Date published: 2025-11-2

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Tropolone (CAS 533-75-5)

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Alternate Names:
2-Hydroxy-2,4,6-cycloheptatrien-1-one
Application:
Tropolone is a reagent for the preparation of fused heterocycles and complexes of Ga(III) and In(III)
CAS Number:
533-75-5
Purity:
≥99%
Molecular Weight:
122.12
Molecular Formula:
C7H6O2
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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Tropolone, a compound naturally occurring in plant species of the genus Myrtus, particularly M. pomifera and M. rotundifolia, exhibits notable properties. Extensive research has highlighted its anti-inflammatory characteristics and its ability to hinder the generation of reactive oxygen species (ROS) in vitro. In investigating the impact of tropolone on mitochondrial functionality, it was observed there was an elevation in mitochondrial membrane potential. This finding sheds light on tropolone′s influence on cellular processes. Furthermore, molecular modeling endeavors have provided valuable insights by elucidating the x-ray crystal structures of tropolone and its intricate complex with dioxygen. These structures have divulged the binding of tropolone to the heme moiety of cytochrome c oxidase, which consequently impedes electron transfer reactions within mitochondria. Another significant effect of tropolone is its inhibition of DNA, RNA, protein, and phospholipid synthesis. This inhibition underscores the compound′s potential impact on fundamental biological processes.


Tropolone (CAS 533-75-5) References

  1. Sesquiterpenoid tropolone glycosides from Liriosma ovata.  |  Ma, J., et al. 2015. J Nat Prod. 78: 315-9. PMID: 25587934
  2. The tropolone-isobutylamine complex: a hydrogen-bonded troponoid without dominant π-π interactions.  |  Vealey, ZN., et al. 2016. Acta Crystallogr C Struct Chem. 72: 730-737. PMID: 27703119
  3. Biotoxin Tropolone Contamination Associated with Nationwide Occurrence of Pathogen Burkholderia plantarii in Agricultural Environments in China.  |  Liu, X., et al. 2018. Environ Sci Technol. 52: 5105-5114. PMID: 29589436
  4. A sesquiterpenoid tropolone and 1,2,3,4-tetrahydronaphthalene derivatives from Olax imbricata roots.  |  Nguyen, HTM., et al. 2019. Fitoterapia. 132: 1-6. PMID: 30439445
  5. Tropolone-Conjugated DNA: Fluorescence Enhancement in the Duplex.  |  Bollu, A. and Sharma, NK. 2019. Chembiochem. 20: 1467-1475. PMID: 30677202
  6. Tropolone alkaloids from Colchicum kurdicum (Bornm.) Stef. (Colchicaceae) as the potent novel antileishmanial compounds; purification, structure elucidation, antileishmanial activities and molecular docking studies.  |  Azadbakht, M., et al. 2020. Exp Parasitol. 213: 107902. PMID: 32353376
  7. Synthetic Biology Driven Biosynthesis of Unnatural Tropolone Sesquiterpenoids.  |  Schotte, C., et al. 2020. Angew Chem Int Ed Engl. 59: 23870-23878. PMID: 32929811
  8. Tropolone derivatives with hepatoprotective and antiproliferative activities from the aerial parts of Chenopodium album Linn.  |  Ma, QG., et al. 2020. Fitoterapia. 146: 104733. PMID: 32979464
  9. Tropolone-Bearing Sesquiterpenes from Juniperus chinensis: Structures, Photochemistry and Bioactivity.  |  Park, JS., et al. 2021. J Nat Prod. 84: 2020-2027. PMID: 34236881
  10. Regioselective approach to colchiceine tropolone ring functionalization at C(9) and C(10) yielding new anticancer hybrid derivatives containing heterocyclic structural motifs.  |  Pyta, K., et al. 2022. J Enzyme Inhib Med Chem. 37: 597-605. PMID: 35067138
  11. Total Synthesis of Gukulenin B via Sequential Tropolone Functionalizations.  |  Nicolaou, KC., et al. 2022. J Am Chem Soc. 144: 5190-5196. PMID: 35275627
  12. Discovery of Tropolone Stipitaldehyde as a Potential Agent for Controlling Phytophthora Blight and Its Action Mechanism Research.  |  Wang, B., et al. 2022. J Agric Food Chem. 70: 8693-8703. PMID: 35793537
  13. Tropolone-Conjugated DNA: A Fluorescent Thymidine Analogue Exhibits Solvatochromism, Enzymatic Incorporation into DNA and HeLa Cell Internalization.  |  Meher, S., et al. 2023. Chembiochem. 24: e202200732. PMID: 36510378

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

Tropolone, 1 g

sc-253808
1 g
$32.00

Tropolone, 5 g

sc-253808A
5 g
$109.00