Quick Search
Fumaric acid is found in fumitory (Fumaria officinalis), bolete mushrooms (specifically Boletus fomentarius var. pseudo-igniarius), lichen, and Iceland moss.
Fumaric acid 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.
CAS Number: 65997-04-8
Molecular Formula: C4H2O3
Molecular Weight: 98.05688
Synonyms: fumaric acid, 110-17-8, trans-Butenedioic acid, Allomaleic acid, fumarate, Boletic acid, Lichenic acid, (2E)-but-2-enedioic acid, Tumaric acid, 2-Butenedioic acid, trans-1,2-Ethylenedicarboxylic acid, (E)-2-Butenedioic acid, Allomalenic acid, But-2-enedioic acid, trans-2-Butenedioic acid, Fumaricum acidum, 2-Butenedioic acid, (E)-, Kyselina fumarova, 2-Butenedioic acid (E)-, USAF EK-P-583, Butenedioic acid, (E)-, FEMA No. 2488, Butenedioic acid, (2E)-2-butenedioic acid, (E)-but-2-enedioic acid, FuMaric acid anhydride
Fumaric acid is then converted by the enzyme fumarase to malate.
Human skin naturally produces fumaric acid when exposed to sunlight.
Fumaric acid is also a product of the urea cycle.
Click on genes, proteins and metabolites below to link to respective articles.
Fumaric acid is produced based on catalytic isomerisation of maleic acid in aqueous solutions at low pH.
Fumaric acid precipitates from the reaction solution.
Fumaric acid is accessible in large volumes as a hydrolysis product of maleic anhydride, produced by catalytic oxidation of benzene or butane.
Fumaric acid was first prepared from succinic acid.
Fumaric acid's uses as an additive span the manufacture of everything from pie llings and animal feed to medicines and even cleaning agents for bath salts and dentures.
Fumaric acid is also called trans-butenedioic acid, is a white solid.
Fumaric acid is an organic compound with the formula HO2CCH=CHCO2H.
A white solid, Fumaric acid occurs widely in nature.
The salts and esters are known as fumarates.
Fumarate can also refer to the C4H2O2−4 ion (in solution).
The trans isomer possesses a dipole moment.
Fumaric acid is an acid with the general formula C4H4O4.
Fumaric acid is found in seesaw (Fumaria ocinalis), bolete fungi (especially Boletus fomentarius var. Pseudo-igniarius), lichens, and Icelandic moss.
Fumaric acid occurs naturally in fruits and vegetables.
The food additive Fumaric acid is a colorless or white crystal, has no odor and a sharp sour taste.
Fumaric acid is derived from maleic acid (fermentation of sugar by fungi).
Fumaric acid is soluble in alcohol, slightly soluble in water and ether, slightly soluble in chloroform.
Fumaric acid, an unsaturated dicarboxylic acid.
Fumaric acid forms a white, crystalline powder and is only slightly soluble in water and organic solvents.
The water-soluble salts of Fumaric acid the fumarates, are formed with alkaline solutions.
With acids, malic acid is formed by water addition.
Fumaric acid is found abundantly in nature.
Fumaric acid has a slight acid taste.
Fumaric acid is free owing, stable and nonhygroscopic.
Fumaric acid is a white, odorless crystalline powder or granules.
Fumaric acid is soluble in alcohol, slightly soluble in water and in ether, and very slightly soluble in chloroform.
Used as an acidulant, Fumaric acid has bacteriostatic and antiseptic function.
Fumaric acid is a natural acid present in many fruits and vegetables.
Commercially made by fermentation of sugar by fungi or by chemical synthesis.
Fumaric acid is part of the metabolic pathway in every living cell.
Fumaric acid, the strongest organic food acid commonly used as a avoring agent and pH control agent.
Fumaric acid provides more sourness than other acidulants, e.g. citric acid (E330) and malic acid (E296) in food.
The European food additive number for Fumaric acid is E297.
Fumaric acid is a weak organic acid (a dicarboxylic acid) commercially made from maleic acid and with chemical formula C4H4O4.
Fumaric acid is a precursor for the production of other acids, like L-aspartic acid and L-malic acid.
Fumaric acid is a white or nearly white crystalline powder or granular with a clean, persistent sourness with dryness.
The sourness is around 1.5 times that of citric acid.
Fumaric acid is a weak organic acid containing two carboxylic acid functional groups and as a result Fumaric acid has two PKa values, PKa1 = 3.03 and PKa2 = 4.44.
Fumaric acid's PKa1 and PKa2 value is higher than that of citrate acid and malic acid.
