The following chemicals were purchased at highest purities available from Sigma Aldrich, Bangalore, India: 2-methyltetrahydro-3-furanone, acetic acid, benzaldehyde, 1-octanol, (R)-1-octen-3-ol, ethyl butyrate, ethyl acetate, geranyl acetate, methyl salicylate, methyl laurate, isopentyl acetate, hexanoic acid, 2-methylphenol, geosmin, butyraldehyde, 1,4-diaminobutane, phenyl acetalydehyde, phenylethylamine, pyridine, ammonia solution and mineral oil. 11-cis-vaccenyl acetate was purchased from Cayman Chemical Company, Michigan, United States. Cis-3-hexenyl acetate, 2,3-butanedione, butyric acid, linalool, and acetophenone were purchased from Fluka, Sigma-Aldrich, Bangalore, India. The compound 1-hexanol was purchased from TCI, nonanal was purchased from Acros Organics. Propionic acid was obtained as a gift from the Max Planck Institute for Chemical Ecology, Jena, Germany. Fluo-4AM was purchased from Life Technologies, Stockholm, Sweden.
Cis 3 hexenyl acetate
Manufactured by Merck Group
Sourced in United States
Cis-3-hexenyl acetate is a colorless liquid with a characteristic green, floral aroma. It is commonly used as a flavoring and fragrance ingredient in various industries.
Automatically generated - may contain errors
Lab products found in correlation
Methyl salicylate, by Merck Group (2 mentions)
Linalool, by Merck Group (2 mentions)
Benzaldehyde, by Merck Group (2 mentions)
Geosmin, by Merck Group (2 mentions)
Limonene, by Merck Group (2 mentions)
Cis 3 hexen 1 ol, by Merck Group (2 mentions)
β ionone, by Merck Group (2 mentions)
Geranyl acetate, by Merck Group (1 mentions)
Ethyl butyrate, by Merck Group (1 mentions)
Methyl laurate, by Merck Group (1 mentions)
Isopentyl acetate, by Merck Group (1 mentions)
Butyraldehyde, by Merck Group (1 mentions)
Phenylethylamine, by Merck Group (1 mentions)
Acetophenone, by Merck Group (1 mentions)
Nonanal, by Thermo Fisher Scientific (1 mentions)
2 methylphenol, by Merck Group (1 mentions)
Butyric acid, by Merck Group (1 mentions)
1 4 diaminobutane, by Merck Group (1 mentions)
1 octanol, by Merck Group (1 mentions)
Fluo 4 am, by Thermo Fisher Scientific (1 mentions)
6 protocols using cis 3 hexenyl acetate
1
Comprehensive Chemical Compound Synthesis
2
Insecticide Synergist Extraction Protocol
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Methomyl (purity 98%) was obtained from Jiangsu Jinghong Chemical Co. Ltd. (Yancheng, China). Piperonyl butoxide (PBO, purity 98%) was purchased from Nanchang Yangpu Natural Essence and Spice Co. Ltd. (Nanchang, China). Limonene, nerolidol, 2-heptanone, cis-3-hexenyl acetate, NADPH, glycerol, 7-ethoxycoumarin (7-EC), 7-hydroxycoumarin (7-HC), phenylmethylsulfonyl (PMSF), dithiothreitol (DTT), phenylthiourea (PTU) and bovine serum albumin (BSA) were obtained from Sigma (St. Louis, MO, USA). Acetone was purchased from Shanghai Ling Feng Chemical Reagent Co. Ltd. (Shanghai, China).
3
Preparation of Bitter Compound Solutions
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Ethanethiol, 2-Decanone, Diethyl disulfide, 2,5-Dimethylthiophene, trans-2-Pentenoic acid, cis-3-Hexenyl acetate and quinine sulfate were purchased from Sigma (CAS Numbers: 75-08-1, 693-54-9, 110-81-6, 638-02-8, 13991-37-2, 3681-71-8 and 207671-44-1 respectively). All compounds were dissolved to a final concentration of 0.5 mM in double distilled water (Millipore-filtered). The solutions concentration was selected to be 0.5 mM, higher than reported detection thresholds of known bitter compounds, (such as PROP and quinine64 (link)), and safe.
