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Acarbose

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Identification
Molecular formula
C25H43N3O18
CAS number
56180-94-0
IUPAC name
2-[(1S,2R,3R,4S,5R,6R)-2-[(2R,3R,4R,5S)-3-[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)tetrahydropyran-2-yl]oxy-4-formyl-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]oxy-5-guanidino-3,4,6-trihydroxy-cyclohexyl]guanidine
State
State

At room temperature, acarbose is a solid.

Melting point (Celsius)
164.00
Melting point (Kelvin)
437.15
Boiling point (Celsius)
433.50
Boiling point (Kelvin)
706.70
General information
Molecular weight
645.61g/mol
Molar mass
645.6080g/mol
Density
1.2800g/cm3
Appearence

Acarbose typically appears as a white to off-white powder.

Comment on solubility

Solubility of 2-[(1S,2R,3R,4S,5R,6R)-2-[(2R,3R,4R,5S)-3-[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)tetrahydropyran-2-yl]oxy-4-formyl-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]oxy-5-guanidino-3,4,6-trihydroxy-cyclohexyl]guanidine

The solubility of this complex compound is inherently related to its intricate molecular structure and multiple functional groups. In general, solubility can be influenced by several key factors:

  • Polarity: The presence of numerous hydroxyl groups (–OH) enhances the compound's polarity, likely increasing its solubility in polar solvents such as water.
  • Hydrogen Bonding: The ability of the molecule to form hydrogen bonds contributes to its solubility, as these interactions can help the compound dissolve in aqueous environments.
  • Ionization: Functional groups that can ionize may also enhance solubility in various solvents, particularly in physiological environments.

However, because of the compound's elaborate and bulky structure, solubility may not be as straightforward. Here are additional considerations:

  • The steric hindrance caused by bulky substituents might hinder interaction with solvent molecules.
  • The overall charge distribution across the molecule will play a key role in determining its affinity for different solvents.

It’s essential to note that generalizations about solubility can vary widely depending on specific conditions such as temperature and the presence of other solutes. In sum, while this compound may display considerable solubility in polar environments, its unique architecture poses challenges, emphasizing that “the whole is greater than the sum of its parts.”

Interesting facts

Interesting Facts about 2-[(1S,2R,3R,4S,5R,6R)-2-[(2R,3R,4R,5S)-3-[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)tetrahydropyran-2-yl]oxy-4-formyl-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]oxy-5-guanidino-3,4,6-trihydroxy-cyclohexyl]guanidine

This compound, known for its complex structure, is a member of the class of guanidine derivatives, which are notable for their roles in various biological processes. Here are some fascinating insights about this intriguing chemical:

  • Complexity in Structure: The intricate stereochemistry of this molecule showcases multiple chiral centers, highlighting the symmetry that is crucial in biochemical reactions and interactions.
  • Role in Biochemistry: Guanidines are often involved in enzyme active sites and can act as substrates or inhibitors, making them essential in pharmacology and biochemistry.
  • Potential Therapeutic Applications: Compounds like this one are studied for their potential therapeutic applications, particularly in treating conditions related to metabolic disorders or inflammatory diseases.
  • Research and Development: Ongoing research into guanidine derivatives continues to unveil new possibilities for drug development, focusing on their ability to modulate biological pathways.

As a chemistry student, you might appreciate the exquisite balance of stability and reactivity present in this compound, making it a key interest in medicinal chemistry and pharmaceutical research. It's examples like this that underscore the importance of understanding molecular structure in the pursuit of novel therapies!

Synonyms
Hydroxystreptomycin
Streptomycin C
6835-00-3
5'-Hydroxystreptomycin
QXR888I04O
2-[(1R,2R,3S,4R,5R,6S)-3-(diaminomethylideneamino)-4-[(2R,3R,4R,5S)-3-[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy-4-formyl-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-2,5,6-trihydroxycyclohexyl]guanidine
1,1'-((1R,2R,3S,4R,5R,6S)-4-(((2R,3R,4R,5S)-3-(((2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)tetrahydro-2H-pyran-2-yl)oxy)-4-formyl-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-2,5,6-trihydroxycyclohexane-1,3-diyl)diguanidine
1,1'-[(1R,2R,3S,4R,5R,6S)-4-({2-O-[2-deoxy-2-(methylamino)-alpha-L-glucopyranosyl]-3-C-formyl-alpha-L-lyxofuranosyl}oxy)-2,5,6-trihydroxycyclohexane-1,3-diyl]diguanidine
UNII-QXR888I04O
SCHEMBL35700
RETICULIN (ANTIBIOTIC)
HYDROXYSTREPTOMYCIN [MI]
CHEBI:24750
DTXSID20218483
AKOS040746907
D-Streptamine, O-2-deoxy-2-(methylamino)-alpha-L-glucopyranosyl-(1-2)-O-3-C-formyl-alpha-L-lyxofuranosyl-(1-4)-N,N'-bis(aminoiminomethyl)-
D-Streptamine, O-2-deoxy-2-(methylamino)-alpha-L-glucopyranosyl-(1-2)-O-3-C-formyl-alpha-L-lyxofuranosyl-(1-4)-N,N'-diamidino-
NS00011546
C17571
Q27109853
D-STREPTAMINE, O-2-DEOXY-2-(METHYLAMINO)-.ALPHA.-L-GLUCOPYRANOSYL-(1->2)-O-3-C-FORMYL-.ALPHA.-L-LYXOFURANOSYL-(1->4)-N1,N3-BIS(AMINOIMINOMETHYL)-
O-2-deoxy-2-(methylamino)-alpha-L-glucopyranosyl-(1-2)-O-3-C-formyl-alpha-L-lyxofuranosyl-(1-4)-N,N'-bis(aminoiminomethyl)-D-streptamine