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D-Arbutin

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Identification
Molecular formula
C12H16O7
CAS number
497-76-7
IUPAC name
1-[4-[[(2R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]amino]phenyl]ethanone
State
State

At room temperature, D-Arbutin is in a solid state.

Melting point (Celsius)
195.00
Melting point (Kelvin)
468.15
Boiling point (Celsius)
412.50
Boiling point (Kelvin)
685.65
General information
Molecular weight
272.25g/mol
Molar mass
272.2510g/mol
Density
1.4550g/cm3
Appearence

D-Arbutin is a white crystalline solid. It is known for its fine powdery texture and appears as a white to off-white crystalline material. When observed under light, it maintains a uniform lusterless appearance.

Comment on solubility

Solubility of 1-[4-[[(2R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]amino]phenyl]ethanone

The solubility of 1-[4-[[(2R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]amino]phenyl]ethanone is influenced by its unique structural features and functional groups. This compound possesses a number of hydroxyl (–OH) groups, which generally enhance solubility in polar solvents such as water. Here are some key points regarding its solubility:

  • Highly Polar: The presence of multiple hydroxyl groups suggests that this compound is likely to be polar, allowing it to mix well with polar solvents.
  • Hydrogen Bonding: The ability to form hydrogen bonds significantly increases solubility in aqueous solutions.
  • Effects of Structure: The tetrahydropyran ring adds a layer of complexity, which may affect the overall solubility due to steric hindrance.
  • Potential Limitations: Despite its expected polar nature, steric effects from the bulky groups may limit complete solubility under certain conditions.

In summary, while the compound's functional groups predict enhanced solubility in water, the actual solubility will ultimately depend on the balance between polarity and structural constraints. Understanding these interactions is crucial for applications in drug design and biochemistry.

Interesting facts

Interesting Facts About 1-[4-[[(2R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]amino]phenyl]ethanone

This compound, characterized by its complex structure, belongs to a class of molecules with intriguing biochemical properties. Here are some fascinating insights into its significance:

  • Potential Therapeutic Applications: Compounds featuring hydroxyl and amino groups are often targeted for pharmaceutical research due to their ability to interact with biological systems. This molecule serves as a potential lead in drug discovery.
  • Natural Product Inspiration: The structure includes a tetrahydropyran ring, which is commonly found in many natural products, suggesting that this compound might mimic the activity of biologically active natural substances.
  • Acting on Receptors: The phenyl group and various hydroxyl groups can enhance interactions with specific biomolecular targets, potentially leading to effects on enzyme inhibition or receptor modulation.
  • Chirality Matters: The (2R,5S) configuration points to specific stereochemistry, a critical aspect in medicinal chemistry where the spatial arrangement of atoms can drastically influence biological activity.
  • Research Interest: Chemical scientists are particularly interested in how such compounds can be synthesized efficiently and how their structural nuances can affect reactivity and solubility.

In summary, 1-[4-[[[2R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]amino]phenyl]ethanone is a compound rich with potential in both synthetic and medicinal chemistry. Its unique structure invites further exploration and study, making it a noteworthy component in the field.

Synonyms
p-Aminoacetophenone glucoside
Glikozyd p-aminoacetofenonu
Glikozyd p-aminoacetofenonu [Polish]
4'-(beta-D-Glucopyranosylamino)acetophenone
10563-84-5
1-(4-(beta-D-Glucopyranosylamino)phenyl)ethanone
Ethanone, 1-(4-(beta-D-glucopyranosylamino)phenyl)-
ACETOPHENONE, 4'-(beta-D-GLUCOPYRANOSYLAMINO)-
Ethanone, 1-(4-(beta-D-glucopyranosylamino)phenyl)-(9CI)
DTXSID00909640