Terpinolene
(Synonyms: 4-Isopropylidene-1-Methylcyclohexene, p-Meth-1-en-8-yl-formate, δ-Terpinene, α-Terpinolene) 目录号 : GC41498
Terpinolene is a monoterpene found in the essential oils of various plants, including C.
Cas No.:586-62-9
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >85.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Terpinolene is a monoterpene found in the essential oils of various plants, including C. sativa, and has diverse biological activities including antiproliferative and antioxidant properties. It inhibits expression of AKT1 in Jurkat and K562 cells by 95% when used at a concentration of 0.05% and inhibits the growth of K562 cells when used at a concentration of 0.01%. Terpinolene also inhibits the growth of HT-29, Hep-2, NCI-292, and HL-60 cells (IC50s = 16.7, 13.7, 17.4, and 28.8 μg/ml, respectively). In cultured human blood cells, terpinolene (10-75 mg/L) increases total antioxidant capacity (TAC), but decreases cell viability when used at a concentration of ≥150 mg/L.
| Cas No. | 586-62-9 | SDF | |
| 别名 | 4-Isopropylidene-1-Methylcyclohexene, p-Meth-1-en-8-yl-formate, δ-Terpinene, α-Terpinolene | ||
| 分子式 | C10H16 | 分子量 | 136.2 |
| 溶解度 | Chloroform: Slightly Soluble,Methanol: Slightly Soluble | 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 | 7.3421 mL | 36.7107 mL | 73.4214 mL |
| 5 mM | 1.4684 mL | 7.3421 mL | 14.6843 mL |
| 10 mM | 0.7342 mL | 3.6711 mL | 7.3421 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。
Biological properties of Terpinolene evidenced by in silico, in vitro and in vivo studies: A systematic review
Phytomedicine 2021 Dec;93:153768.PMID:34634744DOI:10.1016/j.phymed.2021.153768.
Background: Terpinolene, a monoterpene that is naturally found in a variety of herbs, is widely used as a flavoring agent in the industry. Although it's well established in the literature that Terpinolene is an important component of plant extracts, the biological properties and the potential therapeutic use of this compound remain poorly explored. Purpose: This work aimed to answer the following guiding question: "What are the biological activities of Terpinolene demonstrated through in silico, in vitro, and in vivo assays?". Study design and methodology: A systematic review was carried out in four electronic databases (Embase, Web of Science, Scopus, and PubMed) according to the Preferred Reporting Items for Systematic Reviews and Meta-Analyses (PRISMA) guidelines, using the following search terms: Terpinolene "AND" activity "OR" properties "OR" therapeutic "OR" treatment. This search included manuscripts published between 1960 and June 2020. Study selection was conducted by two independent reviewers according to predefined criteria. Results: The initial search found a total of 2449 articles. However, only 57 of them were selected as they met the inclusion criteria and answered the guiding question. The analysis of these studies indicated that Terpinolene presents a series of biological effects, from which the antioxidant, larvicide, and insecticide activities stand out. Despite the evidence demonstrating that Terpinolene has the potential to be used in a broad pharmacological context, the mechanisms underlying its cellular and molecular effects remain to be better elucidated. In addition, the in vivo efficacy and safety of the administration of this compound have been poorly evaluated through either preclinical and clinical trials. Therefore, this study highlights the importance of characterizing the biological aspects and mechanisms of action of this natural compound. Conclusion: The data summarized in the present systematic review demonstrates the pharmacological potential of Terpinolene. Nevertheless, most studies included in this review provide a superficial characterization of Terpinolene biological effects and therefore, further research elucidating its mechanism of action and potential therapeutic benefits through preclinical and clinical trials are required. Nevertheless, due to its wide range of different biological activities, Terpinolene will certainly attract the interest of scientific research, which could significantly contribute to the development of new products with both therapeutic and environmental applications.
Terpinolene as an enhancer for ultrasonic disinfection of multi-drug-resistant bacteria in hospital wastewater
Environ Sci Pollut Res Int 2022 May;29(23):34500-34514.PMID:35037151DOI:10.1007/s11356-022-18611-6.
The present study reports for the first time, a novel disinfection method that combines ultrasonication with a natural biocide Terpinolene to inhibit tough and opportunistic antimicrobial-resistant (AMR) microorganisms isolated from hospital wastewater treatment plant (HWWTP). The enhancement of the disinfection process was evaluated for the effect of ultrasonication power, operating temperature, and inoculum size. A hybrid methodology combining Terpinolene with traditional physico-chemical method of acoustic cavitation delivered efficient disinfection of the secondary effluent of field scale HWWTP, amended with a higher inoculum size of multi-drug-resistant coliform bacteria Enterobactor sp., Citrobacter freundii, and Klebsiella pneumonia. A bacterial load of 6.4 log CFU/mL was completely eliminated in 25 min. The present study also reports that due to the hybrid process, a very small concentration of 0.312 mM (0.25 × Minimum Inhibitory Concentration or MBC) of Terpinolene was enough to completely disinfect the multi-drug-resistant coliforms. The leakage of intracellular nucleic acids during the disinfection process suggested disruption of cell membrane as the primary mechanism of disinfection followed by disruption of cellular metabolic function measured by respiratory chain dehydrogenase activity. Moreover, this study is the first to prove that Terpinolene remained stable even after the cavitation process, thus revealing possibilities of recycling of the natural compound for wastewater disinfection. The results of the present research suggest that using Terpinolene as a bio-additive can efficiently eliminate hazardous multi-drug-resistant bacteria and drastically reduce operational time and cost thus rendering it suitable to replace conventional wastewater disinfection.
