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49360

Sigma-Aldrich

Glutaconic acid

97% (T)

Synonym(s):

2-Pentenedioic acid

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5 G
₹35,321.00

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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Quality Level

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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This Item
8.22057K175028684
assay

97% (T)

assay

-

assay

≥98.5% (NaOH, titration)

assay

≥97.0% (T)

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

100

functional group

carboxylic acid

functional group

-

functional group

-

functional group

carboxylic acid

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.[1] The analysis of its crystal structure indicates that the compound exists predominantly in the trans-conformation.[2] The geometric bond lengths and bond angles of glutaconic acid have been obtained using Hartree–Fock (HF), density functional calculations and IR spectral data.[3]

Application

Glutaconic acid has been used in the preparation of CoA-substrate glutaconyl-CoA by reacting with acetyl-CoA.[4] It may be used in the preparation of 6-chloro-2(2H)-pyranone by reacting with phosphorus pentachloride (PCl5).[5]

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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Theoretical studies of molecular structure and vibrational spectra of glutaconic acid.
Atalay Y, et al.
Journal of Molecular Structure, 787(1), 90-95 (2006)
Crystal and molecular structure of glutaconic acid.
Thomas L and Srikrishnan T.
Journal of Chemical Crystallography, 33(9), 689-693 (2003)
6-Chloro-2(2H)-pyranone: a new 2(2H)-pyranone synthon.
Biagetti M, et al.
Tetrahedron Letters, 44(3), 607-610 (2003)
H Osaka et al.
Brain & development, 15(2), 125-127 (1993-03-01)
A 10-month-old male with glutaric aciduria type-1 (GA-1) is reported. This patient showed frequent partial motor seizures, irritability, and involuntary movements, including oral dyskinesia at the age of 3 months. On admission, magnetic resonance (MR) scanning revealed a chronic subdural
Alkaline Partial Wet Oxidation of Lignin for the Production of Carboxylic Acids.
Demesa AG, et al.
Chemical Engineering & Technology, 38(12), 2270-2278 (2015)

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