Sucrose octapropionate is a chemical compound with formula or , an eight-fold ester of

sucrose Sucrose, a disaccharide, is a sugar composed of glucose and fructose subunits. It is produced naturally in plants and is the main constituent of white sugar. It has the molecular formula . For human consumption, sucrose is extracted and refined ...

and

propionic acid Propionic acid (, from the Greek words πρῶτος : ''prōtos'', meaning "first", and πίων : ''píōn'', meaning "fat"; also known as propanoic acid) is a naturally occurring carboxylic acid with chemical formula CH3CH2CO2H. It is a liq ...

. Its molecule can be described as that of sucrose with its eight hydroxyl groups – replaced by propionate groups –. It is a crystalline colorless solid. It is also called sucrose octapropanoate or octapropionyl sucrose.

History

The preparation of sucrose octapropionate was first described in 1933 by Gerald J. Cox and others.

Preparation

The compound can be prepared by the reaction of sucrose with propionic anhydride in the melt state or at room temperature, over several days, in anhydrous pyridine.

Properties

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 Isopropyl alcohol (IUPAC name propan-2-ol and also called isopropanol or 2-propanol) is a colorless, flammable organic compound with a pungent alcoholic odor. As an isopropyl group linked to a hydroxyl group (chemical formula ) it is the simple ...

and ethanol, from which it can be crystallized by evaporation of the solvent. The crystalline form melts at 45.4–45.5 °C into a viscous liquid (47.8

poise Poise may mean: * Poise (unit), a measure of viscosity * A concept similar to gracefulness * Ferdinand Poise image:Ferdinand Poise 1892.jpg, Jean Alexandre Ferdinand Poise (3 June 1828 – 13 May 1892) was a French composer, mainly of opéra ...

s at 48.9 °C), that becomes a clear glassy solid on cooling, but easily recrystallizes. The density of the glassy form is 1.185 kg/ L (at 20 °C). It is an

optically active Optical rotation, also known as polarization rotation or circular birefringence, is the rotation of the orientation of the plane of polarization about the optical axis of linearly polarized light as it travels through certain materials. Circul ...

compound with �sup>20_D +53°. The compound can be vacuum distilled at 280–290 °C and 0.05 to 0.07 torr.

Applications

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.

References

{{reflist, refs= {{cite journal, doi=10.1021/ie50285a006, title=III. Technology of Sucrose Octaauml;cetate and Homologous Esters, year=1933, last1=Cox, first1=Gerald J., last2=Ferguson, first2=John H., last3=Dodds, first3=Mary L., journal=Industrial & Engineering Chemistry, volume=25, issue=9, pages=968–970 {{cite journal, doi=10.1021/ja01855a040, title=Propionyl Derivatives of Sugars, year=1941, last1=Hurd, first1=Charles D., last2=Gordon, first2=K. M., journal=Journal of the American Chemical Society, volume=63, issue=10, pages=2657–2659 {{cite journal, doi=10.1021/ja01855a039, title=Distillation of Sugar Propionates at Low Pressures, year=1941, last1=Hurd, first1=Charles D., last2=Liggett, first2=R. W., last3=Gordon, first3=K. M., journal=Journal of the American Chemical Society, volume=63, issue=10, pages=2656–2657 {{cite journal, doi=10.1021/ja01855a041, title=Analytical Separation of Sugars by Distillation of their Propionates, year=1941, last1=Hurd, first1=Charles D., last2=Liggett, first2=R. W., journal=Journal of the American Chemical Society, volume=63, issue=10, pages=2659–2662 George P Touey and Herman E Davis (1962) "Non-crystallizing sucrose lower fatty acid esters and compositions thereof" {{US Patent, 3057743. Disaccharides Bitter compounds propionate esters

History

Preparation

Properties

Applications

See also

References