PRODUCTS

FUMARIC ACID

CAS NUMBER: 110-17-8

EC NUMBER: 203-743-0

MOLECULAR FORMULA: COOH-CH=CHCOOH

MOLECULAR WEIGHT: 116.07

IUPAC NAME: (E)-but-2-enedioic acid

Fumaric Acid is an organic compound with the formula HO2CCH=CHCO2H.
Fumaric Acid is 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 Acid's 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 the trans isomer of butenedioic acid, while maleic acid is the cis isomer.

Biosynthesis and Occurrence:
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 one of two isomeric unsaturated dicarboxylic acids, the other being maleic acid.

In Fumaric Acid the carboxylic acid groups are trans (E) and in maleic acid they are cis (Z).
Fumaric 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.
Fumaric 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 Fumaric Acid when exposed to sunlight.
Fumarate is also a product of the urea cycle.

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

As a food additive, Fumaric Acid 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.
Fumaric Acid 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.

*Medicine:
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.

*Other Uses:
Fumaric Acid is used in the manufacture of 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 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 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 Fumaric Acid can be anticipated from its component functional groups.
This weak acid forms a diester, it undergoes additions across the double bond, and it 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, a measured quantity of carbon can be ground with the subject compound and the enthalpy of combustion computed by difference.

Fumaric Acid is an important specialty chemical with wide industrial applications ranging from its use as feedstock for the synthesis of polymeric resins to acidulant in foods and pharmaceuticals.
Fumaric 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.
Fumaric Acid is used to make paints and plastics, in food processing and preservation, and for other uses.

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

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

Fumaric Acid is stable although it is subject to degradation by both aerobic and anaerobic microorganisms.
When heated in sealed vessels with water at 150 - 170 °C it forms DL-malic acid.

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 flavor impact.

The versatile compound 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 buffering capacity than other food acids at pHs near 3.O.

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.
Fumaric Acid is also an essential ingredient in the manufacturing of candy to add sourness, similar to the way malic acid is used.

APPLICATIONS:
Fumaric Acid has been used in food and beverage products since 1946.
Fumaric Acid is currently used in wheat and corn tortillas, sour dough and rye breads, refrigerated biscuit doughs, fruit juice and nutraceutical drinks, gelatin desserts, gelling aids, pie fillings and wine.

Food research shows that Fumaric Acid improves quality and reduces costs of many food and beverage products.
Fumaric Acid is also used in animal feed.

*Bakery

*Breads
Fumaric Acid acts as an instant flavoring agent for rye and sourdough breads.
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.

*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 to stabilize the pH of a fruit juice drink, which in turn stabilizes 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 be used to replace every three pounds of Citric, Malic or Tartaric acid. At the 2:3 replacement ratio, Fumaric Acid does not produce significant differences in gel strength or pH.

*Alginate Based Desserts
Fumaric Acid is an economical acidulant that liberates calcium.
Fumaric Acid 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 to maintain the stability of flavor components and markedly decreases inversion of sucrose in the packaged dry mix.
Fumaric Acid may also be possible to use less expensive packaging if other moisture-sensitive ingredients are not being used in the product formulation.
Fumaric Acid also increases gel strength, so food processors may reduce normal gelatin content by about 2%.

*Pie Fillings
In pie fillings, Fumaric Acid can be mixed directly with the starch and sugar ingredients, as it is non-hygroscopic.
Fumaric Acid lowers costs by reducing the quantity of food acid needed in product formulations.
Fumaric Acid also improves smoothness and extends the critical cook times for optimum gelation.

*Egg White Foams
Fumaric Acid can promote maximum volume in both 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 both liquid and dried egg whites.

*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 during the post-weaning period.
The inclusion of Fumaric Acid and the resultant adjustment of the pH value demonstrate improved weight gain, food consumption and feed conversion ratio.

*Industrial Uses
Industrial uses of Fumaric Acid include:
-Unsaturated Polyester

-Alkyd Resins

-Printing Inks

-Paper Sizing

PHYSICAL PROPERTIES:

-Molecular Weight: 116.07

-Exact Mass: 116.01095860

-Monoisotopic Mass: 116.01095860

-Topological Polar Surface Area: 74.6 Å²

-Physical Description: White crystalline powder or granules

-Color: Colorless

-Form: crystal

-Odor: Odorless

-Taste: Fruit acid

-Boiling Point: 522 °C

-Melting Point: 286-302 °C

-Flash Point: 273 °C

-Solubility: 7000 mg/L

-Density: 1.635 g/cu cm

-Vapor Pressure: 1.54X10-4 mm Hg

-LogP: 0.46

-Henry's Law constant: 8.5X10-14 atm-cu m/mol

-Autoignition Temperature: 375 °C

-pH: 3,0-3,2 (0,05 % solution at 25 °C)

