FUMARIC ACID
FUMARIC ACID
Fumaric acid has a role as a food acidity regulator, a fundamental metabolite and a geroprotector.
Fumaric acid is the trans isomer of butenedioic acid, while maleic acid is the cis isomer.
Fumaric acid is a butenedioic acid in which the C=C double bond has E geometry.
CAS Number: 110-17-8
EC Number: 203-743-0
Chemical Formula: HOOCCHCHCOOH
Molar Mass: 116.07 g/mol
Synonyms: fumaric acid, 110-17-8, 2-Butenedioic acid, trans-Butenedioic acid, Allomaleic acid, fumarate, Lichenic acid, Boletic acid, Tumaric acid, (2E)-but-2-enedioic acid, trans-1,2-Ethylenedicarboxylic acid, Allomalenic acid, But-2-enedioic acid, trans-2-Butenedioic acid, (E)-2-Butenedioic acid, Fumaricum acidum, 2-Butenedioic acid, (E)-, Kyselina fumarova, Butenedioic acid, 2-Butenedioic acid (E)-, USAF EK-P-583, Butenedioic acid, (E)-, FEMA No. 2488, (2E)-2-butenedioic acid, Caswell No. 465E, FEMA Number 2488, NSC-2752, Fumarsaeure, Allomaleic-acid, Boletic-acid, Lichenic acid (VAN), 2-Butenedioic acid (2E)-, 1,2-Ethylenedicarboxylic acid, (E), CCRIS 1039, HSDB 710, 2-(E)-Butenedioic acid, Kyselina fumarova [Czech], trans-but-2-enedioic acid, (E)-but-2-enedioic acid, U-1149, ammonium fumarate, (E)-Butenedioic acid, 1,2-Ethenedicarboxylic acid, trans-, EPA Pesticide Chemical Code 051201, AI3-24236, 6915-18-0, EINECS 203-743-0, fumarate, 10, BRN 0605763, Fumaric acid (NF), Fumaric acid [NF], INS NO.297, DTXSID3021518, UNII-88XHZ13131, CHEBI:18012, E-2-Butenedioic acid, Fumaric acid (8CI), INS-297, NSC2752, ethylenedicarboxylic acid, FC 33 (acid), 88XHZ13131, E297, DTXCID601518, Maleic acid-2,3-13C2, E-297, 2(TRANS)-BUTENEDIOIC ACID, EC 203-743-0, 4-02-00-02202 (Beilstein Handbook Reference), fum, Maleic-2,3-d2 acid, F0067, FUMARIC ACID (II), FUMARIC ACID [II], (E)-2-Butenedioate, Fumaric acid 1000 microg/mL in Acetonitrile:Water, FUMARIC ACID (MART.), FUMARIC ACID [MART.], FUMARIC ACID (USP-RS), FUMARIC ACID [USP-RS], (2E)-but-2-enedioate, FUMARIC ACID (USP IMPURITY), FUMARIC ACID [USP IMPURITY], Donitic acid, but-2-enedioicacid, CAS-110-17-8, trans-1,2-Ethenedicarboxylic acid, MALIC ACID IMPURITY A (EP IMPURITY), MALIC ACID IMPURITY A [EP IMPURITY], (E)-1,2-Ethylenedicarboxylic acid, trans-1,2-Ethylenediccarboxylic acid, SODIUM AUROTHIOMALATE IMPURITY B (EP IMPURITY), SODIUM AUROTHIOMALATE IMPURITY B [EP IMPURITY], fumarsaure, Allomaleate, Boletate, Lichenate, Acide fumarique, Acido lichenico, fumeric acid, Acido boletico, Acido fumarico, Acidum fumaricum, Acido allomaleico, trans-Butenedioate, NCGC00091192-02, 24461-33-4, 26099-09-2, Fumaric Acid,(S), MFCD00002700, trans-2-Butendisaure, trans-2-Butenedioate, 2-(E)-Butenedioate, Fumaric acid, 99%, Acido trans butendioico, FUM (CHRIS Code), trans-Ethylendicarbonsaure, (Trans)-butenedioic acid, Fumaric acid, >=99%, FEMA Number: 2488, bmse000083, D03GOO, FUMARIC ACID [MI], WLN: QV1U1VQ-T, FUMARIC ACID [FCC], Futrans-2-Butenedioic Acid, SCHEMBL1177, FUMARIC ACID [FHFI], FUMARIC ACID [HSDB], FUMARIC ACID [INCI], FUMARIC ACID [VANDF], MLS002454406, 1,2-ethylenedicarboxylic acid, 2-butenedioic acid, (2E)-, (2E)-2-Butenedioic acid #, S04-0167, FUMARIC ACID [WHO-DD], CHEMBL503160, FUMARICUM ACIDUM [HPUS], trans-1,2-Ethylenedicarboxylate, BDBM26122, CHEBI:22958, 2-Butenedioic acid (2E-(9CI), HMS2270C12, Pharmakon1600-01301022, Fumaric acid, >=99.0% (T), AMY30339, STR02646, Acido trans 1,2-etenedicarbossilico, Tox21_201769, Tox21_302826, 2-Butenedioic acid (2E)- (9CI), Acido trans 1,2-etilendicarbossilico, Fumaric acid, >=99%, FCC, FG, LS-500, NA9126, NSC760395, s4952, AKOS000118896, Fumaric acid, qNMR Standard for DMSO, CCG-266065, CS-W016599, DB01677, HY-W015883, NSC-760395, OR17920, USEPA/OPP Pesticide Code: 051201, NCGC00091192-01, NCGC00091192-03, NCGC00256360-01, NCGC00259318-01, BP-13087, Fumaric acid, tested according to USP/NF, SMR000112117, Fumaric acid, puriss., >=99.5% (T), EN300-17996, Fumaric acid, Vetec(TM) reagent grade, 99%, 1, (E), C00122, D02308, D85166, Q139857, Fumaric acid, BioReagent, suitable for cell culture, J-002389, Fumarate; 2-Butenedioic acid; Trans-Butenedioic acid, Z57127460, F8886-8257, Fumaric acid, certified reference material, TraceCERT(R), 26B3632D-E93F-4655-90B0-3C17855294BA, Fumaric acid, anhydrous, free-flowing, Redi-Dri(TM), >=99%, Fumaric acid, European Pharmacopoeia (EP) Reference Standard, Fumaric acid, United States Pharmacopeia (USP) Reference Standard, Fumaric Acid, Pharmaceutical Secondary Standard; Certified Reference Material, 623158-97-4, Fumaric acid [Wiki], (2E)-2-Butendisäure [German] [ACD/IUPAC Name], (2E)-2-Butenedioic acid [ACD/IUPAC Name], (2E)-But-2-enedioic acid, (E)-1,2-Ethylenedicarboxylic acid, (E)-2-Butenedioic acid, (E)-Butenedioic acid, 1,2-Ethenedicarboxylic acid, trans-, 110-17-8 [RN], 203-743-0 [EINECS], 2-Butenedioic acid [ACD/IUPAC Name], 2-Butenedioic acid (2E)-, 2-Butenedioic acid, (2E)- [ACD/Index Name], 2-Butenedioic acid, (E)-, 605763 [Beilstein], Acide (2E)-2-butènedioïque [French] [ACD/IUPAC Name], Acidum fumaricum, Butenedioic acid, (E)-, E-2-Butenedioic acid, MFCD00002700 [MDL number], trans-1,2-ethenedicarboxylic acid, trans-1,2-ethylenedicarboxylic acid, TRANS-2-BUTENEDIOIC ACID, trans-but-2-enedioic acid, trans-Butenedioic acid, (2E)-But-2-enedioate, (E)-2-Butenedioate, (E)-but-2-enedioate, (E)-but-2-enedioic acid, (E)-HO2CCH=CHCO2H, 1,2-Ethylenedicarboxylic acid, (E), 2-(E)-Butenedioate, 2-(E)-Butenedioic acid, 2-Butenedioic acid (E)-, 4-02-00-02202 [Beilstein], 605762 [Beilstein], Allomalenic acid, Boletate, Boletic acid, cis-Butenedioic acid, Fumaric acidmissing, Fumaricum acidum, Fumarsaeure, Kyselina fumarova [Czech], Lichenate, Lichenic acid (VAN), phenanthrene-9,10-dione, phenanthrene-9,10-dione;9,10-Phenanthraquinone, QV1U1VQ-T [WLN], STR02646, trans-1,2-Ethylenedicarboxylate, trans-1,2-Ethylentricarboxylic acid, trans-2-Butenedioate, trans-Butenedioate, 延胡索酸 [Chinese]
Fumaric acid is an organic compound with the formula HO2CCH=CHCO2H.
A white solid, fumaric acid occurs widely in nature.
Fumaric acid has a fruit-like taste and has been used as a food additive.
Fumaric acid E number is E297.
The salts and esters are known as fumarates.
Fumarate can also refer to the C4H2O2−4 ion (in solution).
Fumaric acid is the trans isomer of butenedioic acid, while maleic acid is the cis isomer.
Fumaric acid can be prepared by fermentation by employing Rhizopus species.
Recently, industrial-scale synthesis of fumaric acid from renewable feedstocks and lignocellulosic biomass has been proposed
Fumaric acid is an organic compound (this means Fumaric acid consists of carbon).
The chemical formula of fumaric acid is C4H4O4.
Fumaric acid is mostly found in Fumaric acid solid state and is white in color.
Fumaric acid has a fruit-like taste.
Fumaric acid is also known as Allomaleic acid.
Fumaric acid is a dicarboxylic acid.
Fumaric acid is widely used as a food additive.
