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Doxorubicin

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Identification
Molecular formula
C27H29N1O11
CAS number
23214-92-8
IUPAC name
8-[(dimethylamino)methyl]-19-ethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione
State
State

At room temperature, doxorubicin is typically used in a solid form, such as a powder or in a crystalline state. It is often prepared for clinical use as a solution by dissolving it in a suitable solvent.

Melting point (Celsius)
205.00
Melting point (Kelvin)
478.00
Boiling point (Celsius)
0.00
Boiling point (Kelvin)
0.00
General information
Molecular weight
543.52g/mol
Molar mass
543.5200g/mol
Density
1.5960g/cm3
Appearence

Doxorubicin appears as a red-orange crystalline solid. It is often supplied as the hydrochloride salt, which is a red-orange to red-brown powder.

Comment on solubility

Solubility of 8-[(dimethylamino)methyl]-19-ethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione

The solubility of the compound C27H29N1O11 can be significantly influenced by its structural composition and functional groups. Here are some key points about its solubility:

  • Polar Functional Groups: The presence of hydroxyl groups (-OH) enhances solubility in polar solvents such as water.
  • Large Hydrocarbon Regions: The extensive hydrocarbon sections may limit solubility in highly polar environments, promoting better solubility in organic solvents like ethanol or dichloromethane.
  • Dimethylamino Group: This group may contribute to the amphiphilic nature of the compound, rendering it soluble in both polar and non-polar solvents under certain conditions.
  • Temperature Dependency: As with many compounds, solubility may increase with temperature, allowing for a broader range of solvent behaviors.

Overall, it's essential to test solubility in various solvents to fully understand the behavior of this complex molecule. As the saying goes, "Like dissolves like," making it crucial to consider both polar and non-polar solvents when evaluating solubility.

Interesting facts

Interesting Facts About 8-[(Dimethylamino)methyl]-19-ethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione

This compound, characterized by its complex molecular structure, is a fascinating subject in the field of organic chemistry. Here are some noteworthy points:

  • Multiplicity of Rings: This compound contains an intricate network of five interconnected ring systems, which is a hallmark of natural alkaloids.
  • Substituents: The presence of both dimethylamino and ethyl groups contributes to its unique properties and may influence its biological activity.
  • Hydroxyl Groups: The two hydroxyl groups can play a critical role in the compound's reactivity and solubility, as they often engage in hydrogen bonding.
  • Applications: Compounds with similar architectures are often investigated for their therapeutic potentials, including anti-cancer and anti-inflammatory properties.
  • Research Interest: Scientists are intrigued by compounds featuring diazacyclic structures due to their unique interactions in biological systems.
  • Quote from a Chemist: "The real beauty of organic synthesis lies in the creativity of crafting such complex molecules, which can unlock new pathways in medicinal chemistry."

This compound exemplifies the diversity and intricacy found in organic compounds. Its structural features not only present challenges in synthesis but also open avenues for potential pharmacological applications, making it a prime candidate for further study.

Synonyms
hycamptamine hydrochloride hydrate
8-[(dimethylamino)methyl]-19-ethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione
MFCD00870670
Neuro_000236
10-[(Dimethylamino)methyl]-4-ethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
CHEMBL305801
SCHEMBL5531617
CHEBI:93785
DTXSID60861255
UCFGDBYHRUNTLO-UHFFFAOYSA-N
BCP08995
LSM-4296
NSC-609669 hydrochloride hydrate
URB90410
XWC98573
SKF-104864A hydrochloride hydrate
AKOS015894855
DB-015058
BRD-A59985574-003-01-9
Q27165487
NSC 609699 NSC-609699 NSC609699
9-[(dimethylamino)methyl]-10-hydroxy-(20S)-camptothecin hydrochloride hydrate
10-[(Dimethylamino)methyl]-4-ethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione #