Glutaconic acid
Grundinformationen
- CAS
1724-02-3- Standard-SMILES
O=C(O)/C=C/CC(=O)O- InChIKey
XVOUMQNXTGKGMA-OWOJBTEDSA-N- Summenformel
- C5H6O4
- Durchschnittliche Molmasse
- 130,1 g/mol
- Monoisotopische Masse
- 130,02660867
Überblick
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-).
Namen und Bezeichner
- Bevorzugter Name
- Glutaconic acid
- IUPAC
- (E)-pent-2-enedioic acid
- Englischer Name
- Glutaconic acid
- Summenformel
- C5H6O4
- Molmasse
- 130.1
Namen und Synonyme
Glutaconic acid1724-02-32-Pentenedioic acid(2E)-pent-2-enedioic acidpent-2-enedioic acid2E-pentenedioic acidCHEBI:24309DTXSID40862740RefChem:922299DTXCID70811463(E)-pent-2-enedioic acid628-48-8
Weitere Namen anzeigen
C02214(E)-glutaconicaci2-Pentenedioic acid,(2E)-
trans-Glutaconic acid(E)-glutaconic acidPent-2-ene-1,5-dioic acidtrans-Glutaconate(E)-GlutaconatePent-2-ene-1,5-dioicacid2-Pentenedioic acid, (2E)-(E)-2-Pentenedioic acid
Datenbank-Bezeichner
- CAS
1724-02-3、505-36-2、628-48-8- PubChem CID
- 5280498
- DTXSID
DTXSID70211883- ChEMBL
CHEMBL557347- ChEBI
CHEBI:24309- UNII
- NOH8K33D47
- EC Number
- 217-027-0
- Nikkaji
- J7.761E、J95.462D
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -0,3
- Polarare Oberfläche (TPSA)
- 74,6 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 9
- Formalladung
- 0
- Komplexität
- 147
Experimentelle und physikochemische Eigenschaften
LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Dicarboxylic acids [FA0117]
Melting Point133 - 135 °C
Physical DescriptionSolid
Physikochemische Eigenschaften
- Schmelzpunkt
- 137 · 137-139 °C (lit.)
- Siedepunkt
- 413.8 · 413.8±28.0 °C(Predicted)
- Dichte
- 1.384 · 1.384±0.06 g/cm3(Predicted)
- storage temp.
- Sealed in dry,Room Temperature
- Löslichkeit
- DMSO (Slightly), Water (Slightly)
- pka
- 1 · pK1:3.77;pK2:5.08 (25°C)
- Aggregatzustand
- Solid
- Farbe
- White to Off-White
- Stabilität
- Light Sensitive
- InChI
- 1S/C5H6O4/c6-4(7)2-1-3-5(8)9/h1-2H,3H2,(H,6,7)(H,8,9)/b2-1+
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Toxikologische Informationen
Health EffectsChronically high levels of glutaconic acid are associated with Glutaric Aciduria Type I.
Toxicity Summary
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).
Sicherheitsdaten
- wgk
- 3
- hs_code
- 2917198090
- safety_code
- 22-24/25
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
Cellular LocationsExtracellular
Verwendung und Herstellung
UsesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Anwendungen
Verwendentrans-Glutaconic Acid is used in the synthesis of iso and azokainoids which act as agonists for glutamate receptors. E-isomer of Glutaconic Acid (G596945).
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