Even the human skin produces fumaric acid when Fumaric acid is exposed to sunlight.
Fumaric acid is a by-product of the urea cycle in human beings.
The salts and esters of fumaric acid are collectively known as fumarates.
Fumaric and maleic acids were discovered by Braconnet and by Vauquelin separately while they were performing the dry distillation of malic acid in the year 1817.
Fumaric acid appears as a colorless crystalline solid.
The primary hazard is the threat to the environment.
Immediate steps should be taken to limit spread to the environment.
Combustible, though may be difficult to ignite.
Fumaric acid is used to make paints and plastics, in food processing and preservation, and for other uses.
Fumaric acid is a butenedioic acid in which the C=C double bond has E geometry.
Fumaric acid is an intermediate metabolite in the citric acid cycle.
Fumaric acid has a role as a food acidity regulator, a fundamental metabolite and a geroprotector.
Fumaric acid is a conjugate acid of a fumarate(1-).
Fumaric acid is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 10 000 to < 100 000 tonnes per annum. Fumaric acid is used by consumers, in articles, by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing. Fumaric acid or trans-butenedioic acid, is a white crystalline chemical compound widely found in nature. Fumaric acid is a key intermediate in the tricarboxylic acid cycle for organic acid biosynthesis in humans and other mammals. Fumaric acid is also an essential ingredient in plant life. When used as a food additive, the hydrophobic nature of fumaric acid results in persistent, long lasting sourness and flavor impact. The versatile compound also decreases the pH with minimal added sourness in products with pHs greater than 4.5. Fumaric acid low molecular weight gives fumaric acid more buffering capacity than other food acids at pHs near 3.O. Because of Fumaric acid strength, less fumaric acid is required when compared to other organic food acids, therefore reducing costs per unit weight. Fumaric acid (C4H4O4) is an organic acid widely found in nature, and is a component of organic biosynthesis is humans. Chemically, Fumaric acid is an unsaturated dicarboxylic acid. Fumaric acid exists as white or nearly white crystals, odorless with a very tart taste. Fumaric acid is generally nontoxic and nonirritant. Fumaric acid has been used in food and beverage products since the 1940s. Food research shows that fumaric acid can improve quality and reduce the costs of many food and beverage products. Fumaric acid is non-hygroscopic (absorbs no moisture). In the cosmetic industry, Fumaric acid is used as a bath salt cleaning agent for dentures. Fumaric acid also is used in animal feeds. Fumaric acid is used in oral pharmaceutical formulations and has been used clinically in the treatment of psoriasis. Dimethyl fumarate (Tecfidera) is the methyl ester of fumaric acid, and was approved in 2013 for use in multiple sclerosis. Fumaric acid is obtained from the transformation of maleic anhydride or maleic acid solutions resulting from the isomerization process (washing) of phthalic anhydride. Fumaric acid application areas are unsaturated polyester resins, the acidifying animal feed and plasticized products. Fumaric acid is an important specialty chemical with wide industrial applications ranging from Fumaric acid use as feedstock for the synthesis of polymeric resins to acidulant in foods and pharmaceuticals. Currently, fumaric acid is mainly produced by petroleum-based chemical synthesis. Limited petroleum resources, rising oil prices, and heightened environmental concern of chemical synthesis have prompted interest in the development of bio-based fumaric acid from renewable resources. Filamentous fungal fermentation with Rhizopus spp can produce fumaric acid from glucose via a reductive tricarboxylic acid (TCA) pathway and was once used in the industry before the rising of the petrochemical industry. However, conventional fumaric acid fermentation is expensive because of Fumaric acid low product yield and productivity. Filamentous fungal fermentation is also difficult to operate because of Fumaric acid morphology. Methods to control cell growth in the pellet form and to immobilize the mycelia in biofilm have been developed to improve fermentation performance. Fumaric acid attenuates the eotaxin-1 expression in TNF-α-stimulated fibroblasts by suppressing p38 MAPK-dependent NF-Κb signaling. Fumaric acid has recently been identified as an oncometabolite or an endogenous, cancer-causing metabolite. High levels of this organic acid can be found in tumors or biofluids surrounding tumors. Fumaric acid oncogenic action appears due to Fumaric acid ability to inhibit prolyl Hydroxylase-containing enzymes. Fumaric acid (Fumarate, 2-Butenedioic acid, Trans-Butenedioic acid) is an intermediate in the citric acid cycle used by cells to produce energy in the form of adenosine triphosphate (ATP) from food; also a product of the urea