FUMARIC ACID
FUMARIC ACID
Fumaric acid is an organic compound with the formula HO2CCH=CHCO2H. Fumaric acid is an important kind of organic chemical raw materials as well as the intermediate of fine chemical products. Fumaric acid is odorless with a tart, acidic-sour favor Fumaric acid is used as a replacement of tartaric acid.
A white solid, fumaric acid occurs widely in nature.
It has a fruit-like taste and has been used as a food additive.
Its E number is E297. The salts and esters are known as fumarates.
Fumarate can also refer to the C4H2O2−4 ion (in solution).
The trans isomer possesses a dipole moment.
EC / List no.: 203-743-0
CAS no.: 110-17-8
Mol. formula: C4H4O4
Description
Fumaric acid is an important kind of organic chemical raw materials as well as the intermediate of fine chemical products.
Meanwhile, it 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.
As an acidic substance used as solid beverage gas production agent, it has excellent bubble durability with delicate product organization.
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.
Chemically it 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.
The substance 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.
Chemical Properties
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.
It is odorless with a special and strong sour, which is about 1.5 times that of the citric acid.
It 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. Its co-boiling with water can produce DL-malic acid.
It 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.
Chemical Properties
Fumaric acid is a colorless to white, odorless crystalline powder. Fruity-acidic taste.
Chemical Properties
Fumaric acid occurs as white, odorless or nearly odorless, granules or as a crystalline powder that is virtually nonhygroscopic.
Chemical Properties
White, odorless granules or crystalline powder. It 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. It has an odorless, tart, acidic-sour flavor.
It 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.
Chemical Properties
Fumaric acid is odorless with a tart, acidic-sour favor Fumaric acid is used as a replacement of tartaric acid.
Occurrence
Reported found in several plants, Fumaria offcinalis L , Boletus scaber Boll and lean raw fsh
Uses
fumaric acid is used to add fragrance to products and to decrease product pH.
It can also help keep the pH stable.
It 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. It can also F be synthetically manufactured.
Uses
Fumaric Acid is an acidulant that is a nonhygroscopic, strong acid of poor solubility.
it has a solubility of 0.63 g in 100 ml of distilled water at 25°c.
it 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.
it is used in dry mixes such as desserts, pie fillings, and candy.
it is used in dry bever- age mixes because it is storage stable, free flowing, and nonhygro- scopic.
it functions as a synergistic antioxidant with bha and bht in oiland lard-base products. in gelatin desserts,
it improves the flavor stability and increases shelf life and gel strength.
Uses
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.
Its 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.
This product 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.
The product, 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.
It 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.
Uses
Occurs in many plants. Essential to vegetable and tissue respiration.
Used as an antioxidant.
Definition
ChEBI: A butenedioic acid in which the C2C double bond has E geometry.
It is an intermediate metabolite in the citric acid cycle.
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.
Definition
Either of two isomers. Transbutenedioic acid (fumaric acid) is a crystalline compound found in certain plants.
Cisbutenedioic acid (maleic acid) is used in the manufacture of synthetic resins.
It can be converted into the trans isomer by heating at 120°C.
Definition
butenedioic acid: Either oftwo isomers with the formulaHCOOHC:CHCOOH.
Both compoundscan be regarded as derivativesof ethene in which a hydrogenatom on each carbon has been replacedby a –COOH group.
The compoundsshow 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 crystallinecompounds used in makingsynthetic resins.
The cis form israther less stable than the trans formand converts to the trans form at120°C.
Unlike the trans form it caneliminate water on heating to form acyclic anhydride containing a–CO.O.CO– group (maleic anhydride).
Fumaric acid is an intermediate inthe Krebs cycle.
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.
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.
General Description
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.
Air & Water Reactions
Slightly soluble in water.
Reactivity Profile
Fumaric acid is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them.
They react in this way with all bases, both organic (for example, the amines) and inorganic.
Their reactions with bases, called “neutralizations”, are accompanied by the evolution of substantial amounts of heat.
Neutralization between an acid and a base produces water plus a salt.
Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water.
Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0.
Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt.
Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt.
Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry.
Even “insoluble” carboxylic acids may absorb enough water from the air and dissolve sufficiently in Fumaric acid to corrode or dissolve iron, steel, and aluminum parts and containers.
Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide.
The reaction is slower for dry, solid carboxylic acids.
Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide.
Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat.
Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat.
Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents.
These reactions generate heat.
A wide variety of products is possible.
Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.
Partial carbonization and formation of maleic anhydride occur at 446° F (open vessel).
Health Hazard
Inhalation of dust may cause respiratory irritation. Compound is non-toxic when ingested.
Prolonged contact with eyes or skin may cause irritation.
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.
It 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.
It 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.
It 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.
Safety Profile
Poison by intraperitoneal route. Mildly toxic by ingestion and skin contact.
A skin and eye irritant.
Mutation data reported. Combustible when exposed to heat or flame; can react vigorously with oxidizing materials. When heated to decomposition it emits acrid smoke and irritating fumes.
Safety
Fumaric acid is used in oral pharmaceutical formulations and food products, and is generally regarded as a relatively nontoxic and nonirritant material. However, acute renal failure and other adverse reactions have occurred following the topical and systemic therapeutic use of fumaric acid and fumaric acid derivatives in the treatment of psoriasis or other skin disorders. Other adverse effects of oral therapy have included disturbances of liver function, gastrointestinal effects, and flushing.
The WHO has stated that the establishment of an estimated acceptable daily intake of fumaric acid or its salts was unnecessary since it is a normal constituent of body tissues.
