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Merck
CN

27429

Citraconic anhydride

≥99.0% (T)

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About This Item

Empirical Formula (Hill Notation):
C5H4O3
CAS Number:
616-02-4
Molecular Weight:
112.08
EC Number:
210-459-0
UNSPSC Code:
12162002
PubChem Substance ID:
24856577
Beilstein/REAXYS Number:
1835
MDL number:
MFCD00005522

Key Documents

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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

≥99.0% (T)

refractive index

n20/D 1.472

bp

213-214 °C (lit.)

mp

6-10 °C (lit.)

density

1.247 g/mL at 25 °C (lit.)

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Other Notes

For the reversible blocking of amino groups (e.g. lysine-side chain); Can be used to dissociate nucleoprotein complexes

pictograms

Health hazardCorrosion
GHS08,GHS05

signalword

Danger

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

Regulatory Information

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[49] Reaction of proteins with citraconic anhydride.
M Z Atassi et al.
Methods in enzymology, 25, 546-553 (1972-01-01)
P P Batra
The International journal of biochemistry, 23(12), 1375-1384 (1991-01-01)
The lysine residues were modified to varying degrees (50-91%) with citraconic anhydride to determine the extent of conformational change in ovalbumin. Major findings included: 1. Sixteen of the 20 lysine residues are located on the protein surface, while the remaining
Anthony S-Y Leong et al.
Pathology, 42(1), 77-81 (2009-12-23)
The introduction of heat-induced antigen retrieval has been a major milestone in diagnostic immunohistochemistry, enabling the application of many antibodies to fixed paraffin-embedded tissue sections. A number of important variables affect the preservation of tissue antigens, among which are analytical
Jian-Zhong Liu et al.
Protein engineering, design & selection : PEDS, 19(4), 169-173 (2006-02-03)
Horseradish peroxidase (HRP) was modified by maleic anhydride and citraconic anhydride. The thermal and organic solvent tolerances of native and modified enzyme were compared. These chemical modifications of HRP increased their thermostability both in aqueous buffer and some organic solvents
J K Shetty et al.
The Biochemical journal, 191(1), 269-272 (1980-10-01)
Modification of proteins with citraconic anhydride altered the electrostatic relationship between cationic epsilon-NH3+ groups of lysine residues of proteins and anionic phosphate groups of nucleic acids, thereby destabilizing the nucleoprotein complex. This procedure facilitated the separation of proteins from nucleic
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