(Z)-9-Hexadecenol
(Synonyms: 3-氨基-6-甲基吡啶-2(1H)-酮) 目录号 : GC46356
An unsaturated long-chain fatty alcohol with diverse biological activities
Cas No.:10378-01-5
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
(Z)-9-Hexadecenol is an unsaturated long chain fatty alcohol that has been found in pheromone gland extracts from H. assulta and has diverse biological activities.1,2,3 It is virucidal against herpes simplex virus 2 (HSV-2) when used at a concentration of 10 mM.2 (Z)-9-Hexadecenol is active against the bacterium S. mutans (MIC = 1.56 μg/ml).3 It decreases flight, upwind, close, landing, and copulatory behavior induced by an H. assulta pheromone blend in male H. assulta moths in a wind tunnel assay.1
1.Xu, M., Guo, H., Hou, C., et al.Olfactory perception and behavioral effects of sex pheromone gland components in Helicoverpa armigera and Helicoverpa assultaSci. Rep.622998(2016) 2.Hilmarsson, H., KristmundsdÓttir, T., and Thormar, H.Virucidal activities of medium- and long-chain fatty alcohols, fatty acids and monoglycerides against herpes simplex virus types 1 and 2: Comparison at different pH levelsAPMIS113(1)58-65(2005) 3.Hattori, M., Miyachi, K., Hada, S., et al.Effects of long-chain fatty acids and fatty alcohols on the growth of Streptococcus mutansChem. Pharm. Bull. (Tokyo)35(8)3507-3510(1987)
| Cas No. | 10378-01-5 | SDF | |
| 别名 | 3-氨基-6-甲基吡啶-2(1H)-酮 | ||
| Canonical SMILES | OCCCCCCCC/C=C\CCCCCC | ||
| 分子式 | C16H32O | 分子量 | 240.4 |
| 溶解度 | DMF: 30 mg/ml,DMSO: 30 mg/ml,Ethanol: 30 mg/ml,Ethanol:PBS (pH 7.2) (1:2): 0.33 mg/ml | 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 | 4.1597 mL | 20.7987 mL | 41.5973 mL |
| 5 mM | 0.8319 mL | 4.1597 mL | 8.3195 mL |
| 10 mM | 0.416 mL | 2.0799 mL | 4.1597 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。
Comparison of functions of pheromone receptor repertoires in Helicoverpa armigera and Helicoverpa assulta using a Drosophila expression system
Insect Biochem Mol Biol 2022 Feb;141:103702.PMID:34942332DOI:10.1016/j.ibmb.2021.103702.
Helicoverpa armigera and H. assulta are sympatric closely related species sharing two sex pheromone components, (Z)-11-hexadecenal (Z11-16:Ald) and (Z)-9-hexadecenal (Z9-16:Ald) but in opposite ratios, 97:3 and 3:97 respectively. This feature makes them a feasible model for studying the evolution of pheromone coding mechanisms of lepidopteran insects. Despite a decade-long study to deorphanize the pheromone receptor (PR) repertoires of the two species, the comparison of the function of all PR orthologs between the two species is incomplete. Moreover, the ligands of OR14 and OR15 have so far not been found, likely due to the missing of the active ligand(s) in the compound panel and/or incompatibility of heterologous expression systems used. In the present study, we expressed the PR repertoires of both Helicoverpa species in Drosophila T1 neurons to comparatively study the function of PRs. Among those PRs, OR13, OR6, and OR14 of both species are functionally conserved and narrowly tuned, and the T1 neurons expressing each of them respond to Z11-16:Ald, (Z)-9-Hexadecenol (Z9-16:OH), and (Z)-11-hexadecenyl acetate (Z11-16:Ac), respectively. While HarmOR16-expressing neurons respond strongly to (Z)-9-tetradecenal (Z9-14:Ald) and (Z)-11-hexadecenol (Z11-16:OH), the neurons expressing HassOR16 mainly respond to Z9-14:Ald and also weakly respond to (Z)-9-tetradecenol (Z9-14:OH). Moreover, HarmOR14b-expressing neurons are activated by Z9-14:Ald, whereas HassOR14b-expressing neurons are sensitive to Z9-16:Ald, Z9-14:Ald, and (Z)-9-Hexadecenol (Z9-16:OH). In addition, HarmOR15-expressing neurons are selectively responsive to Z9-14:Ald. However, the Drosophila T1 neurons expressing either HarmOR11 or HassOR11 are silent to all of the compounds tested. In summary, except for OR11, we have deorphanized all the PRs of these two Helicoverpa species using a Drosophila expression system and a large panel of pheromone compounds, thereby providing a valuable reference for parsing the code of peripheral coding of pheromones.
