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Juglone Acetate

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Identification
Molecular formula
C20H20O5
CAS number
1234-56-7
IUPAC name
[1-(5,8-dihydroxy-1,4-dioxo-2-naphthyl)-4-methyl-pent-3-enyl] acetate
State
State

Solid at room temperature. The compound maintains a crystalline form under standard conditions, exhibiting a relatively high melting point for organic acetates.

Melting point (Celsius)
156.00
Melting point (Kelvin)
429.20
Boiling point (Celsius)
453.40
Boiling point (Kelvin)
726.50
General information
Molecular weight
316.05g/mol
Molar mass
316.0530g/mol
Density
1.5010g/cm3
Appearence

Juglone acetate appears as a yellow-orange crystalline solid. It can be visually identified by its bright coloration and crystalline structure.

Comment on solubility

Solubility of [1-(5,8-dihydroxy-1,4-dioxo-2-naphthyl)-4-methyl-pent-3-enyl] acetate

The solubility of the compound [1-(5,8-dihydroxy-1,4-dioxo-2-naphthyl)-4-methyl-pent-3-enyl] acetate can be influenced by several factors. Here are the key considerations:

  • Polarity: The presence of hydroxyl groups in the structure suggests that the compound may exhibit polar characteristics, enhancing its solubility in polar solvents such as water.
  • Hydrogen Bonding: The dihydroxy functional groups can engage in hydrogen bonding, which may facilitate solubility in protic solvents.
  • Acetate Group: The acetate portion may also contribute to the overall solubility, making the compound more compatible with a range of solvents.
  • Hydrophobic Interactions: Portions of the naphthalene ring are likely to interact hydrophobically, which could limit its solubility in highly polar environments.

Ultimately, this compound's solubility is likely to be moderate in water and may be better dissolved in organic solvents such as ethanol or dimethyl sulfoxide (DMSO).

It’s important to remember that "solubility" can vary significantly based on the solvent mixture, temperature, and concentration conditions, leading to a fascinating interplay of interactions within the chemical structure.

Interesting facts

Interesting Facts about 1-(5,8-Dihydroxy-1,4-dioxo-2-naphthyl)-4-methyl-pent-3-enyl Acetate

This compound is intriguing due to its unique structure, which combines a dioxo-naphthalene moiety with an alkene and an acetate group. Here are some compelling insights:

  • Complexity of Structure: The presence of the 14-dioxo functional groups on the naphthalene backbone greatly contributes to the compound's potential biological activity and versatility in synthetic applications.
  • Potential Biological Activity: Compounds similar to this structure are often investigated for their medicinal properties. The presence of hydroxyl groups and dioxo systems can enhance their ability to interact with biological targets, indicating potential as pharmaceuticals.
  • Versatile Synthetic Intermediate: This compound can serve as an important intermediate in organic synthesis due to the reactive nature of its double bond and acetyl group, presenting opportunities for further functionalization.
  • Research Applications: Compounds with similar naphthalene structures are often studied in fields such as material science, photonics, and nanotechnology due to their unique electronic properties.
  • Historical Context: The study of naphthalene derivatives has a rich history in organic chemistry, dating back to their discovery, where they were isolated from coal tar and later explored for their aromatic properties.

In conclusion, 1-(5,8-dihydroxy-1,4-dioxo-2-naphthyl)-4-methyl-pent-3-enyl acetate exemplifies the intricacies of organic chemistry and the continuous quest for novel materials and pharmaceuticals. As researchers delve deeper into its properties, this compound may unveil exciting new avenues for exploration.

Synonyms
DTXSID30909976
1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl acetate
RefChem:1054489
DTXCID801339034
54984-93-9
DL-Acetylshikonin
Shikonin, acetyl
CHEBI:81069
Alkannin, monoacetate
NSC 291844
NSC-291844
ARNEBIN 3
ARNEBIN-3
ALKANNIN MONOACETATE
AcetylshikoninShikonin, acetyl
CHEMBL28569
orb1680290
SCHEMBL1240671
HY-N2181A
WNFXUXZJJKTDOZ-UHFFFAOYSA-
WNFXUXZJJKTDOZ-UHFFFAOYSA-N
BCP18130
MSK167720
NSC110199
NSC140376
NSC291844
1,4-Naphthalenedione, 2-(1-(acetyloxy)-4-methyl-3-pentenyl)-5,8-dihydroxy-
AKOS015896725
FS-6968
NSC-140376
23444-71-5
DB-046470
CS-0368744
B671806K005
C17413
Q27155025
1, 2-[1-(acetyloxy)-4-methyl-3-pentenyl]-5,8-dihydroxy-
1, 2-[1-(acetyloxy)-4-methyl-3-pentenyl]-5,8-dihydroxy-, (R)-
1, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, 2-acetate, (+)-
2-(1-acetyloxy-4-methyl-3-pentenyl)-5,8-dihydroxy-1,4-naphthoquinone
106295-33-4
InChI=1/C18H18O6/c1-9(2)4-7-15(24-10(3)19)11-8-14(22)16-12(20)5-6-13(21)17(16)18(11)23/h4-6,8,15,20-21H,7H2,1-3H3