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Merck
CN

259926

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
UNSPSC Code:
12162002
NACRES:
NA.23
PubChem Substance ID:
24855441
EC Number:
218-518-2
Beilstein/REAXYS Number:
2212
MDL number:
MFCD00005530

Key Documents

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InChI key

OFNISBHGPNMTMS-UHFFFAOYSA-N

InChI

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

SMILES string

C=C1CC(=O)OC1=O

assay

95%

form

solid

bp

114-115 °C/12 mmHg (lit.)

Quality Level

200

Gene Information

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

Related Categories

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

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX4252
MKCW9860
MKCT1262
MKCT4515
MKCR6912

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Synthesis and characterization of itaconic anhydride and stearyl methacrylate copolymers
Shang S, et al.
Polymer, 50(14), 3119-3127 (2009)
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
Copolymers of itaconic anhydride and methacrylate-terminated poly (lactic acid) macromonomers
Wallach JA and Huang SJ
Biomacromolecules, 1(2), 174-179 (2000)
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)
Sameh M Osman et al.
Chemistry Central journal, 6(1), 85-85 (2012-08-10)
Microwave irradiation as an alternative heat source is now a well-known method in synthetic chemistry. Microwave heating has emerged as a powerful technique to promote a variety of chemical reactions, offering reduced pollution, low cost and offer high yields together
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