Phthaloyl-L-glutamic acid anhydride
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Phthaloyl-L-glutamic acid anhydride

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Category
Cyclic Amino Acids
Catalog number
BAT-003455
CAS number
25830-77-7
Molecular Formula
C13H9NO5
Molecular Weight
259.30
Phthaloyl-L-glutamic acid anhydride
IUPAC Name
2-[(3S)-2,6-dioxooxan-3-yl]isoindole-1,3-dione
Synonyms
Pht-L-Glu-anhydride; (S)-2-(2,6-Dioxotetrahydro-2H-Pyran-3-Yl)Isoindoline-1,3-Dione
Appearance
Off-white solid
Purity
≥ 99%
Density
1.554 g/cm3
Melting Point
202-208 °C
Boiling Point
484.8°C
Storage
Store at 2-8 °C
InChI
InChI=1S/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-/m0/s1
InChI Key
ICDLEMPZXFCQEB-VIFPVBQESA-N
Canonical SMILES
C1CC(=O)OC(=O)C1N2C(=O)C3=CC=CC=C3C2=O
1. Castor Oil-Based Biodegradable Polyesters
Konda Reddy Kunduru, Arijit Basu, Moran Haim Zada, Abraham J Domb Biomacromolecules. 2015 Sep 14;16(9):2572-87. doi: 10.1021/acs.biomac.5b00923. Epub 2015 Sep 2.
This Review compiles the synthesis, physical properties, and biomedical applications for the polyesters based on castor oil and ricinoleic acid. Castor oil has been known for its medicinal value since ancient times. It contains ~90% ricinoleic acid, which enables direct chemical transformation into polyesters without interference of other fatty acids. The presence of ricinoleic acid (hydroxyl containing fatty acid) enables synthesis of various polyester/anhydrides. In addition, castor oil contains a cis-double bond that can be hydrogenated, oxidized, halogenated, and polymerized. Castor oil is obtained pure in large quantities from natural sources; it is safe and biocompatible.
2. Polyanhydride Chemistry
Pulikanti Guruprasad Reddy, Abraham J Domb Biomacromolecules. 2022 Dec 12;23(12):4959-4984. doi: 10.1021/acs.biomac.2c01180. Epub 2022 Nov 23.
Polyanhydrides (PAs) are a class of synthetic biodegradable polymers employed as controlled drug delivery vehicles. They can be synthesized and scaled up from low-cost starting materials. The structure of PAs can be manipulated synthetically to meet desirable characteristics. PAs are biocompatible, biodegradable, and generate nontoxic metabolites upon degradation, which are easily eliminated from the body. The rate of water penetrating into the polyanhydride (PA) matrix is slower than the anhydride bond cleavage. This phenomenon sets PAs as "surface-eroding drug delivery carriers." Consequently, a variety of PA-based drug delivery carriers in the form of solid implants, pasty injectable formulations, microspheres, nanoparticles, etc. have been developed for the sustained release of small molecule drugs, and vaccines, peptide drugs, and nucleic acid-based active agents. The rate of drug delivery is often controlled by the polymer erosion rate, which is influenced by the polymer structure and composition, crystallinity, hydrophobicity, pH of the release medium, device size, configuration, etc. Owing to the above-mentioned interesting physicochemical and mechanical properties of PAs, the present review focuses on the advancements made in the domain of synthetic biodegradable biomedical PAs for therapeutic delivery applications. Various classes of PAs, their structures, their unique characteristics, their physicochemical and mechanical properties, and factors influencing surface erosion are discussed in detail. The review also summarizes various methods involved in the synthesis of PAs and their utility in the biomedical domain as drug, vaccine, and peptide delivery carriers in different formulations are reviewed.
3. Safety Assessment of Trimellitic Anhydride Copolymers as Used in Cosmetics
Monice M Fiume, et al. Int J Toxicol. 2020 Nov/Dec;39(3_suppl):74S-92S. doi: 10.1177/1091581820958690.
The Expert Panel for Cosmetic Ingredient Safety (Panel) assessed the safety of 6 trimellitic anhydride copolymers as used in cosmetics. These ingredients are related as copolymers in that they all share trimellitic anhydride (ie, 1,2,4-benzenetricarboxylic acid anhydride) as a monomer, are reported to function as film formers in cosmetics, and are reported to be primarily used in nail products. Very limited safety data were available or submitted. The Panel concluded that Adipic Acid/Neopentyl Glycol/Trimellitic Anhydride Copolymer and Phthalic Anhydride/Trimellitic Anhydride/Glycols Copolymer are safe in nail product formulations in the present practices of use and concentration, but the data are insufficient to make a determination of safety on the use of these 2 ingredients in all other types of cosmetic formulations. The Panel also concluded that the available data are insufficient to make a determination that the remaining trimellitic anhydride copolymers are safe for use in cosmetic formulations.
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