1188-38-1

Basic information

• Product Name: N-CARBAMYL-L-GLUTAMIC ACID
• Synonyms: N-CARBAMYL-L-GLUTAMIC ACID;carbamino-l-glutamicacid;carbamylglutamicacid;n-(aminocarbonyl)-l-glutamicaci;n-carbamylglutamate;ureidoglutaricacid;N-carbamyl-L-glutamic acid crystalline;(2S)-2-(aminocarbonylamino)pentanedioic acid
• CAS NO: 1188-38-1
• Molecular Formula: C₆H₁₀N₂O₅
• Molecular Weight: 190.15
• EINECS: 1308068-626-2
• Product Categories: A - H;Amino Acids;Modified Amino Acids;CARBAGLU
• Mol File: 1188-38-1.mol

Chemical Properties

• Melting Point: 174°
• Boiling Point: 438.1 °C at 760 mmHg
• Flash Point: 218.8 °C
• Appearance: /
• Density: 1.499g/cm³
• Vapor Pressure: 6.7E-09mmHg at 25°C
• Refractive Index: 1.544
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly, Sonicated)
• PKA: 3.71±0.10(Predicted)
• CAS DataBase Reference: N-CARBAMYL-L-GLUTAMIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: N-CARBAMYL-L-GLUTAMIC ACID(1188-38-1)
• EPA Substance Registry System: N-CARBAMYL-L-GLUTAMIC ACID(1188-38-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37
• WGK Germany: 3
• RTECS: LZ9870000
• Hazardous Substances Data: 1188-38-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-Carbamyl-L-glutamic acid serves as a carbamylphosphate synthetase activator, playing a crucial role in the urea cycle. This activation is vital for the detoxification of ammonia in the body, making it an essential component in the treatment of acute hyperammonemia.
Additionally, N-Carbamyl-L-glutamic acid has demonstrated protective effects against ammonia intoxication, further emphasizing its importance in medical applications for conditions characterized by abnormally high levels of ammonia in the bloodstream.

InChI:InChI=1/C6H10N2O5/c7-6(13)8-3(5(11)12)1-2-4(9)10/h3H,1-2H2,(H,9,10)(H,11,12)(H3,7,8,13)/t3-/m0/s1

Upstream product

• 56-86-0 L-glutamic acid 
• 57-13-6 urea 
• 590-28-3 potassium cyanate 
• 917-61-3 sodium isocyanate 
• 142-47-2 monosodium glutamate 
• 462-88-4 N-carbamoyl-β-alanine 

Downstream Products

• 372-75-8 Citrulline 
• 911658-62-3 N-carbamoyl-L-glutamic acid diethyl ester 
• 56-86-0 L-glutamic acid 
• 17027-50-8 3-[(4S)-2,5-dioxoimidazolidin-4-yl]propionic acid 

Relevant articles and documents

Supramolecular assembly in the chiral N-carbamoyl compound 2-ureido-pentanedioic acid

The compound 2-ureido-pentanedioic acid was synthesized and characterized by FT-IR and NMR spectra. Its molecular structure was solved by single crystal X-ray diffraction. In the title compound, C6H10N2O5, the chiral structure is stabilized by intermolecular O-H···O and N-H···O hydrogen bonds in a supramolecular assembly formed by infinite chains parallel to the bc plane with graph set C(4) connected by amide-acid dimers R22(8) into a three-dimensional network.

Rapid and efficient microwave-assisted synthesis of N-carbamoyl-L-amino acids

A rapid and efficient method for the synthesis of N-carbamoyl-L-amino acids is reported. The procedure, involving the reaction between urea and α-amino acids sodium salts, was performed under microwave conditions using an unmodified domestic microwave oven. A careful study of the operative conditions indicated proline (1d) as the less reactive substrate and phenylglycine (1e) as the more reactive one among all the α-amino acids tested. Substitution of urea with potassium cyanate produced a low conversion into the corresponding N-carbamoyl derivative, and a possible explanation of this result is reported. Copyright Taylor & Francis Group, LLC.

PROCESS FOR THE PURIFICATION OF CARGLUMIC ACID AND INTERMEDIATE OF THIS PROCESS

Method of purification of carglumic acid, substance formula I, contains the following steps: a) Dissolution of carglumic acid in dimethyl sulfoxide; b) Addition of a precipitation solvent; c) Isolation of the precipitated solvate of carglumic acid with dimethyl sulfoxide; d) Release of carglumic acid from the solvate by the help of water, possibly a mixture of water and an organic solvent, possibly a mixture of water and an organic or mineral acid, possibly a mixture of water, an organic acid and a mineral acid, possibly by an activity of an organic acid, possibly by an activity of mixture of water, a mineral acid and an organic solvent.

PROCESS FOR THE SYNTHESIS OF CARGLUMIC ACID

The invention relates to a process for the synthesis of carglumic acid from L-glutamic acid and sodium cyanate by treatment with a lithium compound in an aqueous medium. The process according to the invention is easily industrially scalable, and is faster and cheaper than the known procedures. Formula (I)

One-pot synthesis method of N-carbamylglutamate

The invention discloses a one-pot synthesis method of N-carbamylglutamate, and belongs to the technical field of synthesis. The one-pot synthesis method of N-carbamylglutamate includes the steps thatwater serves as solvent, glutamic acid and cyanate serve as raw materials, alkali is added to adjust the pH value to 11-13, after a reaction is conducted for 2-4 hours at 50-90 DEG C, a mixture is cooled to room temperature and then stands for 10-15 hours, acid is added to adjust the pH value to make the mixture neutral, hydantoic acid serving as a catalyst is added, the mixture stands for 1-4 hours at 10-20 DEG C, and after filtration, recrystallization and drying are conducted, a product is obtained; the mole ratio of glutamic acid to cyanate is 1:(1.0-1.6), and the mole ratio of hydantoic acid to glutamic acid is (0.5-0.8):1. According to the one-pot synthesis method of N-carbamylglutamate, glutamic acid and cyanate serve as the raw materials, and through one-pot synthesis, N-carbamylglutamate is synthesized through the recrystallization after nucleophilic addition, the melting point obtained through tests is 152-155 DEG C, the yield is 55%, and the content is greater than 92%. Theone-pot synthesis method of N-carbamylglutamate has the advantages that the raw materials are cheap and easy to get, operation is simple, reaction conditions are mild, and the one-pot synthesis methodof N-carbamylglutamate is suitable for industrial production.