Itaconic acid
Product Information
Molecular Formula
C5H6O4
Molecular Weight
130.10
Description
Itaconic acid, a dicarboxylic acid with a molecular formula of C5H6O4, plays a pivotal role as a precursor in the synthesis of bio-based polymers essential for drug delivery and tissue regeneration applications. Furthermore, its pharmacological potential extends to the treatment of debilitating conditions like rheumatoid arthritis and osteoarthritis.
Synonyms
Butanedioic acid, 2-methylene-; Butanedioic acid, methylene-; Succinic acid, methylene-; 2-Methylenesuccinic acid; 2-Methylidenebutanedioic acid; 2-Propene-1,2-dicarboxylic acid; 4-Hydroxy-2-methylene-4-oxobutanoic acid; Methylenebutanedioic acid; Methylenesuccinic acid; NSC 3357; Propylenedicarboxylic acid
IUPAC Name
2-methylidenebutanedioic acid
SMILES
C=C(CC(=O)O)C(=O)O
InChI
InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h1-2H2,(H,6,7)(H,8,9)
InChI Key
LVHBHZANLOWSRM-UHFFFAOYSA-N
Boiling Point
158-160°C at 12 Torr
Melting Point
162-164°C (dec.)
Purity
≥95%
Density
1.632 g/cm3
Solubility
Soluble in DMSO (Sparingly), Methanol (Slightly, Sonicated)
Appearance
White to Off-white Solid
Application
Used in copolymerization and to make resins, plasticizers, and lube oil additives; Used as a comonomer in the production of acrylic fibers and latex.
Storage
Store at -20°C under inert atmosphere
LogP
0.10190
Dissociation Constants
ACID DISSOCIATION CONSTANTS: 3.84 & 5.55
Odor
CHARACTERISTIC ODOR
Related CAS
1887074-72-7 (Deleted CAS)
Safety Information
Hazards
H318
Precautionary Statement
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501
Signal Word
Danger
Computed Properties
XLogP3
-0.1
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
3
Exact Mass
130.02660867 g/mol
Monoisotopic Mass
130.02660867 g/mol
Topological Polar Surface Area
74.6Ų
Heavy Atom Count
9
Formal Charge
0
Complexity
158
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
Covalently-Bonded Unit Count
1
Compound Is Canonicalized
Yes
Patents
| Publication Number | Title | Priority Date |
|---|---|---|
| US-2016250134-A1 | Polymers and uses thereof | 2015-02-27 |
| US-2016052888-A1 | Substituted bicyclic compounds | 2014-08-20 |
| US-2016041102-A1 | Poly(methyl methacrylate)-supported polydiacetylene films as colorimetric and/or fluorescent detectors | 2014-07-09 |
| US-2015225354-A1 | Heterocyclic compound | 2014-02-13 |
| US-9428470-B2 | Heterocyclic compound | 2014-02-13 |
| US-2015133451-A1 | Heterocyclic compound | 2013-11-08 |
| US-9321757-B2 | Heterocyclic compound | 2013-11-08 |
| US-2015038488-A1 | Syk inhibitors | 2013-07-31 |
| US-9376441-B2 | Substituted pyrrolidines as SYK inhibitors | 2013-07-31 |
| US-2016068620-A1 | Itaconic Acid Polymers | 2013-03-15 |
Literatures
| PMID | Publication Date | Title | Journal |
|---|---|---|---|
| 29670287 | 2018-04-01 | Electrophilic properties of itaconate and derivatives regulate the IκBζ-ATF3 inflammatory axis | Nature |
| 28102516 | 2017-02-01 | Production of lovastatin and itaconic acid by Aspergillus terreus: a comparative perspective | World journal of microbiology & biotechnology |
| 27750034 | 2016-11-01 | Genetic and biochemical insights into the itaconate pathway of Ustilago maydis enable enhanced production | Metabolic engineering |
| 27374498 | 2016-07-12 | Itaconate Links Inhibition of Succinate Dehydrogenase with Macrophage Metabolic Remodeling and Regulation of Inflammation | Cell metabolism |
| 26358042 | 2016-01-01 | Abolition of mitochondrial substrate-level phosphorylation by itaconic acid produced by LPS-induced Irg1 expression in cells of murine macrophage lineage | FASEB journal : official publication of the Federation of American Societies for Experimental Biology |
| 24781056 | 2014-01-01 | Inhibitors of the glyoxylate cycle enzyme ICL1 in Candida albicans for potential use as antifungal agents | PloS one |
| 22759642 | 2012-10-15 | Controlled release of lipase from Candida rugosa loaded into hydrogels of N-isopropylacrylamide and itaconic acid | International journal of pharmaceutics |
| 22885157 | 2012-10-01 | Preliminary assessment of the safety evaluation of novel pH-sensitive hydrogel | European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V |
| 23000746 | 2012-10-01 | Microbial Community-Level Physiological Profiles (CLPP) and herbicide mineralization potential in groundwater affected by agricultural land use | Journal of contaminant hydrology |
| 22814491 | 2012-09-01 | Analysis and quantification of ammonia-oxidizing bacteria community with amoA gene in sewage treatment plants | Journal of microbiology and biotechnology |