Fumaric acid is an unsaturated di-carbonic acid and it has 2 dissociation equilibrium equations.
Fumaric acid's PH value is 2.03 in the concentration of 100 mM (0.1mol/L). (6)
The method to calculate Fumaric acid's PH is the same way with that of malic acid.
Fumaric acid is a relatively strong acid and has a strong buering property to maintain the pH of the aqueous solution at around 3.0, which is important for preservatives that function around pH 3.0.
Fumaric acid has a solubility of 0.5% (0.5g/100ml) at 20°C in water while citric, malic and tartaric acid are all very soluble in water.
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 avor impact.
Fumaric acid also decreases the pH with minimal added sourness in products with pHs greater than 4.5.
Fumaric acid's low molecular weight gives fumaric acid more buering capacity than other food acids at pHs near 3.O.
Because of Fumaric acid's strength, less fumaric acid is required when compared to other organic food acids, therefore reducing costs per unit weight.
Fumaric acid is a non-toxic food additive generally used in beverages and baking powders for which requirements are based on purity.
Fumaric acid is a substitute for tartaric acid and occasionally takes the place of citric acid, at a rate of 1.36 gram of citric acid to every 0.91 grams of Fumaric Acid for the same taste.
In maleic acid, carboxylic acid groups are in the cis (Z) form, and in Fumaric acid in the trans (E) form.
The E code for Fumaric acid is E297.
There are other pronunciations that refer to Fumaric acid.
Fumaric acid has names such as E297, Butenethioic Acid, Allomaleic Acid, Tumaric Acid, Lichenic Acid, Sodium Fumarate, Ammonium Fumarate.
Fumaric acid can be in the form of a white powder or in the form of transparent crystals.
Fumaric acid is odorless but has a fruity taste.
Fumaric acid is 1.5 times more sour and odorless than citric acid.
Fumaric acid is found in nature in the contents of bolete mushrooms, lichens, saber grass and Icelandic moss.
The form of Fumaric acid found in natural environments is colorless crystalline powder and white in ne form.
Fumaric acid also occurs in the human body as well as in plants.
Fumaric acid is known that the human body, which receives direct sunlight, produces fumaric acid.
Aromatically, Fumaric acid has a fruity taste.
Fumarate is used so that cells can store the energy we obtain from food in the form of adenosine triphosphate.
With this feature, Fumaric acid is one of the intermediate products in the citric acid cycle and the urea cycle.
Esters and salts are called fumarates.
Fumaric acid is known that dimethyl fumarate greatly inhibits the progression of multiple sclerosis.
Originally, Fumaric acid was isolated from plants belonging to the genus Fumaria, from which its name is derived.
Fumaric acid is an intermediate of the tricarboxylic acid cycle.
Fumaric acid is an organic acid found widely in nature.
Fumaric acid is a colorless, odorless, crystalline powder with tart-fruity taste.
Natural sources of Fumaric acid include bolete mushrooms, lichen, and Iceland moss.
Fumaric acid’s also found in papayas, pears and plums, but in very limited amounts.
Fumaric acid was rst isolated from the plant Fumaria ocinalis, which is where Fumaric acid derives its name.
Today, this acid is produced via chemical or enzymatic treatment of starchy materials.
Fumaric acid is the chemical compound with the formula HO2CCH=CHCO2H.
This colorless crystalline compound, Fumaric acid, is one of two isomeric unsaturated dicarboxylic acids, the other being maleic acid wherein the carboxylic acid groups are cis.
Fumaric acid has a fruit-like taste.
The salts and esters of fumaric acid are known as fumarates.
Fumaric acid, when added to food products, is denoted by E number E297.
Fumaric acid is found in fumitory (Fumaria ocinalis), bolete mushrooms (specically Boletus fomentarius var. pseudoigniarius), 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 adenylsuccinate 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 byproduct of the urea cycle.
In addition to its applications in food, Fumaric acid is also used in cosmetics, pharmaceuticals, and industrial products, including resins, coatings, and cleaning agents, owing to its chemical versatility.
Although fumaric acid is generally recognized as safe (GRAS) when used within regulated limits, consuming extremely high amounts might cause digestive irritation.
However, under normal use in food products, it poses minimal health risks and is widely approved for use in many countries, including by the European Food Safety Authority (EFSA) and the U.S. Food and Drug Administration (FDA).
A traditional synthesis involves oxidation of furfural (from the processing of maize) using chlorate in the presence of a vanadium-based catalyst.
Fumaric acid, the strongest organic food acid commonly used as a flavoring agent and pH control agent.
