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Tanshinone IIA

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Identification
Molecular formula
C19H18O3
CAS number
568-73-0
IUPAC name
(4R)-2,2,6a,6b,9,9,12a-heptamethyl-4-(2-methylbut-2-enoyloxy)-10-oxo-3,4,5,6,6a,7,8,8a,11,12,13,14b-dodecahydro-1H-picene-4a-carboxylic acid
State
State

At room temperature, Tanshinone IIA exists as a solid.

Melting point (Celsius)
182.00
Melting point (Kelvin)
455.15
Boiling point (Celsius)
460.00
Boiling point (Kelvin)
733.15
General information
Molecular weight
310.37g/mol
Molar mass
310.3670g/mol
Density
1.1705g/cm3
Appearence

Tanshinone IIA appears as an orange-red crystalline solid. It is a natural compound found in the roots of Salvia miltiorrhiza, a species of sage. This compound is known for being relatively insoluble in water, contributing to its crystalline appearance.

Comment on solubility

Solubility Overview

The compound (4R)-2,2,6a,6b,9,9,12a-heptamethyl-4-(2-methylbut-2-enoyloxy)-10-oxo-3,4,5,6,6a,7,8,8a,11,12,13,14b-dodecahydro-1H-picene-4a-carboxylic acid is a complex chemical structure that influences its solubility characteristics in various solvents.

Factors Influencing Solubility

Several factors play a crucial role in determining the solubility of this compound:

  • Molecular Structure: The presence of bulky methyl groups and the unique carboxylic acid functional group can affect solubility. Carboxylic acids often have better solubility in polar solvents due to their ability to form hydrogen bonds.
  • Polarity: This compound's extensive hydrocarbon framework may lend hydrophobic characteristics, suggesting limited solubility in water, yet possibly improved solubility in organic solvents.
  • Temperature: Generally, an increase in temperature can enhance the solubility of organic compounds, which may apply to this compound as well.

Solubility Insights

Given the structure and functional groups present in this compound, one might expect:

  • Moderate solubility in organic solvents such as ethanol and acetone.
  • Poor solubility in water due to the bulky aliphatic groups and limited polar interactions.

As a general observation in organic chemistry, "Like dissolves like," meaning the solubility patterns exhibit preference for similar molecular characteristics between solute and solvent. Understanding the *solubility behavior* of such intricate compounds is crucial for their potential applications in various chemical domains.

Interesting facts

Interesting Facts about (4R)-2,2,6a,6b,9,9,12a-heptamethyl-4-(2-methylbut-2-enoyloxy)-10-oxo-3,4,5,6,6a,7,8,8a,11,12,13,14b-dodecahydro-1H-picene-4a-carboxylic acid

This complex organic compound is a fascinating example of the rich diversity found in organic chemistry. Here are some interesting points to consider:

  • Synthetic Versatility: The intricate structure offers a range of possibilities in synthetic organic chemistry, particularly for creating complex polymeric materials and drug intermediates.
  • Structural Diversity: The presence of multiple methyl groups and a unique enoyloxy functional group contributes to its structural complexity, making it a subject of interest in stereochemistry.
  • Bioactivity Potential: Compounds with similar structural motifs often demonstrate promising bioactivities, such as antimicrobial or anti-inflammatory properties, paving the way for potential medicinal applications.
  • Research Interest: The unique arrangement of carbon atoms and functional groups makes it a candidate for research in materials science, especially for developing new molecules with specific electronic properties.
  • Historical Significance: The study of dodecahydro-1H-picene derivatives has contributed significantly to our understanding of polycyclic aromatic hydrocarbons and their environmental effects.

As researchers delve into the potential uses and understanding of this compound, they are reminded of the vast world that exists within molecular structures. As one chemist aptly stated, "The beauty of chemistry lies in its complexity and the endless opportunities for new discoveries."

This compound exemplifies how an intricate molecular design can lead to profound implications in both natural processes and synthetic applications.