944:taxonomic
920:Etymology
858:CCH(OH)CH
849:with the
699:labelling
321:230-022-8
313:EC Number
150:6915-15-7
2803:Fumarate
2622:32853099
2374:Archived
2340:16866762
2305:Archived
2140:19288211
2096:11865673
2007:See also
1377:molasses
1336:and the
1219:E number
1189:ripeness
1145:cherries
1133:apricots
1129:Malat(e)
753:Related
690:Hazards
331:E number
3039:
2943:Citrate
2753:NADH +H
2259:Bibcode
2234:p. 108.
1409:[[File:
1362:resolve
1245:Racemic
1201:vinegar
1193:rhubarb
1173:citrus.
1157:peaches
1075:In food
1035:in the
952:Malinae
912:in the
902:malates
880:forms (
824:what is
822: (
781:Butanol
727:203 °C
685:= 14.5
648:Acidity
616:Density
592:
412:PubChem
3073:
3034:NAD(P)
3002:
2951:
2788:
2764:Malate
2628:
2620:
2612:
2567:: 80.
2540:: 23.
2515:
2473:
2338:
2328:
2277:
2138:
2130:
2094:
2084:
1344:. Wet
1279:pyrone
1233:296).
1181:grapes
1169:quince
1167:, and
1149:grapes
973:- and
956:Maleae
954:, and
898:esters
884:- and
845:is an
819:verify
816:
746:Malate
740:anions
738:Other
676:= 5.20
667:= 3.40
552:SMILES
447:
444:222656
435:
398:
395:C00149
386:
383:C00497
376:C00711
280:
277:193317
268:
229:ChEMBL
216:
204:
77:Names
2626:S2CID
2596:(1).
2426:5 May
1383:, so
1197:sumac
1165:plums
1161:pears
1114:Malus
1111:name
1109:genus
1104:mÄlum
1099:Latin
939:Malus
933:mÄlus
927:mÄlum
908:is a
906:anion
894:salts
517:InChI
432:92824
336:E296
265:83793
185:ChEBI
163:JSmol
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