Cinnamaldehyde and 2,4,5-tri-amino-6-oxo-dihydropyrimidine dihydrochloride were purchased from Millipore Sigma and Santa Cruz Biotechnology (Dallas, TX, USA), respectively. The 2-bromo-3-phenyl-propionaldehyde (3 g, 14 mmol) was re-dissolved in ethanol (50 ml) followed by the addition of 2,4,5-tri-amino-6-oxo-dihydropyrimidine dihydrochloride (3 g, 15 mmol) and sodium bicarbonate (4 g, 47 mmol) in water (30 ml). The mixture was refluxed for 1 h and cooled down to room temperature. Hydrogen peroxide solution (30%, 12 ml) was added to the mixture and stirred overnight. The precipitate was filtered and washed with water and acetone to yield colipterin 3 (1.2 g, 38%). For colipterin 4 , colipterin 3 (1 g, 4 mmol) was re-suspended in water (100 ml) and refluxed with potassium permanganate (1.5 g, 9.6 mmol) for 1 h. After cooling down, the precipitate was filtered with Celite and the filtrate was acidified with 50% acetic acid. The precipitate was then collected using a glass filter. Synthetic colipterins 3 and 4 were purified as described in “Isolation of Metabolites.” 810 mg (78%) of synthetic 4 was obtained from this synthesis.
Cinnamaldehyde
Manufactured by Merck Group
Sourced in United States, Germany, Brazil, United Kingdom, Spain, Portugal, Australia, Sao Tome and Principe, India
Cinnamaldehyde is a chemical compound used in various laboratory applications. It is a pale yellow liquid with a characteristic cinnamon-like aroma. Cinnamaldehyde serves as a key ingredient in many fragrance and flavoring formulations.
Automatically generated - may contain errors
Lab products found in correlation
Eugenol, by Merck Group (19 mentions)
Capsaicin, by Merck Group (15 mentions)
Menthol, by Merck Group (15 mentions)
Thymol, by Merck Group (12 mentions)
Carvacrol, by Merck Group (12 mentions)
Dimethyl sulfoxide (dmso), by Merck Group (11 mentions)
Cinnamic acid, by Merck Group (11 mentions)
Vanillin, by Merck Group (7 mentions)
Linalool, by Merck Group (6 mentions)
Citral, by Merck Group (6 mentions)
Coumarin, by Merck Group (6 mentions)
Indomethacin, by Merck Group (5 mentions)
Geraniol, by Merck Group (5 mentions)
Acetic acid, by Merck Group (4 mentions)
Methanol, by Merck Group (4 mentions)
Sodium hydroxide (naoh), by Merck Group (4 mentions)
Allyl isothiocyanate, by Merck Group (4 mentions)
Hc 030031, by Merck Group (4 mentions)
Bovine serum albumin (bsa), by Merck Group (4 mentions)
Curcumin, by Merck Group (3 mentions)
117 protocols using cinnamaldehyde
1
Synthesis and Purification of Colipterins 3 and 4
2
Synthesis and Purification of Colipterins 3 and 4
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Cinnamaldehyde and 2,4,5-tri-amino-6-oxo-dihydropyrimidine dihydrochloride were purchased from Millipore Sigma and Santa Cruz Biotechnology (Dallas, TX, USA), respectively. The 2-bromo-3-phenyl-propionaldehyde (3 g, 14 mmol) was re-dissolved in ethanol (50 ml) followed by the addition of 2,4,5-tri-amino-6-oxo-dihydropyrimidine dihydrochloride (3 g, 15 mmol) and sodium bicarbonate (4 g, 47 mmol) in water (30 ml). The mixture was refluxed for 1 h and cooled down to room temperature. Hydrogen peroxide solution (30%, 12 ml) was added to the mixture and stirred overnight. The precipitate was filtered and washed with water and acetone to yield colipterin 3 (1.2 g, 38%). For colipterin 4 , colipterin 3 (1 g, 4 mmol) was re-suspended in water (100 ml) and refluxed with potassium permanganate (1.5 g, 9.6 mmol) for 1 h. After cooling down, the precipitate was filtered with Celite and the filtrate was acidified with 50% acetic acid. The precipitate was then collected using a glass filter. Synthetic colipterins 3 and 4 were purified as described in “Isolation of Metabolites.” 810 mg (78%) of synthetic 4 was obtained from this synthesis.
