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G3407

Sigma-Aldrich

Glutaric acid

99%

Synonym(s):

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

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About This Item

Linear Formula:
HOOC(CH2)3COOH
CAS Number:
110-94-1
Molecular Weight:
132.11
Beilstein/REAXYS Number:
1209725
EC Number:
203-817-2
MDL number:
MFCD00004410
UNSPSC Code:
12352100
PubChem Substance ID:
24895125
NACRES:
NA.22

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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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
GHS05

signalword

Danger

hcodes

H314

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

Certificates of Analysis (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)
ENDOR Studies in Molecular Crystals. I. Glutaric Acid at 4.2? K.
Kwiram AL.
J. Chem. Phys., 55(5), 2484-2495 (1971)
X-ray studies on crystalline complexes involving amino acids and peptides. XXXVII. Novel aggregation patterns and effect of chirality in the complexes of DL-and L-lysine with glutaric acid.
Saraswathi NT, et al.
Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials, 53(1), 366-371 (2001)
D H Morton et al.
American journal of medical genetics, 41(1), 89-95 (1991-10-01)
We have diagnosed type I glutaric aciduria (GA-I) in 14 children from 7 Old Order Amish families in Lancaster County, Pennsylvania. An otherwise rare disorder, GA-I appears to be a common cause of acute encephalopathy and cerebral palsy among the
Eagleson M.
Concise Encyclopedia Chemistry, 461-461 (1994)
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