2 3 butanedione

Manufactured by Merck Group

Sourced in United States, Germany, Poland

2,3-butanedione is a chemical compound used as a laboratory reagent. It is a colorless liquid with a characteristic buttery odor. 2,3-butanedione is commonly used as a standard in analytical chemistry and as a flavoring agent in various industries.

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Close spelling variants of this product

2,3-butanedione monoxime (42 citations) BDM (2,3-butanedione monoxime) (15 citations) 2,3-butanedione monoxamine (10 citations) 2,3-butanedione 2-monoxime (BDM) (3 citations) 2,3-butanedione 2-monoxime (3 citations) Citrulline (C7629), 2,3-Butanedione monoxime (B0753), (2 citations) Diacetyl (DA; 2,3-butanedione) (2 citations) Diacetyl (2,3-butanedione),Cu(Cl)2·2H2O (2 citations)

25 protocols using 2 3 butanedione

Ion-Molecule Reactions of VOCs

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A wide scope of chemical
classes of VOCs
were included in order to ascertain the differences in ion–molecule
reactions between the literature data and the present data obtained
from the two instruments. We therefore used 1-propanol (PENTA, 99.5%),
2-propanol (PENTA, 99.8%), 2,3-butanedione (Aldrich, 97%), acetaldehyde
(Sigma-Aldrich, ≥99.5%), acetic acid (Sigma-Aldrich, ≥99.7%),
acetone (PENTA, 99.5%), ethyl acetate (Sigma-Aldrich, 99.8%), ethanol
(Lachner, 96%), and R-limonene (Sigma-Aldrich, Analytical
Standard).

Swift S.J., Španěl P., Sixtová N, & Demarais N. (2023). How to Use Ion-Molecule Reaction Data Previously Obtained in Helium at 300 K in the New Generation of Selected Ion Flow Tube Mass Spectrometry Instruments Operating in Nitrogen at 393 K. Analytical Chemistry, 95(29), 11157-11163.

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Comprehensive Coffee Compound Analysis

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The following chemicals were obtained from Sigma-Aldrich (Munich, Germany): standard caffeine (CAS: 58-08-2), trigonelline (CAS: 6138-41-6), sucrose (CAS: 57-50-1), 5-caffeoylquinic acid (5-CQA) (CAS: 906-33-2) used to represent chlorogenic acid, reference volatile compounds including; 2-furfurylthiol (CAS 98-02-2), hexanal (CAS: 66-25-1), 2-methylfuran (CAS 534-22-5), 2-butanone (CAS: 78-93-3), 2-methyl pyrazine (CAS: 109-08-0), 2,3-dimethyl pyrazine (CAS: 5910-89-4), 2-ethyl-3,5-dimethylpyrazine (CAS:13925-07-0), 2-ethyl-6-methylpyrazine (CAS: 13925-03-6), 2-ethyl-3-methylpyrazine (CAS: 15707-23-0), pyridine (CAS: 110-86-1), 2,3-butanediol (CAS: 513-85-9), benzaldehyde (CAS: 100-52-7), 4-nonanol (CAS: 5932-79-6), phenol (CAS: 108-95-2), 2,3-butanedione (CAS: 207-069-8); HPLC grade water, hexane and basic lead acetate (CAS: 301-04-2).

Ogutu C., Cherono S., Ntini C., Wang L, & Han Y. (2022). Comprehensive analysis of quality characteristics in main commercial coffee varieties and wild Arabica in Kenya. Food Chemistry: X, 14, 100294.

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Synthesis and Characterization of Organic Compounds

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Reagents of analytical grade were used as received from their commercial sources. Benzyl chloride was obtained from ACROS Organics (Morris Plains, NJ, USA), potassium hydroxide from Riendemann Schmidt (Kajang, Malaysia), carbon disulfide from Fisher Scientific (Chino, CA, USA) and copper (II) acetate from R&M Chemicals (Essex, UK). Hydrazine hydrate, iodomethane, glyoxal, 2,3-hexanedione, 2,3-heptanedione, 2,3-pentanedione, 2,3-butanedione and copper (II) chloride were obtained from Merck (Darmstadt, Germany). Absolute ethanol, 95% ethanol, dimethyl sulfoxide, acetone and dimethylformamide were obtained from RCI Labscan (Bangkok, Thailand). Elemental analysis was conducted via a Vario MACRO CUBE CHNS analyser (Germany), while IR spectra were recorded using a PerkinElmer FTIR spectrophotometer (Waltham, MA, USA). Melting points were measured using an Electrothermal IA9100 melting point apparatus (Essex, UK).
¹H NMR spectra were obtained via a Bruker FT-NMR 300 MHz (Germany). TLC was performed via 60F aluminium silica gel aluminium plates with a 254 nm fluorescent indicator from Merck (Darmstadt, Germany). UV-Vis spectroscopy was performed via a Biochrom UltroSpec 8000 spectrophotometer (Cambridge, UK).

