| Identification | More | [Name]
Fumaric acid | [CAS]
110-17-8 | [Synonyms]
2-BUTENEDIOIC ACID
ACIDUM FUMARICUM
(e)-1,2-ethenedicarboxylic acid
(E)-2-Butenedioic acid
FA
FEMA 2488
FUMARIC ACID
LICHENIC ACID
RARECHEM AL BO 0142
TRANS-1,2-ETHYLENEDICARBOXYLIC ACID
TRANS-1,2-ETHYLENTRICARBOXYLIC ACID
TRANS-2-BUTEN-1,4-DIOIC ACID
TRANS-2-BUTENEDIOIC ACID
TRANS-BUTENEDICARBOXYLIC ACID
TRANS-BUTENEDIOIC ACID
(2E)-2-Butenedioic acid
(e)-2-butenedioicaci
(e)-butenedioicaci
(E)-HO2CCH=CHCO2H
1,2-Ethenedicarboxylic acid, trans- | [EINECS(EC#)]
203-743-0 | [Molecular Formula]
C4H4O4 | [MDL Number]
MFCD00002700 | [Molecular Weight]
116.07 | [MOL File]
110-17-8.mol |
| Chemical Properties | Back Directory | [Appearance]
Fumaric acid is a colorless to white, odorless
crystalline powder. Fruity-acidic taste. | [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)
| [FEMA ]
2488 | [refractive index ]
1.5260 (estimate) | [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 | [Odor]
odorless | [PH]
2.1 (4.9g/l, H2O, 20℃) | [Stability:]
Stable at room temperature. Decomposes at around 230 C. Incompatible with strong oxidizing agents, bases, reducing agents. Combustible. | [explosive limit]
40% | [Odor Type]
odorless | [Water Solubility ]
0.63 g/100 mL (25 ºC) | [JECFA Number]
618 | [Merck ]
14,4287 | [BRN ]
605763 | [InChIKey]
VZCYOOQTPOCHFL-OWOJBTEDSA-N | [LogP]
-4.02 at 20℃ | [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. | [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) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36:Irritating to the eyes. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [RIDADR ]
UN 9126 | [WGK Germany ]
1
| [RTECS ]
LS9625000
| [Autoignition Temperature]
375 °C | [TSCA ]
Yes | [HS Code ]
29171900 | [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. | [Hazardous Substances Data]
110-17-8(Hazardous Substances Data) | [Toxicity]
LD50 orally in Rabbit: 9300 mg/kg LD50 dermal Rabbit 20000 mg/kg |
| Hazard Information | Back Directory | [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. | [Reactivity Profile]
FUMARIC ACID(110-17-8) 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(110-17-8) 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). | [Air & Water Reactions]
Slightly soluble in water. | [Health Hazard]
Inhalation of dust may cause respiratory irritation. Compound is non-toxic when ingested. Prolonged contact with eyes or skin may cause irritation. | [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. | [First aid]
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
15 minutes, occasionally lifting upper and lower lids. Seek
medical attention immediately. If this chemical contacts the
skin, remove contaminated clothing and wash immediately
with soap and water. Seek medical attention immediately.
If this chemical has been inhaled, remove from exposure,
begin rescue breathing (using universal precautions, includ ing resuscitation mask) if breathing has stopped and CPR if
heart action has stopped. Transfer promptly to a medical
facility. When this chemical has been swallowed, get medi cal attention. Give large quantities of water and induce
vomiting. Do not make an unconscious person vomit. | [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. | [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. | [Occurrence]
Reported found in several plants, Fumaria offcinalis L , Boletus scaber Boll and lean raw fsh | [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. | [Definition]
ChEBI: A butenedioic acid in which the C2C double bond has E geometry. It is an intermediate metabolite in the citric acid cycle. | [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. | [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 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. | [Flammability and Explosibility]
Nonflammable | [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]
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 | [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.] | [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. |
| Questions and Answers (Q&A) | Back Directory | [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. | [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. | [Fumaric Acid Foods]
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.
Dairy Products
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.
