2-Tridecanone
(Synonyms: 2-十三烷酮) 目录号 : GC61919
2-Tridecanone 是一种从野生番茄 Lycopersicon hirsutum f. glabratum 中分离出非生物碱杀虫剂。2-Tridecanone 是一种挥发性的有机化合物。
Cas No.:593-08-8
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
2-Tridecanone, a nonalkaloid insecticide, is isolated from the wild tomato Lycopersicon hirsutum f. glabratum. 2-Tridecanone is a volatile organic compound[1][2].
References:
[1]. Williams WG, et, al. 2-Tridecanone: A Naturally Occurring Insecticide from the Wild Tomato Lycopersicon hirsutum f.glabratum. Science. 1980 Feb 22;207(4433):888-9.
[2]. Antonious GF, et, al. 2-undecanone and 2-tridecanone in field-grown onion. J Environ Sci Health B. 2013;48(4):302-7.
| Cas No. | 593-08-8 | SDF | |
| 别名 | 2-十三烷酮 | ||
| Canonical SMILES | CCCCCCCCCCCC(C)=O | ||
| 分子式 | C13H26O | 分子量 | 198.35 |
| 溶解度 | DMSO : 50 mg/mL (252.08 mM; Need ultrasonic) | 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 | 5.0416 mL | 25.208 mL | 50.4159 mL |
| 5 mM | 1.0083 mL | 5.0416 mL | 10.0832 mL |
| 10 mM | 0.5042 mL | 2.5208 mL | 5.0416 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。
Corynebacterium sp. 2-TD Mediated Toxicity of 2-Tridecanone to Helicoverpa armigera
Toxins (Basel) 2022 Oct 11;14(10):698.PMID:36287967DOI:10.3390/toxins14100698.
Cotton bollworm (Helicoverpa armigera) is a Lepidopteran noctuid pest with a global distribution. It has a wide range of host plants and can harm cotton, tomato, tobacco, and corn, as well as other crops. H. armigera larvae damage the flower buds, flowers, and fruits of tomato and cause serious losses to tomato production. Tomato uses the allelochemical 2-Tridecanone to defend against this damage. So far, there have been no reports on whether the adaptation of H. armigera to 2-Tridecanone is related to its symbiotic microorganisms. Our study found that Corynebacterium sp. 2-TD, symbiotic bacteria in H. armigera, mediates the toxicity of the 2-Tridecanone to H. armigera. Corynebacterium sp. 2-TD, which was identified by 16S rDNA gene sequence analysis, was screened out using a basal salt medium containing a unique carbon source of 2-Tridecanone. Then, Corynebacterium sp. 2-TD was confirmed to be distributed in the gut of H. armigera by quantitative PCR (qPCR) and fluorescence in situ hybridization (FISH). The survival rate of H. armigera increased by 38.3% under 2-Tridecanone stress after inoculation with Corynebacterium sp. 2-TD. The degradation effect of Corynebacterium sp. 2-TD on 2-Tridecanone was verified by ultra-high-performance liquid chromatography (UPLC). Our study is the first to report the isolation of gut bacteria that degrade 2-Tridecanone from the important agricultural pest H. armigera and to confirm bacterial involvement in host adaptation to 2-Tridecanone, which provides new insights into the adaptive mechanism of agricultural pests to host plants.
RIFM fragrance ingredient safety assessment, 2-Tridecanone, CAS Registry Number 593-08-8
Food Chem Toxicol 2022 Dec;169 Suppl 1:113408.PMID:36087617DOI:10.1016/j.fct.2022.113408.
The existing information supports the use of this material as described in this safety assessment. 2-Tridecanone was evaluated for genotoxicity, repeated dose toxicity, reproductive toxicity, local respiratory toxicity, photoirritation/photoallergenicity, skin sensitization, and environmental safety. Data from read-across analog 2-heptanone (CAS # 110-43-0) show that 2-Tridecanone is not expected to be genotoxic and provide a calculated Margin of Exposure (MOE) > 100 for the repeated dose toxicity and reproductive toxicity endpoints. Data from read-across analog 2-heptanone (CAS # 110-43-0) show that there are no safety concerns for 2-Tridecanone for skin sensitization under the current declared levels of use. The photoirritation/photoallergenicity endpoints were evaluated based on ultraviolet/visible (UV/Vis) spectra; 2-Tridecanone is not expected to be photoirritating/photoallergenic. The local respiratory toxicity endpoint was evaluated using the Threshold of Toxicological Concern (TTC) for a Cramer Class II material, and the exposure to 2-Tridecanone is below the TTC (0.47 mg/day). The environmental endpoints were evaluated; 2-Tridecanone was found not to be Persistent, Bioaccumulative, and Toxic (PBT) as per the International Fragrance Association (IFRA) Environmental Standards, and its risk quotients, based on its current volume of use in Europe and North America (i.e., Predicted Environmental Concentration/Predicted No Effect Concentration [PEC/PNEC]), are <1.
