49360
Glutaconic acid
97% (T)
Synonym(s):
2-Pentenedioic acid
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About This Item
Linear Formula:
HOOCCH2CH=CHCOOH
CAS Number:
Molecular Weight:
130.10
Beilstein/REAXYS Number:
1759560
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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assay
97% (T)
SMILES string
OC(=O)C\C=C\C(O)=O
InChI
1S/C5H6O4/c6-4(7)2-1-3-5(8)9/h1-2H,3H2,(H,6,7)(H,8,9)/b2-1+
InChI key
XVOUMQNXTGKGMA-OWOJBTEDSA-N
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General description
Glutaconic acid, also known as 2-pentenedioic acid, is an unsaturated dicarboxylic acid. It is formed as one of the degradation products during the partial wet oxidation (PWO) of alkali lignin. The analysis of its crystal structure indicates that the compound exists predominantly in the trans-conformation. The geometric bond lengths and bond angles of glutaconic acid have been obtained using Hartree–Fock (HF), density functional calculations and IR spectral data.
Application
Glutaconic acid has been used in the preparation of CoA-substrate glutaconyl-CoA by reacting with acetyl-CoA. It may be used in the preparation of 6-chloro-2(2H)-pyranone by reacting with phosphorus pentachloride (PCl5).
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Certificates of Analysis (COA)
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Alkaline Partial Wet Oxidation of Lignin for the Production of Carboxylic Acids.
Demesa AG, et al.
Chemical Engineering & Technology, 38(12), 2270-2278 (2015)
Crystal and molecular structure of glutaconic acid.
Thomas L and Srikrishnan T.
Journal of Chemical Crystallography, 33(9), 689-693 (2003)
T M Lund et al.
Journal of neuroscience research, 77(1), 143-147 (2004-06-16)
Glutaric acidemia type 1 (GA1) is an autosomal recessively inherited deficiency of glutaryl-CoA dehydrogenase. Accumulating metabolites, 3-hydroxyglutaric (3-OH-GA), glutaric (GA), and trans-glutaconic (TG) acids, have been proposed to be involved in the development of the striatal degeneration seen in children
Bettina Gerstner et al.
Pediatric research, 57(6), 771-776 (2005-03-19)
Glutaryl-CoA dehydrogenase deficiency is an inherited metabolic disease characterized by elevated concentrations of glutaric acid (GA) and its metabolites glutaconic acid (GC) and 3-hydroxy-glutaric acid (3-OH-GA). Its hallmarks are striatal and cortical degeneration, which have been linked to excitotoxic neuronal
6-Chloro-2(2H)-pyranone: a new 2(2H)-pyranone synthon.
Biagetti M, et al.
Tetrahedron Letters, 44(3), 607-610 (2003)
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