3-Pentanol
(Synonyms: 3-戊醇) 目录号 : GC61682
3-Pentanol是植物产生的活性有机化合物，是一种释放出的昆虫性信息素的成分。3-Pentanol可激发植物对农作物中微生物病原体和害虫的免疫力。
Cas No.:584-02-1
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
3-Pentanol is an active organic compound produced by plants and is a component of emitted insect sex pheromones. 3-pentanol elicits plant immunity against microbial pathogens and an insect pest in crop plants[1].
[1]. Geun C Song, et al. Gaseous 3-pentanol primes plant immunity against a bacterial speck pathogen, Pseudomonas syringae pv. tomato via salicylic acid and jasmonic acid-dependent signaling pathways in Arabidopsis. Front Plant Sci. 2015 Oct 6;6:821.
| Cas No. | 584-02-1 | SDF | |
| 别名 | 3-戊醇 | ||
| Canonical SMILES | CCC(O)CC | ||
| 分子式 | C5H12O | 分子量 | 88.15 |
| 溶解度 | 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 | 11.3443 mL | 56.7215 mL | 113.443 mL |
| 5 mM | 2.2689 mL | 11.3443 mL | 22.6886 mL |
| 10 mM | 1.1344 mL | 5.6721 mL | 11.3443 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。
3-Pentanol glycosides from root nodules of the actinorhizal plant Alnus cremastogyne
Phytochemistry 2023 Mar;207:113582.PMID:36596436DOI:10.1016/j.phytochem.2022.113582.
Alnus cremastogyne Burkill (Betulaceae), an actinorhizal plant, can enter a mutualistic symbiosis with Frankia species that leads to the formation of nitrogen fixing root nodules. Some primary metabolites (carbohydrates, dicarboxylic acids, amino acids, citrulline and amides) involved in carbon and nitrogen metabolism in actinorhizal nodules have been identified, while specialized metabolites in A. cremastogyne root nodules are yet to be characterized. In this study, we isolated and identified three undescribed 3-Pentanol glycosides, i.e., 3-pentyl α-l-arabinofuranosyl-(1''→6')-β-d-glucopyranoside, 3-pentyl α-l-rhamnopyranosyl-(1''→6')-β-d-glucopyranoside, and 3-pentyl 6'-(3-hydroxy3-methylglutaryl)-β-d-glucopyranoside, as well as seventeen known compounds from A. cremastogyne root nodules. 3-Pentanol glycosides are abundantly distributed in root nodules, while they are distributed in stems, roots, leaves and fruits at low/zero levels. A. cremastogyne plants treated by root nodule suspension emit 3-Pentanol. This study enriches the knowledge about specialized metabolites in the actinorhizal host, and provides preliminarily information on the signal exchange in the actinorhizal symbiosis between A. cremastogyne and Frankia.
Gaseous 3-Pentanol primes plant immunity against a bacterial speck pathogen, Pseudomonas syringae pv. tomato via salicylic acid and jasmonic acid-dependent signaling pathways in Arabidopsis
Front Plant Sci 2015 Oct 6;6:821.PMID:26500665DOI:10.3389/fpls.2015.00821.
3-Pentanol is an active organic compound produced by plants and is a component of emitted insect sex pheromones. A previous study reported that drench application of 3-Pentanol elicited plant immunity against microbial pathogens and an insect pest in crop plants. Here, we evaluated whether 3-Pentanol and the derivatives 1-pentanol and 2-pentanol induced plant systemic resistance using the in vitro I-plate system. Exposure of Arabidopsis seedlings to 10 μM and 100 nM 3-Pentanol evaporate elicited an immune response to Pseudomonas syringae pv. tomato DC3000. We performed quantitative real-time PCR to investigate the 3-pentanol-mediated Arabidopsis immune responses by determining Pathogenesis-Related (PR) gene expression levels associated with defense signaling through salicylic acid (SA), jasmonic acid (JA), and ethylene signaling pathways. The results show that exposure to 3-Pentanol and subsequent pathogen challenge upregulated PDF1.2 and PR1 expression. Selected Arabidopsis mutants confirmed that the 3-pentanol-mediated immune response involved SA and JA signaling pathways and the NPR1 gene. Taken together, this study indicates that gaseous 3-Pentanol triggers induced resistance in Arabidopsis by priming SA and JA signaling pathways. To our knowledge, this is the first report that a volatile compound of an insect sex pheromone triggers plant systemic resistance against a bacterial pathogen.
Theoretical and Experimental Study of 3-Pentanol Autoignition: Ab Initio Calculation, Shock Tube Experiments, and Kinetic Modeling
J Phys Chem A 2021 Jul 15;125(27):5976-5989.PMID:34213330DOI:10.1021/acs.jpca.1c02713.
