Pyrrolidine

Manufactured by Merck Group

Sourced in United States

Pyrrolidine is a heterocyclic organic compound with the chemical formula C₄H₉N. It is a colorless, flammable liquid with a characteristic amine-like odor. Pyrrolidine is commonly used as a building block in the synthesis of various pharmaceutical and industrial chemicals.

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Lab products found in correlation

21 protocols using pyrrolidine

Syndiotactic Polystyrene Dissolution in Various Solvents and Ionic Liquids

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SPS was kindly supplied
by Idemitsu Kosan
Co., Ltd. It is 98% syndiotactic with an M_w of 152 000, and an M_w/M_n of 1.9. SPS was dissolved with a solvent in
a screw tube by heating the mixture at high temperature after influx
of dry nitrogen gas for 1 min. The solvents used included chloroform,
Py, toluene, THF (Wako Co.), piperidine, and pyrrolidine (Sigma-Aldrich).
The ILs used were 1-butylpyridinium bromide ([C₄py]Br)
(Sigma-Aldrich, Tokyo Kasei), 1-butyl-4-methylpyridinium tetrafluoroborate
(Sigma-Aldrich), and 1-butylpyridinium bis(trifluoromethanesulfonyl)imide
(Tokyo Kasei). All of the ILs and solvents were used without purification.
The heating temperature of a sample was sometimes higher than the
boiling temperature of the solvent by 10–20 °C. In the
case of SPS/Py gels and SPS/pyrrolidine gels with 5–10 wt %
SPS, the heating temperatures were 130–140 and 120–130
°C, respectively. After SPS was perfectly dissolved, the solutions
were well stirred by using a vortex mixer, heated again for 2 min,
and finally cooled at room temperature (around 25 °C) for 1 day.

Itagaki H., Yoshida N., Sano T., Yokoyama M., Iba N., Sugiyama R, & Kuroki M. (2019). Electrically Conductive Gels Prepared from Syndiotactic Polystyrene and an Ionic Liquid. ACS Omega, 4(14), 16125-16129.

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Synthesis and Analysis of Organophosphate Compounds

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BDCIPP, d₁₀-BDCIPP, and d₁₂-tris(chloroethyl) phosphate (d₁₂-TCEP), TBBA and ¹³C₆-TBBA were purchased from Wellington Laboratories (Guelph, ON). Bis(1-chloro-2-propyl) phosphate (BCIPP) and d₁₀-DPHP were synthesized by the Max Planck Institute for Biophysical Chemistry (Goettingen, Germany). The ip-PPP, tert-butyl-phenyl phenyl phosphate (tb-PPP), ¹³C₂-DPHP were synthesized by the Small Molecule Synthesis Facility at Duke University (Durham, NC). 1-hydroxy-2-propyl bis(1-chloro-2-propyl) phosphate (BCIPHIPP) was a gift from Professor Adrian Covaci, University of Antwerp (Antwerp, Belgium).
Ammonium acetate, trimethylamine, pyrrolidine and 2,3,5-triiodobenzoic acid (TIBA), β-glucuronidase from limpets (>1M units/g) and sulfatase from Helix pomatia (>10,000 units/g) were purchased from Sigma-Aldrich (St. Louis, MO). StrataX-AW (60 mg, 3 ml) solid phase extraction columns (SPE) and the Luna C18(2) (2.5 µm, 50 × 2 mm) analytical column were purchased from Phenomenex (Torrance, CA, USA). Methanol and acetonitrile were HPLC grade (EMD Millipore Corporation, Bellerica, MA).

Butt C.M., Hoffman K., Chen A., Lorenzo A., Congleton J, & Stapleton H.M. (2016). Regional Comparison of Organophosphate Flame Retardant (PFRs) Urinary Metabolites and Tetrabromobenzoic Acid (TBBA) In Mother-Toddler Pairs from California and New Jersey. Environment international, 94, 627-634.

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TiO2 Enrichment of Phosphopeptides from iTRAQ Samples

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Phosphopeptides from each 4plex iTRAQ™ sample set were enriched using TiO₂ microcolumns (TitanSphere Phos-TiO Kit, GL Sciences). Prior to enrichment, four TiO₂ microcolumns per 4plex iTRAQ™ sample were conditioned using wash buffer (80% acetonitrile and 5% trifluoroacetic acid (TFA)) followed by loading buffer. The 4plex iTRAQ™ sample was resuspended in loading buffer labeled as solution 1 (1M lactic acid, 80% acetonitrile with 5%, TFA) and loaded evenly onto the four conditioned columns by centrifugation (1000 × g for 10 min). Columns were washed twice using loading buffer and wash buffer, respectively. Phosphopeptides were then sequentially eluted from columns using 50% acetonitrile with 50 mM TEAB (solution 2), 50% acetonitrile with 500 mM ammonium hydroxide (solution 3) and 50% acetonitrile with 5% pyrrolidine (solution 4) (Sigma, St. Louis). All elutions were collected separately (Fig. 1). Elutions using solution 2 from all four columns were pooled. Similarly, elutions from solution 3 and from solution 4 from all four columns were pooled to generate three fractions per sample. These fractions were dried under vacuum and resuspended in 50 μL of H₂O containing 3% acetonitrile and 0.1% formic acid prior to LC-MS/MS analysis.

