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Epigallocatechin gallate (EGCG)

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Identification
Molecular formula
C22H18O11
CAS number
989-51-5
IUPAC name
4-[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-isobenzofuro[6,5-f][1,3]benzodioxol-8-one
State
State

At room temperature, epigallocatechin gallate is generally in a solid state, taking the form of a crystalline or powdery substance.

Melting point (Celsius)
221.00
Melting point (Kelvin)
494.15
Boiling point (Celsius)
595.40
Boiling point (Kelvin)
868.55
General information
Molecular weight
458.37g/mol
Molar mass
458.3730g/mol
Density
1.9000g/cm3
Appearence

Epigallocatechin gallate appears as a white to pale brown powder or crystalline solid. It is often extracted from green tea leaves and is available as a supplement in various forms.

Comment on solubility

Solubility of 4-[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-isobenzofuro[6,5-f][1,3]benzodioxol-8-one

The solubility of the compound with the chemical formula C22H18O11 can be quite complex due to its intricate structure, which includes multiple hydroxyl (-OH) groups and ether (-O-) functionalities. These features often play a significant role in the solubility behavior of organic compounds.

Factors Influencing Solubility

  • Polarity: The presence of multiple hydroxyl groups typically increases polarity, enhancing solubility in polar solvents like water.
  • Hydrogen Bonding: Hydroxyl groups can form hydrogen bonds with water, promoting solubility. This compound's trihydroxy and hydroxymethyl groups may significantly enhance its solubility profile.
  • Functional Groups: The presence of methoxy (-OCH3) groups also contributes to solubility as they offer additional interaction sites.

In general, one might expect the compound to be:

  • Highly soluble in water due to its polar nature and ability to engage in hydrogen bonding.
  • Less soluble in non-polar solvents, as the extensive functionalization in the molecule makes it less compatible with hydrophobic environments.

However, the actual solubility can vary depending on factors such as temperature, pH, and the presence of other solutes. Overall, this compound demonstrates a remarkable potential for solubility in aqueous environments, which highlights its intriguing chemical properties.

Interesting facts

4-[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-isobenzofuro[6,5-f][1,3]benzodioxol-8-one

This intriguing compound belongs to the class of organic molecules known as flavonoids and displays a remarkable structural complexity. Its multifaceted nature offers a glimpse into the fascinating world of polyphenolic compounds, widely recognized for their significant biological activities.

Interesting Facts:

  • Bioactivity: Compounds like this one have been studied for their potential health benefits, including antioxidant, anti-inflammatory, and even anti-cancer properties. This particular compound's diverse functional groups may contribute to its biological efficacy.
  • Chemical Structure: Featuring a unique arrangement of hydroxyl groups, methoxy substituents, and a tetrahydropyran ring, this compound showcases the intricate architecture often found in nature's molecules.
  • Natural Sources: Many compounds similar to this structure can be derived from plant sources, particularly fruits and vegetables, highlighting nature's ability to produce complex organic compounds for protection and survival.
  • Potential Uses: Owing to its unique molecular characteristics, this compound could be of interest in pharmaceutical research. Its structure might serve as a lead compound for developing new drugs targeting specific diseases.
  • Research Significance: The ongoing exploration of flavonoids in medicinal chemistry illustrates the potential of such compounds in creating functional foods and nutraceuticals that can enhance human health on multiple levels.

In summary, this compound exemplifies the intersection of nature and chemistry, where intricate molecular designs can lead to profound implications in health and medicine. It stands as a testament to the potential that lies within the classification of flavonoids, inviting further exploration and discovery.

Synonyms
4-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one
(-)-beta-Peltatin-5-o-beta-D-glucopyranoside
11024-59-2
Compound NP-008104
CHEBI:181373
ZINC05849284
AKOS040739378
4-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzouro[6,5-][1,3]benzodioxol-8-one