Pentenedioic acid

HCID 74406
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Basic information

CAS
1724-02-3
Standard SMILES
O=C(O)C=CCC(=O)O
InChIKey
XVOUMQNXTGKGMA-UHFFFAOYSA-N
Molecular formula
C5H6O4
Average molar mass
130.1 g/mol
Monoisotopic mass
130.02660867

Overview

Glutaconic acid is an organic compound with general formula C5H6O4. The compound is a dicarboxylic acid and related with the fully saturated glutaric acid.

Names & identifiers

Preferred name
Pentenedioic acid
IUPAC
pent-2-enedioic acid
English name
Pent-2-ene-1,5-dioic acid
Molecular formula
C5H6O4
Molecular weight
130.1

Names & synonyms

Pentenedioic acidRefChem:1094559CHEBI:36129SCHEMBL218412-Pentenedioic acid,(2E)-SCHEMBL7619085XVOUMQNXTGKGMA-UHFFFAOYSA-NAKOS025243555DB-008609NS00015238Q27109839GLUTACONIC ACID
Show more names
pentene diacid(E)-glutaconic acid2-PENTENEDIOIC ACIDTRANS-GLUTACONIC ACIDpent-2-ene-1,5-dioic acidGlutaconic acid >=97.0% (T)Glutaconic acid (6CI, 7CI, 8CI)

Database identifiers

CAS
1724-02-3
PubChem CID
74406
DTXSID
DTXSID40862740

Properties

Computed structural properties

XLogP
-0.3
Topological polar surface area
74.6 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
4
Rotatable bonds
3
Heavy atoms
9

Physicochemical properties

Melting point
137 · 137-139 °C(lit.)
Boiling point
413.8 · 413.8±28.0 °C(Predicted)
Density
1.384 · 1.384±0.06 g/cm3(Predicted)
storage temp.
Amber Vial, Refrigerator
solubility
DMSO (Slightly), Methanol (Slightly)
pka
4.21 · 4.21±0.10(Predicted)

Safety & regulation

Toxicology

Health EffectsChronically high levels of glutaconic acid are associated with Glutaric Aciduria Type I.
Toxicity Summary · 1 item

Accumulating trans-glutaconic (TG) acids has been proposed to be involved in the development of the striatal degeneration seen in children with glutaric acidemia type 1 (GA1) via an excitotoxic mechanism. TG is neurotoxic and neurotoxicity is thought to be caused by an excitotoxic mechanism in which TG overactivates N-methyl-D-aspartate (NMDA) receptors. (A15451) In glutaric aciduria type 1, glutaconic acid accumulates, resulting in brain damage. (Wikipedia)

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
hs_code
2917198090
safety_code
22-24/25
Storage Class
11 - Combustible Solids

Chemistry & industry

Uses & manufacturing

UsesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Applications · 2 items

UsesGlutaconic 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 DescriptionGlutaconic 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.

Upstream & downstream products

Suppliers58 total

山东旭晨化工科技有限公司0533-15715337262 15715337262 · [email protected]
Hebei Chuanghai Biotechnology Co., Ltd+86-17732866630 · [email protected]
上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]
杭州摩库生物医药科技有限公司+86-057181025280; +8617767106207 · [email protected]
Shanghai Medfine Bio-pharmaceutical Co., Ltd+86-86-13013810076 +86-13013810076 · [email protected]

Additional notes

DefinitionChEBI: Glutaconic acid is a pentenedioic acid that is pent-2-ene substituted by carboxy groups at positions 1 and 5. It has a role as a human metabolite. It is a conjugate acid of a glutaconate(1-).

Related reactions

3 records
New reaction record

Compound notes

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