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I29204

Sigma-Aldrich

Itaconic acid

≥99%

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Synonym(s):
Methylenesuccinic acid
Linear Formula:
HO2CCH2C(=CH2)CO2H
CAS Number:
97-65-4
Molecular Weight:
130.10
Beilstein:
1759501
EC Number:
202-599-6
MDL number:
MFCD00004260
UNSPSC Code:
12352100
PubChem Substance ID:
24896018
NACRES:
NA.22

Quality Level

200

Assay

≥99%

autoignition temp.

1472 °F

mp

165-168 °C (lit.)

density

1.573 g/mL at 25 °C (lit.)

SMILES string

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

InChI

1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h1-2H2,(H,6,7)(H,8,9)

InChI key

LVHBHZANLOWSRM-UHFFFAOYSA-N

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Application

Itaconic acid (IA) can be used:
  • As a comonomer in the polymerization of polyacrylonitrile (PAN) to promote the thermo-oxidative stabilization of polymer.
  • In combination with acrylamide to form (poly[acrylamide-co-(itaconicacid)]) to synthesize biodegradable superabsorbent polymers.
  • To synthesize biobased polyester composite in fabric industry.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H318

Precautionary Statements

P280 - P305 + P351 + P338

Hazard Classifications

Eye Dam. 1

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Mechanism and kinetics of the stabilization reactions of itaconic acid-modified polyacrylonitrile
Ouyang Q, et al.
Polymer Degradation and Stability, 93(8), 1415-1421 (2008)
Selective and flexible transformation of biomass-derived platform chemicals by a multifunctional catalytic system.
Frank M A Geilen et al.
Angewandte Chemie (International ed. in English), 49(32), 5510-5514 (2010-06-30)
Fully Biobased Composites of an Itaconic Acid Derived Unsaturated Polyester Reinforced with Cotton Fabrics
Dai Z, et al.
ACS sustainable chemistry & engineering, 6(11), 15056-15063 (2018)
Reddithota J Krupadam et al.
Environmental science and pollution research international, 19(5), 1841-1851 (2011-12-31)
Microcystins (MCs; cyclic heptapeptides) are produced by freshwater cyanobacteria and cause public health concern in potable water supplies. There are more than 60 types of MCs identified to date, of which MC-LR is the most common found worldwide. For MC-LR
Tobias Klement et al.
Microbial cell factories, 11, 43-43 (2012-04-07)
In the last years, the biotechnological production of platform chemicals for fuel components has become a major focus of interest. Although ligno-cellulosic material is considered as suitable feedstock, the almost inevitable pretreatment of this recalcitrant material may interfere with the
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