A tropolone with diverse biological activities
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Hinokitiol

Item No. 17538

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-hydroxy-4-(1-methylethyl)-2,4,6-cycloheptatrien-1-one
CAS Number
499-44-5
Synonyms
  • NSC 18804
  • β-Thujaplicin
  • 4-isopropyl Tropolone
Molecular Formula
C10H12O2
Formula Weight
164.2
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 12.5 mg/mlDMSO: 30 mg/mlDMSO:PBS(pH 7.2) (1:4): 0.2 mg/mlEthanol: 20 mg/ml
λmax
238, 320 nm
SMILES
O=C1C(O)=CC(C(C)C)=CC=C1
InChi Code
InChI=1S/C10H12O2/c1-7(2)8-4-3-5-9(11)10(12)6-8/h3-7H,1-2H3,(H,11,12)
InChi Key
FUWUEFKEXZQKKA-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    25 mg

    $41

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    50 mg

    $72

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    100 mg

    $127

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    250 mg

    $255

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    Product Description

    Hinokitiol is a tropolone originally isolated from the heart wood of T. plicata that has diverse biological activities, including antifungal, antibacterial, and antiproliferative properties.1,2,3 It inhibits proliferation of HCT-116 and SW-620 colon cancer cells (IC50s = 4.5 and 4.4 µM, respectively), arrests the cell cycle, and induces apoptosis.4 In mouse xenograft models of colon cancer, hinokitiol (100 mg/kg) decreases tumor volume and weight. It also has effects on platelets, inhibiting thrombus formation in mice and selectively inhibiting platelet-type 12-lipoxygenase (12-LO; IC50 = 0.1 µM) over leukocyte-type 12-LO (IC50 = 50 µM) in vitro.5,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Anderson, A.B., and Gripenberg, J. Antibiotic substances from the heart wood of Thuja plicata D. Don; the constitution of β-thujaplicin. Acta. Chem. Scand. 2(8), 644-650 (1948).

    2. Komaki, N., Watanabe, T., Ogasawara, A., et al. Antifungal mechanism of hinokitiol against Candida albicans. Biol. Pharm. Bull. 31(4), 735-737 (2008).

    3. Morita, Y., Sakagami, Y., Okabe, T., et al. The mechanism of the bactericidal activity of hinokitiol. Biocontrol Sci. 12(3), 101-110 (2007).

    4. Lee, Y.S., Choi, K.M., Kim, W., et al. Hinokitiol inhibits cell growth through induction of S-phase arrest and apoptosis in human colon cancer cells and suppresses tumor growth in a mouse xenograft experiment. J. Nat. Prod. 76(12), 2195-2202 (2013).

    5. Lin, K.H., Kuo, J.R., Lu, W.J., et al. Hinokitiol inhibits platelet activation ex vivo and thrombus formation in vivo. Biochem. Pharmacol. 85(10), 1478-1485 (2013).

    6. Suzuki, H., Ueda, T., Juránek, I., et al. Hinokitiol, a selective inhibitor of the platelet-type isozyme of arachidonate 12-lipoxygenase. Biochem. Bioph. Res. Commun. 275(3), 885-889 (2000).