Itaconic acid - CAS 97-65-4
Catalog: |
BB042066 |
Product Name: |
Itaconic acid |
CAS: |
97-65-4 |
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 |
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. |
Related CAS: | 1887074-72-7 (Deleted CAS)
|
IUPAC Name: | 2-methylidenebutanedioic acid |
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. |
Molecular Weight: | 130.10 |
Molecular Formula: | C5H6O4 |
Canonical 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 |
Storage: | Store at -20°C under inert atmosphere |
MDL: | MFCD00004260 |
LogP: | 0.10190 |
GHS Hazard Statement: | H315 (15.69%): Causes skin irritation [Warning Skin corrosion/irritation] |
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 |
Publication Number | Title | Priority Date |
US-2016250134-A1 | Polymers and uses thereof | 20150227 |
US-2016052888-A1 | Substituted bicyclic compounds | 20140820 |
US-2016041102-A1 | Poly(methyl methacrylate)-supported polydiacetylene films as colorimetric and/or fluorescent detectors | 20140709 |
US-2015225354-A1 | Heterocyclic compound | 20140213 |
US-9428470-B2 | Heterocyclic compound | 20140213 |
PMID | Publication Date | Title | Journal |
29670287 | 20180401 | Electrophilic properties of itaconate and derivatives regulate the\xa0IκBζ-ATF3 inflammatory axis | Nature |
28102516 | 20170201 | Production of lovastatin and itaconic acid by Aspergillus terreus: a comparative perspective | World journal of microbiology & biotechnology |
27750034 | 20161101 | Genetic and biochemical insights into the itaconate pathway of Ustilago maydis enable enhanced production | Metabolic engineering |
27374498 | 20160712 | Itaconate Links Inhibition of Succinate Dehydrogenase with Macrophage Metabolic Remodeling and Regulation of Inflammation | Cell metabolism |
26358042 | 20160101 | 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 |
Complexity: | 158 |
Compound Is Canonicalized: | Yes |
Covalently-Bonded Unit Count: | 1 |
Defined Atom Stereocenter Count: | 0 |
Defined Bond Stereocenter Count: | 0 |
Exact Mass: | 130.02660867 |
Formal Charge: | 0 |
Heavy Atom Count: | 9 |
Hydrogen Bond Acceptor Count: | 4 |
Hydrogen Bond Donor Count: | 2 |
Isotope Atom Count: | 0 |
Monoisotopic Mass: | 130.02660867 |
Rotatable Bond Count: | 3 |
Topological Polar Surface Area: | 74.6 Å2 |
Undefined Atom Stereocenter Count: | 0 |
Undefined Bond Stereocenter Count: | 0 |
XLogP3: | -0.1 |
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