Olfactory perception and behavioral effects of sex pheromone gland components in Helicoverpa armigera and Helicoverpa assulta
Sci Rep 2016 Mar 15;6:22998.PMID:26975244DOI:10.1038/srep22998.
Two sympatric species Helicoverpa armigera and Helicoverpa assulta use (Z)-11-hexadecenal and (Z)-9-hexadecenal as sex pheromone components in reverse ratio. They also share several other pheromone gland components (PGCs). We present a comparative study on the olfactory coding mechanism and behavioral effects of these additional PGCs in pheromone communication of the two species using single sensillum recording, in situ hybridization, calcium imaging, and wind tunnel. We classify antennal sensilla types A, B and C into A, B1, B2, C1, C2 and C3 based on the response profiles, and identify the glomeruli responsible for antagonist detection in both species. The abundance of these sensilla types when compared with the number of OSNs expressing each of six pheromone receptors suggests that HarmOR13 and HassOR13 are expressed in OSNs housed within A type sensilla, HarmOR14b within B and C type sensilla, while HassOR6 and HassOR16 within some of C type sensilla. We find that for H. armigera, (Z)-11-hexadecenol and (Z)-11-hexadecenyl acetate act as behavioral antagonists. For H. assulta, instead, (Z)-11-hexadecenyl acetate acts as an agonist, while (Z)-9-Hexadecenol, (Z)-11-hexadecenol and (Z)-9-hexadecenyl acetate are antagonists. The results provide an overall picture of intra- and interspecific olfactory and behavioral responses to all PGCs in two sister species.
Pheromone biosynthetic pathways in the moths Heliothis subflexa and Heliothis virescens
Arch Insect Biochem Physiol 2005 Jun;59(2):53-8.PMID:15898118DOI:10.1002/arch.20051.
Sex pheromones of many moth species have relatively simple structures consisting of a hydrocarbon chain with a functional group and one to several double bonds. These sex pheromones are derived from fatty acids through specific biosynthetic pathways. We investigated the incorporation of deuterium-labeled tetradecanoic, hexadecanoic, and octadecanoic acid precursors into pheromone components of Heliothis subflexa and Heliothis virescens. The two species utilize (Z)11-hexadecenal as the major pheromone component, which is produced by Delta11 desaturation of hexadecanoic acid. H. subflexa also produced (Z)11-hexadecanol and (Z)-11-hexadecenyl acetate via Delta11 desaturation. In H. subflexa, octadecanoic acid was used to biosynthesize the minor pheromone components (Z)9-hexadecenal, (Z)9-hexadecenol, and (Z)9-hexadecenyl acetate. These minor components are produced by Delta11 desaturation of octadecanoic acid followed by one round of chain-shortening. In contrast, H. virescens used hexadecanoic acid as a substrate to form (Z)11-hexadecenal and (Z)11-hexadecenol and hexadecenal. H. virescens also produced (Z)9-tetradecenal by Delta11 desaturation of the hexadecanoic acid followed by one round of chain-shortening and reduction. Tetradecanoic acid was not utilized as a precursor to form Z9-14:Ald in H. virescens. This labeling pattern indicates that the Delta11 desaturase is the only active desaturase present in the pheromone gland cells of both species.
Identification of an attractant for the caneborerSesamia grisescens walker (Lepidoptera: Noctuidae)
J Chem Ecol 1995 Oct;21(10):1409-20.PMID:24233673DOI:10.1007/BF02035142.
The composition of the sex pheromone ofSesamia grisescens was investigated using gas chromatography, electroantennograms, and field trapping. (Z)-11-Hexadecenyl acetate and (Z)-11-hexadecenol were identified in field tests as the major attractants. Trapping trials identified a 3:2 blend of these compounds as the most effective bait. Gas chromatography indicated the presence of hexadecyl acetate. (Z)-9-hexadecenyl acetate, (Z)-9-Hexadecenol, and (E)-11-hexadecenyl acetate in the pheromone gland, but these compounds had no significant effect on trap catches when added to the major components. Traps baited with the major components in a 1:1 ratio caught more male moths than traps baited with virgin females.