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Fumaric Acid Anhydrous or trans-butenedioic acid is an organic compound with the formula HO2CCH=CHCO2H.
A white solid, Fumaric Acid Anhydrous occurs widely in nature.
Fumaric Acid Anhydrous has a fruit-like taste and has been used as a food additive.
CAS: 110-17-8
MF: C4H4O4
MW: 116.07
EINECS: 203-743-0
Synonyms
TRANS-2-BUTEN-1,4-DIOIC ACID;TRANS-2-BUTENEDIOIC ACID;TRANS-BUTENEDICARBOXYLIC ACID;TRANS-BUTENEDIOIC ACID;TRANS-1,2-ETHYLENEDICARBOXYLIC ACID;TRANS-1,2-ETHYLENTRICARBOXYLIC ACID;RARECHEM AL BO 0142;ACIDUM FUMARICUM
Fumaric Acid Anhydrous's E number is E297.
The salts and esters are known as fumarates.
Fumaric Acid Anhydrous can also refer to the C4H2O2−4 ion (in solution).
Fumaric Acid Anhydrous is the trans isomer of butenedioic acid, while maleic acid is the cis isomer.
Fumaric Acid Anhydrous is an important kind of organic chemical raw materials as well as the intermediate of fine chemical products.
Meanwhile, Fumaric Acid Anhydrous 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 Anhydrous, used as souring agent, can be applied to soft drinks, western-style wine, cold drinks, fruit juice concentrate, canned fruit, pickles and ice cream.
As an acidic substance used as solid beverage gas production agent, Fumaric Acid Anhydrous has excellent bubble durability with delicate product organization.
Fumaric Acid Anhydrous has been used as a food acidulant since 1946.
As a food additive, Fumaric Acid Anhydrous is used as an acidity regulator and can be denoted by the E number E297.
Chemically Fumaric Acid Anhydrous is an unsaturated dicarbonic acid and is part of the citric acid cycle.
Fumaric Acid Anhydrous is a common food additive included in many processed foods to keep them stable and to add tartness.
Fumaric Acid Anhydrous 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 Anhydrous is produced synthetically, mainly from malic acid from apples.
Fumaric Acid Anhydrous 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 Anhydrous is an intermediate metabolite in the citric acid cycle.
Butenedioic Acid: 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 at120°C.
Unlike the trans form Fumaric Acid Anhydrous 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.
Fumaric Acid Anhydrous used as a seasoning, because E297 is the organic acid sourest taste.
Fumaric Acid Anhydrous three parts are as sour as the five parts of citric acid.
Fumaric Acid Anhydrous but also as an antioxidant, mordant (a substance that helps the dye adhere to fabric), and as a buffer (to help maintain a particular acidity or alkalinity).
Fumaric Acid Anhydrous is used to lower the pH (acid to make more things, which taste more sour).
This helps to a certain degree of anti-microbial agents, such as better work.
Fumaric Acid Anhydrous itself to kill bacteria.
Fumaric Acid Anhydrous break the bread dough the elastic protein gluten of the sulfur-sulfur bond.
This makes the dough more machinable.
Fumaric Acid Anhydrous is in the use of rye bread and yeast, making them more acid.
Fumaric Acid Anhydrous combined with leavening agent (carbon dioxide gas produced carbin to make bread rise) to create slow.
Because Fumaric Acid Anhydrous is only dissolved in warm water, leavening action postponed to start baking bread.
Fumaric Acid Anhydrous also used to produce unsaturated polyester resins, fumaric acid fumaric acid formula HO2CCH = CHCO2H compounds.
This white crystalline compound of two isomers of the unsaturated dicarboxylic acid, maleic acid, the other one, which carboxylic acid groups of the CIS [= (Z)].
Fumaric Acid with fruit flavor.
Fumaric Acid Anhydrous 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.
InChIKey: VZCYOOQTPOCHFL-OWOJBTEDSA-N
LogP: -4.02 at 20℃
CAS DataBase Reference: 110-17-8(CAS DataBase Reference)
NIST Chemistry Reference: Fumaric Acid Anhydrous (110-17-8)
EPA Substance Registry System: Fumaric Acid Anhydrous (110-17-8)
Fumaric Acid Anhydrous 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 Anhydrous is odorless with a special and strong sour, which is about 1.5 times that of the citric acid.
Fumaric Acid Anhydrous 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, Fumaric Acid Anhydrous will lose water and become maleic anhydride.
Fumaric Acid Anhydrous's co-boiling with water can produce DL-malic acid.
Fumaric Acid Anhydrous 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.
Fumaric Acid Anhydrous is non-toxic; rat-oral LD50: 8000mg/kg.
Fumaric Acid Anhydrous is a colorless to white, odorless crystalline powder.
Fruity-acidic taste.
Fumaric Acid Anhydrous occurs as white, odorless or nearly odorless, granules or as a crystalline powder that is virtually nonhygroscopic.
Fumaric Acid Anhydrous 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 Anhydrous is soluble in alcohol, slightly soluble in water and in ether, and very slightly soluble in chloroform.
Fumaric Acid Anhydrous is used as a replacement for tartaric acid.
