I29204
Itaconic acid
≥99%
Synonym(s):
Methylenesuccinic acid
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About This Item
Linear Formula:
HO2CCH2C(=CH2)CO2H
CAS Number:
Molecular Weight:
130.10
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
202-599-6
Beilstein/REAXYS Number:
1759501
MDL number:
Product Name
Itaconic acid, ≥99%
InChI key
LVHBHZANLOWSRM-UHFFFAOYSA-N
InChI
1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h1-2H2,(H,6,7)(H,8,9)
SMILES string
OC(=O)CC(=C)C(O)=O
assay
≥99%
autoignition temp.
1472 °F
mp
165-168 °C (lit.)
density
1.573 g/mL at 25 °C (lit.)
Quality Level
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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.
signalword
Danger
hcodes
Hazard Classifications
Eye Dam. 1
Storage Class
11 - Combustible Solids
wgk
WGK 1
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Graft copolymerization, characterization, and degradation of cassava starch-g-acrylamide itaconic acid superabsorbents
Lanthong P, et al.
Carbohydrate Polymers, 66(2), 229-245 (2006)
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)
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)
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
Jahminy Sasikaran et al.
Nature chemical biology, 10(5), 371-377 (2014-03-25)
Itaconate (methylenesuccinate) was recently identified as a mammalian metabolite whose production is substantially induced during macrophage activation. This compound is a potent inhibitor of isocitrate lyase, a key enzyme of the glyoxylate cycle, which is a pathway required for the
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