Kheterpal I., Scherp P., Kelley L., Wang Z., Johnson W., Ribnicky D, & Cefalu W.T. (2014). Bioactives from Artemisia dracunculus L. Enhance Insulin Sensitivity via Modulation of Skeletal Muscle Protein Phosphorylation. Nutrition (Burbank, Los Angeles County, Calif.), 30(0 0), S43-S51.

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HPLC Analysis of Amino Acids and Amines

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HPLC-grade acetonitrile and methanol were from Merck. Hydrochloric acid (HCl), glycine and hydroxylamine (>97.5%) were purchased from Reakhim. DEEMM and L-ornithine monohydrochloride (≥99%) was obtained from Fluka. Boric acid (≥99%) was purchased from Hopkin & Williams. Amino acid commercial standards (L-alanine, L-arginine hydrochloride, L-asparagine, L-aspartic acid, L-glutamine, L-glutamic acid, L-glycine, L-histidine, L-isoleucine, L-leucine, L-lysine, L-methionine, L-phenylalanine, L-proline, L-serine, L-threonine, L-tryptophan, L-tyrosine and L-valine, ≥99.5%), γ-aminobutyric acid (≥99%), formic acid (≥95%), putrescine (≥99.5%), phenyethylamine (≥99.5%), tyramine hydrochloride (≥98%), ethylamine hydrochloride (98%), methylamine solution (40%), pyrrolidine (99%), ethanolamine (≥98%) and taurine (≥99%) were purchased from Sigma; dopamine hydrochloride (99%), histamine dihydrochloride (≥98%) were purchased from Alfa Aesar; L(+)-α-aminobutyric acid (98%) were purchased from Acros Organics; β-aminobutyric acid (98%) were purchased from BLD Pharmatec. Ultrapure water was supplied by a Millipore Milli-Q Advantage A10 (Millipore) and 0.75 M borate buffer at pH = 9 was prepared in deionized water.

Marengo A., Maciel L.S., Cagliero C., Rubiolo P, & Herodes K. (2023). Free Amino Acids and Biogenic Amines Profiling and Variation in Wild and Sub-Endemic Cardueae Species from Sardinia and Corse. Plants, 12(2), 319.

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Odor Compound Procurement Protocol

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Eugenol, CS₂, 2,3-DMP, 2,5-DMP, OA, ALA, indole, quinoline, pyridine, pyrrolidine, vanillin, and IAA were purchased from Sigma-Aldrich. TMT was purchased from BioSRQ. All odor compounds were obtained at the highest purity possible.

Jiang H.C., Park S.J., Wang I.H., Bear D.M., Nowlan A, & Greer P.L. (2024). CD20/MS4A1 is a mammalian olfactory receptor expressed in a subset of olfactory sensory neurons that mediates innate avoidance of predators. Nature Communications, 15, 3360.

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Volatile Organic Compound Analysis

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Eugenol, CS₂, 2,3-DMP, 2,5-DMP, OA, ALA, indole, quinoline, pyridine, pyrrolidine, vanillin, and isoamyl alcohol (IAA) were purchased from Sigma-Aldrich. TMT was purchased from BioSRQ. All odor compounds were obtained at the highest purity possible.

Jiang H.C., Park S.J., Wang I.H., Bear D.M., Nowlan A, & Greer P.L. (2023). CD20 is a mammalian odorant receptor expressed in a subset of olfactory sensory neurons that mediates innate avoidance of predators. Research Square.

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Synthesis of Colloidal Nanocrystal Superlattices

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Benzene (99.8%, anhydrous), n-butanol (99.8%,
anhydrous), 1-chloropentane (99%), cyclohexyl isocyanide
(98%), diphenylphosphine (98%), hexane (mixture of isomers, ≥99%,
anhydrous), isopropanol (99.5%, anhydrous), lead acetate trihydrate
(≥99.99%), methanol (99.8%, anhydrous), 1-octadecene (90%),
octane (≥99%, anhydrous), oleic acid (90%), pyrrolidine (≥99%),
selenium powder (99.99%, −100 mesh), tetrachloroethylene (≥99%,
anhydrous), toluene (99.8%, anhydrous), triethylamine (≥99%),
trifluoroacetic acid (99%), trifluoroacetic anhydride (≥99%),
trimethylbenzene (98%), and trioctylphosphine (90%) were purchased
from Sigma-Aldrich and used without further purification. Lead (II)
oxide (99.999+%) was purchased from Strem Chemicals. 1,4-Butanediol
(BD, 99%, ReagentPlus), di ethylene glycol (DEG, 99%), diphenyl ether
(≥99%), ethylene glycol (EG, 99.8%, anhydrous), and hexadecane
(≥99%) were purchased from Sigma-Aldrich and degassed under
vacuum for ∼14 h at 60 °C prior use. For superlattice
formation, a distillation of the EG did not result in a significant
difference in the quality of the formed superlattice (see Figure S1).