LD50 (mouse, IP): 0.1 g/kg
LD50 (rat, oral): 9.3 g/kg
Potential Exposure
Fumaric acid is used in production of resins, polyesters, plasticizers, and alkyl surface coatings; as a food additive; as an antioxidant in resins; to make dyes.
Carcinogenicity
No evidence of carcinogenicity was found in several chronic studies with rats in which fumaric acid was added to the diet at concentrations up to 1.5%.
As for dermal application, Swiss mice were treated topically twice weekly with a 1% solution in acetone (volume not specified).
Moderate focal hyperplasia was found in the treated group, but no tumors developed.
The inhibitory effect of fumaric acid on hepatocarcinogenesis was examined in male IBR mice fed 0.035% thioacetamide in the diet for 40 weeks and then fed a basal diet for 48 weeks.
The inhibitory effect of 1% fumaric acid in the basal diet on thioacetamide carcinogenesis was so marked that no hepatic carcinomas were found in any of the 15 animals fed fumaric acid in combination with thioacetamide .
Similar inhibitory effects of fumaric acid on forestomach and lung carcinogenesis in mice (that resulted from exposure to potassium naphthyridine-3-carboxylate) have been identified.
storage
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.
The bulk material should be stored in a well-closed container in a cool, dry place.
Purification Methods
Crystallise it from hot M HCl or water and dry it at 100o. [Beilstein 2 IV 2202.]
Incompatibilities
Dust cloud from powder or granular form mixed with air can explode.
Incompatible with oxidi zers (chlorates, nitrates, peroxides, permanganates, perchlo rates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, sulfuric acid, caustics, ammonia, amines, isocyanates, alkylene oxi des; epichlorohydrin. Decomposes above 350℃ forming toxic fumes of maleic anhydride.
Incompatibilities
Fumaric acid undergoes reactions typical of an organic acid.
Waste Disposal
Use a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
All federal, state, and local environmental regula tions must be observed.
Regulatory Status
GRAS listed. Accepted for use as a food additive in Europe.
Included in the FDA Inactive Ingredients Database (oral capsules, suspensions, syrups, extended release and sustained action chewable tablets). Included in the Canadian List of Acceptable Nonmedicinal Ingredients.
Fumaric acid Preparation Products And Raw materials
Raw materials
Ammonium bromide Maleic acid Maleic anhydride Mineral oil Sucrose Maltose Benzene Sodium chlorate wax liquid butene Isomerization catalyst Activated carbon Thiourea
Fumaric acid is an organic compound with the formula HO2CCH=CHCO2H.
A white solid, fumaric acid occurs widely in nature.
It has a fruit-like taste and has been used as a food additive.
Its E number is E297.
The salts and esters are known as fumarates.
Fumarate can also refer to the C4H2O2−4 ion (in solution).
The trans isomer possesses a dipole moment.
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.
Fumaric acid is found in bolete mushrooms, lichen and Iceland moss. Human skin naturally produces fumaric acid when exposed to sunlight.
Fumaric acid is used in the manufacture of medicines, drinks, food, animal feed, cleansing agents, unsaturated polyester, alkyd resins, and printing inks, and is the strongest organic food acid in titratable acidity and sourness.
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.
Its low molecular weight gives fumaric acid more buffering capacity than other food acids at pHs near 3.O.
Because of its strength, less fumaric acid is required when compared to other organic food acids, therefore reducing costs per unit weight.
Fumaric acid is a valuable compound used in foods, beverages, detergents, animal feed, pharmaceuticals and miscellaneous industrial products.
It is produced on a large scale by the petrochemical route but the current tendency is towards implementing “green production” and environmental friendly technologies like biotechnological production of fumaric acid using low-cost raw materials
Chemical names trans-Butenedioic acid, trans-1,2-Ethylene-dicarboxylic acid
C.A.S. number 110-17-8
Chemical formula C4H4O4
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 check
Biosynthesis and occurrence
It is produced in eukaryotic organisms from succinate in complex 2 of the electron transport chain via the enzyme succinate dehydrogenase. It 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.
It 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. It is approved for use as a food additive in the EU,[6] USA[7] and Australia and New Zealand.
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 the making of wheat tortillas as a food preservative and as the acid in leavening.
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, 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.
It 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.
Safety
It is “practically non-toxic” but high doses are probably nephrotoxic after long-term use.
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 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. 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.
It is an intermediate metabolite in the citric acid cycle. It has a role as a food acidity regulator and a fundamental metabolite.
It is a conjugate acid of a fumarate(1-).