cycle. Fumaric acid is an organic compound with the formula (COOH)CH=CH(COOH). A white solid, fumaric acid occurs widely in nature. Fumaric acid has a fruit-like taste and has been used as a food additive. Fumaric acid E number is E297. Fumaric acid is the trans isomer of butenedioic acid, while maleic acid is the cis isomer. Fumaric acid is produced naturally in eukaryotic organisms from succinate in complex 2 of the electron transport chain via the enzyme succinate dehydrogenase, which is involved in ATP production. The food grade product can be obtained by chemical synthesis or by biosynthesis. Fumaric acid is used for controlling malolactic fermentation in wines under conditions stipulated by regulation. Production by chemical synthesis is the most common: Fumaric acid involves the isomerisation of maleic acid obtained from the hydrolysis of maleic anhydride, produced from the oxidation of butane or benzene. Production by biosynthesis, which is more sustainable, should develop rapidly. Fumaric acid involves the fermentation by Rhizopus oryzae, in particular, of agri-food residues (e.g. from apples). The fumaric acid is prepared in solution in a volume of wine before incorporation. Applications of Fumaric acid: Fumaric acid has been used as a standard for the quantitative determination of phenolic compounds in nettle samples by HPLC. Fumaric acid may be used in the preparation of L-Lysine-fumaric acid crystals. Fumaric acid may also be employed for the industrial manufacture of synthetic resins and eco-friendly/biodegradable polymers. When used in wine, Fumaric acid enables you to control malolactic fermentation. In fact, when added at an early stage after the end of alcoholic fermentation (fructose/glucose under 1 g/L), Fumaric acid blocks all malolactic fermentation. Added during malolactic fermentation, Fumaric acid allows the fermentation to be partially completed. Fumaric acid is a tool of great interest when you wish to limit [the use of SO2] or make wines without SO2. Uses of Fumaric acid: The esters of Fumaric acid are used for the treatment of psoriasis due to the antioxidants and anti-inflammation properties. Fumaric acid is used as a food additive. Fumaric acid helps preserve the taste and quality of the food products due to the low water absorption capacity of the Fumaric acid. Fumaric acid is used by pharmacies to produce ferrous fumarate and alexipharmic. Fumaric acid is used in the production of Tartaric acid. Fumaric acid is related to malic acid, and, like malic acid, Fumaric acid is involved in the production of energy (in the form of adenosine triphosphate [ATP]) from food. Fumaric acid is an essential biochemical in the cellular respiration of plants and animals. Fumaric acid is used as a fortifier (paper size resins, unsaturated polyester resins, and alkyd surface coating resins), food antioxidant, dye mordant, and medication. Fumaric acid is also used in dentifrices (stain remover) and to make other chemicals. Fumaric acid is used in rosin esters and adducts, drying oils, printing inks, and foods (acidulant and flavoring agent). Fumaric acid is used primarily in liquid pharmaceutical preparations as an acidulant and flavoring agent. Fumaric acid may be included as the acid part of effervescent tablet formulations, although this use is limited as Fumaric acid has an extremely low solubility in water. Fumaric acid is also used as a chelating agent which exhibits synergism when used in combination with other true antioxidants. In the design of novel pelletized formulations manufactured by extrusion-spheronization, fumaric acid was used to aid spheronization, favoring the production of fine pellets. Fumaric acid has also been investigated as an alternative filler to lactose in pellets. Fumaric acid has been investigated as a lubricant for effervescent tablets, and copolymers of fumaric acid and sebacic acid have been investigated as bioadhesive microspheres. Fumaric acid has also been used in film-coated pellet formulations as an acidifying agent and also to increase drug solubility. Fumaric acid is also used as a food additive at concentrations up to 3600 ppm, and as a therapeutic agent in the treatment of psoriasis and other skin disorders. Fumaric acid is naturally produced by the body, however for industrial applications Fumaric acid is synthesized chemically. Fumaric acid is used to impart a tart taste to processed foods. Fumaric acid is also used as an antifungal agent in boxed foods such as cake mixes and flours, as well as tortillas. Fumaric acid is also added to bread to increase the porosity of the final baked product. Fumaric acid is used to impart a sour taste to sourdough and rye bread. In cake mixes, Fumaric acid is used to maintain a low pH and prevent clumping of the flours used in the mix. In fruit drinks, fumaric acid is used to maintain a low pH which, in turn, helps to stabilize flavor and color. Fumaric acid also prevents the growth of E. coli in beverages when used