Terpinen-4-ol
(Synonyms: 4-萜烯醇; 4-Carvomenthenol) 目录号 : GC39115
Terpinen-4-ol, a naturally occurring monoterpene, is the main bioactive component of tea-tree oil and has been shown to have many biological activities such as antifungal properties.
Cas No.:562-74-3
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
Terpinen-4-ol, a naturally occurring monoterpene, is the main bioactive component of tea-tree oil and has been shown to have many biological activities such as antifungal properties.
| Cas No. | 562-74-3 | SDF | |
| 别名 | 4-萜烯醇; 4-Carvomenthenol | ||
| Canonical SMILES | CC1=CCC(C(C)C)(O)CC1 | ||
| 分子式 | C10H18O | 分子量 | 154.25 |
| 溶解度 | DMSO : 100mg/mL | 储存条件 | 4°C, protect from light |
| 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 | 6.483 mL | 32.4149 mL | 64.8298 mL |
| 5 mM | 1.2966 mL | 6.483 mL | 12.966 mL |
| 10 mM | 0.6483 mL | 3.2415 mL | 6.483 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。
Terpinen-4-ol as an Antibacterial and Antibiofilm Agent against Staphylococcus aureus
Int J Mol Sci 2020 Jun 25;21(12):4531.PMID:32630600DOI:10.3390/ijms21124531.
Staphylococcus aureus is able to rapidly develop mechanisms of resistance to various drugs and to form strong biofilms, which makes it necessary to develop new antibacterial drugs. The essential oil of Melaleuca alternifolia is used as an antibacterial, a property believed to be mainly due to the presence of Terpinen-4-ol. Based on this, the objective of this study was to evaluate the antibacterial and antibiofilm potential of Terpinen-4-ol against S. aureus. The Minimal Inhibitory and Minimal Bactericidal Concentrations (MIC and MBC) of Terpinen-4-ol were determined, and the effect of its combination with antibacterial drugs as well as its activity against S. aureus biofilms were evaluated. In addition, an in silico analysis of its pharmacokinetic parameters and a molecular docking analysis were performed. Terpinen-4-ol presented a MIC of 0.25% (v/v) and an MBC of 0.5% (v/v) (bactericidal action); its association with antibacterials was also effective. Terpinen-4-ol has good antibiofilm activity, and the in silico results indicated adequate absorption and distribution of the molecule in vivo. Molecular docking indicated that penicillin-binding protein 2a is a possible target of Terpinen-4-ol in S. aureus. This work highlights the good potential of Terpinen-4-ol as an antibacterial product and provides support for future pharmacological studies of this molecule, aiming at its therapeutic application.
Negative Terpinen-4-ol modulate potentially malignant and malignant lingual lesions induced by 4-nitroquinoline-1-oxide in rat model
Naunyn Schmiedebergs Arch Pharmacol 2022 Nov;395(11):1387-1403.PMID:35943514DOI:10.1007/s00210-022-02275-7.
Our aim was to verify the modulative TP-4-ol capacity in 4-nitroquinoline-1-oxide induced oral rat cancer. The stereoisomers of TP-4-ol were used against the human tongue squamous cell line and the negative stereoisomer showed lower IC50. Thirty-one Holtzman rats (120-130 g) were cancer-induced by 4-nitroquinoline-1-oxide (4-NQO/8 weeks/25 ppm) and 32 Holtzman rats (120-130 g) were used to healthy and TP-4-ol toxicity experiments. Six groups were used, healthy, 0.1nL/g of TP-4-ol, 8nL/g of TP-4-ol, 4-NQO, 4-NQO + 0.1nL/g of TP-4-ol, and 4-NQO + 8nL/g of TP-4-ol. We performed the toxicity analysis by biochemical and histopathological analysis. The biochemistry analysis includes alkaline phosphatase (ALP), alanine aminotransferase (ALT), aspartate transaminase (AST), urea, and creatinine and the histopathology analysis includes the liver, kidney, lung, and spleen. Specifically, for malign modulation, we performed a macroscopic and microscopic analysis. The group exposed to 0.1nL/g of TP-4-ol demonstrated a reduced risk of malignancy in dysplasia considering the criteria of architecture and cytology. Similarly, a drop of percentual rats with SCC diagnosis was observed in 4-NQO + 0.1nL/g (41.6%) when compared to 4-NQO (87.5%). Moreover, the 4-NQO group presented a median of 2.62 SCC/rat and the 4-NQO + 0.1nL/g demonstrated a median of 0.75 SCC/rat. For toxicity analysis, 4-NQO + 0.1nL/g showed focal necrosis in the kidney and 4-NQO showed lung hemorrhagic areas. The concentration of 0.1nL/g was more effective in reducing the tongue induction of potentially malignant and malignant lesions by 4-NQO. A kidney toxicity was observed in healthy animals exposed to 0.1nL/g of TP-4-ol. The negative isoform of Terpinen-4-ol negatively modulates the development of potentially malignant and malignant lesions in rats (Rattus nonverdicts albinos, Holtzman) exposed to 4-NQO. (-)-Terpinen-4-ol reduced the mice percentual with squamous cell carcinoma, 87.5 to 41.6%, and decreased the cancer/rat ratio of 2.62 in 4-NQO to 0.75 in 4-NQO + 0.1nL/g. This represents 52.4% by group and 71.3% in the cancer/rat ratio.
