> Chemicals & Drugs > Organic Chemical > Salicylaldehyde

Salicylaldehyde

Salicylaldehyde is an aromatic aldehyde with the chemical formula C6H5CHO.
It is a colorless to pale yellow liquid with a characteristic bitter almond odor.
Salicylaldehyde is used in the synthesis of various pharmaceutical and industrial compounds, and has been studeied for its potential antioxidant, antimicrobial, and anti-inflammatory properties.
Researchers can optimize their salicylaldehyde-related experiments using PubCompare.ai, which leverages AI to identify the best protocols from published literature, preprints, and patents, ensuring reproducibility and accuracy.

Most cited protocols related to «Salicylaldehyde»

Quantifying Labile Iron Pool Using Calcein

Calcein acetoxymethyl ester (CA-AM) was obtained from Molecular Probes. The iron chelator, isonicotinoyl salicylaldehyde hydrazone (SIH) (a gift from Dr. P. Ponka, Lady Davis Institute for Medical Research, Montreal, Canada) was prepared as a 50 mM stock solution in dimethyl sulfoxide (DMSO). Briefly, 25,000 – 50,000 cells were cultured in 96-well plates (Black with Clear Bottom purchased from Coring) overnight. Cells were loaded with 2 μM CA-AM for 15 to 30 minutes at 37°C, and then washed with PBS. 100 μM starch-conjugated desferrioxamine (DFO; a generous gift of Biomedical Frontiers, Inc., Minneapolis, MN) was added to cells to remove extracellular iron. Fluorescence was measured at 485 nm excitation and 535 nm emission with a fluorescence plate reader (BioTek Synergy 2). After the fluorescence signal was stabilized, SIH was added at a final concentration of 10 μM to remove iron from calcein, causing dequenching. The change in fluorescence following the addition of SIH (ΔF) was used as an indirect measure of the labile iron pool.

Basuli D., Tesfay L., Deng Z., Paul B., Yamamoto Y., Ning G., Xian W., McKeon F., Lynch M., Crum C.P., Hegde P., Brewer M., Wang X., Miller L.D., Dyment N., Torti F.M, & Torti S.V. (2017). Iron addiction: A novel therapeutic target in ovarian cancer. Oncogene, 36(29), 4089-4099.

Publication 2017

calcein AM Cells Chelating Agents Fluorescence fluorexon Hydrazones Iron Molecular Probes salicylaldehyde starch deferoxamine Sulfoxide, Dimethyl

