Skip to Content
Merck
All Photos(2)

Documents

259926

Sigma-Aldrich

Itaconic anhydride

95%

Synonym(s):

2-Methylenesuccinic anhydride

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C5H4O3
CAS Number:
Molecular Weight:
112.08
Beilstein:
2212
EC Number:
MDL number:
UNSPSC Code:
12162002
PubChem Substance ID:
NACRES:
NA.23

Quality Level

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

Looking for similar products? Visit Product Comparison Guide

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

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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
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)
Synthesis and characterization of itaconic anhydride and stearyl methacrylate copolymers
Shang S, et al.
Polymer, 50(14), 3119-3127 (2009)

Articles

Innovation in dental restorative materials is driven by the need for biocompatible and natural-appearing restoration alternatives. Conventional dental materials like amalgam and composite resins have inherent disadvantages.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service