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G3407

Sigma-Aldrich

Glutaric acid

99%

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Synonym(s):
1,3-Propanedicarboxylic acid, 1,5-Pentanedioic acid
Linear Formula:
HOOC(CH2)3COOH
CAS Number:
Molecular Weight:
132.11
Beilstein/REAXYS Number:
1209725
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

99%

bp

200 °C/20 mmHg (lit.)

mp

95-98 °C (lit.)

solubility

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

SMILES string

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)

InChI key

JFCQEDHGNNZCLN-UHFFFAOYSA-N

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1 of 4

This Item
851450604860607851
vibrant-m

G3407

Glutaric acid

vibrant-m

851450

D-(+)-Glucuronic acid γ-lactone

vibrant-m

604860

L-Glutamic acid-13C5

vibrant-m

607851

L-Glutamic acid-13C5,15N

solubility

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

solubility

water: soluble 25 mg/mL, clear, colorless

solubility

-

solubility

-

mp

95-98 °C (lit.)

mp

172-175 °C (lit.)

mp

205 °C (dec.) (lit.)

mp

205 °C (dec.) (lit.)

bp

200 °C/20 mmHg (lit.)

bp

-

bp

-

bp

-

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

General description

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.

pictograms

Corrosion

signalword

Danger

hcodes

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1A

Storage Class

8A - Combustible, corrosive hazardous materials

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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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)
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
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)
Polymorphism of ?glycine-glutaric acid? co-crystals: the same phase at low temperatures and high pressures.
Zakharov BA, et al.
CrystEngComm, 15(9), 1693-1697 (2013)
Eagleson M.
Concise Encyclopedia Chemistry, 461-461 (1994)

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