Skip to main content

Plumbagin

ADVERTISEMENT
Identification
Molecular formula
C11H8O3
CAS number
481-42-5
IUPAC name
5,8-dihydroxy-2-(1-hydroxy-4-methyl-pent-3-enyl)naphthalene-1,4-dione
State
State

Plumbagin is a solid at room temperature, appearing as a crystalline powder.

Melting point (Celsius)
78.00
Melting point (Kelvin)
351.15
Boiling point (Celsius)
356.70
Boiling point (Kelvin)
629.85
General information
Molecular weight
188.18g/mol
Molar mass
188.1830g/mol
Density
1.4950g/cm3
Appearence

Plumbagin appears as yellow crystalline needles or a yellow powder.

Comment on solubility

Solubility of 5,8-dihydroxy-2-(1-hydroxy-4-methyl-pent-3-enyl)naphthalene-1,4-dione

The compound 5,8-dihydroxy-2-(1-hydroxy-4-methyl-pent-3-enyl)naphthalene-1,4-dione, with the chemical formula C11H8O3, exhibits interesting solubility characteristics that can be summarized as follows:

  • Aqueous Solubility: This compound is generally expected to have limited solubility in water due to its hydrophobic naphthalene ring structure.
  • Solvent Compatibility: It is likely to be more soluble in organic solvents such as ethanol, methanol, or DMSO due to the presence of hydroxyl (-OH) groups that can interact favorably with polar solvents.
  • Temperature Effects: Like many organic compounds, solubility may increase with temperature, which can promote better interactions with solvents.
  • pH Influence: The solubility can also be affected by the pH of the solution, particularly as the compound contains multiple hydroxyl groups that can either donate or accept protons.

In summary, while 5,8-dihydroxy-2-(1-hydroxy-4-methyl-pent-3-enyl)naphthalene-1,4-dione may not be highly soluble in water, its compatibility with organic solvents and the influence of external factors such as temperature and pH highlight the complexity of its solubility characteristics.

Interesting facts

Interesting Facts about 5,8-Dihydroxy-2-(1-hydroxy-4-methyl-pent-3-enyl)naphthalene-1,4-dione

This fascinating compound, often referred to in studies related to organic chemistry and medicinal applications, showcases the intricate relationship between molecular structure and biological activity. Here are some notable insights:

  • Natural Origin: This compound is structurally related to naturally occurring compounds found in various plant species, particularly those with medicinal properties. Its unique structure allows it to exhibit a variety of biological activities.
  • Health Implications: Research indicates that compounds with similar structures may possess antioxidant and anti-inflammatory properties, which could be beneficial in developing treatments for various diseases.
  • Structure-Activity Relationship: The specific arrangement of functional groups in 5,8-dihydroxy-2-(1-hydroxy-4-methyl-pent-3-enyl)naphthalene-1,4-dione greatly influences its chemical properties. Understanding these relationships is crucial for medicinal chemistry and drug design.
  • Synthetic Routes: Chemists are interested in synthesizing this compound due to its complex nature, which involves multiple steps and conditions, highlighting the ingenuity required in organic synthesis.
  • Research Potential: The compound is a promising candidate for further research in various fields, including pharmacology and biochemistry, providing opportunities for significant discoveries in medicine and health.

As a student of chemistry, one can appreciate how compounds like this serve as a bridge between natural compounds and synthetic chemistry. The exploration of such complex structures not only enhances our understanding of molecular interactions but also paves the way for innovative solutions in medicinal fields.

Synonyms
54952-43-1
SHIKALKIN
C.I. Natural Red 20
(+-)-Shikonin
(+/-)-Alkannin
(+/-)-Shikonin
5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl)naphthalene-1,4-dione
ARNEBIN-4
(Rac)-Shikonin
Shikonine
23444-65-7
NSC94524
(+)-Shikonin
MFCD00016668
NSC252844
NSC407295
5,8-DIHYDROXY-2-(1-HYDROXY-4-METHYLPENT-3-EN-1-YL)NAPHTHALENE-1,4-DIONE
C.I. 75530
5,8-Dihydroxy-6-(1-hydroxy-4-methylpent-3-en-1-yl)naphthalene-1,4-dione
1,4-Naphthalenedione, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)- (9CI)
11019-15-1
(+-)-Alkannin
C.I. 75535
C.I. 75535;Isoarnebin 4
C.I. Natural Red 20 (VAN)
1, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, (S)-
1, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, (-)-
1, 5,8-dihydroxy-6-(1-hydroxy-4-methyl-3-pentenyl)-, (-)-
NSC-252844
natural red 20
Shikonin (7b)
(+-)-Shikalkin
NSC 291845
ALKANNIN, 1-
KBioGR_000610
KBioSS_000610
CHEMBL29285
SCHEMBL3182028
Shikonin, >=98% (HPLC)
SCHEMBL14305203
KBio2_000610
KBio2_003178
KBio2_005746
KBio3_001079
KBio3_001080
NEZONWMXZKDMKF-UHFFFAOYSA-
CHEBI:174748
BDBM178090
Bio2_000475
Bio2_000955
HMS1362P11
BCP29329
BCP34282
ECA95243
HY-N6004
NSC291845
1,4-Naphthalenedione, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-
5,8-dihydroxy-2-(1-hydroxy-4-methyl-pent-3-enyl)naphthalene-1,4-dione
AKOS016034343
NSC-291845
NSC-407295
IDI1_002230
QTL1_000075
SMP2_000188
85251-58-7
DA-67567
LS-14485
NCI60_002031
DB-082640
CS-0032051
H1780
NS00018361
NS00123717
(-)-Shikonin;C.I. 75535; Isoarnebin 4
1, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-
1, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, (R)-
1, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, (+)-
5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-1,4-naphthoquinone
(+/-)-5,8-Dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-1,4-naphthoquinone
InChI=1/C16H16O5/c1-8(2)3-4-10(17)9-7-13(20)14-11(18)5-6-12(19)15(14)16(9)21/h3,5-7,10,17-19H,4H2,1-2H3