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;Ilimaquinone, Cytoplasmic microtubule inhibitor;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
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

Sigma-Aldrich

Product number: 401250-M
Product name: Ilimaquinone
Purity: A cell-permeable marine sponge metabolite with anti-microbial, anti-HIV, anti-inflammatory, and anti-mitotic properties.
Packaging: 1 unit
Price: $240
Updated: 2025/07/31

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.

References

[1] H S RADEKE. Interactions of (-)-ilimaquinone with methylation enzymes: implications for vesicular-mediated secretion.[J]. Chemistry & biology, 1999, 6 9: 639-647. DOI: 10.1016/s1074-5521(99)80115-x
[2] P A TAKIZAWA. Complete vesiculation of Golgi membranes and inhibition of protein transport by a novel sea sponge metabolite, ilimaquinone.[J]. Cell, 1993, 73 6: 1079-1090. DOI: 10.1016/0092-8674(93)90638-7
[3] VéRONIQUE CRUCIANI Svein O M Edward Leithe. Ilimaquinone inhibits gap-junctional communication prior to Golgi fragmentation and block in protein transport[J]. Experimental cell research, 2003, 287 1: Pages 130-142. DOI: 10.1016/s0014-4827(03)00124-1
[4] BYUNG GYU KIM . A new structural class of S-adenosylhomocysteine hydrolase inhibitors[J]. Bioorganic & Medicinal Chemistry, 2009, 17 18: Pages 6707-6714. DOI: 10.1016/j.bmc.2009.07.061
[5] SHUGENG CAO. Marine Sesquiterpenoids that Inhibit the Lyase Activity of DNA Polymerase β[J]. Journal of Natural Products , 2004, 67 10: 1716-1718. DOI: 10.1021/np049849+
[6] LIN DU Dale G N Yu Dong Zhou*. Inducers of Hypoxic Response: Marine Sesquiterpene Quinones Activate HIF-1[J]. Journal of Natural Products , 2013, 76 6: 1175-1181. DOI: 10.1021/np400320r

ILIMAQUINONE Preparation Products And Raw materials

Raw materials

Preparation Products

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ILIMAQUINONE Suppliers

China 52 Germany 1 Japan 1 Switzerland 2 United Kingdom 3 United States 12 Global 71

Shanghai Tauto Biotech Co., Ltd.

Tel: 021-51320588
Fax: 0086-21-51320502
Email: tauto@tautobiotech.com
Country: China
ProdList: 3988
Advantage: 66

Hotechem Shanghai Co., Ltd.,

Tel: 021-34621078 13120882795
Fax: 021-34622517
Email: 465106944@qq.com
Country: China
ProdList: 857
Advantage: 56

Shanghai EFE Biological Technology Co., Ltd.

Tel: 021-65675885 18964387627
Fax: 021-65675885
Email: info@efebio.com
Country: China
ProdList: 9803
Advantage: 58

TargetMol Chemicals Inc.

Tel: +1-781-999-5354; +17819995354
Email: marketing@targetmol.com
Country: United States
ProdList: 32435
Advantage: 58

ChemeGen(Shanghai) Biotechnology Co.,Ltd.

Tel: 18818260767
Fax: QQ 3610331285
Email: sales@chemegen.com
Country: China
ProdList: 11218
Advantage: 58

TargetMol Chemicals Inc.

Tel: 4008200310
Email: marketing@tsbiochem.com
Country: China
ProdList: 24961
Advantage: 58

Adipogen Life Sciences

Tel: 41-6192660-40
Email: info@adipogen.com
Country: China
ProdList: 5293
Advantage: 58

Merck Millipore

Tel: 1-400-889-1988 400-889-1988
Email: bioscience@merckgroup.com
Country: China
ProdList: 6839
Advantage: 58

Cayman Chemical Company

Tel: 800-364-9897
Email: sales@caymanchem.com
Country: China
ProdList: 6838
Advantage: 58

Enzo Biochem Inc

Tel: Enzo Biochem Inc. 13797054060
Email: Enzoname@qq.com
Country: China
ProdList: 6174
Advantage: 58

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-

Ilimaquinone, Cytoplasmic microtubule inhibitor

71678-03-0

Cell Biology

Cell Signaling and Neuroscience

BioChemical

Organelle Proteins and Related Molecules

Cytoskeleton and Extracellular Matrix