3
Amino Acid and Volatile Compound Analysis
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An EZ:faastTM amino acid analysis kit (category number KG0-7166) was purchased from Phenomenex (Torrance, CA, USA). The amino acid kit includes two sets of amino acid standards which were SD1 (23 amino acids) and SD2 (3 amino acids). Two other amino acids, citrulline and arginine, were analytical standard grade and obtained from MilliporeSigma (Milwaukee, WI, USA). Water, methanol, ethanol, and acetonitrile were HPLC grade and obtained from Fisher Scientific (Fair Lawn, NJ, USA). Phosphoric acid and monopotassium phosphate were analytical grade and obtained from Fisher Scientific. A total of 33 volatile standards (acetaldehyde; pentanal; hexanal; pentyl acetate; 2-heptanone; (E)-2-hexenal; octanal; 6-methyl-5-heptanone; hexanol; cis-3-hexenol; nonanal; trans-2-hexenol; trans-2-octenal; cis-6-nonenal; benzaldehyde; trans-2-nonenal; linalool; 2,6-nonadienal; E-2-decanal; nonanol; cis-6-nonenol; E-2-nonenol; 2,6-nonadienol; E,E-2,4-decadienal; tridecanal; geraniol; hexanoic acid; benzyl alcohol; cinnamaldehyde; β-ionone; γ-nonalactone; ethyl cinnamate; and nonanoic acid) with purity ≥ 98% were purchased from MilliporeSigma. Sodium chloride was purchased from Fisher (ACROS Organics, Fair Lawn, NJ, USA). The C6–C26 alkane mixture was obtained from MilliporeSigma.
4
Pharmacological Evaluation of Analgesic Agents
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The following drugs and chemicals were used in the current study: morphine sulphate, diclofenac sodium, naloxone (Hameln Pharmaceuticals GmbH), acetic acid, methanol, formalin, cinnamaldehyde, methylene blue, L-glutamic acid (Merck, Germany), glibenclemide (Square Pharmaceuticals Ltd., Bangladesh), and DMSO (Merck, Germany).
5
Sensory Neuron Characterization Protocol
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Solutions for determining acid sensitivity (pH 7, pH 6, pH 5) and TRP-agonist sensitivity (capsaicin, cinnamaldehyde and menthol) were applied in a random order through a gravity-driven 12 barrel perfusion system (Dittert et al., 2006 (link)) to DRG neurons in 5 s pulses with at least 30 s wash period (with pH 7.4) between stimuli. Solutions of 10 μM capsaicin (1 mM stock in 100% ethanol; Sigma-Aldrich), 100 μM cinnamaldehyde (10 mM stock in 100% ethanol; Merck) and 100 μM menthol (20 mM stock in 100% ethanol; Alfa Aesar) were made up in pH 7.4 extracellular solution from their respective stock solutions. Neurons that produced an inward current, time-locked to drug application, were counted as responders; in control experiments using the vehicle control (1% EtOH, n = 3) no such inward currents were observed. Current amplitude was measured in Fitmaster (HEKA) by subtracting the maximum peak response from the baseline (average of the first 3 s before stimulation), which was then normalized by dividing by neuron capacitance to give current density.
6
Antimicrobial Zein-based Nanoparticles
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Tetraethyl orthosilicate (TEOS), triethanolamine (TEAH3), sodium hydroxide (NaOH), N-cetyltrimethylammonium bromide (CTAB), (3-aminopropyl)triethoxysilane (APTES), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (EDC), trifluoroacetic acid (TFA), rhodamine B (RhB), thymol (Thy), carvacrol (Car) and cinnamaldehyde (Cin) were provided by Sigma-Aldrich (Sigma-Aldrich Química S.L., Madrid, Spain). Alpha-zein (corn protein) (zein), ethanol (extra pure), methanol (MeOH), acetonitrile (ACN), hexane and dimethyl sulfoxide (DMSO) were purchased from Scharlab (Barcelona, Spain). Escherichia coli K12 (CECT 433) was obtained from the Spanish Type Culture Collection (CECT, Burjassot, Spain). The bacterial strain was reconstituted according to the CECT instructions. After that, the bacterial stock was maintained at 4 °C in a plate count agar before its use. E. coli inoculum was prepared by placing one single colony of the E. coli strain into 10 mL of tryptic soy broth (TSB). The mixture was incubated at 37 °C for 24 h in order to obtain an inoculum with a density of approximately 108 cells/mL of broth. All culture media were supplied by Scharlab S.A. (Barcelona, Spain).
