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2-butenedioic acid is an important kind of organic chemical raw materials as well as the intermediate of fine chemical products.
2-butenedioic acid is also an important kind of derivatives of maleic anhydride, being widely used in food, coatings, resins and plasticizers.
2-butenedioic acid, used as souring agent, can be applied to soft drinks, western-style wine, cold drinks, fruit juice concentrate, canned fruit, pickles and ice cream.
CAS Number: 110-17-8
Molecular Formula: C4H4O4
Molecular Weight: 116.07
EINECS Number: 203-743-0
Synonyms: Boiling point, Chemical shift, Corrosion, Crystal structure, Density, Diamagnetic susceptibility, Formula unit, Fusion temperature, Heat of sublimation, Magnetic anisotropy, Magnetic susceptibility, Melting temperature, Molar conductivity, Nuclear quadrupole resonance spectroscopy, Phase transition, Quadrupole coupling, Space group, Surface tension, Transition enthalpy, Unit cell, Unit cell parameter, Vapor pressure, Viscosity, 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
2-butenedioic acid 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.
2-butenedioic acid is an unsaturated dicarbonic acid and is part of the citric acid cycle.
2-butenedioic 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.
2-butenedioic 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.
2-butenedioic acid as an additive is regulated under the Codex Alimentarius General Standard for Food Additives (GSFA), a collection of internationally recognized standards.
2-butenedioic acid is an organic dicarboxylic acid with the formula C₄H₄O₄, commonly known in two geometric isomer forms: maleic acid (cis) and fumaric acid (trans).
2-butenedioic acid is widely used in chemical, food, and polymer industries.
The two isomers have different physical and chemical properties.
2-butenedioic acid contains a carbon–carbon double bond (C=C) with two carboxylic acid groups (–COOH) attached.
The position of these groups determines whether it is maleic acid or fumaric acid.
This geometric isomerism affects reactivity and solubility.
Physically, 2-butenedioic acid appears as a white crystalline solid that is highly soluble in water, while fumaric acid is less soluble and forms more stable crystals.
Both are odorless or have a slight acidic odor.
Their melting points and stability differ due to structural arrangement.
2-Butenedioic acid exhibits typical acidic behavior due to its two carboxyl groups.
2-butenedioic acid can donate protons and form salts (maleates and fumarates).
This makes it useful in buffering and chemical reactions.
2-butenedioic acid is more reactive due to the cis configuration, which allows intramolecular interactions.
Fumaric acid is more thermodynamically stable.
These differences influence their industrial applications.
2-butenedioic acid can participate in addition and polymerization reactions through its double bond.
2-butenedioic acid is used as a building block in polymer chemistry.
This enables production of resins and coatings.
2-butenedioic acid is used in food, pharmaceutical, and industrial applications, depending on the isomer.
2-butenedioic acid is commonly used as a food additive.
2-butenedioic acid is more often used in chemical synthesis.
2-butenedioic acid is best described as a dicarboxylic acid with geometric isomerism, used as a chemical intermediate and functional additive in multiple industries.
2-butenedioic acid or trans-butenedioic 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.
2-butenedioic acids E number is E297.[3] The salts and esters are known as fumarates.
Fumarate can also refer to the C4H2O2−4 ion (in solution). Fumaric acid is the trans isomer of butenedioic acid, while maleic acid is the cis isomer.
2-butenedioic acid shows different acid dissociation behavior depending on the isomer.
2-butenedioic acid has a much stronger first dissociation due to intramolecular stabilization.
2-butenedioic acid dissociates more evenly because of its trans structure.
The cis structure of maleic acid allows intramolecular interactions, which can facilitate certain reactions such as cyclization.
This makes it more reactive in dehydration and addition reactions.
2-butenedioic acid is often preferred in chemical synthesis.
2-butenedioic acid, due to its trans configuration, forms more stable crystal lattices.
This results in higher thermal stability and lower solubility.
These properties are important in solid-state applications.
The double bond in 2-butenedioic acid allows participation in copolymerization reactions.
2-butenedioic acid can be incorporated into polymer backbones.
This is useful in producing resins and functional polymers.
Derivatives of 2-butenedioic acid are used in unsaturated polyester resins.
These resins are important in coatings, composites, and fiberglass materials.
