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FUMARATE

Fumarate has a role as a food acidity regulator, a fundamental metabolite and a geroprotector.

Fumarate is the trans isomer of butenedioic acid, while maleic acid is the cis isomer.

Fumarate 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]

Fumarate is an organic compound with the formula HO2CCH=CHCO2H.

A white solid, Fumarate occurs widely in nature.

Fumarate has a fruit-like taste and has been used as a food additive.

Fumarate E number is E297.

The salts and esters are known as Fumaric acid.

Fumarate can also refer to the C4H2O2−4 ion (in solution).

Fumarate is the trans isomer of butenedioic acid, while maleic acid is the cis isomer.

Fumarate can be prepared by fermentation by employing Rhizopus species.

Recently, industrial-scale synthesis of Fumarate from renewable feedstocks and lignocellulosic biomass has been proposed

Fumarate is an organic compound (this means Fumarate consists of carbon).

The chemical formula of Fumarate is C4H4O4.

Fumarate is mostly found in Fumarate solid state and is white in color.

Fumarate has a fruit-like taste.

Fumarate is also known as Allomaleic acid.

Fumarate is a dicarboxylic acid.

Fumarate is widely used as a food additive.

Even the human skin produces Fumarate when Fumarate is exposed to sunlight.

Fumarate is a by-product of the urea cycle in human beings.

The salts and esters of Fumarate are collectively known as Fumaric acid.

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.

Fumarate 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.

Fumarate is used to make paints and plastics, in food processing and preservation, and for other uses.

Fumarate is a butenedioic acid in which the C=C double bond has E geometry.

Fumarate is an intermediate metabolite in the citric acid cycle.

Fumarate has a role as a food acidity regulator, a fundamental metabolite and a geroprotector.

Fumarate is a conjugate acid of a Fumaric acid(1-).

Fumarate 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.

Fumarate is used by consumers, in articles, by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.

Fumarate or trans-butenedioic acid, is a white crystalline chemical compound widely found in nature.

Fumarate is a key intermediate in the tricarboxylic acid cycle for organic acid biosynthesis in humans and other mammals.

Fumarate is also an essential ingredient in plant life.

When used as a food additive, the hydrophobic nature of Fumarate 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.

Fumarate low molecular weight gives Fumarate more buffering capacity than other food acids at pHs near 3.O.

Because of Fumarate strength, less Fumarate is required when compared to other organic food acids, therefore reducing costs per unit weight.

Fumarate (C4H4O4) is an organic acid widely found in nature, and is a component of organic biosynthesis is humans.

Chemically, Fumarate is an unsaturated dicarboxylic acid.

Fumarate exists as white or nearly white crystals, odorless with a very tart taste.

Fumarate is generally nontoxic and nonirritant.

Fumarate has been used in food and beverage products since the 1940s.

Food research shows that Fumarate can improve quality and reduce the costs of many food and beverage products.

Fumarate is non-hygroscopic (absorbs no moisture).

In the cosmetic industry, Fumarate is used as a bath salt cleaning agent for dentures.

Fumarate also is used in animal feeds.

Fumarate is used in oral pharmaceutical formulations and has been used clinically in the treatment of psoriasis.

Dimethyl fumarate (Tecfidera) is the methyl ester of Fumarate, and was approved in 2013 for use in multiple sclerosis.

Fumarate is obtained from the transformation of maleic anhydride or maleic acid solutions resulting from the isomerization process (washing) of phthalic anhydride.

Fumarate application areas are unsaturated polyester resins, the acidifying animal feed and plasticized products.

Fumarate is an important specialty chemical with wide industrial applications ranging from Fumarate use as feedstock for the synthesis of polymeric resins to acidulant in foods and pharmaceuticals.

Currently, Fumarate 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 Fumarate from renewable resources.

Filamentous fungal fermentation with Rhizopus spp can produce Fumarate 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 Fumarate fermentation is expensive because of Fumarate low product yield and productivity.

Filamentous fungal fermentation is also difficult to operate because of Fumarate morphology.

Methods to control cell growth in the pellet form and to immobilize the mycelia in biofilm have been developed to improve fermentation performance.

Fumarate attenuates the eotaxin-1 expression in TNF-α-stimulated fibroblasts by suppressing p38 MAPK-dependent NF-Κb signaling.

Fumarate 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.

Fumarate oncogenic action appears due to Fumarate ability to inhibit prolyl Hydroxylase-containing enzymes.

Fumarate (Fumaric acid, 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.

Fumarate is an organic compound with the formula (COOH)CH=CH(COOH).

A white solid, Fumarate occurs widely in nature.

Fumarate has a fruit-like taste and has been used as a food additive.

