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Allyl alcohol

Allyl alcohol is a colorless, flammable liquid with a pungent odor.
It is used as a chemical intermediate in the production of other compounds, such as glycerol and acrylic acid.
Allyl alcohol can be hazardous if inhaled or absorbed through the skin, and exposure may cause irritation to the eyes, nose, and throat.
Proper precautions and personal protective equipment are required when handling this substance.
Researchers can utilize PubCompare.ai's AI-driven protocols to improve the reproducibility and accuracy of their allyl alcohol experiments, easily accessing and comparing protocols from literature, pre-prints, and patents to find the best methodologies and products for their work.

Most cited protocols related to «Allyl alcohol»

RNA Extraction and Amplification Protocol

Cited 4 times

RNA was extracted from tissue homogenate in a chaotropic buffer using phenol/cholorform/isoamyl alcohol. All reagents were from Sigma unless otherwise noted. Tissues were removed from RNAlater, blotted dry, and homogenized using an electric homogenizer in 400 μl chaotropic buffer (4.5 M guanidinium thiocyanate, 2% N-lauroylsarcosine, 50 mM EDTA pH 8.0, 25 mM Tris-HCl pH 7.5, 0.1 M β-mercaptoethanol, 2% antifoam A). An equal volume of 2 M sodium acetate (pH 4.0) was added to the homogenate, followed by 400 μl acidic phenol (pH 4.4), and 120 μl chloroform/isoamyl alcohol (23:1). The mixture was kept at 4°C for 10 min then centrifuged at 4°C at 16,000g for 20 min. Supernatant was removed and combined with 400 μl isopropanol, stored at -20°C for 30 min, then centrifuged at 4°C at 16,000g for 30 min. The remaining RNA pellet was rinsed twice with 400 μl of 70% ethanol, then further purified using the Qiagen RNeasy Mini kit (Qiagen) following the manufacturer's protocols. Purified RNA was quantified spectrophotometrically, and RNA quality was assessed using the Agilent 2100 Bioanalyzer. RNA was stored in 1/10 volumes 3 M sodium acetate and 2.5 volumes 100% ethanol at -20°C.
RNA for hybridization was prepared by amplification using a modified Eberwine protocol [28 (link)]. The Ambion Amino Allyl MessageAmp aRNA Kit was used (according to manufacturer's protocols) to copy template RNA by T7 amplification following incorporation of a T7 promoter, resulting in amplified template in the form of antisense RNA. Amino-allyl UTP was incorporated into targets during T7 transcription, and resulting amino-allyl antisenseRNA was coupled to Cy3 and Cy5 dyes (Amersham Biosciences).

Whitehead A, & Crawford D.L. (2005). Variation in tissue-specific gene expression among natural populations. Genome Biology, 6(2), R13.

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Publication 2005

2-Mercaptoethanol Antisense RNA Buffers Chloroform Crossbreeding Dyes Edetic Acid Electricity Ethanol guanidine thiocyanate hydroxybenzoic acid isopentyl alcohol Isopropyl Alcohol N-lauroylsarcosine Phenol Sodium Acetate Tissues Transcription, Genetic Tromethamine

Standardized Fungal Growth Conditions

Cited 4 times

All strains used in this study were derived from Guy11 (Table S4). Strains were grown on complete medium (CM) containing 1% (W/V) glucose, 0.2% (W/V) peptone, 0.1% (W/V) yeast extract and 0.1% (W/V) casamino acids, or on minimal medium (MM) containing 1% glucose and 0.6% sodium nitrate, unless otherwise stated, as described in [21] (link). 55 mm petri dishes were used unless stated otherwise. Allyl alcohol (ACROS organics, USA), kanamycin (Fisher, USA), sorbose (Sigma, USA), 2-deoxyglucose (Sigma, USA) and ethionine (Sigma, USA) were added to CM or MM in the amounts indicated. Plate images were taken with a Sony Cyber-shot digital camera, 14.1 mega pixels. Nitrate reductase enzyme activity was measured as described previously [21] (link). For spore counts, 10 mm² blocks of mycelium were transferred to the centre of each plate, and the strains grown for 12 days at 26°C with 12 hr light/dark cycles. Spores harvested in sterile distilled water, vortexed vigorously and counted on a haemocytometer (Corning). Spores were counted independently at least four times. Rice plant infections were made using a susceptible dwarf Indica rice (Oryza sativa) cultivar, CO-39, as described previously [23] (link). Fungal spores were isolated from 12–14 day-old plate cultures and spray-inoculated onto rice plants of cultivar CO-39 in 0.2% gelatin at a concentration of 5×10⁴ spores/ml, unless otherwise stated, and disease symptoms were allowed to develop under conditions of high relative humidity for 96–144 hrs.

Fernandez J., Wright J.D., Hartline D., Quispe C.F., Madayiputhiya N, & Wilson R.A. (2012). Principles of Carbon Catabolite Repression in the Rice Blast Fungus: Tps1, Nmr1-3, and a MATE–Family Pump Regulate Glucose Metabolism during Infection. PLoS Genetics, 8(5), e1002673.

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Publication 2012

2-Deoxyglucose allyl alcohol casamino acids Dwarfism enzyme activity Ethionine Fingers Gelatins Glucose Humidity Hyperostosis, Diffuse Idiopathic Skeletal Infection Kanamycin Mycelium Nitrate Reductase Oryza sativa Peptones sodium nitrate Sorbose Spore Count Spores Spores, Fungal Sterility, Reproductive Strains Yeast, Dried

Synthesis of Functional Polymers via Click Chemistry

Cited 3 times

1,3-Bis(isocyanatomethyl)cyclohexane, 1,3-bis(2-isocyanatopropan-2-yl)benzene, 4,4-methylenebis(cyclohexyl isocyanate), 4,4′-methylenebis(phenyl isocyanate), bis(4-hydroxyphenyl)methane, 6-chloro-1-hexanol, 8-chloro-1-octanol, dibutyltin dilaurate sodium azide, 1,1,1-tris(hydroxymethyl)propane, tris-1,3,5-bromomethylbenzene, phloro-glucinol, propargyl alcohol, propargyl bromide, allyl bromide, sodium hydride (NaH), sodium sulfate (Na₂SO₄), potassium thioacetate, diethyl azodicarboxylate (DEAD), tetrabutylammonium iodide, N,N,′,N′,N″ -pentamethyldiethylenetriamine (PMDETA), copper(II) chloride, 2,2-dimethoxy-2-phenylacetophenone (DMPA), triphenyl-phosphine (TPP), tetrahydrofuran (THF), dimethylformamide (DMF), and dimethyl sulfoxide (DMSO) were all purchased from Sigma-Aldrich and used without further purification. Potassium carbonate (K₂CO₃) and hydrochloric acid (HCl) were purchased from Fisher Scientific and used without further purification.

Baranek A., Song H.B., McBride M., Finnegan P, & Bowman C.N. (2016). Thermomechanical Formation–Structure–Property Relationships in Photopolymerized Copper-Catalyzed Azide–Alkyne (CuAAC) Networks. Macromolecules, 49(4), 1191-1200.

Publication 2016

allyl bromide Benzene Chlorides Copper Cyclohexane dibutyltin dilaurate Dimethylformamide Hexanols Hydrochloric acid Isocyanates Methane Octanols phenyl isocyanate Potassium potassium carbonate Propane propargyl alcohol propargyl bromide Sodium Azide sodium hydride sodium sulfate Sulfoxide, Dimethyl tetrabutylammonium iodide tetrahydrofuran triphenylphosphine Tromethamine

