PRODUCTS

ALLOMALEIC ACID

Allomaleic acid is a white crystalline organic compound widely found in nature and used as a food additive.
Allomaleic acid is the trans isomer of butenedioic acid and is an intermediate in the citric acid cycle, crucial for energy production in cells.
The salts and esters of Allomaleic acid are known as fumarates, and it can be used to control malolactic fermentation in wines, as well as in the production of various industrial products.

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]

Allomaleic acid is an organic compound with the formula HO2CCH=CHCO2H.
A white solid, Allomaleic acid occurs widely in nature.

Allomaleic acid has a fruit-like taste and has been used as a food additive.
Allomaleic acid E number is E297.

The salts and esters are known as fumarates.
Fumarate can also refer to the C4H2O2−4 ion (in solution).
Allomaleic acid is the trans isomer of butenedioic acid, while maleic acid is the cis isomer.

Allomaleic acid can be prepared by fermentation by employing Rhizopus species.
Recently, industrial-scale synthesis of Allomaleic acid from renewable feedstocks and lignocellulosic biomass has been proposed

Allomaleic acid is an organic compound (this means Allomaleic acid consists of carbon).
The chemical formula of Allomaleic acid is C4H4O4.

Allomaleic acid is mostly found in Allomaleic acid solid state and is white in color.
Allomaleic acid has a fruit-like taste.

Allomaleic acid is also known as Fumaric acid.
Allomaleic acid is a dicarboxylic acid.

Allomaleic acid is widely used as a food additive.
Even the human skin produces Allomaleic acid when Allomaleic acid is exposed to sunlight.

Allomaleic acid is a by-product of the urea cycle in human beings.
The salts and esters of Allomaleic 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.

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

Allomaleic acid is a butenedioic acid in which the C=C double bond has E geometry.
Allomaleic acid is an intermediate metabolite in the citric acid cycle.

Allomaleic acid has a role as a food acidity regulator, a fundamental metabolite and a geroprotector.
Allomaleic acid is a conjugate acid of a fumarate(1-).

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

Allomaleic acid or trans-butenedioic acid, is a white crystalline chemical compound widely found in nature.
Allomaleic acid is a key intermediate in the tricarboxylic acid cycle for organic acid biosynthesis in humans and other mammals.
Allomaleic acid is also an essential ingredient in plant life.

When used as a food additive, the hydrophobic nature of Allomaleic 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.
Allomaleic acid low molecular weight gives Allomaleic acid more buffering capacity than other food acids at pHs near 3.O.

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

Allomaleic acid (C4H4O4) is an organic acid widely found in nature, and is a component of organic biosynthesis is humans.
Chemically, Allomaleic acid is an unsaturated dicarboxylic acid.

Allomaleic acid exists as white or nearly white crystals, odorless with a very tart taste.
Allomaleic acid is generally nontoxic and nonirritant.

Allomaleic acid has been used in food and beverage products since the 1940s.
Food research shows that Allomaleic acid can improve quality and reduce the costs of many food and beverage products.

Allomaleic acid is non-hygroscopic (absorbs no moisture).
In the cosmetic industry, Allomaleic acid is used as a bath salt cleaning agent for dentures.

Allomaleic acid also is used in animal feeds.
Allomaleic 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 Allomaleic acid, and was approved in 2013 for use in multiple sclerosis.

Allomaleic acid is obtained from the transformation of maleic anhydride or maleic acid solutions resulting from the isomerization process (washing) of phthalic anhydride.
Allomaleic acid application areas are unsaturated polyester resins, the acidifying animal feed and plasticized products.

Allomaleic acid is an important specialty chemical with wide industrial applications ranging from Allomaleic acid use as feedstock for the synthesis of polymeric resins to acidulant in foods and pharmaceuticals.
Currently, Allomaleic 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 Allomaleic acid from renewable resources.

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

Filamentous fungal fermentation is also difficult to operate because of Allomaleic 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.

Allomaleic acid attenuates the eotaxin-1 expression in TNF-α-stimulated fibroblasts by suppressing p38 MAPK-dependent NF-Κb signaling.
Allomaleic 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.
Allomaleic acid oncogenic action appears due to Allomaleic acid ability to inhibit prolyl Hydroxylase-containing enzymes.

Allomaleic 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.

Allomaleic acid is an organic compound with the formula (COOH)CH=CH(COOH).
A white solid, Allomaleic acid occurs widely in nature.