Fumarate E number is E297.

Fumarate is the trans isomer of butenedioic acid, while maleic acid is the cis isomer.

Fumarate 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.

Fumarate is used for controlling malolactic fermentation in wines under conditions stipulated by regulation.

Production by chemical synthesis is the most common:

Fumarate 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.

Fumarate involves the fermentation by Rhizopus oryzae, in particular, of agri-food residues (e.g. from apples).

The Fumarate is prepared in solution in a volume of wine before incorporation.

Applications of Fumarate:

Fumarate has been used as a standard for the quantitative determination of phenolic compounds in nettle samples by HPLC.

Fumarate may be used in the preparation of L-Lysine-Fumarate crystals.

Fumarate may also be employed for the industrial manufacture of synthetic resins and eco-friendly/biodegradable polymers.

When used in wine, Fumarate 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), Fumarate blocks all malolactic fermentation.

Added during malolactic fermentation, Fumarate allows the fermentation to be partially completed.

Fumarate is a tool of great interest when you wish to limit [the use of SO2] or make wines without SO2.

Uses of Fumarate:

The esters of Fumarate are used for the treatment of psoriasis due to the antioxidants and anti-inflammation properties.

Fumarate is used as a food additive.

Fumarate helps preserve the taste and quality of the food products due to the low water absorption capacity of the Fumarate.

Fumarate is used by pharmacies to produce ferrous fumarate and alexipharmic.

Fumarate is used in the production of Tartaric acid.

Fumarate is related to malic acid, and, like malic acid, Fumarate is involved in the production of energy (in the form of adenosine triphosphate [ATP]) from food.

Fumarate is an essential biochemical in the cellular respiration of plants and animals.

Fumarate is used as a fortifier (paper size resins, unsaturated polyester resins, and alkyd surface coating resins), food antioxidant, dye mordant, and medication.

Fumarate is also used in dentifrices (stain remover) and to make other chemicals.

Fumarate is used in rosin esters and adducts, drying oils, printing inks, and foods (acidulant and flavoring agent).

Fumarate is used primarily in liquid pharmaceutical preparations as an acidulant and flavoring agent.

Fumarate may be included as the acid part of effervescent tablet formulations, although this use is limited as Fumarate has an extremely low solubility in water.

Fumarate 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, Fumarate was used to aid spheronization, favoring the production of fine pellets.

Fumarate has also been investigated as an alternative filler to lactose in pellets.

Fumarate has been investigated as a lubricant for effervescent tablets, and copolymers of Fumarate and sebacic acid have been investigated as bioadhesive microspheres.

Fumarate has also been used in film-coated pellet formulations as an acidifying agent and also to increase drug solubility.

Fumarate 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.

Fumarate is naturally produced by the body, however for industrial applications Fumarate is synthesized chemically.

Fumarate is used to impart a tart taste to processed foods.

Fumarate is also used as an antifungal agent in boxed foods such as cake mixes and flours, as well as tortillas.

Fumarate is also added to bread to increase the porosity of the final baked product.

Fumarate is used to impart a sour taste to sourdough and rye bread.

In cake mixes, Fumarate is used to maintain a low pH and prevent clumping of the flours used in the mix.

In fruit drinks, Fumarate is used to maintain a low pH which, in turn, helps to stabilize flavor and color.

Fumarate also prevents the growth of E. coli in beverages when used in combination with sodium benzoate.

When added to wines, Fumarate helps to prevent further fermentation and yet maintain low pH and eliminate traces of metallic elements.

In this fashion, Fumarate helps to stabilize the taste of wine.

Fumarate can also be added to dairy products, sports drinks, jams, jellies and candies.

Fumarate helps to break down bonds between gluten proteins in wheat and helps to create a more pliable dough.

Fumarate is used in paper sizing, printer toner, and polyester resin for making molded walls.

Food:

Fumarate has been used as a food acidulant since 1946.

Fumarate is approved for use as a food additive in the EU, USA and Australia and New Zealand.

As a food additive, Fumarate is used as an acidity regulator and can be denoted by the E number E297.

Fumarate is generally used in beverages and baking powders for which requirements are placed on purity.

Fumarate is used in the making of wheat tortillas as a food preservative and as the acid in leavening.

Fumarate is generally used as a substitute for tartaric acid and occasionally in place of citric acid, at a rate of 1 g of Fumarate 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, Fumarate 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 Fumarate is "practically non-toxic" but high doses are probably nephrotoxic after long-term use.

Medicine:

Fumarate 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.

Fumarate activates the Nrf2 antioxidant response pathway, the primary cellular defense against the cytotoxic effects of oxidative stress.