Processed Foods
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. | [Chemical reaction]
The molecular structure of fumaric acid contains conjugated maleic acid group with both ends of ethylene double bonds being connected with a carbonyl group. Its chemical properties are very lively. It can undergo Diels-Alder reaction; polymerization (self-polymerization and copolymerization); acylation, amidation, halogenation, hydrogenation, hydration or dehydration, alkylation, free radical reaction and nucleophilic reaction; isomerization: when being heated to 250~300 ° C, it can be converted into maleic acid; esterification reaction; acyl halogenation reaction, can only generate diacid chloride, not able to produce acyl chloride; oxidation and reduction reaction; oxidation with potassium permanganate can generate racemic tartaric acid; decomposition, decarboxylation reaction and sulfonation reaction.
This information was provided by Chemicalbook Editor (2015-09-02). | [Side Effects]
Fumaric acid is related to malic acid, and, like malic acid , it is involved in the production of energy (in the form of adenosine triphosphate [ATP]) from food.
Fumaric acid Side Effects: Kidney disorders have been reported in people taking fumaric acid esters, possibly due to taking large amounts too quickly.9 , 10 Most studies have reported gastrointestinal upset and skin flushing as common side effects; some have also found decreased white blood cell counts with prolonged use. | [Uses]
1. It can be used as mordant
2. It can be used for the manufacturing of unsaturated polyester resin, pesticides, sour agents and amino acids
3. It can be used as sour agent, mostly used in combination with citric acid. It can be applied to raw noodles products and fruit juice drinking with the maximum usage amount of 0.6g/kg; it can also be used for carbonated drinks with the maximum usage amount of 0.3g/kg.
4. 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.
5. It can be used as acidity regulator of food with strong effect of anti-bacterial and anti-corrosive. It can also be used as acidizing agent, anti-thermal oxidation additives, curing accelerators, spices. When being used as the acid substance of solid beverage gas production agent, the resultant bubble is long-lasting and delicate; it can also applied to fine chemical intermediates of medicine and optics bleaching agents. It is used for the production of antidote, sodium dimercaptosuccinate and the drug Fersamal that used for the treatment of small red blood cell anemia. In addition, it is also used for the production of unsaturated polyester resin.
6. It can be used for calibration of standard alkaline solution. It can be used for separation of thorium from cerium, lanthanum, praseodymium and rubidium. It can be applied to synthetic resin. It can also be used as mordant and antioxidant. | [Production method]
There are many ways to produce fumaric acid in industry. Its main source is through the oxidation of benzene (or butylene) to generate maleic acid (or maleic anhydride) in the presence of the catalyst, followed by isomerization. Send the benzene (or 80% butene) together with excess air into a fluidized bed or fixed bed reactor for oxidation reaction to generate maleic anhydride. The recycled acid was absorbed into maleic acid. Then after going through decolorization filtering, maleic acid is subject to isomerization under the action of the thiourea catalyst. The reactant undergoes filtration, washing and drying to obtain fumaric acid.
Ammonium persulfate-ammonium bromide mixtures or metal salts, amine salts, mercaptans and 10-20% hydrochloric acid can be used as the isomerization catalyst.
Carbohydrates such as sucrose, glucose, maltose, after undergoing fermentation by Rhizopus nigrocans can also used for manufacturing of fumaric acid. With the method of sugar fermentation, 1t products need to consume 8 ton of grain, which is quite uneconomical. Domestic research has taken liquid paraffin instead of food fermentation, using the liquid wax with high C16-C18 content as carbon source, after 80-88 h of fermentation, can obtain a conversion rate of liquid wax of about 50% and extraction rate of 50% or more. Furfural way: take furfural as the raw material; go through sodium chlorate oxidation to obtain it. For details: supply 58.5 g of KClO3 powder to a 250 mL flask; add an appropriate amount of V2O5/MoO3 (0.8: 1) catalyst and 100 mL of a 0.5 mol/L hydrochloric acid solution. Under continuous stirring at 110 °C, add dropwise of 20 mL of furfural at a speed of 1 mL/min. After the completion of dropping, continue the reaction for 2h and then cool to room temperature; filter, and the filtrate is recovered. The filter cake is placed in 100mL distilled water, crushed, filtered to get the crude fumaric acid, followed by dilute hydrochloric acid recrystallization to get the finished product. |
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