Synthesis of Deuterated Allylaniline Intermediate

Cited 3 times

A solution of LiAlD₄ (3.6 g, 85.6 mmol, 1.6 equiv) in dry Et₂O (285 mL) was cooled to −10°C and a solution of propargyl alcohol (3.0 g, 53.5 mmol, 1 equiv) in Et₂O (33 mL) was added through an addition funnel over 30 min. The resulting solution was warmed to room temperature and stirred for 14 h. The mixture was cooled to 0°C and was quenched slowly with H₂O (4.0 mL). The solution was stirred for another 15 min and then 15% aqueous NaOH solution (4.0 mL) and H₂O (4.0 mL) were added. The white slurry was filtered through a short pad of Celite and was washed with Et₂O (300 mL). The filtrate was concentrated in vacuo to give the crude allyl-2-d₁ alcohol⁴ as a yellow oil (3.0 g). ¹H NMR (500 MHz, CDCl₃): δ = 5.22 (s, 1H), 5.09 (s, 1H), 4.08 (s, 2H), 3.0 ppm (brs, 1H).
The crude allyl-2-[D₁] alcohol (3.0 g, 50.8 mmol, 1 equiv) was added to a stirring solution of PBr₃ (2.4 mL, 25.5 mmol, 0.5 equiv) in Et₂O (21 mL) dropwise at 0°C. The resulting solution was stirred at 0°C for 1 h and then carefully quenched by the addition of brine (12 mL). The layers were separated and the combined organic extracts were washed with a saturated solution of NaHCO₃, brine and dried over Na₂SO₄. Excess solvent was removed via careful distillation (45–50°C). The crude allyl-2-[D₁] bromide was obtained as colorless liquid (2.1 g, 32% yield over 2 steps).^{[5 ] 1}H NMR (500 MHz, CDCl₃): δ = 5.31 (s, 1H), 5.14 (s, 1H), 3.94 ppm (s, 2H).
Into an oven-dried round bottom flask were added the crude allyl-2-[D₁] bromide (1.5 mL, 12.5 mmol, 1.0 equiv), aniline (4.5 mL, 37.0 mmol, 3.0 equiv), K₂CO₃ (5.0 g, 37.0 mmol, 3.0 equiv) and DMF (20 mL).^{[6 ]} The flask was equipped with a stopper and the reaction mixture was heated to 70°C overnight. The mixture was allowed to cool to room temperature and was washed with water (20 mL). The aqueous phase was extracted with Et₂O (3 × 20 mL). The combined organic layers were washed with brine, dried with Na₂SO₄ and concentrated in vacuo. Purification by flash chromatography on SiO₂ (10% EtOAc in hexanes) gave compound N-allyl-2-[D₁] aniline (0.7 g, 45% yield). Data: ¹H NMR (500 MHz, CDCl₃): δ = 7.18 (t, J = 7.5 Hz, 2H), 6.72 (t, J = 7.5 Hz, 1H), 6.64 (d, J = 8.0 Hz, 2H), 5.29 (s, 1H), 5.17 (s, 1H), 3.78 ppm (s, 2H); ¹³C NMR (75 Hz, CDCl₃): δ = 148.0, 135.1 (t, J = 23.0 Hz), 129.2, 117.5, 116.1, 112.9, 46.4 ppm; HRMS (ESI): m/z calcd for [M]⁺ C₉H₁₁DN₁: 135.1027, found: 135.1022.
To an oven-dried pressure tube were added N-allyl-2-[D₁] aniline (0.7 g, 5.2 mmol, 1 equiv) and xylenes (13 mL). The solution was cooled to −78°C and BF₃·Et₂O (1.3 mL, 10.4 mmol, 2.0 equiv) was added dropwise. The resulting solution was warmed to room temperature and was heated to 160°C for 4 h.^{[7 (link)]} The reaction mixture was then cooled to room temperature and was placed in an ice–water bath and was quenched with 2M NaOH (6 mL). The organic layer was separated and aqueous layer was extracted with Et₂O (3 × 10 mL). The organics were combined, dried with Na₂SO₄, filtered and concentrated in vacuo. Purification by flash chromatography on SiO₂ (10% EtOAc in hexanes) gave o-allyl-2-[D₁] aniline (0.5 g, 70% yield). ¹H NMR (500 MHz, CDCl₃): δ = 7.05 (t, J = 8.0 Hz, 2H), 6.75 (t, J = 7.5 Hz, 1H), 6.64 (d, J = 8.0 Hz, 1H), 5.12 (s, 1H), 5.10 s, 1H), 3.66 (brs, 2H), 3.30 ppm (s, 2H); HRMS (ESI): m/z calcd for [M+ H]⁺ C₉H₁₁DN₁: 135.1012, found: 135.1009.
The o-allyl-2-[D₁] aniline (0.5 g, 3.7 mmol, 1 equiv) was dissolved in dry CH₂Cl₂ (20 mL) and the solution was treated with pyridine (1.18 mL, 14.9 mmol, 4 equiv) followed by p-toluenesulfonyl chloride (0.85 g, 4.5 mmol, 1.2 equiv). The mixture was stirred at room temperature for 24 h, washed with 1N HCl (15 mL) and extracted with CH₂Cl₂ (3 × 15 mL). The combined organic layers were washed with brine, dried over Na₂SO₄, and concentrated in vacuo. Flash chromatography of the resulting crude compound on SiO₂ (5–10% EtOAc in hexanes) afforded compound [D]-1b as white solid (1.0 g, 96% yield). M.p. 62–65°C; ¹H NMR (500 MHz, CDCl₃): δ = 7.61 (d, J = 8.5 Hz, 2H), 7.41 (d, J = 8.5 Hz, 1H), 7.23 (d, J = 8.5 Hz, 2H), 7.19 (m, 1H), 7.13–7.05 (m, 2H), 6.55 (b. s., 1H), 5.11 (s, 1H), 4.93 (s, 1H), 3.00 (s, 2H), 2.39 ppm (s, 3H); ¹³C NMR (75 Hz, CDCl₃): δ = 143.7, 136.7, 135.2 (t, J = 24 Hz), 134.9, 131.9, 130.4, 129.5, 127.6, 127.0, 126.2, 124.4, 116.9, 36.0, 21.5 ppm; IR (neat): ν̃ = 3266, 3076, 3030, 2967, 2913, 2849, 2243, 1922, 1623, 1596, 1492, 1451, 1401, 1333, 1161, 1089, 1039, 1016, 921, 817, 754, 663 cm⁻¹; HRMS (ESI): m/z calcd for [M]⁺ C₁₆H₁₆DO₂N₁S₁: 288.1037, found: 288.1036.

Paderes M.C., Belding L., Fanovic B., Dudding T., Keister J.B, & Chemler S.R. (2012). Evidence for Alkene cis-Aminocupration, an Aminooxygenation Case Study: Kinetics, EPR Spectroscopy, and DFT Calculations. Chemistry (Weinheim an Der Bergstrasse, Germany), 18(6), 1711-1726.

