2301-52-2

Basic information

• Product Name: PHTHALYL-DL-GLUTAMIC ACID
• Synonyms: 3-dihydro-1,3-dioxo-2h-isoindol-2-yl)-2-((s)-pentanedioicaci;dl-glutaricaci;n-phthalyl-d,l-glutamicacid;n-phthalyl-dl-glutaminsaure;n-phthalylglutamicacid;nplg;2-PHTHALIMIDINO-GLUTARIC ACID;N-PHTHALOYL-DL-GLUTAMIC ACID
• CAS NO: 2301-52-2
• Molecular Formula: C13H11NO6
• Molecular Weight: 277.23
• EINECS: 218-952-2
• Product Categories: N-Substituted Maleimides, Succinimides & Phthalimides;N-Substituted Phthalimides
• Mol File: 2301-52-2.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 420.1°C (rough estimate)
• Appearance: /
• Density: 1.3459 (rough estimate)
• Refractive Index: 1.5500 (estimate)
• CAS DataBase Reference: PHTHALYL-DL-GLUTAMIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: PHTHALYL-DL-GLUTAMIC ACID(2301-52-2)
• EPA Substance Registry System: PHTHALYL-DL-GLUTAMIC ACID(2301-52-2)

Safety Data

• RTECS: MA3810000
• Hazardous Substances Data: 2301-52-2(Hazardous Substances Data)

Usage

General Description

Phthalyl-DL-glutamic acid, also known as monosodium glutamate, is a synthetic compound used as a flavor enhancer in foods. It is a sodium salt of the naturally occurring amino acid glutamic acid, and is widely used in the food industry to enhance the savory taste of various dishes. Monosodium glutamate has been controversial due to concerns about its potential negative health effects, although extensive scientific research has not found any conclusive evidence of harm. It is commonly used in processed foods, canned soups, and meat products to enhance flavor, and is considered safe for consumption in moderate amounts.

Upstream product

• 25830-77-7 N-phthaloyl-L-glutamic anhydride 
• 85-44-9 phthalic anhydride 
• 56-86-0 L-glutamic acid 
• 3343-28-0 N-phthaloylglutamic acid anhydride 
• 6893-26-1 D-Glutamic acid 
• 22509-74-6 N-ethoxycarbonylphthalimide 
• 171513-89-6 (R)-2-[(E)-1,3-diphenylprop-2-en-1-yl]-1H-isoindole-1,3-(2H)-dione 
• 1074-82-4 potassium phtalimide 
• 171513-90-9 (+)-1-Phthalimido-1,3-diphenylpropane 
• 617-65-2 Glutamic acid 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 3350-06-9 2-cyclopentenamine 
• 204922-61-2 2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-4-nitro-pentanedioic acid 5-ethyl ester 1-methyl ester 
• 100727-30-8 2-(cyclopent-2-en-1-yl)isoindoline-1,3-dione 

Downstream Products

• 35457-98-8 dimethyl L-2-(1,3-dioxo-2,3-dihydro-1H-2-isoindolyl)pentanedioate 
• 39739-04-3 dimethyl 2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-pentanedioate 
• 25830-77-7 N-phthaloyl-L-glutamic anhydride 
• 53987-25-0 N-phthaloyl-L-glutamic acid-γ-p-biphenylmethyl ester 
• 25830-78-8 N-phthaloyl-D-glutamic acid anhydride 
• 7607-72-9 2-phthalimidoglutaramic acid 
• 26581-81-7 3-(1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione 
• 26577-32-2 EM 138 
• 109932-21-0 N¹-phenyl-N²,N²-phthaloyl-L-isoglutamine-methyl ester 
• 539-95-7 N-L-γ-glutamyl-β-alanine nitrile 
• 75790-48-6 N-(γ-L-glutamyl)adamantanine 

Relevant articles and documents

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A Genetically Encoded Allysine for the Synthesis of Proteins with Site-Specific Lysine Dimethylation

Using the amber suppression approach, N?-(4-azidobenzoxycarbonyl)-δ,?-dehydrolysine, an allysine precursor is genetically encoded in E. coli. Its genetic incorporation followed by two sequential biocompatible reactions allows convenient synthesis of proteins with site-specific lysine dimethylation. Using this approach, dimethyl-histone H3 and p53 proteins have been synthesized and used to probe functions of epigenetic enzymes including histone demethylase LSD1 and histone acetyltransferase Tip60. We confirmed that LSD1 is catalytically active toward H3K4me2 and H3K9me2 but inert toward H3K36me2, and methylation at p53 K372 directly activates Tip60 for its catalyzed acetylation at p53 K120.

