Sucrose octapropionate

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Sucrose octapropionate
Sucrose octapropionate.png
Names
IUPAC name
1,3,4,6-Tetra-O-propionyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-propionyl-α-D-glucopyranoside
Other names
sucrose octapropanoate, octapropionyl sucrose
Identifiers
3D model (JSmol)
ChemSpider
  • Key: PGIIRNKNDYWWSN-ZRCJJVNESA-N
  • InChI=1S/C36H54O19/c1-9-22(37)45-17-20-30(49-25(40)12-4)32(51-27(42)14-6)33(52-28(43)15-7)35(48-20)55-36(19-47-24(39)11-3)34(53-29(44)16-8)31(50-26(41)13-5)21(54-36)18-46-23(38)10-2/h20-21,30-35H,9-19H2,1-8H3/t20-,21-,30-,31-,32+,33-,34+,35-,36+/m1/s1
  • O=C(O[C@H]1[C@H](O[C@H](COC(=O)CC)[C@@H](OC(=O)CC)[C@@H]1OC(=O)CC)O[C@@]2(O[C@@H]([C@@H](OC(=O)CC)[C@@H]2OC(=O)CC)COC(=O)CC)COC(=O)CC)CC
Properties
C36H54O19
Appearance colorless crystalline solid
Density 1.185 g/L [1]
Melting point 45.4 °C (113.7 °F; 318.5 K)[1]
Boiling point 280–290 °C (536–554 °F; 553–563 K) at 0.05 torr [2]
less than 0.1 g/L
Solubility ethanol, isopropanol, toluene, acetone[1]
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
36
H
54
O
19
or (C
3
H
5
O
2
)
8
(C
12
H
14
O
3
)
, an eight-fold ester of sucrose and propionic acid. Its molecule can be described as that of sucrose C
12
H
22
O
11
with its eight hydroxyl groups HO– replaced by propionate groups H
3
C–CH
2
–CO
2
–. It is a crystalline colorless solid.[1] It is also called sucrose octapropanoate or octapropionyl sucrose.

History[edit]

The preparation of sucrose octapropionate was first described in 1933 by Gerald J. Cox and others.[1]

Preparation[edit]

The compound can be prepared by the reaction of sucrose with propionic anhydride in the melt state[1] or at room temperature, over several days, in anhydrous pyridine.[3]

Properties[edit]

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.[3][4]

The crystalline form melts at 45.4–45.5 °C into a viscous liquid (47.8 poises at 48.9 °C), that becomes a clear glassy solid on cooling, but easily recrystallizes.[1][3]

The density of the glassy form is 1.185 kg/L (at 20 °C). It is an optically active compound with [α]20D +53°.[3]

The compound can be vacuum distilled at 280–290 °C and 0.05 to 0.07 torr.[2]

Applications[edit]

Distillation of fully esterified propionates has been proposed as a method for the separation and identification of sugars.[2]

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.[5]

See also[edit]

References[edit]

  1. ^ a b c d e f g 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.
  2. ^ a b c 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.
  3. ^ a b c d 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.
  4. ^ 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.
  5. ^ George P Touey and Herman E Davis (1962) "Non-crystallizing sucrose lower fatty acid esters and compositions thereof" U.S. Patent 3,057,743.