Geranyl acetate

Manufactured by Merck Group

Sourced in United States, Germany

Geranyl acetate is a colorless, oily liquid chemical compound. It is the acetate ester of the alcohol geraniol. Geranyl acetate is used as a fragrance and flavor ingredient in various consumer products.

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Lab products found in correlation

Linalool, by Merck Group (10 mentions) Geraniol, by Merck Group (10 mentions) Citral, by Merck Group (9 mentions) α terpineol, by Merck Group (8 mentions) Myrcene, by Merck Group (7 mentions) Limonene, by Merck Group (6 mentions) α pinene, by Merck Group (5 mentions) P cymene, by Merck Group (4 mentions) Camphene, by Merck Group (4 mentions) γ terpinene, by Merck Group (4 mentions) β pinene, by Merck Group (4 mentions) Nerol, by Merck Group (4 mentions) Butyric acid, by Merck Group (3 mentions) Caryophyllene oxide, by Merck Group (3 mentions) Camphor, by Merck Group (3 mentions) Cis 3 hexen 1 ol, by Merck Group (3 mentions) 2 phenylethanol, by Merck Group (3 mentions) Linalyl acetate, by Merck Group (3 mentions) Ethyl hexanoate, by Merck Group (3 mentions) Hexanoic acid, by Merck Group (2 mentions)

23 protocols using geranyl acetate

Repellent Terpenoid Compounds Evaluation

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The molecules evaluated in this research were selected previously from Essential Oils (EOs) extracted from plants with potential repellent activity and tested by Centro de Investigaciones en Enfermedades Tropicales (CINTROP). The terpenoid compounds selected and with efficient repellent activity were the secondary metabolites: Geranyl acetate, α-bisabolol, and Nerolidol, purchased from Merck ©. The mentioned compounds have repellent activity confirmed and previously reported by CINTROP^{16 (link)}. The synthetic repellent DEET was used as a positive control (Fig. 1). All chemical reagents used in this work were purchased from Merck ©, USA.Figure 1

Molecules with repellent activity implemented in the electroantennography and proteomic assays (a) Geranyl acetate, (b) Nerolidol, (c) α-bisabolol, (d) DEET.

Portilla Pulido J.S., Urbina Duitama D.L., Velasquez-Martinez M.C., Mendez-Sanchez S.C, & Duque J.E. (2022). Differentiation of action mechanisms between natural and synthetic repellents through neuronal electroantennogram and proteomic in Aedes aegypti (Diptera: Culicidae). Scientific Reports, 12, 20397.

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Effect of Terpenoids on CAPs

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Drugs used were citral, citronellal, citronellol, geraniol, (−)-linalool, (±)-linalool, (+)-borneol, (−)-borneol, geranyl acetate, camphor, rose oxide, myrcene, α-terpineol, ruthenium red (Sigma-Aldrich, St. Louis, MO), bornyl acetate (Funakoshi, Tokyo, Japan), p-cymene, and linalyl acetate (Tokyo Kasei, Tokyo, Japan). All of the drugs except for ruthenium red were first dissolved in dimethyl sulfoxide (DMSO) and then diluted to the final concentration in Ringer solution, where the concentration of DMSO was less than 1%. ruthenium red was dissolved in distilled water at 10 mmol/L and then stored at −25°C. This drug was then diluted to the final concentration in Ringer solution immediately before use. DMSO at 1% did not affect CAPs. The pH of Ringer solution containing drugs was adjusted to 7.0 with 1 mmol/L NaOH. Drugs at concentrations larger than 10 mmol/L were not tested, because a change in osmotic pressure may affect CAPs. Nomenclature of all receptors, drugs, enzymes, and ion channels is according to the Guide to Receptors and Channels (Alexander et al. 2011 (link)).

Ohtsubo S., Fujita T., Matsushita A, & Kumamoto E. (2015). Inhibition of the compound action potentials of frog sciatic nerves by aroma oil compounds having various chemical structures. Pharmacology Research & Perspectives, 3(2), e00127.

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Comprehensive Chemical Compound Synthesis

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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.

Batra S., Corcoran J., Zhang D.D., Pal P., K.P. U., Kulkarni R., Löfstedt C., Sowdhamini R, & Olsson S.B. (2019). A Functional Agonist of Insect Olfactory Receptors: Behavior, Physiology and Structure. Frontiers in Cellular Neuroscience, 13, 134.