van der Sluijs M.M., Sanders D., Jansen K.J., Soligno G., Vanmaekelbergh D, & Peters J.L. (2022). On the Formation of Honeycomb Superlattices from PbSe Quantum Dots: The Role of Solvent-Mediated Repulsion and Facet-to-Facet Attraction in NC Self-Assembly and Alignment. The Journal of Physical Chemistry. C, Nanomaterials and Interfaces, 126(2), 986-996.

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Thiol-Containing Macromolecule Synthesis

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All reagents were purchased from commercial sources or synthesized and used without further purification unless specified. They were poly(ethylene glycol) methyl ether (mPEG_5k-OH, M_n = 5.4 × 10³ g/mol measured by ¹H NMR), 1-(3,5-bis-trifluoromethyl-phenyl)-3-cyclohexylthiourea (TU, synthesized)^{41 (link)}, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, >99%, Sigma-Aldrich), dipropylamine (DPA, 99%, Sigma-Aldrich), dibutylamine (DBA, >99.5%. Sigma-Aldrich), pyrrolidine (C5A, >99%, Sigma-Aldrich), piperidine (C6A, >99.5%), hexamethyleneimine (C7A, 99%, Sigma-Aldrich), ethylene sulfide (98%, Sigma-Aldrich), 2,2-dimethoxy-2-phenylacetophenone (DMPA, 99%, Sigma-Aldrich). 2-Dimethylaminoethanethiol hydrochloride (DMA-SH·HCl, 95%) and 2-diethylaminoethanethiol hydrochloride (DEA-SH·HCl, 95%) were purchased from Sigma-Aldrich. Other aminothiol hydrochloride molecules (Supplementary Fig. 1) were synthesized as reported^{42 (link)}.

Wang X., Wilhelm J., Li W., Li S., Wang Z., Huang G., Wang J., Tang H., Khorsandi S., Sun Z., Evers B, & Gao J. (2020). Polycarbonate-based ultra-pH sensitive nanoparticles improve therapeutic window. Nature Communications, 11, 5828.

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Odorant-Induced Neuronal Connectivity

Cited 2 times

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Staged animals at either eclosion (0 dpe) or maturity (7 dpe) were exposed to odorants for 24 hours at RT. pyrrolidine was selected based on specific activation of the Ir75d receptor [29 (link)], which is expressed in olfactory sensory neurons that innervate the VL1 glomerulus [30 (link)], presynaptic to the mPN2 dendritic arbor [15 (link), 18 (link)]. Ethyl acetate was used to activate the DM1 glomerulus [31 (link)]. Olfactory exposure was done within a sealed 50 mL conical tube. Mineral oil control (500μL) or pyrrolidine (1:100 dilution; #394238, Sigma-Aldrich) was placed in a closed 1.5 mL microcentrifuge tube, with the cap center punctured by a 20 gauge needle. Genetic background (w¹¹¹⁸) control and dfmr1 null (dfmr1^50M) mutants expressing R65G01-Gal4>UAS-mCD8::GFP were used to assess PN architecture and connectivity following odorant exposure.

Doll C.A., Vita D.J, & Broadie K. (2017). Fragile X Mental Retardation Protein Requirements in Activity-Dependent Critical Period Neural Circuit Refinement. Current biology : CB, 27(15), 2318-2330.e3.

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Purification of Polymers using Dialysis Bags

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Dialysis bags “CellaSep”, MWCO = 3000 Da (Orange Scientific, Braine-l′Alleud, Belgium) were used for the purification of polymer samples. Monomers, 2-ethyl- and 2-isopropyl-2-oxazolines (Sigma-Aldrich, St. Louis, MO, USA) were distilled over the calcium hydride. Sulfolane (Sigma-Aldrich, St. Louis, MO, USA) was purified by vacuum distillation. Pyrrolidine (Sigma-Aldrich, St. Louis, MO, USA) was distilled over calcium hydride.

Kirila T., Amirova A., Blokhin A., Tenkovtsev A, & Filippov A. (2021). Features of Solution Behavior of Polymer Stars with Arms of Poly-2-alkyl-2-oxazolines Copolymers Grafted to the Upper Rim of Calix[8]arene. Polymers, 13(15), 2507.

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