Fumaric Acid Anhydrous has an odorless, tart, acidic-sour flavor.
Fumaric Acid Anhydrous 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.
Biosynthesis and occurrence
Fumaric Acid Anhydrous is produced in eukaryotic organisms from succinate in complex 2 of the electron transport chain via the enzyme succinate dehydrogenase.
Fumaric Acid Anhydrous is found in fumitory (Fumaria officinalis), bolete mushrooms (specifically Boletus fomentarius var. pseudo-igniarius), lichen, and Iceland moss.
Fumaric Acid Anhydrous 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 Anhydrous is formed by the oxidation of succinate by the enzyme succinate dehydrogenase.
Fumaric Acid Anhydrous is then converted by the enzyme fumarase to malate.
Human skin naturally produces fumaric acid when exposed to sunlight.
Fumaric Acid Anhydrous is also a product of the urea cycle.
Uses
Occurs in many plants.
Essential to vegetable and tissue respiration.
Used as an antioxidant.
Fumaric Acid Anhydrous 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 Anhydrous has a solubility of 0.63 g in 100 ml of distilled water at 25°c.
Fumaric Acid Anhydrous 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 Anhydrous is used in dry mixes such as desserts, pie fillings, and candy.
Fumaric Acid Anhydrous is used in dry bever- age mixes because it is storage stable, free flowing, and nonhygro- scopic.
Fumaric Acid Anhydrous functions as a synergistic antioxidant with bha and bht in oiland lard-base products.
In gelatin desserts, Fumaric Acid Anhydrous improves the flavor stability and increases shelf life and gel strength.
1. Fumaric Acid Anhydrous 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 Anhydrous's copolymer with styrene copolymer is the raw material for the manufacture of glass fiber.
The plasticizer of the Fumaric Acid Anhydrous is non-toxic and can be applied to the vinyl acetate latex contact with food.
Fumaric Acid Anhydrous 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 Anhydrous, 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 Anhydrous and sodium hydroxide can also used as sour seasoning, also used as the intermediate of synthetic resin and mordant.
2. Fumaric Acid Anhydrous 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 Anhydrous also may be added to clotted cream, milk and cream powders and milk and cream analogues (substitutes).
Fumaric Acid Anhydrous 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 Anhydrous as well.
Dairy fat spreads and blended spreads can include Fumaric Acid Anhydrous, and so can preserved eggs and egg-based desserts such as custard.
3. Some processed and packaged foods have Fumaric Acid Anhydrous 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 Anhydrous.
Frozen seafood, smoked meats and the edible casings around sausages might also have Fumaric Acid Anhydrous 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 Anhydrous.
Fumaric Acid Anhydrous is used to add fragrance to products and to decrease product pH. It can also help keep the pH stable.
Fumaric Acid Anhydrous is generally used in cleansers.
Fumaric Acid Anhydrous is naturally occurring in plants, such as lichen and Iceland moss, and in animals.
For example, the skin produces Fumaric Acid Anhydrous when exposed to light.
Fumaric Acid Anhydrous can also F be synthetically manufactured.
Food
Fumaric Acid Anhydrous has been used as a food acidulant since 1946.
Fumaric Acid Anhydrous is approved for use as a food additive in the EU, USA and Australia and New Zealand.
As a food additive, Fumaric Acid Anhydrous is used as an acidity regulator and can be denoted by the E number E297.
Fumaric Acid Anhydrous is generally used in beverages and baking powders for which requirements are placed on purity.
Fumaric Acid Anhydrous is used in the making of wheat tortillas as a food preservative and as the acid in leavening.
Fumaric Acid Anhydrous 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 Anhydrous is also used as a coagulant in stove-top pudding mixes.
Medicine
Fumaric Acid Anhydrous 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 Anhydrous activates the Nrf2 antioxidant response pathway, the primary cellular defense against the cytotoxic effects of oxidative stress.
Pharmaceutical Applications
Fumaric Acid Anhydrous is used primarily in liquid pharmaceutical preparations as an acidulant and flavoring agent.
Fumaric Acid Anhydrous 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 Anhydrous 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 Anhydrous has also been investigated as an alternative filler to lactose in pellets.
Fumaric Acid Anhydrous has been investigated as a lubricant for effervescent tablets, and copolymers of Fumaric Acid Anhydrous and sebacic acid have been investigated as bioadhesive microspheres.
Fumaric Acid Anhydrous has been used in film-coated pellet formulations as an acidifying agent and also to increase drug solubility.
Fumaric Acid Anhydrous 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.
Preparation
By the action of certain fungi (Rhizopus nigricans) on glucose; by oxidation of furfural with sodium chlorate in the pres- ence of vanadium pentoxide.
Production Methods
Commercially, Fumaric Acid Anhydrous 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 Anhydrous can be prepared by the oxidation of furfural with sodium chlorate in the presence of vanadium pentoxide.
Synthesis
Fumaric Acid Anhydrous is produced based on catalytic isomerisation of maleic acid in aqueous solutions at low pH.
Fumaric Acid Anhydrous 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.
Historic and laboratory routes
Fumaric Acid Anhydrous 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.