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Extraction and Characterization of Essential Oils

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Bornyl acetate (99%), camphene (95%), camphor (96%), carvarol (98%), (−)-carveol (95%), (+)-carvone (96%), β-caryophyllene (98.5%), caryophyllene oxide (95%), β-citronellal (95%), citral (95%), 1,8-cineole (99%), p-cymene (99%), decyl chloroformate (97%), dodecanoic acid (98%), β-farnesene (90%), geranyl acetate (97%), geraniol (98%), isopulegol (98%), linalool (97%), limonene (97%), limonene oxide (97%), methyl linolenate (99%), myrcene (90%), myristic acid (99%), palmitic acid (99%), α-phellandrene (85%), α-pinene (98%), pivalic acid (99%), sabinene (75%), α-terpineol (90%), γ-terpinene (97%), 4-terpineol (95%), terpinolene (90%), and tymol (99%) were obtained from Sigma-Aldrich (St. Louis, MO, USA). Achillea millefolium L. flowers, Citrus aurantium L. fruits, Leptospermum petersonii F. M. Bailey leaves, Ruta graveolens L. leaves, and Thymus vulgaris L. leaves were collected from a local store in Chonju, Korea. Sample specimens were authenticated by Jeongmoon Kim at Chonbuk National University, Korea. Essential oils of the five plants were obtained by steam distillation extraction, and finally dried over Na₂SO₄ to extract the pure essential oils (Table 1).

Park J.H., Jeon Y.J., Lee C.H., Chung N, & Lee H.S. (2017). Insecticidal toxicities of carvacrol and thymol derived from Thymus vulgaris Lin. against Pochazia shantungensis Chou & Lu., newly recorded pest. Scientific Reports, 7, 40902.

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Comprehensive Flavor Compound Reference Protocol

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Reference standards (+) -β-Pinene (≥98.5%), 1-Octen-3-ol, borneol (≥95%), butyric acid (≥99.5%), citral (≥95%), cis-3-hexen-1-ol (≥98%), diacetyl, dimethyl sulphide, dimethyl trisulphide (≥98.5%), 3-methylbutanal (≥97%), 2-methylbutanal (≥95%), ethyl 2-methylbutanoate (99%), ethyl 2-methylpentanoate (internal standard, ≥99%), ethyl-3-methylbutanoate (≥98%), 3-methylbutyl-2-methylpropanoate (≥98%), 2-methylbutyl-2-methylpropanoate (≥95%), and ethyl cinnamate (99%), ethyl 2-methylpropanoate (≥99%), ethyl 3-methylbutanoate (≥98%), ethyl 4-methylpentanoate (≥97%), ethyl butanoate (≥99,5%), ethyl hexanoate (≥99.5%), eugenol (99.6%), furaneol (≥99%), geraniol (≥99%), hexanol (≥99%), 3-methylbutyl acetate (≥97%), linalool (97%), menthol (99%), methyl nonanoate (≥99.8%), myrcene (≥90%), geranyl acetate (≥97%), dimethyl disulphide (≥90%), limonene (97%), hexanal (≥98%), 3-hexenol (≥95%), 2-phenyl ethanol (≥99%), β-caryophyllene (≥80%), α-humulene (≥96%), humulene oxide, S-methyl 5-methylpentanthioate S-methyl hexanthioate, S-methyl 4-methylpentanoate and theaspirane (≥90%) were purchased from Sigma Aldrich (St. Louis, MO, USA).

Machado JC J.r., Lehnhardt F., Martins Z.E., Faria M.A., Kollmannsberger H., Gastl M., Becker T, & Ferreira I.M. (2021). Sensory and Olfactometry Chemometrics as Valuable Tools for Assessing Hops’ Aroma Impact on Dry-Hopped Beers: A Study with Wild Portuguese Genotypes. Foods, 10(6), 1397.

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Insecticidal Toxicity of Lemongrass Oil Constituents

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Geranyl acetate (97.0% purity) and citral (95.0% purity), identified as constituents of the lemongrass essential oil, were obtained from Sigma Aldrich (Darmstadt, Germany). The efficacy of these constituents was determined by their lethal doses (LD₅₀ and LD₉₀) in the laboratory. Six different doses of each constituent were prepared and used to assess the insecticide toxicity and determine relevant toxicological endpoints; a dilution series of doses (8.1, 16.2, 31.2, 62.5, 125, and 250 µg/insect⁻¹) was used to determine dose-mortality relationship and lethal dose. Acetone was used as a control. Each solution (1 μL) was applied to the thorax of third-instar nymphs using a micropipette. Fiften nymphs were tested, placed individually in Petri dishes with one T. molitor pupa per day, and cotton soaked with water. The number of dead nymphs in each Petri dish was counted after 36 h.

