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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
217-027-0
Beilstein/REAXYS Number:
1759560
MDL number:
Product Name
Glutaconic acid, 97% (T)
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
SMILES string
OC(=O)C\C=C\C(O)=O
assay
97% (T)
functional group
carboxylic acid
Quality Level
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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).
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.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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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)
6-Chloro-2(2H)-pyranone: a new 2(2H)-pyranone synthon.
Biagetti M, et al.
Tetrahedron Letters, 44(3), 607-610 (2003)
Crystal and molecular structure of glutaconic acid.
Thomas L and Srikrishnan T.
Journal of Chemical Crystallography, 33(9), 689-693 (2003)
Theoretical studies of molecular structure and vibrational spectra of glutaconic acid.
Atalay Y, et al.
Journal of Molecular Structure, 787(1), 90-95 (2006)
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
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