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Sucrose octaacetate

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Identification
Molecular formula
C28H38O19
CAS number
126-14-7
IUPAC name
[(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-[(2S,3S,4R,5R)-3,4-diacetoxy-2,5-bis(acetoxymethyl)tetrahydrofuran-2-yl]oxy-tetrahydropyran-2-yl]methyl acetate
State
State

At room temperature, sucrose octaacetate is typically in a solid state, specifically as a crystalline powder.

Melting point (Celsius)
86.00
Melting point (Kelvin)
359.15
Boiling point (Celsius)
300.00
Boiling point (Kelvin)
573.15
General information
Molecular weight
678.62g/mol
Molar mass
678.6220g/mol
Density
1.2800g/cm3
Appearence

Sucrose octaacetate is a white, crystalline powder with an intensely bitter taste. Due to its strong bitterness, it is often used as a denatonium agent to deter ingestion.

Comment on solubility

Solubility Characteristics

The compound [(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-[(2S,3S,4R,5R)-3,4-diacetoxy-2,5-bis(acetoxymethyl)tetrahydrofuran-2-yl]oxy-tetrahydropyran-2-yl]methyl acetate exhibits interesting solubility properties that can be summarized as follows:

  • Solvent Affinity: This complex organic compound is thought to show preferential solubility in polar solvents due to the presence of multiple acetoxy groups, which can form hydrogen bonds with water molecules.
  • Water Solubility: The solubility in water is expected to be limited because of the long hydrophobic carbon chains, despite its partially polar characteristics.
  • Organic Solvents: It may be better solubilized in organic solvents such as ethanol and methanol, which can accommodate the hydrophobic and polar regions of the molecule more effectively.
  • Temperature Dependence: Solubility could also be influenced by temperature, typically increasing at higher temperatures for many organic compounds, which might allow for better dissolution rates.
  • Application Insight: Understanding its solubility is crucial for its potential applications in pharmaceuticals or as a chemical reagent, where optimal solvent conditions can significantly affect the outcomes of reactions or the stability of the compound.

In summary, while this compound has potential solubility in certain environments, careful consideration of the solvent environment and conditions is essential for maximizing its utility.

Interesting facts

Interesting Facts about the Compound

This compound, which may appear intricate, is a fascinating example of complex organic molecules composed through multiple functional groups and stereocenters. Specifically, it represents a type of glycoside, which incorporates carbohydrate structures. Below are some intriguing points about this compound:

  • Glycosidic Bonds: The compound contains glycosidic linkages that play a crucial role in biochemistry, particularly in the formation of disaccharides and polysaccharides. These bonds are essential for energy storage and structural functions in living organisms.
  • Stereochemistry: The presence of various stereocenters indicates that this compound can exist in different stereoisomeric forms, which can significantly influence its chemical behavior and interaction with biological systems.
  • Applications: Compounds like this are often researched for their potential use in drug development, especially within the field of natural products, owing to their complex structures and possible biological activity.
  • Reactivity: The acetoxy groups present provide reactive sites that can be leveraged in synthetic chemistry, making this compound valuable for further chemical transformations.
  • Natural Sources: Many compounds with similar structures can be derived from natural sources, such as plants, and are studied for their medicinal properties and potential therapeutic applications.

As noted by renowned chemists, "Understanding the structure leads to a deeper appreciation of function and reactivity." This complex compound exemplifies that principle remarkably well.

Given its multifaceted nature, continued research on such compounds might unveil novel applications in pharmacology and materials science, expanding our knowledge of chemical interactions in both natural and synthetic settings.

Synonyms
SUCROSE OCTAACETATE
126-14-7
Octaacetylsucrose
FEMA No. 3038
sucrose octa-acetate
DTXSID3042423
NSC-1695
07V591057T
DTXCID1022423
[(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
alpha-D-Glucopyranoside, 1,3,4,6-tetra-O-acetyl-beta-D-fructofuranosyl, tetraacetate
sucrose octa acetate
((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
RefChem:186404
GlyTouCan:G43789DD
G43789DD
204-772-1
Octaacetyl sucrose
D-(+)-Sucrose octaacetate
MFCD00006623
Octa-O-acetyl D-(+)-Sucrose
alpha-D-Glucopyranoside, 1,3,4,6-tetra-O-acetyl-beta-D-fructofuranosyl, 2,3,4,6-tetraacetate
Sucrose octaacetate [NF]
D-(+)-Saccharose Octaacetate
(2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(((2S,3S,4R,5R)-3,4-diacetoxy-2,5-bis(acetoxymethyl)tetrahydrofuran-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
NCGC00160615-01
Sucrose octaacetate (NF)
Octa-O-acetylsucrose
a-D-Glucopyranoside,1,3,4,6-tetra-O-acetyl-b-D-fructofuranosyl, 2,3,4,6-tetraacetate
CAS-126-14-7
NSC 1695
EINECS 204-772-1
BRN 0079290
AI3-00071
sucrose-octaacetate
UNII-07V591057T
2,3,4,6,1',3',4',6'-Octa-O-acetylsucrose
1,3,4,6-Tetra-O-acetyl-beta-D-fructofuranosyl-alpha-D-glucopyranoside tetraacetate
SCHEMBL48906
5-17-08-00410 (Beilstein Handbook Reference)
Sucrose octaacetate (Standard)
orb1307719
CHEMBL2105790
SUCROSE OCTAACETATE [MI]
CHEBI:180783
Octa-O-acetyl D-(+)-Saccharose
SUCROSE OCTAACETATE [FHFI]
Sucrose octaacetate, >=97%, FG
D-(+)-Sucrose octaacetate, 98%
Tox21_111938
Tox21_300386
SUCROSE OCTAACETATE [USP-RS]
SUCROSE OCTA-ACETATE [MART.]
AKOS015895274
SUCROSE OCTA-ACETATE [WHO-DD]
Tox21_111938_1
HY-119309R
OS03658
1,3,4,6-Tetra-O-acetyl-beta-D-fructofuranosyl-alpha-D-glucopyrano- side tetraacetate
alpha-D-Glucopyranoside, 1,3,4,6-tetra-O-acetyl-beta-D-fructofuranosyl, tetracetate
NCGC00160615-02
NCGC00160615-03
NCGC00254310-01
[(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-[(2S,3S,4R,5R)-3,4-diacetoxy-2,5-bis(acetoxymethyl)tetrahydrofuran-2-yl]oxy-tetrahydropyran-2-yl]methyl acetate
BS-15102
SY059951
HY-119309
CS-0066987
NS00014139
S0052
D-Saccharose octaacetate;Octa-O-acetylsucrose
D-(+)-Sucrose octaacetate, analytical standard
D05935
F20296
SBI-0654056.0001
F817908
Q410482
SR-01000883711
SR-01000883711-1
BRD-K01294196-001-01-5
Sucrose octaacetate, United States Pharmacopeia (USP) Reference Standard
|A-D-Glucopyranoside, 1,3,4,6-tetra-O-acetyl-|A-D-fructofuranosyl, 2,3,4,6-tetraacetate