A terpene with diverse biological activities
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Tropolone

Item No. 29674

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-hydroxy-2,4,6-cycloheptatrien-1-one
CAS Number
533-75-5
Synonyms
  • 2-Hydroxytropone
  • α-Tropolone
  • NSC 89303
  • Purpurocatechol
Molecular Formula
C7H6O2
Formula Weight
122.1
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 5mg/mLDMSO: 10mg/mLEthanol: 30mg/mLEthanol:PBS (pH 7.2) (1:6): 0.14mg/mL
λmax
227, 319, 352 nm
SMILES
OC1=CC=CC=CC1=O
InChi Code
InChI=1S/C7H6O2/c8-6-4-2-1-3-5-7(6)9/h1-5H,(H,8,9)
InChi Key
MDYOLVRUBBJPFM-UHFFFAOYSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 g

    $28

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    5 g

    $90

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    10 g

    $165

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    25 g

    $310

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    Product Description

    Tropolone is a terpene that has been found in cupressaceous tree bark and has diverse biological activities.1,2,3,4,5 It inhibits catechol O-methyltransferase (COMT; Ki = 22 µM).1 Tropolone is bacteriostatic against a panel of Gram-positive and Gram-negative bacteria (MICs = 12-82 µM) and bactericidal against A. hydrophilia and C. violaceum when used at a concentration of 20 mM.2 It inhibits LPS-induced production of nitric oxide (NO) in RAW 264.7 cells (IC50 = 12 µM).4 Tropolone (0.25 mmol/animal) reduces thyroid radioiodide uptake in rats.5 Dietary administration of tropolone induces growth retardation and hyperactivity in mice.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Borchardt, R.T. Catechol O-methyltransferase. 1. Kinetics of tropolone inhibition. J. Med. Chem. 16(4), 377-382 (1973).

    2. Trust, T.J. Antibacterial activity of tropolone. Antimicrob. Agents Chemother. 7(5), 500-506 (1975).

    3. Diouf, P.N., Delbarre, N., Perrin, D., et al. Influence of tropolone on Poria placenta wood degradation. Appl. Environ. Microbiol. 68(9), 4377–4382 (2002).

    4. Nishishiro, M., Kurihara, T., Wakabayashi, H., et al. Effect of tropolone, azulene and azulenequinone derivatives on prostaglandin E2 production by activated macrophage-like cells. Anticancer Res. 29(1), 379-383 (2009).

    5. Lee, C.P., Hegarty, M.P., and Christie, G.S. Antithyroid and antiperoxidase activity of tropolone and 3-hydroxy-4-pyrone. Chem. Biol. Interact. 27(1), 17-26 (1979).