Publication 2012

Synthesis and Biological Evaluation of S-Allylcysteine Hybrids

Cited 3 times

Chemical synthesisGeneral remarksMicrowave reactions were carried out in a CEM Discover microwave reactor in sealed vessels (monowave, maximum power 300 W, temperature control by IR sensor, and fixed temperature). ¹H and ¹³C NMR spectra were recorded on a Varian instrument operating at 300, 600 and 75, 125 MHz, respectively. The signals of the deuterated solvent (CDCl₃or DMSO-D₆) were used as reference. Chemical shifts (δ) are expressed in ppm with the solvent peak as reference and TMS as an internal standard; coupling constants (J) are given in Hertz (Hz). Carbon atom types (C, CH, CH₂, CH₃) were determined by using the DEPT pulse sequence. The signals were assigned using two-dimensional heteronuclear correlations (COSY, HSQC and HMBC). High resolution mass spectra were recorded using electrospray ionization mass spectrometry (ESI-MS). A QTOF Premier instrument with an orthogonal Z-spray-electrospray interface (Waters, Manchester, UK) was used operating in the W-mode. The drying and cone gas was nitrogen set to flow rates of 300 and 30 L/h, respectively. Methanol sample solutions (ca. 1 × 10⁻⁵ M) were directly introduced into the ESI spectrometer at a flow rate of 10 µL/min. A capillary voltage of 3.5 kV was used in the positive scan mode, and the cone voltage set to Uc = 10 V. For accurate mass measurements, a 2 mg/L standard solution of leucine enkephalin was introduced via the lock spray needle at a cone voltage set to 85 V and a flow rate of 30 μL/min. IR spectra were recorded on a Spectrum RX I FT-IR system (Perkin-Elmer, Waltham, MA, USA) in KBr disks. Optical rotations were measured (Na-D line) at 25°C using a cell with 1dm path length on a Polartronic (Jasco model p-2000) polarimeter. Silica gel 60 (0.063–0.200 mesh, Merck, Whitehouse Station, NJ, USA) was used for column chromatography, and precoated silica gel plates (Merck 60 F254 0.2 mm) were used for thin layer chromatography (TLC). Monitoring of the reaction progress and product purification was carried out by TLC.
Procedure for the synthesis of S-Allylcysteine (2): S-Cysteine hydrochloride (1 g, 6.34 mmol) was added to allyl bromide (1.15 g, 823 µL, 9.51 mmol) in 2M NH₄OH (20 mL). The resulting mixture was stirred at room temperature for 20h. Then, the reaction mixture was concentrated to precipitate the product as a white solid. The solid was filtered, washed with ethanol (3 × 10 mL) and dried under reduced pressure, affording 818 mg (80%) of compound 2. This compound was used in the following step without further purification.
¹H NMR (DMSO-D₆, 300 MHz): δ 2.48 (NH₂), 2.72 (1H, dd, J = 14.6, 8.0 Hz, S-CH₂CHN), 2.87 (1H, dd, J = 14.6, 4.2 Hz, S-CH₂CHN), 3.06 (2H, d, J = 7.3 Hz, S-CH₂CH=CH₂), 3.56 (1H, dd, J = 8.0, 4.2 Hz, -CH-N), 4.29 (-NH₂), 4.98-5.13 (2H, m, S-CH₂CH=CH₂), 5.59-5.75 (2H, m, S-CH₂CH=CH₂); ¹³C NMR (CDCl₃, 75 MHz): δ 31.33 (S-CH₂CHN), 33.93 (S-CH₂CH=CH₂), 53.45 (CH-N), 118.48 (S-CH₂CH=CH₂), 133.77 (S-CH₂CH=CH₂), 171.33 (-C=O)
Procedure for the synthesis of S-Allylcysteine methyl ester (3a): Thionyl chloride (442.6 mg, 3.72 mmol, 270 µL) was added over 5 min. to dry methanol (15 mL) cooled to -10 °C and the resulting solution was stored for a further 5 min. Then, S-allyl cysteine (500 mg, 3.1 mmol) was added and the mixture was stirred for 10 min. The resulting solution was stored at -10 °C for 2h, kept at room temperature for other 24 h, and then poured into ether (100 mL) and refrigerated for 2 h. The product (488 mg, 90%) separated as colorless needles, was removed by
filtration.
M.p. 114-116 °C; [α]²⁵ + 4.778 (C = 0,013, CHCl₃); IR (KBr, cm^-1): ν _max 3366 (N-H), 1736 (C=O), 1238 (C-O-C); ¹H NMR (DMSO-D₆, 300 MHz): δ 2.51 (NH₂), 2.84 (1H, dd, J = 14.7, 5.0 Hz, S-CH₂CHN), 2.93 (1H, dd, J = 14.7, 5.0 Hz, S-CH₂CHN), 3.09 (2H, d, J = 7.3 Hz, S-CH₂CH=CH₂), 3.70 (3H, s, OCH₃), 4.14 (1H, dd, J = 7.1, 5.0 Hz, -CH-N), 5.04-5.15 (2H, m, S-CH₂CH=CH₂), 5.59-5.77 (1H, m, S-CH₂CH=CH₂); ¹³C NMR (CDCl₃, 75 MHz): δ 30.09 (S-CH₂CHN), 34.20 (S-CH₂CH=CH₂), 52.09 (OCH₃), 54.52 (CH-N), 118.86 (S-CH₂CH=CH₂), 133.37 (S-CH₂CH=CH₂), 168.96 (-C=O). EIMS: m/z 176,0732 [M + H]⁺, Calcd for C₇H₁₄NO₂S: 176.0354.
General procedure for the synthesis of S-Allyl cysteine esters (3b-3e): Thionyl chloride (3eq) was added over 5 min. to dry ethyl, propyl, butyl, or pentyl alcohol (15 mL) cooled to -10 °C and the resulting solution was stored for a further 5 min. Then, S-allyl cysteine (500 mg, 3.1 mmol) was added and the resulting mixture was stored at -10 °C for 2 h and the kept at room temperature for a further 24 h. Then the excess of alcohol was removed by distillation. The residue was purified by column chromatography over silica gel eluting with dichloromethane-methanol (95:5 ratio) to obtain S-allyl cysteine ethyl ester, S-allyl cysteine propyl ester, S-allyl cysteine butyl ester and S-allyl cysteine pentyl ester in 60% (352 mg), 71% (447 mg), 621% (418 mg) and 85% (609 mg) yields, respectively. Monitoring the reaction progress and product purification was carried out by TLC.
Ethyl S-prop-2-en-1-ylcysteinate (3b): M.p. 121-123°C; [α]²⁵ + 1.40 (C = 0,62, CHCl₃); IR (KBr, cm^-1): ν _max 3472 (N-H), 1748 (C=O), 1231 (C-O-C); ¹H NMR (CDCl₃, 600 MHz): δ 0.96 (3H, t, J = 7.2 Hz), 2.63 (NH₂), 3.22-3.25 (2H, m, S-CH₂CHN), 3.18-3.22 (2H, m, S-CH₂CH=CH₂), 3.29 (1H, dd, J = 7.5, 5.0 Hz, -CH-N), 4.29 (2H, q, J = 7.0 Hz, OCH₂), 5.15 (1H, d, J = 10 Hz, S-CH₂CH=CH₂), 5.24 (1H, d, J = 18 Hz, S-CH₂CH=CH₂), 5.74-5.85 (1H, m, S-CH₂CH=CH₂); ¹³C NMR (CDCl₃, 125 MHz): δ 14.05 (CH₃), 30.48 (S-CH₂CHN), 35.10 (S-CH₂CH=CH₂), 52.69 (CH-N), 62.94 (OCH₂), 118.51 (S-CH₂CH=CH₂), 133.37 (S-CH₂CH=CH₂), 167.95 (-C=O). EIMS: m/z 190,0879 [M + H]⁺, Calcd for C₈H₁₆NO₂S: 190.0356.
Propyl S-prop-2-en-1-ylcysteinate (3c): M.p. 115-117 °C; [α]²⁵ + 3.750 (C = 0,015, CHCl₃); IR (KBr, cm^-1): ν _max 3375 (N-H), 1736 (C=O), 1182 (C-O-C); ¹H NMR (CDCl₃, 300 MHz): δ 0.91 (3H, t, J = 7.5 Hz), 1.53-1.72 (2H, m), 1.98 (NH₂), 2.83 (1H, dd, J = 13.5, 5.0 Hz, S-CH₂CHN), 2.65 (1H, dd, J = 13.5, 5.0 Hz, S-CH₂CHN), 3.11 (2H, d, J = 7.0 Hz, S-CH₂CH=CH₂), 3.58 (1H, dd, J = 7.4, 5.0 Hz, -CH-N), 4.05 (2H, t, J = 6.7 Hz, OCH₂), 5.07-5.16 (2H, m, S-CH₂CH=CH₂), 5.64-5.82 (1H, m, S-CH₂CH=CH₂); ¹³C NMR (CDCl₃, 75 MHz): δ 10.41 (CH₃), 21.97 (CH₂), 35.14 (S-CH₂CHN), 35.82 (S-CH₂CH=CH₂), 54.11 (CH-N), 66.82 (OCH₂), 117.61 (S-CH₂CH=CH₂), 134.01 (S-CH₂CH=CH₂), 174.15 (-C=O). EIMS: m/z 204,1036 [M + H]⁺, Calcd for C₉H₁₈NO₂S: 204.0603.
Butyl S-prop-2-en-1-ylcysteinate (3d): M.p. 101-103°C; [α]²⁵ + 3.40 (C = 0,57, CHCl₃); IR (KBr, cm^-1): ν _max 3396 (N-H), 1750 (C=O), 1233 (C-O-C); ¹H NMR (CDCl₃, 600 MHz): δ 0.93 (3H, t, J = 7.5 Hz), 1.34-1.43 (2H, m), 1.62-1.70 (2H, m), 2.62 (NH₂), 3.19 (2H, d, J = 6.8 Hz, S-CH₂CH=CH₂), 3.23 (1H, dd, J = 13.9, 7.0 Hz, S-CH₂CHN), 3.29 (1H, dd, J = 13.9, 7.0 Hz, S-CH₂CHN), 4.17-4.28 (1H, m, -CH-N), 4.38 (2H, t, J = 6.5 Hz, OCH₂), 5.14 (1H, d, J = 10 Hz, S-CH₂CH=CH₂), 5.24 (1H, d, J = 17 Hz, S-CH₂CH=CH₂), 5.74-5.83 (1H, m, S-CH₂CH=CH₂); ¹³C NMR (CDCl₃, 125 MHz): δ 13.66 (CH₃), 19.02 (2CH₂), 30.53 (S-CH₂CHN), 35.11 (S-CH₂CH=CH₂), 52.67 (CH-N), 66.75 (OCH₂), 118.49 (S-CH₂CH=CH₂), 133.38 (S-CH₂CH=CH₂), 168.08 (-C=O). EIMS: m/z 218,1206 [M + H]⁺, Calcd for C₁₀H₂₀NO₂S: 218.0457.
Pentyl S-prop-2-en-1-ylcysteinate (3e): M.p. 98-100°C; [α]²⁵ + 1.558 (C = 0,018, CHCl₃); IR (KBr, cm^-1): ν _max 3448 (N-H), 1747 (C=O), 1234 (C-O-C); ¹H NMR (CDCl₃, 600 MHz): δ 0.93 (3H, t, J = 7.0 Hz), 1.31-1.42 (4H, m), 1.60-1.74 (2H, m), 1.82 (NH₂), 2.71 (1H, dd, J = 13.5, 5.3 Hz, S-CH₂CHN), 2.90 (1H, dd, J = 13.5, 5.3 Hz, S-CH₂CHN), 3.18 (2H, d, J = 7.17 Hz, S-CH₂CH=CH₂), 3.60-3.69 (1H, m, -CH-N), 4.16 (2H, t, J = 6.7 Hz,-OCH₂), 5.11-5.20 (2H, m, S-CH₂CH=CH₂), 5.72-5.89 (1H, m, S-CH₂CH=CH₂); ¹³C NMR (CDCl₃, 125 MHz): δ 13.70 (CH₃), 22.03 (CH₂), 27.78 (CH₂), 28.01 (CH₂), 34.83 (S-CH₂CHN), 35.53 (S-CH₂CH=CH₂), 54.84 (CH-N), 65.04 (OCH₂), 117.23 (S-CH₂CH=CH₂), 134.82 (S-CH₂CH=CH₂), 173.91 (-C=O); EIMS: m/z 232.1368 [M + H]⁺, Calcd for C₁₁H₂₂NO₂S: 232.1371.