fumaric acid
110-17-8
2-Butenedioic acid
trans-Butenedioic acid
Allomaleic acid
Boletic acid
(2E)-but-2-enedioic acid
Lichenic acid
Tumaric acid
trans-2-Butenedioic acid
trans-1,2-Ethylenedicarboxylic acid
Allomalenic acid
(E)-2-Butenedioic acid
But-2-enedioic acid
2-Butenedioic acid (2E)-
2-Butenedioic acid (E)-
Kyselina fumarova
USAF EK-P-583
Butenedioic acid
Butenedioic acid, (E)-
(2E)-2-butenedioic acid
Lichenic acid (VAN)
2-Butenedioic acid, (E)-
Caswell No. 465E
FEMA No. 2488
FEMA Number 2488
2-(E)-Butenedioic acid
Kyselina fumarova [Czech]
NSC-2752
ammonium fumarate
1,2-Ethylenedicarboxylic acid, (E)
CCRIS 1039
HSDB 710
U-1149
trans-but-2-enedioic acid
1,2-Ethenedicarboxylic acid, trans-
EPA Pesticide Chemical Code 051201
Fumaric acid (NF)
Fumaric acid [NF]
UNII-88XHZ13131
AI3-24236
EINECS 203-743-0
MFCD00002700
BRN 0605763
CHEBI:18012
NSC2752
88XHZ13131
6915-18-0
fum
E297
Fumaric acid, 99+%
DSSTox_CID_1518
Futrans-2-Butenedioic Acid
(E)-2-Butenedioate
(E)-Butenedioic acid
DSSTox_RID_76195
DSSTox_GSID_21518
C4H4O4
(2E)-but-2-enedioate
Malezid CM
H2male
Fumarsaeure
Fumaricum acidum
CAS-110-17-8
fumarate, 10
cis-but-2-enedioic acid
E-2-Butenedioic acid
Fumaric acid (8CI)
FC 33 (acid)
Scotchbond Multipurpose Etchant
(2Z)-but-2-enedioate
Allomaleate
Boletate
Lichenate
fumeric acid
Cis-butenedioate
2-Butenedioate
Modified Gumrosin
(z)-butenedioate
trans-Butenedioate
fumaric acid group
NCGC00091192-02
cis-2-Butenedioate
Fumaric Acid,(S)
Maleic Acid (MA)
cis-but-2-enedioate
Fumaric acid solution
trans-2-Butenedioate
Fumaric Acid (FA)
2-(E)-Butenedioate
Fumaric acid, 99%
(2Z)-2-Butenedioate
(Trans)-butenedioic acid
(2Z)-Butene-2-dioate
F0067
Fumaric acid, >=99%
bmse000083
(2Z)-2-Butenedioic acid
EC 203-743-0
Maleic acid [NA2215]
WLN: QV1U1VQ-T
SCHEMBL1177
(2Z)-Butene-2-dioic acid
(E)-but-2-enedioate;hydron
4-02-00-02202 (Beilstein Handbook Reference)
MLS002454406
2-butenedioic acid, (2E)-
(2E)-2-Butenedioic acid #
CHEMBL503160
INS NO.297
Fumaric Acid (Fragrance Grade)
trans-1,2-Ethylenedicarboxylate
DTXSID3021518
BDBM26122
CHEBI:22958
INS-297
HMS2270C12
Pharmakon1600-01301022
Fumaric acid, >=99.0% (T)
MAE
STR02646
ZINC3860193
Tox21_201769
Tox21_302826
2-Butenedioic acid (2E)- (9CI)
BBL022974
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. Used to make paints and plastics, in food processing and preservation, and for other uses.
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. Currently, fumaric acid is mainly produced by petroleum-based chemical synthesis. Limited petroleum resources, rising oil prices, and heightened environmental concern of chemical synthesis have prompted interest in the development of bio-based fumaric acid from renewable resources. Filamentous fungal fermentation with Rhizopus spp. can produce fumaric acid from glucose via a reductive tricarboxylic acid (TCA) pathway and was once used in the industry before the rising of the petrochemical industry. However, conventional fumaric acid fermentation is expensive because of its low product yield and productivity. Filamentous fungal fermentation is also difficult to operate because of its morphology. Methods to control cell growth in the pellet form and to immobilize the mycelia in biofilm have been developed to improve fermentation performance.
In this article, we provide detailed discussions on fumaric acid producing microorganisms (mainly Rhizopus oryzae); the metabolic pathway; key enzymes involved in fumaric acid overproduction; fermentation process conditions including substrates, nutrients, and methods to control cell morphology, fermentation pH, and dissolved oxygen; and separation methods for fumaric acid recovery from the fermentation broth. We conclude that future research aiming at understanding the metabolic pathway and regulatory network associated with fumaric acid biosynthesis should pave the way leading to the development of novel strains for the economical production of fumaric acid from biomass.
Fumaric acid (2-butenedioic acid trans, C4H4O4) derives its name from the fact that the acid is found in plants that belong 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. It is produced as a colorless, crystalline powder with a fruit-like taste (a fruit acid), and it is a weak acid which forms diesters, has low solubility in water, and it undergoes additions across the double bond.
Fumaric and maleic acids were discovered in 1817 by Braconnet and independently by Vauquelin during dry distillation of malic acid.
Fumaric acid is widely used in the food industry as an acidulant because it is nontoxic and is the least expensive of the food-grade acids.
Fumaric acid solubility in water is low (0.6 g per 100 g at 25 °C), and, therefore, in order 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 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, plastics surface coating and paper sizing, and as an intermediate in the preparation of unsaturated polyester and alkyd resins.
Fumaric acid is used by the pharmaceutical industry to produce alexipharmic sodium dimercaptosuccinate and ferrous fumarate, as an optical bleaching agent, in formulations for alternative medicine or as fumaric acid esters monoethylfumarate and dimethylfumarate to treat psoriasis.
Fumaric acid is used in small amounts in the preparation of food, i.e. as an antioxidant.
In the treatment of psoriasis, doses of several hundred mg are common.
Among the side-effects are leucopenia and lymphopenia.
Tolerance for the fetus has not been systematically studied, but the current unpublished experience of the authors on psoriasis treatment with fumaric acid dimethyl fumarate + ethyl hydrogen fumarate have given no indication of embryotoxic or teratogenic effects.
Fumaric acid is an acidulant that possesses a fruitlike flavor.
It occurs naturally, albeit in limited amounts, in such fruits as papayas, pears, and plums.
Fumaric acid has FDA GRAS status in the United States, but its application is not permitted in Europe.
In the United States, fumaric acid is used principally in fruit juices, gelatin desserts, tortillas, and pie fillings.
