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Quassin

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Identification
Molecular formula
C22H28O6
CAS number
76-78-8
IUPAC name
3-[(1R,3S,5S,10R,11R,13R,14S,17R)-3-[[(3aR,6S)-7-hydroxy-2,2,4-trimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-1,5,11,14-tetrahydroxy-10-(hydroxymethyl)-13-methyl-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
State
State

At room temperature, quassin is typically solid. It exists as either a crystalline solid or an amorphous powder.

Melting point (Celsius)
210.00
Melting point (Kelvin)
483.15
Boiling point (Celsius)
824.00
Boiling point (Kelvin)
1 097.15
General information
Molecular weight
574.65g/mol
Molar mass
574.6520g/mol
Density
1.3664g/cm3
Appearence
Quassin appears as a colorless, crystalline substance or a white amorphous powder. It is often found in the form of small flakes or needles and is noted for its intensely bitter taste.
Comment on solubility

Solubility of 3-[(1R,3S,5S,10R,11R,13R,14S,17R)-3-[[(3aR,6S)-7-hydroxy-2,2,4-trimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-1,5,11,14-tetrahydroxy-10-(hydroxymethyl)-13-methyl-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one

The solubility of this intricate compound is largely influenced by its complex molecular structure and a variety of functional groups. Here are some insights regarding its solubility characteristics:

  • Polarity: Due to the presence of multiple hydroxyl (–OH) groups, the compound exhibits a significant degree of polarity, which generally enhances its solubility in polar solvents such as water.
  • Functional Groups: The inclusion of both hydrophilic (water-attracting) and hydrophobic (water-repelling) components can lead to a limited solubility in non-polar solvents.
  • Hydrogen Bonding: The numerous –OH groups facilitate strong hydrogen bonding interactions. This property can help increase solubility in organic solvents that can also engage in hydrogen bonding.
  • Temperature Effect: Like many compounds, increased temperature may enhance solubility by breaking intermolecular interactions, allowing for better dissolution.

In conclusion, while this compound may be soluble in certain polar environments, its solubility profile is quite complex and would require careful evaluation under various conditions to fully ascertain.

Interesting facts

Interesting Facts about 3-[(1R,3S,5S,10R,11R,13R,14S,17R)-3-[[[3aR,6S)-7-hydroxy-2,2,4-trimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-1,5,11,14-tetrahydroxy-10-(hydroxymethyl)-13-methyl-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one

This compound is a **complex natural product** with intriguing structural features that showcase the beauty of organic chemistry. Derived from a family of compounds widely recognized for their medicinal properties, it holds promise in various fields:

  • Pharmacological Potential: Its intricate molecular composition suggests interesting *biological activity*, potentially interacting with enzymes or receptors in the body.
  • Stereochemistry: The specific arrangement of atoms and functional groups in this compound plays a crucial role in its biological activity, making it a subject of *drug design* studies.
  • Natural Isolate: This compound can be extracted from natural sources, and its synthesis can also be leveraged for creating analogs in medicinal chemistry.
  • Study of Terpenes: As a complex structure, studying this compound aids in understanding the larger class of terpenoids, known for their diverse roles in nature.

Many chemists remain fascinated by such compounds, stating, "Nature has already optimized the structure for us!" Encouraging chemists to explore *natural products* is a vital step toward innovating treatments in modern medicine.

Overall, the structural and functional diversity offered by compounds like this one emphasizes the need for continuous research and exploration in the fields of biochemistry and pharmacology.

Synonyms
Ouabain acetonide
O-Isopropylidene ouabain
Mono-O-isopropylidene ouabain
BRN 1416265
27799-55-9
5-beta-Card-20(22)-enolide, 3-beta-((6-deoxy-3,4-O-isopropylidene-alpha-L-mannopyranosyl)oxy)-1-beta,5,11-alpha,14,19-pentahydroxy-
RefChem:367056
DTXSID40950479
3-{[6-Deoxy-3,4-O-(1-methylethylidene)hexopyranosyl]oxy}-1,5,11,14,19-pentahydroxycard-20(22)-enolide