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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:
2212
EC Number:
218-518-2
MDL number:
MFCD00005530
UNSPSC Code:
12162002
PubChem Substance ID:
24855441
NACRES:
NA.23
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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.[1][2]

Application

ITA can be copolymerized with methacrylate terminated poly(lactic acid) (PLA) for potential usage in packaging and biomedical applications.[3] It can also facilitate the production of reactive polyesters which can be used as starting materials in telechelics, cross-linking agents and macromonomers.[4]

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX4252
MKCW9860
MKCT1262
MKCT4515
MKCR6912

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

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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