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044951 Ilimaquinone CAS: 71678-03-0

Specifications
References
CAS Number
71678-03-0
Grade
Highly Purified
MDL Number
MFCD00274432
Molecular Formula
C22H30O4
Molecular Weight
358.5
EU Commodity Code
38220090
Shipping Temp
RT
Storage Temp
4°C/-20°C

Cytoplasmic microtubule inhibitor. Cell permeable, antimicrobial, anti-inflammatory, antimitotic and cytotoxic compound. Induces a complete and reversible breakdown/disruption of Golgi membranes into smaller vesicular structures. Blocks the association of the ADP-ribosylation factor and beta-COP to the Golgi membrane. Blocks protein transport to the plasma membrane and inhibits gap junctional communication. HIV-1 inhibitor. Blocks the cytotoxicity of ricin and diphtheria toxin. S-Adenosylhomocysteinase hydrolase inhibitor and cellular methylations inhibitor. DNA polymerase beta lyase activity inhibitor. Anti-cancer compound.

Source
Isolated from Anthelia sp.
Synonyms
3-[(Decahydro-1α,2β,4aβ-trimethyl-5-methylene-1-naphthyl)methyl]-2-hydroxy-5-methoxybenzoquinone; IQ
CAS Number
71678-03-0
Molecular Weight
358.5
Molecular Formula
C22H30O4
Solubility
Methanol, ethanol, DMSO or hexane
Appearance
Supplied as a yellow solid.
Method for Determining Identity
Proton NMR and MS
Purity
≥98% (HPLC)
Storage and Stability
May be stored at 4°C for short-term only. Stable for 12 months after receipt when stored at -20°C. For maximum recovery of product, centrifuge the original vial prior to removing the cap.
Important Note
This product as supplied is intended for research use only, not for use in human, therapeutic or diagnostic applications without the expressed written authorization of United States Biological.
Toxicity and Hazards
 All products should be handled by qualified personnel only, trained in laboratory procedures.
References
1. Ilimaquinone, a sesquiterpenoid quinone from a marine sponge: R.T. Luibrand, et al.; Tetrahedron 35, 609 (1979)|2. Microtubule independent vesiculation of Golgi membranes and the reassembly of vesicles into Golgi stacks: B. Veit, et al.; J. Cell. Biol. 122, 1197 (1993)|3. Complete vesiculation of Golgi membranes and inhibition of protein transport by a novel sea sponge metabolite, ilimaquinone: P.A. Takizawa, et al.; Cell 73, 1079 (1993)|4. The interaction of illimaquinone, a selective inhibitor of the RNase H activity, with the reverse transcriptases of human immunodeficiency and murine leukemia retroviruses: S. Loya & A. Hizi; J. Biol. Chem. 268, 9323 (1993)|5. Ilimaquinone inhibits the cytotoxicities of ricin, diphtheria toxin, and other protein toxins in Vero cells: M.P. Nambiar & H.C. Wu; Exp. Cell Res. 219, 671 (1995)|6. Golgi-disturbing agents: A. Dinter & E.G. Berger; Histochem. Cell Biol. 109, 571 (1998)|7. Interactions of (-)-ilimaquinone with methylation enzymes: implications for vesicular-mediated secretion: H.S. Radeke, et al.; Chem. Biol. 6, 639 (1999)|8. Marine sesquiterpenoids that inhibit the lyase activity of DNA polymerase beta: S. Cao, et al.; J. Nat. Prod. 67, 1716 (2004)|9. Ilimaquinone inhibits gap junctional communication in a connexin isotype-specific manner: V. Cruciani & S.O. Mikalsen; Exp. Cell Res. 304, 136 (2005)|10. Ilimaquinone, a marine sponge metabolite, displays anticancer activity via GADD153-mediated pathway: P.H. Lu, et al.; Eur. J. Pharmacol. 556, 45 (2007)|11. Comparison of the biological properties of several marine sponge-derived sesquiterpenoid quinones: C.A. Motti, et al.; Molecules 12, 1376 (2007)|12. A new structural class of S-adenosylhomocysteine hydrolase inhibitors: B.G. Kim, et al.; Bioorg. Med. Chem. 17, 6707 (2009)
USBio References
No references available
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