Break M.K., Fung T.Y., Koh M.Z., Ho W.Y., Tahir M.I., Elfar O.A., Syed R.U., Khojali W.M., Alluhaibi T.M., Huwaimel B., Wiart C, & Khoo T.J. (2023). Synthesis, Crystal Structure, Antibacterial and In Vitro Anticancer Activity of Novel Macroacyclic Schiff Bases and Their Cu (II) Complexes Derived from S-Methyl and S-Benzyl Dithiocarbazate. Molecules, 28(13), 5009.

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Analytical Reagents for Organic Synthesis

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Petroleum ether (40-60°C; 95%) was purchased from Acros Organics (Geel, Belgium). 2,3-Hexanedione (94%) and 2,4,5-trimethyl oxazole (97%) were obtained from Alfa Aesar (Karlsruhe, Germany).
Benzaldehyde (99%) and hydrogen peroxide (30%) were obtained from AppliChem (Darmstadt, Germany). Acetic acid (100%), chloroform-d (99.8 atom% D, with 0.03 vol% TMS, stabilized with Ag), diethyl ether (99.5%), iron(II) sulphate heptahydrate (99.5%), sodium carbonate decahydrate (98%), sodium sulphate (p.a.) and sulfuric acid (96%) were purchased from Carl Roth (Karlsruhe, Germany). Pentanal (97%) was obtained from Fisher Scientific (Darmstadt, Germany), Silica gel 60 was purchased from Macherey-Nagel (Düren, Germany) and 2,3-butanedione (97%) from Merck (Darmstadt, Germany). Acetoin (96%), 2,3-pentanedione (97%), 2,3,5,6-tetramethylpyrazine (98%) and 2,3,5-trimethylpyrazine (99%) were purchased from Sigma-Aldrich (Taufkirchen, Germany). 5-Ethyl-2,3-dimethylpyrazine (98%) was obtained from TCI (Eschborn, Germany). Butanal (97%) and propanal (97%) were purchased from Th. Geyer (Renningen, Germany) and ethyl acetate (98%) from VWR (Darmstadt, Germany). Helium (5.0) was obtained from Praxair (Düsseldorf, Germany) and nitrogen (5.0) from Air Liquide (Düsseldorf, Germany). All numbers given in parentheses represent the minimum purity.

Birk F., Brescia F.F., Fraatz M.A., Pelzer R., & Zorn H. (2021). Aroma active alkylated pyrazines are produced by Basfia succiniciproducens as by‐products of succinic acid production. Flavour and Fragrance Journal, 36(5), 605-612.

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Fatty Acid and Volatile Analysis

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Fatty acid methyl esters of palmitic acid (C16:0), palmit oleic acid (C16:1), stearic acid (C18:0), oleic acid (C18:1), linoleic acid (C18:2) and linolenic acid (C18:3), C₃-C₂₅ of n-alkanes, 2,3-butanedione, hexanal, (E)-2-hexenal, 1-octen-3-ol, 1-octen-3-one, 2-heptanone, (E)-2-octenal, and 1-hexanol were purchased from Sigma (St. Louis, MO, USA). 3-Octen-2-one, 2-n-butyl furan, heptanal, and (E)-2-nonenal were purchased from TCI (Tokyo, Japan). Benzeneacetaldehyde, 2,3-butanediol, 3-methyl-2-butanone, and benzaldehyde were obtained from RHAWN reagent corporation (Shanghai, China). 1-Penten-3-one and 3-methyl-1-butanol were purchased from Aladdin reagent corporation (Shanghai, China). 2-Pentyl-furan was purchased from J&K Scientific Ltd. (Beijing, China). Heptenal was purchased from Accustandard (New Haven, CT, USA). Diethyl ether, n-hexane, and petroleum ether were purchased from Yongda chemical reagent co. Ltd. (Tianjin, China). Boron trifluoride-methanol solution (14% BF3·methanol) was purchased from CNW technologies (Dusseldorf, Germany). Milli-Q water was used in this study (Millipore, Billerica, MA, USA).

