Ilimaquinone

Modify Date: 2024-01-10 07:51:07

Ilimaquinone Structure
Ilimaquinone structure
Common Name Ilimaquinone
CAS Number 71678-03-0 Molecular Weight 358.471
Density 1.1±0.1 g/cm3 Boiling Point 478.4±45.0 °C at 760 mmHg
Molecular Formula C22H30O4 Melting Point N/A
MSDS N/A Flash Point 159.9±22.2 °C

 Use of Ilimaquinone


Ilimaquinone, a marine sponge metabolite, displays anticancer activity via GADD153-mediated pathway. Ilimaquinone can induce vesiculation of the Golgi apparatus[1]. Ilimaquinone exerts anti-HIV, anti-microbial, anti-inflammatory, and effects[2].

 Names

Name 3-[[(1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]methyl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione
Synonym More Synonyms

 Ilimaquinone Biological Activity

Description Ilimaquinone, a marine sponge metabolite, displays anticancer activity via GADD153-mediated pathway. Ilimaquinone can induce vesiculation of the Golgi apparatus[1]. Ilimaquinone exerts anti-HIV, anti-microbial, anti-inflammatory, and effects[2].
Related Catalog
In Vitro Ilimaquinone induces a concentration-dependent anti-proliferative effect in several types of cancer cell lines, including prostate cancer PC-3 and LNCaP, non-small cell lung cancer A549 and hepatocellular carcinoma Hep3B cells. Ilimaquinone (0.3-30 μM; 48 hours) inhibits the proliferation of PC-3 cells, DU145, LNCaP, MG63, A549, Hep3B cells with GI50s of 2.6 μM, 5.8, 4.6, 4.9, 4.1, 12.0μM, respectively[1]. Cell Viability Assay[1] Cell Line: Prostate cancer PC-3 cells Concentration: 0.3, 1, 3, 10, and 30 μM Incubation Time: 48 hours Result: Inhibited the proliferation of PC-3 cells in a concentration-dependent manner.
In Vivo Ilimaquinone exhibits terminal elimination half-lives (T1/2=1.2±0.3 h) due to high plasma clearance (2.95±0.53 L/h/kg) following oral administration (10 mg/kg) in male Sprague-Dawley rats[2].
References

[1]. Pin-Hsuan Lu, et al. Ilimaquinone, a Marine Sponge Metabolite, Displays Anticancer Activity via GADD153-mediated Pathway. Eur J Pharmacol. 2007 Feb 5;556(1-3):45-54.

[2]. Heebin Son, et al. Stereo-Selective Pharmacokinetics of Ilimaquinone Epimers Extracted From a Marine Sponge in Rats. Mar Drugs. 2019 Mar 17;17(3):171.

 Chemical & Physical Properties

Density 1.1±0.1 g/cm3
Boiling Point 478.4±45.0 °C at 760 mmHg
Molecular Formula C22H30O4
Molecular Weight 358.471
Flash Point 159.9±22.2 °C
Exact Mass 358.214417
PSA 63.60000
LogP 6.38
Vapour Pressure 0.0±2.7 mmHg at 25°C
Index of Refraction 1.549

 Safety Information

WGK Germany 3

 Synthetic Route

 Synonyms

2-Hydroxy-5-methoxy-3-{[(1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-methylenedecahydro-1-naphthalenyl]methyl}-1,4-benzoquinone
Illimaquinone
Ilimaquinone
Imaquinone
2-hydroxy-5-methoxy-3-{[(1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-methylidenedecahydronaphthalen-1-yl]methyl}cyclohexa-2,5-diene-1,4-dione
MFCD00274432
2,5-Cyclohexadiene-1,4-dione, 3-[[(1R,2S,4aS,8aS)-decahydro-1,2,4a-trimethyl-5-methylene-1-naphthalenyl]methyl]-2-hydroxy-5-methoxy-