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Adriamycin

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Identification
Molecular formula
C27H29NO11
CAS number
25316-40-9
IUPAC name
4-[3-amino-2,6-dihydroxy-5-(methylamino)cyclohexoxy]-6'-(1-amino-2-hydroxy-ethyl)-6-(hydroxymethyl)spiro[4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-2,2'-tetrahydropyran]-3',4',5',7-tetrol
State
State

Adriamycin is typically used as a lyophilized (freeze-dried) powder for solution, which is reconstituted in a liquid environment for medical applications. In its pure form, it is a crystalline solid.

Melting point (Celsius)
203.00
Melting point (Kelvin)
476.15
Boiling point (Celsius)
507.10
Boiling point (Kelvin)
780.10
General information
Molecular weight
543.53g/mol
Molar mass
543.5250g/mol
Density
1.6000g/cm3
Appearence

Adriamycin typically appears as a red to orange-red crystalline powder. It is known for its intensely colored solution when dissolved, often used as a red-orange solution in its medicinal form.

Comment on solubility

Solubility of 4-[3-amino-2,6-dihydroxy-5-(methylamino)cyclohexoxy]-6'-(1-amino-2-hydroxy-ethyl)-6-(hydroxymethyl)spiro[4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-2,2'-tetrahydropyran]-3',4',5',7-tetrol (C27H29NO11)

The solubility of this compound is influenced by its complex structure and the presence of multiple functional groups. Here are some key points regarding its solubility:

  • Hydrophilic Characteristics: The compound contains multiple hydroxy (-OH) groups, which tend to enhance its solubility in polar solvents such as water.
  • Potential for Hydrogen Bonding: The amino and hydroxyl groups can engage in hydrogen bonding, potentially increasing solubility in aqueous environments.
  • Structural Complexity: The spiro and tetrahydro features may restrict its ability to dissolve uniformly, possibly leading to varying solubility profiles depending on the solvent.
  • Solvent Specificity: While water may serve as a good solvent due to polarity, organic solvents might also dissolve the compound selectively, depending on their chemical nature.

It is often stated that the solubility of complex organic compounds can vary significantly: "No compound is universally soluble in all solvents." Therefore, experimental determinations under various conditions are generally required to fully understand the solubility behavior of this multifaceted compound.

Interesting facts

Interesting Facts about 4-[3-amino-2,6-dihydroxy-5-(methylamino)cyclohexoxy]-6'-(1-amino-2-hydroxy-ethyl)-6-(hydroxymethyl)spiro[4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-2,2'-tetrahydropyran]-3',4',5',7-tetrol

This compound is quite fascinating due to its complex structure and potential implications in various fields of study! Here are some engaging points to consider:

  • Structural Diversity: The intricate arrangement of its multiple functional groups contributes to its unique reactivity and interactions with biological systems. The presence of both amino and hydroxyl groups suggests possible pharmacological properties.
  • Potential Biological Activity: Compounds like this often show activity as enzyme inhibitors, signaling molecules, or even as therapeutic agents. Understanding their mechanisms could unlock new treatments for various diseases.
  • Spirocyclic Structures: The spiro[4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran] motif adds to the intrigue, as spiro compounds have been widely investigated for their diverse biological activities, including anticancer, antibacterial, and anti-inflammatory effects.
  • Complexity in Synthesis: The synthesis of such complex molecules requires advanced techniques and methodologies, often involving multiple steps and careful planning, showcasing the artistry of organic synthesis.

To quote a renowned scientist in the field, "The beauty of chemistry lies in the infinite combinations of elements and compounds." This sentiment resonates especially well with this compound due to its multifaceted nature and the promising research avenues it may lead to.

In summary, 4-[3-amino-2,6-dihydroxy-5-(methylamino)cyclohexoxy]-6'-(1-amino-2-hydroxy-ethyl)-6-(hydroxymethyl)spiro[4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-2,2'-tetrahydropyran]-3',4',5',7-tetrol is not only a chemical curiosity but also a potential source of scientific innovation and discovery!

Synonyms
hygromycin b
Destomycin A
31282-04-9
Destomysin
Hygrovectine
Hygrovetine
Hydromycin B
Antibiotic A-396-II
14918-35-5
Hyanthelmix
Hygromycin B from Streptomyces hygroscopicus
CID 23777801
CHEBI:4454
SCHEMBL18763320
DTXSID50860459
D-Streptamine, O-6-amino-6-deoxy-L-glycero-D-galacto-heptopyranosylidene-(1.fwdarw.2-3)-O-.beta.-D-talopyranosyl-(1.fwdarw.5)-2-deoxy-N1-methyl-
4-[3-amino-2,6-dihydroxy-5-(methylamino)cyclohexyl]oxy-6'-(1-amino-2-hydroxyethyl)-6-(hydroxymethyl)spiro[4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-2,2'-oxane]-3',4',5',7-tetrol
DB-068433
Hygromycin B from Streptomyces hygroscopicus powder
Q27106388
4-{[3-Amino-2,6-dihydroxy-5-(methylamino)cyclohexyl]oxy}-6'-(1-amino-2-hydroxyethyl)-6-(hydroxymethyl)tetrahydro-4H-spiro[1,3-dioxolo[4,5-c]pyran-2,2'-oxane]-3',4',5',7-tetrol
D-Stretamine,3-O-[6-(1-amino-2-hydroxyethyl)tetrahydro-3,4,5-trihydroxy-2H-pyran-2-ylidene)-.beta.-D-talopyranosyl]-2-deoxy-N(sup3)methyl-