in combination with sodium benzoate. When added to wines, fumaric acid helps to prevent further fermentation and yet maintain low pH and eliminate traces of metallic elements. In this fashion, Fumaric acid helps to stabilize the taste of wine. Fumaric acid can also be added to dairy products, sports drinks, jams, jellies and candies. Fumaric acid helps to break down bonds between gluten proteins in wheat and helps to create a more pliable dough. Fumaric acid is used in paper sizing, printer toner, and polyester resin for making molded walls. Food: Fumaric acid has been used as a food acidulant since 1946. Fumaric acid is approved for use as a food additive in the EU, USA and Australia and New Zealand. As a food additive, Fumaric acid is used as an acidity regulator and can be denoted by the E number E297. Fumaric acid is generally used in beverages and baking powders for which requirements are placed on purity. Fumaric acid is used in the making of wheat tortillas as a food preservative and as the acid in leavening. Fumaric acid is generally used as a substitute for tartaric acid and occasionally in place of citric acid, at a rate of 1 g of fumaric acid to every ~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, such as "Salt and Vinegar" flavored potato chips, Fumaric acid is also used as a coagulant in stove-top pudding mixes. The European Commission Scientific Committee on Animal Nutrition, part of DG Health, found in 2014 that fumaric acid is "practically non-toxic" but high doses are probably nephrotoxic after long-term use. Medicine: Fumaric acid was developed as a medicine to treat the autoimmune condition psoriasis in the 1950s in Germany as a tablet containing 3 esters, primarily dimethyl fumarate, and marketed as Fumaderm by Biogen Idec in Europe. Biogen would later go on to develop the main ester, dimethyl fumarate, as a treatment for multiple sclerosis. In patients with relapsing-remitting multiple sclerosis, the ester dimethyl fumarate (BG-12, Biogen) significantly reduced relapse and disability progression in a phase 3 trial. Fumaric acid activates the Nrf2 antioxidant response pathway, the primary cellular defense against the cytotoxic effects of oxidative stress. Widespread uses by professional workers: Fumaric acid is used in the following products: laboratory chemicals, adhesives and sealants, plant protection products, inks and toners and pH regulators and water treatment products. Fumaric acid is used in the following areas: scientific research and development, building & construction work and agriculture, forestry and fishing. Fumaric acid is used for the manufacture of: machinery and vehicles, furniture and electrical, electronic and optical equipment. Release to the environment of Fumaric acid can occur from industrial use: as an intermediate step in further manufacturing of another substance (use of intermediates). Other release to the environment of Fumaric acid is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners) and outdoor use. Uses at industrial sites: Fumaric acid is used in the following products: polymers, adhesives and sealants, coating products, pharmaceuticals, inks and toners and laboratory chemicals. Fumaric acid has an industrial use resulting in manufacture of another substance (use of intermediates). Fumaric acid is used in the following areas: formulation of mixtures and/or re-packaging and scientific research and development. Fumaric acid is used for the manufacture of: chemicals. Release to the environment of Fumaric acid can occur from industrial use: as an intermediate step in further manufacturing of another substance (use of intermediates), for thermoplastic manufacture and as processing aid. Industry Uses: Agricultural chemicals (non-pesticidal) Intermediates Monomers Not Known or Reasonably Ascertainable Other (specify) Paint additives and coating additives not described by other categories Processing aids not otherwise specified Processing aids, specific to petroleum production Surface active agents Waterproofing agent Consumer Uses: Fumaric acid is used in the following products: adhesives and sealants, coating products, inks and toners and cosmetics and personal care products. Other release to the environment of Fumaric acid is likely to occur from: outdoor use and indoor use as processing aid. Other Consumer Uses: Agricultural chemicals (non-pesticidal) Flavoring and nutrient Not Known or Reasonably Ascertainable Other (specify) Therapeutic Uses: Fumaric acid is used in oral pharmaceutical formulations and food products, and is generally regarded as a relatively nontoxic and nonirritant material. Fumaric acid preparations are used as long term and effective treatment of psoriasis. Fumaric acid and Fumaric acid esters (FAE) are already in use for treatment of psoriasis and are known to have an immunomodulatory effect. A phase II clinical study in relapsing-remitting multiple sclerosis (RRMS) patients with the modified fumaric acid ester BG-12 