It provides more sourness than other acidulants, e.g. citric acid (E330) and malic acid (E296) in food.
The European food additive number for it is E297.
The chemical properties of fumaric acid can be anticipated from its component functional groups.
This weak acid forms a diester, it undergoes bromination across the double bond, and it is a good dienophile.
Chemical formula C4H4O4 is a compound in the category of trans-butene dioic acid, unsaturated carboxylic acids with crystals in the form of small prisms with open formula HO2CCH = CHCO2H.
Fumaric acid is also called ethylene dicarboxylic acid.
Fumaric acid coded E297, found in most vegetables and fruits and is a natural acid.
Fumaric acid is usually found in fungi and liver.
Fumaric acid is the (cis-) isomer of matureic acid.
Fumaric acid is White odorless granule or crystalline powder.
Less soluble in water and ether, soluble in alcohol and very little soluble in chloroform.
Fumaric acid is a compound with the chemical formula HO2CCH=CHCO2H and the CAS Number 110-17-8.
Fumaric acid is also referred to as trans-butenedioic acid, and its preferred IUPAC name is (2E)-But-2-enedioic acid.
Fumaric acid has a white crystalline form and occurs in the natural world.
Fumaric acid is key to organic acid biosynthesis in mammals and plays a critical role in plant life, and Fumaric acid can be naturally found in abundance in Iceland moss, lichen, and bolete mushrooms.
When Fumaric acid comes to sourness and titratable acidity — or TA — fumaric acid is one of the strongest food acids available.
Fumaric acid or trans-butenedioic 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 acids 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 often used in powdered drink mixes, baked goods, gelatin desserts, confectionery, and chewing gum, where it helps to enhance tartness, control pH, and extend shelf life by inhibiting the growth of harmful microorganisms.
Because of its low hygroscopicity (resistance to moisture absorption), it is especially valued in dry mix applications, where it remains stable over time without clumping or degrading.
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 the trans isomer of butenedioic acid, while maleic acid is the cis isomer.
Fumaric acid is a food additive that is commonly used as an acidity regulator, preservative, and flavor enhancer in a variety of processed foods and beverages.
Fumaric acid is the E number designation assigned to fumaric acid, a naturally occurring organic compound with the formula C₄H₄O₄, known for its strong acidic taste and stability in formulations.
Uses:
Fumaric acid is also added to leavening systems in baking, where it reacts with baking soda to produce carbon dioxide gas, helping to leaven and lighten the texture of cakes, cookies, and other baked products, while also adding a subtle tang to the flavor profile.
In processed meats, pickles, and sauces, fumaric acid serves as a preservative, extending the shelf life of the product by inhibiting the growth of molds, yeasts, and certain bacteria, which could otherwise lead to spoilage or foodborne illness.
In the pharmaceutical industry, Fumaric acid is used in the production of certain medicines, such as fumarate salts (e.g., dimethyl fumarate), which are used in treatments for conditions like multiple sclerosis and psoriasis.
These pharmaceutical formulations take advantage of fumaric acid's anti-inflammatory and immunomodulatory properties.
Within cosmetic formulations, Fumaric acid may be used in products like creams, lotions, and shampoos, where it can act as a pH adjuster or buffering agent, helping to maintain product stability and compatibility with the skin.
In the chemical and manufacturing sectors, Fumaric acid is involved in the production of resins and polyester compounds, where it is used as an intermediate in alkyd resins and unsaturated polyester resins, materials commonly used in the coating, construction, and automotive industries for their durability and strength.Fumaric acid is sometimes used in animal feed formulations, where it functions as an acidifier that helps to control intestinal pH in livestock, thus improving digestion and reducing pathogenic bacterial growth in the gut.
In the textile industry, Fumaric acid plays a role in dyeing and printing processes.
It acts as an acidic catalyst that helps the dyeing agents bind more effectively to the fabric, improving the colorfastness and stability of the dye, especially in wool and silk.
Fumaric acid is also used in the production of plasticizers.
These are compounds that are added to plastics to improve their flexibility, durability, and processability.
By incorporating fumaric acid into the manufacturing process, plastics such as PVC (polyvinyl chloride) become easier to handle and mold without compromising their performance.
In the paint and coating industries, Fumaric acid is used in the production of alkyd resins, which are employed to create high-quality paints and coatings.
These resins are essential for the production of weather-resistant and durable finishes, including those used in automotive coatings, industrial coatings, and protective coatings for buildings and infrastructure.
Fumaric acid serves as a key ingredient in electroplating solutions.