General procedure for condensation using HBTU A solution of 3,4-diacetoxycaffeic acid (5) or 3,4-disilylated caffeic acid (7) (1 mmol) and triethylamine (4 mmol) in THF (10 mL) was stirred for 15 min. Then, HBTU (1.5 mmol) was added and the resulting mixture was stirred for 10 min. Then, S-allyl cysteine ester (3a-3e) (1.2 mmol) was added and the resulting mixture was allowed to stir for 15 h. The solvent was removed under reduced pressure, and the residue was chromatographed on silica gel. Elution with hexane-ethyl acetate (1:1 ratio) afforded compounds 6a-6e in yields ranging 30-40% [6a, 35% (148 mg); 6b, 39% (170 mg); 6c, 34% (153 mg); 6d, 33% (153 mg) and 6e, 40% (191 mg)] or 8a-8e in yields ranging 50-60% [8a, 50% (283 mg); 8b, 50% (578 mg); 8c, 52% (309 mg); 8d, 50% (304 mg) and 8e, 60% (373 mg)].
Methyl N-{(2E)-3-[3,4-bis(acetyloxy)phenyl]prop-2-enoyl}-S-prop-2-en-1-ylcysteinate (6a): M.p. 107-109°C; [α]²⁵ + 5.292 (C = 0,019, CHCl₃); IR (KBr, cm^-1): ν _max 3394 (N-H), 1770, 1743 and 1662 (C=O), 1259 (C-O-C), 1205 ((C=O)-O); ¹H NMR (CDCl₃, 300 MHz): δ 2.30 (3H, s, ((CH₃-C=O)-O), 2.31 (3H, s, (CH₃-C=O)-O), 2.95 (1H, dd, J = 14.0, 5.0 Hz, S-CH₂CHN), 3.04 (1H, dd, J = 14.0, 5.0 Hz, S-CH₂CHN), 3.13 (2H, d, J = 7.0 Hz, S-CH₂CH=CH₂), 3.79 (3H, s, OCH₃), 4.89-4.98 (1H, m, -CH-N), 5.07-5.17 (2H, m, S-CH₂CH=CH₂), 5.66-5.82 (1H, m, S-CH₂CH=CH₂), 6.40 (1H, d, J = 15.6 Hz, –CO–CH=), 6.47 (1H, d, J = 7.5 Hz, -CH-NH-C=O), 7.20 (1H, d, J = 8.3 Hz, Ar-H), 7.39 (1H, d, J = 1.8 Hz, Ar-H), 7.35 (1H, dd, J = 8.3, 1.8 Hz, Ar-H), 7.59 (1H, d, J = 15.6 Hz, Ar-CH=C); ¹³C NMR (CDCl₃, 75 MHz): δ 20.76 ((CH₃-C=O)-O), 20.79 ((CH₃-C=O)-O), 32.76 (S-CH₂CHN), 35.33 (S-CH₂CH=CH₂), 52.05 (CH-N), 52.88 (OCH₃), 118.19 (C=C-CO-), 121.08 (S-CH₂CH=CH₂), 122.61 (Ar), 123.99 (Ar), 126.45 (Ar), 129.16 (Ar), 133.64 (Ar), 133.54 (S-CH₂CH=CH₂), 140.37 (Ar-C=C), 142.50 (Ar-O), 143.29 (Ar-O), 165.09 (-NH-C=O), 168.21 ((CH₃-C=O)-O), 168.25 ((CH₃-C=O)-O), 171.44 ((NCH-C=O)-O); EIMS: m/z 444.1090 [M + Na]⁺, Calcd for C₂₀H₂₄NO₇S: 444.1093
Ethyl N-{(2E)-3-[3,4-bis(acetyloxy)phenyl]prop-2-enoyl}-S-prop-2-en-1-ylcysteinate (6b): M.p. 96-99°C; [α]²⁵ + 13.60 (C = 0,835, CHCl₃); IR (KBr, cm^-1): ν _max 3317 (N-H), 1774, 1734 and 1655 (C=O), 1265 (C-O-C), 1209 ((C=O)-O); ¹H NMR (CDCl₃, 600 MHz): δ 1.31 (3H, t, J = 7.1 Hz), 2.30 (3H, s, ((CH₃-C=O)-O), 2.31 (3H, s, (CH₃-C=O)-O), 2.96 (1H, dd, J = 14.0, 5.4 Hz, S-CH₂CHN), 3.05 (1H, dd, J = 14.0, 5.4 Hz, S-CH₂CHN), 3.14 (2H, d, J = 7.02 Hz, S-CH₂CH=CH₂), 4.26 (2H, q, J = 7.0 Hz, OCH₂), 4.90-4.94 (1H, m, -CH-N), 5.10-5.15 (2H, m, S-CH₂CH=CH₂), 5.71-5.80 (1H, m, S-CH₂CH=CH₂), 6.41 (1H, d, J = 15.7 Hz, –CO–CH=), 6.51 (1H, d, J = 7.5 Hz, -CH-NH-C=O), 7.21 (1H, d, J = 8.4 Hz, Ar-H), 7.34 (1H, d, J = 2.0 Hz, Ar-H), 7.37 (1H, dd, J = 8.4, 2.0 Hz, Ar-H), 7.58 (1H, d, J = 15.7 Hz, Ar-CH=C); ¹³C NMR (CDCl₃, 125 MHz): δ 14.28 (CH₃), 20.76 ((CH₃-C=O)-O), 20.79 ((CH₃-C=O)-O), 32.89 (S-CH₂CHN), 35.39 (S-CH₂CH=CH₂), 52.16 (CH-N), 62.11 (OCH₂), 118.03 (S-CH₂CH=CH₂), 118.13 (C=C-CO-), 121.16 (Ar), 122.61 (Ar), 123.99 (Ar), 126.44 (Ar), 133.73 (S-CH₂CH=CH₂), 140.30 (Ar-C=C), 142.50 (Ar-O), 143.29 (Ar-O), 165.08 (-NH-C=O), 168.20 ((CH₃-C=O)-O), 168.26 ((CH₃-C=O)-O), 170.94 ((NCH-C=O)-O); EIMS: m/z 436.1430 [M + H]⁺, Calcd for C₂₁H₂₆NO₇S: 436.1431.
Propyl N-{(2E)-3-[3,4-bis(acetyloxy)phenyl]prop-2-enoyl}-S-prop-2-en-1-ylcysteinate (6c): M.p. 80-82°C; [α]²⁵ + 1.442 (C = 0,011, CHCl₃); IR (KBr, cm^-1): ν _max 3315 (N-H), 1766, 1735 and 1658 (C=O), 1209 (C-O-C), 1184 ((C=O)-O); ¹H NMR (CDCl₃, 300 MHz): δ 0.96 (3H, t, J = 7.5 Hz), 1.62-1.77 (2H, m), 2.29 (3H, s, ((CH₃-C=O)-O), 2.30 (3H, s, (CH₃-C=O)-O), 2.94 (1H, dd, J = 13.9, 5.3 Hz, S-CH₂CHN), 3.04 (1H, dd, J = 13.9, 4.9 Hz, S-CH₂CHN), 3.13 (2H, d, J = 7.20 Hz, S-CH₂CH=CH₂), 4.14 (2H, t, J = 6.7 Hz, OCH₂), 4.87-4.97 (1H, m, -CH-N), 5.05-5.18 (2H, m, S-CH₂CH=CH₂), 5.64-5.82 (1H, m, S-CH₂CH=CH₂), 6.41 (1H, d, J = 15.6 Hz, –CO–CH=), 6.52 (1H, d, J = 7.5 Hz, -CH-NH-C=O), 7.20 (1H, d, J = 8.3 Hz, Ar-H), 7.24 (1H, d, J = 1.6 Hz, Ar-H), 7.34 (1H, dd, J = 8.3, 1.6 Hz, Ar-H), 7.58 (1H, d, J = 15.6 Hz, Ar-CH=C); ¹³C NMR (CDCl₃, 75 MHz): δ 10.46 (CH₃), 20.77 ((CH₃-C=O)-O), 22.00 ((CH₃-C=O)-O), 32.86 (S-CH₂CHN), 35.37 (S-CH₂CH=CH₂), 52.16 (CH-N), 67.61 (OCH₂), 118.12 (S-CH₂CH=CH₂), 121.16 (=C-CO-), 122.58 (Ar), 123.97 (Ar), 126.44 (Ar), 129.14 (Ar), 133.66 (S-CH₂CH=CH₂), 140.25 (Ar-C=), 142.48 (Ar-O), 143.25 (Ar-O), 165.09 (N-C=O), 168.19 ((CH₃-C=O)-O), 168.24 ((CH₃-C=O)-O), 171.62 ((NCH-C=O)-O); EIMS: m/z 472.1401 [M + Na]⁺, Calcd for C₂₂H₂₇NO₇S-Na: 472.1406.
Butyl N-{(2E)-3-[3,4-bis(acetyloxy)phenyl]prop-2-enoyl}-S-prop-2-en-1-ylcysteinate (6d): M.p. 94-97°C; [α]²⁵ + 8.30 (C = 0,65, CHCl₃); IR (KBr, cm^-1): ν _max 3309 (N-H), 1774, 1742 and 1662 (C=O), 1265 (C-O-C), 1209 ((C=O)-O); ¹H NMR (CDCl₃, 600 MHz): δ 0.95 (3H, t, J = 7.2 Hz), 1.36-1.44 (2H, m), 1.61-1.72 (2H, m), 2.30 (3H, s, ((CH₃-C=O)-O), 2.31 (3H, s, ((CH₃-C=O)-O), 2.95 (1H, dd, J = 13.8, 5.4 Hz, S-CH₂CHN), 3.05 (1H, dd, J = 13.9, 5.4 Hz, S-CH₂CHN), 3.10-3.16 (2H, m, S-CH₂CH=CH₂), 4.19 (2H, q, J = 6.9 Hz, OCH₂), 4.90-4.96 (1H, m, -CH-N), 5.08-5.15 (2H, m, S-CH₂CH=CH₂), 5.70-5.79 (1H, m, S-CH₂CH=CH₂), 6.41 (1H, d, J = 15.6 Hz, –CO–CH=), 6.50 (1H, d, J = 7.2 Hz, -CH-NH-C=O), 7.21 (1H, d, J = 8.3 Hz, Ar-H), 7.35 (1H, s, Ar-H), 7.38 (1H, d, J = 8.3, Ar-H), 7.59 (1H, d, J = 15.6 Hz, Ar-CH=C); ¹³C NMR (CDCl₃, 125 MHz): δ 13.77 (CH₃), 19.19 (CH₂), 20.70 ((CH₃-C=O)-O), 20.78 ((CH₃-C=O)-O), 23.18 (CH₂), 32.97 (S-CH₂CHN), 35.41 (S-CH₂CH=CH₂), 52.20 (CH-N), 65.94 (OCH₂), 118.01 (S-CH₂CH=CH₂), 118.11 (=C-CO-), 121.17 (Ar), 122.60 (Ar), 123.98 (Ar), 126.43 (Ar), 133.73 (S-CH₂CH=CH₂), 140.29 (Ar-C=), 142.51 (Ar-O), 143.29 (Ar-O), 165.09 (N-C=O), 168.18 ((CH₃-C=O)-O), 168.23 ((CH₃-C=O)-O), 171.02 ((NCH-C=O)-O); EIMS: m/z 464.1743 [M + H]⁺, Calcd for C₂₃H₂₉NO₇S: 464.1745.
Pentyl N-{(2E)-3-[3,4-bis(acetyloxy)phenyl]prop-2-enoyl}-S-prop-2-en-1-ylcysteinate (6e): M.p. 101-103°C; [α]²⁵ + 3.087 (C = 0,0119, CHCl₃); IR (KBr, cm^-1): ν _max 3317 (N-H), 1768, 1743 and 1656 (C=O), 1219 (C-O-C), 1184 ((C=O)-O); ¹H NMR (CDCl₃, 300 MHz): δ 0.90 (3H, t, J = 7.1 Hz), 1.28-1.39 (4H, m), 1.60-1.74 (2H, m), 2.29 (3H, s, ((CH₃-C=O)-O), 2.30 (3H, s, ((CH₃-C=O)-O), 2.94 (1H, dd, J = 13.9, 5.3 Hz, S-CH₂CHN), 3.05 (1H, dd, J = 13.9, 4.8 Hz, S-CH₂CHN), 3.13 (2H, d, J = 7.3 Hz, S-CH₂CH=CH₂), 4.18 (2H, t, J = 6.8 Hz, OCH₂), 4.87-4.96 (1H, m, -CH-N), 5.06-5.10 (2H, m, S-CH₂CH=CH₂), 5.66-5.82 (1H, m, S-CH₂CH=CH₂), 6.40 (1H, d, J = 15.6 Hz, –CO–CH=), 6.48 (1H, d, J = 7.4 Hz, -CH-NH-C=O), 7.20 (1H, d, J = 8.4 Hz, Ar-H), 7.34 (1H, d, J = 1.8 Hz, Ar-H), 7.38 (1H, dd, J = 8.4, 1.8 Hz, Ar-H), 7.58 (1H, d, J = 15.6 Hz, Ar-CH=C); ¹³C NMR (CDCl₃, 75 MHz): δ 14.07 (CH₃), 20.77 ((CH₃-C=O)-O), 20.80 ((CH₃-C=O)-O), 22.37 (CH₂), 28.07 (CH₂), 28.29 (CH₂), 32.89 (S-CH₂CHN), 35.41 (S-CH₂CH=CH₂), 52.18 (CH-N), 66.23 (OCH₂), 118.13 (S-CH₂CH=CH₂), 119.0 (=C-CO-), 121.15 (Ar), 122.60 (Ar), 123.99 (Ar), 126.44 (Ar), 133.67 (S-CH₂CH=CH₂), 140.29 (Ar-C=C), 142.50 (Ar-O), 143.28 (Ar-O), 165.07 (N-C=O), 168.20 ((CH₃-C=O)-O), 168.25 ((CH₃-C=O)-O), 171.02 ((NCH-C=O)-O); EIMS: m/z 500.1719 [M + Na]⁺, Calcd for C₂₄H₃₁NO₇S-Na: 500.1719.
Methyl N-[(2E)-3-(3,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)prop-2-enoyl]-S-prop-2-en-1-yl-L-cysteinate(8a): colorless oil; [α]²⁵ + 2.50 (C = 0,50, CHCl₃); IR (KBr, cm^-1): ν _max 3309 (N-H), 1742 and 1666 (C=O), 1424 (Si-C), 1249 (C-O-C), 1202 ((C=O)-O), 1106 (Si-O); ¹H NMR (CDCl₃, 600 MHz): δ 0.21 (12H, s, -Si-CH₃), 0.98 (9H, s, -C-(CH₃)₃), 1.0 (9H, s, -C-(CH₃)₃), 2.96 (1H, dd, J = 14.0, 5.0 Hz, S-CH₂CHN), 3.04 (1H, dd, J = 14.0, 5.0 Hz, S-CH₂CHN), 3.14 (2H, t_app, J = 7.5 Hz, S-CH₂CH=CH₂), 3.80 (3H, s, OCH₃), 4.93-4.98 (1H, m, -CH-N), 5.08-5.16 (2H, m, S-CH₂CH=CH₂), 5.70-5.80 (1H, m, S-CH₂CH=CH₂), 6.25 (1H, d, J = 15.5 Hz, –CO–CH=C), 6.35 (1H, d, J = 7.2 Hz, -CH-NH-C=O), 6.81 (1H, d, J = 8.0 Hz, Ar-H), 6.98-7.02 (2H, m, Ar-H), 7.52 (1H, d, J = 15.5 Hz, Ar-CH=C); ¹³C NMR (CDCl₃, 125 MHz): δ -3.92 (-Si-CH₃), -3.44 (-Si-CH₃), 18.60 (-Si-C-(CH₃)₃), 18.64 (-Si-C-(CH₃)₃), 26.03 (-C-(CH₃)₃), 26.07 (-C-(CH₃)₃), 32.96 (S-CH₂CHN), 35.40 (S-CH₂CH=CH₂), 52.04 (CH-N), 52.85 (OCH₂), 117.58 (Ar), 118.07 (S-CH₂CH=CH₂), 118.16 (Ar), 120.88 (C=C-CO-), 121.29 (Ar), 122.01 (Ar), 133.73 (S-CH₂CH=CH₂), 142.07 (Ar-C=C), 147.27 (Ar-O), 149.23 (Ar-O), 165.90 (-NH-C=O), 171.67 (CH-C=O)-O).
EIMS: m/z 566, 2751 [M + H]⁺, Calcd for C₂₈H₄₈NO₅SSi₂: 566.1994.