Widespread uses by professional workers:

Fumarate is used in the following products: laboratory chemicals, adhesives and sealants, plant protection products, inks and toners and pH regulators and water treatment products. Fumarate is used in the following areas: scientific research and development, building & construction work and agriculture, forestry and fishing. Fumarate is used for the manufacture of: machinery and vehicles, furniture and electrical, electronic and optical equipment. Release to the environment of Fumarate can occur from industrial use: as an intermediate step in further manufacturing of another substance (use of intermediates). Other release to the environment of Fumarate 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:

Fumarate is used in the following products: polymers, adhesives and sealants, coating products, pharmaceuticals, inks and toners and laboratory chemicals.

Fumarate has an industrial use resulting in manufacture of another substance (use of intermediates).

Fumarate is used in the following areas: formulation of mixtures and/or re-packaging and scientific research and development.

Fumarate is used for the manufacture of: chemicals.

Release to the environment of Fumarate 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:

Fumarate 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 Fumarate 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:

Fumarate is used in oral pharmaceutical formulations and food products, and is generally regarded as a relatively nontoxic and nonirritant material.

Fumarate preparations are used as long term and effective treatment of psoriasis.

Fumarate and Fumarate 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 Fumarate 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 Fumarate 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 Fumarate derivatives used.

In additional analyses, hypotheses were dealt with concerning the mechanism of action of Fumarate in psoriasis.

To establish Fumarate derivatives in the treatment of psoriasis, studies on chronic toxicity and pharmacokinetics will have to be conducted.

Further clinical trials should evaluate a single Fumarate derivative instead of mixtures.

Other uses:

Fumarate is used in the manufacture of polyester resins and polyhydric alcohols and as a mordant for dyes.

When Fumarate 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 Fumarate:

Physical Properties:

Fumarate mostly appears as a white-colored solid.

Fumarate has a fruit-like odor.

The molecular weight of Fumarate is 116 amu.

Fumarate is Combustible but Fumarate is difficult to start a fire.

Fumarate undergoes sublimation at 200 C.

The melting point of Fumarate is 572 to 576 °F.

Chemical Properties:

Fumarate is soluble in ethanol and concentrated sulfuric acid.

Fumarate is soluble in alcohol but is insoluble in benzene, water, and chloroform.

The capacity to absorb atmospheric moisture is very less.

The pH of Fumarate is 3.19

When Fumarate is heated in presence of Bayers reagent Fumarate gives rise to Racemic Tartaric Acid.

Characteristics of Fumarate:

One of Fumarate properties is to inhibit or block malolactic fermentation at a certain concentration.

Fumarate is therefore a tool of choice to limit the use of the SO2 previously used for this purpose.

Synthesis and Reactions of Fumarate:

Fumarate 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 Fumarate 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 Fumarate can be anticipated from Fumarate component functional groups.

This weak acid forms a diester, Fumarate undergoes additions across the double bond, and Fumarate is an excellent dienophile.

Fumarate 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 Fumarate:

The Fumarate formula, also named as Allomaleic acid formula is discussed in this article.

Fumarate is a dicarboxylic acid and a conjugate acid of Fumaric acid.

The molecular or chemical formula of Fumarate is C4H4O4.

Fumarate is a precursor to L-malate in the TCA cycle.

Fumarate 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 Fumarate:

Commercially, Fumarate 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, Fumarate 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 Fumarate.

The maleic acid concentration should be at least 30%.

Maleic acid is converted almost quantitatively by thermal or catalytic isomerization into the sparingly soluble Fumarate, 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 Fumarate obtained is purified by recrystallization from water, combined with purification by active charcoal.

Losses during purification are about 10%.

General Manufacturing Information of Fumarate:

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 Fumarate:

Tissue Locations:

Placenta

Prostate

Cellular Locations:

Extracellular

Membrane

Mitochondria

Biosynthesis and Occurrence of Fumarate:

Fumarate is produced in eukaryotic organisms from succinate in complex 2 of the electron transport chain via the enzyme succinate dehydrogenase.

Fumarate is one of two isomeric unsaturated dicarboxylic acids, the other being maleic acid.

In Fumarate the carboxylic acid groups are trans (E) and in maleic acid they are cis (Z).

Fumarate 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.

Fumarate 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 Fumarate when exposed to sunlight.

Fumarate is also a product of the urea cycle.

Handling and storage of Fumarate:

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 Fumarate:

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:

Fumarate 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 Fumarate:

Fumarate is "practically non-toxic" but high doses are probably nephrotoxic after long-term use.

First Aid Measures of Fumarate:

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 Fumarate:

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 Fumarate:

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 Fumarate:

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 Fumarate:

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=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+

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: 74.6Å²

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 Fumarate:

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 %

FUMARATE

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