It is relatively cheap, but it has the great disadvantage of a stronger taste than citric acid and is difficult to dissolve in water.
The solubility of fumaric acid, in fact, 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 solution.
For this reason, solubility often is hastened by heating the solvent, which frequently precludes its use for many food industry applications.
Fumaric Acid
Fumaric acid (E297 or INS297) is a four-carbon dicarboxylic acid and used as acidity regulator in food (Food and Agriculture Organization of the United Nations and World Health Organization, 2017).
Its low cost and non-toxicity are at the basis of its popularity as a food additive since 1946.
Fumaric acid is claimed to be 1.5 times more acid than citric acid.
Microbial inactivation studies have shown that fumaric acid can inactivate food-borne pathogens and extend the shelf life of products such as fresh beef (Tango et al., 2014).
It is often used as a beverage ingredient, but also finds application in bakery products, powdery dessert mixes and confectionary (Santini et al., 2012).
Next to food applications, fumaric acid is used in feed as antibacterial agent and is a well-known chemical that is used in the production of polymers and as intermediate in the production of L-malic and L-aspartic acid.
Fumaric acid is predominantly produced by petroleum-based chemical synthesis, but research focusing on microbial fumaric acid production from starchy materials is in the process of optimizing and commercializing this ‘green’ technique
Fumaric acid is used at a lower level, as two parts of it are just equivalent to three parts of citric acid.
The main drawback in its use is that the solubility of fumaric acid is lower than that of citric acid.
It is not allowed for use in soft drinks directly by UK or EU legislation whereas it is permitted under Annexure IV of directive 95/2/EC (98/72/EC). It also has a tendency to stabilize the suspended matter in both flash-pasteurized and frozen fruit concentrates
Fumaric acid is the most economical of the solid food acids both from the standpoint of cost and the quantities required.
Its applications, however, are limited to some extent by its relatively low solubility in water at different temperatures.
It is one of the most acidic of the solid acids, both in the amount of hydrogen ions it gives to aqueous solutions and in the apparent acidic taste which it imparts.
As little as 60% can be substituted for standard amounts of acidulants in common formulations; acid costs can be reduced as much as 50% when its solubility permits such a substitution.
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 flavour-blending characteristics, it shows an affinity for certain flavouring agents like those in grapes by producing an aftertaste that serves to supplement the overall flavour.
Fumaric acid is used as a food acidulent in beverages and baking powders.
Furthermore, fumaric acid is a pharmaceutically active substance, used to treat psoriasis or multiple sclerosis
The current world market is about 90,000 t y−1.
However, particular interest in fumaric acid – as in all dicarboxylic acids described in this chapter – is derived from its suitability as building block chemical. Use as a bulk chemical in the polymer industry is conceivable. Also its chemical relatedness to aspartic acid, a precursor for aspartam, a widely used sweetener, makes it an interesting product, provided that the production costs are low enough.
Originally, fumaric acid was isolated from plants belonging to the genus Fumaria, from which its name is derived.
It is an old biotech product. In the 1940s fumaric acid was already being produced on a commercial scale (about 4000 t y−1) by fermentation with the filamentous fungus Rhizopus arrhizus (Goldberg et al., 2006). However, with the rapid development of the petrochemistry in the 1960s this process was replaced by chemical synthesis because conventional fumaric acid fermentation is more expensive owing to its low product yield and productivity. Nowadays, microbial production of chemicals from renewable resources is becoming interesting again.
Fumaric acid esters are used to treat a variety of skin disorders, including psoriasis [1], cutaneous sarcoidosis [2], necrobiosis lipoidica diabeticorum [3], and disseminated granuloma annulare [4]. Dimethylfumarate has been used in the treatment of multiple sclerosis, to reduce the frequency of relapse and to slow the onset of disability [5,6]. It activates the nuclear factor (erythroid-derived 2)-like 2 (NrF2) antioxidant response pathway [7]. Flushing and gastrointestinal complaints are common.
History
Fumaric Acid has been used as a food acidulent since 1946.
Fumaric Acid esters were first introduced in the late 1950’s by the German chemist Schweckendiek in the treatment of psoriasis.
A standardized “Fumaric Acid” protocol for psoriasis was developed and used FAEs both orally and topically.
Applications for the chemical compound then expanded to industrial uses.
Fumaric Acid in food
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 gram of citric acid to every 0.91 grams of Fumaric Acid for the same taste.
It 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.
It 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. It is also used in animal feed.
Bakery
Tacos
Fumaric Acid lowers the pH of tortilla dough, thereby improving a mold inhibitor’s effectiveness.
Shelf life of dry tortilla mixes is extended because Fumaric Acid does not absorb moisture during storage and distribution.
In wheat flour tortillas, fumaric acid accelerates the cleavage of disulphide bonds between gluten protein molecules during dough kneading.
The result is more easily machined dough and faster production rates. Added cost savings are realized since leavening acids can be replaced with fumaric acid.
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.
Beverages
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.
Fumaric Acid in combination with Sodium Benzoate was shown to have a bactericidal effect against E.Coli O157:H7 in apple cider at pHs 3.2-3.4.
Fumaric Acid would help juice processors achieve the mandated 5-log pathogen reduction.
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.
Desserts
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 to maintain the stability of flavor components and markedly decreases inversion of sucrose in the packaged dry mix.
