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:
1759560
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Assay
97% (T)
functional group
carboxylic acid
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 Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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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.
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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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