Li P., Zhu Y., Li S., Zhang A., Zhao W., Zhang J., Chen Q., Ren S., Liu J, & Wang H. (2020). Variation Patterns of the Volatiles during Germination of the Foxtail Millet (Setaria Italic): The Relationship between the Volatiles and Fatty Acids in Model Experiments. Molecules, 25(5), 1238.

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Flavor Compound Procurement for Analysis

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Diethyl ether, dansyl chloride, and saturated
alkane standards were purchased from Sigma-Aldrich (Gillingham, Dorset,
UK). O-(2,3,4,5,6-Pentafluorobenzyl)-hydroxylamine
hydrochloride (PFBHA) was purchased from Fluka (Loughborough, UK).
The following food-grade aroma compounds were purchased from Sigma-Aldrich
(purity in parenthesis): acetaldehyde (≥99%), acetic acid (≥99.5%),
2,3-butanedione (97%), butanoic acid (≥99%), (E)-β-damascenone (≥98%), dimethyl sulfide (≥99%),
5-ethyl-3-hydroxy-4-methyl-2(5H)-furanone (97%),
5(or 2)-ethyl-4-hydroxy-2(or 5)-methyl-3(2H)-furanone
(96%), (Z)-4-heptenal (≥98%), 3-hydroxy-4,5-dimethyl-2(5H)-furanone (10% in propylene glycol), 4-hydroxy-2,5-dimethyl-3(2H)-furanone (≥98%), methional (≥97%), 2-methoxy-4-methylphenol
(≥98%), 2-methoxyphenol (≥99%), 2-methoxy-4-vinylphenol
(≥98%), 2-methylbutanal (≥95%), 3-methylbutanal (≥97%),
3-methylbutanoic acid (99%), 3-methyl-1-butanol (≥98%), methylpropanal
(≥98%), 2,3-pentanedione (≥96%), phenylacetaldehyde
(10% in ethanol), 2-phenylacetic acid (≥99%), 2-phenylethanol
(≥99%), vanillin (≥97%), and 4-vinylphenol (10% in propylene
glycol). Encapsulated 3-methyl-2-butene-1-thiol flavor standard (0.02–4
ng/g) was purchased from FlavorActiV (Aston Rowant, UK).

Piornos J.A., Balagiannis D.P., Methven L., Koussissi E., Brouwer E, & Parker J.K. (2020). Elucidating the Odor-Active Aroma Compounds in Alcohol-Free Beer and Their Contribution to the Worty Flavor. Journal of Agricultural and Food Chemistry, 68(37), 10088-10096.

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Titanium Butoxide-Based Organic Synthesis

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During the synthesis, 2.7 mL titanium (IV) butoxide (97%, Sigma Aldrich, MO, USA), 0.57 mL ethyl acetoacetate (99%, Sigma Aldrich), 57 μL 2,4-pentanedione (99%, Sigma Aldrich, MO, USA) and 57 μL 2,3-butanedione (97%, Sigma Aldrich, MO, USA) were mixed and stirred at room temperature overnight [37 (link)].

Duong B., Lohawet K., Muangnapoh T., Nakajima H., Chanlek N., Sharma A., Lewis D.A, & Kumnorkaew P. (2019). Low-Temperature Processed TiOx/Zn1−xCdxS Nanocomposite for Efficient MAPbIxCl1−x Perovskite and PCDTBT:PC70BM Polymer Solar Cells. Polymers, 11(6), 980.

