Sucrose octaacetate
[CAS# 126-14-7]

Identification

• Classification: Biochemical >> Carbohydrate >> Double sugar
• Name: Sucrose octaacetate
• Synonyms: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2S,3S,4R,5R)-3,4-diacetyloxy-2,5-bis(acetyloxymethyl)oxolan-2-yl]oxyoxan-2-yl]methyl acetate
• Molecular Formula: C₂₈H₃₈O₁₉
• Molecular Weight: 678.60
• CAS Registry Number: 126-14-7
• EC Number: 204-772-1
• FEMA: 3038
• SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@]2([C@H]([C@@H]([C@H](O2)COC(=O)C)OC(=O)C)OC(=O)C)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C

Properties

• Density: 1.4±0.1 g/cm³ Calc.^*
• Melting point: 82 - 85 ºC (Expl.)
• Boiling point: 668.3±55.0 ºC 760 mmHg (Calc.)^*, 260 ºC (Expl.)
• Flash point: 275.0±31.5 ºC (Calc.)^*
• Solubility: water: slightly soluble (Expl.)
• Index of refraction: 1.509 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338

Discovory and Applicatios

Sucrose octaacetate is a fully acetylated derivative of sucrose in which all eight hydroxyl groups of the parent disaccharide are esterified with acetic acid residues. Its molecular formula is C₂₈H₃₈O₁₉. The compound is typically obtained as a white, crystalline solid and is notable for its intense bitter taste, in contrast to the sweetness of sucrose. The preparation and study of sucrose esters, including sucrose octaacetate, emerged from 19th-century investigations into carbohydrate chemistry, when systematic methods for acetylating polyhydroxy compounds were developed.

The acetylation of sucrose became feasible after chemists established reliable procedures for converting alcohol groups to acetate esters using acetic anhydride in the presence of suitable catalysts. Through controlled reaction conditions, it was shown that all eight hydroxyl groups in sucrose could be substituted, yielding the octaacetate derivative. Analytical methods such as elemental analysis and later spectroscopic techniques confirmed the degree of substitution and the preservation of the glycosidic linkage during acetylation. These studies contributed to the broader understanding of carbohydrate structure and reactivity, helping to clarify the arrangement of hydroxyl groups in sucrose.

One of the most distinctive properties of sucrose octaacetate is its strong bitterness, which was documented in early sensory evaluations. Unlike sucrose, which activates sweet taste receptors, the acetylated derivative interacts differently with taste perception mechanisms. The pronounced bitterness led to its practical use as a denaturant and deterrent. In the 20th century, sucrose octaacetate was incorporated into formulations intended to discourage ingestion of hazardous products. Its effectiveness as a bittering agent was established through controlled testing, demonstrating that very small quantities can impart an aversive taste.

Sucrose octaacetate has been used as a denaturant for industrial alcohol. By adding a strongly bitter but low-toxicity substance, manufacturers can render ethanol unsuitable for beverage use while maintaining its utility for industrial and laboratory applications. Regulatory authorities have approved specific denaturing formulations containing sucrose octaacetate based on toxicological evaluations and sensory thresholds. The compound’s stability and low volatility make it suitable for this purpose, as it remains in the alcohol without significantly affecting physical properties other than taste.

In addition to its role in alcohol denaturation, sucrose octaacetate has been employed as an additive in certain consumer and industrial products to prevent accidental ingestion. Its high bitterness index allows it to function effectively at low concentrations. Toxicological assessments have examined its safety profile, including studies of acute and subchronic exposure, supporting its controlled use in defined applications. These evaluations are based on documented experimental data regarding metabolism and excretion.

From a chemical perspective, sucrose octaacetate illustrates the profound effect of esterification on the properties of carbohydrates. The conversion of hydroxyl groups to acetate esters reduces hydrogen bonding capacity and significantly alters solubility characteristics. While sucrose is highly soluble in water, sucrose octaacetate is far less soluble in aqueous media and more compatible with organic solvents. These differences have been characterized through solubility measurements and crystallographic studies, which show that the acetylated molecule adopts conformations consistent with its esterified structure.

Sucrose octaacetate has also served as a model compound in research on taste perception and structure-taste relationships. By comparing the sensory properties of sucrose and its derivatives, investigators have gained insight into how molecular modifications influence receptor interactions. Such studies rely on established sensory science methodologies and controlled experimental designs.

The discovery and systematic modification of sucrose to form sucrose octaacetate reflect the maturation of carbohydrate chemistry and applied sensory science. Its preparation through complete acetylation, the confirmation of its structure, and the documentation of its intense bitterness have supported practical uses in denatured alcohol and deterrent formulations. The compound remains a well-characterized example of how chemical transformation of a naturally occurring sugar can produce markedly different physical and sensory properties while retaining a defined molecular framework.

References

2024. Towards an EPR on a Chip Spectrometer for Monitoring Radiation Damage During X-ray Absorption Spectroscopy. Applied Magnetic Resonance.
DOI: 10.1007/s00723-024-01702-7