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ILIMAQUINONE

Product Name
ILIMAQUINONE
CAS No.
71678-03-0
Chemical Name
ILIMAQUINONE
Synonyms
IQ;ILIMAQUINONE;illimaquinone;(-)-Ilimaquinine;(-)-ILIMAQUINONE;5-Epiilimaquinone;Ilimaquinone - CAS 71678-03-0 - Calbiochem;3-[(decahydro-1β,2β,4aβ-trimethyl-5-methylene-1-naphthyl)methyl]-2-hydroxy-5-methoxybenzoquinone;3-[(DECAHYDRO-1B,2B,4AB-TRIMETHYL-5-METHYLENE-1-NAPHTHYL)METHYL]-2-HYDROXY-5-METHOXYBENZOQUINONE;2-[[(1R,8aα)-1,2β,4aβ-Trimethyl-5-methylenedecalin-1α-yl]methyl]-3-hydroxy-6-methoxy-1,4-benzoquinone
CBNumber
CB5267651
Molecular Formula
C22H30O4
Formula Weight
358.47
MOL File
71678-03-0.mol
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ILIMAQUINONE Property

Melting point:
108-110℃ (pentane )
alpha 
D23 -23.2° (c = 1.12 in CHCl3)
Boiling point:
478.4±45.0 °C(Predicted)
Density 
1.14±0.1 g/cm3(Predicted)
storage temp. 
−20°C
solubility 
DMSO: Soluble; Ethanol: Soluble; Hexane: Soluble; Methanol: Soluble
pka
2.92±0.50(Predicted)
form 
Red solid
color 
Light yellow to brown
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Safety

WGK Germany 
3
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Alfa Aesar
Product number
J67278
Product name
Ilimaquinone, 98%
Packaging
100microg
Price
$199
Updated
2021/12/16
Cayman Chemical
Product number
15124
Product name
Ilimaquinone
Purity
≥98%
Packaging
100μg
Price
$209
Updated
2024/03/01
Usbiological
Product number
044951
Product name
Ilimaquinone
Packaging
100ug
Price
$350
Updated
2021/12/16
TRC
Product number
I267318
Product name
Ilimaquinone
Packaging
500μg
Price
$920
Updated
2021/12/16
Adipogen Life Sciences
Product number
AG-CN2-0038-C100
Product name
Ilimaquinone
Purity
≥98%(HPLC)
Packaging
100μg
Price
$130
Updated
2021/12/16
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ILIMAQUINONE Chemical Properties,Usage,Production

Description

Ilimaquinone is a natural sesquiterpene quinone that has antimicrobial, anti-HIV, anti-mitotic, and anti-inflammatory properties. In mammalian cells, 25 μM ilimaquinone reversibly induces vesiculation of Golgi membranes, blocking the secretory pathway. It inhibits the conversion of S-adenosylhomocysteine (SAH) to homocysteine by SAH hydrolase (IC50 = 40 μM). Ilimaquinone also inhibits DNA polymerase β and dual specificity phosphatase Cdc25B (IC50 = 45.2 and 92 μM, respectively) and, at 10 μM, activates gene expression through hypoxia-inducible factor-1.

Uses

Ilimaquinone is an ADP-ribosylation factor (ARF) and β-COP to the Golgi membrane inhibitor.

Uses

Biological probe for intracellular communications and vesicle-mediated transport.

Definition

ChEBI: A natural product found in Dactylospongia elegans.

General Description

A cell-permeable marine sponge metabolite with anti-microbial, anti-HIV, anti-inflammatory, and anti-mitotic properties. Induces a complete and reversible breakdown of Golgi membranes into smaller vesicular structures and causes depolymerization of microtubules. Inhibits cellular methylations through its interaction with S-adenosylhomocysteinase. Blocks the cytotoxicity of ricin and diphtheria toxin. Acts as an inhibitor of the RNase H activity of HIV-1.

Biochem/physiol Actions

Primary TargetInduces a complete and reversible breakdown of Golgi membranes into smaller vesicular structures and causes depolymerization of microtubules.

ILIMAQUINONE Preparation Products And Raw materials

Raw materials

Preparation Products

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ILIMAQUINONE Suppliers

China 43 Germany 1 Japan 1 Switzerland 2 United Kingdom 3 United States 11 Global 61
SIGMA-RBI
Tel
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Fax
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Country
Switzerland
ProdList
6896
Advantage
91
Alexis Corporation
Tel
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Fax
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Email
alexis-ch@alexis-corp.ch
Country
Switzerland
ProdList
3599
Advantage
74

71678-03-0, ILIMAQUINONERelated Search:

5'-GUANYLYLIMIDODIPHOSPHATE TRISODIUM EMBELIN 2,5-DIHYDROXY-1,4-BENZOQUINONE PRIMIN ILIMAQUINONE 3-methoxy-2,5-toluquinone METHOXYBENZOQUINONE p-Toluquinone

  • Ilimaquinone - CAS 71678-03-0 - Calbiochem
  • 3-[(DECAHYDRO-1B,2B,4AB-TRIMETHYL-5-METHYLENE-1-NAPHTHYL)METHYL]-2-HYDROXY-5-METHOXYBENZOQUINONE
  • 3-[(DECAHYDRO-1BETA,2BETA,4A-BETA-TRIMETHYL-5-METHYLENE-1-NAPHTHYL)-METHYL]-2-HYDROXY-5-METHOXYBENZOQUINONE
  • 3-[(DECAHYDRO-1BETA,2BETA,4A-BETA-TRIMETHYL-5-METHYLENE-1-NAPTHYL)METHYL]-2-HYDROXY-5-METHOXYBENZOQUINONE
  • 3-[(DECAHYDRO-1BETA,2BETA,4ALPHA-BETA-TRIMETHYL-5-METHYLENE-1-NAPHTHYL)METHYL]-2-HYDROXY-5-METHOXYBENZOQUINONE
  • IQ
  • ILIMAQUINONE
  • 3-[(decahydro-1β,2β,4aβ-trimethyl-5-methylene-1-naphthyl)methyl]-2-hydroxy-5-methoxybenzoquinone
  • illimaquinone
  • 5-Epiilimaquinone
  • (-)-Ilimaquinine
  • 2-[[(1R,8aα)-1,2β,4aβ-Trimethyl-5-methylenedecalin-1α-yl]methyl]-3-hydroxy-6-methoxy-1,4-benzoquinone
  • 3-[[(1R,8aα)-Decahydro-1,2β,4aβ-trimethyl-5-methylenenaphthalene-1α-yl]methyl]-2-hydroxy-5-methoxy-2,5-cyclohexadiene-1,4-dione
  • 3-[[[(1R,8aα)-Decahydro-1,2β,4aβ-trimethyl-5-methylenenaphthalen]-1α-yl]methyl]-2-hydroxy-5-methoxy-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-2,5-cyclohexadiene-1,4-dione
  • (-)-ILIMAQUINONE
  • 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-
  • 71678-03-0
  • Cell Biology
  • Cell Signaling and Neuroscience
  • BioChemical
  • Organelle Proteins and Related Molecules
  • Cytoskeleton and Extracellular Matrix