Fumaric Acid
Fumaric acid is used in the production of many industrial materials, including unsaturated polyester, alkyd resins, printing inks, and paper sizing.
Fumaric acid is applied as an ingredient in creams, lotions, and ointments, where it functions as a pH adjuster, buffering agent, and skin-conditioning agent.
Fumaric acid is also widely used in the food industry as an acidulant because it is non-toxic and the least expensive food-grade acid.
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 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 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.
Applications
Fumaric acid has been used in food and beverage products since 1946.
It is currently used in wheat and corn tortillas, sourdough and rye bread, refrigerated biscuit doughs, fruit juice and nutraceutical drinks, gelatin desserts, gelling aids, pie fillings, and wine.
Fumaric acid is also used in animal feed.
Fumaric acid is an acidulant that possesses a fruit-like flavor.
Fumaric acid (E297 or INS297) is a four-carbon dicarboxylic acid and is used as an acidity regulator in foo.d
Fumaric Acid is a non-toxic food additive generally used in beverages and baking powders for which requirements are based on purity.
It is a substitute for tartaric acid and occasionally takes the place of citric acid at a rate of 1.36 grams of citric acid to every 0.91 grams of Fumaric Acid for the same taste.
It is also an essential ingredient in candy manufacturing to add sourness, similar to how malic acid is used.
Fumaric acid has been used in food and beverage products for almost a century.
It is most commonly relied on to improve quality and reduce the costs of many food, beverage, and animal feed products.
It is also more substantial than other acids, enabling fewer products to achieve the same results–thereby improving economies by lowering ingredient costs.
Bakery
Bread
Fumaric acid acts as an instant flavoring agent for rye and sourdough bread.
Fumaric acid is added to dough ingredients during the dry blending step.
Flavor intensity is easily controlled by the amount of Fumaric acid added to the recipe.
In English muffins, Fumaric acid significantly increases porosity. Dough machinability is improved, and more sourness is provided per unit weight.
From the tart, warm flavor of a sourdough roll to a longer-lasting tortilla, fumaric acid extends shelf life, improves dough machinability, and acts as a flavoring agent for various savory baked goods.
Dry Mixes.
Chocolate cakes, gel desserts, brownies, and pancakes made from dry mixes stay dry and free-flowing because fumaric acid prevents caking and drying even in high-humidity storage conditions.
Fruit Juice Drinks
Fumaric acid provides more sourness per unit weight than other acidulants used in fruit juice drinks.
This substantially reduces the acidulant cost.
In fruit juice drinks, Fumaric acid provides more buffering capacity than other acidulants when the pH is near 3.0.
Using fumaric acid helps stabilize the pH of a fruit juice drink, stabilizing color and flavor.
Wine
Fumaric Acid can economically acidify wine with no detectable difference in flavor.
The replacement ratio of three pounds of fumaric acid to five pounds of Citric acid can significantly reduce acidulant cost.
Fumaric acid also prevents secondary fermentation after bottling and can act as a clarifier when low concentrations of copper and iron are present.
Confectioneries
Fumaric acid extends the shelf life of acid-coated candies because it does not absorb moisture during storage and distribution.
Maintaining a low moisture level retards sucrose inversion.
Acidulant cost is also reduced as fumaric acid provides more sourness per unit weight than other acidulants used in dry form.
Jellies and Jams
Fumaric acid can cut food acid costs when used as an acidulant for jams, jellies, and preserves.
As little as two pounds of fumaric acid can replace every three pounds of Citric, Malic, or Tartaric acid.
At the 2:3 replacement ratio, fumaric acid does not produce significant gel strength or pH differences.
Alginate Based Desserts
Fumaric acid is an economical acidulant that liberates calcium. It improves smoothness and optimizes setting times.
Also, the non-hygroscopicity of fumaric acid means that dry dessert mixes remain free-flowing, even in high humidity.
Fumaric acid can be added directly to dry dessert mixes during the manufacturing process without causing degradation of flavor ingredients because of its non-hygroscopic nature.
Gelatin Desserts
Fumaric acid significantly reduces acidulant costs in gelatin desserts.
Depending on the product recipe, each pound of Citric acid can be replaced with 0.6 to 0.7 pounds of fumaric acid.
Reducing moisture pick-up improves flavor stability and lengthens shelf life.
Fumaric acid maintains non-caking and free-flowing qualities.
By keeping the moisture content low, fumaric acid helps maintain flavor components’ stability and markedly decreases the inversion of sucrose in the packaged dry mix.
Using less expensive packaging may also be possible if other moisture-sensitive ingredients are not used in the formulation.
Fumaric acid also increases gel strength, so food processors may reduce average gelatin content by about 2%.
Confectionery
Fumaric acid does not absorb moisture during storage and distribution, keeping sweets on the shelf longer by extending shelf life and slowing sucrose inversion.
Because fumaric acid provides more sourness per unit weight than other dry acidulants, it can also help confectioners seeking to reduce costs.
Pie Fillings
Fumaric acid can be mixed directly with the starch and sugar ingredients in pie fillings, as it is non-hygroscopic.
Fumaric acid lowers costs by reducing the food acid needed in product formulations.
Fumaric acid improves smoothness and extends the critical cook times for optimum gelation.
Egg White Foams
Fumaric acid can promote maximum volume in egg-white foams and end products based on egg-white foams.
Fumaric acid can replace the more expensive cream of tartar to control egg-white volume.
With Fumaric acid, egg whites can be overbeaten for as much as double the customary optimum time.
Well suited for continuous flow processes, fumaric acid can be added to liquid and dried egg whites.