7
Compound Preparation for Biological Assays
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Curcumin, azathioprine, resveratrol, catechin hydrate, baicalin hydrate, L-canavanine, 4-nitropyridine N-oxide, p-benzoquinone, esculin hydrate, cinnamaldehyde, and ciprofloxacin were purchased from Sigma Chemical Co. (St. Louis, MO, USA). Stock solutions of ciprofloxacin and the compounds were prepared in dimethyl sulfoxide (pure DMSO), sterile water, or hydrochloric acid according to the manufacturer’s recommendations.
8
Preparation of Pharmaceutical Compounds
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Citric acid monohydrate, acetyl-β-methylcholine chloride, salbutamol sulfate, atropine, cinnamaldehyde, codeine phosphate, chlorpheniramine maleate (Sigma-Aldrich, Poole, UK), and levodropropizine, (Eurodrug, The Hague, Netherlands), were all dissolved in sterile saline (0.9%; Baxter Healthcare Ltd., Thetford, UK). Tiotropium bromide (Chiesi Farmaceutici, Parma, Italy) was prepared as a stock solution of 6 mM and diluted with sterile saline. All drugs were prepared fresh on the day of use. Roflumilast (CAS162401-32-3; Kemprotec, Carnforth, UK) is poorly soluble in saline and was therefore prepared in neat solutol (2%, Kolliphor HS15, 42966; Sigma-Aldrich) and diluted to the final concentration on the day of use. Capsaicin (Sigma-Aldrich) was prepared as a stock solution of 25 mg/ml (8:1:1 saline:ethanol:Tween 20; Fisher Scientific, Loughborough, UK). HC-030031 (2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-7H-purin-7-yl)-N-(4-isopropylphenyl)acetamide; Chiesi Farmaceutici) was prepared as a stock solution of 300 mg/ml in sterile saline and 1% solutol.
9
Extraction and Characterization of C. tamala Essential Oil
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The leaves of C. tamala were collected from Almora, Uttarakhand, India. The leaves were partially shade dried and used for extraction of EO. On hydro-distillation, the partially shade dried leaves yielded 1.2% pale yellow color EO. After distillation, the EO was dried over by adding a pinch of anhydrous sodium sulfate and stored at 4°C until further analysis and experiments. The EO was quantitative and qualitatively analyzed by GC-FID and GC-MS following the methods and conditions used by Sriramavaratharajan et al. (2016) (link). The individual component of the EO such as cinnamaldehyde (#W228613) and linalool (#L2602) was purchased from Sigma–Aldrich.
10
Spice Compound Effects on TRPV1 and TRPM8
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The effects of the active ingredients of five naturally occurring spices (Capsaicin - red chili; eugenol - cloves; cinnamaldehyde - cinnamon; menthol - mint; allyl isothiocianate - wasabi; radish; and mustard) and one artificial spice analog (icilin) were investigated. Capsaicin4 (link) and eugenol9 (link) bind to TRPV1, menthol15 (link) and icilin17 (link) bind to TRPM8, and cinnamaldehyde and allyl isothiocyanate (AITC) bind to TRPA120 . To improve solubility, the compounds were dissolved in dimethyl sulfoxide (DMSO) to form a stock solution, which does not affect electrophysiological properties37 (link).
Capsaicin, icilin, eugenol, menthol and cinnamaldehyde were obtained from Sigma - Aldrich. AITC was obtained from Spectrum Chemical MFG. Corp.
Capsaicin, icilin, eugenol, menthol and cinnamaldehyde were obtained from Sigma - Aldrich. AITC was obtained from Spectrum Chemical MFG. Corp.
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