Synthesis and Characterization of Coumarin Derivatives

All reactions were carried out using commercial materials and reagents without further purification unless otherwise noted. Reaction mixtures were heated by the CEM Discovery microwave apparatus. All reactions were monitored by thin layer chromatography (TLC) on silica gel plates. ¹H NMR and ¹³C NMR data were recorded on a Bruker Avance 400 MHz spectrometer or Bruker Avance III 300 MHz spectrometer (Bruker, Billerica, MA). Chemical shifts are expressed in parts per million values (ppm) and are designated as singlet (s), broad singlet (br s), doublet (d), double doublet (dd), double double doublet (ddd), and triplet (t). Coupling constants (J) are expressed as values in hertz (Hz). The HRMS mass spectra were recorded using Micromass LCT ESI-TOF equipment (Waters Corporation, Milford, MA). Elemental analyses were done with Elementar Vario EL III elemental analyser (Elementar-Straße 1, Langenselbold, Germany). The 3-phenylcoumarin analogues were synthesised using Perkin–Oglialor condensation reaction. The method was developed from the earlier published procedures and transferred to microwave reactor.
Experimental data for 7-hydroxy-3–(4-fluorophenyl)-2H-chromen-2-one (5; Figure 2), 7-hydroxy-3–(4-methoxyphenyl)-2H-chromen-2-one (8; Figure 2) and 7-hydroxy-3–(4-hydroxyphenyl)-2H-chromen-2-one (9; Figure 2) have been published¹⁴ (link). However, the synthesis steps are detailed below for other derivatives studied here (1, 2, 3, 4, 6, 7 and 10Figure 2; Scheme 1). Of these 1–4 have also been synthesised earlier by others prior to this study^15–18 (link). 2; Scheme 1).
A typical procedure (Scheme 1): A mixture of salicylaldehyde derivative (2 mmol) and phenylacetic acid derivative (2.1 mmol), acetic acid anhydride (0.6 ml), and triethylamine (0.36 ml) were placed in a microwave reactor tube and this mixture was heated at 100–170 °C with microwave apparatus for 10–20 min. After cooling, 2 ml of 10% NaHCO₃ solution was added and the precipitate was filtered, dried, and recrystallised from ETOH/H₂O or acetone/H₂O mixture. The acetyl group(s) were removed by treating the compound with MeOH/NaOH(aq) solution for 30–60 min at r.t. The solution was acidified with HCl(aq,) and the precipitate was filtered and recrystallised if needed.
Based on the elemental analysis and/or ¹H-NMR the purity of compounds was >95%.
