1.0 2010-04-08 22:05:44 UTC 2019-11-26 02:58:50 UTC FDB003291 Fumaric acid Produced industrially by fermentation of Rhizopus nigricans, or manufactured by catalytic or thermal isomerisation of maleic anhydride or maleic acid. Used as an antioxidant, acidulant, leavening agent and flavouring agent in foods. Present in raw lean fish. Dietary supplement. Used in powdered products since fumaric acid is less hygroscopic than other acids. A precursor to L-malate in the Krebs tricarboxylic acid cycle. It is formed by the oxidation of succinate by succinate dehydrogenase (wikipedia). Fumaric acid is also found in garden tomato, papaya, wild celery, and star fruit. (2e)-2-Butenedioate (2E)-2-Butenedioic acid (2E)-But-2-enedioate (2E)-But-2-enedioic acid (E)-2-Butenedioate (e)-2-Butenedioic acid (E)-2-Butenedioic acid, 9CI 2-(E)-Butenedioate 2-(E)-Butenedioic acid Allomaleate Allomaleic acid Boletate Boletic acid E297 FC 33 FEMA 2488 Fumarate Fumarsaeure Glaucic acid Lichenate Lichenic acid Paramaleic acid Toxilic acid trans-1,2-Ethylenedicarboxylate trans-1,2-Ethylenedicarboxylic acid trans-2-Butenedioate trans-2-Butenedioic acid trans-But-2-enedioate trans-But-2-enedioic acid trans-Butenedioate trans-Butenedioic acid trans-Ethylene-1,2-dicarboxylic acid Tumaric acid C4H4O4 116.0722 116.010958616 (2E)-but-2-enedioic acid fumaric acid 110-17-8 OC(=O)\C=C/C(O)=O InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1- VZCYOOQTPOCHFL-UPHRSURJSA-N belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Dicarboxylic acids and derivatives Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Dicarboxylic acids and derivatives Aliphatic acyclic compounds Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Organic oxides Unsaturated fatty acids Aliphatic acyclic compound Carbonyl group Carboxylic acid Dicarboxylic acid or derivatives Fatty acid Fatty acyl Hydrocarbon derivative Organic oxide Organic oxygen compound Organooxygen compound Unsaturated fatty acid butenedioic acid Solid logp 0.21 ALOGPS logs -0.68 ALOGPS solubility 2.41e+01 g/l ALOGPS melting_point Mp 300-302° (sealed tube) logp -0.041 ChemAxon pka_strongest_acidic 3.55 ChemAxon iupac (2E)-but-2-enedioic acid ChemAxon average_mass 116.0722 ChemAxon mono_mass 116.010958616 ChemAxon smiles OC(=O)\C=C/C(O)=O ChemAxon formula C4H4O4 ChemAxon inchi InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1- ChemAxon inchikey VZCYOOQTPOCHFL-UPHRSURJSA-N ChemAxon polar_surface_area 74.6 ChemAxon refractivity 24.61 ChemAxon polarizability 9.35 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Arginine and Proline Metabolism SMP00020 map00330 Aspartate Metabolism SMP00067 map00250 Citric Acid Cycle SMP00057 map00020 Mitochondrial Electron Transport Chain SMP00355 map00190 Phenylalanine and Tyrosine Metabolism SMP00008 map00360 Tyrosine Metabolism SMP00006 map00350 Urea Cycle SMP00059 map00330 Specdb::EiMs 232 Specdb::MsIr 210 Specdb::MsIr 211 Specdb::MsIr 212 Specdb::NmrTwoD 966 Specdb::NmrTwoD 1162 Specdb::CMs 360 Specdb::CMs 361 Specdb::CMs 362 Specdb::CMs 363 Specdb::CMs 364 Specdb::CMs 1063 Specdb::CMs 2816 Specdb::CMs 27694 Specdb::CMs 30157 Specdb::CMs 30188 Specdb::CMs 30290 Specdb::CMs 30291 Specdb::CMs 30542 Specdb::CMs 30868 Specdb::CMs 31017 Specdb::CMs 31937 Specdb::CMs 37314 Specdb::CMs 137191 Specdb::CMs 144925 Specdb::CMs 1051304 Specdb::CMs 1051305 Specdb::CMs 1051307 Specdb::MsMs 206 Specdb::MsMs 207 Specdb::MsMs 208 Specdb::MsMs 3041 Specdb::MsMs 178911 Specdb::MsMs 178912 Specdb::MsMs 178913 Specdb::MsMs 181236 Specdb::MsMs 181237 Specdb::MsMs 181238 Specdb::MsMs 2238392 Specdb::MsMs 2239169 Specdb::MsMs 2244560 Specdb::MsMs 2245542 Specdb::MsMs 2246647 Specdb::MsMs 2247651 Specdb::MsMs 2248738 Specdb::MsMs 2249627 Specdb::MsMs 2250808 Specdb::MsMs 2251612 Specdb::MsMs 2256268 Specdb::MsMs 2265303 Specdb::MsMs 2265304 Specdb::MsMs 2265305 Specdb::MsMs 3076341 Specdb::NmrOneD 1104 Specdb::NmrOneD 1163 Specdb::NmrOneD 2142 Specdb::NmrOneD 2830 Specdb::NmrOneD 4764 Specdb::NmrOneD 4765 Specdb::NmrOneD 142470 Specdb::NmrOneD 142471 Specdb::NmrOneD 142472 