3085-92-5

Basic information

• Product Name: N-PHTHALOYL-DL-GLUTAMIC ANHYDRIDE
• Synonyms: LABOTEST-BB LT00138184;TIMTEC-BB SBB007749;PHTHALYL-DL-GLUTAMIC ANHYDRIDE;PHTHALOYL-DL-GLUTAMIC ACID ANHYDRIDE;PHT-DL-GLU-ANHYDRIDE;N-PHTHALYL-DL-GLUTAMIC ANHYDRIDE;N-PHTHALOYL-DL-GLUTAMIC ANHYDRIDE;2-(2,6-diketotetrahydropyran-3-yl)isoindoline-1,3-quinone
• CAS NO: 3085-92-5
• Molecular Formula: C13H9NO5
• Molecular Weight: 259.21
• EINECS: 222-088-1
• Product Categories: Thalidomide
• Mol File: 3085-92-5.mol
• Article Data: 19

Chemical Properties

• Melting Point: 197-201 °C(lit.)
• Boiling Point: 484.8°C at 760 mmHg
• Flash Point: 247°C
• Appearance: /
• Density: 1.554g/cm³
• Vapor Pressure: 1.48E-09mmHg at 25°C
• Refractive Index: 1.647
• CAS DataBase Reference: N-PHTHALOYL-DL-GLUTAMIC ANHYDRIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-PHTHALOYL-DL-GLUTAMIC ANHYDRIDE(3085-92-5)
• EPA Substance Registry System: N-PHTHALOYL-DL-GLUTAMIC ANHYDRIDE(3085-92-5)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-40
• Safety Statements: 23-26-36/37/39-45
• WGK Germany: 3
• RTECS: MA3900000
• Hazardous Substances Data: 3085-92-5(Hazardous Substances Data)

Usage

General Description

N-PHTHALOYL-DL-GLUTAMIC ANHYDRIDE is a chemical compound with a molecular structure consisting of a phthaloyl group attached to a DL-glutamic acid derivative. It is used as a reagent in organic synthesis and as a precursor in the production of pharmaceuticals and agrochemicals. N-PHTHALOYL-DL-GLUTAMIC ANHYDRIDE is known for its ability to undergo acylation and amidation reactions, making it a versatile building block in the synthesis of various organic compounds. Additionally, N-PHTHALOYL-DL-GLUTAMIC ANHYDRIDE is used in the development of drug delivery systems and in the preparation of peptide and protein conjugates for biomedical applications. Its unique chemical properties and potential applications make it an important tool in the field of organic chemistry and chemical engineering.

InChI:InChI=1/C13H9NO5/c15-10-6-5-9(13(18)19-10)14-11(16)7-3-1-2-4-8(7)12(14)17/h1-4,9H,5-6H2

Upstream product

• 85-44-9 phthalic anhydride 
• 56-86-0 L-glutamic acid 
• 3227-01-8 N-(2-Carboxy-benzoyl)-L-glutaminsaeure 
• 108-24-7 acetic anhydride 
• 6349-98-0 N-phthalylglutamic acid 
• 6893-26-1 D-Glutamic acid 
• 22911-88-2 (R)-2-phthalimidoglutaric acid 
• 22509-74-6 N-ethoxycarbonylphthalimide 
• 340-90-9 N-phthaloyl-L-glutamic acid 
• 16450-41-2 L-glutamic acid diethyl ester 
• 109066-23-1 diethyl N-(2-carboxybenzoyl)-L-glutamate 
• 112655-44-4 diethyl N,N-phtaloyl-L-glutamic acid 

Downstream Products

• 52604-94-1 N-(2,6-dioxo-1-phenyl-piperidin-3-yl)-phthalimide 
• 102952-10-3 S-benzyl-N-(N,N-phthaloyl-γ-glutamyl)-penicillamine 
• 117876-52-5 N-[S-benzyl-N-(N,N-phthaloyl-γ-glutamyl)-penicillaminyl]-glycin-ethyl ester 
• 84139-30-0 N⁵-(4-carboxy-phenyl)-N²,N²-phthaloyl-glutamine 
• 124751-43-5 N⁵-(2-hydroxy-ethyl)-DL-glutamine 
• 82207-54-3 N,N-phthaloyl-5-thio-DL-glutamic acid S-phenyl ester 
• 51806-96-3 α-(N-γ-DL-Glutamyl)-amino-propionitril 
• 24666-53-3 2-(1-benzyl-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione 
• 88784-33-2 N,N-phthaloyl-DL-glutamic acid-5-benzyl ester 
• 101895-70-9 N,N-phthaloyl-glutamic acid-5-phenyl ester 
• 111499-77-5 N,N-phthaloyl-glutamic acid-5-(4-carboxy-phenyl ester) 
• 7607-72-9 2-phthalimidoglutaramic acid 
• 539-95-7 N-L-γ-glutamyl-β-alanine nitrile 
• 82263-17-0 γ-Thiophenyl N-phthalyl-L-glutamate 

Relevant articles and documents

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 phthalic acylamino-L-glutamic anhydride

The invention discloses a synthesis method of phthalic acylamino-L-glutamic anhydride. The method comprises the following steps: firstly, ensuring that phthalic anhydride and L-glumatic acid react for4 to 8 hours at 80 to 85 DEG C with the existence of an acid-binding agent, and adjusting pH with hydrochloric acid till N-phthaloyl-L-glutamic acid is separated out; secondly, adding acetic anhydride to the N-phthaloyl-L-glutamic acid obtained in the first step, performing reflux reaction, naturally cooling to room temperature, ensuring that white solid is separated out, separating, and drying,so as to obtain the phthalic acylamino-L-glutamic anhydride. The synthesis method is short in route, easy to operate, high in yield, low in pollution, and more environmentally friendly, ensures that the production cost is greatly reduced, and has a good application prospect.

Synthesis of amphiphilic alternating polyesters with oligo(ethylene glycol) side chains and potential use for sustained release drug delivery

Novel amphiphilic alternating polyesters, poly((N-phthaloyl-l-glutamic anhydride)-co-(2-(2-(2-methoxyethoxy)ethoxy)methyl)oxirane) (P(PGA-co-ME 2MO)), were synthesized by alternating copolymerization of PGA and ME2MO. The structures of the synthesized polyesters were characterized by 1H NMR, 13C NMR, FT-IR, and GPC analyses. Because of the presence of oligo(ethylene glycol) (OEG) side chains, the polyesters could self-assemble into thermosensitive micelles. Dynamic light scattering (DLS) showed that these micelles underwent thermoinduced size decrease without intermicellar aggregation. In vitro methyl thiazolyl tetrazolium (MTT) assay demonstrated that the polyesters were biocompatible to Henrietta Lacks (HeLa) cells, rendering their potential for drug delivery applications. Two hydrophobic drugs, rifampin and doxorubicin (DOX), were loaded into the polyester micelles and observed to be released in a zero-order sustained manner. The sustained release could be accelerated in lower pH or in the presence of proteinase K, due to the degradation of the polyester under these conditions. Remarkably, in vitro cell experiments showed that the polyester micelles accomplished fast release of DOX inside cells and higher anticancer efficacy as compared with the free DOX. With enhanced stability during circulation condition and accelerated drug release at the target sites (e.g., low pH or enzyme presence), these novel polyesters with amphiphilic structures are promising to be used in sustained release drug delivery systems.