The double bond enables crosslinking reactions.
2-butenedioic acid can also act as a chelating or coordinating species in some chemical systems.
Its carboxyl groups can interact with metal ions.
This contributes to its use in certain formulations.
In aqueous systems, it contributes to acidification and buffering capacity.
2-butenedioic acid can control pH in formulations.
This is relevant in both industrial and food applications.
Melting point: 298–300 °C (subl.) (lit.)
Boiling point: 137.07 °C (rough estimate)
Density: 1.62 g/cm³
Vapor pressure: 1.7 mm Hg (165 °C)
Refractive index: 1.5260 (estimate)
FEMA: 2488 (Fumaric acid)
Flash point: 230 °C
Storage temperature: Store below +30 °C
Solubility: 95% ethanol 0.46 g/10 mL, clear, colorless
Form: Fine crystalline powder
pKa: 3.02, 4.38 (at 25 °C)
Color: White
pH: 3.19 (1 mM); 2.57 (10 mM); 2.03 (100 mM)
Odor: Odorless
Odor type: Odorless
Biological source: Synthetic
Explosive limit: 40%
Water solubility: 0.63 g/100 mL (25 °C)
Merck: 14,4287
JECFA number: 618
BRN: 605763
Stability: Stable at room temperature; decomposes around 230 °C; incompatible with strong oxidizing agents, bases, reducing agents; combustible
Cosmetics ingredients functions: Buffering
Cosmetic Ingredient Review (CIR): Fumaric acid (CAS 110-17-8)
InChI: 1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+
InChIKey: VZCYOOQTPOCHFL-OWOJBTEDSA-N
SMILES: OC(=O)C=CC(O)=O
LogP: −4.02 at 20 °C
2-butenedioic acid white, odorless granules or crystalline powder.
2-butenedioic acid is soluble in alcohol, slightly soluble in water and in ether, and very slightly soluble in chloroform.
2-butenedioic acid is used as a replacement for tartaric acid.
2-butenedioic acid 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.
2-butenedioic acid in which the C2C double bond has E geometry.
2-butenedioic acid is an intermediate metabolite in the citric acid cycle.
2-Butenedioic acid exhibits geometric (cis–trans) isomerism, resulting in two distinct compounds: maleic acid and fumaric acid.
The cis form (maleic acid) has both carboxyl groups on the same side of the double bond.
The trans form (fumaric acid) has them on opposite sides, leading to greater stability.
2-butenedioic acid shows strong intramolecular hydrogen bonding, which affects its physical properties.
This interaction increases its solubility in water.
2-butenedioic acid also makes maleic acid more reactive in certain chemical processes.
2-butenedioic acid, in contrast, forms strong intermolecular hydrogen bonds, resulting in higher melting point and lower solubility.
2-butenedioic acid is more thermodynamically stable than maleic acid.
This stability makes it suitable for food and pharmaceutical uses.
2-butenedioic acid can undergo addition reactions at the carbon–carbon double bond.
It reacts with nucleophiles, halogens, and other reagents.
These reactions are important in polymer and organic synthesis.
2-butenedioic acid can easily convert to maleic anhydride upon heating.
This dehydration reaction is widely used in industrial chemistry.
2-butenedioic acid is a key intermediate in resin production.
2-Butenedioic acid can form esters, salts, and polymers through its carboxylic acid groups.
These derivatives are used in coatings, adhesives, and plastic materials.
This increases its industrial versatility.
2-butenedioic acid also shows buffering and acidifying properties in aqueous systems.
It can control pH in certain formulations.
This is useful in food and pharmaceutical applications.
In biological systems, fumaric acid is part of the Krebs (citric acid) cycle, an essential metabolic pathway.
This highlights its importance beyond industrial chemistry.
2-butenedioic acid is naturally present in living organisms.
2-butenedioic acid is a versatile unsaturated dicarboxylic acid with distinct isomer-dependent properties, widely used in synthesis, polymer chemistry, food applications, and biological systems.
2-butenedioic acid is considered more suitable for food and pharmaceutical use due to its stability and lower reactivity.
2-butenedioic acid is more commonly used in industrial chemical processes.
This distinction is important in practical applications.
2-butenedioic acid is a chemically versatile compound whose properties depend strongly on its cis–trans isomerism, enabling its use in polymers, synthesis, food applications, and industrial chemistry.