Are thymol, rosefuran, Terpinolene and umbelliferone good scavengers of peroxyl radicals?
Phytochemistry 2021 Apr;184:112670.PMID:33524861DOI:10.1016/j.phytochem.2021.112670.
DFT-based computational calculations have been used to investigate the hydroperoxyl radical scavenging activity of four essential oil constituents namely thymol (Thy), rosefuran (Ros), Terpinolene (Ter), and umbelliferone (Umb). Different reaction mechanisms including formal hydrogen transfer (FHT), radical adduct formation (RAF), sequential proton loss electron transfer (SPLET), and sequential electron transfer proton transfer (SETPT) have been examined in the gas phase and physiological environments. It was found that the HOO radical scavenging activity of these compounds is strongly influenced by the environment, which becomes more important in water than pentyl ethanoate. According to the overall reaction rate constants, the phenolic compounds Thy and Umb are predicted to exhibit excellent activity in aqueous solution. Umb with an overall rate constant of 1.44 × 108M-1s-1 at physiological pH is among the best HOO radical scavengers in water with activity comparable to that of caffeic acid, higher than those of ascorbic acid, guaiacol and eugenol, and much higher than that of Trolox.
Toxic effects of Terpinolene on Microcystis aeruginosa: Physiological, metabolism, gene transcription, and growth effects
Sci Total Environ 2020 Jun 1;719:137376.PMID:32135322DOI:10.1016/j.scitotenv.2020.137376.
Bioherbicide Terpinolene is widely employed in the agricultural field because of its unique phytotoxic properties. However, little is known about the toxicity of bioherbicide on harmful algal blooms (HABs) and its mechanisms. Therefore, in this study, the inhibiting effect of bioherbicide Terpinolene on the growth and physiological change of Microcystis aeruginosa was determined. Results showed that the cell density and photosynthetic activity of microalgae were significantly inhibited by Terpinolene. Activities of nitrate reductase (NR) and glutamine synthetase (GS) were decreased separately by 25.38% and 42.75% after 4 d of exposure to 1.47 mM Terpinolene, suggesting the inhibiting effect of Terpinolene on algal nitrogen metabolism. However, the transcript abundance of genes related to membrane protein cytochrome c oxidase subunit II (COX II) and ATP-binding cassette transporters (ABC transporter) were enhanced separately by 3.15 and 1.69-fold compared with control, suggesting the resistance response of cells to Terpinolene stress. Additionally, Terpinolene not only increased the content of endogenous phytohormones including indole-3-acetic acid (IAA), zeatin, and brassinolide, but also inhibited the expression of genes related to calcium-binding protein (CaBPs), one kind of calcium (Ca2+) sensors, suggesting its regulation on algal signal molecules. These findings helped to understand the ecotoxicity of Terpinolene and guide the rational use of bioherbicide in agriculture.
Effect of Terpinolene against the resistant Staphylococcus aureus strain, carrier of the efflux pump QacC and β-lactamase gene, and its toxicity in the Drosophila melanogaster model
Microb Pathog 2020 Dec;149:104528.PMID:33002597DOI:10.1016/j.micpath.2020.104528.
Efflux pumps and β-lactamases are mechanisms of bacterial resistance that exist in Staphylococcus aureus, where both mechanisms are expressed simultaneously in the SA K4100 strain, with its efflux pump being characterized as QacC (Quaternary Ammonium Compounds C). The search for inhibitors of these mechanisms has grown gradually, with research on isolated compounds, including terpenes, which have innumerable biological activities, being common. This study sought to evaluate the antibacterial activity of Terpinolene against the S. aureus K4100 strain, carrying a QacC efflux pump and β-lactamase, as well as to evaluate its toxicity in the Drosophila melanogaster arthropod model. Determination of the Minimum Inhibitory Concentration (MIC) was performed by broth microdilution. Efflux pump inhibition was evaluated by the MIC reduction of Oxacillin and Ethidium Bromide (EtBr). β-Lactamase inhibition was analyzed by the MIC reduction of Ampicillin with Sulbactam. Toxicity was verified by mortality parameters and locomotor assays in D. melanogaster. The results demonstrated that Terpinolene did not present a direct antibacterial activity (MIC ≥ 1024 μg/mL). However, a reduction in MIC was observed when Terpinolene was associated with Oxacillin (161.26-71.83 μg/mL) and EtBr (45.25-32 μg/mL), possibly by a β-lactamase and efflux pump inhibition, thus evidencing a modulatory activity. Terpinolene presented D. melanogaster mortality with an EC50 of 34.6 μL/L within 12 h of exposure. Additionally, Terpinolene presented damage to the locomotor system after the second hour of exposure, with the effect increasing in a concentration-dependent manner. In conclusion, new tests should be carried out to investigate the Terpinolene reinforcement of antibiotic activity and toxic activity mechanisms of action.