Ethyl N-[(2E)-3-(3,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)prop-2-enoyl]-S-prop-2-en-1-yl-L-cysteinate(8b): colorless oil; [α]²⁵ + 2.30 (C = 0,585, CHCl₃); IR (KBr, cm^-1): ν _max 3293 (N-H), 1750 and 1662 (C=O), Si-C (1416), 1257 (C-O-C), 1209 ((C=O)-O), 1209 (Si-O); ¹H NMR (CDCl₃, 600 MHz): δ 0.21 (12H, s, -Si-CH₃), 0.98 (9H, s, -C-(CH₃)₃), 1.0 (9H, s, -C-(CH₃)₃), 1.31 (3H, t, J = 7.2 Hz), 2.96 (1H, dd, J = 13.94, 5.2 Hz, S-CH₂CHN), 3.05 (1H, dd, J = 13.94, 5.2 Hz, S-CH₂CHN), 3.14 (2H, t_app, J = 6.8 Hz, S-CH₂CH=CH₂), 4.26 (2H, q, J = 7.1 Hz, OCH₂), 4.91-4.96 (1H, m, -CH-N), 5.09-5.16 (2H, m, S-CH₂CH=CH₂), 5.70-5.79 (1H, m, S-CH₂CH=CH₂), 6.26 (1H, d, J = 15.6 Hz, –CO–CH=C), 6.36 (1H, d, J = 7.5 Hz, -CH-NH-C=O), 6.81 (1H, d, J = 8.0 Hz, Ar-H), 6.98-7.02 (2H, m, Ar-H), 7.52 (1H, d, J = 15.6 Hz, Ar-CH=C); ¹³C NMR (CDCl₃, 125 MHz): δ -3.92 (-Si-CH₃), -3.43 (-Si-CH₃), 14.31 (-Si-C-(CH₃)₃), 18.60 (-Si-C-(CH₃)₃), 18.64 (-Si-C-(CH₃)₃), 26.03 (-C-(CH₃)₃), 26.07 (-C-(CH₃)₃), 33.03 (S-CH₂CHN), 35.45 (S-CH₂CH=CH₂), 52.15 (CH-N), 62.06 (OCH₂), 117.54 (Ar), 118.09 (S-CH₂CH=CH₂), 120.62 (Ar), 121.29 ((C=C-CO-), 121.99 (Ar), 128.32 (Ar), 133.77 (S-CH₂CH=CH₂), 138.59 (Ar-C=C), 147.27 (Ar-O), 149.60 (Ar-O), 165.88 (-NH-C=O), 171.17 (CH-C=O)-O). EIMS: m/z 580,2944 [M + H]⁺, Calcd for C₂₉H₅₀NO₅SSi₂: 580.2170.
Propyl N-[(2E)-3-(3,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)prop-2-enoyl]-S-prop-2-en-1-yl-L-cysteinate(8c): colorless oil; [α]²⁵ + 1.70 (C = 0,665, CHCl₃); IR (KBr, cm^-1): ν _max 3277 (N-H), 1742 and 1662 (C=O), 1416 (Si-C), 1257 (C-O-C), 1209 ((C=O)-O), 1122 (Si-O); ¹H NMR (CDCl₃, 600 MHz): δ 0.21 (12H, s, -Si-CH₃), 0.98 (3H, t, J = 7.0 Hz), 0.99 (9H, s, -C-(CH₃)₃), 1.0 (9H, s, -C-(CH₃)₃), 1.67-1.74 (2H, m), 2.95 (1H, dd, J = 14.0, 5.3 Hz, S-CH₂CHN), 3.05 (1H, dd, J = 14.0, 5.3 Hz, S-CH₂CHN), 3.15 (2H, t_app, J = 6.8 Hz, S-CH₂CH=CH₂), 4.15 (2H, t, J = 6.6 Hz, OCH₂), 4.92-4.97 (1H, m, -CH-N), 5.10-5.15 (2H, m, S-CH₂CH=CH₂), 5.71-5.79 (1H, m, S-CH₂CH=CH₂), 6.25 (1H, d, J = 15.5 Hz, –CO–CH=C), 6.37 (1H, d, J = 7.6 Hz, -CH-NH-C=O), 6.81 (1H, d, J = 8.0 Hz, Ar-H), 6.98-7.02 (2H, m, Ar-H), 7.52 (1H, d, J = 15.5 Hz, Ar-CH=C); ¹³C NMR (CDCl₃, 125 MHz): δ -4.06 (-Si-CH₃), -3.92 (-Si-CH₃), 10.50 (-Si-C-(CH₃)₃), 18.60 (-Si-C-(CH₃)₃), 18.64 (-Si-C-(CH₃)₃), 22.05 (CH₂), 26.03 (-C-(CH₃)₃), 26.06 (-C-(CH₃)₃), 33.09 (S-CH₂CHN), 35.46 (S-CH₂CH=CH₂), 52.16 (CH-N), 67.60 (OCH₂), 117.17 (Ar), 118.10 (S-CH₂CH=CH₂), 120.62 (Ar), 121.29 ((C=C-CO-), 121.98 (Ar), 128.32 (Ar), 133.76 (S-CH₂CH=CH₂), 142.05 (Ar-C=C), 147.26 (Ar-O), 149.19 (Ar-O), 165.90 (-NH-C=O), 171.27 (CH-C=O)-O). EIMS: m/z 594, 3136 [M + H]⁺, Calcd for C₃₀H₅₂NO₅SSi₂: 594.2331.
Butyl N-[(2E)-3-(3,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)prop-2-enoyl]-S-prop-2-en-1-yl-L-cysteinate(8d): colorless oil; [α]²⁵ + 2.50 (C = 0,64, CHCl₃); IR (KBr, cm^-1): ν _max 3285 (N-H), 1742 and 1655 (C=O), 1416 (Si-C), 1265 (C-O-C), 1209 ((C=O)-O), 1122 (Si-O); ¹H NMR (CDCl₃, 600 MHz): δ 0.21 (12H, s, -Si-CH₃), 0.95 (3H, t, J = 7.1 Hz), 0.98 (9H, s, -C-(CH₃)₃), 1.0 (9H, s, -C-(CH₃)₃), 1.34-1.45 (2H, m), 1.61-1.71 (2H, m), 2.95 (1H, dd, J = 13.90, 5.2 Hz, S-CH₂CHN), 3.05 (1H, dd, J = 13.90, 5.4 Hz, S-CH₂CHN), 3.05 (2H, t_app, J = 6.7 Hz, S-CH₂CH=CH₂), 4.20 (2H, t, J = 6.7 Hz, OCH₂), 4.91-4.96 (1H, m, -CH-N), 5.08-5.016 (2H, m, S-CH₂CH=CH₂), 5.70-5.79 (1H, m, S-CH₂CH=CH₂), 6.25 (1H, d, J = 15.5 Hz, –CO–CH=C), 6.36 (1H, d, J = 7.6 Hz, -CH-NH-C=O), 6.81 (1H, d, J = 8.0 Hz, Ar-H), 6.97-7.02 (2H, m, Ar-H), 7.52 (1H, d, J = 15.5 Hz, Ar-CH=C); ¹³C NMR (CDCl₃, 125 MHz): δ -4.02 (-Si-CH₃), -3.92 (-Si-CH₃), 13.80 (-Si-C-(CH₃)₃), 18.60 (-Si-C-(CH₃)₃), 18.64 (-Si-C-(CH₃)₃), 19.22 (CH₂), 26.03 (-C-(CH₃)₃), 26.07 (-C-(CH₃)₃), 30.65 (CH₂), 33.10 (S-CH₂CHN), 35.47 (S-CH₂CH=CH₂), 52.17 (CH-N), 65.90 (OCH₂), 117.68 (Ar), 118.09 (S-CH₂CH=CH₂), 120.62 (Ar), 121.99 ((C=C-CO-), 123.62 (Ar), 128.32 (Ar), 133.77 (S-CH₂CH=CH₂), 142.05 (Ar-C=C), 147.27 (Ar-O), 149.20 (Ar-O), 165.90 (-NH-C=O), 171.26 (CH-C=O)-O). EIMS: m/z 609.3315 [M + H]⁺, Calcd for C₃₁H₅₄NO₅SSi₂: 609.3293.
Pentyl N-[(2E)-3-(3,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)prop-2-enoyl]-S-prop-2-en-1-yl-L-cysteinate(8f): colorless oil; [α]²⁵ + 2.80 (C = 0,925, CHCl₃); IR (KBr, cm^-1): ν _max 3277 (N-H), 1750 and 1662 (C=O), 1416 (Si-C), 1249 (C-O-C), 1209 ((C=O)-O), 1122 (Si-O); ¹H NMR (CDCl₃, 600 MHz): δ 0.21 (12H, s, -Si-CH₃), 0.91 (3H, t, J = 7.0 Hz), 0.98 (9H, s, -C-(CH₃)₃), 1.0 (9H, s, -C-(CH₃)₃), 1.29-1.39 (4H, m), 1.60-1.73 (2H, m), 2.95 (1H, dd, J = 13.90, 5.2 Hz, S-CH₂CHN), 3.05 (1H, dd, J = 13.90, 5.4 Hz, S-CH₂CHN), 3.15 (2H, t_app, J = 6.9 Hz, S-CH₂CH=CH₂), 4.18 (2H, t, J = 6.6 Hz, OCH₂), 4.91-4.97 (1H, m, -CH-N), 5.10-5.16 (2H, m, S-CH₂CH=CH₂), 5.70-5.80 (1H, m, S-CH₂CH=CH₂), 6.24 (1H, d, J = 15.7 Hz, –CO–CH=C), 6.37 (1H, d, J = 7.5 Hz, -CH-NH-C=O), 6.81 (1H, d, J = 8.0 Hz, Ar-H), 6.98-7.02 (2H, m, Ar-H), 7.52 (1H, d, J = 15.7 Hz, Ar-CH=C); ¹³C NMR (CDCl₃, 125 MHz): δ -4.02 (-Si-CH₃), -3.92 (-Si-CH₃), 14.09 (-Si-C-(CH₃)₃), 18.60 (-Si-C-(CH₃)₃), 18.64 (-Si-C-(CH₃)₃), 22.40 (CH₂), 26.03 (-C-(CH₃)₃), 26.06 (-C-(CH₃)₃), 28.12 (CH₂), 28.30 (CH₂), 33.09 (S-CH₂CHN), 35.46 (S-CH₂CH=CH₂), 52.17 (CH-N), 66.18 (OCH₂), 117.68 (Ar), 118.08 (S-CH₂CH=CH₂), 120.61 (Ar), 121.29 ((C=C-CO-), 121.98 (Ar), 128.32 (Ar), 133.77 (S-CH₂CH=CH₂), 142.04 (Ar-C=C), 147.26 (Ar-O), 149.19 (Ar-O), 165.88 (-NH-C=O), 171.25 (CH-C=O)-O). EIMS: m/z 623,3478 [M + H]⁺, Calcd for C₃₂H₅₆NO₅SSi₂: 623.3431.
Procedure for desprotection of compounds 8a-8eTo a solution of compound 8 (1 mmol) in THF-H₂O (1:1) (10 mL) was added KF (4 mmol) and the mixture was stirred for 12 h. Then an aqueous saturated solution of NH₄Cl was added and the mixture was extracted with dichloromethane (3 × 10 mL). The combined organic phases were dried over anhydrous MgSO₄ and the solvent was evaporated under reduced pressure to afford hybrids 9a-9e in yields ranging 50%-96% [9a, 69% (233 mg); 9b, 50% (176 mg); 9c, 67% (246 mg); 9d, 86% (326 mg) and 9e, 96% (378
mg)].
Methyl N-[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoyl]-S-2-propen-1-yl-L-cysteinate (9a): M.p. 101-103°C; [α]²⁵ + 10.10 (C = 0,60, CHCl₃); IR (KBr, cm^-1): ν _max 3460 (OH), 3222 (N-H), 1750 and 1665 (C=O), 1265 (C-O-C), 1209 ((C=O)-O); ¹H NMR (CDCl₃, 600 MHz): δ 2.93 (1H, dd, J = 14.0, 5.0 Hz, S-CH₂CHN), 3.02 (1H, dd, J = 14.10, 5.0 Hz, S-CH₂CHN), 3.12 (2H, t_app, J = 7.0 Hz, S-CH₂CH=CH₂), 3.78 (s, OCH₃), 4.86-4.96 (1H, m, -CH-N), 5.04-5.16 (2H, m, S-CH₂CH=CH₂), 5.67-5.78 (1H, m, S-CH₂CH=CH₂), 6.26 (1H, d, J = 15.7 Hz, –CO–CH=C), 6.78 (d, J = 7.2 Hz, -CH-NH-C=O), 6.81 (1H, d, J = 8.0 Hz, Ar), 6.86 (1H, dd, J = 8.0, 1.5 Hz, Ar), 7.02 (1H, d, J = 1.5 Hz, Ar), 7.47 (1H, d, J = 15.6 Hz, Ar-CH=C); ¹³C NMR (CDCl₃, 125 MHz): δ 32.65 (S-CH₂CHN), 35.26 (S-CH₂CH=CH₂), 52.22 (CH-N), 68.13 (OCH₃), 114.55 (Ar), 115.54 (Ar), 116.62 ((C=C-CO-), 118.27 (S-CH₂CH=CH₂), 121.98 (Ar), 127.16 (Ar), 133.59 (S-CH₂CH=CH₂), 143.13 (Ar-C=C), 144.39 (Ar-O), 146.96 (Ar-O), 167.18 (-NH-C=O), 171.83 (CH-C=O)-O); EIMS: m/z 338.1062 [M + H]⁺, Calcd for C₁₆H₂₀NO₅S: 338.1061.
Ethyl N-[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoyl]-S-2-propen-1-yl-L-cysteinate (9b): M.p. 110-112°C; [α]²⁵ + 12.70 (C = 0,54, CHCl₃); IR (KBr, cm^-1): ν _max 3467 (OH), 3213 (N-H), 1742 and 1662 (C=O), 1265 (C-O-C), 1202 ((C=O)-O); ¹H NMR (CDCl₃, 600 MHz): δ 1.29 (3H, t, J = 7.0 Hz), 2.93 (1H, dd, J = 14.10, 5.2 Hz, S-CH₂CHN), 3.03 (1H, dd, J = 14.10, 5.2 Hz, S-CH₂CHN), 3.13 (2H, t_app, J = 6.2 Hz, S-CH₂CH=CH₂), 4.24 (2H, t, J = 7.0 Hz, OCH₂), 4.86-4.93 (1H, m, -CH-N), 5.07-5.13 (2H, m, S-CH₂CH=CH₂), 5.67-5.77 (1H, m, S-CH₂CH=CH₂), 6.26 (1H, d, J = 15.6 Hz, –CO–CH=C), 6.77-6.87 (3H, m, Ar-H, -CH-NH-C=O), 7.01 (1H, s, Ar-H), 7.46 (1H, d, J = 15.6 Hz, Ar-CH=C); ¹³C NMR (CDCl₃, 125 MHz): δ 14.24 (CH₃), 32.66 (S-CH₂CHN), 35.28 (S-CH₂CH=CH₂), 52.34 (CH-N), 62.41 (OCH₂), 114.76 (Ar), 115.57 (Ar), 116.57 ((C=C-CO-), 118.25 (S-CH₂CH=CH₂), 121.95 (Ar), 127.12 (Ar), 133.59 (S-CH₂CH=CH₂), 143.18 (Ar-C=C), 144.36 (Ar-O), 147.0 (Ar-O), 167.31 (-NH-C=O), 171.40 (CH-C=O)-O); EIMS: m/z 352.1219 [M + H]⁺, Calcd for C₁₇H₂₂NO₅S: 352.1215.