Absolute configuration of the enantiomers of 7-chloro-4-[[4-(diethylamino)-1-methylbutyl]amino]quinoline (chloroquine)

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Phthaloyl amino acids as anti-inflammatory and immunomodulatory prototypes

A series of phthalimide analogs were synthesized by derivatization of phthalic anhydride, a highly toxic substance, using a "one pot" condensation reaction to α-amino acids. All phthaloyl amino acid derivatives presented anti-oral inflammatory activity, but compounds 2e and 2g were found to possess the best activities comparable to thalidomide.Most of the compounds effectively suppressed nitric oxide production inmurine cells stimulatedwith lipopolysaccharide. N-phthaloyl amino acids did not exhibit any significant cytotoxicity in vitro when tested against tumor cells as well as a spleen cell culture of BALB/c mice. Compounds 2a, 2g, and 2h were able to inhibit TNF-α and IL-1β production by macrophages. At the same concentration, thalidomide did not exhibit significant inhibitory activity. Springer Science+Business Media 2013.

Light-Triggered Transformation of Molecular Baskets into Organic Nanoparticles

Discovering novel and functional photoresponsive materials is of interest for improving controlled release of molecules and scavenging toxic compounds for cleaning our environment or designing chemosensors. In this study, we report on the photoinduced decarboxylation of basket 16?, containing three glutamic acids at its rim. This concave compound is, in an aqueous environment (30 mm phosphate buffer at pH 7.0), monomeric (1H NMR DOSY, DLS) with glutamic acid residues randomly oriented about its rim (1H NMR and MM-OPLS3). The irradiation (300 nm) of 16? leads to the exclusive removal of its α-carboxylates to give amphiphilic 23? possessing γ-carboxylates. The photochemical transformation is a consecutive reaction with mono- and bis-decarboxylated products observed with 1H NMR spectroscopy and ESI mass spectrometry. Amphiphilic 23? is a preorganized molecule (MM-OPLS3) that, in water, aggregates into organic nanoparticles (ca. 50–200 nm in diameter; DLS, TEM and cryo-TEM) having a critical aggregation concentration of 12 μm (UV/Vis). As the transition of monomeric 16? into nanoparticulate 23? is triggered with light, we reasoned that stimuli-responsive formation of the soft material lends itself to nanotechnology applications such as controlled release or scavenging of targeted compounds.

Investigations of the Alignment Process of PBPMLG: 2H NMR Analysis Reveals a Thermoresponsive 90° Flip of the Polymer

The application of anisotropic parameters in NMR-spectroscopy enables the acquisition of spatial and angular information, complementary to those from conventional isotropic NMR-measurements. The use of alignment media is a well-established method for inducing anisotropy. PBPMLG is a recently discovered polyglutamate-based alignment medium, exhibiting thermoresponsive behavior in the lyotropic liquid crystalline (LLC) phase, thus offering potential for deeper understanding of the alignment process. We present one approach for investigating the thermoresponsive behavior by synthesizing specifically deuterated PBPMLG-isotopologues and their subsequent analyses using 2H NMR-spectroscopy. It was possible to relate the observed thermoresponsive behavior to a flip of the polymer with respect to the external magnetic field—an effect never observed before in glutamate-based polymeric alignment media. Furthermore, a solvent-induced temperature dependent gelation was verified in THF, which might provide yet another opportunity to manipulate the properties of this alignment medium in the future.

Synthesis method of thalidomide

The invention relates to an industrial synthesis method of thalidomide, and specifically discloses a method, which comprises: directly synthesizing a crude product thalidomide by using phthalic anhydride and L-glutamic acid as raw materials through a two-step reaction one-pot method, and then carrying out refining purifying to obtain a finished product. According to the present invention, thalidomide is synthesized by using the two-step reaction one-pot method, microwave heating and other special equipment are not required, and the synthesis of the thalidomide anhydride intermediate is not required, such that the intermediate reaction process is eliminated, the use of acetic anhydride is avoided, the operation is simplified, the labor intensity is reduced, the production efficiency is improved, the environmental protection is achieved, and the method has high economic and social value.