2 hexanone

Manufactured by Merck Group

Sourced in Germany, United States

2-hexanone is a colorless, flammable liquid chemical compound. It has the chemical formula CH3(CH2)3CH2C(O)CH3. 2-hexanone is used as a solvent and in the production of other chemicals.

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Standard 2‐hexanone (2 citations)

14 protocols using 2 hexanone

Development and Validation of TD-GC-qMS Method

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The TD-GC-qMS method development was done using dimethyl sulphide (1, anhydrous, ≥ 99%), 2-methylbutanal (2, 95%), dimethyl disulphide (3, ≥ 98%), 2-hexanone (4, analytical standard), 1-octanol (6, anhydrous, ≥ 99%), 2-nonanone (7, ≥ 99%), 1-undecene (8, 97%), 1-decanol (9, ≥ 9 8%) and 2-aminoacetophenone (10, analytical standard) purchased from Sigma-Aldrich (Taufkirchen, Germany), and 2-heptanone (5, ≥ 98%) purchased from Merck KGaA (Darmstadt, Germany).
To verify the analysis of cyclic siloxanes by atmospheric pressure ionization (APPI), coupled with thermogravimetry (TG) and a qMS, three cyclic siloxanes were analysed as single standards. Octamethylcyclotetrasiloxane (D4, 98%, Alfa Aesar, Karlsruhe, Germany), decamethylcyclopentasiloxane (D5, 97%, Alfa Aesar, Karlsruhe, Germany) and dodecamethylcyclohexasiloxane (D6, 95%, Alfa Aesar, Karlsruhe, Germany) were used.
For all purposes, liquid chromatography-mass spectrometry (LC-MS) grade methanol from VWR (Leuven, Belgium) and ultrapure water, generated with a water purification system from Sartorius Stedim (Göttingen, Germany), were used. For cleaning purpose, Decon 90 from VWR (Leuven, Belgium) was used.

Koehler T., Ackermann I., Brecht D., Uteschil F., Wingender J., Telgheder U, & Schmitz O.J. (2020). Analysis of volatile metabolites from in vitro biofilms of Pseudomonas aeruginosa with thin-film microextraction by thermal desorption gas chromatography-mass spectrometry. Analytical and Bioanalytical Chemistry, 412(12), 2881-2892.

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Comprehensive Ketone Characterization Protocol

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The following liquid substances were purchased from Sigma-Aldrich: 2-pentanone (98%), 3-pentanone (99%), 2-hexanone (98%), 3-hexanone (98%), 3-heptanone (analytical standard), 4-heptanone (98%), 2-nonanone (99%), 3-nonanone (99%), 2-decanone (98%), cyclohexanone (99.8%), 3-methyl-2-pentanone (99%), 2-methyl-3-pentanone (97%), 2-methyl-3-hexanone (98%), and 2-methyl-3-heptanone (99%). 2-butanone (99.5%), 2-heptanone (98.5%), and 3-methyl-2-butanone (98.5%) were purchased from Honeywell. 3-octanone (99%) and 3-decanone (97%) were purchased from Acros Organics and SAFC, respectively. These were used with no further purification.

Malásková M., Olivenza-León D., Piel F., Mochalski P., Sulzer P., Jürschik S., Mayhew C.A, & Märk T.D. (2019). Compendium of the Reactions of H3O+ With Selected Ketones of Relevance to Breath Analysis Using Proton Transfer Reaction Mass Spectrometry. Frontiers in Chemistry, 7, 401.

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Analytical Standards for Aroma Profiling

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The standards 2-hexanone, benzeneacetaldehyde, linalool, linalool oxides, phenylethyl alcohol, 4-oxoisophorone, menthol, α-terpineol, safranal, geraniol, indole, and 2-ethyl-3-methylpyrazine were purchased from Sigma-Aldrich Co., Ltd. (St. Louis, MO, USA). The standards, 1-ethylpyrrole, benzyl alcohol, 1,2-dimethoxybenzene, 3,4-dimethoxytoluene, 1,2,3-trimethoxybenzene, 1,2,4-trimethoxybenzene, trans-β-ionone, 2,4-ditert- butylphenol, and dihydroactinidiolide were obtained from Alfa Aesar Co., Ltd. (Heysham, Lancashire, UK). A standard series of C₈–C₂₀ alkanes were used for retention index (RI) determination, and the internal standard cyclohexanone were purchased from Sigma-Aldrich Co., Ltd. (St. Louis, Mo, USA). Other reagents were all of analytical grade and obtained from Sinopharm Chemical Reagent Co., Ltd. (Shanghai, China).

