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Epirubicin

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Identification
Molecular formula
C27H29NO11
CAS number
56420-45-2
IUPAC name
1-[(2S)-6-[(6S)-5-(1-acetoxyethyl)-1,6-dihydroxy-6-methyl-8,9,10-trioxo-5,7-dihydroanthracen-2-yl]-2,5-dihydroxy-2-methyl-4,9,10-trioxo-1,3-dihydroanthracen-1-yl]ethyl acetate
State
State

At room temperature, epirubicin is a solid in its most stable form. When used in pharmaceutical preparations, it is often in the form of its hydrochloride salt, which is soluble in water, forming orange-red solutions.

Melting point (Celsius)
207.00
Melting point (Kelvin)
480.15
Boiling point (Celsius)
290.00
Boiling point (Kelvin)
563.15
General information
Molecular weight
543.52g/mol
Molar mass
579.5610g/mol
Density
1.2890g/cm3
Appearence

Epirubicin appears as a red-orange crystalline solid. It is typically available as a hydrochloride salt, forming orange-red solutions when dissolved in water.

Comment on solubility

Solubility of 1-[(2S)-6-[(6S)-5-(1-acetoxyethyl)-1,6-dihydroxy-6-methyl-8,9,10-trioxo-5,7-dihydroanthracen-2-yl]-2,5-dihydroxy-2-methyl-4,9,10-trioxo-1,3-dihydroanthracen-1-yl]ethyl acetate

The solubility of 1-[(2S)-6-[(6S)-5-(1-acetoxyethyl)-1,6-dihydroxy-6-methyl-8,9,10-trioxo-5,7-dihydroanthracen-2-yl]-2,5-dihydroxy-2-methyl-4,9,10-trioxo-1,3-dihydroanthracen-1-yl]ethyl acetate can be assessed based on its complex structure and functional groups.

Generally, solubility is influenced by several factors:

  • Polarity: The presence of hydroxyl groups (–OH) typically increases solubility in polar solvents, such as water. However, the tricyclic structure may introduce hydrophobic characteristics.
  • Functional Groups: The presence of acetate and multiple hydroxyl groups suggest potential hydrogen bonding, which can enhance solubility in polar solvents.
  • Steric Hindrance: The large size and spatial configuration of the compound could impede its ability to solvate in solution, affecting overall solubility.

In summary, it is likely that:

  • This compound exhibits limited solubility in water
  • It may demonstrate higher solubility in organic solvents such as ethanol or acetone.

As always, experimental data should be referenced for precise solubility values, as predictions can be challenging given the intricate structure of this compound. “Solubility is a complex balance of forces and interactions.”

Interesting facts

Interesting Facts about 1-[(2S)-6-[(6S)-5-(1-acetoxyethyl)-1,6-dihydroxy-6-methyl-8,9,10-trioxo-5,7-dihydroanthracen-2-yl]-2,5-dihydroxy-2-methyl-4,9,10-trioxo-1,3-dihydroanthracen-1-yl]ethyl acetate

This compound, with its intricate structure, belongs to the family of anthraquinones, which are well-known for their diverse applications in various fields. Here are some fascinating insights:

  • Biological Significance: Anthraquinones, including this compound, are famous for their biological activities, displaying antitumor, antimalarial, and antimicrobial properties. Research continues to investigate their potential as therapeutic agents.
  • Role in Coloration: These compounds are also instrumental in dyeing and pigment industries, providing vivid colors due to their conjugated structures, which allow them to absorb light efficiently.
  • Complexity of Structure: The presence of multiple hydroxyl groups and acetyl functionalities in its architecture makes this compound highly versatile. Such structural features enhance its reactivity, allowing it to partake in various chemical transformations.
  • Natural Occurrence: Many anthraquinones are derived from natural sources, including plants and fungi, and serve essential roles in plant defense mechanisms or come as secondary metabolites.
  • Research Focus: Current studies are focused on synthesizing derivatives of anthraquinones to improve their efficacy as pharmaceuticals, showcasing the influence of modification on biological activity.

As a chemistry enthusiast or student, the exploration of such a complex compound serves as a reminder of the intricate relationships between structure and function in organic chemistry. The continual research on anthraquinones emphasizes the importance of synthetic flexibility in developing new compounds with improved properties.

Synonyms
Julimycin B2
1-[(2S)-6-[(6S)-5-(1-acetyloxyethyl)-1,6-dihydroxy-6-methyl-8,9,10-trioxo-5,7-dihydroanthracen-2-yl]-2,5-dihydroxy-2-methyl-4,9,10-trioxo-1,3-dihydroanthracen-1-yl]ethyl acetate
1-((2S)-6-((6S)-5-(1-acetyloxyethyl)-1,6-dihydroxy-6-methyl-8,9,10-trioxo-5,7-dihydroanthracen-2-yl)-2,5-dihydroxy-2-methyl-4,9,10-trioxo-1,3-dihydroanthracen-1-yl)ethyl acetate
18126-05-1
Julimycin B-II
JULIMYCIN B2-CA
Julimycin B2, calcium salt
Julimycin II
Julichrome Q, 11,11'-diacetate
NSC 248605
BRN 2688327
(2,2'-Bianthracene)-8,8',9,9',10,10'(5H,5'H)-hexone, 6,6',7,7'-tetrahydro-1,1',6-beta,6'-beta-tetrahydroxy-5-beta,5'-beta-bis(1-hydroxyethyl)-6,6'-dimethyl-,5,5'-diacetate
SCHEMBL30260534