Itaconic acid: Difference between revisions

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{{Short description|Organic compound used in the production of synthetic resins}}
{{short description|A naturally occurring organic compound}}
{{Chembox
{{DISPLAYTITLE:Itaconic acid}}
| verifiedrevid = 477239679
| Name = Itaconic acid
| ImageFile = Itaconic acid.png
| ImageSize = 200px
| ImageAlt = Skeletal formula of itaconic acid
| ImageFile1 = Itaconic acid 3D ball.png
| ImageSize1 = 200px
| ImageAlt1 = Ball-and-stick model of the itaconic acid molecule
| IUPACName = 2-Methylidenebutanedioic acid
| OtherNames = Methylenesuccinic acid
| Section1 =


| CasNo = 97-65-4
[[File:2-methylenesuccinic_acid_200.svg|thumb|right|Structural formula of itaconic acid]]
| PubChem = 2048
| ChemSpiderID = 1968
| UNII = 0TQU766K2D
| ChEBI = 30802
| ChEMBL = 1231667
| SMILES = C=C(C(=O)O)CC(=O)O
| InChI = 1S/C5H6O4/c6-4(7)2-1-3-5(8)9/h1-2H2,(H,6,7)(H,8,9)
| InChIKey = KJXVUZOKDWTXBL-UHFFFAOYSA-N


| Section2 =
'''Itaconic acid''' is a naturally occurring organic compound with the formula C<sub>5</sub>H<sub>6</sub>O<sub>4</sub>. It is a white solid that is soluble in water and is used as a precursor to various polymers and resins. Itaconic acid is also known as methylenesuccinic acid.


| C=5 | H=6 | O=4
==Structure and properties==
| Appearance = White crystalline solid
Itaconic acid is an unsaturated dicarboxylic acid. It has a [[carboxylic acid]] group at each end of the molecule and a [[methylenic group]] in the middle, which gives it its unsaturated character. The presence of the double bond in the methylene group makes itaconic acid reactive and useful in polymerization reactions.
| Density = 1.573 g/cm³
| MeltingPt = 165-168 °C
| BoilingPt = 268 °C
| Solubility = Soluble in water


| Section3 =  
==Production==
Itaconic acid is produced industrially by the fermentation of carbohydrates such as glucose using the fungus ''[[Aspergillus terreus]]''. This biological process is favored due to its sustainability and the renewable nature of the raw materials used.


| MainHazards = Irritant
==Applications==
}}
Itaconic acid is used in the production of [[polymer]]s and [[resin]]s. It is a monomer that can be polymerized to form [[polyitaconic acid]] or copolymerized with other monomers to create various [[copolymer]]s. These materials are used in the manufacture of [[adhesive]]s, [[coating]]s, and [[sealant]]s.


'''Itaconic acid''' is an [[organic compound]] with the [[IUPAC nomenclature|IUPAC name]] 2-methylidenebutanedioic acid. It is a white crystalline solid that is soluble in water and is primarily used in the production of synthetic resins.
==Biological role==
In addition to its industrial applications, itaconic acid is also found in nature as a metabolite in the [[tricarboxylic acid cycle]] (TCA cycle) in some [[bacteria]] and [[fungi]]. It is involved in the [[metabolic pathway]]s of these organisms and plays a role in their energy production processes.


== Production ==
==Related pages==
Itaconic acid is produced industrially by the fermentation of [[carbohydrates]] such as [[glucose]] using the fungus ''[[Aspergillus terreus]]''. This process is considered to be more environmentally friendly compared to traditional petrochemical methods.
* [[Carboxylic acid]]
 
* [[Polymer]]
== Applications ==
Itaconic acid is used in the manufacture of various products, including:
* [[Synthetic resins]]
* [[Plastics]]
* [[Adhesives]]
* [[Coatings]]
* [[Detergents]]
 
It is also used as a building block for the synthesis of other chemicals, such as [[methyl methacrylate]] and [[ethyl acrylate]].
 
== Chemical Properties ==
Itaconic acid has the chemical formula C₅H₆O₄ and a molecular weight of 130.10 g/mol. It has a melting point of 165-168 °C and a boiling point of 268 °C. The compound is known for its ability to polymerize, making it useful in the production of [[polymer]]s and [[copolymer]]s.
 
== Biological Role ==
In addition to its industrial applications, itaconic acid has been found to play a role in the [[immune system]]. It is produced by [[macrophages]] during [[inflammation]] and has been shown to have antimicrobial properties.
 
== Related Pages ==
* [[Organic compound]]
* [[Fermentation]]
* [[Fermentation]]
* [[Synthetic resin]]
* [[Polymer]]
* [[Macrophage]]
* [[Inflammation]]
== See Also ==
* [[Methyl methacrylate]]
* [[Ethyl acrylate]]
* [[Aspergillus terreus]]
* [[Aspergillus terreus]]


[[Category:Organic compounds]]
[[Category:Organic compounds]]
[[Category:Carboxylic acids]]
[[Category:Dicarboxylic acids]]
[[Category:Industrial processes]]
[[Category:Monomers]]
[[Category:Biotechnology]]
 
{{medicine-stub}}

Latest revision as of 05:54, 16 February 2025

A naturally occurring organic compound



Structural formula of itaconic acid

Itaconic acid is a naturally occurring organic compound with the formula C5H6O4. It is a white solid that is soluble in water and is used as a precursor to various polymers and resins. Itaconic acid is also known as methylenesuccinic acid.

Structure and properties[edit]

Itaconic acid is an unsaturated dicarboxylic acid. It has a carboxylic acid group at each end of the molecule and a methylenic group in the middle, which gives it its unsaturated character. The presence of the double bond in the methylene group makes itaconic acid reactive and useful in polymerization reactions.

Production[edit]

Itaconic acid is produced industrially by the fermentation of carbohydrates such as glucose using the fungus Aspergillus terreus. This biological process is favored due to its sustainability and the renewable nature of the raw materials used.

Applications[edit]

Itaconic acid is used in the production of polymers and resins. It is a monomer that can be polymerized to form polyitaconic acid or copolymerized with other monomers to create various copolymers. These materials are used in the manufacture of adhesives, coatings, and sealants.

Biological role[edit]

In addition to its industrial applications, itaconic acid is also found in nature as a metabolite in the tricarboxylic acid cycle (TCA cycle) in some bacteria and fungi. It is involved in the metabolic pathways of these organisms and plays a role in their energy production processes.

Related pages[edit]