It 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
Other names: 2-Butenedioic acid (E)-; trans-Butenedioic Acid; trans-1,2-Ethylenedicarboxylic Acid; Allomaleic acid; Boletic acid; Lichenic acid; Tumaric acid; (E)-2-Butenedioic acid; (E)-HO2CCH=CHCO2H; Butenedioic acid, (E)-; Kyselina fumarova; NSC-2752; U-1149; USAF EK-P-583; 1,2-Ethenedicarboxylic acid, trans-; 1,2-Ethylenedicarboxylic acid, (E); 2-Butenedioic acid (2E)-
Fumaric acid [Wiki]
(2E)-2-Butendisäure [German] [ACD/IUPAC Name]
(2E)-2-Butenedioic acid [ACD/IUPAC Name]
(2E)-But-2-enedioic acid
(E)-1,2-Ethylenedicarboxylic acid
(E)-2-Butenedioic acid
(E)-Butenedioic acid
1,2-Ethenedicarboxylic acid, trans-
110-17-8 [RN]
203-743-0 [EINECS]
2-Butenedioic acid [ACD/IUPAC Name]
2-Butenedioic acid (2E)-
2-Butenedioic acid, (2E)- [ACD/Index Name]
2-Butenedioic acid, (E)-
605763 [Beilstein]
Acide (2E)-2-butènedioïque [French] [ACD/IUPAC Name]
Acidum fumaricum
Butenedioic acid, (E)-
E-2-Butenedioic acid
MFCD00002700 [MDL number]
trans-1,2-ethenedicarboxylic acid
trans-1,2-ethylenedicarboxylic acid
TRANS-2-BUTENEDIOIC ACID
trans-but-2-enedioic acid
trans-Butenedioic acid
(2E)-But-2-enedioate
(E)-2-Butenedioate
(E)-but-2-enedioate
(E)-but-2-enedioic acid
(E)-HO2CCH=CHCO2H
1,2-Ethylenedicarboxylic acid, (E)
2-(E)-Butenedioate
2-(E)-Butenedioic acid
2-Butenedioic acid (E)-
4-02-00-02202 [Beilstein]
605762 [Beilstein]
Allomaleate
Allomaleic acid
Allomalenic acid
Boletate
Boletic acid
cis-Butenedioic acid
Fumaric acid 100 µg/mL in Acetonitrile
Fumaric acid solution
Fumaricum acidum
Fumarsaeure
http:////www.amadischem.com/proen/543768/
http://www.hmdb.ca/metabolites/HMDB0000134
http://www.hmdb.ca/metabolites/HMDB0000176
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:18012
Kyselina fumarova [Czech]
Lichenate
Lichenic acid (VAN)
phenanthrene-9,10-dione
phenanthrene-9,10-dione;9,10-Phenanthraquinone
QV1U1VQ-T [WLN]
STR02646
trans-1,2-Ethylenedicarboxylate
trans-1,2-Ethylentricarboxylic acid
trans-2-Butenedioate
trans-Butenedioate
延胡索酸 [Chinese]
fumaric acid (CHEBI:18012) has role food acidity regulator (CHEBI:64049)
fumaric acid (CHEBI:18012) has role fundamental metabolite (CHEBI:78675)
fumaric acid (CHEBI:18012) is a butenedioic acid (CHEBI:22958)
fumaric acid (CHEBI:18012) is conjugate acid of fumarate(1−) (CHEBI:37154)
(2E)-2-(methoxycarbonylmethyl)but-2-enedioic acid (CHEBI:15661) has functional parent fumaric acid (CHEBI:18012)
3-amino-N-(trans-3-carbamoyloxirane-2-carbonyl)-L-alanine (CHEBI:85509) has functional parent fumaric acid (CHEBI:18012)
N3-fumaramoyl-(S)-2,3-diaminopropanoic acid (CHEBI:85347) has functional parent fumaric acid (CHEBI:18012)
N3-fumaroyl-(S)-2,3-diaminopropanoic acid (CHEBI:85346) has functional parent fumaric acid (CHEBI:18012)
O-fumaryl-L-carnitine (CHEBI:85093) has functional parent fumaric acid (CHEBI:18012)
O-fumarylcarnitine (CHEBI:87264) has functional parent fumaric acid (CHEBI:18012)
dapdiamide (CHEBI:85331) has functional parent fumaric acid (CHEBI:18012)
diethyl fumarate (CHEBI:87388) has functional parent fumaric acid (CHEBI:18012)
dihydroxyfumaric acid (CHEBI:4593) has functional parent fumaric acid (CHEBI:18012)
dimethyl fumarate (CHEBI:76004) has functional parent fumaric acid (CHEBI:18012)
mesaconic acid (CHEBI:16600) has functional parent fumaric acid (CHEBI:18012)
monomethyl fumarate (CHEBI:167450) has functional parent fumaric acid (CHEBI:18012)
fumarate(1−) (CHEBI:37154) is conjugate base of fumaric acid (CHEBI:18012)
(E)-3-carboxyprop-2-enoyl group (CHEBI:24126) is substituent group from fumaric acid (CHEBI:18012)
fumaroyl group (CHEBI:24125) is substituent group from fumaric acid (CHEBI:18012)
IUPAC Name : (2E)-but-2-enedioic acid
Synonyms
(2E)-2-butenedioic acid
(E)-2-butenedioic acid
E297
Fumaric acid
FUMARIC ACID
Fumarsäure Deutsch
trans-1,2-ethylenedicarboxylic acid
trans-but-2-enedioic acid
trans-Butenedioic acid
FUMARIC ACID
This is obtained from the hydration of Maleic Anhydride or from isomerization of Maleic Acid solutions resulting from the process (washing) of Phthalic Anhydride.
Its application areas are Unsaturated Polyester Resins, the acidifying of animal feed and plasticized products.