Propyl N-[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoyl]-S-2-propen-1-yl-L-cysteinate (9c): M.p. 129-131°C; [α]²⁵ + 12.70 (C = 0,61, CHCl₃); IR (KBr, cm^-1): ν _max 3467 (OH), 3206 (N-H), 1750 and 1662 (C=O), 1257 (C-O-C), 1209 ((C=O)-O); ¹H NMR (CDCl₃, 600 MHz): δ 0.95 (3H, t, J = 7.0 Hz), 1.63-1.73 (CH₂, m), 2.94 (1H, dd, J = 14.10, 5.2 Hz, S-CH₂CHN), 3.03 (1H, dd, J = 14.10, 5.2 Hz, S-CH₂CHN), 3.13 (2H, t_app, J = 6.2 Hz, S-CH₂CH=CH₂), 4.15 (2H, q, J = 7.0 Hz, OCH₂), 4.89-4.94 (1H, m, -CH-N), 5.08-5.14 (2H, m, S-CH₂CH=CH₂), 5.69-5.77 (1H, m, S-CH₂CH=CH₂), 6.27 (1H, d, J = 15.6 Hz, –CO–CH=C), 6.76 (d, J = 7.2 Hz, -CH-NH-C=O), 6.82 (1H, d, J = 8.0 Hz, Ar), 6.86 (1H, d, J = 8.0 Hz, Ar), 7.02 (1H, s, Ar), 7.48 (1H, d, J = 15.5 Hz, Ar-CH=C); ¹³C NMR (CDCl₃, 125 MHz): δ 10.48 (CH₃), 22.0 (CH₂), 32.77 (S-CH₂CHN), 35.32 (S-CH₂CH=CH₂), 52.31 (CH-N), 67.90 (OCH₂), 114.74 (Ar), 115.50 (Ar), 116.63 ((C=C-CO-), 118.24 (S-CH₂CH=CH₂), 121.86 (Ar), 127.15 (Ar), 133.60 (S-CH₂CH=CH₂), 143.13 (Ar-C=C), 144.33 (Ar-O), 146.97 (Ar-O), 167.15 (-NH-C=O), 171.45 (CH-C=O)-O); EIMS: m/z 366.1375 [M + H]⁺, Calcd for C₁₈H₂₄NO₅S: 366.1377.
Butyl N-[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoyl]-S-2-propen-1-yl-L-cysteinate (9d): M.p. 119-121°C; [α]²⁵ + 11.0 (C = 0,65, CHCl₃); IR (KBr, cm^-1): ν _max 3467 (OH), 3206 (N-H), 1734 and 1662 (C=O), 1265 (C-O-C), 1209 ((C=O)-O); ¹H NMR (CDCl₃, 600 MHz): δ 0.93 (3H, t, J = 7.0 Hz), 1.32-1.46 (CH₂, m), 1.57-1.71 (CH₂, m), 2.94 (1H, dd, J = 14.10, 5.2 Hz, S-CH₂CHN), 3.03 (1H, dd, J = 14.10, 5.2 Hz, S-CH₂CHN), 3.13 (2H, t_app, J = 6.2 Hz, S-CH₂CH=CH₂), 4.19 (2H, q, J = 6.2 Hz, OCH₂), 4.88-4.94 (1H, m, -CH-N), 5.07-5.15 (2H, m, S-CH₂CH=CH₂), 5.66-5.80 (1H, m, S-CH₂CH=CH₂), 6.27 (1H, d, J = 15.6 Hz, –CO–CH=C), 6.73 (d, J = 7.2 Hz, -CH-NH-C=O), 6.83 (1H, d, J = 8.2 Hz, Ar), 6.88 (1H, d, J = 8.2 Hz, Ar), 7.04 (1H, s, Ar), 7.49 (1H, d, J = 15.5 Hz, Ar-CH=C); ¹³C NMR (CDCl₃, 125 MHz): δ 13.77 (CH₃), 19.19 (CH₂), 30.60 (CH₂), 32.80 (S-CH₂CHN), 35.34 (S-CH₂CH=CH₂), 52.33 (CH-N), 66.19 (OCH₂), 114.77 (Ar), 115.52 (Ar), 116.70 ((C=C-CO-), 118.22 (S-CH₂CH=CH₂), 121.84 (Ar), 127.19 (Ar), 133.63 (S-CH₂CH=CH₂), 143.11 (Ar-C=C), 144.38 (Ar-O), 146.96 (Ar-O), 167.10 (-NH-C=O), 171.41 (CH-C=O)-O); EIMS: m/z 380.1532 [M + H]⁺, Calcd for C₁₉H₂₆NO₅S: 380.1536.
Pentyl N-[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoyl]-S-2-propen-1-yl-L-cysteinate (9e): M.p. 111-113°C; [α]²⁵ + 14.4 (C = 0,80, CHCl₃); IR (KBr, cm^-1): ν _max 3460 (OH), 3206 (N-H), 1734 and 1655 (C=O), 1265 (C-O-C), 1209 ((C=O)-O); ¹H NMR (CDCl₃, 600 MHz): δ 0.89 (3H, t, J = 6.5 Hz), 1.28-1.37 (CH₂, m), 1.61-1.69 (CH₂, m), 2.92 (1H, dd, J = 14.10, 5.2 Hz, S-CH₂CHN), 3.03 (1H, dd, J = 14.10, 5.2 Hz, S-CH₂CHN), 3.13 (2H, t_app, J = 6.2 Hz, S-CH₂CH=CH₂), 4.17 (2H, q, J = 6.2 Hz, OCH₂), 4.87-4.94 (1H, m, -CH-N), 5.07-5.14 (2H, m, S-CH₂CH=CH₂), 5.68-5.77 (1H, m, S-CH₂CH=CH₂), 6.25 (1H, d, J = 15.6 Hz, –CO–CH=C), 6.78-6.87 (3H, m), 7.01 (1H, s, Ar), 7.46 (1H, d, J = 15.5 Hz, Ar-CH=C); ¹³C NMR (CDCl₃, 125 MHz): δ 14.06 (CH₃), 18.12 (CH₂), 21.20 (CH₂), 28.06 (CH₂), 32.74 (S-CH₂CHN), 35.29 (S-CH₂CH=CH₂), 52.31 (CH-N), 66.47 (OCH₂), 114.54 (Ar), 115.47 (Ar), 116.59 ((C=C-CO-), 118.21 (S-CH₂CH=CH₂), 121.98 (Ar), 127.13 (Ar), 133.60 (S-CH₂CH=CH₂), 143.11 (Ar-C=C), 144.40 (Ar-O), 146.99 (Ar-O), 167.18 (-NH-C=O), 171.55 (CH-C=O)-O); EIMS: m/z 394.1688 [M + H]⁺, Calcd for C₂₀H₂₈NO₅S: 394.1691.
4.2. Biological activity assaysCell lines and culture mediumBiological assays were performed using an adenocarcinoma colon cancer cell line (SW480) and non-malignant cells (CHO-K1). These were obtained from the European Collection of Authenticated Cell Cultures (ECACC, England) and maintained in Dulbecco’s Modified Eagle Medium, supplemented with 10% heat-inactivated (56 °C) horse serum, 1% penicillin/streptomycin and 1% non-essential amino acids (Gibco Invitrogen, Carlsbad, USA). For all experiments, horse serum was reduced to 3%, and the medium was supplemented with 5 mg/ml transferrin, 5 ng/mL selenium and 10 mg/ml insulin (ITS-defined medium; Gibco, Invitrogen, Carlsbad, USA) (32 ).
Cell Viability The cell viability of the synthesized hybrids, lead, and reference compounds was evaluated through Sulforhodamine B (SRB) assay, a colorimetric test that is based on staining of total cellular protein of adherent cells. The cells were seeded to a ﬁnal density of 20.000 cells/well in 96-well tissue culture plates and incubated at 37 °C in a humidified atmosphere at 5% CO₂. All cultures were allowed to grow for 24 h and afterward they were treated with DMSO (dimethylsulfoxide; vehicle control 1%) or increasing concentrations (0.01–0.1 mM) of the synthesized hybrids, as well as SAC and caffeic acid (Lead compounds) and 5-fluorouracil (5-FU; the standard drug). After treatment, the cells were fixed with trichloroacetic acid (50% v/v) (MERCK) for a period of one h at 4 °C. The cell proteins were determined by staining with 0.4% (w/v) SRB (Sigma-Aldrich, United States), then they were washed with 1% acetic acid for the removal of unbound SRB and left for air-drying. Protein bound SRB was solubilized in 10 mM Tris-base and the absorbance was measured at 492 nm in a microplate reader (Mindray MR-96A) (33 ). All of the experiments were performed at least in quintuplicate.
Antiproliferative activityAntiproliferative effect of the most active compounds was also tested through Sulforhodamine B (SRB) assay. Briefly, the cells were seeded to a ﬁnal density of 2500 cells/well in 96-well tissue culture plates and incubated in the same conditions described for viability. The cultures were allowed to grow for 24 h and then were treated with increasing concentrations of the selected hybrids (0.1 – 0.55 mM, ranges depended on the IC₅₀ -50% inhibitory concentration- values) or DMSO (vehicle control, 1%), for 0, 2, 4, 6, and 8 days. Culture media was replaced every 48 h. After each incubation time, the cells were fixed, stained, and read as previously described for this technique (32 ).
Measurement of Mitochondrial Membrane Potential (ΔΨm)Mitochondrial membrane permeability changes were assessed through the fluorescent dye DiOC₆(3,3’-dihexyloxacarbocyanine iodide, Thermo Fisher Scientiﬁc, Waltham, MA, USA), and propidium iodide (PI). The cells were seeded to a ﬁnal density of 2.5 x 10⁵ cells/well in 6-well tissue culture plates and were allowed to grow for 24 h. Then, they were treated with hybrids 6e, 9a, 9b, 9c, and 9e with its respective IC₅₀ (0.18, 0.12, 0.12, 0.11, and 0.12 mM, respectively), being harvested by scrapping at 48 h in the same culture mean, and stained with DiOC₆and PI at room temperature for 30 min in darkness. The cells were collected to analyze 10,000 events by ﬂow cytometry with excitation at 488 nm and detection of the emission with the green (530/15 nm) and the red (610/20 nm) ﬁlters. This method allowed us quantifying cells with depolarized mitochondrial membrane (34 ).
Cell cycle analysisCell cycle distribution was analyzed by labelling cells with propidium iodide (PI). Assays were carried out as described by Nicoletti et al. (1991). In brief, cells were seeded in 6-well tissue culture plates at a density of 2.5 x 10⁵ cells/well, incubated at 37 °C in a 5% CO₂ atmosphere. The cultures were allowed to grow for 24 h and then were treated for 48 h with 1% DMSO (vehicle control) or hybrids 6e, 9a, 9b, 9c, and 9e with the IC₅₀ for each compound (0.18, 0.12, 0.12, 0.11, and 0.12mM, respectively). After the treatment, the cells were collected by scraping and the centrifuged cell pellet was resuspended with phosphate buffered saline (PBS). The cell suspension was fixed in 1.8 mL 70% ethanol at 4°C overnight, afterward, these were centrifuged, washed twice in PBS and resuspended in 300 µL of PBS containing 0.25 mg/mL RNAse (Type I-A, Sigma-Aldrich, Germany) and 0.1 mg/mL PI. Following the incubation in the dark at room temperature for 30 min, the PI ﬂuorescence of 10,000 cells was analyzed using a FACS Canto II ﬂow cytometer and the software BD FACS Diva 6.1.3. (BD Biosciences, San Jose). PI signal was analyzed with excitation at 488 nm, using a Sapphire laser, and fluorescence was detected at 610nm. The cell clumps were excluded with the PI-Area vs PI-Width signals. The cell cycle model was ﬁxed using the software FlowJo 7.6.2 (Ashland, OR, USA), applying the Dean-Jett-Fox model (34 , 35 (link)).
Statistical analysisAll experiments were performed at least three times. The data are reported as mean ± SE (standard error). Statistical differences between the control group (non-treated) and treated cells were evaluated by one-way ANOVA followed by the Dunnett′s test. Values with p ≤ 0.05 were considered significant. The data were analyzed with GraphPad Prism version 7.04 for Windows (Graph Pad Software, San Diego, California, USA).