2-Tridecanone impacts surface-associated bacterial behaviours and hinders plant-bacteria interactions
Environ Microbiol 2018 Jun;20(6):2049-2065.PMID:29488306DOI:10.1111/1462-2920.14083.
Surface motility and biofilm formation are behaviours which enable bacteria to infect their hosts and are controlled by different chemical signals. In the plant symbiotic alpha-proteobacterium Sinorhizobium meliloti, the lack of long-chain fatty acyl-coenzyme A synthetase activity (FadD) leads to increased surface motility, defects in biofilm development and impaired root colonization. In this study, analyses of lipid extracts and volatiles revealed that a fadD mutant accumulates 2-Tridecanone (2-TDC), a methylketone (MK) known as a natural insecticide. Application of pure 2-TDC to the wild-type strain phenocopies the free-living and symbiotic behaviours of the fadD mutant. Structural features of the MK determine its ability to promote S. meliloti surface translocation, which is mainly mediated by a flagella-independent motility. Transcriptomic analyses showed that 2-TDC induces differential expression of iron uptake, redox and stress-related genes. Interestingly, this MK also influences surface motility and impairs biofilm formation in plant and animal pathogenic bacteria. Moreover, 2-TDC not only hampers alfalfa nodulation but also the development of tomato bacterial speck disease. This work assigns a new role to 2-TDC as an infochemical that affects important bacterial traits and hampers plant-bacteria interactions by interfering with microbial colonization of plant tissues.
2-undecanone and 2-Tridecanone in field-grown onion
J Environ Sci Health B 2013;48(4):302-7.PMID:23374049DOI:10.1080/03601234.2013.743790.
A field study was conducted to investigate the impact of soil amendments on concentrations of two volatile organic compounds, 2-undecanone and 2-Tridecanone, in onion bulbs. The soil in five plots was mixed with sewage sludge, five plots were mixed with yard waste compost, five plots were mixed with laying hen manure each at 15 t acre(-1), and five unamended plots that never received soil amendments were used for comparison purposes. Plots (n = 20) were planted with onion, Allium cepa L. var. Super Star-F1 bulbs. Gas chromatographic/mass spetrometric (GC/MS) analyses of mature onion bulbs crude extracts revealed the presence of two major fragment ions that correspond to 2-undecanone and 2-Tridecanone. Soil amended with yard waste compost enhanced 2-undecanone and 2-Tridecanone production by 31 and 59%, respectively. Soil amended with chicken manure enhanced 2-undecanone and 2-Tridecanone production by 28 and 43%, respectively. Concentrations of 2-undecanone and 2-Tridecanone were lowest in onion bulbs of plants grown in sewage sludge and unamended soil, respectively. The increased concentrations of 2-undecanone and 2-Tridecanone in onion bulbs may provide a protective character against insect and spider mite attack in field grown onions.
Identification of the 2-Tridecanone cis-acting element in the promoter of cytochrome P450 CYP6B7 in Helicoverpa armigera
Insect Sci 2018 Dec;25(6):959-968.PMID:28497882DOI:10.1111/1744-7917.12479.
The expression level of cytochrome P450 genes in insects can be induced by plant allelochemicals, which is important for insects to adapt to host plants. Cytochrome P450 CYP6B7 has been reported to be involved in pyrethroid insecticide resistance in Helicoverpa armigera, and its transcription level was induced by some inducers. Currently, the regulatory mechanism of the induced expression of CYP6B7 remains unknown, although it is very important for understanding the detoxification mechanism to allelochemicals in host plants. The objective of the present study was to investigate the cis-acting element in the promoter of CYP6B7 mediating the inducible up-regulation of CYP6B7 in H. armigera by 2-Tridecanone. The promoter region of CYP6B7 was cloned by genome walking technique and analyzed by transient transfection assay. Progressive 5' deletion of the promoter region of CYP6B7 revealed that the relative luciferase activity of construct -320/+232 could be significantly induced by 2-Tridecanone. Further stepwise deletion between -320 and -238 bp found that construct -292/+232 could also be significantly induced by 2-Tridecanone, but the adjacent construct -256/+232 could not, suggesting the essential role of the sequence between -292 and -257 bp for 2-Tridecanone induction. Nucleotide mutations between -292 and -281 bp had no influence on the induction effect by 2-Tridecanone, but nucleotide mutations between -280 and -257 bp significantly decreased the induction effect. These results demonstrated that the cis-acting element for 2-Tridecanone induction was between -280 and -257 bp in the promoter of CYP6B7.