1-Octen-3-ol
(Synonyms: 1-辛烯-3-醇) 目录号 : GC49818
A volatile organic compound
Cas No.:3391-86-4
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
1-Octen-3-ol is a volatile organic compound (VOC) that has been found in fungi and plants.1 It has also been found in oxen breath and human sweat and is an attractant for Ochlerotatus, Psorophora, Anopheles, and Coquillettidia mosquitoes but a repellant for Culex mosquitoes.1,2 1-Octen-3-ol (3 and 10 ppm) inhibits dopamine uptake in HEK cells expressing the human dopamine transporter (HEK-DAT cells).3 It induces dopaminergic neuron loss and locomotor deficits in, as well as reduces survival of, D. melanogaster when administered via inhalation at a dose of 0.5 ppm.
1.Xu, P., Zhu, F., Buss, G.K., et al.1-Octen-3-ol ? the attractant that repelsF1000Res.4156(2015) 2.Kline, D.L., Allan, S.A., Bernier, U.R., et al.Evaluation of the enantiomers of 1-octen-3-ol and 1-octyn-3-ol as attractants for mosquitoes associated with a freshwater swamp in Florida, U.S.AMed. Vet. Entomol.21(4)323-331(2007) 3.Inamdar, A.A., Hossain, M.M., Bernstein, A.I., et al.Fungal-derived semiochemical 1-octen-3-ol disrupts dopamine packaging and causes neurodegenerationProc. Natl. Acad. Sci. USA110(48)19561-19566(2013)
| Cas No. | 3391-86-4 | SDF | Download SDF |
| 别名 | 1-辛烯-3-醇 | ||
| Canonical SMILES | OC(CCCCC)C=C | ||
| 分子式 | C8H16O | 分子量 | 128.2 |
| 溶解度 | DMF: 33 mg/mL,DMSO: 33 mg/mL,Ethanol: 33 mg/mL,PBS (pH 7.2): 0.30 mg/mL | 储存条件 | -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 | 7.8003 mL | 39.0016 mL | 78.0031 mL |
| 5 mM | 1.5601 mL | 7.8003 mL | 15.6006 mL |
| 10 mM | 0.78 mL | 3.9002 mL | 7.8003 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。
1-Octen-3-ol is formed from its primeveroside after mechanical wounding of soybean leaves
Plant Mol Biol 2022 Jul;109(4-5):551-561.PMID:34837579DOI:10.1007/s11103-021-01226-9.
Hydrolysis of 1-octen-3-yl β-primeveroside implemented by a system with high structure-specificity is accountable for the rapid formation of 1-Octen-3-ol from soybean leaves after mechanical wounding. 1-Octen-3-ol is a volatile compound ubiquitous in fungi; however, a subset of plant species also has the ability to form 1-Octen-3-ol. Owing to its volatile nature, it has been anticipated that 1-Octen-3-ol is associated with the effort of the emitter to control the behavior of the surrounding organisms; however, its ecological significance and the enzymes involved in its biosynthesis have not been fully elucidated, particularly in plants. We previously found that soybean (Glycine max) seeds contain 1-octen-3-yl β-primeveroside (pri). To elucidate the physiological significance and the biosynthesis of 1-Octen-3-ol in plants, changes in the amount of 1-octen-3-yl pri during development of soybean plants was examined. A high 1-octen-3-yl pri level was found in young developing green organs, such as young leaves and sepals. Treatment of soybean leaves with methyl jasmonates resulted in a significant increase in the amount of 1-octen-3-yl pri; suggesting its involvement in defense responses. Although 1-Octen-3-ol was below the detection limit in intact soybean leaves, mechanical damage to the leaves caused rapid hydrolysis of almost all 1-octen-3-yl pri to liberate volatile 1-Octen-3-ol. Under the same conditions, the other glycosides, including isoflavone glycoside and linalool diglycoside, were hardly hydrolyzed. Therefore, the enzyme system to liberate aglycone from glycosides in soybean leaves should have strict substrate specificity. 1-Octen-3-yl pri might function as a storage form of volatile 1-Octen-3-ol for immediate response against stresses accompanying tissue wounding.
Application of the mushroom volatile 1-Octen-3-ol to suppress a morel disease caused by Paecilomyces penicillatus
Appl Microbiol Biotechnol 2022 Jun;106(12):4787-4799.PMID:35759038DOI:10.1007/s00253-022-12038-2.
Morels (Morchella spp.) are of great economic and scientific value. Paecilomyces penicillatus can cause white mold disease (WMD) widely emerging on morel ascocarps and is also a potential factor causing morel fructification failure. 1-Octen-3-ol is a mushroom volatile compound with broad-spectrum antimicrobial activities. This study aimed to control the morel disease caused by P. penicillatus through suppressing P. penicillatus in the soil cultivated with Morchella sextelata using 1-Octen-3-ol. Safe concentration of 1-Octen-3-ol was estimated by comparing its inhibitory effect against P. penicillatus and M. sextelata, respectively, with mycelium-growth experiments on agar plates. The results showed that M. sextelata possesses a higher tolerance to 1-Octen-3-ol than P. penicillatus with a 1-Octen-3-ol concentration between 0 and 200 µL/L. Based on that, a sandy soil was supplemented with low (50 µL/L) or high concentration (200 µL/L) of 1-Octen-3-ol. The effects of 1-Octen-3-ol on soil microbial communities, WMD incidence, and morel yield were investigated. Compared to the non-supplemented control group, the incidence of WMD and the proportion of Paecilomyces in the soils of low- and high-concentration treatment groups were significantly decreased, corresponding to a significant increase in morel ascocarp yield. It suggests that 1-Octen-3-ol effectively suppressed P. penicillatus in the soil, thereby reducing the severity of WMD and improving the morel yield. The diversity of soil bacterial communities was also altered by 1-Octen-3-ol supplement. The proportion of Rhodococcus spp. in the soil was positively correlated with the 1-Octen-3-ol concentration and ascocarp yield, suggesting its potential role in improving morel yield. KEY POINTS: • A novel method for morel disease suppression was proposed. • Paecilomyces in soil affects white mold disease and fructification yield of morel. • 1-Octen-3-ol suppresses Paecilomyces and alters bacterial community in soil.