Castrillón W., Herrera-R A., Prieto L.J., Conesa-Milián L., Carda M., Naranjo T., Maldonado M.E, & Cardona-G W. (2019). Synthesis and in-vitro Evaluation of S-allyl Cysteine Ester - Caffeic Acid Amide Hybrids as Potential Anticancer Agents. Iranian Journal of Pharmaceutical Research : IJPR, 18(4), 1770-1789.

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complex solution in xylene, Pt ≈ 2%), allyl alcohol, 4-(dimethylamino)pyridine
(DMAP), N,N′-diisopropylcarbodiimid
(DIC, 18.4 mL, 122.4 mmol, 3.4 equiv), 5-norbornene-2-carboxylic acid
(mixture of endo and exo, predominantly endo), 5-norbornene-2-carbonitrile, first-generation Grubbs’
catalyst, 2,2-dimethoxy-2-phenylacetophenone (DMPA), and 2,2′-(ethylenedioxy)diethanethiol
(CL) were purchased from Sigma-Aldrich. Poly(vinyl alcohol)
(PVA, R&G-PVA-Folientrennmittel) was purchased from Suter-Kunststoff
AG. Methanol (MeOH), dichloromethane (DCM), ethyl acetate (EA), toluene
(Tol), tetrahydrofuran (THF), and heptane were purchased from VWR.
All chemicals were of reagent grade and used without purification;
only toluene was dried over sodium using benzophenone as an indicator
and DCM over calcium hydride and distilled before use.

Adeli Y., Raman Venkatesan T., Mezzenga R., Nüesch F.A, & Opris D.M. (2024). Synthesis of Bottlebrush Polymers with Spontaneous Self-Assembly for Dielectric Generators. ACS Applied Polymer Materials, 6(9), 4999-5010.

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Publication 2024

Functionalization of Cellulose Substrate

Not available on PMC !

