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

Specification:
| 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 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.

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