showed as "proof of principle" in a frequent MRI design that FAE significantly reduce the number of gadolinium-enhancing lesions after 24 weeks of treatment. Further phase III studies have been started to explore the long-term efficacy of this substance. Oral treatment of psoriasis on an outpatient basis, using a preparation containing fumaric acid derivatives, was evaluated as initial monotherapy (3 months) and as long-term basic therapy (12-14 months) in 13 and 11 patients, respectively. The course of the disease was analysed in each individual case. After completion of both parts of the trial, half of the patients that had only responded poorly to conventional antipsoriatic therapy showed a significant improvement which occurred after several weeks of treatment. In 4 patients the medication had to be stopped because of abdominal pain. No severe side effects, particularly of renal, hepatic or hematological nature, could be established. Studies in mice and rats disclosed only a low acute toxicity of the fumaric acid derivatives used. In additional analyses, hypotheses were dealt with concerning the mechanism of action of fumaric acid in psoriasis. To establish fumaric acid derivatives in the treatment of psoriasis, studies on chronic toxicity and pharmacokinetics will have to be conducted. Further clinical trials should evaluate a single fumaric acid derivative instead of mixtures. Other uses: Fumaric acid is used in the manufacture of polyester resins and polyhydric alcohols and as a mordant for dyes. When fumaric acid is added to their feed, lambs produce up to 70% less methane during digestion. Industrial Processes with risk of exposure: Pulp and Paper Processing Painting (Pigments, Binders, and Biocides) Textiles (Printing, Dyeing, or Finishing) Typical Properties of Fumaric acid: Physical Properties: Fumaric acid mostly appears as a white-colored solid. Fumaric acid has a fruit-like odor. The molecular weight of Fumaric acid is 116 amu. Fumaric acid is Combustible but Fumaric acid is difficult to start a fire. Fumaric acid undergoes sublimation at 200 C. The melting point of Fumaric acid is 572 to 576 °F. Chemical Properties: Fumaric acid is soluble in ethanol and concentrated sulfuric acid. Fumaric acid is soluble in alcohol but is insoluble in benzene, water, and chloroform. The capacity to absorb atmospheric moisture is very less. The pH of Fumaric acid is 3.19 When Fumaric acid is heated in presence of Bayers reagent Fumaric acid gives rise to Racemic Tartaric Acid. Characteristics of Fumaric acid: One of Fumaric acid properties is to inhibit or block malolactic fermentation at a certain concentration. Fumaric acid is therefore a tool of choice to limit the use of the SO2 previously used for this purpose. Synthesis and Reactions of Fumaric acid: Fumaric acid was first prepared from succinic acid. A traditional synthesis involves oxidation of furfural (from the processing of maize) using chlorate in the presence of a vanadium-based catalyst. Currently, industrial synthesis of fumaric acid is mostly based on catalytic isomerisation of maleic acid in aqueous solutions at low pH. Maleic acid is accessible in large volumes as a hydrolysis product of maleic anhydride, produced by catalytic oxidation of benzene or butane. The chemical properties of fumaric acid can be anticipated from Fumaric acid component functional groups. This weak acid forms a diester, Fumaric acid undergoes additions across the double bond, and Fumaric acid is an excellent dienophile. Fumaric acid does not combust in a bomb calorimeter under conditions where maleic acid deflagrates smoothly. For teaching experiments designed to measure the difference in energy between the cis- and trans- isomers, a measured quantity of carbon can be ground with the subject compound and the enthalpy of combustion computed by difference. Formula of Fumaric acid: The fumaric acid formula, also named as Allomaleic acid formula is discussed in this article. Fumaric acid is a dicarboxylic acid and a conjugate acid of fumarate. The molecular or chemical formula of Fumaric acid is C4H4O4. Fumaric acid is a precursor to L-malate in the TCA cycle. Fumaric acid is generated by oxidizing succinic acid using succinate dehydrogenase. Fumarate is converted to malate by the enzyme fumarase. High levels of Allomaleic acid is present in biofluids surrounding tumours or inside the tumours. Manufacturing Methods of Fumaric acid: Commercially, fumaric acid may be prepared from glucose by the action of fungi such as Rhizopus nigricans, as a by-product in the manufacture of maleic and phthalic anhydrides, and by the isomerization of maleic acid using heat or a catalyst. On the laboratory scale, fumaric acid can be prepared by the oxidation of furfural with sodium chlorate in the presence of vanadium pentoxide. Maleic acid or maleic anhydride, especially the maleic acid-containing wash water from the production of maleic anhydride or phthalic anhydride, serves as starting