Example 1

Materials:

Cellulose filter paper (Whatman brand), was used as a cellulose substrate and was dried in a vacuum oven at 65° C. for 14 hours prior to use. 2,2-Bis(hydroxymethyl)propionic acid (Bis-MPA), allyl bromide, thionyl chloride (SOCl₂), N,N′-dicyclohexylcarbodiimide (DCC), pyridine, 4-dimethyl(aminopyridine) (DMAP) 1H,1H,2H,2H-perfluorodecanethiol, 1-decanethiol, 2-mercaptoethanol, 2,2-dimethoxy-2-phenyl-acetophenone (DMPA) were purchased from Sigma-Aldrich. Trimethylamine (Et₃N), toluene, dichloromethane (DCM), dry DCM and ethyl alcohol were purchased from Bio-lab ltd. Concentrated hydrochloric acid (HCl) and sodium hydroxide (NaOH) pellets were purchased from Merck. All the materials were used as received.

US11858887B2. Linker compounds, methods of producing the same and uses thereof (2024-01-02). Shenkar College of Engineering and Design [IL]. Inventors: Elizabeth Amir [IL], Daniel Anavi [IL].

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Patent 2024

2-Mercaptoethanol acetophenone allyl bromide Aminopyridines Anhydrides Cellulose Chlorides Dicyclohexylcarbodiimide Ethanol Hydrochloric acid Methylene Chloride Pellets, Drug propionic acid pyridine Sodium Hydroxide Strains thionyl chloride Toluene trimethylamine Vacuum

Extraction and Analysis of Plant Metabolites

Absolute ethanol, allyl isothiocyanate, barium acetate, ß-mercaptoethanol, cetyltrimethylammonium bromide (CTAB), chloroform, ethylenediaminetetraacetic acid (EDTA 500 mM), formic acid (FA), isoamyl alcohol, lead(II) acetate, phenyl isothiocyanate, polyvinylpyrrolidone (PVP), sodium acetate, sodium chloride, and Tris–HCl pH 7.5 were purchased from Sigma-Aldrich (St. Louis, MO, USA). Aryl sulfatase from Helix pomatia with 10,000 units (type H-1; EC 3.1.6.1) was obtained from Sigma-Aldrich. DEAE Sephadex A-25 was purchased from Cytiva (Marlborough, MA, USA). Glucotropaeolin potassium salt was obtained from Extrasynthese (Genay Cedex, Rhône, France). Plant Total RNA Mini Kit without DNase was purchased from Geneaid (New Taipei City, Taiwan). High-performance liquid chromatography (HPLC) solvents acetonitrile and methanol were purchased from Daejung (Republic of Korea), and water and dichloromethane were obtained from Thermo Fisher Scientific (Waltham, MA, USA).

Truong T.Q., Park Y.J., Jeon J.S., Choi J., Koo S.Y., Choi Y.B., Huynh P.K., Moon J, & Kim S.M. (2024). Myrosinase isogenes in wasabi (Wasabia japonica Matsum) and their putative roles in glucosinolate metabolism. BMC Plant Biology, 24, 353.

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Publication 2024

Stable Isotope Analysis of Organosulfur Compounds

According to the IUPAC protocol [40 (link)], the ¹³C/¹²C values are expressed in the delta scale (δ‰), against the international standards V-PDB (Vienna-Pee Dee Belemnite) according to Equation (1):

Equation 1.

where ref is the international measurement standard, sample is the analysed sample, and i_E/j_E is the isotope ratio between heavier and lighter isotopes. The delta values were multiplied by 1000 and expressed in units “per mil” (‰). Each sample was analysed in triplicate.
The δ(¹³C) values were corrected for the instrumental drift and calculated against standard allyl alcohol (−24.8 ± 0.2 ‰), diallyl disulfide (−29.9 ± 0.2 ‰) and diallyl trisulfide (−28.6 ± 0.2 ‰) and injected in triplicate at the beginning and at the end of each analytical sequence. The real values of the working standards were obtained by analysing them through an elemental analyser-isotope ratio mass spectrometry EA-IRMS (Flash 1112, Thermo Scientific, Bremen, Germany) interfaced to a DELTA V isotope ratio mass spectrometer (Thermo Scientific) through a ConFlo IV dilutor (Thermo Finnigan, Bremen, Germany) against the international standards USGS 40 (δ(¹³C) = −26.39 ± 0.04 ‰) and IAEA–CH–6 sucrose (δ(¹³C) = −10.45 ± 0.04 ‰) (U.S. Geological Survey, Reston, VA, USA), NBS-22 fuel oil (δ(¹³C) = −30.03 ± 0.05 ‰), (IAEA-International Atomic Energy Agency, Vienna, Austria).

Pianezze S., Paolini M., D'Archivio A.A, & Perini M. (2024). Gas chromatography-stable isotope ratio mass spectrometry prior solid phase microextraction and gas chromatography-tandem mass spectrometry: development and optimization of analytical methods to analyse garlic (Allium sativum L.) volatile fraction. Heliyon, 10(9), e30248.

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Publication 2024

Top products related to «Allyl alcohol»

Allyl alcohol by Merck Group

Sourced in United States

Allyl alcohol is a colorless, flammable liquid chemical compound with the molecular formula C3H6O. It has a pungent odor and is commonly used as a chemical building block in the synthesis of other organic compounds.

Dimethyl sulfoxide (dmso) by Merck Group

Sourced in United States, Germany, United Kingdom, China, Italy, Sao Tome and Principe, France, Macao, India, Canada, Switzerland, Japan, Australia, Spain, Poland, Belgium, Brazil, Czechia, Portugal, Austria, Denmark, Israel, Sweden, Ireland, Hungary, Mexico, Netherlands, Singapore, Indonesia, Slovakia, Cameroon, Norway, Thailand, Chile, Finland, Malaysia, Latvia, New Zealand, Hong Kong, Pakistan, Uruguay, Bangladesh

DMSO is a versatile organic solvent commonly used in laboratory settings. It has a high boiling point, low viscosity, and the ability to dissolve a wide range of polar and non-polar compounds. DMSO's core function is as a solvent, allowing for the effective dissolution and handling of various chemical substances during research and experimentation.

Allyl alcohol by Thermo Fisher Scientific

Allyl alcohol is a chemical compound with the formula C3H6O. It is a colorless, flammable liquid with a pungent odor. Allyl alcohol is commonly used as a raw material in the production of various chemicals and materials.

2 2 dimethoxy 2 phenylacetophenone dmpa by Merck Group

Sourced in United States, Germany

2,2-dimethoxy-2-phenylacetophenone (DMPA) is a photoinitiator commonly used in photopolymerization reactions. It is a colorless to pale yellow crystalline solid that absorbs light in the ultraviolet and visible range. DMPA is used to initiate the polymerization of various monomers upon exposure to light.

D glucose by Thermo Fisher Scientific

Sourced in United States, United Kingdom, Germany, France, Australia, China, Italy, New Zealand

D-glucose is a monosaccharide, the simplest form of carbohydrate. It is the primary source of energy for many organisms and serves as a building block for more complex carbohydrates. D-glucose is commonly used in laboratory settings for various analytical and experimental purposes.

Allyl isothiocyanate by Merck Group

Sourced in United States, Germany, United Kingdom, Australia

Allyl isothiocyanate is a colorless, pungent-smelling liquid chemical compound. It is an organic compound with the molecular formula C4H5NS. Allyl isothiocyanate is commonly used as a laboratory reagent.

Fetal bovine serum (fbs) by Thermo Fisher Scientific

Sourced in United States, China, United Kingdom, Germany, Australia, Japan, Canada, Italy, France, Switzerland, New Zealand, Brazil, Belgium, India, Spain, Israel, Austria, Poland, Ireland, Sweden, Macao, Netherlands, Denmark, Cameroon, Singapore, Portugal, Argentina, Holy See (Vatican City State), Morocco, Uruguay, Mexico, Thailand, Sao Tome and Principe, Hungary, Panama, Hong Kong, Norway, United Arab Emirates, Czechia, Russian Federation, Chile, Moldova, Republic of, Gabon, Palestine, State of, Saudi Arabia, Senegal

Fetal Bovine Serum (FBS) is a cell culture supplement derived from the blood of bovine fetuses. FBS provides a source of proteins, growth factors, and other components that support the growth and maintenance of various cell types in in vitro cell culture applications.

Monomers by Merck Group

Sourced in Sao Tome and Principe, United Kingdom

Monomers are the fundamental building blocks of polymers. They are small, reactive molecules that can be linked together through chemical reactions to form larger, more complex macromolecules. The core function of monomers is to serve as the basic units for the synthesis of polymers, which have a wide range of applications in various industries, such as plastics, rubbers, and textiles.

Cyclohexanol by Merck Group

Sourced in United States, Germany

Cyclohexanol is a chemical compound with the formula C6H11OH. It is a colorless, viscous liquid with a mild, pleasant odor. Cyclohexanol is used as an intermediate in the production of various chemicals and pharmaceuticals.

D mannose cell culture grade by Merck Group

D-(+)-mannose (cell culture grade) is a monosaccharide sugar used in cell culture applications. It serves as a carbon source and energy substrate for cell growth and maintenance in vitro.

More about "Allyl alcohol"

Allyl alcohol, also known as 2-propen-1-ol or prop-2-en-1-ol, is a colorless, flammable liquid with a pungent odor.
It is a versatile chemical intermediate used in the production of a wide range of compounds, such as glycerol, acrylic acid, and other important industrial and pharmaceutical substances.
In addition to its use as a chemical building block, allyl alcohol has various other applications.
It can be used as a solvent, a stabilizer, and a cross-linking agent in the synthesis of polymers and resins.
Allyl alcohol is also an important precursor for the production of allyl isothiocyanate, a compound with strong antimicrobial and insecticidal properties.
When handling allyl alcohol, it is crucial to take proper precautions due to its hazardous nature.
Exposure to allyl alcohol can cause irritation to the eyes, nose, and throat, and it can be harmful if inhaled or absorbed through the skin.
Researchers working with allyl alcohol should utilize appropriate personal protective equipment (PPE) and follow safety protocols to ensure their well-being and the integrity of their experiments.
To improve the reproducibility and accuracy of allyl alcohol experiments, researchers can leverage the AI-driven protocols offered by PubCompare.ai.
This platform allows users to easily access and compare protocols from literature, pre-prints, and patents, helping them identify the best methodologies and products for their specific research needs.
By utilizing PubCompare.ai's intelligent, typo-free solutions, researchers can enhance their experimental outcomes and ensure the reliability of their findings.
In addition to allyl alcohol, researchers may also encounter other related compounds in their work, such as DMSO (dimethyl sulfoxide), DMPA (2,2-dimethoxy-2-phenylacetophenone), D-glucose, allyl isothiocyanate, FBS (fetal bovine serum), monomers, cyclohexanol, and D-(+)-mannose (cell culture grade).
Understanding the properties and applications of these substances can provide valuable insights and inform the design of more effective and efficient experiments.