Phenoxyacetic acid

Manufactured by Merck Group

Sourced in United States

Phenoxyacetic acid is a chemical compound used in various laboratory applications. It is a colorless, crystalline solid with a distinctive odor. Phenoxyacetic acid serves as a precursor for the synthesis of other chemical compounds and is utilized in various research and development processes.

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2-methyl-4-chloro-phenoxyacetic acid (2 citations)

4 protocols using phenoxyacetic acid

Quantification of Phenoxy Acid Herbicides

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Pestanal standards (purity greater than 99%) of the phenoxy acid herbicides 2-(4-chloro-2-methylphenoxy) propanoic acid (mecoprop), 2,4-dichlorophenoxyacetic acid (2,4-D), (4-chloro-2-methylphenoxy)acetic acid (MCPA), (2,4,5-trichlorophenoxy) acetic acid (2,4,5-T), 2-(2,4,5-trichlorophenoxy)propanoic acid (2,4,5-TP), 2,6-dichloro-pyridine-2-carboxylic acid (clopyralid), 2-(2,4-dichlorophenoxy)propanoic acid (dichloroprop) and [(3,5,6-trichloro-2-pyridinyl)oxy]acetic acid (triclopyr) were obtained from Labor Dr. Ehrenstorfer-Schäfers (Augsburg, Germany). Chemical standards of phenoxyacetic acid, benzoic acid and phenylacetic acid derivatives with purity greater than 95% were purchased from Sigma–Aldrich (St. Louis, MO, USA). Stock solutions (1.00 g L⁻¹) of individual analytes were prepared by dissolving accurately weighed 10 mg of each solute in 10 mL of HPLC-grade acetonitrile (Carlo Erba Reagenti, Milano, Italy) and stored at 4 °C. HPLC-grade acetonitrile was acquired from Sigma-Aldrich (St. Louis, MO, USA). Double deionized water was obtained from a Milli-Q filtration/purification system (Millipore, Bedford, MA, USA).

Biancolillo A., Maggi M.A., Bassi S., Marini F, & D’Archivio A.A. (2020). Retention Modelling of Phenoxy Acid Herbicides in Reversed-Phase HPLC under Gradient Elution. Molecules, 25(6), 1262.

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Synthesis of Functionalized Alcohols

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Acryloyl chloride, bis(cyclopentadienyl)titanium dichloride, 9-borabicyclo[3.3.1]nonane, 3-buten-3-ol, n-butyl acrylate, n-decan-1-ol, Dess-Martin periodinane, diethyl ether, diethylaluminium chloride, n-heptan-1-ol, 6-hepten-1-ol, 1,4-hexadiene, (E)-2-hexen-1-ol, (E)-3-hexen-1-ol, (E)-4-hexen-1-ol, 5-hexen-1-ol, 1-hexen-3-ol, 5-hexyn-1-ol, hydrogen peroxide solution, lithium diisopropylamide, magnesium sulfate, n-octan-1-ol, 1-octen-3-one, n-pentan-1-ol, 4-penten-1-ol, petroleum ether, phenoxyacetic acid, propionic acid, sodium bicarbonate, sodium thiosulfate pentahydrate, tetrahydrofuran, triethyl orthoacetate, trimethylamine, and vinylmagnesium bromide solution were purchased from Sigma-Aldrich (Steinheim, Germany). The educts 1-hepten-3-ol, 1-hexen-3-one, and 7-octen-1-ol were purchased from abcr (Karlsruhe, Germany) and chloroform, sodium hydroxide, and sulphuric acid from Carl Roth (Karlsruhe, Germany). Dichloromethane, ethyl acetate, n-hexyl acrylate, methanol, 1-nonen-3-one, n-propyl acrylate, silica gel (Normasil 60, 40–63 µm), and sodium chloride were purchased from VWR International GmbH (Darmstadt, Germany). All reactants were at least of reagent grade.

Bauer P., Ortner E, & Buettner A. (2022). Influence of elongation and desaturation on chemosensory properties in acrylates and their corresponding 1-alken-3-ones. Analytical and Bioanalytical Chemistry, 414(28), 8009-8022.

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Extraction and Analysis of Fungal Metabolites

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All standard chemicals (toluhydroquinone, orcinol, epoxysuccinic acid, phenoxyacetic acid, 2,5-dihydroxybenzoic acid (gentisic acid), fusaric acid, 3-(3,4-dihydroxyphenyl)-2-propenoic acid (caffeic acid), propyl-3,4,5-trihydroxybenzoate, jasmonic acid, sterigmatocystin, penicillin G, physcion and riboflavin) and chromatographic solvents were of highest analytical grade and purchased from either Sigma Aldrich or Fisher Scientific, except ethyl acetate (Acros Organics), orsellinic acid (Alfa Aesar) and chrysophanol (Acros Organics). Water was obtained from a Milli-Q system (Millipore). Cholinium chloride (>98 %, Sigma Aldrich), hereafter referred to solely as choline, and 1-ethyl-3-methylimidazolium chloride ([C₂mim]Cl, >98 %, Iolitec) were dried in vacuo (40–70 °C, 24–48 h, ca. 0.01 mbar) prior to use. Monodictyphenone was kindly provided by Prof. Thomas J. Simpson (University of Bristol, UK) [33 (link)].

Alves P.C., Hartmann D.O., Núñez O., Martins I., Gomes T.L., Garcia H., Galceran M.T., Hampson R., Becker J.D, & Silva Pereira C. (2016). Transcriptomic and metabolomic profiling of ionic liquid stimuli unveils enhanced secondary metabolism in Aspergillus nidulans. BMC Genomics, 17, 284.

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Analytical Methods for Microbial Signaling Molecules

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Cell culture media were purchased from Becton-Dickinson (Franklin Lakes, NJ, USA); chemical reagents such as methanol, acetic acid and potassium phosphate from Fisher Scientific (Waltham, MA, USA); N-acyl-l-homoserine lactones (except N-(3-oxohexanoyl)-l-homoserine lactone, which was from Santa Cruz Biotechnology, Dallas, TX, USA), l-homoserine lactone hydrochloride (HSL), penicillin V, phenoxyacetic acid (POA), methyl phenoxyacetate (MPOA), methyl hexanoate, methyl decanoate, p-dimethylaminobenzaldehyde (PDAB), o-phthalaldehyde (OPA), kanamycin, and DMSO from Sigma-Aldrich (Burlington, MA, USA); methyl octanoate and methyl dodecanoate from Fluka (Burlington, MA, USA); methyl butyrate from Acros Organics (Waltham, MA, USA); methyl butyrylacetate from Alfa Aesar (Tewksbury, MA, USA); and methyl 3-oxodecanoate and methyl 3-oxododecanoate from Toronto Research Chemicals (Toronto, ON, Canada). 6-aminopenicillanic acid (6-APA) and natural aliphatic penicillins (penicillin K, penicillin F and penicillin dihydro-F) were provided by Antibióticos S.A. (León, Spain). All reagents used showed a purity level of at least ≥95%. Oligonucleotides were synthesized by Sigma-Aldrich (Burlington, MA, USA).

Serrano-Aguirre L., Velasco-Bucheli R., García-Álvarez B., Saborido A., Arroyo M, & de la Mata I. (2021). Novel Bifunctional Acylase from Actinoplanes utahensis: A Versatile Enzyme to Synthesize Antimicrobial Compounds and Use in Quorum Quenching Processes. Antibiotics, 10(8), 922.

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