Uses Of 2-butenedioic acid:
Occurs in many plants, essential to vegetable and tissue respiration.
2-butenedioic acid is used as an antioxidant.
2-butenedioic acid is used in food products as an acidifier with an acid type of taste that blends particularly well with caramellic or sugarsweetened products, baked products, etc.
2-butenedioic 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.
2-butenedioic acid is the intermediate of pharmaceutical and optical bleaching agents and other fine chemicals. Neutralization of fumaric acid with sodium carbonate can generate sodium fumarate ([17013-01-3]), and then replaced with ferrous sulfate to get iron fumarate, being the drug Fersamal used for the treatment of small red blood cell anemic.
2-butenedioic acid, as a food additive-sourness agent, used in soft drinks, fruit sugar, jelly, ice cream with most of them used in combination with sourness agent, citric acid.
The monosidum salt made from the reaction between fumaric acid and sodium hydroxide can also used as sour seasoning, also used as the intermediate of synthetic resin and mordant.
2-butenedioic acid is included in many dairy-based products.
These include dairy drinks such as chocolate milk, cocoa, eggnog, condensed milk and whey protein beverages.
2-butenedioic acid also may be added to clotted cream, milk and cream powders and milk and cream analogues (substitutes).
2-butenedioic 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 2-butenedioic acid, and so can preserved eggs and egg-based desserts such as custard.
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.
2-butenedioic acid is widely used in the form of its isomers, especially fumaric acid and maleic acid, across different industries.
2-butenedioic acid is used in the food industry as an acidulant and pH regulator.
It provides a sour taste and improves flavor stability.
2-butenedioic acid is commonly used in beverages, baked goods, and confectionery.
In pharmaceutical applications, 2-butenedioic acid and its derivatives are used in medicines and supplements.
They are involved in formulations for certain treatments and metabolic functions.
This is related to their role in biological systems.
2-butenedioic acid is used as an intermediate in chemical manufacturing.
2-butenedioic acid is converted into maleic anhydride, which is a key raw material.
This supports production of resins, coatings, and plastics.
2-butenedioic acid derivatives are used in unsaturated polyester resins.
These resins are applied in fiberglass, coatings, and composite materials.
The double bond enables crosslinking and polymer formation.
In adhesives and coatings, maleic acid derivatives improve adhesion and chemical resistance.
They help form durable polymer networks.
This enhances product performance.
The compound is used in water treatment and cleaning formulations as a pH regulator and chelating agent.
It helps control acidity and metal ion interactions.
This supports formulation stability.
Fumaric acid is applied in animal feed and agriculture as an acidifier.
It helps improve digestion and feed preservation.
This supports livestock health.
In cosmetics and personal-care products, it may be used as a pH adjuster and stabilizer.
It helps maintain formulation balance.
This contributes to product stability.
2-Butenedioic acid derivatives are also used in printing inks and surface coatings.
They help improve binding and film formation.
This enhances coating quality.
2-butenedioic acid is used wherever acidification, polymer formation, chemical intermediates, and pH control are required across food, pharmaceutical, and industrial applications.
Safety Profile Of 2-butenedioic acid:
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.
2-butenedioic 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.
2-butenedioic acid presents moderate health hazards, mainly related to irritation and chemical reactivity.
The level of hazard differs between the two isomers, with maleic acid generally being more reactive and irritating.
Proper handling precautions are recommended.
Skin contact may cause irritation, especially with maleic acid.
Symptoms can include redness, burning, or dryness.
Protective gloves should be worn during handling.
Eye contact can cause serious irritation or damage.
Exposure may lead to redness, pain, and tearing.
Immediate rinsing with plenty of water is required.
Inhalation of dust may cause respiratory irritation.
Symptoms can include coughing, throat irritation, and discomfort.
Adequate ventilation and dust control should be used.
Ingestion may cause gastrointestinal irritation.
Symptoms may include nausea, abdominal pain, or vomiting.
Medical attention should be sought if significant exposure occurs.
2-butenedioic acid is considered more hazardous and may cause stronger irritation and potential systemic effects.
2-butenedioic acid is generally regarded as lower risk and is approved for food use in controlled amounts.
This distinction is important in safety assessment.