material for the manufacture of fumaric acid. The maleic acid concentration should be at least 30%. Maleic acid is converted almost quantitatively by thermal or catalytic isomerization into the sparingly soluble fumaric acid, which is recovered by filtration. Various substances have been proposed as catalysts: mineral acids (e.g., hydrochloric acid); sulfur compounds such as thiocyanates, thiazoles, thiosemicarbazides, thioureas; or bromine compounds in combination with peroxides (e.g., persulfate). Thiourea is most commonly used in practice. The maleic acid-containing wash water contains impurities that can affect quality and yield. This problem can be largely avoided (1) by thermal pretreatment of the wash water, (2) by adding urea if thiourea is used as catalyst, and (3) by addition of sulfites or passaged of sulfur dioxide and addition of mineral acids. The crude fumaric acid obtained is purified by recrystallization from water, combined with purification by active charcoal. Losses during purification are about 10%. General Manufacturing Information of Fumaric acid: Industry Processing Sectors: Agriculture, Forestry, Fishing and Hunting All Other Basic Organic Chemical Manufacturing Asphalt Paving, Roofing, and Coating Materials Manufacturing Construction Food, beverage, and tobacco product manufacturing Not Known or Reasonably Ascertainable Oil and Gas Drilling, Extraction, and Support activities Paint and Coating Manufacturing Plastics Material and Resin Manufacturing Textiles, apparel, and leather manufacturing Human Metabolite Information of Fumaric acid: Tissue Locations: Placenta Prostate Cellular Locations: Extracellular Membrane Mitochondria Biosynthesis and Occurrence of Fumaric acid: Fumaric acid is produced in eukaryotic organisms from succinate in complex 2 of the electron transport chain via the enzyme succinate dehydrogenase. Fumaric acid is one of two isomeric unsaturated dicarboxylic acids, the other being maleic acid. In fumaric acid the carboxylic acid groups are trans (E) and in maleic acid they are cis (Z). Fumaric acid is found in fumitory (Fumaria officinalis), bolete mushrooms (specifically Boletus fomentarius var. pseudo-igniarius), lichen, and Iceland moss. Fumarate is an intermediate in the citric acid cycle used by cells to produce energy in the form of adenosine triphosphate (ATP) from food. Fumaric acid is formed by the oxidation of succinate by the enzyme succinate dehydrogenase. Fumarate is then converted by the enzyme fumarase to malate. Human skin naturally produces fumaric acid when exposed to sunlight. Fumarate is also a product of the urea cycle. Handling and storage of Fumaric acid: Conditions for safe storage, including any incompatibilities: Storage conditions: Tightly closed. Dry. Storage class: Storage class (TRGS 510): 11: Combustible Solids Stability and Reactivity of Fumaric acid: Reactivity Forms explosive mixtures with air on intense heating. A range from approx. 15 Kelvin below the flash point is to be rated as critical. The following applies in general to flammable organic substances and mixtures: In correspondingly fine distribution, when whirled up a dust explosion potential may generally be assumed. Chemical stability: Fumaric acid is chemically stable under standard ambient conditions (room temperature). Possibility of hazardous reactions: Violent reactions possible with: Oxidizing agents Bases Reducing agents Amines Conditions to avoid: Strong heating. Incompatible materials: No data available Safety of Fumaric acid: Fumaric acid is "practically non-toxic" but high doses are probably nephrotoxic after long-term use. First Aid Measures of Fumaric acid: EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. Fire Fighting of Fumaric acid: Use water spray, dry powder, foam, carbon dioxide. Fire Fighting Procedures: If material on fire or involved in fire: Use water in flooding quantities as fog. Solid streams of water may spread fire. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemicals, or carbon dioxide. Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Special protective equipment for fire-fighters: Wear self contained breathing apparatus for fire fighting if necessary. Accidental release measures of Fumaric acid: Personal precautions, protective equipment and emergency procedures Advice for non-emergency personnel: Avoid inhalation of dusts. Avoid substance contact. Ensure adequate ventilation. Evacuate the danger area, observe emergency procedures, consult an expert. Environmental precautions: Do not let product enter drains. Methods and materials for containment and cleaning up: Cover drains. Collect, bind, and pump off spills. Observe possible material restrictions. Take up dry. Dispose of properly. Clean up affected area. Avoid generation of dusts. Identifiers of Fumaric acid: CAS Number: 110-17-8 Beilstein Reference: 605763 ChEBI: CHEBI:18012 ChEMBL: ChEMBL503160 ChemSpider: 10197150 DrugBank: DB04299 ECHA InfoCard: 100.003.404 EC