Zhang T., Ni H., Qiu X.J., Li T., Zhang L.Z., Li L.J., Jiang Z.D., Li Q.B., Chen F, & Zheng F.P. (2019). Suppressive Interaction Approach for Masking Stale Note of Instant Ripened Pu-Erh Tea Products. Molecules, 24(24), 4473.

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Odorant Delivery for Stable Glomerular Activation

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Odors [2-hexanone, 2-heptanone, and ethyl butyrate (Sigma-Aldrich)] were delivered using a flow-dilution olfactometer previously described (Fletcher et al., 2009 (link)). Separate flow controllers for the clean air and the pure odorant vapor were used to mix the flow streams at the end of the odor delivery system to achieve an approximate concentration of 0.25, 0.5, or 0.75% saturated vapor (s.v.) at a flow rate of 0.7 L/min. The odor concentration used for each animal was a concentration that activated discrete, stable glomeruli.

Ogg M.C., Bendahamane M, & Fletcher M.L. (2015). Habituation of glomerular responses in the olfactory bulb following prolonged odor stimulation reflects reduced peripheral input. Frontiers in Molecular Neuroscience, 8, 53.

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Volatile Organic Compound Identification

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Identities of all VOCs considered as potential marker substances were confirmed through analysis of pure reference substances.
Acetone, 2-butanone, hexanal, nonanal, isoprene and benzene were acquired from Ionimed Analytik GmbH (Innsbruck, Austria). Butane, pentane and hexane were bought from Supelco (Bellefonte, USA). Methyl-isobutyl-ketone, 1-propanol, styrene, 3-octanone, 2-heptanone, furan, heptane, methylacetate, 2-methylfuran, 2-ethylfuran, 2-pentylfuran, 2-pentanone, 2-hexanone, 3-hexanone, 3-methyl-2-butanone, 3-methyl-2-pentanone, 2-propanethiol and dimethylsulfide were purchased from Fluka/Sigma-Aldrich (Steinheim, Germany). 2-Methyl-butanal and dimethyldisulfide were bought from Abbott GmbH & Co.KG (Wiesbaden, Germany). Ethylbenzene was acquired from Merck (Darmstadt, Germany). 3-methylfuran and 3-methylbutanal was purchased from TCI Europe N.V. (Zwijndrecht, Belgium).

Bergmann A., Trefz P., Fischer S., Klepik K., Walter G., Steffens M., Ziller M., Schubert J.K., Reinhold P., Köhler H, & Miekisch W. (2015). In Vivo Volatile Organic Compound Signatures of Mycobacterium avium subsp. paratuberculosis. PLoS ONE, 10(4), e0123980.

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Solvent Preparation for Analytical Tests

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Toluene (≥99.5%) was provided by VWR chemicals (Fontenay-sous-Bois, France). M ethanol, ethanol, acetone, 2-butanone, 2-pentanone, 2-hexanone, and 1,4-dioxane HPLC grade (≥98%) were ordered from Sigma-Aldrich (St. Louis, MO, USA). Non-woven gauzes (7.5 cm × 7.5 cm) were purchased from ABSO, laboratory Marque Verte (Villers-lès-Nancy, France).

Abar T., Mestdagh H., Heninger M, & Lemaire J. (2024). Analysis of VOCs in Liquids through Vaporization in a Tubular Oven Monitored by Chemical Ionization Mass Spectrometry. Sensors (Basel, Switzerland), 24(4), 1048.

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Preparation of Volatile Organic Compound Standards

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Individual samples were prepared by injecting desired liquid volumes of 2-butanone, 2-hexanone, ethyl acetate and 4-methyl-2-pentanone (Sigma Aldrich, St Louis, MO) into each sample bag (SKC Tedlar^® Sample bag, SKC Inc., Eighty Four, PA) filled with 3 L of ultra high purity nitrogen (Airgas, Radnor, PA). These bags were maintained for more than 10 min at room temperature to equilibrate analytes into the gas phase to achieve the stock concentrations (1000 ppm). Serial dilution was performed from the stock concentration to achieve 100 ppm concentration of each chemical. Each gas phase chemical was sampled into a gas tight 1 mL glass syringe (Hamilton Co., Reno, NV) from the final concentration (100 ppm) and introduced separately into the inlet of the differential mobility spectrometer using a syringe pump with a dilution nitrogen gas flow. The final concentration of each chemical at the DMS cell inlet was 500 ppb. The bags with chemical mixtures were prepared by adding each new chemical to the bag followed by serial dilution. Therefore, the final concentration of each chemical in a mixture was ~ 500 ppb.

Yeap D., Hichwa P.T., Rajapakse M.Y., Peirano D.J., McCartney M.M., Kenyon N.J, & Davis C.E. (2019). Machine vision methods, natural language processing and machine learning algorithms for automated dispersion plot analysis and chemical identification from complex mixtures. Analytical chemistry, 91(16), 10509-10517.