4
Dose-dependent Behavioral and Electrophysiological Response to E-beta-farnesene in Pea Aphids
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E-beta-farnesene (Bedoukian, Danbury, CT, USA) was diluted in hexane in decadic steps from 0.1 ng/μL to 10 μg/μL. Ten microlitres of a solution was applied on a filter paper inside a Pasteur pipette. For olfactometer experiments, four amounts from 0.01 μg to 10 μg of EBF on the filter paper were used. These amounts were shown in preliminary experiments to elicit dose-dependent repulsive responses in various pea aphid clones (data not shown). For electroantennogram (EAG) recordings, a dose-response curve was obtained with doses from 1 ng to 100 μg on the filter paper. In EAG recordings, we also stimulated the antenna with 1-mg cis-3-hexenyl acetate (Sigma-Aldrich, Saint Qentin Fallavier, France), a major component of pea odour [32 (link)]. As controls, Pasteur pipettes containing a filter paper with 10 μL of the solvent hexane were used.
5
Detailed Volatile Organic Compound Analysis
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All VOC standards were purchased from Sigma-Aldrich (St. Louis, MO, United States): 1-penten-3-ol, 1-penten-3-one, 3-pentanone, α-caryophyllene, α-farnesene, α-pinene, β-caryophyllene, β-farnesene, β-ionone, benzaldehyde, cis-3-hexen-1-ol, cis-3-hexenyl acetate, eugenol, hexyl acetate, jasmone, limonene, linalool, methyl jasmonate, methyl salicylate, ocimene, trans-2-hexen-1-al. All VOC standards were diluted in 100% methanol.
6
Analytical Standards for Volatile Organic Compounds
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Analytical standards (>98% purity) of 2-methylisoborneol, geosmin, 2-isopropyl methoxypyrazine (IPMP), 2-isobutyl methoxypyrazine (IBMP), 2,4,6-trichloroanisole (2,4,6-TCA), 2,4,6-tribromoanisole (2,4,6-TBA), β-cyclocitral, β-ionone, cis-3-hexenyl acetate (c3HA), cis-3-hexen-1-ol (c3HO), dimethyl disulfide (DMDS), dimethyl trisulfide (DMTS), 2,6-nonadienal (2,6-ND), 2,4-heptadienal (2,4-HD), 2-ethyl-2-methyl-1,3-dioxolane (EMD), hexanal, indole, naphthalene-d8 (N-d8) and 2,4,6-trichloroanisole-d5 (2,4,6-TCA-d5) were obtained from Sigma-Aldrich (St. Louis, MO, USA). 2,3,6-trichloroanisole (2,3,6-TCA) was purchased from Santa Cruz Biotechnology (Dallas, TX, USA). Stock and working standard solutions were prepared in methanol (≥99.9% purity, Sigma-Aldrich, St. Louis, MO) and were stored at 4°C. Reagent grade sodium chloride (NaCl) was purchased in bulk (12 kg plastic drum) from EMD Millipore (Burlington, MA, USA).
For SPME, 1 cm dual-coated (50/30 µm) DVB/CAR/PDMS fibers were purchased from Supelco (Bellefonte, PA, USA). GC inlet liners that are compatible with SPME fibers were purchased from Agilent Technologies (Santa Clara, CA, USA). 20 mL amber headspace screw-top vials with PTFE/silicone magnetic caps were used for holding 10 mL samples for GC-MS/MS analysis (Agilent Technologies, USA).
For SPME, 1 cm dual-coated (50/30 µm) DVB/CAR/PDMS fibers were purchased from Supelco (Bellefonte, PA, USA). GC inlet liners that are compatible with SPME fibers were purchased from Agilent Technologies (Santa Clara, CA, USA). 20 mL amber headspace screw-top vials with PTFE/silicone magnetic caps were used for holding 10 mL samples for GC-MS/MS analysis (Agilent Technologies, USA).
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