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49360

Sigma-Aldrich

Glutaconic acid

97% (T)

Sinónimos:

2-Pentenedioic acid

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About This Item

Fórmula lineal:
HOOCCH2CH=CHCOOH
Número de CAS:
1724-02-3
Peso molecular:
130.10
Beilstein/REAXYS Number:
1759560
EC Number:
217-027-0
MDL number:
MFCD00002784
UNSPSC Code:
12352100
PubChem Substance ID:
57651185
NACRES:
NA.22

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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cis-Aconitic acid ≥98%

Sigma-Aldrich

A3412

cis-Aconitic acid

Crystal and molecular structure of glutaconic acid.
Thomas L and Srikrishnan T.
Journal of Chemical Crystallography, 33(9), 689-693 (2003)
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)
W Buckel et al.
FEBS letters, 148(1), 35-38 (1982-11-01)
The decarboxylation of glutaconyl-CoA to crotonyl-CoA in the anaerobic bacterium Acidaminococcus fermentans is catalysed by a membrane-bound, biotin-dependent enzyme which requires Na+ for activity. Inverted vesicles from A. fermentans accumulated Na+ only if glutaconyl-CoA was decarboxylated. The Na+ uptake was
Rui Pereira et al.
Metabolic engineering, 56, 130-141 (2019-09-25)
Improving the growth phenotypes of microbes in high product concentrations is an essential design objective in the development of robust cell factories. However, the limited knowledge regarding tolerance mechanisms makes rational design of such traits complicated. Here, adaptive laboratory evolution
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