Application areas
Animal food / Building and Construction / Chemical Industry / Food and Beverage / Home and Domestic Applications / Industrial sector / Medical and Pharmaceutical / Paper Industr
acid fumaric (ro)
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)
kwas fumarowy (pl)
kwas trans-etyleno-1,2-dikarboksylowy (pl)
kyselina fumarová (sk)
ácido fumárico (es)
ácido fumárico (pt)
φουμαρικό οξύ (el)
фумарова киселина (bg)
CAS names
2-Butenedioic acid (2E)-
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
Fumaric acid
trans-1,2-Ethylenedicarboxylic acid
TRANS-BUTENEDICARBOXYLIC ACID
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
acidefumarique
Allomaleic acid
allomaleicacid
Boletic acid
boleticacid
trans-Ethylene-1,2-dicarboxylicacid
Tumaric acid
U-1149
USAF ek-p-583
usafek-p-583
Butenedioic acid
FRUCTUSLYCII.P.E
(E)-but-2-enedioic acid
FUMARIC ACID extrapure AR
Fumaric acid, 94%, contains ca. 5% starch
Fumarsure
Fumaric acid,Acidum fumaricum
Fumaric acid, extra pure
Fumaric Acid (200 mg)
Fumaric Acid (200 mg)H0E3281.00mg/mg(ai)
Fumaric Acid (Food and Technical)
FuMaric acid, 99+% 1KG
TMEDA trans-2-Butenedioic Acid
(e)-butenedioicaci
(E)-HO2CCH=CHCO2H
1,2-Ethenedicarboxylic acid, trans-
1,2-Ethylenedicarboxylic acid, (E)
1,2-ethylenedicarboxylicacid
1,2-ethylenedicarboxylicacid,(e)
2-Butenedioic acid (E)-
2-Butenedioicacid(E)-
(2E)-2-Butenedioic acid
(e)-2-butenedioicaci
Tenofovir Disoproxil Fumarate impurity R
food grade high quality fumaric acid cas 110-17-8
JACS-110-17-8
FUMARSAEURE
FUMARIC ACID FOR SYNTHESIS
FUMARIC ACID FOR SYNTHESIS 2,5 KG
Fumaric acid, 99.5%
FUMARIC ACID+A10746
2-Butenedioic acid (2E)-
FUMARICACID,FCC
FUMARICACID,NF
2-BUTENEDIOIC ACID
1-(E)-butenedioic acid
E-butenedioic acid
FUMARICACIDANDITSCOMMONSALTS
FUMARIC ACID (FOOD GRADE)
FUMARIC ACID TECH GRADE
Fumaric acid can be produced bysubjecting an aqueous solution of maleic acid to a catalytic isomerization process.
A suitable catalyst is hydrochloric acid andv the isomerization can be effected by the heating of an aqueous solution of maleic acid and hydrochloric acid catalyst in the proper proportions.
As the isomerization progresses and fumaric acid is formed, the fumaric acid crystallizes out of the reaction mixture due to its low solubility in the reaction mixture, and the fumaric acid crystals are subsequently separated, for example, by filtration or centrifuging.
Fumaric acid is normally a crystalline material having a very low solubility in water and acidic aqueous medium.
However, an alkali metal acid fumarate such sodium acid fumarate or potassium acid fumarate is readily soluble in water or an aqueous medium having a pH in the range of 2.8 to 5
Fumaric acid is an organic acid that serves a variety of functional purposes, including enhancing taste, managing pH, reducing hygroscopicity, improving shelf stability, and more.
Fumaric acid is a functional ingredient that is applicable across food, beverage, animal nutrition, industrial, pharmaceutical, and personal care markets.
Fumaric acid has been used in food and beverage products for almost a century and is most commonly relied on to improve quality and reduce costs of many food, beverage, and animal feed products.
An effective tool for balancing the pH in food and beverages, fumaric acid controls the impact and intensity of sourness and flavor as well as having an anti-microbial and bactericidal effect. Fumaric acid is completely non-hygroscopic, keeping powdered mixes from caking and hardening from moisture. It is also stronger than other acids, enabling the use of less product to achieve the same results–thereby improving economies by lowering ingredient cost.
Chocolate cakes and gel-desserts or 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
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.
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.
Applications
Jellies, Jams, & Desserts.
Providing better texture and gelling properties while increasing flavor stability and lengthening shelf life, fumaric acid improves jellies, jams, preserves, and desserts.
Additionally, in egg white foams and applications that use egg white foams, fumaric acid increases volume and replaces cream of tartar, delivering cost efficiencies.
The effervescence of both personal care and cosmetic products comes from powdered fumaric acid and carbon dioxide ingredients combined and tableted.
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.
Fumaric acid is used in the production of many industrial materials, including unsaturated polyester, alkyd resins, printing inks, and paper sizing.
Fumaric acid (trans-2-butenedioic acid) is a multifunctional chemical with a diverse set of end uses, including unsaturated polyester resins, food and beverages, L-aspartic acid, rosin paper sizes, alkyd resins, and animal feed.
Unsaturated polyester resin (UPR) is the largest end use for fumaric acid in 2019.
The food and beverages segment was the second-largest end use for fumaric acid.
In food and beverage applications, fumaric acid serves primarily as an acidulant; it is used to adjust pH, enhance flavor, and extend shelf life by controlling the growth of microorganisms. Expansion of this segment will be driven largely by demand increases in China and Other Asia.
In other regions, food and beverage applications are comparatively mature, and consumption growth will be steady but moderate.