Terpinen-4-ol, the Main Bioactive Component of Tea Tree Oil, as an Innovative Antimicrobial Agent against Legionella pneumophila
Pathogens 2022 Jun 14;11(6):682.PMID:35745536DOI:10.3390/pathogens11060682.
Legionella pneumophila (Lp), responsible for a severe pneumonia called Legionnaires' disease, represents an important health burden in Europe. Prevention and control of Lp contamination in warm water systems is still a great challenge often due to the failure in disinfection procedures. The aim of this study was to evaluate the in vitro activity of Terpinen-4-ol (T-4-ol) as potential agent for Lp control, in comparison with the essential oil of Melaleuca alternifolia (tea tree) (TTO. Minimum Inhibitory Concentration (MIC) and Minimum Bactericidal Concentration (MBC) of T-4-ol were determined by broth micro-dilution and a micro-atmosphere diffusion method to investigate the anti-Lp effects of T-4-ol and TTO vapors. Scanning Electron Microscopy (SEM) was adopted to highlight the morphological changes and Lp damage following T-4-ol and TTO treatments. The greatest antimicrobial activity against Lp was shown by T-4-ol with a MIC range of 0.06-0.125% v/v and MBC range of 0.25-0.5% v/v. The TTO and T-4-ol MIC and MBC decreased with increasing temperature (36 °C to 45 ± 1 °C), and temperature also significantly influenced the efficacy of TTO and T-4-ol vapors. The time-killing assay showed an exponential trend of T-4-ol bactericidal activity at 0.5% v/v against Lp. SEM observations revealed a concentration- and temperature- dependent effect of T-4-ol and TTO on cell surface morphology with alterations. These findings suggest that T-4-ol is active against Lp and further studies may address the potential effectiveness of T-4-ol for control of water systems.
Antifungal activity and Shore A hardness of a tissue conditioner incorporated with Terpinen-4-ol and cinnamaldehyde
Clin Oral Investig 2019 Jul;23(7):2837-2848.PMID:31111285DOI:10.1007/s00784-019-02925-w.
Purpose: This study investigated the anti-Candida activity and the Shore A hardness of a tissue conditioner (Softone™) modified by incorporation of Terpinen-4-ol and cinnamaldehyde. Material and methods: Agar diffusion, microdilution, and mechanism of action methods were performed to determine to evaluate the antifungal activity of phytoconstituents. Then, phytoconstituents in varying concentrations were incorporated into the tissue conditioner. The anti-Candida effect of the modified conditioner was evaluated through agar punch well and biofilm formation methods. Shore A hardness of the experimental liners was evaluated after baseline, 24 h, 48 h, 4 days, and 7 days immersion on artificial saliva. Results: The phytoconstituents incorporated into Softone showed completely inhibited fungal growth in concentrations of 20-40% and did not present significant antifungal activity until their concentrations where higher than 5%. There were differences between non-modified Softone and M5, M10, C10, and T10% (p < 0.05). The groups containing 10-40% of cinnamaldehyde incorporated into Softone were able to completely inhibit the biofilm. Concentrations below 40% of Terpinen-4-ol showed unsatisfactory biofilm inhibition. The T40% and C40% groups presented the lowest Shore A hardness values. Hardness values from groups T40% at 7 days (p = 0.476); C40% at 4 days (p = 0.058); and T20% (p = 0.058), C20% (p = 0.205), T30% (p = 0.154), and C30% (p = 0.874) after 48 h did not differ from the control group. Conclusions: Cinnamaldehyde incorporated into Softone inhibited Candida biofilm formation at concentrations of 10-40%, being more effective than Terpinen-4-ol modification despite of halo inhibition observed by both products. Clinical relevance: All modifications showed a very similar pattern of hardness being useful for clinical practice.
Terpinen-4-ol attenuates quorum sensing regulated virulence factors and biofilm formation in Pseudomonas aeruginosa
Future Microbiol 2020 Jan;15:127-142.PMID:32043363DOI:10.2217/fmb-2019-0204.
Aim: To investigate the effects of Terpinen-4-ol on quorum sensing (QS)-regulated biofilm formation and virulence factors production in Pseudomonas aeruginosa. Materials & methods: QS inhibition, molecular docking analysis and gene expression studies were performed to check attenuation effect of Terpinen-4-ol on virulence of P. aeruginosa. Production of various virulence factors and biofilm formation were studied at sub-MIC of Terpinen-4-ol alone and in combination with ciprofloxacin. Results: Terpinen-4-ol at sub-MIC exhibited QS inhibition and downregulated all key QS genes. Molecular docking analysis showed high binding affinities of Terpinen-4-ol with QS receptors. Terpinen-4-ol exhibited synergistic interaction with ciprofloxacin and further reduced production of all the virulence factors and biofilms formation. Conclusion: Terpinen-4-ol could be developed into antivirulence drug after its in vivo evaluation for treatment strategies.