8-hydroxy-3–(4-methoxyphenyl)-2H-chromen-2-one (1)¹⁵ (link). In the first step 8-acetoxy-3–(4-methoxyphenyl)-2H-chromen-2-one was obtained. Yield 85%; ¹H-NMR (400 MHz, d⁶-DMSO) δ: 2.40 (s, 3H, CH₃C(O)O-Ph), 3.80 (s, 3H (CH₃O-Ph), 7.02 (d, 2H, J³ = 8.1 Hz, H-3′, H-5′), 7.37 (t, 1H, J³ = 7.6 Hz, H-6), 7.43 (d, J³ = 7.7 Hz, 1H, H-7), 7.64–7.69 (m, 3H, H-5, H-2′, H-6′), 8.11 (s, 1H, H-4); ¹³C-NMR (100.6 MHz, d⁶-DMSO) δ: 20.33, 55.20, 113.70, 120.85, 124.41, 124.65, 125.87, 126.50, 126.80, 129.82, 136.70, 138.88, 144.38, 158.83, 159.73 and 168.38. HRMS(ESI): calcd for C₁₈H₁₄O₅Na₁ [M + Na]⁺: 333.07389, found 333.07580. Elemental anal. for C₁₈H₁₄O_5, calc. C% 69.67, H% 4.55, found C% 69.53, H% 4.55. In the second step, 8-hydroxy-3–(4-methoxyphenyl)-2H-chromen-2one was obtained. Yield 81%; ¹H-NMR (400 MHz, d⁶-DMSO) δ: 3.80 (s, 6H (CH₃O−), 7.01 (d, J³ = 8.9 Hz, 2H, H-3′,H-5′), 7.08 (dd, 1H, J³ = 7.0 Hz, J⁴ = 2.6 Hz, H-7), 7.12–7.18 (m, 2H, H-5, H-6), 7.70 (d, 2H J³ = 8.9 Hz, H-2′,H-6′), 8.11 (s, 1H, H-4), 10.19 (s, 1H, Ph-OH). ¹³C-NMR (100.6 MHz, d⁶-DMSO) δ: 55.21, 113.64, 117.64 118.39, 120.55, 124.45, 126.22, 126.91, 129.79, 139.52, 141.42, 144.26, 159.54 and159.76. HRMS(ESI)): calcd for C₁₆H₁₂O₄Na₁ [M + Na]⁺: 291.06333, found 291.06180. Elemental anal. for C₁₆H₁₂O_4, calc. C% 71.26, H% 4.51, found C% 71.64, H% 4.51.
6-hydroxy-3–(4-hydroxyphenyl)-2H-chromen-2-one (2)¹⁹ . In the first step 4–(6-acetoxy-2-oxo-2H-chromen-3-yl)phenyl acetate was obtained. Yield 90%; ¹H-NMR (300 MHz, d⁶-DMSO) δ: 2.30 (s, 3H, CH₃CO(O)-Ph), 2.31 (s, 3H, CH₃CO(O)-Ph), 7.23 (d, 2H, J³ = 8.8 Hz, H-2′, H-6′), 7.40 (dd, J³ = 8.9 Hz, J⁴ = 2.7 Hz, 1H, H-7), 7.49 (d, 1H, J³ = 8.9 Hz, H-8), 7.55 (d, 1H, J⁴ = 2.6 Hz, H-5), 7.76 (d, 2H, J³ = 8.8 Hz, H-3′, H-5′), 8.24 (s, 1H, H-4); ¹³C-NMR (75.5 MHz, d⁶-DMSO) δ: 20.73, 20.82, 116.97, 119.90, 120.77, 121.67, 125.48, 126.67, 129.74, 131.95, 139.84, 146.43, 150.43, 150.76, 159.51, 169.10 and 169.22. In the second step, 6-hydroxy-3–(4-hydroxyphenyl)-2H-chromen-2-one was obtained. Yield 85%; ¹H-NMR (400 MHz, d⁶-DMSO) δ: 6.83 (d, 2H, J³ = 8.8 Hz, H-3′, H-5′), 6.99 (dd, 1H, J³ = 8.8 Hz, J⁴ = 2.9 Hz, H-7), 7.06 (d, 1H, J⁴ = 2.8 Hz, H-5), 7.24 (d, 1H, J³ = 8.9 Hz, H-8), 7.57 (d, 2H, J³ = 8.7 Hz, H-2′, H6′), 8.04 (s, 1H, H-4); ¹³C-NMR (75.5 MHz, d⁶-DMSO) δ: 112.29, 115.00,116.59, 119.15, 120.24, 125.40, 126.71 129.86, 138.51, 146.03, 153.77, 157.90 and 160.13. HRMS(ESI)): calcd for C₁₆H₁₁F₁O₄Na₁ [M + Na]⁺: 277.0477, found 277.0461.
3–(3-hydroxyphenyl)-2H-chromen-2-one (3)²⁰ (link). In the first step, 3–(2-oxo-2H-chromen-3-yl)phenyl acetate was obtained. Yield 87%; ¹H-NMR (400 MHz, d⁶-DMSO) δ: 2.30 (s, 3H, CH₃C(O)O-Ph), 7.20 (ddd, 1H, J³ = 9.0 Hz, J⁴ = 2.2 Hz, J^4′ = 2.3 Hz, H-6′), 7.39 (t, 1H, J³ = 7.6 Hz, H-5′), 7.44 (d(broad), 1H, J³ = 8.3 Hz, H-4′), 7.49–7.53 (m, 2H, H-6, H-2′), 7.62–7.66 (m, 2H, H-7, H-8) 7.79 (dd, 1H, J³ = 8.7 Hz, J⁴ = 1.5 Hz, H-5), 8.32 (s, 1H, H-4); ¹³C-NMR (100 MHz, d⁶-DMSO) δ: 20.86, 115.90, 119.38, 121.81, 122.17, 124.68, 125.69, 125.90, 128.81, 129.31, 131.98, 135.99, 141.13, 150.30, 153.02, 159.51 and 169.23. In the second step, 3–(3-hydroxyphenyl)-2H-chromen-2-one was obtained. Yield 74%; ¹H-NMR (300 