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Enzymatic Synthesis of Organic Compounds

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Formaldehyde (37% aqueous solution), acetaldehyde
(≥99.5%), propionaldehyde (≥98.0%), benzaldehyde (≥99.5%),
butyraldehyde (≥99.5%), isobutyraldehyde (≥99.0%), valeraldehyde
(≥97.0%), isovaleraldehyde (≥97.0%), pyruvaldehyde (40%
aqueous solution), dl-lactaldehyde (≥95.0%), 2-hexanone
(≥99.5%), acetophenone (≥99.5%), butanone (≥99.9%),
2-pentanone (≥99.5%), 2-deoxy-d-ribose (≥97.0%),
2-deoxyribose-5-phosphate (≥95.0%), 2,4-dinitrophenylhydrazine
(97.0%), o-(2,3,4,5,6-pentafluorobenzyl)-hydroxylamine
(≥99.0% hydrochloride salt), and 2-(dimethylamino)ethylhydrazine
(≥97.0% dihydrochloride salt) were purchased from Sigma-Aldrich
(St. Louis, MO). 4-Hydrazinobenzoic acid (98.0%) and 4-methoxyphenylhydrazine
(98.0%, hydrochloride salt) were purchased from Acros Organics (New
Jersey). Acetone (100%) was purchased from VMR (Fontenay-sous-Bois,
France); 3-pentanone (≥99.0%) was from Merck (Darmstadt, Germany).
The recombinant DERA enzyme was expressed in E. coli as described below in more details. All solvents (HPLC grade) were
obtained from Sigma-Aldrich and used without further purification.
The DERA substrates were prepared in 50 mM ammonium acetate (pH 7.1),
while carbonyl compounds were in methanol and hydrazines samples were
prepared in water (HPLC grade) solution.

Thangaraj S.K., Voutilainen S., Andberg M., Koivula A., Jänis J, & Rouvinen J. (2019). Bioconjugation with Aminoalkylhydrazine for Efficient Mass Spectrometry-Based Detection of Small Carbonyl Compounds. ACS Omega, 4(8), 13447-13453.

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Olfactory Stimulus Set for Neuroscience

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The odor stimulus set consisted of 2-hexanone (Sigma, 02473), octanal (Aldrich, O5608), isoamyl acetate (Tokyo Chemical Industries, A0033), ethyl butyrate (Aldrich, E15701), valeraldehyde (Aldrich, 110132), ethyl tiglate (Alfa Aesar, A12029), acetophenone (Fluka, 00790), γ-terpinene (Aldrich, 223190), ethyl acetate (Sigma-Aldrich, 34858), and methyl tiglate (Alfa Aesar, A11964).

Nagappan S, & Franks K.M. (2021). Parallel processing by distinct classes of principal neurons in the olfactory cortex. eLife, 10, e73668.

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Analytical Reagents for Spectroscopy

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Acetonitrile (99.9%), dichloromethane
(99.8%), 1-bromodecane (98%), ethyl acetate (99.5%), 1-methylimidazole
(99%), nonane (99%), 2-hexanone (99%), methyl tiglate (99%), n-hexane (99.7%), 1-hexene (99.8%), cis-1,4-hexadiene (99%), 2.3-dimethyl-1,3-butadiene (98%), 2-hexyne
(99%), benzene (99.8%), toluene (99.5%), o-xylene
(99.8%), m-xylene (99%), p-xylene
(99%), ethylbenzene (99.8%), 1-nonene (96%), and [Ag⁺][NTf₂^–] (97%) were purchased from Sigma-Aldrich
(St. Louis, MO, USA). Compounds 3-hexyne (99%) and cis-2-hexene (96%) were purchased from Alfa Aesar (Tewksbury, MA, USA).
Lithium bis[(trifluoromethyl)sulfonyl]imide ([Li⁺][NTf₂^–], 99.5%) salt was purchased from SynQuest
Laboratories (Alachua, FL, USA). Untreated fused silica capillary
tubing (I.D. 250 μm) and naphthalene (98%) were purchased from
Supelco (Bellefonte, PA, USA). Cylinders containing custom gas mixtures
(ultra-high purity, 99.999%) of hydrogen/nitrogen, hydrogen/helium,
and hydrogen/methane/nitrogen were purchased from Airgas, Inc. (Des
Moines, IA, USA). All chemicals were used as received without further
purification.

Eor P., Tryon-Tasson N., Kong S., Smith E.A, & Anderson J.L. (2022). Deconvoluting the Combined Effects of Gas Composition and Temperature on Olefin Selectivity for Separations Using Silver(I) Ions in Ionic Liquids. ACS Measurement Science Au, 3(1), 53-61.

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