5469-75-0

Usage

Uses

Used in Pharmaceutical Industry:
2,3,4,5-tetraacetyloxyhexanedioic acid is used as a reagent for the production of pharmaceuticals, as it serves as a building block in organic synthesis.
Used in Dye Industry:
2,3,4,5-tetraacetyloxyhexanedioic acid is used as a reagent for the production of dyes, contributing to the synthesis of various dye compounds.
Used in Organic Compounds Production:
2,3,4,5-tetraacetyloxyhexanedioic acid is used as a reagent for the production of other organic compounds, given its role as a building block in organic synthesis.
Used in Antimicrobial and Antifungal Applications:
2,3,4,5-tetraacetyloxyhexanedioic acid has been studied for its potential antimicrobial and antifungal properties, indicating its use in applications requiring such characteristics.
Note: The potential toxicity and environmental persistence of 2,3,4,5-tetraacetyloxyhexanedioic acid necessitate careful handling and disposal to mitigate any adverse effects.

InChI:InChI=1/C26H25NO3/c1-26(2,3)16-10-12-17(13-11-16)30-25-21(27(4)5)15-14-20-22(25)24(29)19-9-7-6-8-18(19)23(20)28/h6-15H,1-5H3

Upstream product

• 526-99-8 meso-galactaric acid 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 87-73-0 DL-altraric acid 
• 7664-93-9 sulfuric acid 
• 113973-61-8 1,2,3,6-tetra-O-acetyl-muco-inositol 
• 109526-05-8 conduritol A tetraacetate 
• 98221-46-6 tetra-O-acetylmucic dialdehyde 

Downstream Products

• 526-99-8 meso-galactaric acid 
• 20939-15-5 3-methyl-4-amino-5-mercapto-1,2,4-triazole 
• 24808-45-5 dimethyl galactarate 
• 79-20-9 acetic acid methyl ester 
• 5160-18-9 tetra-O-acetyl-galactaric acid dianilide 
• 15410-54-5 2,3,4,5-Tetra-O-acetyl-1,6-di-O-methansulfonylgalactit 
• 100977-53-5 Schleimsaeure-bis-<4-aminosulfonyl-anilid> 
• 106822-41-7 Tetraacetyl-schleimsaeure-bis-<4-aminosulfonyl-anilid> 
• 99786-16-0 Galactonsaeure-dianilid 
• 5160-18-9 Tetra-O-acetyl-galactonsaeure-dianilid 
• 496-64-0 3-hydroxy-2-pyrone 

Relevant academic research and scientific papers

Neoglycolipids for Prolonging the Effects of Peptides: Self-Assembling Glucagon-like Peptide 1 Analogues with Albumin Binding Properties and Potent in Vivo Efficacy

Novel principles for optimizing the properties of peptide-based drugs are needed in order to leverage their full pharmacological potential. We present the design, synthesis, and evaluation of a library of neoglycolipidated glucagon-like peptide 1 (GLP-1) analogues, which are valuable drug candidates for treatment of type 2 diabetes and obesity. Neoglycolipidation of GLP-1 balanced the lipophilicity, directed formation of soluble oligomers, and mediated albumin binding. Moreover, neoglycolipidation did not compromise bioactivity, as in vitro potency of neoglycolipidated GLP-1 analogues was maintained or even improved compared to native GLP-1. This translated into pronounced in vivo efficacy in terms of both decreased acute food intake and improved glucose homeostasis in mice. Thus, we propose neoglycolipidation as a novel, general method for modulating the properties of therapeutic peptides.

Pyrone Synthesis from Renewable Sources: Easy Preparation of 3-Acetoxy-2-oxo-2H-pyran-6-carboxylic Salts and their Derivatives as 3-Hydroxy-2H-pyran-2-one from C6 Aldaric Acids

2-Pyrones are compounds present in several natural products and represent interesting building blocks for the preparation of intermediates in organic syntheses. For these reasons, many different preparation protocols have been developed for the synthesis of pyrone moieties. In this work, a green approach toward the synthesis of those compounds starting from C6 aldaric acids has been investigated. These products are an interesting and versatile class of poly functional C6 units coming from renewable sources. In this paper, we report a green procedure based on a reaction with acetic anhydride under different pH conditions to convert mucic acid and glucaric acid salts into the 3-acetoxy-2-oxo-2H-pyran-6-carboxylic acid salts and their derivatives. The salts, in the presence of hydrochloric acid, are quantitatively converted into the corresponding 3-hydroxy-2-oxo-2H-pyran-6-carboxylic acid, which afforded 3-hydroxy-2H-pyran-2-one in very high yield by further thermal decarboxylation. Crystal structure of the five membered ring lactone intermediate is reported.

Synthesis and characterization of copolyanhydrides of carbohydrate-based galactaric acid and adipic acid

A series of copolyanhydrides, consisting of 2,3,4,5-tetra-O-acetylgalactaric acid (AGA) and adipic acid (AA) as monomer units, was polymerized. Synthesis of AGA monomer consisted of two steps. First, O-acetylation of galactaric acid secondary hydroxyl groups was performed using acetic anhydride as a reagent. Acetic anhydride was then further used as a reagent in the synthesis of diacetyl mixed anhydride of AGA. Polymerizations were conducted as bulk condensation polymerization at 150 °C. Thermal properties of the copolymers varied depending on monomer composition. Increase in the AGA content had a clear increasing effect on the Tg. A similar increasing effect was observed in Tm. The degree of crystallinity decreased as AGA content increased. There was a slightly lowering tendency in the molecular weights of the obtained polymers when the AGA content in the polymerization mixtures increased. The described synthesis route shows that bio-based aldaric acid monomers are potential candidates for the adjustment of thermal properties of polyanhydrides.

Synthesis and characterization of copolyanhydrides of carbohydrate-based galactaric acid and adipic acid

A series of copolyanhydrides, consisting of 2,3,4,5-tetra-O-acetylgalactaric acid (AGA) and adipic acid (AA) as monomer units, was polymerized. Synthesis of AGA monomer consisted of two steps. First, O-acetylation of galactaric acid secondary hydroxyl groups was performed using acetic anhydride as a reagent. Acetic anhydride was then further used as a reagent in the synthesis of diacetyl mixed anhydride of AGA. Polymerizations were conducted as bulk condensation polymerization at 150 °C. Thermal properties of the copolymers varied depending on monomer composition. Increase in the AGA content had a clear increasing effect on the Tg. A similar increasing effect was observed in Tm. The degree of crystallinity decreased as AGA content increased. There was a slightly lowering tendency in the molecular weights of the obtained polymers when the AGA content in the polymerization mixtures increased. The described synthesis route shows that bio-based aldaric acid monomers are potential candidates for the adjustment of thermal properties of polyanhydrides.