Jellies, Jams, & Desserts
Fumaric acid improves jellies, jams, preserves, and desserts by providing better texture and gelling properties, increasing flavor stability and lengthening shelf life.
Additionally, in egg white foams and applications that use egg white foams, fumaric acid increases volume and replaces cream of tartar, delivering cost efficiencies.
WEIN
Fumaric acid enables the control of malolactic fermentation when it is used in wine.
When added at an early stage after the end of alcoholic fermentation (fructose/glucose under 1 g/L), fumaric acid blocks all malolactic fermentation.
During malolactic fermentation, fumaric acid allows the fermentation to be partially completed.
It is a tool of great interest to limit [the use of SO2] or make wines without SO2.
Note: However, proceed with caution when using in wines with residual sugar: in the case of alcoholic refermentation, the yeast may metabolize the fumaric acid that is added and turn it into malic acid using its Krebs cycle.
As a result, there is a risk of activating the malolactic fermentation instead of inhibiting it
All of these interesting aspects
make it suitable for all vinification operations in which sulfur levels must be contained.
For instance, it is ideal for making sparkling wine bases and delicate white, rosé, or red wines for those seeking the pleasant taste that malic acidity offers.
When dosed as recommended, it causes a reduction in pH of approximately 1 to 2 tenths, depending on the wine’s buffer capacity, and increases total acidity compared to what would happen if tartaric acid were added.
However, according to current legislation, it is not classified as an acidifier, meaning it can be used even though it is not included in the relevant register.
The effect of FUMARIC ACID persists for as long as the molecule is present in the medium; for example, it has been observed to last for many months when added to
wine once the fermentation process is complete, during refinement without Saccharomyces cerevisiae activity.
Before using FUMARIC ACID, orientation tests should be carried out in the laboratory to predict its effects on the sensory balance of the wine.
FUMARIC ACID is the perfect comp
Beverages
A sweet, delicious fruit juice stays colorful and flavorful longer with the addition of fumaric acid to control pH.
Fumaric acid also helps acidify wine with no detectable difference in flavor and prevents secondary fermentation after bottling.
Cleaning Agents for Dentures/Bath Salts
The carbon dioxide-generating compounds containing NaHCO3, K2CO3, and powdered Fumaric acid can be tableted with other ingredients to make cleaning agents for dentures and bath salts.
Animal Feed
Fumaric acid has proven to be a particularly effective additive to piglet feed post-weaning.
Including Fumaric acid and the resultant adjustment of the pH value demonstrate improved weight gain, food consumption, and feed conversion ratio.
Animal Nutrition.
A proven, effective additive in piglet feed, fumaric acid is shown to improve weight gain, food consumption, and feed conversion ratio during the post-weaning period.
Personal Care & Cosmetics.
The effervescence of personal care and cosmetic products comes from combined powdered fumaric acid and carbon dioxide ingredients combined and tableted.
Fumaric acid finds application in cosmetic formulations and personal care products.
Fumaric acid is applied as an ingredient in creams, lotions, and ointments, where it functions as a pH adjuster, buffering agent, and skin-conditioning agent.
Fumaric acid is used in cleaning products, such as detergents and dishwashing liquids.
Fumaric acid aids in removing dirt, stains, and scale deposits due to its acidic properties.
Industrial Uses
Industrial uses of Fumaric acid include:
Unsaturated Polyester
Alkyd Resins
Printing Inks
Paper Sizing
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 acts as a crosslinking agent and helps enhance the properties of these resins, including their strength, durability, and heat resistance.
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
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WAXES
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Polyalphaolefin (PAO)
Polybutene
Polyester polyols
Polyisobutylene (PIB)
Propylene-ethylene copolymers
Styrene block copolymers
ADDITIVES
Adipic Acid
Di-pentaerythritol
Alcohol Ester
Fumaric acid
Hide glue
Rubber additives
Bone glue
Maleic Acid Anhydride
Melamine
Microspheres
Pentaerythritol
Sebacic Acid
Silanes
Triacetin
UV stabilizers
Zinc oxide
OILS
Adipic Acid
WAXES
Amide wax
EVA wax
Fischer-Tropsch wax
HDPE waxes
Montan wax
Paraffin wax
PE wax
PP wax
PTFE waxes
Wax blends
BINDERS
Gum rosin
Rosin esters
Modified gum rosin
Phenolic resin
Polymer dispersions
Polyvinyl alcohol
Polyvinyl butyral
Tall oil rosin
RESINS
Gum rosin
Gum rosin dispersions
Epoxy Resins
Rosin esters
Hydrocarbon resin
Modified gum rosin
Phenolic resin
Shellac resin
Tall oil rosin
Wood resin
RUBBERS
Butyl rubber (IIR)
Natural rubber (NR)
Polybutadiene Rubbers
Polyisoprene rubber (IR)
CASEINES
Casein, technical
EMULSIFIERS
Polyetheramines
POLYGLYCOLS
Polyetheramines
Polyethylene glycol
SURFACTANTS
Polyetheramines
POLYVINYL ALCOHOL
Polyvinyl alcohol
Polyvinylpyrrolidon (PVP)
COLORANTS
Titanium dioxide – White pigments
FOOD ADDITIVES
Triacetin
Ammonium fumarate
Ascorbic Acid
Citric Acid Anhydrous
Crotonic acid
Dimethyl fumarate
Fumaronitrile
Fumaryl chloride
Glutathione
Iron(II) fumarate
Maleic acid
Malic Acid
Malic Acid
Potassium Citrate
Related compounds
Sodium Ascorbate
Sodium Citrate
Succinic acid
Vitamin A Palmitate
Zinc Sulfate