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Sphingosine

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Identification
Molecular formula
C18H37NO2
CAS number
123-78-4
IUPAC name
2-(dimethylamino)octadec-4-ene-1,3-diol
State
State

At room temperature, sphingosine is typically in a solid state; specifically, it is a waxy solid. Due to its long hydrocarbon chain, it demonstrates typical characteristics of high molecular weight lipids.

Melting point (Celsius)
76.00
Melting point (Kelvin)
349.00
Boiling point (Celsius)
541.10
Boiling point (Kelvin)
814.30
General information
Molecular weight
299.49g/mol
Molar mass
299.4860g/mol
Density
1.0110g/cm3
Appearence

Sphingosine typically appears as a white waxy solid or a white crystalline powder. It can also be described as having a slight pearlescent sheen when in pure, unmodified form.

Comment on solubility

Solubility of 2-(dimethylamino)octadec-4-ene-1,3-diol (C18H37NO2)

The solubility of 2-(dimethylamino)octadec-4-ene-1,3-diol is influenced by its unique chemical structure, which contributes to both hydrophilic and hydrophobic characteristics.

Factors Affecting Solubility

  • Hydrophobic Alkyl Chain: The long carbon chain of octadec-4-ene promotes solubility in non-polar solvents, making it lipophilic.
  • Hydrophilic Functional Groups: The presence of hydroxyl (-OH) groups and the dimethylamino (-N(CH3)2) group enhances the compound's affinity for polar solvents like water.
  • pH Dependence: The solubility may vary with pH, particularly due to the protonation state of the amino group, which can alter its polarity.

In practical terms, this compound is typically expected to be:

  • Moderately Soluble: Although the alkyl chain is long, the functional groups can enable solubility in a range of polar and non-polar solvents.
  • Temperature Sensitive: Solubility could increase with temperature, a common feature for many organic compounds.

As noted, the balance between the hydrophobic tail and the hydrophilic headgroups is crucial. This character can result in unique applications in pharmaceutical formulations or surfactants, showcasing the versatility of solubility behavior in organic compounds.

Interesting facts

Interesting Facts about 2-(Dimethylamino)octadec-4-ene-1,3-diol

2-(Dimethylamino)octadec-4-ene-1,3-diol, often referred to as a type of amphiphilic compound, offers a unique combination of properties that make it particularly intriguing for various applications in chemistry and biology.

1. Dual Nature

This compound has both hydrophilic (water-attracting) and hydrophobic (water-repelling) regions due to its long hydrophobic tail and polar hydroxyl groups. This amphiphilic nature allows it to form:

  • Micelles: Organized structures that can encapsulate hydrophobic substances.
  • Emulsions: Mixtures of immiscible liquids, which are essential in pharmaceuticals and cosmetics.

2. Biological Applications

Due to its chemical structure, 2-(dimethylamino)octadec-4-ene-1,3-diol shows potential in:

  • Drug Delivery: Facilitating the transport of therapeutic agents across cell membranes.
  • Antimicrobial Activity: The presence of a quaternary ammonium group often contributes to its effectiveness against a range of microorganisms.

3. Synthetic Pathways

The synthesis of this compound involves complex organic reactions, typically starting from readily available fatty acids or alcohols. Chemists often use:

  • Substitution reactions: To introduce the dimethylamino group.
  • Reduction reactions: To create the necessary alcohol functional groups.

4. Research Potential

With ongoing research into biomimetic materials, 2-(dimethylamino)octadec-4-ene-1,3-diol presents exciting opportunities in developing:

  • Smart Surfaces: That can respond to environmental changes.
  • New Therapeutics: With targeted action mechanisms for drug delivery systems.

In summary, the multifaceted utility of this compound makes it a focal point in both academic research and industrial applications, underscoring the importance of understanding amphiphilic molecules in advancing modern chemistry.

Synonyms
2-(dimethylamino)octadec-4-ene-1,3-diol
132031-17-5
2-DIMETHYLAMINO-4-OCTADECENE-1,3-DIOL
IN1356
SCHEMBL121926
DTXSID20274423
HMS3870E03
NS00016778