Inhibition of cholesterol biosynthesis promotes the production of 1-Octen-3-ol through mevalonic acid
Food Res Int 2022 Aug;158:111392.PMID:35840187DOI:10.1016/j.foodres.2022.111392.
1-Octen-3-ol makes an important contribution to meat flavor. The goal of this study was to identify the metabolic pathways of 1-Octen-3-ol formation in meat. We found 218 metabolites associated with 1-Octen-3-ol content in 20 samples of chicken meat, including mevalonic acid (positive correlation), corticosterone (negative correlation), and other lipids and lipid-like molecules. Among these 218 metabolites, 17 metabolites were differentially expressed in different 1-Octen-3-ol content groups. Similarly, 37 genes were not only differentially expressed, but were significantly correlated with 1-Octen-3-ol. The regulation of HSP90AA1, PTPN9, and other genes converted more mevalonic acid to 1-Octen-3-ol. Meanwhile, mevalonic acid, a key material in the synthesis of cholesterol, caused a decrease in corticosterone content, affecting ZNF414 and KLF15 gene expression. These findings reveal the effect of cholesterol on 1-Octen-3-ol content, as well as a positive regulation of mevalonic acid on the production of 1-Octen-3-ol in chicken meat.
1-Octen-3-ol - the attractant that repels
F1000Res 2015 Jun 18;4:156.PMID:26543554DOI:10.12688/f1000research.6646.1.
Since the discovery in the early 1980s that 1-Octen-3-ol, isolated from oxen breath, attracts tsetse fly, there has been growing interest in exploring the use of this semiochemical as a possible generic lure for trapping host-seeking mosquitoes. Intriguingly, traps baited with 1-Octen-3-ol captured significantly more females of the malaria mosquito, Anopheles gambiae, and the yellow fever mosquito, Aedes aegypti, than control traps, but failed to attract the southern house mosquito, Culex quinquefasciatus. Additionally, it has been demonstrated that this attractant is detected with enantioselective odorant receptors (ORs) expressed only in maxillary palps. On the basis of indoor behavioral assays it has even been suggested that 1-Octen-3-ol might be a repellent to the southern house mosquito. Our approach was two-prong, i.e., to isolate 1-octen-3-ol-sensitive ORs expressed in maxillary palps and antennae of southern house female mosquito, and test the hypothesis that this semiochemical is a repellent. An OR with high transcript levels in maxillary palps, CquiOR118b, showed remarkable selectivity towards ( R)-1-octen-3-ol, whereas an OR expressed in antennae, CquiOR114b, showed higher preference for ( S)-1-octen-3-ol than its antipode. Repellency by a surface landing and feeding assay showed that not only racemic, but enantiopure ( R)- and ( S)-1-octen-3-ol are repellents at 1% dose thus suggesting the occurrence of other ( S)-1-octen-3-ol-sensitive OR(s). Female mosquitoes with ablated maxillary palps were repelled by 1-Octen-3-ol, which implies that in addition to OR(s) in the maxillary palps, antennal OR(s) are essential for repellency activity.
The oxylipin messenger 1-Octen-3-ol induced rapid responses in kelp Macrocystis pyrifera
Physiol Plant 2021 Jul;172(3):1641-1652.PMID:33547806DOI:10.1111/ppl.13358.
Oxylipins are important oxygenated derivatives of fatty acids that regulate a variety of plant physiological and pathological processes in response to specific external challenges. A large body of evidence has indicated that algae can also produce a surprisingly diverse array of volatile oxylipins, yet little is known about the roles of volatile oxylipins as defense signals in macroalgae. In this study, the kelp Macrocystis pyrifera was treated by the oxylipin messenger 1-Octen-3-ol and then a genome-wide gene expression profile and fatty acid spectrum analysis were performed. We found that M. pyrifera responded rapidly to the exposure of the oxylipin messenger 1-Octen-3-ol. It regulated the expression levels of genes mainly involved in signal transduction, lipid metabolism, oxidation prevention, cell wall synthesis, photosynthesis, and development. Moreover, 1-Octen-3-ol treatments decreased several types of total fatty acid contents and increased free fatty acid contents, especially for the C18 and C20 fatty acids. In addition, it decreased the content of indole-3-acetic acid, abscisic acid, and zeatin and increased the gibberellic acid content. Our findings demonstrated that 1-Octen-3-ol is an available inducer for M. pyrifera, which is capable of rapidly upregulating kelp's defense response.