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Colchicine

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Identification
Molecular formula
C22H25NO6
CAS number
64-86-8
IUPAC name
N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]formamide
State
State

Colchicine is a solid at room temperature. It is formulated mostly in an anhydrous state for pharmaceutical preparations.

Melting point (Celsius)
157.00
Melting point (Kelvin)
430.00
Boiling point (Celsius)
553.90
Boiling point (Kelvin)
827.00
General information
Molecular weight
399.44g/mol
Molar mass
399.4370g/mol
Density
1.6601g/cm3
Appearence

Colchicine is a white to pale yellow, crystalline powder. It is typically stable under normal conditions and readily dissolves in water or alcohol, imparting a bitter taste. The compound may undergo color changes when exposed to sunlight or traces of oxidizing agents.

Comment on solubility

Solubility of N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]formamide

The solubility of N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]formamide is an intriguing aspect of its chemical properties. Due to the complex structure of this compound, its solubility characteristics can be affected by several factors, which include:

  • Polarity: The presence of multiple methoxy groups and a formamide moiety contributes to both polar and nonpolar characteristics, potentially aiding in solubility in mixed solvents.
  • Steric hindrance: The bulky groups around the heptalene core may limit the ability of the compound to interact favorably with solvent molecules, thus affecting overall solubility.
  • Hydrogen bonding: The formamide functional group can engage in hydrogen bonding, enhancing its solubility in polar solvents, particularly water and alcohols.

As a result, it is generally expected that N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]formamide will exhibit:

  1. Higher solubility in polar protic solvents, such as ethanol and methanol.
  2. Moderate solubility in less polar solvents, depending on the specific solvent environment.

Experimental validation of these solubility properties is essential for practical applications, as they can vary significantly based on solvent conditions and temperature. Ultimately, understanding the solubility of such compounds provides critical insights for their use in various fields such as pharmacology and materials science.

Interesting facts

Interesting Facts about N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]formamide

N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]formamide is a fascinating compound that blends structural complexity with intriguing potential applications. Here are some noteworthy aspects of this compound:

  • Structural Significance: This compound features a robust benzo[a]heptalene backbone, which is a core structure found in various natural products. Its unique arrangement contributes to its chemical reactivity and biological activity.
  • Functional Groups: The presence of multiple methoxy groups enhances its solubility in organic solvents and may influence its biological interactions. Methoxy groups are known to modify the electronic characteristics of compounds, making them more active in biochemical pathways.
  • Potential Therapeutic Uses: Compounds with similar structures have been studied for their anticancer and anti-inflammatory properties. The integration of a formamide functional group can further enhance its potential as a drug candidate in medicinal chemistry.
  • Chirality: The compound specifically contains a chiral center at the 7-position of the benzo[a]heptalene structure. This chirality is crucial as it can result in different biological activities between enantiomers, an important consideration in drug development.
  • Research Interest: The complexity of this compound makes it a subject of interest for synthetic chemists. Investigating its synthesis and derivatization can lead to discovering novel compounds or optimizing its therapeutic potential.

In summary, N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]formamide is not just a chemical structure but a potential gateway to new discoveries in medicinal chemistry. As researchers continue to explore its characteristics, we may yet uncover a rich tapestry of applications that leverage its unique features.

Synonyms
Gloriosine
7411-12-3
N-Formyldeacetylcolchicine
N-Deacetyl-N-formylcolchicine
NSC 403142
N-Formyldesacetylcolchicine
Formyldescaetylcolchicine, N-
COLCHICINE, N-DEACETYL-N-FORMYL-
U02803H7OJ
NSC-403142
BRN 2824080
DTXSID80225057
Formamide, N-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo(a)heptalen-7-yl)-, (S)-
4-14-00-00942 (Beilstein Handbook Reference)
FORMAMIDE, N-((7S)-5,6,7,9-TETRAHYDRO-1,2,3,10-TETRAMETHOXY-9-OXOBENZO(A)HEPTALEN-7-YL)-
N-((7S)-5,6,7,9-TETRAHYDRO-1,2,3,10-TETRAMETHOXY-9-OXOBENZO(A)HEPTALEN-7-YL)FORMAMIDE
DTXCID80147548
630-568-0
Formamide, N-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo(a)heptalen-7-yl)-, (S)-(9CI)
N-Deacetyl-N-formyl Colchicine
N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]formamide
NSC403142
N-Formyl-N-deacetylcolchicine
N-Formyl-Deacetylcolchicine
CHEMBL85710
UNII-U02803H7OJ
GTPL7526
SCHEMBL4069971
CHEBI:138826
FORMYLDESACETYLCOLCHICINE, N-
MFCD00468038
AKOS017343603
CCG-208385
NCGC00163534-01
NCGC00163534-02
PD047744
COLCHICINE IMPURITY A [EP IMPURITY]
Gloriosine (N-Deacetyl-N-formyl-colchicin)
NS00094808
C19981
G87062
SR-05000002280
Q9268800
SR-05000002280-2
Formamide,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl)-, (S)-
Formamide,N-[(7S)-5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl]-
N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[d]heptalen-7-yl]formamide