Number: 203-743-0 E number: E297 (preservatives) Gmelin Reference: 49855 KEGG: C00122 PubChem CID: 444972 RTECS number: LS9625000 UNII: 88XHZ13131 UN number: 9126 CompTox Dashboard (EPA): DTXSID3021518 InChI: InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+ Key: VZCYOOQTPOCHFL-OWOJBTEDSA-N InChI=1/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+ Key: VZCYOOQTPOCHFL-OWOJBTEDBF SMILES: C(=C/C(=O)O)C(=O)O CAS number: 110-17-8 EC index number: 607-146-00-X EC number: 203-743-0 Grade: ChP,NF,JPE Hill Formula: C₄H₄O₄ Chemical formula: HOOCCHCHCOOH Molar Mass: 116.07 g/mol HS Code: 2917 19 80 Synonym(s): (2E)-2-Butenedioic acid, trans-Butenedioic acid Linear Formula: HOOCCH=CHCOOH CAS Number: 110-17-8 Molecular Weight: 116.07 Beilstein: 605763 EC Number: 203-743-0 MDL number: MFCD00002700 eCl@ss: 39021709 PubChem Substance ID: 329757345 NACRES: NA.21 Properties of Fumaric acid: Chemical formula: C4H4O4 Molar mass: 116.072 g·mol−1 Appearance: White solid Density: 1.635 g/cm3 Melting point: 287 °C (549 °F; 560 K) (decomposes) Solubility in water: 4.9 g/L at 20 °C Acidity (pKa): pka1 = 3.03, pka2 = 4.44 (15 °C, cis isomer) Magnetic susceptibility (χ): −49.11·10−6 cm3/mol Dipole moment: non zero vapor pressure: 1.7 mmHg ( 165 °C) Quality Level: 200 grade: purum Assay: ≥99.0% (T) form: powder autoignition temp.: 1364 °F expl. lim.: 40 % mp: 298-300 °C (subl.) (lit.) solubility: 95% ethanol: soluble 0.46 g/10 mL, clear, colorless SMILES string: OC(=O)C=CC(O)=O InChI: 1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+ InChI key: VZCYOOQTPOCHFL-OWOJBTEDSA-N Boiling point: 290 °C (1013 hPa) (sublimed) Density: 1.64 g/cm3 (20 °C) Flash point: 273 °C Ignition temperature: 375 °C Melting Point: 287 °C pH value: 2.1 (4.9 g/l, H₂O, 20 °C) Vapor pressure: <0.001 hPa (20 °C) Solubility: 4.9 g/l Molecular Weight: 116.07 g/mol XLogP3: -0.3 Hydrogen Bond Donor Count: 2 Hydrogen Bond Acceptor Count: 4 Rotatable Bond Count: 2 Exact Mass: 116.01095860 g/mol Monoisotopic Mass: 116.01095860 g/mol Topological Polar Surface Area: 74.6Ų Heavy Atom Count: 8 Complexity: 119 Isotope Atom Count: 0 Defined Atom Stereocenter Count: 0 Undefined Atom Stereocenter Count: 0 Defined Bond Stereocenter Count: 1 Undefined Bond Stereocenter Count: 0 Covalently-Bonded Unit Count: 1 Compound Is Canonicalized: Yes Specifications of Fumaric acid: Assay (calc. on anhydrous substance): 99.5 - 100.5 % Assay (HPLC; calc. on anhydrous substance): 98.0 - 102.0 % Identity (IR): passes test Identity (JPE 1): passes test Identity (JPE 2/ChP 1): passes test Identity (JPE 3): passes test Identity (HPLC): passes test Appearance of solution: passes test Sulfate (SO₄): ≤ 0.010 % Heavy metals (as Pb): ≤ 10 ppm As (Arsenic): ≤ 2 ppm Malic acid (HPLC) (NF): ≤ 1.5 % Maleic acid (HPLC) (NF): ≤ 0.1 % Maleic acid (HPLC) (JPE): passes test Maleic acid (HPLC) (ChP): ≤ 0.1 % Any individual unspecified impurity (HPLC): ≤ 0.1 % Sum of all impurities (HPLC): ≤ 0.2 % Residual solvents (ICH Q3C): excluded by production process Water (K. F.): ≤ 0.5 % Sulfated ash: ≤ 0.05 % Related Products of Fumaric acid: Telaglenastat (CB-839)New Setanaxib (GKT137831)New LB-100New Puromycin 2HCl Cyclosporin A Cyclophosphamide Monohydrate Ganciclovir Calcitriol Ribavirin (ICN-1229) BAPTA-AM Related Compounds of Fumaric acid: Fumaryl chloride Fumaronitrile Dimethyl fumarate Ammonium fumarate Iron(II) fumarate Related carboxylic acids: Maleic acid Succinic acid Crotonic acid Names of Fumaric acid: Regulatory process names: Fumaric acid Fumaric acid fumaric acid Translated names: acide fumarique (fr) acido fumarico (it) Fumaarhape (et) Fumaarihappo (fi) fumaarzuur (nl) fumarna kiselina (hr) fumarna kislina (sl) fumaro rūgštis (lt) fumarová kyselina (cs) fumarsyra (sv) fumarsyre (da) fumarsyre (no) Fumarsäure (de) fumársav (hu) fumārskābe (lv) kyselina fumarová (sk) ácido fumárico (es) ácido fumárico (pt) φουμαρικό οξύ (el) фумарова киселина (bg) IUPAC names: (2E)-but-2-enedioic acid (E) but-2-enedioic acid (E)-but-2-enedioic acid (E)-Butenedioic acid 1,2-ethylene dicarboxylic acid 2-BUTENEDIOIC ACID 2-Butenedioic acid (2E)-Fumaric acid 2-Butenedioic acid, E- acide fumarique But-2-enedioic acid but-2-enedioic acid E-butenedioic Acid FA Flakes FUMARIC ACID Fumaric Acid Fumaric acid fumaric acid Fumaric Acid Fumaric acid fumaric acid fumaric acid ,Butenedioic acid , Allomaleic acid , Boletic acid , Donitic acid , Lichenic acid Fumarsäure trans-1,2-Ethylenedicarboxylic trans-2-Butenedioïc acid trans-Butendisäure Trans-Butenedioic Acid Preferred IUPAC name: (2E)-But-2-enedioic acid Trade names: (E)-2-Butenedioic acid 1,2-ethylene dicarboxylic acid Allomaleic acid Boletic acid Butenedioic acid, (E)- Fumaric Acid trans-1,2-Ethylenedicarboxylic acid TRANS-BUTENEDICARBOXYLIC ACID Other names: Fumaric acid trans-1,2-Ethylenedicarboxylic acid 2-Butenedioic acid trans-Butenedioic acid Allomaleic acid Boletic acid Donitic acid Lichenic acid Other identifiers: 110-17-8 607-146-00-X 623158-97-4 909873-99-0