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Sucrose octaacetate

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

At room temperature, sucrose octaacetate exists as a solid. It can be processed into powder or crystalline granules for various applications, notably for its bitter properties.

Melting point (Celsius)
82.00
Melting point (Kelvin)
355.00
Boiling point (Celsius)
180.00
Boiling point (Kelvin)
453.00
General information
Molecular weight
678.65g/mol
Molar mass
678.6500g/mol
Density
1.2800g/cm3
Appearence

Sucrose octaacetate typically appears as a colorless to pale yellow solid. It is often seen in the form of powder or crystalline granules. The compound has a significant bitter taste, which makes it useful as a bitterant in various applications.

Comment on solubility

Solubility Characteristics

The compound [(2R,3R,4S,5S)-5-(acetoxymethyl)-5-[(2R,3R,4S,5R,6R)-6-(acetoxymethyl)-3,4,5-tris(2-methylpropanoyloxy)tetrahydropyran-2-yl]oxy-3,4-bis(2-methylpropanoyloxy)tetrahydrofuran-2-yl]methyl 2-methylpropanoate exhibits intriguing solubility properties that warrant exploration:


  • Polar versus Nonpolar Solvents: Due to its multiple acetoxymethyl and propanoyloxy functional groups, this compound is likely more soluble in polar solvents such as water, methanol, and ethanol than in nonpolar solvents.
  • Temperature Influence: The solubility of this compound may be temperature-dependent, with higher temperatures generally increasing solubility, particularly for organic compounds.
  • Concentration Level: In concentrated solutions, potential interactions among molecules, such as hydrogen bonding, could lead to a decrease in the compound's solubility as saturation is approached.

As a result, it can be concluded that the solubility of this complex compound is significantly affected by various factors, including solvent type and temperature, making it essential to consider these aspects during practical applications and reactions.

Interesting facts

Interesting Facts about the Compound

This compound exhibits a fascinating structure and is a part of a larger class of organic molecules renowned for their biological activity and synthetic applications. Here are some engaging insights:

  • Complexity: The compound showcases a high degree of stereochemistry, with specific R and S configurations critical for its biological interactions, often influencing how it binds to enzymes and receptors in metabolic pathways.
  • Natural Derivatives: Many compounds similar to this one are derived from natural products, particularly those involved in secondary metabolite pathways. This highlights the potential for discovering novel therapeutic agents.
  • Functional Groups: The presence of multiple ester functionalities (acetoxymethyl and 2-methylpropanoate) contributes to its properties and reactivity. This diversity in functional groups often allows for interesting synthetic transformations.
  • Potential Applications: Given its structural complexity, such compounds are often studied for potential applications in medicinal chemistry, especially in the design of antitumor or antiviral agents.
  • Chirality: The chiral centers present in the molecule not only signify its potential pharmacological significance but also pose interesting synthetic challenges in racemic vs. enantiomeric synthesis, making it a fascinating subject for chemists interested in asymmetric synthesis.

In summary, the compound serves as a vivid illustration of how structural intricacies can influence function and reactivity, providing a robust topic for further research and discussion in the field of organic and medicinal chemistry.

Synonyms
SAIB
Sucrose, diacetate hexaisobutyrate
Saccharose acetate isobutyrate
SAIB 100S
H5KI1C3YTV
Isobutyric acid, hexaester with sucrose diacetate
INS NO.444
INS-444
alpha-D-Glucopyranoside, 6-O-acetyl-1,3,4-tris-O-(2-methyl-1-oxopropyl)-beta-D-fructofuranosyl, 6-acetate 2,3,4-tris(2-methylpropanoate)
((2R,3R,4S,5S)-5-((acetyloxy)methyl)-5-(((2R,3R,4S,5R,6R)-6-((acetyloxy)methyl)-3,4,5-tris((2-methylpropanoyl)oxy)oxan-2-yl)oxy)-3,4-bis((2-methylpropanoyl)oxy)oxolan-2-yl)methyl 2-methylpropanoate
[(2R,3R,4S,5S)-5-[(acetyloxy)methyl]-5-{[(2R,3R,4S,5R,6R)-6-[(acetyloxy)methyl]-3,4,5-tris[(2-methylpropanoyl)oxy]oxan-2-yl]oxy}-3,4-bis[(2-methylpropanoyl)oxy]oxolan-2-yl]methyl 2-methylpropanoate
RefChem:186394
DTXCID709340
DTXSID5029340
204-771-6
126-13-6
DTXSID3027035
Sucrose Acetate Isobutyrate
Sucrose acetoisobutyrate
Sucrose di(acetate) hexaisobutyrate
[(2R,3R,4S,5S)-5-(acetyloxymethyl)-5-[(2R,3R,4S,5R,6R)-6-(acetyloxymethyl)-3,4,5-tris(2-methylpropanoyloxy)oxan-2-yl]oxy-3,4-bis(2-methylpropanoyloxy)oxolan-2-yl]methyl 2-methylpropanoate
HSDB 5657
AI3-25354
EINECS 204-771-6
E444
UNII-H5KI1C3YTV
sucrose acetate isobutylate
Sucrose acetate isobutanoate
SCHEMBL591902
CCRIS 8550
CHEBI:177717
Sucrose acetate 2-methylpropanoate
AKOS015896890
Sucrose diacetate hexaisobutyrate, 8CI
SUCROSE ACETATE ISOBUTYRATE [FCC]
6-O-Acetyl-1,3,4-tris-O-(2-methyl-1-oxopropyl)-beta-D-fructofuranosyl alpha-D-glucopyranoside 6-acetate 2,3,4-tris(2-methylpropanoate)
SUCROSE ACETATE ISOBUTYRATE [HSDB]
E-444
EC 204-771-6
A805511
Q410537
SUCROSE DIACETATE HEXAISOBUTYRATE [USP-RS]
Isobutyric acid, hexaester with sucrose diacetate (8CI)
1-O-acetyl-3,4,6-tri-O-isobutyryl-beta-D-fructofuranosyl 6-O-acetyl-2,3,4-tri-O-isobutyryl-alpha-D-glucopyranoside
1-O-acetyl-3,4,6-tris-O-(2-methylpropanoyl)-beta-D-fructofuranosyl 6-O-acetyl-2,3,4-tris-O-(2-methylpropanoyl)-alpha-D-glucopyranoside
2-methylpropanoic acid [(2R,3R,4S,5S)-5-(acetyloxymethyl)-5-[[(2R,3R,4S,5R,6R)-6-(acetyloxymethyl)-3,4,5-tris(2-methyl-1-oxopropoxy)-2-oxanyl]oxy]-3,4-bis(2-methyl-1-oxopropoxy)-2-oxolanyl]methyl ester