Fumaric Acid
Fumaric acid is an organic compound with the formula HO2CCH=CHCO2H.
Fumaric acid is an organic acid that serves various functions, including enhancing taste, managing pH, reducing hygroscopicity, improving shelf stability, and more. Fumaric acid is a functional ingredient applicable across food, beverage, animal nutrition, industrial, pharmaceutical, and personal care markets.
Fumaric acid is a valuable compound used in foods, beverages, detergents, animal feed, pharmaceuticals, and miscellaneous industrial products.
Fumaric acid is a food additive used as an anti-oxidant to keep moisture from hardening food powders.
Fumaric acid is also used in coatings, resins, pharmaceuticals, and plasticizers applications.
A white solid, fumaric acid occurs widely in nature.
EC / List no.: 203-743-0
CAS no.: 110-17-8
Mol. formula: C4H4O4
Synonyms: (E)-Butenedioic acid, trans-1,2-Ethylenedicarboxylic acid, trans-butene-dioic acid 2-Butenedioic acid, Allomaleic acid, Boletic acid, Donitic acid, Lichenic acid
Fumaric acid derives its name from being found in plants belonging to the genus Fumaria, a common European herb.
Fumaric acid is the trans-isomer of symmetric, unsaturated dicarboxylic acid; the cis-isomer is maleic acid.
Fumaric acid is produced as a colorless, crystalline powder with a fruit-like taste (a fruit acid), and it is a weak acid that forms diesters, has low solubility in water, and undergoes additions across the double bond.
Fumaric acid is widely used in the food industry as an acidulant because it is non-toxic and the least expensive food-grade acid.
Fumaric acid solubility in water is low (0.6 g per 100 g at 25 °C), and, therefore, to increase its application in various foods, a cold-water-soluble (CWS) fumaric acid, which contains a wetting agent, for example, 0.3% w/w dioctyl sodium sulfosuccinate, is used.
Fumaric acid is a critical intermediate in the tricarboxylic acid cycle for organic acid biosynthesis in humans and other mammals.
Fumaric acid is also an essential ingredient in plant life.
When used as a food additive, the hydrophobic nature of fumaric acid results in persistent, long-lasting sourness and flavor impact.
Industrial uses of Fumaric acid include unsaturated Polyesters, Alkyd Resins, Printing Inks and Paper Sizing. Fumaric acid acts as a crosslinking agent and helps enhance the properties the resins, including their strength, durability, and heat resistance.
Industrial Manufacturing
Fumaric acid is used in the production of many industrial materials, including unsaturated polyester, alkyd resins, printing inks, and paper sizing.
Fumaric acid is used to manufacture unsaturated polyester resins(UPR), alkyd resins, and plasticizers.
Fumaric acid is employed in the production of unsaturated polyester resins (UPR) and alkyd resins.
Fumaric Acid, in the form of a colorless fluid, is produced by the isomerization of maleic acid.
This product can be used in paper sizing and in glues.
Fumaric Acid is sometimes known as 2-Butendioic acid and can also be used in synthetic resins, unsaturated polyester resins, and in lubricants.
The versatile compound also decreases the pH with minimal added sourness in products with pHs more than 4.5.
Its low molecular weight gives fumaric acid more buffering capacity than other food acids at pHs near 3.0.
Because of its strength, less fumaric acid is required than other organic food acids, reducing costs per unit weight.
Fumaric acid is used for the industrial preparation of l-malic acid catalyzed by the enzyme fumarase (see ‘Malic acid’) and l-aspartic acid, a component of aspartame, by the enzyme aspartase.
Other industrial uses of fumaric acid are in jet printing inks, plastic surface coating, and paper sizing, and as an intermediate in preparing unsaturated polyester and alkyd resins.
The pharmaceutical industry uses fumaric acid to produce alexipharmic sodium dimercaptosuccinate and ferrous fumarate, as an optical bleaching agent, in formulations for alternative medicine, or as fumaric acid esters monoethyl fumarate and dimethyl fumarate to treat psoriasis.
