10 undecenoic acid

Manufactured by Merck Group

Sourced in United States

10-undecenoic acid is a straight-chain, unsaturated carboxylic acid with the chemical formula CH2=CH(CH2)8COOH. It is a colorless, viscous liquid that is commonly used as a chemical intermediate in the production of various industrial and consumer products.

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Lab products found in correlation

10 protocols using 10 undecenoic acid

Synthesis of Functionalized Styrene-Butadiene Rubber

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CNFs
were purchased from the Process Development
Center of University of Maine. SBR (KER 1502 SBR) was supplied by
Synthos S.A. N330 grade carbon black was acquired from Sid Richardson
Carbon & Energy Co. Sulfur, N-tert-butyl-2-benzothiazyl sulfonamide (TBBS), stearic acid, zinc oxide,
1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC), 4-dimethylaminopyridine
(DMAP), 4-pentenoic acid, 10-undecenoic acid, 3-mercaptopropionic
acid, 11-mercaptoundecanoic acid, cysteine, THF, anhydrous dimethylformamide
(DMF), and sodium hydroxide (NaOH) were of reagent grade and purchased
from Sigma-Aldrich.

Sinclair A., Zhou X., Tangpong S., Bajwa D.S., Quadir M, & Jiang L. (2019). High-Performance Styrene-Butadiene Rubber Nanocomposites Reinforced by Surface-Modified Cellulose Nanofibers. ACS Omega, 4(8), 13189-13199.

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Synthesis and Radical Scavenging Evaluation

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10-Undecenoic acid, 1,1’-azobis(cyclohexanecarbonitrile) (ABCN), hydroxybenzotriazole (HOBt) and 1-ethyl-3-(3’-dimethylaminopropyl)carbodiimide hydrochloride (EDC·HCl), cysteamine hydrochloride, cinnamic acid, sinapic acid, ferulic acid, p-coumaric acid, caffeic acid, α-tocopherol (α-TP), tert-butylhydroquinone (TBHQ), linoleic acid (LA) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical were purchased from Sigma–Aldrich (St.Louis, USA), and pre-coated TLC plates (silica gel 60 F254) were purchased from Merck (Darmstadt, Germany). All solvents were purchased from Sd Fine Chemicals (Mumbai, India) and were of the highest grade of purity available.

Narra N., Kaki S.S., Prasad R.B., Misra S., Dhevendar K., Kontham V, & Korlipara P.V. (2017). Synthesis and evaluation of anti-oxidant and cytotoxic activities of novel 10-undecenoic acid methyl ester based lipoconjugates of phenolic acids. Beilstein Journal of Organic Chemistry, 13, 26-32.

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Enzymatic Ester Synthesis via Immobilized Candida antarctica Lipase B

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Candida antarctica lipase B (CalB) immobilised on an acrylic carrier, >5000 U g⁻¹ (Novozyme 435), 10-undecenoic acid (UA), 11-mercaptoundecanoic acid (MUA), lipoic acid (LA), and 1,4-butanediol vinyl ether (BVE) were supplied by Sigma Aldrich. 1,6-Hexanediol vinyl ether (HVE) was supplied by BASF. All chemicals were used as received unless otherwise noted. Novozyme 435 was stored in a desiccator with saturated LiCl solution. The hydroxyl vinyl ether: BVE, and HVE, as well as solvents were stored with 4 Å molecular sieves.

Finnveden M., Brännström S., Johansson M., Malmström E, & Martinelle M. (2018). Novel sustainable synthesis of vinyl ether ester building blocks, directly from carboxylic acids and the corresponding hydroxyl vinyl ether, and their photopolymerization. RSC Advances, 8(44), 24716-24723.

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Polyhydroxyalkanoate Bioproduction Protocols

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A complete list of strains, plasmids, and primers used for this study can be found in Table 1. Unless otherwise specified, all strains were maintained in LB-Lennox (LB; composition per liter: 10 g tryptone, 5 g yeast extract, and 5 g NaCl, pH 7.0) purchased from Difco, and the antibiotics kanamycin (50 mg L^–1) and ampicillin (100 mg L^–1) were added to media as necessary. When necessary, Bacto agar (Difco) was added to media at a concentration of 15 g L^–1 to make plates.
The fatty acids hexanoic acid (Sigma Aldrich), sodium octanoate (Sigma Aldrich), decanoic acid (Alfa Aesar), and 10-undecenoic acid (Sigma Aldrich). 10-bromodecanoic acid (A.K. Scientific), and 10-azidodecanoate (synthesized as described below) were supplemented as substrates for polymer production as noted. Fatty acid feed solutions for bioreactor fermentations were brought to pH 8.0 by the addition of NaOH (10 M) to form the respective conjugate base and either autoclaved (saturated fatty acids) or filter-sterilized (functionalized fatty acids) prior to addition to the bioreactor.