-pKa: 3.03

-Collision Cross Section: 133.58 Å²

Fumaric Acid is a chemical compound that is normally found in nature, but scientists have also learned how to make a synthetic version of it to add to all kinds of products including foods, medicines and dyes.
Fumaric Acid is an acid that is naturally occurring in bolete mushrooms and Iceland moss and plays an important role as an intermediate in the citric acid cycle (or the Krebs cycle).
This cycle is very important and helps produce energy from carbs, fats, and proteins in humans.

Fumaric Acid is naturally occurring but how do we get it?
To produce Fumaric Acid there are two main methods that are usually done.

The original method that was done was using bacteria to produce Fumaric Acid.
This was later discontinued and replaced with petrochemical production and sugar fermentation which is how it is produced today.

CHEMICAL PROPERTIES:

-Heavy Atom Count: 8

-Formal Charge: 0

-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

-XLogP3: -0.3

-Hydrogen Bond Donor Count: 2

-Hydrogen Bond Acceptor Count: 4

-Rotatable Bond Count: 2

Fumaric Acid is commonly used as a food additive to add flavor, as a coagulant, as a food preservative, and as an acid in leavening.
Fumaric Acid is one of the strongest organic acids commonly used in food, so it is important to know a bit about it.

Fumaric Acid is used for many reasons one being the ingredients fruity like flavor.
Fumaric Acid is used as an effective anti-microbial agent because it can disrupt microbial activity by interacting with the microbial’s cell wall.

Fumaric Acid is commonly added to different foods or beverages to regulate acidity and pH as it is an acidulant
Fumaric Acid is not just found in plants though, when exposed to natural light, skin naturally makes Fumaric Acid, and that is the reason that it was originally used.

Fumaric Acid was used to treat an autoimmune condition called psoriasis.
This condition is thought to be a genetic disease that is caused by environmental factors and has symptoms of itchy and red skin.

SYNONYMS:

Fumaric Acid
2-Butenedioic acid
trans-Butenedioic acid
Allomaleic acid
Lichenic acid
fumarate
(2E)-but-2-enedioic acid
Boletic acid
Tumaric acid
But-2-enedioic acid
trans-2-Butenedioic acid
trans-1,2-Ethylenedicarboxylic acid
Allomalenic acid
(E)-2-Butenedioic acid
2-Butenedioic acid (E)-
Kyselina fumarova
Butenedioic acid
Butenedioic acid, (E)-
(2E)-2-butenedioic acid
2-Butenedioic acid (2E)-
2-Butenedioic acid, (E)-
2-(E)-Butenedioic acid
1,2-Ethylenedicarboxylic acid, (E)
trans-but-2-enedioic acid
1,2-Ethenedicarboxylic acid, trans-
fum
2-Butenedioic acid (2E)-, homopolymer
Lichenic acid (VAN)
(E)-2-Butenedioate
(E)-Butenedioic acid
Kyselina fumarova
(2E)-but-2-enedioate
Fumarsaeure
Donitic acid
Fumaricum acidum
fumarate, 10
E-2-Butenedioic acid
Fumaric Acid (8CI)
FC 33 (acid)
Futrans-2-Butenedioic Acid
Allomaleate
Boletate
Lichenate
fumeric acid
Modified Gumrosin
trans-Butenedioate
Fumaric Acid,(S)
Maleic Acid (MA)
Fumaric Acid solution
trans-2-Butenedioate
Fumaric Acid (FA)
2-(E)-Butenedioate
(Trans)-butenedioic acid
Fumaric Acid, >=99%
4-02-00-02202 (Beilstein Handbook Reference)
2-butenedioic acid, (2E)-
(2E)-2-Butenedioic acid #
Fumaric Acid (Fragrance Grade)
trans-1,2-Ethylenedicarboxylate
Pharmakon1600-01301022
Fumaric Acid, >=99.0% (T)
2-Butenedioic acid (2E)- (9CI)
BBL022974
Fumaric Acid, >=99%, FCC, FG
NSC760395
s4952
Fumaric Acid, qNMR Standard for DMSO
Fumaric Acid, tested according to USP/NF
Fumaric Acid, puriss.
Fumaric Acid, Vetec(TM)
Fumarate;
2-Butenedioic acid;
Trans-Butenedioic acid
Fumaric Acid, anhydrous