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Fumaric acid is an important kind of organic chemical raw materials as well as the intermediate of fine chemical products.
Meanwhile, Fumaric acid is also an important kind of derivatives of maleic anhydride, being widely used in food, coatings, resins and plasticizers.
In the food industry, fumaric acid, used as souring agent, can be applied to soft drinks, western-style wine, cold drinks, fruit juice concentrate, canned fruit, pickles and ice cream.
CAS: 110-17-8
MF: C4H4O4
MW: 116.07
EINECS: 203-743-0
Synonyms
TRANS-BUTENEDICARBOXYLIC ACID;TRANS-BUTENEDIOIC ACID;TRANS-1,2-ETHYLENEDICARBOXYLIC ACID;TRANS-1,2-ETHYLENTRICARBOXYLIC ACID;RARECHEM AL BO 0142;ACIDUM FUMARICUM;acidefumarique;allomaleicacid
As an acidic substance used as solid beverage gas production agent, Fumaric acid has excellent bubble durability with delicate product organization.
Fumaric acid has been used as a food acidulant since 1946.
As a food additive, Fumaric acid is used as an acidity regulator and can be denoted by the E number E297.
Chemically Fumaric acid is an unsaturated dicarbonic acid and is part of the citric acid cycle.
Fumaric acid is a common food additive included in many processed foods to keep them stable and to add tartness.
Fumaric acid has a more sour flavor than citric acid, another common food additive.
Fumaric acid occurs naturally in fumitory, bolete mushrooms, lichen and Iceland moss.
As an additive, fumaric acid is produced synthetically, mainly from malic acid from apples.
Fumaric acid as an additive is regulated under the Codex Alimentarius General Standard for Food Additives (GSFA), a collection of internationally recognized standards.
The U.S. Food and Drug Administration considers it safe.
A butenedioic acid in which the C2C double bond has E geometry.
Fumaric acid is an intermediate metabolite in the citric acid cycle.
Fumaric acid is a crystalline compound found in certain plants.
Fumaric acid is used in the manufacture of synthetic resins.
Fumaric acid can be converted into the trans isomer by heating at 120°C.
Either of two isomers with the formula HCOOHC:CHCOOH.
Both compounds can be regarded as derivatives of ethene in which a hydrogenatom on each carbon has been replaced by a –COOH group.
The compounds show cis–trans isomerism.
The trans form is fumaric acid (r.d.1.64; sublimes at 165°C) and the cisform is maleic acid (r.d. 1.59; m.p.139–140°C).
Both are colourless crystalline compounds used in making synthetic resins.
The cis form is rather less stable than the trans form and converts to the trans form at 120°C.
Unlike the trans form Fumaric acid can eliminate water on heating to form acyclic anhydride containing a–CO.O.CO– group (maleic anhydride).
Fumaric acid is an intermediate in the Krebs cycle.
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. Used to make paints and plastics, in food processing and preservation, and for other uses.
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 acid's E number is E297.
The salts and esters are known as fumarates.
Fumaric acid 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.
Fumaric acid is a dicarboxylic acid that is used in the treatment of bowel disease.
Fumaric acid is a fumarate, which means it has two carboxylic acid groups and one hydroxyl group.
Fumaric acid reacts with copper chloride to form water vapor, which can be toxic if inhaled.
Fumaric acid also exhibits antimicrobial properties against bacteria and fungi and can be used as a pharmacological agent for the treatment of various diseases.
Fumaric acid's chemical properties are similar to those of sodium salts, which may explain its use in a number of products such as injections or solutions.
Structural analysis reveals that the molecular shape of fumaric acid is linear with three hydrogen atoms on each side of the central carbon atom.
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 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.
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.
Fumaric acid Chemical Properties
Melting point: 298-300 °C (subl.) (lit.)
Boiling point: 137.07°C (rough estimate)
density: 1.62
vapor pressure: 1.7 mm Hg ( 165 °C)
refractive index: 1.5260 (estimate)
FEMA: 2488 | FUMARIC ACID
Fp: 230 °C
storage temp.: Store below +30°C.
solubility: 95% ethanol: soluble0.46g/10 mL, clear, colorless
form: Fine Crystalline Powder
pka: 3.02, 4.38(at 25℃)
color: White
PH: 3.19(1 mM solution);2.57(10 mM solution);2.03(100 mM solution);
Odor: odorless
Odor Type: odorless
biological source: synthetic
explosive limit: 40%
Water Solubility: 0.63 g/100 mL (25 ºC)
Merck: 14,4287
JECFA Number: 618
BRN: 605763
Stability: Stable at room temperature. Decomposes at around 230 C. Incompatible with strong oxidizing agents, bases, reducing agents. Combustible.