It is used to control the pH of plating baths, ensuring that metal plating processes, such as those involving nickel or copper, are efficient and produce smooth, uniform coatings on metallic surfaces.
In the agricultural sector, Fumaric acid is utilized in the production of herbicides and pesticides.
It functions as a buffering agent to help maintain the effectiveness and stability of these chemicals in various environmental conditions, making it easier to apply them in the field and ensuring that they remain active for longer durations.
Fumaric acid is used in biodegradable plastics production, particularly those based on polylactic acid (PLA).
In these applications, Fumaric acid can help enhance the thermal stability and mechanical properties of the plastics, making them suitable for eco-friendly packaging and other sustainable products that degrade naturally over time.
In water treatment processes, Fumaric acid is sometimes employed as an iron sequestrant or chelating agent.
It can help control the formation of scale and precipitates in water systems, ensuring that pipes, boilers, and industrial equipment operate efficiently by reducing the buildup of unwanted minerals.
Fumaric acid is also used in the production of certain lubricants for machinery and engines.
It can be incorporated into oil formulations as a viscosity modifier, improving the flow and efficiency of the oil while also contributing to the lubrication properties, which help reduce friction and wear in machinery.
Fumaric acid is sometimes used in the production of biofuels, specifically in the fermentation processes where it can act as a precursor for succinic acid, a compound used in the production of biodegradable plastics, solvents, and other green chemicals.
This makes it part of the effort to reduce the environmental footprint of chemical production.
Fumaric acid has been used as a food acidulant since 1946.
It is approved for use as a food additive in the EU, USA and Australia and New Zealand.
As a food additive, it 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.
It 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, it 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.
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.
Fumaric acid is used in the manufacture of polyester resins and polyhydric alcohols and as a mordant for dyes.
Fumaric acid can be used to make 6-methylcoumarin.
When fumaric acid is added to their feed, lambs produce up to 70% less methane during digestion.
Fumaric acid is primarily used as an acidity regulator and flavoring agent, where it enhances the tartness and sourness of foods and beverages, particularly in fruit-flavored products, carbonated drinks, gelatins, desserts, chewing gums, and baked goods.
Its sharp acidic taste and chemical stability make it ideal for dry mixes, where it resists moisture absorption and maintains its potency over long storage periods.
Safety Profile:
Fumaric acid, though biodegradable, can still have an environmental impact if improperly disposed of in large quantities.
When released into the environment, it can alter pH levels in soil or water, potentially affecting plant growth, aquatic life, and microbial ecosystems.
Proper disposal and containment procedures must be followed to minimize this risk.
In industrial settings, inhalation of fumaric acid dust over prolonged periods could potentially lead to respiratory sensitization.
This condition may increase the risk of developing asthma or other respiratory conditions in sensitive individuals, especially those working in areas without proper ventilation or dust control measures.
While rare, some individuals may experience allergic reactions to fumaric acid or its derivatives, especially when it is used in cosmetic products.
Symptoms of an allergic reaction could include skin rashes, itching, or even swelling in more severe cases.
It’s important to conduct a patch test when using products containing fumaric acid for the first time, particularly in individuals with sensitive skin.
In its powdered form, fumaric acid may be considered a potential fire hazard.
Fine powders suspended in the air can create a flammable dust cloud, which can be ignited by an open flame or sparks, leading to a fire or even an explosion in extreme cases.
Care should be taken when handling fumaric acid in environments with open flames or electrical equipment.
When mixed with certain chemicals or compounds, fumaric acid may undergo unintended chemical reactions that could produce toxic fumes or corrosive byproducts.
For example, mixing fumaric acid with strong bases or oxidizing agents could lead to hazardous conditions, including the release of toxic gases or excessive heat.
Fumaric acid can cause irritation to the eyes, skin, and respiratory system.
Direct contact with the acid may lead to burns, redness, or discomfort on the skin, and it can cause stinging or watering of the eyes.
Inhalation of the dust or fumes may result in coughing, sneezing, or a scratchy throat, especially in poorly ventilated environments.
While fumaric acid is used safely in food and cosmetics, large amounts of the substance can be toxic.
Ingesting excessive quantities of fumaric acid can lead to gastrointestinal distress, including symptoms such as nausea, vomiting, and diarrhea.
In severe cases, it could lead to more serious metabolic imbalances or systemic toxicity.
Fumaric acid, in its concentrated form, can be corrosive to certain materials, including metals and fabrics.
Fumaric acid may cause damage to surfaces it comes in contact with, particularly in high-concentration solutions used in industrial applications.
Special precautions must be taken to avoid spills and direct contact with the skin and eyes.