L-Aspartic acid production, the third-largest end use for fumaric acid, is expected to see the fastest growth during the forecast period.
L-Aspartic acid and phenylalanine are the key building blocks for aspartame, a zero-calorie high-intensity sweetener that is widely used in diet soft drinks and other low-calorie foods.
China is the largest producer and consumer of L-aspartic acid.
What is Fumaric Acid?
Fumaric acid is an organic acid found widely in nature.
It is a colorless, odorless, crystalline powder with tart-fruity taste.
The least expensive food acidulant, it’s a clean label food additive used in beverages, baked goods, confections and dessert mixes as a:
Long-lasting and persistent sourness
Substitute for tartaric and citric acids
Acidity regulator
Antibacterial agent and shelf-life extender
Chemical structure
Origin
Natural sources of fumaric acid include bolete mushrooms, lichen, and Iceland moss.
It’s also found in papayas, pears and plums, but in very limited amounts.
It was first isolated from the plant Fumaria officinalis, which is where it derives its name.
Today, this acid is produced via chemical or enzymatic treatment of starchy materials.
Its use as an acidulant dates back to 1946.
Function
In foods and baked goods, it serves many functions:
Acidity control (measured by pH or more accurately by TTA)
Highly effective acidulant
Substitute for other acids such as citric, lactic, and tartaric1,2
Strong buffering capacity around pH 3.04
Antimicrobial / preservative activity
Chemical leavening – highly effective, with a Neutralization Value of 145
Dough machinability improver
Flavor/ taste sourness enhancer
Foam promoter in egg-white foams and a stabilizer of over-beaten egg whites
Commercial production
Fumaric acid is primarily produced using isomerization or biochemical routes.
Isomerization: this method is based on the conversion of maleic anhydride to maleic acid and the cis–trans isomerization of maleic acid to the final product.
Biochemical: relies on bioconversion of substrates such as corn starch, corn straw, cassava bagasse or potato flour using maleate isomerase produced by Pseudomonas and Arthrobacter species.
Application
If you’re adding fumaric acid bakery products, here are a few things to keep in mind:
In bread, this acid is used mainly as an effective preservative and mold inhibitor.
In artisan and sourdough breads, it imparts pleasant sour notes. It can also help improve dough rheology and enhance the formation of a porous crumb.
Mold growth is a major quality issue with tortillas.
The addition of this ingredient is an essential mold growth inhibitor and shelf life extender, a result of its unique solubility profile.
It can also act as a leavening acid. It is also used as an effective preservative in refrigerated biscuits and other baked goods.
It is added to English muffins to improve dough machinability and baked muffin porosity.
In pie fillings, it d helps promote a smooth and optimal gelation due to extended critical cook time.
In stove-top pudding mixes, fumaric acid is used as a coagulant.
One drawback of fumaric acid is its low solubility which can be improved by dissolving in hot water.
Fumaric acid also finds application in unsaturated polyester resins and alkyd resins to maintain the molecular chain.
The demand for these products is expected to grow in the coming years owing to its application in the construction as well as automotive production.
Thus, an increase in construction activities all across the globe, and expansion of automotive production will foster the market demand.
Food and Beverage Sector to Dominate the Market
Food processing is one of the major applications of fumaric acid.
Fumaric acid is a common food additive that is used in many processed foods to keep the food stable and to add tartness.
Fumaric acid has a sourer flavor than its counterpart citric acid (another common food additive).
Fumaric acid naturally occurs in mushrooms, lichen, fumitory, Iceland moss, and bolete.
However for use as a food additive fumaric acid is produced synthetically, commonly from malic acid from apples.
When fumaric acid is used as a food additive, the hydrophobic nature of the product results in long-lasting sourness along with some flavor impact.
Fumaric acid also decreases the pH value with minimum additional sourness.
The low molecular weight of fumaric acid gives it more buffering capacity than other food acids.
Fumaric acid usage also reduces costs as less quantity is required to be added because of its strength.
Many processes and packaged food have fumaric acid for stabilization along with enchasing their flavor.
For instance, fumaric acid is added to many processed meats such as canned meat and bacon.
The fumaric acid is also added to the frozen food especially seafood, smoked meats and the edible casings around sausages might also have fumaric acid added to them.
This food additive is also used in the Fermented, canned, dried and processed fruits and vegetables.
Rice cakes and some other precooked rice foods, dried or preserved eggs, mustard, vinegar, cider, wine along with other alcoholic beverages are additional examples of foods that might contain fumaric acid.
Fumaric acid is also added to certain dairy products to stabilize them and also to add tardiness.
Diary foods such as chocolate milk and eggnog contains this acid to help enhance the flavor.
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.
The growing food processing industry especially in developing world is driving the demand for the fumaric acid.
The demand for canned fish and seafood has witnessed a steady growth over the past few years owing to the consumer awareness regarding the nutritional benefits of fish and seafood coupled with the convenience in consumption it provides and the long shelf life it possesses.
Asia-Pacific region is the fastest-growing region in the global market of canned foods, especially canned meat, fish/seafood, and fruits.
According to the Food and Agriculture Organization of the United Nations, Asia-Pacific is currently the largest exporter as well as the largest importer of seafood in the world.
Countries, such as Japan, Korea, and China import canned crab meat in high quantities.
According to the recent estimates of FAO, China and Korea were the largest importers of crab meat, after the United States.
Food processing sector in India has been primary export oriented, however in the local market is also growing in last decade owing to urbanization and consumer preferences.
India exported processed food valued at around INR 31,111 croreswhich mainly consists of processed fruits, vegetables and meats including seafood along with sizeable chunk of alcoholic beverages.