Cosmetics Ingredients Functions: BUFFERING
Cosmetic Ingredient Review (CIR): Fumaric acid (110-17-8)
InChI: 1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+
InChIKey: VZCYOOQTPOCHFL-OWOJBTEDSA-N
LogP: -4.02 at 20℃
CAS DataBase Reference: 110-17-8(CAS DataBase Reference)
NIST Chemistry Reference: Fumaric acid(110-17-8)
EPA Substance Registry System: Fumaric acid (110-17-8)
Fumaric acid is naturally presented in Corydalis, mushrooms and fresh beef.
Product precipitated from the water is monoclinic needle-like, prismatic or leaf-like white crystalline or crystalline powder.
Fumaric acid is odorless with a special and strong sour, which is about 1.5 times that of the citric acid.
Fumaric acid has a melting point 287°C, the boiling point of 290°C with subjecting to sublimation at temperature above 200°C.
When being heated to 230°C, it will lose water and become maleic anhydride.
Fumaric acid's co-boiling with water can produce DL-malic acid.
Fumaric acid is soluble in ethanol, slightly soluble in water and ether, but insoluble in chloroform.
The pH value of the 3% aqueous solution is 2.0 to 2.5 with a strong buffering performance, in order to maintain the pH of the aqueous solution at around 3.0.
This product is non-toxic; rat-oral LD50: 8000mg/kg.
Fumaric acid is a colorless to white, odorless crystalline powder.
Fruity-acidic taste.
Fumaric acid occurs as white, odorless or nearly odorless, granules or as a crystalline powder that is virtually nonhygroscopic.
Fumaric acid is odorless with a tart, acidic-sour favor Fumaric acid is used as a replacement of tartaric acid.
White, odorless granules or crystalline powder.
Fumaric acid is soluble in alcohol, slightly soluble in water and in ether, and very slightly soluble in chloroform.
Fumaric acid is used as a replacement for tartaric acid.
Fumaric acid has an odorless, tart, acidic-sour flavor.
Fumaric acid may be synthesized by the action of certain fungi (Rhizopus nigricans) on glucose; by oxidation of furfural with sodium chlorate in the presence of vanadium pentoxide.
Uses
Occurs in many plants.
Essential to vegetable and tissue respiration.
Used as an antioxidant.
Fumaric acid is used in food products as an acidifier with an acid type of taste that blends particularly well with caramellic or sugarsweetened products, baked products, etc.
Fumaric Acid is an acidulant that is a nonhygroscopic, strong acid of poor solubility.
Fumaric acid has a solubility of 0.63 g in 100 ml of distilled water at 25°c.
Fumaric acid dissolves slowly in cold water, but if mixed with dioctyl sodium sulfosuccinate its solubility improves.
The solubility rate also increases with smaller particle size.
a quantity of 0.317 kg of can replace 0.453 kg of citric acid.
Fumaric acid is used in dry mixes such as desserts, pie fillings, and candy.
Fumaric acid is used in dry bever- age mixes because it is storage stable, free flowing, and nonhygro- scopic.
Fumaric acid functions as a synergistic antioxidant with bha and bht in oiland lard-base products.
in gelatin desserts, Fumaric acid improves the flavor stability and increases shelf life and gel strength.
Fumaric acid is used to add fragrance to products and to decrease product pH.
Fumaric acid can also help keep the pH stable.
Fumaric acid is generally used in cleansers.
Fumaric acid is naturally occurring in plants, such as lichen and Iceland moss, and in animals. For example, the skin produces fumaric acid when exposed to light.
Fumaric acid can also F be synthetically manufactured.
1. Fumaric acid is used for the production of unsaturated polyester resin.
This kind of resin is characterized by excellent resistance to chemical corrosion as well as heat resistance; the copolymer of fumaric acid and vinyl acetate is a kind of excellent adhesive.
Fumaric acid's copolymer with styrene copolymer is the raw material for the manufacture of glass fiber.
The plasticizer of the fumaric acid is non-toxic and can be applied to the vinyl acetate latex contact with food.
Fumaric acid is the intermediate of pharmaceutical and optical bleaching agents and other fine chemicals.
