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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 | |
PubChem
CID
|
|
| |
| |
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
36H
54O
19 or (C
3H
5O
2)
8(C
12H
14O
3), an eight-fold
ester of
sucrose and
propionic acid. Its
molecule can be described as that of sucrose C
12H
22O
11 with its eight
hydroxyl groups HO– replaced by
propionate groups H
3C–CH
2–CO
2–. It is a
crystalline colorless solid.
[1] It is also called sucrose octapropanoate or octapropionyl sucrose.
The preparation of sucrose octapropionate was first described in 1933 by Gerald J. Cox and others. [1]
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]
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]
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]
![]() | |
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 | |
PubChem
CID
|
|
| |
| |
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
36H
54O
19 or (C
3H
5O
2)
8(C
12H
14O
3), an eight-fold
ester of
sucrose and
propionic acid. Its
molecule can be described as that of sucrose C
12H
22O
11 with its eight
hydroxyl groups HO– replaced by
propionate groups H
3C–CH
2–CO
2–. It is a
crystalline colorless solid.
[1] It is also called sucrose octapropanoate or octapropionyl sucrose.
The preparation of sucrose octapropionate was first described in 1933 by Gerald J. Cox and others. [1]
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]
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]
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]