Rapamycin (Sirolimus) | Solubility of Things

Identification

Molecular formula

C₅₁H₇₉NO₁₃

CAS number

53123-88-9

IUPAC name

4-[[15-[carboxy(hydroxy)methyl]-20,26,30,32-tetrahydroxy-18,21,25,27,29,31,36-heptamethyl-13,16-dioxo-19-[[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]-17,38-dioxa-14-azabicyclo[32.3.1]octatriaconta-3,5,9,11,24,28-hexaen-22-yl]oxy]-2-hydroxy-4-oxo-butanoic acid

State

Rapamycin is a solid at room temperature. Due to its low solubility in water, it is often used in a brightly colored formulated powder or in a solution form for pharmaceutical applications.

Melting point (Celsius)

183.00

Melting point (Kelvin)

456.20

Boiling point (Celsius)

817.50

Boiling point (Kelvin)

1 090.50

General information

Molecular weight

914.17g/mol

Molar mass

914.1710g/mol

Density

0.9639g/cm³

Appearence

Sirolimus, also known as Rapamycin, typically appears as a white to off-white powder. Its crystalline form is highly hydrophobic, making it poorly soluble in water but more soluble in organic solvents such as ethanol and DMSO (dimethyl sulfoxide).

Comment on solubility

Solubility of 4-[[15-[carboxy(hydroxy)methyl]-20,26,30,32-tetrahydroxy-18,21,25,27,29,31,36-heptamethyl-13,16-dioxo-19-[[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]-17,38-dioxa-14-azabicyclo[32.3.1]octatriaconta-3,5,9,11,24,28-hexaen-22-yl]oxy]-2-hydroxy-4-oxo-butanoic acid

The solubility of the compound C₅₁H₇₉NO₁₃, which has an intricate structure with multiple functional groups, can be influenced by several factors:

Polarity: The presence of numerous hydroxyl (–OH) and carboxylic acid (–COOH) groups suggests a high degree of polarity. This typically enhances solubility in polar solvents like water.
Molecular Size: The large molecular weight and size of the compound could hinder its solubility in smaller organic solvents despite its polar functional groups.
Hydrogen Bonding: The ability of the –OH and –COOH groups to form hydrogen bonds with solvent molecules plays a crucial role in solubility. More hydrogen bonds generally mean better solubility.
pH Sensitivity: Being a carboxylic acid, its solubility may also be pH-dependent, increasing in more alkaline solutions where the acid can ionize.

In conclusion, while the compound may exhibit reasonable solubility in polar solvents due to its functional groups, the complex structure and large molecular size could present challenges in various solvent environments. Therefore, thorough solubility testing is recommended to fully understand its behavior in different conditions.

Interesting facts

Interesting Facts about 4-[[15-[carboxy(hydroxy)methyl]-20,26,30,32-tetrahydroxy-18,21,25,27,29,31,36-heptamethyl-13,16-dioxo-19-[[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]-17,38-dioxa-14-azabicyclo[32.3.1]octatriaconta-3,5,9,11,24,28-hexaen-22-yl]oxy]-2-hydroxy-4-oxo-butanoic acid

This compound, a complex organic molecule, has intrigued chemists due to its remarkable structure and potential applications. Here are some intriguing aspects:

Structural Complexity: The compound features an extensive framework comprising multiple functional groups and intricate stereochemistry. This complexity showcases the diversity of organic synthesis.
Biological Activity: Many compounds with similar structures exhibit significant biological properties, including antimicrobial and anti-inflammatory effects. This raises questions about the pharmacological potential of this compound.
Synthetic Challenges: The synthesis of such a compound often requires advanced techniques in organic chemistry, including multiple steps of functionalization and protection strategies. Chemists continually strive to improve yields and reduce environmental impact during synthesis.
Applications in Drug Development: Compounds with sophisticated architectures often serve as lead compounds for drug design. Researchers might explore derivatives of this molecule to enhance efficacy and reduce side effects.
Structure-Activity Relationship: Investigating how structural changes affect biological activity is crucial. By modifying parts of this compound, scientists can potentially discover new therapeutic agents.

As one dives deeper into the world of organic compounds, this molecule stands as a testament to the beauty and complexity of chemical diversity. The quote from Henri Poincaré resonates here: "Mathematics is the art of giving the same name to different things." In the realm of chemistry, understanding and categorizing complexity also reflects our ingenuity and curiosity about nature.