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G3407

Sigma-Aldrich

Glutaric acid

99%

Synonyme(s) :

1,3-Propanedicarboxylic acid, 1,5-Pentanedioic acid

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About This Item

Formule linéaire :
HOOC(CH2)3COOH
Numéro CAS:
110-94-1
Poids moléculaire :
132.11
Numéro Beilstein :
1209725
Numéro CE :
203-817-2
Numéro MDL:
MFCD00004410
Code UNSPSC :
12352100
ID de substance PubChem :
24895125
Nomenclature NACRES :
NA.22

Pureté

99%

Point d'ébullition

200 °C/20 mmHg (lit.)

Pf

95-98 °C (lit.)

Solubilité

water: soluble 5 mg/mL, clear to slightly hazy, colorless to faintly yellow
alcohol: soluble(lit.)
chloroform: soluble(lit.)

Chaîne SMILES 

OC(=O)CCCC(O)=O

InChI

1S/C5H8O4/c6-4(7)2-1-3-5(8)9/h1-3H2,(H,6,7)(H,8,9)

Clé InChI

JFCQEDHGNNZCLN-UHFFFAOYSA-N

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Catégories apparentées

Description générale

Glutaric acid is a pentanedioic acid. On exposure to X-rays, glutaric acid crystals generate two stable free radicals. These free radicals have been investigated by electron nuclear double resonance (ENDOR) technique. Presence of glutaric acid in urine and plasma is an indicator of type I glutaric aciduria (GA-I).
Glutaric acid is an aliphatic acid used as building block for the synthesis of polyesters, and polyamides.

Glutaric acid (Pentanedioic Acid) is a linear dicarboxylic acid. It has been prepared by oxidizing cyclopentane, cyclopentanol and cyclopentanone.
Glutaric acid is formed as an intermediate during the catabolism of lysine in mammals. Electron spin resonance spectra of radical (CO2H)CH2CH2CH(CO2H formed in glutaric acid crystal after γ-irradiation is reported to remains trapped in it. Polymorphism of Glycine-glutaric acid co-crystals has been studied by single crystal X-ray diffraction and Raman spectroscopy.

Application

Glutaric acid may be employed as starting reagent in the synthesis of glutaric anhydride.
Glutaric acid may be used for the following studies:
  • Complexation with DL-lysine. Complexes have been reported to possess zwitterionic lysinium ions (positively charged) and semi-glutarate ions (negatively charged).
  • Synthesis of complexes with L-arginine and L-histidine.
  • Preparation of glycine-glutaric acid co-crystals. Phase transition studies of these cocrystals have been reported by single-crystal X-ray diffraction, polarized Raman spectroscopy and differential scanning calorimetry.

Pictogrammes

Corrosion
GHS05

Mention d'avertissement

Danger

Mentions de danger

H314

Classification des risques

Eye Dam. 1 - Skin Corr. 1A

Code de la classe de stockage

8A - Combustible corrosive hazardous materials

Classe de danger pour l'eau (WGK)

WGK 1

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

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Electron spin resonance of (CO2H) CH2CH2CH (CO2H) in irradiated glutaric acid.
Horsfield A, et al.
Molecular Physics, 4(2), 169-175 (1961)
Exploring rearrangements along the fragmentation of glutaric acid negative ion: a combined experimental and theoretical study
Basem K et al.
Rapid Communications in Mass Spectrometry, 24, 1198-1206 (2010)
The metabolism of glutaric acid-3-C14 by the intact rat.
D C HOBBS et al.
The Journal of biological chemistry, 230(2), 655-660 (1958-02-01)
N T Saraswathi et al.
Acta crystallographica. Section B, Structural science, 57(Pt 6), 842-849 (2001-11-22)
The complexes of glutaric acid with L-arginine and L-histidine (two crystal forms) exhibit different stoichiometries and ionization states. The aggregation patterns in two of the crystals are remarkably similar to those observed earlier in similar structures, while the pattern in
Eagleson M.
Concise Encyclopedia Chemistry, 461-461 (1994)
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