Itaconic acid

Itaconic acid: Itaconic acid

IUPAC name

2-Methylidenebutanedioic acid

Identifiers

CAS number 97-65-4^Y

PubChem 811

ChemSpider 789^Y

KEGG C00490^Y

ChEBI CHEBI:30838^Y

ChEMBL CHEMBL359159^Y

Jmol-3D images Image 1

SMILES

O=C(O)C(=C)CC(=O)O

InChI

InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h1-2H2,(H,6,7)(H,8,9)^Y
Key: LVHBHZANLOWSRM-UHFFFAOYSA-N^Y
InChI=1/C5H6O4/c1-3(5(8)9)2-4(6)7/h1-2H2,(H,6,7)(H,8,9)
Key: LVHBHZANLOWSRM-UHFFFAOYAS

Properties

Molecular formula C₅H₆O₄

Molar mass 130.099 g/mol

Appearance White crystals

Y acid (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Itaconic acid, or methylenesuccinic acid, is an organic compound. Itaconic acid is a white crystalline powder that is soluble in water, and partially soluble in methanol, ethanol, or acetone<ref?>. Itaconic acid is a naturally occurring compound, non-toxic, and readily biodegradable. The name itaconic was devised as an anagram of aconitic.

Historically, itaconic acid was obtained by the distillation of citric acid. Since the 1960s, it is produced industrially by fermentation of carbohydrates such as glucose using Aspergillus terreus. As such, it is a fully sustainable industrial building block. It is primarily used as a co-monomer in the production of styrene-butadiene-acrylonitrile and acrylate latexes with applications in the paper and architectural coating industry.

Since Cargill, the last of the U.S. companies to manufacture itaconic acid, exited the business, itaconic acid has mainly been procured by importing the product directly from China where it is still made by several different companies. The largest supplier/importer and distributor of itaconic acid today in the U.S. is Miami Chemical who stocks material in many warehouses across the United States.

Categories:
Alkenes
Dicarboxylic acids
Monomers

Itaconic acid


IUPAC name 2-Methylidenebutanedioic acid
Identifiers
CAS number	97-65-4^Y
PubChem	811
ChemSpider	789^Y
KEGG	C00490^Y
ChEBI	CHEBI:30838^Y
ChEMBL	CHEMBL359159^Y
Jmol-3D images	Image 1
SMILES O=C(O)C(=C)CC(=O)O
InChI InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h1-2H2,(H,6,7)(H,8,9)^Y Key: LVHBHZANLOWSRM-UHFFFAOYSA-N^Y InChI=1/C5H6O4/c1-3(5(8)9)2-4(6)7/h1-2H2,(H,6,7)(H,8,9) Key: LVHBHZANLOWSRM-UHFFFAOYAS
Properties
Molecular formula	C₅H₆O₄
Molar mass	130.099 g/mol
Appearance	White crystals
Y acid (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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Look at other dictionaries:

itaconic acid — it a*con ic ac id, n. (Chem.) The unsaturated dicarboxylic acid {CH2=C(COOH)CH2.COOH}, also called {methylenesuccynic acid} and {propylene dicarboxylic acid}. [PJC] … The Collaborative International Dictionary of English
itaconic acid — [it΄ə kän′ik] n. [arbitrary transposition of aconitic (< ACONITE + IC)] a white crystalline material, CH2:C(COOH)CH2 COOH, prepared by the fermentation of sugar with a special mold: it is used in making resins and plasticizers … English World dictionary
itaconic acid — noun a crystalline carboxylic acid; occurs in some fermentations of sugars • Hypernyms: ↑acid * * * | ̷ ̷ ̷ ̷| ̷ ̷ nik noun Etymology: International Scientific Vocabulary, anagram of aconitic : a crystalline dicarboxylic acid HOOCC( . CH2)CH2COOH … Useful english dictionary
itaconic acid — itakono rūgštis statusas T sritis chemija formulė CH₂=C(COOH)CH₂COOH atitikmenys: angl. itaconic acid rus. итаконовая кислота ryšiai: sinonimas – 2 metilenbutano dirūgštis … Chemijos terminų aiškinamasis žodynas
itaconic acid — The decarboxylation product of cis aconitic acid. SYN: methylenesuccinic acid. * * * it·a·con·ic acid .it ə .kän ik n a crystalline dicarboxylic acid C5H6O4 obtained usu. by fermentation of sugars with molds of the genus Aspergillus … Medical dictionary
itaconic acid — noun Etymology: International Scientific Vocabulary, anagram of aconitic acid, C3H3(COOH)3, from aconite Date: circa 1872 a crystalline dicarboxylic acid C5H6O4 obtained usually by fermentation of sugars with molds (genus Aspergillus) and used as … New Collegiate Dictionary
itaconic acid — /it euh kon ik/, Chem. a colorless crystalline compound, C5H6O4, obtained by fermentation, soluble in water, alcohol, and acetone: used as an intermediate in the formation of fibers, resins, etc. [1860 65; rearrangement of the letters of aconitic … Universalium
itaconic acid — noun one of the isomeric dicarboxylic acids produced by the distillation of citric acid, or as metabolites by microorganisms, CH=C(COH) CHCOH … Wiktionary
itaconic — adjective Of or pertaining to itaconic acid or its derivatives See Also: itaconate … Wiktionary
Itaconic — It a*con ic, a. [From aconitic, by transposition of the letters.] (Chem.) Pertaining to, or designating, an acid, {C5H6O4}, which is obtained as a white crystalline substance by decomposing aconitic and other organic acids. [1913 Webster] … The Collaborative International Dictionary of English

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Itaconic acid

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