Neutralization of fumaric acid with sodium carbonate can generate sodium fumarate ([17013-01-3]), and then replaced with ferrous sulfate to get iron fumarate, being the drug Fersamal used for the treatment of small red blood cell anemic.
Fumaric acid, as a food additive-sourness agent, used in soft drinks, fruit sugar, jelly, ice cream with most of them used in combination with sourness agent, citric acid.
The monosidum salt made from the reaction between fumaric acid and sodium hydroxide can also used as sour seasoning, also used as the intermediate of synthetic resin and mordant.
2. Fumaric acid is included in many dairy-based products.
These include dairy drinks such as chocolate milk, cocoa, eggnog, condensed milk and whey protein beverages.
Fumaric acid also may be added to clotted cream, milk and cream powders and milk and cream analogues (substitutes).
Fumaric acid is added to cheese products, including processed cheese and cheese substitutes.
Dairy-based desserts, such as pudding, flavored yogurt, sherbet and sorbet may include fumaric acid as well.
Dairy fat spreads and blended spreads can include fumaric acid, and so can preserved eggs and egg-based desserts such as custard.
3. Some processed and packaged foods have fumaric acid added to them to help stabilize them and enhance their flavor.
For example, many processed meats, such as bacon and canned meats, have added fumaric acid.
Frozen seafood, smoked meats and the edible casings around sausages might also have fumaric acid added to them.
Fermented, canned, dried and processed fruits and vegetables can contain the food additive as well.
Rice cakes and other precooked rice foods, dried or preserved eggs, mustard, vinegar, cider, wine and other alcoholic beverages are additional examples of foods that might contain fumaric acid.
Pharmaceutical Applications
Fumaric acid is used primarily in liquid pharmaceutical preparations as an acidulant and flavoring agent.
Fumaric acid may be included as the acid part of effervescent tablet formulations, although this use is limited as the compound has an extremely low solubility in water.
Fumaric 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, fumaric acid was used to aid spheronization, favoring the production of fine pellets.
Fumaric acid has also been investigated as an alternative filler to lactose in pellets.
Fumaric acid has been investigated as a lubricant for effervescent tablets, and copolymers of fumaric acid and sebacic acid have been investigated as bioadhesive microspheres.
Fumaric acid has been used in film-coated pellet formulations as an acidifying agent and also to increase drug solubility.
Fumaric 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.
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 acidis 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, Fumaric 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 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.
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.
Production Methods
Commercially, fumaric 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, fumaric acid can be prepared by the oxidation of furfural with sodium chlorate in the presence of vanadium pentoxide.
Synthesis
Fumaric acid is produced based on catalytic isomerisation of maleic acid in aqueous solutions at low pH.
Fumaric acid precipitates from the reaction solution.
Maleic acid is accessible in large volumes as a hydrolysis product of maleic anhydride, produced by catalytic oxidation of benzene or butane.
Biotechnological Production
Currently, fumaric acid is mainly manufactured by chemical synthesis via the precursor maleic acid, which is produced using either benzene or n-butane via catalytic oxidation. However, there are enzymatic and fermentative production routes for fumaric acid.
Prior to the advent of inexpensive petroleumbased chemistry, fumaric acid was produced commercially by fermentation using organisms of the genus Rhizopus with an annual production of 4,000 metric tons.
Product concentrations from 30 to 130 g.L-1 with yields from 0.3 to 1.0 g of fumaric acid per gram of glucose and productivities of 0.46–2.0 g.L-1.h-1 have been reported growing on glucose.
In recent years, new approaches using metabolic engineering have been studied.
For example, fumaric acid concentrations of 28.2 g.L-1 with a productivity of 0.448 g.L-1.h-1 have been reached in fed-batch cultivation of a genetic modified E. coli.
To achieve this result, eight modifications have been implemented.
Fumaric acid could be alternatively synthesized by an enzymatic process starting from maleic acid as in the chemical synthesis.
By whole-cell biocatalysis of the Pseudomonas alcaligenes strain XD-1, a yield of 0.698 g of fumaric acid per gram of maleic acid and a production rate of 6.98 g.L-1.h-1 have been reached.
The process has been optimized.
The formation of the byproduct malic acid was avoided due to an inactivation of fumarase by a heat treatment of the cells beforehand.
Finally, a yield of 0.95 g fumaric acid per gram maleic acid and a production rate of 14.25 g.L-1.h-1 have been observed.