Specdb::NmrOneD 142473 Specdb::NmrOneD 142474 Specdb::NmrOneD 142475 Specdb::NmrOneD 142476 Specdb::NmrOneD 142477 Specdb::NmrOneD 142478 Specdb::NmrOneD 142479 Specdb::NmrOneD 142480 Specdb::NmrOneD 142481 Specdb::NmrOneD 142482 Specdb::NmrOneD 142483 Specdb::NmrOneD 142484 Specdb::NmrOneD 142485 Specdb::NmrOneD 142486 Specdb::NmrOneD 142487 Specdb::NmrOneD 142488 HMDB00134 18012 FUM #<Reference:0x000055ac4085cd60> #<Reference:0x000055ac4085cba8> #<Reference:0x000055ac4085c9f0> #<Reference:0x000055ac4085c838> #<Reference:0x000055ac4085c680> Anatidae Type 1 specific Anatidae 8830 Apple Type 1 specific Malus pumila 283210 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Beer Type 2 specific 0.0 0.0 0.0 mg/100 g Bison Type 1 specific Bison bison 9901 Broad bean Type 1 specific Vicia faba 3906 Broccoli Type 1 specific Brassica oleracea var. italica 36774 Brussel sprouts Type 1 specific Brassica oleracea var. gemmifera 178616 Buffalo Type 1 specific Bubalus bubalis 89462 Cabbage Type 1 specific Brassica oleracea var. capitata 3716 Carrot Type 1 specific Daucus carota ssp. sativus 79200 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Chickpea Type 1 specific Cicer arietinum 3827 Chives Type 1 specific Allium schoenoprasum 74900 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Common grape Type 1 specific Vitis vinifera 29760 Common pea Type 1 specific Pisum sativum 3888 Common sage Type 1 specific Salvia officinalis 38868 Cow milk, pasteurized, vitamin A + D added, 0% fat Type 2 specific Cow milk, pasteurized, vitamin A + D added, 1% fat Type 2 specific Cow milk, pasteurized, vitamin A + D added, 2% fat Type 2 specific Cow milk, pasteurized, vitamin D added, 3.25% fat Type 2 specific Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Fennel Type 1 specific Foeniculum vulgare 48038 Fig Type 1 specific Ficus carica 3494 Fishes Unknown generic Garden onion Type 1 specific Allium cepa 4679 Garden rhubarb Type 1 specific Rheum rhabarbarum 3621 Garden tomato (var.) Type 1 specific Solanum lycopersicum var. lycopersicum 397755 Grape wine Type 2 specific 3.75 7.5 0.0 mg/100 g Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Kohlrabi Type 1 specific Brassica oleracea var. gongylodes 109379 Lettuce Type 1 specific Lactuca sativa 4236 Mallard duck Type 1 specific Anas platyrhynchos 8839 Milk (Cow) Type 2 specific 15.287 41.5 11.2 uM Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Papaya Type 1 specific Carica papaya 3649 Parsley Type 1 specific Petroselinum crispum 4043 Pheasant Type 1 specific Phasianus colchicus 9054 Pomegranate Type 1 specific Punica granatum 22663 Potato Type 1 specific Solanum tuberosum 4113 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Sour cherry Type 1 specific Prunus cerasus 140311 Soy bean Type 1 specific Glycine max 3847 Squab Type 1 specific Columba 8931 Star fruit Type 1 specific Averrhoa carambola 28974 310.0 310.0 310.0 mg/100 g Sunflower Type 1 specific Helianthus annuus 4232 Sweet cherry Type 1 specific Prunus avium 42229 380.0 380.0 380.0 g/kg Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 White cabbage Type 1 specific Brassica oleracea L. var. capitata L. f. alba DC. Wild boar Type 1 specific Sus scrofa 9823 Wild carrot Type 1 specific Daucus carota 4039 Wild celery Type 1 specific Apium graveolens 4045 odorless sour Adenylosuccinate lyase P30566 ADSL Argininosuccinate lyase P04424 ASL Fumarate hydratase, mitochondrial P07954 FH acidulant 23 Any substance which is added to food to preserve or enhance its flavour and/or appearance. anti dermatitic 225 A drug used to treat or prevent skin disorders or for the routine care of skin. anti hepatocarcinogenic 325 A substance that inhibits or prevents the proliferation of neoplasms. anti psoriac 562 Any substance introduced into a living organism with therapeutic or diagnostic purpose. antioxidant 502 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324. antitumor 672 A substance that inhibits or prevents the proliferation of neoplasms. flavor 936 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.