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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 2,4,5-trimethyl-1H-pyrrole-3-carboxylate
State
State

At room temperature, Tacrolimus is generally found in the solid state as a crystalline powder. It is handled with care to prevent exposure to humidity and moisture.

Melting point (Celsius)
113.00
Melting point (Kelvin)
386.15
Boiling point (Celsius)
394.40
Boiling point (Kelvin)
667.60
General information
Molecular weight
804.02g/mol
Molar mass
804.0190g/mol
Density
0.9125g/cm3
Appearence

Tacrolimus is a white to off-white crystalline powder. It is very hygroscopic, meaning it can easily absorb moisture from the environment. This compound is insoluble in water but soluble in methanol, chloroform, and other organic solvents.

Comment on solubility

Solubility Overview

The 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 2,4,5-trimethyl-1H-pyrrole-3-carboxylate is influenced by several factors:

Key Factors Affecting Solubility:

  • Functional Groups: The presence of hydroxyl groups (-OH) typically enhances solubility in polar solvents like water.
  • Molecular Structure: The intricate structure and the presence of multiple rings may lead to greater hydrophobic characteristics, potentially decreasing solubility.
  • Polarity: The balance between polar and non-polar regions in the molecule will play a critical role in determining its solvability in various solvents.
  • Stereochemistry: The configuration of the molecule, including stereocenters, can affect how the compound interacts with solvent molecules.

In general, one might expect this compound to have limited solubility in non-polar solvents due to its complex architecture, while it may show improved solubility in polar organic solvents.
This is further complicated by its potential ability to form hydrogen bonds, which often increases solubility in aqueous environments. Overall, predicting the exact solubility profile requires comprehensive experimental investigation to account for all these variables.

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 2,4,5-trimethyl-1H-pyrrole-3-carboxylate

This compound is an intriguing example of a complex organic molecule that belongs to the family of alkaloids. Alkaloids are known for their diverse range of biological activities, making them a significant area of research in medicinal chemistry.

Key Features:

  • Complex Structure: The structure includes multiple rings and functional groups, which contribute to its unique properties.
  • Natural Derivation: This compound is often derived from various natural sources, showcasing nature's ability to produce complex chemistries.
  • Pharmaceutical Potential: Its intricate structure suggests potential pharmacological applications, as compounds with such complexity often exhibit bioactivity.
  • Research Opportunities: Investigating this compound’s interactions with biological systems may yield insights into new therapeutic agents.

As a chemistry student, you might find it fascinating to explore the mechanisms of synthesis for such compounds. The various functional groups present, including the dimethyl and polycyclic structures, pose interesting challenges in both organic synthesis and reactivity studies.
Moreover, the relationship between structure and function in these types of compounds emphasizes the importance of stereochemistry. Notably, understanding the stereochemical configurations—like the (1R,5R,6S,9S,12R) designation—can provide crucial insights into their biological actions.
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 2,4,5-trimethyl-1H-pyrrole-3-carboxylate serves as a compelling subject of study in modern chemistry, bridging the gaps between natural product chemistry, pharmacology, and synthetic organic chemistry.

Synonyms
5-Methylbatrachotoxin
BRN 1613226
23509-21-9
Batrachotoxinin A, 20-(2,4,5-trimethylpyrrole-3-carboxylate)
Batrachotoxinin A, 20-(2,4,5-trimetyl-1H-pyrrole-3-carboxylate)
BATRACHOTOXININ A, 20-alpha-(2,4,5-TRIMETHYL-1H-PYRROLE-3-CARBOXYLATE)
RefChem:304253
DTXSID00946196
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 2,4,5-trimethyl-1H-pyrrole-3-carboxylate