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Caryophyllene

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Identification
Molecular formula
C15H24
CAS number
87-44-5
IUPAC name
4,11,11-trimethyl-8-methylene-bicyclo[7.2.0]undec-4-ene
State
State

At room temperature, caryophyllene is in a liquid state. It is a terpene found in the essential oils of many plants, providing them with a distinctive aroma.

Melting point (Celsius)
-7.00
Melting point (Kelvin)
266.15
Boiling point (Celsius)
262.00
Boiling point (Kelvin)
535.15
General information
Molecular weight
204.36g/mol
Molar mass
204.3570g/mol
Density
0.9059g/cm3
Appearence

Caryophyllene is typically a colorless to pale yellow liquid. It has a spicy, woody, and warm aroma, reminiscent of cloves and black pepper. The compound is a common constituent of various essential oils and contributes to their distinctive scents.

Comment on solubility

Solubility of 4,11,11-trimethyl-8-methylene-bicyclo[7.2.0]undec-4-ene

The solubility of 4,11,11-trimethyl-8-methylene-bicyclo[7.2.0]undec-4-ene is quite intriguing due to its complex bicyclic structure. This compound is primarily known for its hydrophobic characteristics, which significantly affect its solubility profile.

Factors influencing solubility:

  • Hydrophobic Nature: The bulky and nonpolar nature of the hydrocarbon skeleton contributes to its limited solubility in polar solvents like water.
  • Solvent Effects: It tends to dissolve better in organic solvents such as hexane, toluene, and ether due to similar nonpolar interactions.
  • Temperature Dependency: Like many organic compounds, its solubility may increase with temperature, which can enhance molecular motion and interactions with the solvent.

Given its distinctive structure, it is pertinent to note that the solubility can vary widely depending on the medium. For instance, in a nonpolar solvent, it may exhibit significant solubility, showcasing its ability to form stable interactions. As a result, understanding the solubility behavior of this compound is crucial for applications in organic chemistry and materials science.

In summary, while 4,11,11-trimethyl-8-methylene-bicyclo[7.2.0]undec-4-ene may present challenges in solubility when confronted with polar solvents, it remains soluble in nonpolar environments, highlighting the classic principle of 'like dissolves like'.

Interesting facts

Interesting Facts about 4,11,11-trimethyl-8-methylene-bicyclo[7.2.0]undec-4-ene

4,11,11-trimethyl-8-methylene-bicyclo[7.2.0]undec-4-ene is a fascinating compound that showcases the complexity and beauty of bicyclic structures in organic chemistry. This compound belongs to the family of bicyclic alkenes, which are characterized by two fused ring systems. Here are some intriguing aspects of this compound:

  • Bicyclic Structures: The compound features a unique bicyclic structure that provides interesting steric and electronic properties. These properties can lead to a variety of reactivity patterns not found in monocyclic compounds.
  • Synthetic Importance: The synthesis of this compound often involves multi-step organic reactions that highlight the creativity and skill required in modern organic synthesis. It serves as an important intermediate in the synthesis of complex natural products.
  • Applications: This compound may have applications in materials science and medicinal chemistry. Compounds with similar structures may exhibit interesting biological activities, though specific studies on this particular molecule are limited.
  • Geometric Isomerism: The presence of double bonds and multiple substituents opens the door to geometric isomerism, which can significantly affect the physical and chemical properties of the compound.

In the pursuit of understanding molecules like 4,11,11-trimethyl-8-methylene-bicyclo[7.2.0]undec-4-ene, scientists delve into the realm of stereochemistry, reactivity, and molecular design. As stated by a renowned chemist, "The beauty of organic chemistry lies in the infinite possibilities of molecular transformations." Exploring compounds like this serves not only to enrich our knowledge but also to inspire future innovations in chemical research.

Synonyms
4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene
Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1S,4E,9R)-
4,11,11-Trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene
(-)-(E)-Caryophyllene;(-)-beta-caryophyllene;(-)-trans-Caryophyllene
(?)-|A-caryophyllene
4,11,11-trimethyl-8-methylene-bicyclo[7.2.0]undec-4-ene
SCHEMBL4195147
DTXSID70859143
AKOS030228124
DB-057003
DB-061346
NS00085736