7208-40-4

Basic information

• Product Name: [(2S,3R)-2,3,4-triacetyloxybutyl] acetate
• Synonyms: [(2S,3R)-2,3,4-triacetyloxybutyl] acetate;(2R,3S)-1,2,3,4-Butanetetrol tetraacetate
• CAS NO: 7208-40-4
• Molecular Formula: C₁₂H₁₈O₈
• Molecular Weight: 0
• Mol File: 7208-40-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 321.6°C at 760 mmHg
• Flash Point: 136.5°C
• Appearance: /
• Density: 1.202g/cm³
• Vapor Pressure: 0.000296mmHg at 25°C
• Refractive Index: 1.448
• CAS DataBase Reference: [(2S,3R)-2,3,4-triacetyloxybutyl] acetate(CAS DataBase Reference)
• NIST Chemistry Reference: [(2S,3R)-2,3,4-triacetyloxybutyl] acetate(7208-40-4)
• EPA Substance Registry System: [(2S,3R)-2,3,4-triacetyloxybutyl] acetate(7208-40-4)

Safety Data

• Hazardous Substances Data: 7208-40-4(Hazardous Substances Data)

Usage

Description

[(2S,3R)-2,3,4-triacetyloxybutyl] acetate is a chemical compound with the molecular formula C11H16O7, derived from butyl acetate with a 2,3,4-triacetyloxy substituent. It features two chiral centers and exists as a pair of enantiomers. [(2S,3R)-2,3,4-triacetyloxybutyl] acetate is known for its stability under normal conditions and has a broad spectrum of applications across different industries.

Uses

Used in Organic Synthesis:
[(2S,3R)-2,3,4-triacetyloxybutyl] acetate is used as a reagent in the field of organic synthesis, particularly for the acetylation of alcohols and phenols. Its acetyl groups contribute to its stability and make it a valuable component in creating a variety of chemical products.
Used in the Food Industry:
In the food industry, [(2S,3R)-2,3,4-triacetyloxybutyl] acetate is utilized as a flavoring agent. Its unique properties allow it to enhance the taste and aroma of various food products, contributing to a more enjoyable consumer experience.
Used in Perfumes and Cosmetics:
[(2S,3R)-2,3,4-triacetyloxybutyl] acetate also finds application in the perfumery and cosmetics industry as a fragrance. Its ability to provide a pleasant scent makes it a desirable additive in the creation of perfumes, colognes, and other scented products.
Used in Pharmaceutical Applications:
Although not explicitly mentioned in the provided materials, due to its chemical structure and reactivity, [(2S,3R)-2,3,4-triacetyloxybutyl] acetate could potentially be used in the development of new pharmaceutical compounds, taking advantage of its acetylation properties for drug modification or synthesis.

InChI:InChI=1/C12H18O8/c1-7(13)17-5-11(19-9(3)15)12(20-10(4)16)6-18-8(2)14/h11-12H,5-6H2,1-4H3/t11-,12+

Upstream product

• 64-19-7 acetic acid 
• 141-46-8 Glycolaldehyde 
• 2319-57-5 1,2,3,4-butanetetrol 
• 108-24-7 acetic anhydride 
• 2418-52-2 D-threitol 
• 909878-64-4 meso-erythritol 
• 100-39-0 benzyl bromide 
• 96-26-4 dihydroxyacetone 
• 56-82-6 Glyceraldehyde 
• 6968-16-7 rac-threitol 

Relevant articles and documents

Asymmetric organocatalytic formation of protected and unprotected tetroses under potentially prebiotic conditions

Esters of proteinogenic amino acids efficiently catalyse the formation of erythrose and threose under potentially prebiotic conditions in the highest yields and enantioselectivities yet reported. Remarkably while esters of (l)-proline yield (l)-tetroses, esters of (l)-leucine, (l)-alanine and (l)-valine generate (d)-tetroses, offering the potential to account for the link between natural (l)-amino acids and natural (d)-sugars. The effect of pH and NaCl on the yields and enantioselectivities was also investigated and was shown to be significant, with the optimal enantioselectivities occurring at pH 7.

Prebiotic carbohydrate synthesis: Zinc-proline catalyzes direct aqueous aldol reactions of α-hydroxy aldehydes and ketones

Zn-proline catalyzed aldolisation of glycoladehyde gave mainly tetroses whereas in the cross-aldolisation of glycoladehyde and rac-glyceraldehyde, pentoses accounted for 60% of the sugars formed with 20% of ribose. The Royal Society of Chemistry 2005.

EQUILIBRATION OF ALDITOL ANHYDRIDES IN ACETIC ACID

Dehydration of pentitols in acetic acid containing an acidic catalyst parallels that in aqueous sulfuric acid; 1,4(2,5)-dehydration occurs with inversion of configuration at C-2 or C-4.Acetylated alditols undergo similar processes via intermediates having free hydroxyl groups.Configurational inversion of 1,4- or 1,5-anhydroalditols is attributed to intermediate acyloxonium ions that are also proposed as intermediates in the structural isomerisation.Drastic treatment of each alditol gives equilibrium mixtures.The equilibrium concentrations are used to calculate free-energy differences.