Scheel R.A., Ho T., Kageyama Y., Masisak J., McKenney S., Lundgren B.R, & Nomura C.T. (2021). Optimizing a Fed-Batch High-Density Fermentation Process for Medium Chain-Length Poly(3-Hydroxyalkanoates) in Escherichia coli. Frontiers in Bioengineering and Biotechnology, 9, 618259.

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Enzyme-Catalyzed Peroxidase Assay Protocol

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A commercial peroxidase, Baylase® RP, was kindly donated by Bayer Mexico (Puebla, Mexico). Crystalline silicon was a product from Cemat Silicon (Warsaw, Poland). 10-undecenoic acid, N-ethyl-N′-(3-dimethylaminopropyl) carbodiimide (EDC), N-hydroxysuccinimide (NHS), 2, 2′-azino-bis (3 ethylbenzothiazoline-6-sulphonic acid) (ABTS), Guaiacol, and Remazol brilliant blue were purchased from Sigma-Aldrich (St. Louis, MO, USA). Bradford reagent was from Bio-Rad (Hercules, CA, USA). All other chemical reagents were of analytical grade and were used without further purification.

Sahare P., Ayala M., Vazquez-Duhalt R., Pal U., Loni A., Canham L.T., Osorio I, & Agarwal V. (2016). Enhancement of Peroxidase Stability Against Oxidative Self-Inactivation by Co-immobilization with a Redox-Active Protein in Mesoporous Silicon and Silica Microparticles. Nanoscale Research Letters, 11, 417.

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Nanocomposite Formation Protocol

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3-Aminopropyltriethoxysilane (APTES, 99%), N,N′-diisopropylcarbodiimide (DIC, 98%), 10-undecenoic acid (UD, 98%), undecanoic acid (UND, 98%), benzoic acid (BA, 99.5%) and 4-vinylbenzoic acid (vBA, 97%) were purchased from Sigma Aldrich and used without further purification. The solvents ethanol, ethyl acetate and acetone (technical grade) were obtained from VWR International. For the formation of the nanocomposites, monostyrene (with inhibitor) from BÜFA and CUROX M-312 as hardener from United Initiators were used as received.

Kockmann A., Porsiel J.C., Saadat R, & Garnweitner G. (2018). Impact of nanoparticle surface modification on the mechanical properties of polystyrene-based nanocomposites. RSC Advances, 8(20), 11109-11118.

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Colloidal Lead Halide Perovskite Synthesis

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Lead(II) acetate trihydrate (Pb(CH₃COO)₂·3H₂O, 99.99%), cesium carbonate
(Cs₂CO₃, 99%), benzoyl bromide (97%), 1-octadecene
(ODE, 90%), anhydrous ethyl acetate (99.8%), anhydrous acetone, toluene
(≥99.7%), deuterated toluene (toluene-d₈, 99.8 at. % D), deuterated dimethyl sulfoxide (d-DMSO, 99.9
atom. % D), oleic acid (OA, 90%), didodecyldimethylammonium
bromide (DDABr, 98%), 1-octylamine (99%), dioctylamine (98%), trioctylamine
(98%), 1-octanal (99%), dioctyl sulfide (96%), 1-octanoic acid (%),
10-undecenoic acid (98%), diisooctylphosphinic acid (90%), 1-octylphosphonic
acid (99%), 1-octanol (99%), and 1-octanethiol (98.5%) were purchased
from Sigma. Didodecylamine (DDA, 97%) and 9-heptadecanone (98%) were
purchased from TCI Chemicals. Trioctylphosphine (TOP, 97%) and Trioctylphosphine
oxide (99%, TOPO) were purchased from Strem Chemicals. All chemicals
were used without further purification.

Zaccaria F., Zhang B., Goldoni L., Imran M., Zito J., van Beek B., Lauciello S., De Trizio L., Manna L, & Infante I. (2022). The Reactivity of CsPbBr3 Nanocrystals toward Acid/Base Ligands. ACS Nano, 16(1), 1444-1455.