Despite trade tension, the processed food demand in Unites States has shown growth in 2019 especially processed meat products.
In Europe we are observing a trend towards more fresh food than processed food.
Demand for food processing demand in the GCC is expected to grow at a CAGR of 3.3% from an estimated 51.5 million MT in 2018 to 60.7 million MT in 2023.
Primarily, increase in population, growing tourism, a high per capita income and a recovering economy are likely to drive growth of the food sector in the region.
Overall the demand growth for fumaric acid is expected to be moderate to high during the forecast period from food processing application.
Fumaric acid is also used in the production of the L-Aspartic acid.
L-Aspartic acid and phenylalanine are the main building blocks for aspartame, a zero-calorie high-intensity sweetener that is widely used in diet soft drinks and other low-calorie foods.
Asia-Pacific is the largest producer and consumer of L-aspartic acid globally.
In the chemical industry, the demand for fumaric acid is majorly attributed to the increasing demand for unsaturated polyester resins and alkyd resins that are predominantly used in the production of paints and coatings and adhesives and sealants.
The growing construction and automotive industries are expected to drive the consumption of various materials such as paints and coatings, adhesives and sealants, and rosin paper, which in turn will increase the production of unsaturated polyester resins and alkyd resins, thereby boosting the demand for fumaric in the country through the forecast period.
Apart from this, fumaric acid is also used as a building block for many intermediates including, fumarates, L-Aspartic acid and phenylalanine, among others; thereby increasing the consumption of fumaric acid.
Application / Segment
Foods
Powder drinks
Chemistry
Fumaric acid
Applications
Used as acidifier, pH regulator, effervescent and masking in powder drinks.
Benefits and Features
The CWS (cold water soluble) presentation is best suited for use in powdered drinks as its fine particle size ensures good mixing of the ingredients, and ensures a quick solubilization of the mixture for the final preparation.
Prevents compaction of ingredients in the case of dry preparations, due to its low hygroscopicity that maintains unaltered the consistency of the mixture after being opened.
It can be used as effervescent when accompanied by carbonates in the dry mixture.
In diet drinks masks metal remnants left over by some sweeteners.
In fruit juices, fumaric acid is used in combination with citric acid to reduce the proportion of preservatives like sorbates, propionates and benzoates due to the synergy shown by Fumaric Acid with such additives.
It is also used as a pH regulator due to its acid strength, allowing to reduce the total acid content in the juice.
Is used to preserve fruit concentrates from fungi and other microorganisms.
Applications
Used as acidifier, pH regulator, effervescent and masking in powder drinks.
Benefits and Features
In fruit juices, fumaric acid is used in combination with citric acid to reduce the proportion of preservatives like sorbates, propionates and benzoates due to the synergy shown by Fumaric Acid with such additives.
It is also used as a pH regulator due to its acid strength, allowing to reduce the total acid content in the juice.
Is used to preserve fruit concentrates from fungi and other microorganisms.
Applications
Employed to improve texture, leavening agent, pH regulator and preservative in tortillas and breads.
Benefits and Features
In tortilla and bread either corn or wheat flour acts as a texture improver due to its unique reducing properties, which by breaking the disulfide bridges of proteins, makes a softer dough, which improves texture and reduces the energy consumed in the kneading.
Also acts as blowing agent for cakes, cookies, pancakes, waffles, donuts and cookies.
It may be added to chilled doughs to generate lighter products and prevent crystallization of phosphates that are included in some baking powders.
The fumaric acid instantly provides citrus flavoring in sour or rye breads, eliminating the need for fermentation for flavor development.
For this can be added to the dry ingredient mix.
Confers stability to the foam prepared with egg albumin.
Increases the lifetime as it is synergistic with most products used in bakery as preservatives.
Applications
Used as acidifier, pH regulator, effervescent and masking, in jellies.
Benefits and Features
In jellies, jams, preserves and fruit concentrates, regulates the pH to ensure the effectiveness of gelling agents.
In algins based products stiffens the gel and helps to form the molecular sieve acting as releasing calcium.
Increase the service life of packaged products with its preservative properties and low moisture absorption.
Fumaric acid is an organic acid widely found in nature.
In humans and other mammals, Fumaric acid is a key intermediate in the tricarboxylic acid cycle for organic acid biosynthesis (the KREBS cycle). Fumaric acid is also an essential ingredient in plant life.
Use: Fumaric Acid has many uses that include resins, coatings, oils, foods and beverages, inks, and pharmaceuticals.
boletic acid
(2E)- but-2-enedioic acid
(E)- but-2-enedioic acid
trans- but-2-enedioic acid
(E)- butene dioic acid
(2E)-2- butenedioic acid
(E)- butenedioic acid
(E)-2- butenedioic acid
trans-2- butenedioic acid
2- butenedioic acid (2E)-
2- butenedioic acid, (2E)-
butenedioic acid, (E)-
2- butenedioic acid, (E)-
trans-1,2- ethenedicarboxylic acid
1,2- ethenedicarboxylic acid, trans-
(E)-1,2- ethylene dicarboxylic acid
alpha,beta- ethylene-1,2-dicarboxylic acid
(E)-1,2- ethylenedicarboxylic acid
trans-1,2- ethylenedicarboxylic acid
fumaric acid FCC
fumaric acid FCC powder cold water soluble CWS 31502
fumaric acid natural
fumaric acid NF FCC granular FF
fumaricacid
fumarsaeure
lichenic acid
allo maleic acid
allo- maleic acid
allo- malenic acid
(E)- tumaric acid