3-Pentanol is a potential alternative fuel or a green fuel additive for modern engines. The H-abstraction reactions from 3-Pentanol by H, CH3, HO2, and OH radicals are significant in the 3-Pentanol oxidation process. However, corresponding rate constants are forced to rely on either analogy from sec-butanol or estimation from alkanes due to a lack of direct experimental and theoretical study. In this work, stationary points on the potential energy surfaces (PESs) were calculated with the high-level DLPNO-CCSD(T)/CBS(T-Q)//M06-2X/cc-pVTZ method, which is further used to benchmark against the CBS-QB3 method. Then, the high-pressure limit rate constants for target reactions, over a broad range of temperature (400-2000 K), were calculated with the phase-space theory and conventional transition state theory. A comparison was made between the calculated rate constants and the values available in Carbonnier et al. [ Proc. Combust. Inst. 2019, 37(1), 477-484]. The rate constants for the above H-abstraction reactions in the Carbonnier model were updated with the calculated results, followed by a modification based on the computed results of 3-Pentanol + HO2 to obtain the revised model. Validation against the shock tube (ST) and the jet-stirred reactor (JSR) measurements from the literature proved the revised model an optimal one. Furthermore, using an ST, ignition delay times (IDTs) for the 3-Pentanol/air mixtures were measured spanning a temperature range of 920-1450 K, pressures of 6, 10, and 20 bar, and equivalence ratios of 0.5, 1.0, and 1.5. Generally, IDTs decrease with increasing temperature and reflected shock pressure. Improved predictions to present experimental data were obtained by using the revised model as compared with the Carbonnier model. Finally, sensitivity analysis was conducted using the revised model to gain an in-depth comprehension of the 3-Pentanol autoignition.
3-Pentanol: a new attractant present in volatile emissions from the ambrosia beetle, Megaplatypus mutatus
J Chem Ecol 2008 Nov;34(11):1446-51.PMID:18850328DOI:10.1007/s10886-008-9547-7.
Megaplatypus mutatus (=Platypus mutatus) (Coleoptera: Platypodidae) is an ambrosia beetle that is native to South America. It attacks only standing live trees and causes severe stem breakage and death in commercial poplar (Populus) plantations. Previous work showed that male M. mutatus emits a sex pheromone composed mainly of (+)-sulcatol and sulcatone. We collected male volatile emissions during the hours of maximum emergence by using a specific polar microextraction phase; analyzed the extract by GC-MS; and tested the biological activity of selected compounds in the extract with a walking behavioral assay. Female M. mutatus emerged primarily between 7 and 11 h. In the chemical analyses of volatiles, a third compound, 3-Pentanol, was identified in a small percentage of samples. Walking behavioral bioassays with video image analysis showed that at the doses tested, 3-Pentanol elicited an attractive response from females.
Field evaluation of the bacterial volatile derivative 3-Pentanol in priming for induced resistance in pepper
J Chem Ecol 2014 Aug;40(8):882-92.PMID:25149655DOI:10.1007/s10886-014-0488-z.
Plants are defended from attack by emission of volatile organic compounds (VOCs) that can act directly against pathogens and herbivores or indirectly by recruiting natural enemies of herbivores. However, microbial VOC have been less investigated as potential triggers of plant systemic defense responses against pathogens in the field. Bacillus amyloliquefaciens strain IN937a, a plant growth-promoting rhizobacterium that colonizes plant tissues, stimulates induced systemic resistance (ISR) via its emission of VOCs. We investigated the ISR capacity of VOCs and derivatives collected from strain IN937a against bacterial spot disease caused by Xanthomonas axonopodis pv. vesicatoria in pepper. Of 15 bacterial VOCs and their derivatives, 3-Pentanol, which is a C8 amyl alcohol reported to be a component of sex pheromones in insects, was selected for further investigation. Pathogens were infiltrated into pepper leaves 10, 20, 30, and 40 days after treatment and transplantation to the field. Disease severity was assessed 7 days after transplantation. Treatment with 3-Pentanol significantly reduced disease severity caused by X. axonopodis and naturally occurring Cucumber mosaic virus in field trials over 2 years. We used quantitative real-time polymerase chain analysis to examine Pathogenesis-Related genes associated with salicylic acid (SA), jasmonic acid (JA), and ethylene defense signaling. The expression of Capsicum annuum Pathogenesis-Related protein 1 (CaPR1), CaPR2, and Ca protease inhibitor2 (CaPIN2) increased in field-grown pepper plants treated with 3-Pentanol. Taken together, our results show that 3-Pentanol triggers induced resistance by priming SA and JA signaling in pepper under field conditions.