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Fabrication of Silicone Mechano-Variant Substrates

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Preparation of silicone mechano-variant substrates: Silicone gels were prepared by mixing pure liquid vinyl-terminated polydimethylsiloxane (PDMS) (1,000 cSt -DMS-VM31, Lot. 1K-39727. Gelest), hydrideterminated PDMS (500 cSt -DMS-HM25, Lot. 5L-26253. Gelest), 7-8% (Methylhydrosiloxane)dimethylsiloxane copolymer, trimethylsiloxy-terminated (AB146377, abcr GmbH) and Platinumdivinyltetramethyldisiloxane catalyst (AB146697, abcr GmbH). A small amount of 0.2% (v/v) 10-Undecenoic acid (124672, Sigma-Aldrich) was added to the mix to allow for direct coupling of primary amines. The gels' Young moduli were tuned by varying the amounts of crosslinker, vinyl-terminated, and hydride-terminated PDMS in the mix, while keeping the ratio of the platinum catalyst constant at 0.015% (v/v). To polymerize the gels, the silicone solution was thoroughly mixed, degassed under vacuum for 30 minutes and allowed to set at room temperature (for a total of one hour). Silicone mixture was then poured into desired cell culture vessels and cured at 70℃ for another 23 hours. Cured PDMS substrates were sterilized using UV light and 70-80% ethanol under aseptic conditions.

Hussien A.A., Niederöst B., Bollhalder M., Goedecke N., & Snedeker J.G. (2021). The stiffness-sensitive transcriptome of human tendon stromal cells.

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Synthesis and Purification of 2-Oxazoline Monomers

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2-Ethyl-2-oxazoline, 2-phenyl-2-oxazoline, butyronitrile, acetonitrile, ethyl acetate, dimethyl carbonate, methyl p-toluene sulfonate, ethanolamine, titanium(iv) oxide, barium oxide, benzoyl chloride, decanoic acid, 10-undecenoic acid and octanoic acid were purchased from Merck and cadmium acetate from Acros Organics. 2-Heptyl-2-oxazoline, 2-nonyl-2-oxazoline, 2-dec-9′-enyl-2-oxazoline were prepared according to literature.^{16,47 (link)} 2-isopropyl-2-oxazoline and 2-butyl-2-oxazoline were synthesized following literature.^{48,49 (link)} Butyronitrile was stored over molecular sieve 3 Å. Each 2-oxazoline monomer was vacuum-distilled twice: first over barium oxide, then after addition of 1 vol% of benzoyl chloride. Freshly distilled monomers were stored over argon at 4 °C. All other chemicals were used as received.

Abbrent S., Mahun A., Smrčková M.D., Kobera L., Konefał R., Černoch P., Dušek K, & Brus J. (2021). Copolymer chain formation of 2-oxazolines by in situ1H-NMR spectroscopy: dependence of sequential composition on substituent structure and monomer ratios. RSC Advances, 11(18), 10468-10478.

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Membrane Support Material Preparation

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Hydrochloric acid (37%), sodium borohydride (NaBH₄, 37.83 g/mol, pH value of 11 (10 g/L solution in water)), i–propanol, t–butanol and n–decanol were used without additional purification as supplied by the manufacturer (Merck KGaA, Darmstadt, Germany).
Osmium tetroxide (OsO₄), undecylenyl alcohol (11–hydroxy–1–undecene or 10–undecen–1–ol), 10–undecylenic acid or 10–undecenoic acid (>95%), and p–nitrophenol, are from Sigma-Aldrich (Merck KGaA, Darmstadt, Germany).
The pure water used for the preparation of all the solutions used in the experiments was obtained with a standard system MilliQ^® Direct 8 RO Water Purification System (Merck, Darmstadt, Germany). The characteristic conductivity of the water obtained through the reverse osmosis system is 18.2 μs/cm.
As a membrane support material, a bundle of polypropylene fibers (surface 1 m²/bundle) was purchased from GOST Ltd. (GOST Ltd., Perugia, Italy). To maintain the fibers’ characteristics, they were conditioned with polyols. Their morphological, structural and process characteristics were previously presented in detail [36 ,37 (link),38 (link)].

Albu P.C., Ferencz (Dinu) A., Al-Ani H.N., Tanczos S.K., Oprea O., Grosu V.A., Nechifor G., Bungău S.G., Grosu A.R., Goran A, & Nechifor A.C. (2021). Osmium Recovery as Membrane Nanomaterials through 10–Undecenoic Acid Reduction Method. Membranes, 12(1), 51.

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