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Curcumin

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Identification
Molecular formula
C21H20O6
CAS number
458-37-7
IUPAC name
[4-acetoxy-15-[3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenyl-propanoyl]oxy-1,9,12-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
State
State

Curcumin is typically found in solid form at room temperature. It is often encountered in powdered form as a component of turmeric, in which it naturally occurs.

Melting point (Celsius)
183.00
Melting point (Kelvin)
456.15
Boiling point (Celsius)
650.00
Boiling point (Kelvin)
923.15
General information
Molecular weight
368.39g/mol
Molar mass
368.3850g/mol
Density
1.2660g/cm3
Appearence

Curcumin is a bright yellow crystalline solid. It is known for its vibrant hue, which can stain surfaces it comes in contact with. It is commonly available in powdered form and is often used as a food coloring and spice.

Comment on solubility

Solubility of 4-acetoxy-15-[3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenyl-propanoyl]oxy-1,9,12-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl benzoate (C21H20O6)

The solubility characteristics of this complex organic compound are quite intriguing and can be summarized through several key points:

  • Polarity: Given its extensive functional groups, particularly the presence of hydroxyl (-OH) and carbonyl (C=O) groups, we can expect some degree of polarity, which often contributes to solubility in polar solvents such as water.
  • Hydrophobic Interactions: However, the large hydrophobic regions introduced by the tert-butoxycarbonylamino and aromatic structures may lead to limited solubility in highly polar solvents.
  • Solvent Dependency: The solubility of this compound is likely to be higher in organic solvents like ethanol, methanol, or dimethyl sulfoxide (DMSO), which can effectively solvate both the hydrophilic and hydrophobic portions of the molecule.
  • Temperature Influence: It is common for solubility to increase with temperature, so warming the solution may enhance solubility, particularly in organic solvents.

In summary, while the compound likely shows some solubility in polar solvents, its significant molecular complexity and hydrophobic regions may necessitate the use of specific organic solvents for effective dissolution. As noted by chemists, "The principle of 'likes dissolving in likes' often governs the solubility behavior of organic compounds." Thus, careful consideration of solvent choice is essential when working with this compound.

Interesting facts

4-acetoxy-15-[3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenyl-propanoyl]oxy-1,9,12-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl benzoate

This compound is a fascinating example of organic chemistry's complexity and creativity. It belongs to a class of compounds known for their unique structure and functional groups that play significant roles in various chemical reactions and biological activities.

Key Features:

  • Complex Structure: The compound features multiple ring systems and functional groups, such as acetoxy and carbamate moieties, which contribute to its potential reactivity and interaction with biological targets.
  • Biological Significance: Compounds like this are often explored for their pharmacological properties, which may include anti-inflammatory or anticancer activities. Its diversity in structure allows for a wide range of biological investigations.
  • Synthetic Versatility: The synthesis of this compound can involve various methods, showcasing the importance of organic synthesis techniques in developing complex molecules.
  • Historical Context: Understanding such compounds gives insights into the advancements in medicinal chemistry and the ongoing quest for novel therapeutic agents.

The examination of 4-acetoxy-15-[3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenyl-propanoyl]oxy-1,9,12-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl benzoate not only highlights the intricacies of chemical bonding and structure but also serves as a reminder of the intersection of chemistry and biology. As the renowned chemist Linus Pauling once said, "The best way to have a good idea is to have a lot of ideas." Compounds like this inspire further research and innovation in the field, emphasizing the importance of continued exploration in the realm of chemical science.

Synonyms
Docetaxol
[4-Acetyloxy-1,9,12-trihydroxy-15-[2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]oxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
MFCD00871399
SCHEMBL21465719
CHEBI:93763
DTXSID90861228
114915-20-7
BCP33094
LSM-4270
QMB86725
Docetaxel EP Impurity C;4-Epidocetaxel
NCGC00387828-01
NCGC00387828-02
LS-15450
SY016927
Q27165454
[(1S,2S,3R,4S,7R,9R,10S,12R,15S)-4-acetyloxy-1,9,12-trihydroxy-15-[(2R,3S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]oxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0^{3,10.0^{4,7]heptadec-13-en-2-yl] benzoate
4-(acetyloxy)-13-({3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoyl}oxy)-1,7,10-trihydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate
Benzenepropanoic acid,b-[[(1,1-dimethylethoxy)carbonyl]amino]-a-hydroxy-,12b-(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,6,11-trihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester