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Tacrolimus

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Identification
Molecular formula
C44H69NO12
CAS number
104987-11-3
IUPAC name
4-[[15-[carboxy(hydroxy)methyl]-24,28,30-trihydroxy-18-[2-hydroxy-1-[[3,7,11,13-tetrahydroxy-12-[(7-hydroxy-9-methoxy-4,4,6,8,8-pentamethyl-5,9-dioxo-non-2-enoyl)amino]-2,6,8,10,14-pentamethyl-pentadec-8-enoyl]amino]propyl]-19,23,25,27,29,34-hexamethyl-13,16-dioxo-17,36-dioxa-14-azabicyclo[30.3.1]hexatriaconta-3,5,9,11,22,26-hexaen-20-yl]oxy]-2-hydroxy-4-oxo-butanoic acid
State
State

At room temperature, Tacrolimus is typically in a solid state as a crystalline powder. It is usually handled in this form for medical use, particularly in the preparation of topical and oral formulations to aid in its delivery and efficacy as an immunosuppressant. It is crucial to handle it with care to avoid moisture and maintain its stability.

Melting point (Celsius)
113.30
Melting point (Kelvin)
386.45
Boiling point (Celsius)
305.00
Boiling point (Kelvin)
578.00
General information
Molecular weight
804.02g/mol
Molar mass
804.0190g/mol
Density
1.2000g/cm3
Appearence

Tacrolimus appears as a white to off-white crystalline powder. Due to its properties as an immunosuppressive drug, it is often provided in a powder form to be used in formulations. It is not highly soluble in water and has a very specific crystalline structure.

Comment on solubility

Solubility Profile of 4-[[15-[carboxy(hydroxy)methyl]-24,28,30-trihydroxy-18-[2-hydroxy-1-[[3,7,11,13-tetrahydroxy-12-[(7-hydroxy-9-methoxy-4,4,6,8,8-pentamethyl-5,9-dioxo-non-2-enoyl)amino]-2,6,8,10,14-pentamethyl-pentadec-8-enoyl]amino]propyl]-19,23,25,27,29,34-hexamethyl-13,16-dioxo-17,36-dioxa-14-azabicyclo[30.3.1]hexatriaconta-3,5,9,11,22,26-hexaen-20-yl]oxy]-2-hydroxy-4-oxo-butanoic acid

The solubility of 4-[[15-[carboxy(hydroxy)methyl]-24,28,30-trihydroxy-18-[2-hydroxy-1-[[3,7,11,13-tetrahydroxy-12-[(7-hydroxy-9-methoxy-4,4,6,8,8-pentamethyl-5,9-dioxo-non-2-enoyl)amino]-2,6,8,10,14-pentamethyl-pentadec-8-enoyl]amino]propyl]-19,23,25,27,29,34-hexamethyl-13,16-dioxo-17,36-dioxa-14-azabicyclo[30.3.1]hexatriaconta-3,5,9,11,22,26-hexaen-20-yl]oxy]-2-hydroxy-4-oxo-butanoic acid (C44H69NO12) can be characterized as follows:

  • Polarity: The presence of multiple hydroxyl (-OH) and carboxyl (-COOH) groups indicates that this compound is likely to be polar, which ordinarily enhances solubility in polar solvents.
  • Solvent Compatibility: It is primarily expected to be soluble in:
    • Water
    • Alcohols (such as methanol and ethanol)
  • Solvent Limitations: However, the extensive non-polar hydrocarbon chain may hinder solubility in non-polar solvents like hexane or benzene.

As a general rule, polar compounds showcase better solubility in polar solvents and vice versa; thus, the unique structure of this compound suggests a complex interaction with solvents. As stated, "like dissolves like," making it essential to understand both the polar and non-polar characteristics of such extensive molecular structures.

Interesting facts

Interesting Facts about 4-[[15-[carboxy(hydroxy)methyl]-24,28,30-trihydroxy-18-[2-hydroxy-1-[[3,7,11,13-tetrahydroxy-12-[(7-hydroxy-9-methoxy-4,4,6,8,8-pentamethyl-5,9-dioxo-non-2-enoyl)amino]-2,6,8,10,14-pentamethyl-pentadec-8-enoyl]amino]propyl]-19,23,25,27,29,34-hexamethyl-13,16-dioxo-17,36-dioxa-14-azabicyclo[30.3.1]hexatriaconta-3,5,9,11,22,26-hexaen-20-yl]oxy]-2-hydroxy-4-oxo-butanoic acid

This compound is a striking example of complex organic chemistry, representing a meticulously detailed structure belonging to the class of natural products. Here are some intriguing aspects to consider:

  • Structural Complexity: The compound showcases an elaborate framework consisting of multiple functional groups, a variety of hydroxyl (-OH) groups, and intricate hydrocarbon chains. This structural complexity is not merely aesthetic; it plays a crucial role in how the compound interacts biologically.
  • Potential Applications: Due to its rich functionality, this compound might exhibit interesting pharmacological properties. Compounds with numerous hydroxyl groups often function as powerful antioxidants, which can combat oxidative stress and improve health outcomes.
  • Origin of Name: The nomenclature itself is indicative of the compound's structural intricacies, which include various substituents and modifications aimed at enhancing its biological activity. This serves as a reminder of how naming in chemistry can reflect the underlying science.
  • Synthetic Challenges: The synthesis of such complex molecules typically requires advanced synthetic techniques, including multi-step reactions and possibly the use of protecting groups to ensure that certain functional groups do not react undesirably during the synthesis process.
  • Research Interest: Compounds of this nature often attract considerable attention in research settings, particularly in medicinal chemistry, due to their varying degrees of bioactivity and potential therapeutic applications.

The exploration of such complex organic compounds not only deepens our understanding of chemical reactivity and structure-function relationships but also opens new avenues for discovering novel therapeutic agents.