β-thujaplicin

Catalog No.S4771 Synonyms: Hinokitiol, 4-Isopropyltropolone

For research use only.

β-Thujaplicin (β-TH, Hinokitiol, 4-Isopropyltropolone) is a toxic tropolone derivative present in the heartwood of western red cedar (Thuja plicata) and is used as a preservative and antimicrobial additive in a number of commercial goods. Hinokitiol is a component of essential oils isolated from Chymacyparis obtusa, reduces Nrf2 expression, and decreases DNMT1 and UHRF1 mRNA and protein expression, with anti-infective, anti-oxidative, and anti-tumor activities.

β-thujaplicin Chemical Structure

CAS No. 499-44-5

Purity & Quality Control

Choose Selective DNA Methyltransferase Inhibitors

Biological Activity

Description β-Thujaplicin (β-TH, Hinokitiol, 4-Isopropyltropolone) is a toxic tropolone derivative present in the heartwood of western red cedar (Thuja plicata) and is used as a preservative and antimicrobial additive in a number of commercial goods. Hinokitiol is a component of essential oils isolated from Chymacyparis obtusa, reduces Nrf2 expression, and decreases DNMT1 and UHRF1 mRNA and protein expression, with anti-infective, anti-oxidative, and anti-tumor activities.
In vitro

In lung cancer cells, hinokitiol inhibits cell proliferation by inducing the p53-independent DNA damage response, autophagy (not apoptosis), S-phase cell cycle arrest, and senescence. Hinokitiol induces autophagy in lung adenocarcinoma cells but not in human lung stromal fibroblasts. It induces cellular senescence in both human lung cancer cells and lung stromal fibroblasts[1]. Treatment with hinokitiol reveals a concentration-dependent inhibition of migration of B16-F10 melanoma cells. It appears to achieve this effect by reducing the expression of MMP-1 and by suppressing the phosphorylation of mitogen- activated protein kinase (MAPK) signaling molecules such as extracellular signal-regulated kinase (ERK) 1/2, p38 MAPK and c-Jun N-terminal kinases (JNK). On the other hand, hinokitiol treatment reverses IκB-α degradation and inhibits the phosphorylation of p65 nuclear factor kappa B (NF-κB) and cJun in B16-F10 cells. In addition, hinokitiol suppresses the translocation of p65 NF-κB from the cytosol to the nucleus, suggesting reduced NF-κB activation[2].

In vivo Hinokitiol reduces tumor growth, potentially through the attenuation of tumorigenicity, and induces DNA damage and autophagy to suppress tumor progression[1]. In vivo study demonstrates that hinokitiol treatment significantly reduces the total number of mouse lung metastatic nodules and improves histological alterations in B16-F10 injected C57BL/6 mice[2].

Protocol (from reference)

Cell Research:[1]
  • Cell lines: A549 cells
  • Concentrations: 0.3125-10 µM
  • Incubation Time: 24, 48, and 72 h
  • Method: For trypan blue staining, 2×104 cells are cultured in 12-well plates overnight and then incubated with 0.3125-10 µM hinokitiol for 24, 48, and 72 h. At the indicated times, the cells are trypsinized and stained with trypan blue. The viable cells that excluded trypan blue are counted in a counting chamber.
  • (Only for Reference)
Animal Research:[1]
  • Animal Models: Six-week old NOD-SCID mice
  • Dosages: 2 or 10 mg/kg
  • Administration: i.p.
  • (Only for Reference)

Solubility (25°C)

In vitro

DMSO 32 mg/mL
(194.88 mM)


* Please note that Selleck tests the solubility of all compounds in-house, and the actual solubility may differ slightly from published values. This is normal and is due to slight batch-to-batch variations.

Chemical Information

Molecular Weight 164.20
Formula

C10H12O2

CAS No. 499-44-5
Storage 3 years -20°C powder
2 years -80°C in solvent
Smiles CC(C)C1=CC(=O)C(=CC=C1)O

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