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DNPH-based Carbonyl Compound Analysis

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2,4-Dinitrophenylhydrazine (DNPH) was purchased from Tokyo Chemical Industry (TCI, Portland, OR); d₃-labeled DNPH (>98% isotopic purity) and malondialdehyde (MDA) was obtained from Santa Cruz Biotechnology (Dallas, TX); Ketones Mix (Propanone, 2-Butanone, 4-Methyl-2-Pentanone, 2-Hexanone, Cyclohexanone) and TO11/IP-6A Aldehyde/Ketone-DNPH Mix (Acetaldehyde-DNPH, Propanone-DNPH, Propanal-DNPH, Acrolein-DNPH, Benzaldehyde-DNPH, Butanal-DNPH, Crotonaldehyde-DNPH, 2,5-Dimethylbenzaldehyde-DNPH, Formaldehyde-DNPH, Hexanal-DNPH, Pentanal-DNPH, Isopentanal-DNPH, o-Tolualdehyde-DNPH, m-Tolualdehyde-DNPH, p-Tolualdehyde-DNPH), 4-hydroxy-3-methoxybenzaldehyde (Vanillin), Indole-3-carboxaldehyde, Hexanophenone, Heptanophenone, 2,3-Butanedione, 2,3-Pentanedione, trans-2-methyl-2-butenal, 3-methyl-2-butenal (methylcrotonaldehyde), sodium acetate, and concentrated HCl were obtained from Sigma Aldrich (Milwaukee, WI); ¹³C₂-Acetaldehyde was obtained from Cambridge Isotope Laboratories (Tewksbury, MA); Methylglyoxal (MG) was obtained from Thermo Fisher (Morris Plains, NJ); Strata-X polymeric reverse-phase cartridge was purchased from Phenomenex (Torrance, CA). All acids and organic solvents were HPLC grade or better.

Dator R., Carra’ A., Maertens L., Guidolin V., Villalta P.W, & Balbo S. (2016). A High Resolution/Accurate Mass (HRAM) Data-Dependent MS3 Neutral Loss Screening, Classification, and Relative Quantitation Methodology for Carbonyl Compounds in Saliva. Journal of the American Society for Mass Spectrometry, 28(4), 608-618.

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Characterization of Dicarbonyl Compounds

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2,3-Butanedione (CAS#431-03-8) and 2,3-hexanedione (CAS# 3848-24-6) were purchased as single lots from Sigma-Aldrich (St. Louis, MO). The purity of BD was 99.3%, and the purity of HD was 95.9%. 2,3-Pentanedione (CAS# 600-14-6) was purchased from Acros Organics (Morris Plains, NJ) at a purity of 96.5%.

Morgan D.L., Jokinen M.P., Johnson C.L., Price H.C., Gwinn W.M., Bousquet R.W, & Flake G.P. (2016). Chemical Reactivity and Respiratory Toxicity of the α-Diketone Flavoring Agents: 2,3-Butanedione, 2,3-Pentanedione and 2,3-Hexanedione. Toxicologic pathology, 44(5), 763-783.

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Flavor Compound Isolation and Synthesis

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The following compounds, 2-methylpropanal, 2,3-butanedione, 3-methylbutanal, methional, 2-acetylfuran, 1-octen-3-one, 1-octen-3-ol, (E)-2-nonenal, (E,Z)-2,6-nonadienal, 2-acetylpyrazine, 2-acetyl-2-thiazoline, 2-ethyl-3,5(and 6)-dimethylpyrazine, (E,E)-2,4-decadienal, 1-hexanol, 2-phenylethanol, salicylaldehyde, p-vinyl guaiacol, ethyl nonanoate, and ethyl octanoate were purchased from Sigma Aldrich (St. Louis, MO, USA). 2-Ethyl-3,5-dimethylpyrazine and 2-ethyl-3,6-dimethylpyrazine were separated using preparative GC and [²H₃]-2-Acetyl-1-pyrroline and [²H₄]-2-acetyl-2-thiazoline were synthesized as previously described [37 (link)]. 3-Methyl-1-butanol, guaiacol, and 2-methyl-3-heptanone were purchased from Tokyo Chemical Industry (TCI; Portland, OR, USA). 2,3-Diethyl-5-methylpyrazine, butylated hydroxytoluene (BHT), ethanol (200 proof) and dichloromethane were purchased from Fisher Scientific (Pittsburgh, PA, USA). Sodium bicarbonate and anhydrous sodium sulfate were purchased from Avantor (Center Valley, PA, USA).

Paravisini L., Sneddon K.A, & Peterson D.G. (2019). Comparison of the Aroma Profiles of Intermediate Wheatgrass and Wheat Bread Crusts. Molecules, 24(13), 2484.

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