sucrose octapropanoate, octapropionyl sucrose
3D model (JSmol)
|Appearance||colorless crystalline solid|
|Density||1.185 g/L |
|Melting point||45.4 °C (113.7 °F; 318.5 K)|
|Boiling point||280–290 °C (536–554 °F; 553–563 K) at 0.05 torr |
|less than 0.1 g/L|
|Solubility||ethanol, isopropanol, toluene, acetone|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Sucrose octapropionate is a chemical compound with formula C
19 or (C
3), an eight-fold ester of sucrose and propionic acid. Its molecule can be described as that of sucrose C
11 with its eight hydroxyl groups HO– replaced by propionate groups H
2–. It is a crystalline colorless solid. It is also called sucrose octapropanoate or octapropionyl sucrose.
Sucrose octapropionate is only slightly soluble in water (less than 0.1 g/L) but is soluble in many common organic solvents such as isopropanol and ethanol, from which it can be crystallized by evaporation of the solvent.
Distillation of fully esterified propionates has been proposed as a method for the separation and identification of sugars.
While the crystallinity of the pure compound prevents its use as a plasticizer it was found that incompletely esterified variants (with 1 to 2 remaining hydroxyls per molecule) will not crystallize, and therefore can be considered for that application.
- Cox, Gerald J.; Ferguson, John H.; Dodds, Mary L. (1933). "III. Technology of Sucrose Octaauml;cetate and Homologous Esters". Industrial & Engineering Chemistry. 25 (9): 968–970. doi:10.1021/ie50285a006.
- Hurd, Charles D.; Liggett, R. W. (1941). "Analytical Separation of Sugars by Distillation of their Propionates". Journal of the American Chemical Society. 63 (10): 2659–2662. doi:10.1021/ja01855a041.
- Hurd, Charles D.; Gordon, K. M. (1941). "Propionyl Derivatives of Sugars". Journal of the American Chemical Society. 63 (10): 2657–2659. doi:10.1021/ja01855a040.
- Hurd, Charles D.; Liggett, R. W.; Gordon, K. M. (1941). "Distillation of Sugar Propionates at Low Pressures". Journal of the American Chemical Society. 63 (10): 2656–2657. doi:10.1021/ja01855a039.
- George P Touey and Herman E Davis (1962) "Non-crystallizing sucrose lower fatty acid esters and compositions thereof" U.S. Patent 3,057,743.