U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C5H4O3
Molecular Weight 112.0835
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CITRACONIC ANHYDRIDE

SMILES

CC1=CC(=O)OC1=O

InChI

InChIKey=AYKYXWQEBUNJCN-UHFFFAOYSA-N
InChI=1S/C5H4O3/c1-3-2-4(6)8-5(3)7/h2H,1H3

HIDE SMILES / InChI

Approval Year

PubMed

PubMed

TitleDatePubMed
pH-Sensitive siRNA nanovector for targeted gene silencing and cytotoxic effect in cancer cells.
2010-12-06
Loss of heterozygosity and SOSTDC1 in adult and pediatric renal tumors.
2010-11-16
A mesoporous silica nanoparticle with charge-convertible pore walls for efficient intracellular protein delivery.
2010-06-04
Chemical modification of lysine residues in lysozyme may dramatically influence its amyloid fibrillation.
2010-04
Comparative study for the detection of C4d in paraffin-embedded renal allograft biopsies by immunohistochemical techniques.
2010-03
Citraconic anhydride: a new antigen retrieval solution.
2010-01
Equivalence of protein inventories obtained from formalin-fixed paraffin-embedded and frozen tissue in multidimensional liquid chromatography-tandem mass spectrometry shotgun proteomic analysis.
2009-08
Effects of citraconylation on enzymatic modification of human proinsulin using trypsin and carboxypeptidase B.
2009-07-03
Protein reactivity of 3,4-dihydroxyphenylacetaldehyde, a toxic dopamine metabolite, is dependent on both the aldehyde and the catechol.
2009-07
Immunohistochemical observation of co-expression of E- and N-cadherins in rat organogenesis.
2008-10-29
Gene expression reveals two distinct groups of anal carcinomas with clinical implications.
2008-04-08
Enhanced intracellular delivery of quantum dot and adenovirus nanoparticles triggered by acidic pH via surface charge reversal.
2008-04
A new antigen retrieval technique for human brain tissue.
2008
Development of an optimal antigen retrieval protocol for immunohistochemistry of retinoblastoma protein (pRB) in formalin fixed, paraffin sections based on comparison of different methods.
2007-12
Histochemistry for placenta research: theory and application.
2007-08
Improvement of activity and stability of chloroperoxidase by chemical modification.
2007-05-18
A protein nanocarrier from charge-conversion polymer in response to endosomal pH.
2007-05-02
Stepwise modification of lysine residues of glucose oxidase with citraconic anhydride.
2006-11-15
Modification of lysyl side chains using citraconic anhydride.
2006-10-01
Increased thermal and organic solvent tolerance of modified horseradish peroxidase.
2006-04
A new antigen retrieval method using citraconic anhydride for immunoelectron microscopy: localization of surfactant pro-protein C (proSP-C) in the type II alveolar epithelial cells.
2005-05-24
On the Diels-Alder reactions of pentadienyl maleates and citraconates.
2005-04-07
Reversing the effects of formalin fixation with citraconic anhydride and heat: a universal antigen retrieval method.
2005-01
The native oligomeric organization of alpha-crystallin, is it necessary for its chaperone function?
2004-12
Chemical modification of lysine residues in Bacillus licheniformis alpha-amylase: conversion of an endo- to an exo-type enzyme.
2004-11-30
Definition of the structural elements in plasminogen required for high-affinity binding to apolipoprotein(a): a study utilizing surface plasmon resonance.
2004-09-28
Ceramic microreactors for heterogeneously catalysed gas-phase reactions.
2004-08
Chemical modification of glucose oxidase: possible formation of molten globule-like intermediate structure.
2004-03-12
Citraconylation--a simple method for high protein sequence coverage in MALDI-TOF mass spectrometry.
2003-06-13
Characterization of different reactive lysines in bovine heart mitochondrial porin.
2002-12
Identification of a critical lysine residue in apolipoprotein B-100 that mediates noncovalent interaction with apolipoprotein(a).
2001-09-28
Acylation of Bowman-Birk soybean proteinase inhibitor by unsaturated fatty acid derivatives.
2001-04
Patents
Name Type Language
METHYLMALEIC ANHYDRIDE
HSDB  
Preferred Name English
CITRACONIC ANHYDRIDE
INCI  
Official Name English
3-METHYL-2,5-FURANDIONE,
Systematic Name English
2,5-FURANDIONE, 3-METHYL-
Systematic Name English
METHYLMALEIC ANHYDRIDE [HSDB]
Common Name English
NSC-6182
Code English
Code System Code Type Description
ECHA (EC/EINECS)
210-459-0
Created by admin on Wed Apr 02 18:00:00 GMT 2025 , Edited by admin on Wed Apr 02 18:00:00 GMT 2025
PRIMARY
EPA CompTox
DTXSID8060660
Created by admin on Wed Apr 02 18:00:00 GMT 2025 , Edited by admin on Wed Apr 02 18:00:00 GMT 2025
PRIMARY
CAS
616-02-4
Created by admin on Wed Apr 02 18:00:00 GMT 2025 , Edited by admin on Wed Apr 02 18:00:00 GMT 2025
PRIMARY
PUBCHEM
12012
Created by admin on Wed Apr 02 18:00:00 GMT 2025 , Edited by admin on Wed Apr 02 18:00:00 GMT 2025
PRIMARY
FDA UNII
105NP7PMXX
Created by admin on Wed Apr 02 18:00:00 GMT 2025 , Edited by admin on Wed Apr 02 18:00:00 GMT 2025
PRIMARY
MESH
C035824
Created by admin on Wed Apr 02 18:00:00 GMT 2025 , Edited by admin on Wed Apr 02 18:00:00 GMT 2025
PRIMARY
NSC
6182
Created by admin on Wed Apr 02 18:00:00 GMT 2025 , Edited by admin on Wed Apr 02 18:00:00 GMT 2025
PRIMARY
HSDB
5716
Created by admin on Wed Apr 02 18:00:00 GMT 2025 , Edited by admin on Wed Apr 02 18:00:00 GMT 2025
PRIMARY