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Tacrolimus

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Identification
Molecular formula
C44H69NO12
CAS number
104987-11-3
IUPAC name
1-[(1R,5R,6S,9S,12R)-9,12-dihydroxy-6,16-dimethyl-10,19-dioxa-16-azahexacyclo[12.5.3.15,9.01,14.02,11.06,11]tricosa-2,21-dien-22-yl]ethyl 2-ethyl-4-methyl-1H-pyrrole-3-carboxylate
State
State

Solid: Tacrolimus is typically encountered as a solid at room temperature.

Melting point (Celsius)
113.00
Melting point (Kelvin)
386.15
Boiling point (Celsius)
873.15
Boiling point (Kelvin)
600.00
General information
Molecular weight
804.02g/mol
Molar mass
804.0190g/mol
Density
1.1000g/cm3
Appearence

Tacrolimus appears as a white to off-white crystalline powder.

Comment on solubility

Solubility of 1-[(1R,5R,6S,9S,12R)-9,12-dihydroxy-6,16-dimethyl-10,19-dioxa-16-azahexacyclo[12.5.3.15,9.01,14.02,11.06,11]tricosa-2,21-dien-22-yl]ethyl 2-ethyl-4-methyl-1H-pyrrole-3-carboxylate

The solubility of the compound 1-[(1R,5R,6S,9S,12R)-9,12-dihydroxy-6,16-dimethyl-10,19-dioxa-16-azahexacyclo[12.5.3.15,9.01,14.02,11.06,11]tricosa-2,21-dien-22-yl]ethyl 2-ethyl-4-methyl-1H-pyrrole-3-carboxylate can vary significantly based on several factors. Here are a few important considerations regarding its solubility:

  • Polarity: The presence of multiple hydroxyl (-OH) and carboxyl (-COOH) functional groups often increases the polarity of a compound, potentially enhancing solubility in polar solvents like water.
  • Hydrophobic structures: Despite the polar groups, the large hydrophobic sections of this compound may hinder full solubility in highly polar solvents, leading to a preference for organic solvents.
  • Temperature: Solubility is generally temperature-dependent. As temperature increases, solubility in most solvents also increases.
  • pH levels: The ionization of the carboxyl group can also alter the solubility profile, depending on the pH of the solution, enhancing solubility in alkaline conditions.
  • Concentration: At higher concentrations, precipitation may occur if the solubility limit is exceeded, particularly when many hydrophobic interactions take place.

In essence, the solubility behavior of this compound is complex and affected by a myriad of factors, making it essential to consider these aspects during any formulation or analytical assessment. Understanding these intricacies allows researchers to predict how this compound interacts with various solvents and environments.

Interesting facts

Interesting Facts About 1-[(1R,5R,6S,9S,12R)-9,12-dihydroxy-6,16-dimethyl-10,19-dioxa-16-azahexacyclo[12.5.3.15,9.01,14.02,11.06,11]tricosa-2,21-dien-22-yl]ethyl 2-ethyl-4-methyl-1H-pyrrole-3-carboxylate

This complex compound, often referred to by its systematic name, belongs to a class of compounds known for their multifunctionality and structural intricacies. Here are some fascinating aspects of this molecule:

  • Structural Complexity: The compound features a hexacyclic arrangement, showcasing a remarkable variety of functional groups and chiral centers. This structural diversity contributes to its unique properties and potential biological activities.
  • Chirality: The specific stereochemistry (R and S configurations) indicates that this compound can exist in multiple stereoisomeric forms. Chirality is essential in medicinal chemistry since different enantiomers can exhibit vastly different biological activities.
  • Potential Biological Applications: Due to the presence of hydroxyl groups and complex ring structures, this compound may interact with various biological targets, making it of interest for drug discovery and development.
  • Natural Product Inspiration: The intricate structure is reminiscent of natural products, hinting at potential roles in pharmaceuticals. Many compounds with similar frameworks derived from nature have shown potent anti-inflammatory, antimicrobial, and anticancer properties.
  • Synthesis Challenges: The construction of such a complex compound is not trivial. Synthetic chemists might need to utilize advanced techniques, including asymmetric synthesis and protecting group strategies, to achieve the desired structure.

In conclusion, 1-[(1R,5R,6S,9S,12R)-9,12-dihydroxy-6,16-dimethyl-10,19-dioxa-16-azahexacyclo[12.5.3.15,9.01,14.02,11.06,11]tricosa-2,21-dien-22-yl]ethyl 2-ethyl-4-methyl-1H-pyrrole-3-carboxylate serves as an excellent example of how chemical complexity can lead to expansive research possibilities. As chemists delve into its characteristics, they unlock new avenues for innovation in medicinal applications.

Synonyms
DTXSID40946195
1-(9,12-Dihydroxy-2,11a-dimethyl-1,2,3,4,7a,8,9,10,11,11a,12,13-dodecahydro-7H-9,11b-epoxy-13a,5a-prop[1]enophenanthro[2,1-f][1,4]oxazepin-14-yl)ethyl 2-ethyl-4-methyl-1H-pyrrole-3-carboxylate