Allomaleic acid has a fruit-like taste and has been used as a food additive.
Allomaleic acid E number is E297.

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

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

Production by chemical synthesis is the most common:
Allomaleic 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.
Allomaleic acid involves the fermentation by Rhizopus oryzae, in particular, of agri-food residues (e.g. from apples).

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

Applications of Allomaleic acid:
Allomaleic acid has been used as a standard for the quantitative determination of phenolic compounds in nettle samples by HPLC.
Allomaleic acid may be used in the preparation of L-Lysine-Allomaleic acid crystals.
Allomaleic acid may also be employed for the industrial manufacture of synthetic resins and eco-friendly/biodegradable polymers.

When used in wine, Allomaleic 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), Allomaleic acid blocks all malolactic fermentation.

Added during malolactic fermentation, Allomaleic acid allows the fermentation to be partially completed.
Allomaleic acid is a tool of great interest when you wish to limit [the use of SO2] or make wines without SO2.

Uses of Allomaleic acid:
The esters of Allomaleic acid are used for the treatment of psoriasis due to the antioxidants and anti-inflammation properties.
Allomaleic acid is used as a food additive.

Allomaleic acid helps preserve the taste and quality of the food products due to the low water absorption capacity of the Allomaleic acid.
Allomaleic acid is used by pharmacies to produce ferrous fumarate and alexipharmic.
Allomaleic acid is used in the production of Tartaric acid.

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

Allomaleic acid is an essential biochemical in the cellular respiration of plants and animals.
Allomaleic acid is used as a fortifier (paper size resins, unsaturated polyester resins, and alkyd surface coating resins), food antioxidant, dye mordant, and medication.

Allomaleic acid is also used in dentifrices (stain remover) and to make other chemicals.
Allomaleic acid is used in rosin esters and adducts, drying oils, printing inks, and foods (acidulant and flavoring agent).

Allomaleic acid is used primarily in liquid pharmaceutical preparations as an acidulant and flavoring agent.
Allomaleic acid may be included as the acid part of effervescent tablet formulations, although this use is limited as Allomaleic acid has an extremely low solubility in water.

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

Allomaleic acid has also been investigated as an alternative filler to lactose in pellets.
Allomaleic acid has been investigated as a lubricant for effervescent tablets, and copolymers of Allomaleic acid and sebacic acid have been investigated as bioadhesive microspheres.

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

Allomaleic acid is naturally produced by the body, however for industrial applications Allomaleic acid is synthesized chemically.
Allomaleic acid is used to impart a tart taste to processed foods.

Allomaleic acid is also used as an antifungal agent in boxed foods such as cake mixes and flours, as well as tortillas.
Allomaleic acid is also added to bread to increase the porosity of the final baked product.

Allomaleic acid is used to impart a sour taste to sourdough and rye bread.
In cake mixes, Allomaleic acid is used to maintain a low pH and prevent clumping of the flours used in the mix.

In fruit drinks, Allomaleic acid is used to maintain a low pH which, in turn, helps to stabilize flavor and color.
Allomaleic acid also prevents the growth of E. coli in beverages when used in combination with sodium benzoate.

When added to wines, Allomaleic acid helps to prevent further fermentation and yet maintain low pH and eliminate traces of metallic elements.
In this fashion, Allomaleic acid helps to stabilize the taste of wine.

Allomaleic acid can also be added to dairy products, sports drinks, jams, jellies and candies.
Allomaleic acid helps to break down bonds between gluten proteins in wheat and helps to create a more pliable dough.
Allomaleic acid is used in paper sizing, printer toner, and polyester resin for making molded walls.

Food:
Allomaleic acid has been used as a food acidulant since 1946.
Allomaleic acid is approved for use as a food additive in the EU, USA and Australia and New Zealand.

As a food additive, Allomaleic acid is used as an acidity regulator and can be denoted by the E number E297.
Allomaleic acid is generally used in beverages and baking powders for which requirements are placed on purity.

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

Medicine:
Allomaleic 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.
Allomaleic acid activates the Nrf2 antioxidant response pathway, the primary cellular defense against the cytotoxic effects of oxidative stress.

Widespread uses by professional workers:
Allomaleic 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. Allomaleic acid is used in the following areas: scientific research and development, building & construction work and agriculture, forestry and fishing. Allomaleic acid is used for the manufacture of: machinery and vehicles, furniture and electrical, electronic and optical equipment. Release to the environment of Allomaleic 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 Allomaleic 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:
Allomaleic acid is used in the following products: polymers, adhesives and sealants, coating products, pharmaceuticals, inks and toners and laboratory chemicals.
Allomaleic acid has an industrial use resulting in manufacture of another substance (use of intermediates).

Allomaleic acid is used in the following areas: formulation of mixtures and/or re-packaging and scientific research and development.
Allomaleic acid is used for the manufacture of: chemicals.
Release to the environment of Allomaleic 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:
Allomaleic 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 Allomaleic 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:
Allomaleic acid is used in oral pharmaceutical formulations and food products, and is generally regarded as a relatively nontoxic and nonirritant material.

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

Allomaleic acid and Allomaleic 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 Allomaleic 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 Allomaleic 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 Allomaleic acid derivatives used.

In additional analyses, hypotheses were dealt with concerning the mechanism of action of Allomaleic acid in psoriasis.
To establish Allomaleic 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 Allomaleic acid derivative instead of mixtures.

Other uses:
Allomaleic acid is used in the manufacture of polyester resins and polyhydric alcohols and as a mordant for dyes.
When Allomaleic 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 Allomaleic acid:

Physical Properties:
Allomaleic acid mostly appears as a white-colored solid.
Allomaleic acid has a fruit-like odor.

The molecular weight of Allomaleic acid is 116 amu.
Allomaleic acid is Combustible but Allomaleic acid is difficult to start a fire.

Allomaleic acid undergoes sublimation at 200 C.
The melting point of Allomaleic acid is 572 to 576 °F.

Chemical Properties:
Allomaleic acid is soluble in ethanol and concentrated sulfuric acid.
Allomaleic 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 Allomaleic acid is 3.19
When Allomaleic acid is heated in presence of Bayers reagent Allomaleic acid gives rise to Racemic Tartaric Acid.

Characteristics of Allomaleic acid:
One of Allomaleic acid properties is to inhibit or block malolactic fermentation at a certain concentration.
Allomaleic acid is therefore a tool of choice to limit the use of the SO2 previously used for this purpose.

Synthesis and Reactions of Allomaleic acid:
Allomaleic 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 Allomaleic 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 Allomaleic acid can be anticipated from Allomaleic acid component functional groups.
This weak acid forms a diester, Allomaleic acid undergoes additions across the double bond, and Allomaleic acid is an excellent dienophile.

Allomaleic 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 Allomaleic acid:
The Allomaleic acid formula, also named as Fumaric acid formula is discussed in this article.
Allomaleic acid is a dicarboxylic acid and a conjugate acid of fumarate.
The molecular or chemical formula of Allomaleic acid is C4H4O4.

Allomaleic acid is a precursor to L-malate in the TCA cycle.
Allomaleic 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 Allomaleic acid:
Commercially, Allomaleic 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, Allomaleic 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 Allomaleic 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 Allomaleic 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 Allomaleic acid obtained is purified by recrystallization from water, combined with purification by active charcoal.
Losses during purification are about 10%.

General Manufacturing Information of Allomaleic 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 Allomaleic acid:

Tissue Locations:
Placenta
Prostate

Cellular Locations:
Extracellular
Membrane
Mitochondria

Biosynthesis and Occurrence of Allomaleic acid:
Allomaleic acid is produced in eukaryotic organisms from succinate in complex 2 of the electron transport chain via the enzyme succinate dehydrogenase.
Allomaleic acid is one of two isomeric unsaturated dicarboxylic acids, the other being maleic acid.
In Allomaleic acid the carboxylic acid groups are trans (E) and in maleic acid they are cis (Z).

Allomaleic 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.
Allomaleic 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 Allomaleic acid when exposed to sunlight.
Fumarate is also a product of the urea cycle.

Handling and storage of Allomaleic 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 Allomaleic 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:
Allomaleic 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 Allomaleic acid:
Allomaleic acid is "practically non-toxic" but high doses are probably nephrotoxic after long-term use.

First Aid Measures of Allomaleic 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 Allomaleic 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 Allomaleic 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 Allomaleic 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 Allomaleic 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: 74.6Å²
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 Allomaleic 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 %

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BAPTA-AM

Related Compounds of Allomaleic 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