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About This Item
Empirical Formula (Hill Notation):
C5H4O3
CAS Number:
Molecular Weight:
112.08
UNSPSC Code:
12162002
NACRES:
NA.23
PubChem Substance ID:
EC Number:
210-459-0
Beilstein/REAXYS Number:
1835
MDL number:
InChI key
AYKYXWQEBUNJCN-UHFFFAOYSA-N
InChI
1S/C5H4O3/c1-3-2-4(6)8-5(3)7/h2H,1H3
SMILES string
CC1=CC(=O)OC1=O
vapor density
4 (vs air)
assay
98%
form
liquid
Quality Level
bp
213-214 °C (lit.)
mp
6-10 °C (lit.)
density
1.247 g/mL at 25 °C (lit.)
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General description
Citraconic anhydride is a derivative of maleic anhydride and is also known as 2-methylmaleic anhydride. It is highly reactive due to the presence of anhydride groups and can undergo hydrolysis, esterification, amidation, and addition reactions. It can be used as a crosslinking agent to create covalent bonds between polymer chains, enhancing the mechanical strength and thermal stability of the polymer network. They arepotential tools for bioconjugation and immobilization of bioactive molecules.
Application
Citraconic anhydride can be used:
- As an electrolyte additive for high-temperature pouch lithium-ion batteries. Citraconic anhydride reduces the interfacial impedance of pouch cells during high-temperature storage and enhances their stability.
- As a pH-sensitive linker to surface functionalization of biomolecules used in drug delivery systems. The high pH sensitivity of citraconic anhydride conjugates is attributed to the presence of a double bond that restricts the separation between the amide and carboxylic acid groups.
- As a reagent to synthesize new thiopyrano[2,3-d][1,3]thiazole derivatives via hetero-Diels–Alder reactions. These thiopyrano derivatives exhibit diverse biological activities such as anticancer, antiviral, and antitrypanosomal.
- As a co-monomer in the ring-opening polymerization with d-xylose 3,5-anhydrosugar derivative to form novel sugar-derived polyesters, with up to 100% renewable content. This can serve as a sustainable feedstock for polymer synthesis.
signalword
Danger
hcodes
Hazard Classifications
Eye Dam. 1 - Resp. Sens. 1 - Skin Corr. 1B - Skin Sens. 1
Storage Class
8A - Combustible corrosive hazardous materials
wgk
WGK 3
flash_point_f
231.8 °F - closed cup
flash_point_c
111 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
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Macromolecules, 25, 102-102 (1992)
Cyclic Anhydrides as Powerful Tools for Bioconjugation and Smart Delivery
Maria Vittoria Spanedda and Line Bourel-Bonnet
Bioconjugate Chemistry, 32, 482-496 (2021)
Raphael Haase et al.
PloS one, 12(6), e0179217-e0179217 (2017-06-13)
Injury of the glomerular filter causes proteinuria by disrupting the sensitive interplay of the glomerular protein network. To date, studies of the expression and trafficking of glomerular proteins have been mostly limited to in vitro or histologic studies. Here, we
Citraconic acid and its anhydride-based hetero-Diels-Alder reactions in the synthesis of new thiopyrano [2, 3-d][1, 3] thiazole derivatives
Nataliya Zelisko, et al.
Synthetic Communications, 51, 964-970 (2021)
Polymers from Sugars and Cyclic Anhydrides: Ring-Opening Copolymerization of a d-Xylose Anhydrosugar Oxetane
Thomas M. McGuire, et al.
Macromolecules, 54, 5094-5105 (2021)
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