Fumaric acid occurs naturally, albeit in limited amounts, in such fruits as papayas, pears, and plums.
In the United States, fumaric acid is used principally in fruit juices, gelatin desserts, tortillas, and pie fillings.
Fumaric acid is relatively cheap but has the disadvantage of a more pungent taste than citric acid and is difficult to dissolve in water.
The solubility of fumaric acid is only ∼6 g l−1 (i.e., 0.6%), which is further complicated by the extended times necessary for solubility concentrations to go into the solution. For this reason, solubility is often hastened by heating the solvent, which frequently precludes its use for many food industry applications.
Fumaric acid is a butenedioic acid with an E geometry of the C=C double bond.
Fumaric acid is an intermediate metabolite in the citric acid cycle.
Fumaric acid is a food acidity regulator and a fundamental metabolite
Fumaric acid is a conjugate acid of a fumarate(1-).
It has a fruit-like taste and has been used as a food additive.
Its E number is E297.
Fumaric acid is used as a food acidulant in beverages and baking powders.
Furthermore, fumaric acid is a pharmaceutically active substance that is used to treat psoriasis or multiple sclerosis
The salts and esters are known as fumarates.
The fumaric acid esters (FAE) monoethyl fumarate (MEF) and dimethyl fumarate (DMF) are chemical compounds derived from the base compound fumaric acid.
Fumaric acid is the trans isomer of butenedioic acid, while maleic acid is the cis isomer.
Fumaric acid is a valuable intermediate in several chemical syntheses, including esterification and polymerization, and in the manufacture of sizing resins for the paper industry
Preferred IUPAC name: (2E)-But-2-enedioic acid
Other names
Fumaric acid
trans-1,2-Ethylenedicarboxylic acid
2-Butenedioic acid
trans-Butenedioic acid
Allomaleic acid
Boletic acid
Donitic acid
Lichenic acid
Identifiers
CAS Number: 110-17-8
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)[2]
Solubility in water: 4.9 g/L at 20 °C[1]
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
Fumaric acid has been used as a food acidulant since 1946.
As a food additive, it is used as an acidity regulator and can be denoted by the E number E297.
It is generally used in beverages and baking powders for which requirements are placed on purity.
Fumaric acid is used in making wheat tortillas as a food preservative and leavening acid.
Fumaric acid increases the gel strength of gelatines and acts as a calcium ion liberator when incorporated in alginate preparations.
It blends readily with other food acidulants and does not give a burst of acidic taste.
Although fumaric acid does not have exceptional flavor-blending characteristics, it shows an affinity for specific flavoring agents like those in grapes by producing an aftertaste that supplements the overall flavor.
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, to add sourness, similarly to how 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 2014 that fumaric acid is "practically non-toxic," but high doses are probably nephrotoxic after long-term use.
Medicine
Fumaric acid was developed as a medicine to treat psoriasis autoimmune condition in the 1950s in Germany as a tablet containing 3 esters, primarily dimethyl fumarate, and marketed as Fumaderm by Biogen Idec in Europe.
Other uses
Fumaric acid is used to manufacture polyester resins and polyhydric alcohols, and as a mordant for dyes.
When fumaric acid is added to their feed, lambs produce up to 70% less methane during digestion.
Synthesis and reactions
Fumaric acid was first prepared from succinic acid.
A traditional synthesis involves the oxidation of furfural (from the processing of maize) using chlorate in the presence of a vanadium-based catalyst.
Currently, industrial synthesis of fumaric acid is mainly based on catalytic isomerization 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 benzene or butane catalytic oxidation.
The chemical properties of fumaric acid can be anticipated from its component functional groups.
This weak acid forms a diester, undergoes additions across the double bond, and is an excellent dienophile.
Fumaric acid does not combust in a bomb calorimeter under conditions where maleic acid deflagrates smoothly.
For teaching experiments designed to measure the difference in energy between the cis- and trans-isomers, an estimated quantity of carbon can be ground with the subject compound, and the enthalpy of combustion computed by difference.
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
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
