5469-75-0

Basic information

• Product Name: 2,3,4,5-tetraacetyloxyhexanedioic acid
• Synonyms: 2,3,4,5-tetraacetyloxyhexanedioic acid
• CAS NO: 5469-75-0
• Molecular Formula: C₁₄H₁₈O₁₂
• Molecular Weight: 378.29
• Mol File: 5469-75-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 567.8°Cat760mmHg
• Flash Point: 205.1°C
• Appearance: /
• Density: 1.431g/cm³
• Vapor Pressure: 1.56E-12mmHg at 25°C
• Refractive Index: 1.622
• CAS DataBase Reference: 2,3,4,5-tetraacetyloxyhexanedioic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,5-tetraacetyloxyhexanedioic acid(5469-75-0)
• EPA Substance Registry System: 2,3,4,5-tetraacetyloxyhexanedioic acid(5469-75-0)

Safety Data

• Hazardous Substances Data: 5469-75-0(Hazardous Substances Data)

Usage

General Description

2,3,4,5-tetraacetyloxyhexanedioic acid, also known as acetylacetone, is a synthetic compound with the molecular formula C10H14O8. It is an acetoacetic acid derivative that is often used as a building block in organic synthesis. This chemical is a white crystalline solid that is soluble in many organic solvents and has a variety of industrial applications. It is commonly used as a reagent in the production of pharmaceuticals, dyes, and other organic compounds. Additionally, it has been studied for its potential antimicrobial and antifungal properties. However, due to its potential toxicity and environmental persistence, it is important to handle and dispose of 2,3,4,5-tetraacetyloxyhexanedioic acid with care.

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 
• 113973-61-8 1,2,3,6-tetra-O-acetyl-muco-inositol 
• 109526-05-8 conduritol A tetraacetate 
• 87-73-0 DL-altraric acid 
• 7664-93-9 sulfuric acid 
• 75-36-5 acetyl chloride 
• 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 
• 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 
• 24808-45-5 dimethyl galactarate 
• 79-20-9 acetic acid methyl ester 

Relevant articles and documents

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.