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Cerebroside

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Identification
Molecular formula
C34H67N2O15
CAS number
1334-66-9
IUPAC name
N-[2-[3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-6-[2-[5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]-2-hydroxy-ethyl]-4,5-dihydroxy-tetrahydropyran-3-yl]hexadec-2-enamide
State
State

At room temperature, cerebrosides are typically solids. They are stable compounds and can be handled without special precautions, although they should be stored in a dry environment.

Melting point (Celsius)
215.00
Melting point (Kelvin)
488.15
Boiling point (Celsius)
320.00
Boiling point (Kelvin)
593.15
General information
Molecular weight
719.97g/mol
Molar mass
719.9670g/mol
Density
1.0500g/cm3
Appearence

Cerebrosides appear as white to off-white solids or powders. Their appearance can vary slightly depending on the specific type of cerebroside and the impurities present.

Comment on solubility

Solubility of N-[2-[3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-6-[2-[5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]-2-hydroxy-ethyl]-4,5-dihydroxy-tetrahydropyran-3-yl]hexadec-2-enamide (C34H67N2O15)

The solubility characteristics of this complex compound can be understood by considering the following aspects:

  • Hydrophobic and Hydrophilic Balance: The long hexadec-2-enamide chain suggests a significant hydrophobic component, which may hinder solubility in aqueous environments. Conversely, the presence of multiple hydroxyl (-OH) and amino (-NH2) groups introduces hydrophilic attributes, enhancing solubility in polar solvents.
  • Solvent Interaction: Given the diverse functional groups, this compound is expected to dissolve well in solvents such as:
    • Water - due to the presence of multiple hydroxyl groups.
    • Alcohols - particularly those with lower molecular weights, like methanol and ethanol, due to their polar nature.
    • Dimethyl sulfoxide (DMSO) - which can solubilize both polar and non-polar components.
  • Limitations: Despite its potential for solubility in polar solvents, the overall large molecular size and hydrophobic tail may result in limited solubility in some organic solvents, necessitating careful selection based on the application.

In summary, while this compound exhibits promising solubility due to its functional groups, the overall balance between its hydrophobic and hydrophilic regions plays a critical role in its solubility behavior. As a result, experimentation with various solvents will be essential to determine the optimal conditions for solubilization.

Interesting facts

Interesting Facts about N-[2-[3-Acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-6-[2-[5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]-2-hydroxy-ethyl]-4,5-dihydroxy-tetrahydropyran-3-yl]hexadec-2-enamide

This complex compound, often recognized by its elegant name, is notable for several reasons which span its structural sophistication to its potential applications. Here are some captivating insights:

  • Unique Structure: The compound features a multifaceted structure, including multiple hydroxyl groups and amido functionalities that play a pivotal role in its reactivity and interaction with biological molecules.
  • Potential Therapeutic Applications: Compounds with similar structural motifs are often explored in medicinal chemistry. The presence of the pyrimidinyl moiety suggests potential use in antiviral therapies, as many antiviral agents derive from this structural class.
  • Natural Products Inspiration: The tetrahydropyran and tetrahydrofuran rings are common in various natural products, including many sugars and antibiotics. This resemblance hints at intriguing biochemical pathways the compound may influence.
  • Versatile Synthetic Pathways: The synthesis of such compounds is an exciting area of organic chemistry, involving multiple steps of protection and deprotection which are essential for functional group manipulation.
  • Research Interests: Scientists are investigating how variations in the acetyl and hydroxymethyl groups can influence the physicochemical properties and biological activities of the compound.

In summary, N-[2-[3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-6-[2-[5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]-2-hydroxy-ethyl]-4,5-dihydroxy-tetrahydropyran-3-yl]hexadec-2-enamide stands as a remarkable example of the complexity found in modern organic compounds. Its multifaceted character opens doors for innovative research in both synthetic and medicinal chemistry.