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Sigma-Aldrich

Itaconic anhydride

95%

Synonym(s):

2-Methylenesuccinic anhydride

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About This Item

Empirical Formula (Hill Notation):
C5H4O3
CAS Number:
2170-03-8
Molecular Weight:
112.08
Beilstein/REAXYS Number:
2212
EC Number:
218-518-2
MDL number:
MFCD00005530
UNSPSC Code:
12162002
PubChem Substance ID:
24855441
NACRES:
NA.23

Quality Level

200

assay

95%

form

solid

bp

114-115 °C/12 mmHg (lit.)

mp

66-68 °C (lit.)

SMILES string

C=C1CC(=O)OC1=O

InChI

1S/C5H4O3/c1-3-2-4(6)8-5(3)7/h1-2H2

InChI key

OFNISBHGPNMTMS-UHFFFAOYSA-N

Gene Information

human ... FNTA(2339) , PGGT1B(5229)

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General description

Itaconic anhydride (ITA) is a biobased material that is obtained from renewable resources. It is produced from the pyrolysis of citric acid or by fermenting carbohydrates which forms itanoic acid. Itanoic acid can be dehydrated to form an anhydride. It is relatively more reactive that maleic anhydride and can be used as an alternating monomer that facilitates the introduction of polar functionalities in polymers.

Application

ITA can be copolymerized with methacrylate terminated poly(lactic acid) (PLA) for potential usage in packaging and biomedical applications. It can also facilitate the production of reactive polyesters which can be used as starting materials in telechelics, cross-linking agents and macromonomers.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Stable biocompatible cross-linked fluorescent polymeric nanoparticles based on AIE dye and itaconic anhydride
Li H, et al.
Colloids and Surfaces. B, Biointerfaces, 121, 347-353 (2014)
Synthesis and characterization of itaconic anhydride and stearyl methacrylate copolymers
Shang S, et al.
Polymer, 50(14), 3119-3127 (2009)
Green polymer chemistry: lipase-catalyzed synthesis of bio-based reactive polyesters employing itaconic anhydride as a renewable monomer
Yamaguchi S, et al.
Polymer Journal, 46(1), 2-2 (2014)
Copolymers of itaconic anhydride and methacrylate-terminated poly (lactic acid) macromonomers
Wallach JA and Huang SJ
Biomacromolecules, 1(2), 174-179 (2000)
Feng Tian et al.
European journal of pharmacology, 873, 172989-172989 (2020-02-08)
Renal fibrosis is an inevitable course of all kinds of progressive chronic kidney disease (CKD). Itaconic acid is an endogenous metabolite that has shown anti-inflammatory and antioxidant effects. 4-octyl itaconate (OI), a derivative of itaconic acid with higher fat solubility
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