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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 5-acetyl-2,4-dimethyl-1H-pyrrole-3-carboxylate
State
State

At room temperature, Tacrolimus is in a solid state. It is typically stored in well-closed containers to protect it from moisture, as it must remain dry for pharmaceutical formulations. The solid nature also facilitates its usage as an active ingredient in topical medications, where it is usually mixed into creams or ointments for application.

Melting point (Celsius)
113.00
Melting point (Kelvin)
386.15
Boiling point (Celsius)
552.00
Boiling point (Kelvin)
825.15
General information
Molecular weight
804.02g/mol
Molar mass
804.0190g/mol
Density
0.9444g/cm3
Appearence

Tacrolimus appears as a white to off-white crystalline powder. It has a consistent fine texture, typically devoid of any visible clumps or unevenness in its structure. The color may vary slightly depending on purity levels but generally remains within the white to off-white spectrum.

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 5-acetyl-2,4-dimethyl-1H-pyrrole-3-carboxylate

This compound presents an intriguing profile regarding its solubility characteristics. Given its complex molecular structure, evaluating its solubility can be a challenge. However, several key points can be noted:

  • Polarity: The presence of multiple hydroxyl (-OH) groups indicates that the compound may exhibit some degree of polarity, which could enhance its solubility in polar solvents such as water.
  • Functional Groups: The incorporation of functional groups like acetyl and pyrrole suggests potential interactions with solvents. Compounds containing aromatic structures usually show varying solubility depending on the solvent matrix.
  • Hydrophobic Regions: The multiple alkyl chains and the overall large steric structure might hinder solubility in non-polar solvents, implying that the compound could be less soluble in organic solvents such as hexane.
  • Solvent Dependency: Expect that solubility could dramatically change based on factors such as temperature, pH, and the specific solvent used.

In conclusion, while predicting the solubility of this compound may require comprehensive experimentation, the structural attributes provide clues about its potential solubility behavior. As a general guideline, it might demonstrate better solubility in polar aprotic solvents while showing limited solubility in non-polar environments. An elaborate study encompassing various solvents is essential to ascertain its precise solubility profile.

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 5-acetyl-2,4-dimethyl-1H-pyrrole-3-carboxylate

This complex organic compound stands out due to its intricate structure and unique properties. Here are some fascinating points about it:

  • Multicyclic Structure: The compound features a hexacyclic framework that interlocks multiple rings, which provides a robust backbone important for stability and reactivity.
  • Chirality: The specified stereochemistry (1R, 5R, 6S, 9S, 12R) indicates the presence of chiral centers, making it a potential candidate for studies in stereochemistry and its implications in biological systems.
  • Hydroxyl Groups: The presence of two hydroxyl (-OH) groups increases the molecule's polarity and can significantly influence its interaction with other biological molecules, potentially enhancing its biological activity.
  • Pyrrole Ring: The pyrrole moiety is known for its presence in many natural products, contributing to the substance's possible pharmacological properties.
  • Acetylation: The acetyl group in this compound could play a critical role in enhancing lipophilicity, potentially improving the compound's absorption and bioavailability in pharmaceutical applications.

In summary, the intricate architecture and functionalized groups of this compound make it a subject of considerable interest in both synthetic and medicinal chemistry. As research continues, it may yield insights into new drug development avenues and the fascinating interplay of complex molecular structures in biological systems.

Synonyms
DTXSID20946198
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 5-acetyl-2,4-dimethyl-1H-pyrrole-3-carboxylate