Brügger B.P., Martínez L.C., Plata-Rueda A., Castro B.M., Soares M.A., Wilcken C.F., Carvalho A.G., Serrão J.E, & Zanuncio J.C. (2019). Bioactivity of the Cymbopogon citratus (Poaceae) essential oil and its terpenoid constituents on the predatory bug, Podisus nigrispinus (Heteroptera: Pentatomidae). Scientific Reports, 9, 8358.

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Terpenoid Standards Characterization Protocol

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Terpenoid standards used in the study and their purity percentages as obtained from Sigma-Aldrich (UK) were: alloaromadendrene (-) (98%), camphene (95%), camphor (R) (95%), caryophyllene (-) (trans) (98.5%), 1,8-cineole, citral (95%), p-cymene (99%), geraniol (98%), geranyl acetate (97%), ledene (+) (95%), limonene (R) (+) (97%), linalool (±) (95%), linalyl acetate (97%), 6-methyl-5-hepten-2-one (96%), myrcene (90%), α-pinene (-) (99%), β-pinene (-) (99%), sabienene hydrate (97%), α-terpinene (85%), γ-terpinene (97%), terpinolene (95%), terpinen-4-ol (95%), α-terpineol (96%), terpinyl acetate (±) (90%) and verbenol (95%).

Vasireddy L., Bingle L.E, & Davies M.S. (2018). Antimicrobial activity of essential oils against multidrug-resistant clinical isolates of the Burkholderia cepacia complex. PLoS ONE, 13(8), e0201835.

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Polystyrene Rheology in Diverse Solvents

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Polystyrene pellets (Styron
634-71) were purchased from Resinex. As provided by the supplier,
the mass average molar mass, M_w, is 265 000
g·mol^–1, and the dispersity of the molar mass
distribution, Đ, is 2.65. Five solvents were
chosen to study the influence of the solvent type on the rheology
of the polymer solutions. The choice of the solvents was based on
their properties, such as molecular structure, melting and boiling
point, viscosity, and toxicity. These solvents include n-butyl acetate (99% purity, Alfa Aesar), o-xylene
(99% purity, Alfa Aesar), tetrahydrofuran (99% purity, Sigma-Aldrich,
Merck), anisole (99% purity, Sigma-Aldrich, Merck), cyclohexanol (99%
purity, Chem-Lab), and 2-propanol (99.8% purity, Chem-Lab). Two “green”
solvents, (R)-(+)-limonene (93% purity, Sigma-Aldrich,
Merck) and geranyl acetate (90% purity, Sigma-Aldrich, Merck) are
included as well. The solvents were used as-received, without any
purification.

Kol R., Nachtergaele P., De Somer T., D’hooge D.R., Achilias D.S, & De Meester S. (2022). Toward More Universal Prediction of Polymer Solution Viscosity for Solvent-Based Recycling. Industrial & Engineering Chemistry Research, 61(30), 10999-11011.

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Volatile Identification and Enzyme Activity

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The chemicals used for volatile identification and enzyme activity, including hexyl acetate, E-2-hexenyl acetate, Z-3- hexenyl acetate, hexanol, E-2-hexenol, Z-3-hexenol, 2-octanol, butyl acetate, geranyl acetate, ethyl hexanoate, ethyl benzoate, MeJA, MeSA, JA, and SA were purchased from Sigma-Aldrich (USA).

Cao X., Duan W., Wei C., Chen K., Grierson D, & Zhang B. (2019). Genome-Wide Identification and Functional Analysis of Carboxylesterase and Methylesterase Gene Families in Peach (Prunus persica L. Batsch). Frontiers in Plant Science, 10, 1511.

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Odorant-Induced Neuronal Responses

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Odorants were geranyl acetate (95%, Alpha Aesar), ethyl lactate (99%, Alpha Aesar), and citral (95%, Sigma). geranyl acetate and ethyl lactate were diluted into DMSO (Fisher Chemical) for exposing flies prior to RNASeq, qRT-PCR, FISH histology, and electrophysiology. They were used at a 5% concentration, except for the dose–response curve shown in Fig. 1d. For electrophysiological recordings, geranyl acetate and ethyl lactate were diluted 1:10 into paraffin oil (Sigma), and serial dilutions were used to achieve lower concentrations. In Fig. 3a, geranyl acetate was used at 0.1% and citral at 0.1%. In Figs. 3c and 4, geranyl acetate was used at 0.01%.

Baldwin S.R., Mohapatra P., Nagalla M., Sindvani R., Amaya D., Dickson H.A, & Menuz K. (2021). Identification and characterization of CYPs induced in the Drosophila antenna by exposure to a plant odorant. Scientific Reports, 11, 20530.

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