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Chlorogenic Acid

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Identification
Molecular formula
C16H18O9
CAS number
327-97-9
IUPAC name
(1S,3R,4R,5R)-3-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,4,5-trihydroxy-cyclohexanecarboxylic acid
State
State

Chlorogenic Acid is generally a solid at room temperature with a crystalline structure. It is known to be stable under standard conditions and decomposes upon heating before reaching its boiling point.

Melting point (Celsius)
205.00
Melting point (Kelvin)
478.20
Boiling point (Celsius)
553.10
Boiling point (Kelvin)
826.30
General information
Molecular weight
354.31g/mol
Molar mass
354.3120g/mol
Density
1.6500g/cm3
Appearence

Chlorogenic acid typically appears as a crystalline solid, frequently characterized by its light to brownish-yellow coloration. The compound features a translucent or opaque look depending on the purity and presence of any impurities or additives.

Comment on solubility

Solubility of (1S,3R,4R,5R)-3-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,4,5-trihydroxy-cyclohexanecarboxylic acid

This compound exhibits intriguing solubility characteristics, primarily due to its complex structure that includes multiple hydroxyl groups and a hydrophilic nature. The presence of the hydroxyl (–OH) groups enhances its ability to interact with water molecules, leading to improved solubility in aqueous environments. Consider the following aspects:

  • Polar Nature: The chemical will likely have good solubility in polar solvents like water because hydroxyl groups can form hydrogen bonds with water.
  • Hydrophobic Interactions: Any hydrophobic portions of the molecule may hinder solubility in purely aqueous conditions but may be soluble in organic solvents.
  • pH Dependence: As a carboxylic acid, changes in pH can significantly affect its solubility, as deprotonation may lead to the formation of soluble anionic species.
  • Temperature Influence: Generally, increased temperature can enhance the solubility of many compounds, including this one, depending on its thermal stability.

In light of these factors, it can be concluded that the solubility of this compound is largely influenced by environmental conditions and the balance between its polar and non-polar characteristics. Understanding these elements is crucial in applications, such as drug formulation where solubility plays a vital role in bioavailability.

Interesting facts

Interesting Facts about (1S,3R,4R,5R)-3-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,4,5-trihydroxy-cyclohexanecarboxylic acid

This compound is a fascinating example of a complex organic molecule that exhibits significant biological activity. It belongs to a class of compounds known as polyphenols, which are widely recognized for their health benefits. Here are some intriguing aspects about this compound:

  • Natural Occurrence: Compounds like this are commonly found in various plants, particularly fruits and vegetables, where they contribute to the plant's color, flavor, and health benefits.
  • Antioxidant Properties: As a polyphenolic compound, it possesses potent antioxidant properties, helping to neutralize harmful free radicals in the body.
  • Potential Health Benefits: Research suggests that such compounds may reduce the risk of chronic diseases, including heart disease, diabetes, and certain cancers, due to their anti-inflammatory effects.
  • Applications in Medicine: Due to its structural complexity, this compound may serve as a lead structure for the development of new pharmaceuticals, especially in the field of nutraceuticals.
  • Understanding Structure-Activity Relationships: The intricate arrangement of hydroxyl groups and the cyclohexane ring in this molecule offers a rich ground for studying how changes in structure can influence biological activity.

In summary, the compound (1S,3R,4R,5R)-3-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,4,5-trihydroxy-cyclohexanecarboxylic acid exemplifies the intersection of chemistry, biology, and medicine. Its complex structure encompasses a wealth of potential applications and insights into the ways in which nature's compounds can contribute to human health.

Synonyms
NSC70861
NSC407296
(1S,3R,4R,5R)-3-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,4,5-trihydroxy-cyclohexanecarboxylic acid
Spectrum_001846
SpecPlus_000957
Prestwick0_000427
Prestwick1_000427
Spectrum2_001898
Spectrum3_001797
KBioSS_002357
DivK1c_007053
SPBio_001836
SPBio_002353
CHEMBL3186431
KBio1_001997
KBio2_002354
KBio2_004922
KBio2_007490
KBio3_002855
AKOS030228500
SMP1_000066
Q27167119
(1S,3R,4R,5R)-3-[3-(3,4-dihydroxyphenyl)-1-oxoprop-2-enoxy]-1,4,5-trihydroxy-1-cyclohexanecarboxylic acid