N-(Aminocarbonyl)-L-glutamic acid(carglumic acid)

• CAS: 1188-38-1
• Catalog Number: ACM1188381
• Category: Main Products
• Molecular Weight: 190.15
• Molecular Formula: C₆H₁₀N₂O₅
• Synonyms: (S)-2-Ureidopentanedioic acid; N-Carbamyl-L-glutamic Acid; N-Carbamyl-L-glutamic acid; (2S)-2-(carbamoylamino)pentanedioic acid
• IUPAC Name: (2S)-2-(carbamoylamino)pentanedioicacid
• Canonical SMILES: C(CC(=O)O)C(C(=O)O)NC(=O)N
• InChI Key: LCQLHJZYVOQKHU-VKHMYHEASA-N
• Boiling Point: 438.1ºC at 760 mmHg
• Flash Point: 218.8ºC
• Density: 1.499g/cm³
• EC Number: 601-569-3
• Exact Mass: 190.05900
• Hazard Statements: Xi: Irritant
• Safety Description: 26-36/37
• WGK Germany: 3

Case Study

N-Carbamyl-L-Glutamic Acid Used to Prepare Hydrogen-Bonded Ferroelectric Liquid Crystals

G. Sangameswari, et al. Liquid Crystals, 2018, 45(3), 431-449.

The combination of carbamyl glutamic acid (CGA) and p-n-alkyl/alkoxybenzoic acid (BA/BAO) can form hydrogen-bonded ferroelectric liquid crystals (HBFLCs). In this work, 14 compounds containing two homologues were designed and synthesized, namely CGA+nBAO and CGA+nBA series. The CGA+nBAO series exhibits cholesteric, smectic X*, smectic C* and smectic G* phases, while CGA+nBA exhibits cholesteric and smectic G* phases.
Preparation and spectroscopic studies of HBFLC compounds
· The pentyl to dodecyl carbon number alkyloxy/alkyl benzoic acids(nBAO/nBA) were found to form hydrogen bonds with a di-carboxylic acid, N-Carbamyl-L-Glutamic acid (CGA), resulting in the creation of 14 hydrogen-bonded homologues referred as CGA+5BAO, CGA+6BAO, CGA+7BAO, CGA +8BAO, CGA+9BAO, CGA+10BAO, CGA+11BAO, CGA+12BAO, CGA+2BA, CGA+4BA, CGA+5BA, CGA+6BA, CGA+7BA and CGA+8BA.
· The preparation route for CGA+nBAO is illustrated in the figure, with a similar procedure used for the preparation of CGA+nBA homologues featuring alkyl benzoic acids instead of alkyloxy benzoic acids.
· FTIR spectra were recorded for all 14 mesogens using KBr pellet at room temperature. In the pure compounds, the carboxylic acid was found to exist in a monomeric form, with the stretching vibration of C=O observed at 1760 cm-1. The formation of hydrogen bonds between carboxylic acids and benzoic acids led to a decrease in the carbonyl frequency of saturated acids in the hydrogen-bonded compounds.