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Rosmarinic acid

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Identification
Molecular formula
C18H16O8
CAS number
20283-92-5
IUPAC name
methyl 2-[3,4,5-trihydroxy-6-[(3,4,5-trihydroxytetrahydropyran-2-yl)oxymethyl]tetrahydropyran-2-yl]oxybenzoate
State
State

Rosmarinic acid is typically in a solid state at room temperature.

Melting point (Celsius)
171.00
Melting point (Kelvin)
444.15
Boiling point (Celsius)
319.00
Boiling point (Kelvin)
592.15
General information
Molecular weight
360.32g/mol
Molar mass
360.3190g/mol
Density
1.5258g/cm3
Appearence

Methyl 2-[3,4,5-trihydroxy-6-[(3,4,5-trihydroxytetrahydropyran-2-yl)oxymethyl]tetrahydropyran-2-yl]oxybenzoate, or commonly known as Rosmarinic acid, typically appears as a white to off-white powder. It is known for its crystalline nature when isolated in pure form.

Comment on solubility

Solubility of Methyl 2-[3,4,5-trihydroxy-6-[(3,4,5-trihydroxytetrahydropyran-2-yl)oxymethyl]tetrahydropyran-2-yl]oxybenzoate

The solubility of methyl 2-[3,4,5-trihydroxy-6-[(3,4,5-trihydroxytetrahydropyran-2-yl)oxymethyl]tetrahydropyran-2-yl]oxybenzoate is influenced by its intricate molecular structure and the presence of multiple hydroxy groups.

Key Points:

  • Hydrophilicity: The numerous hydroxyl (-OH) groups present contribute to its hydrophilic nature.
  • Solvent Interactions: It is likely to have significant solubility in polar solvents, especially water and alcohols.
  • Concentration Effect: As with many organic compounds, solubility may vary with concentration, temperature, and pH.
  • Solid Form: The crystalline form of the compound may exhibit lower solubility compared to its amorphous counterparts.

In summary, this compound's solubility properties are complex and are primarily governed by its ability to form hydrogen bonds with solvents due to the multiple hydroxyl groups. Therefore, in practical applications, it is essential to consider these aspects to optimize its use in various chemical environments.

Interesting facts

Interesting Facts about Methyl 2-[3,4,5-trihydroxy-6-[(3,4,5-trihydroxytetrahydropyran-2-yl)oxymethyl]tetrahydropyran-2-yl]oxybenzoate

This compound is an elegant example of a glycoside, where a sugar is linked to a non-carbohydrate moiety. It showcases how carbohydrates can be modified to create complex structures with unique properties. Here are some captivating insights:

  • Structurally Rich: This compound features multiple hydroxyl groups, indicative of its potential reactivity and ability to form hydrogen bonds, which can influence its interactions in biological systems.
  • Biological Significance: Glycosides like this one are often found in nature and serve diverse functions, from serving as sweeteners to acting as pharmaceuticals. They can modify the bioavailability of medicinal compounds.
  • Synthetic Pathways: The synthesis of such complex structures often involves several steps, including glycosylation reactions. Understanding these pathways can illuminate fundamental organic chemistry principles.
  • Functional Applications: Compounds of this class have potential uses in various fields such as food chemistry, pharmacology, and materials science, thanks to their modifiable sugar components.
  • Research Opportunities: The study of glycosides opens doors to research in drug design, specifically in the development of targeted therapies that harness the specificity of carbohydrate recognition.

As a noteworthy example of chemical creativity, this compound not only enriches our understanding of glycosidic linkages but also encourages further exploration into the synthesis and application of carbohydrate-derived compounds.

Synonyms
SCHEMBL7040744
methyl 2-[(6-o-pentopyranosylhexopyranosyl)oxy]benzoate
DTXSID40871690