Tropolone
(Synonyms: 环庚三烯酚酮) 目录号 : GC46234
A terpene with diverse biological activities
Cas No.:533-75-5
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
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 is an iron chelator that inhibits iron-dependent growth of the wood rot fungus P. placenta when used at a concentration of 50 μM and P. placenta degradation of pine sapwood blocks impregnated with 5 mM tropolone.3 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.
|1. Borchardt, R.T. Catechol 0-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).
| Cas No. | 533-75-5 | SDF | |
| 别名 | 环庚三烯酚酮 | ||
| Canonical SMILES | OC1=CC=CC=CC1=O | ||
| 分子式 | C7H6O2 | 分子量 | 122.1 |
| 溶解度 | DMF: 5mg/mL,DMSO: 10mg/mL,Ethanol: 30mg/mL,Ethanol:PBS (pH 7.2) (1:6): 0.14mg/mL | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 8.19 mL | 40.95 mL | 81.9001 mL |
| 5 mM | 1.638 mL | 8.19 mL | 16.38 mL |
| 10 mM | 0.819 mL | 4.095 mL | 8.19 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Tropolone natural products
Nat Prod Rep 2019 Aug 14;36(8):1137-1155.PMID:30556819DOI:10.1039/c8np00078f.
Covering: 2008 to 2018 This review provides a comprehensive overview of newly discovered natural products containing a tropolonoid motif covering 2008 up to 2018 and depicts the ecological context in which they have been isolated. This review has a strong focus on describing the different analytical tools and molecular biological approaches used to identify the underlying biosynthetic pathways.
Tropolone derivative hinokitiol ameliorates cerulein-induced acute pancreatitis in mice
Int Immunopharmacol 2022 Aug;109:108915.PMID:35679663DOI:10.1016/j.intimp.2022.108915.
Hinokitiol is a natural bio-active Tropolone derivative with promising antioxidant and anti-inflammatory properties. This study was conducted to evaluate the ameliorative effects of hinokitiol against acute pancreatitis induced by cerulein. Mice were pre-treated with hinokitiol intraperitoneally for 7 days (50 and 100 mg/kg), and on the final day of study, cerulein (6 × 50 μg/kg) was injected every hour for six times. Six hours after the last dose of cerulein, blood was collected from the mice through retro-orbital plexus for biochemical analysis. After blood collection, mice were euthanized and the pancreas was harvested for studying effects on oxidative stress, pro-inflammatory cytokines, immunohistochemistry and histopathology of tissue sections. Hinokitiol treatment significantly reduced edema of the pancreas and reduced the plasma levels of lipase and amylase in mice with cerulein-induced acute pancreatitis. It also attenuated the oxidative and nitrosative stress related damage as evident from the reduced malondialdehyde (MDA) and nitrite levels, which were significantly increased in the mice with acute pancreatitis. Furthermore, hinokitiol administration significantly reduced the pancreatitis-evoked decrease in the activity of catalase, glutathione (GSH) and superoxide dismutase (SOD) in the pancreatic tissue. Pre-treatment with hinokitiol significantly reduced the elevated levels of pro-inflammatory cytokines like interleukin-6 (IL-6), interleukin-1β (IL-1β), tumor necrosis factor-alpha (TNF-α) as well as increased the levels of anti-inflammatory cytokine interleukin-10 (IL-10) in the pancreatic tissue of mice with acute pancreatitis. The immunohistochemical expression of nuclear factor kappa light chain enhancer of activated B cells (NF-κB), cyclooxygenase (COX-2) and TNF-α were significantly decreased by hinokitiol in mice with cerulein-induced acute pancreatitis. In conclusion, the results of the present study demonstrate that hinokitiol has significant potential to prevent cerulein-induced acute pancreatitis.
Tropolone-Bearing Sesquiterpenes from Juniperus chinensis: Structures, Photochemistry and Bioactivity
J Nat Prod 2021 Jul 23;84(7):2020-2027.PMID:34236881DOI:10.1021/acs.jnatprod.1c00321.
The tropolone-bearing sesquiterpenes juniperone A (1) and norjuniperone A (2) were isolated from the folk medicinal plant Juniperus chinensis, and their structures were determined by a combination of spectroscopic and crystallographic methods. Photojuniperones A1 (3) and A2 (4), bearing bicyclo[3,2,0]heptadienones derived from Tropolone, were photochemically produced and structurally identified by spectroscopic methods. Predicted by the machine learning-based assay, 1 significantly inhibited the action of tyrosinase. The new compounds also inhibited lipid accumulation and enhanced the extracellular glycerol excretion.
Tropolone-Conjugated DNA: Fluorescence Enhancement in the Duplex
Chembiochem 2019 Jun 3;20(11):1467-1475.PMID:30677202DOI:10.1002/cbic.201800822.
Tropolone (2-hydroxycyclohepta-2,4,6-triene-1-one and tautomer) is a non-benzenoid bioactive natural chromophore with pH-dependent fluorescence character and extraordinary metal binding affinities, especially with transition-metal ions Cu2+ /Zn2+ /Ni2+ . This report describes the syntheses and biophysical studies of a new tropolonyl thymidine [(4(5)-hydroxy-5(4)-oxo-5(4)H-cyclohepta-1,3,6-trienyl)thymidine] (tr-T) nucleoside and of corresponding tropolone-conjugated DNA oligonucleotides that form B-form DNA duplex structures with a complementary DNA strand, although their duplex structures are less stable than that of the control. Furthermore, the stabilities of those DNA duplex structures are lowered by the presence of increasing numbers of tr-T residue or by decreasing pH of their environments. Most importantly, these duplex structures are made fluorescent because of the presence of the Tropolone moieties conjugated to the thymidine residues. The fluorescence behavior of those duplex structures exhibits pH dependence, with stronger fluorescence at lower pH and weaker fluorescence at high pH. Importantly, the fluorescence characters of tr-DNA oligonucleotides are significantly enhanced by nearly threefold after duplex structure formation with their complementary control DNA oligonucleotide. Further, the fluorescence behavior of these tr-DNA duplex structures is also dependent on the pH conditions. Hence, tropolonyl-conjugated DNA represents a class of new fluorescent analogues that might be be employed for sensing DNA duplex formation and provide opportunities to improve fluorescence properties further.
Total Synthesis of Gukulenin B via Sequential Tropolone Functionalizations
J Am Chem Soc 2022 Mar 23;144(11):5190-5196.PMID:35275627DOI:10.1021/jacs.2c01305.
The synthesis of functionalized aromatic compounds is a central theme of research for modern organic chemistry. Despite the increasing finesse in the functionalization of five- and six-membered aromatic rings, their seven-membered-ring sibling, Tropolone (2-hydroxy-2,4,6-cycloheptatrien-1-one), remains a challenging target for synthetic derivatization. This challenge primarily emanates from the unique structural and chemical properties of tropolonoid compounds, which often lead to unexpected and undesired reaction outcomes under conditions developed for the functionalizations of other aromatic moieties. Herein, we describe the total synthesis of one of the most complex natural tropolonoids, gukulenin B. Our synthetic route features a series of site-selective aromatic C-H bond functionalizations and C-C bond formations, whose reaction conditions are judiciously tuned to allow uncompromised performance on the Tropolone nucleus. The flexibility and modularity of our synthesis are expected to facilitate further synthetic and biological studies of the gukulenin family of cytotoxins. In addition, the methods and tactics developed herein for the functionalization of the Tropolone moiety could inspire and enable chemists of multiple disciplines to take advantage of this privileged yet underexplored structural motif.