3343-28-0

Basic information

• Product Name: N-PHTHALOYL-DL-GLUTAMIC ANHYDRIDE 98
• Synonyms: 2-(tetrahydro-2,6-dioxo-2h-pyran-3-yl)-1h-isoindole-3(2h)-dione;2-(Tetrahydro-2,6-dioxopyran-3-yl)isoin-dole-1,3(2H)-dione;N-(tetrahydro-2,6-dioxo-2H-pyran-3-yl)phthalimide;2-Phthalimidoglutaric Anhydride;2-(Tetrahydro-2,6-dioxo-2H-pyran-3-yl)-1H-isoindole-1,3(2H)-dione;4,5-Dihydro-3-(phthalimidyl)-2H-pyran-2,6(3H)-dione;N-(2,6-Dioxotetrahydro-2H-pyran-3-yl)phthalimide;2-(2,6-dioxo-tetrahydro-2H-pyran-3-yl)isoindoline-1,3-dione
• CAS NO: 3343-28-0
• Molecular Formula: C₁₃H₉NO₅
• Molecular Weight: 259.21426
• EINECS: 222-088-1
• Product Categories: N-Substituted Maleimides, Succinimides & Phthalimides;N-Substituted Phthalimides;Anhydride Monomers;Monomers;Polymer Science
• Mol File: 3343-28-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: 197-201 °C(lit.)
• Boiling Point: 402.47°C (rough estimate)
• Flash Point: 247°C
• Appearance: /
• Density: 1.3394 (rough estimate)
• Vapor Pressure: 1.48E-09mmHg at 25°C
• Refractive Index: 1.5880 (estimate)
• Solubility: soluble in Dioxane
• PKA: -2.60±0.20(Predicted)
• CAS DataBase Reference: N-PHTHALOYL-DL-GLUTAMIC ANHYDRIDE 98(CAS DataBase Reference)
• NIST Chemistry Reference: N-PHTHALOYL-DL-GLUTAMIC ANHYDRIDE 98(3343-28-0)
• EPA Substance Registry System: N-PHTHALOYL-DL-GLUTAMIC ANHYDRIDE 98(3343-28-0)

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: 3343-28-0(Hazardous Substances Data)

Usage

Safety Profile

Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx.

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/t9-/m1/s1

Upstream product

• 85-44-9 phthalic anhydride 
• 56-86-0 L-glutamic acid 
• 108-24-7 acetic anhydride 
• 6349-98-0 N-phthalylglutamic acid 
• 3227-01-8 N-(2-Carboxy-benzoyl)-L-glutaminsaeure 

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 
• 52604-91-8 N⁵-phenyl-N²,N²-phthaloyl-glutamine 
• 50-35-1 thalidomide 
• 51806-96-3 α-(N-γ-DL-Glutamyl)-amino-propionitril 
• 102003-30-5 N⁵-methyl-N⁵-phenyl-N²,N²-phthaloyl-glutamine 
• 24666-53-3 2-(1-benzyl-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione 
• 94547-37-2 N⁵-benzyl-N²,N²-phthaloyl-glutamine 
• 88784-33-2 N,N-phthaloyl-DL-glutamic acid-5-benzyl ester 
• 101895-70-9 N,N-phthaloyl-glutamic acid-5-phenyl ester 

Relevant articles and documents

A novel strategy for efficient chemoenzymatic synthesis of D-glutamine using recombinant Escherichia coli cells

D-glutamine is a D type stereoisomer of glutamine which is involved in many metabolic processes. Seeking lower-cost and industrially scalable approaches for the synthesis of D-glutamine is very valuable both in academic career and potential applications. Herein, we developed a novel efficient chemoenzymatic strategy for producing D-glutamine. Initially, DL-glutamine was chemically prepared with cheap and accessible DL-glutamic acid as raw material. Subsequently, the L-glutamine among the racemic mixture was selectively hydrolyzed to L-glutamic acid by Escherichia coli whole-cell system which expressed L-aminopeptidase D-Ala-esterase/amidase (DmpA) from Ochrobactrum anthropi. The left D-glutamine was obtained by isoelectric point precipitation with 70% of the theoretical yield. Furthermore, we optimized enzymatic resolution conditions to determine the optimum parameters as pH 8, 30 °C, 0.1% (v/v) Triton X-100, and 1 mM Mn2+. These results suggested that our strategy might be potentially usable for the synthesis of D-glutamine in industrial productions.

Thalidomide metabolites and analogues. 3. Synthesis and antiangiogenic activity of the teratogenic and TNFα-modulatory thalidomide analogue 2-(2,6-dioxopiperidine-3-yl)phthalimidine

Versatile synthesis of the teratogenic, TNFα-modulatory, and antiangiogenic thalidomide analogue 2-(2,6-dioxopiperidine-3-yl)phthalimidine (1) and its direct antiangiogenic properties are described. With thalidomide or thalidomide derivatives as precursors, the synthesis involved either carbonyl reduction/thiation-desulfurization or carbonyl reduction/acyliminium ion reduction protocols. Compared to earlier studies with thalidomide, which was only active with microsomal treatment, 1 exhibited marginal inhibitory activity in the rat aortic ring assay, thereby demonstrating the requirement for metabolic activation.

Reaction of cyclic acid anhydrides with ethyl cyanoacetate.

-