MHz, d⁶-DMSO) δ: 6.83 (ddd, 1H, J³ = 8.1 Hz, J⁴ = 2.2 Hz, J^4′ = 2.4 Hz, H-4′), 7.11–7.18 (m, 2H, H-2′, H-6′), 7.26 (t, 1H, J³ = 7.9, H-5′), 7.37 (ddd, 1H, J³ = 7.6 Hz, J⁴ = 1.1 Hz, J^4′= 1.1 Hz, H-6), 7.42 (d, J³ = 8.3 Hz, H-8), 7.61 (ddd, J³ = 7.3 Hz, J⁴ = 1.6 Hz, J⁴′ = 2.6 Hz H-7), 7.83 (dd, 1H, J³ = 8.7 Hz, J⁴ = 1.5 Hz, H-5), 8.20 (s, 1H, H-4), 9.54 (s, 1H,Ph-OH); ¹³C-NMR (75.5 MHz, d⁶-DMSO) δ: 115.45, 115.59, 115.76, 119.13, 119.43, 124.50, 126.86, 128.60, 129.20, 131.60, 135.79, 140.32, 152.87, 157.06, and 159.54. HRMS (ESI): Calcd for C₁₅H₁₀O₄Na₁ [M + Na]⁺: 261.05276, found 261.04980.
6-chloro-3–(3-hydroxyphenyl)-2H-chromen-2-one (4)²¹ (link). In the first step, 3–(6-chloro-2-oxo-2H-chromen-3-yl)phenyl acetate was obtained. Yield 85%; ¹H-NMR (400 MHz, d⁶-DMSO) δ: 2.30 (s, 3H, CH₃C(O)O-Ph), 7.22 (ddd, 1H, J³ = 8.0 Hz, J⁴ = 2.2 Hz, J^4′ = 2.3 Hz, H-6′), 7.48–7.52 (m, 3H, H-8, H-2′, H-5′), 7.62 (m, 1H, H-4′), 7.67 (dd, 1H, J³ = 8.9 Hz, J⁴ = 2.6 Hz, H-7), 7.88 (d, 1H, J⁴ = 2.6 Hz, H-5), 8.27 (s, 1H, H-4).); ¹³C-NMR (100 MHz, d⁶-DMSO) δ: 20.85, 117.96, 120.78, 121.85, 122.47, 125.93, 126.88, 127.70, 128.31, 129.41, 131.45, 135.67, 139.82, 150.30, 151.66, 159.10 and169.22. In the second step, 6-chloro-3–(3-hydroxyphenyl)-2H-chromen-2-one was obtained. Yield 80%; %; ¹H-NMR (400 MHz, d⁶-DMSO) δ:), 6.84 (ddd, 1H, J³ = 8.0 Hz, J⁴ = 2.4 Hz, J^4′ = 2.3 Hz, H-6′), 7.10–7.15 (m, 2H), 7.27 (t, 1H, J³ = 7.9 Hz, H-5′), 7.47 (d, 1H, J³ = 8.9 Hz, H-8), 7.65 (dd, 1H, J³ = 8.3 Hz, J⁴ = 2.6 Hz, H-7), 7.90 (d, 1H, J⁴ = 2.5 Hz, H-5), 8.17 (s, 1H, H-4), 9.57 (s, 1H, Ph-OH); ¹³C-NMR (75.5 MHz, d⁶-DMSO) δ: 115.43, 115.85, 117.79, 119.13, 120.84, 127.53, 127.99, 128.18, 129.26, 131.09, 135.44, 139.03, 151.50, 157.08 and 159.11. HRMS (ESI): Calcd for C₁₅H₉Cl₁O₃Na₁ [M + Na]⁺: 295.01379, found 295.01380.
3–(3-fluoro-4-hydroxyphenyl)-7-methoxy-2H-chromen-2-one (6). In the first step, 2-fluoro-4–(7-methoxy-2-oxo-2H-chromen-3-yl)phenyl acetate was obtained. Yield 75%; ¹H-NMR (400 MHz, d⁶-DMSO) δ: 2.35 (s, 3H, CH₃C(O)O-Ph), 3.88 (s, 3H, CH₃O-Ph), 6.99 (dd, 1H, J³ = 8.6 Hz, J⁴ = 2.4 Hz, H-6), 7.05 (d, 1H, J⁴ = 2.4 Hz, H-8), 7.37 (t, 1H, J = 8.3 Hz, H-6′), 7.62 (d, J = 8.5 Hz, 1H, H-5′), 7.68 (d, J = 8.6 Hz, 1H, H-5), 7.74 (dd, J^H-F = 12.1 Hz, J⁴= 2.0 Hz, H-3′), 8.31 (s, 1H, H-4); ¹³C-NMR (100 MHz, d⁶-DMSO) δ: 20.19, 55.97, 100.25, 112.79, 116.35 (d, J^C–F = 20 Hz), 121.02 (d, J^C-F = 1.9 Hz), 123.83, 124.79 (d, J^C-F = 3.2 Hz), 129.86, 134.24 (d, J^C–F = 7.7 Hz), 137.20 (d, J^C-F = 13.1 Hz), 141.55, 153.00 (J^C-F = 246.1 Hz), 154.92, 159.65 and 162.69, 168.19. In the second step, 3–(3-fluoro-4-hydroxyphenyl)-7-methoxy-2H-chromen-2-one was obtained. Yield 70%; ¹H-NMR (400 MHz, d⁶-DMSO) δ: 3.87 (s, 3H, CH₃O-Ph), 6.96–7.03 (m, 3H, H-6, H-8, H-5′), 7.41 (d, 1H, J³ = 8.4, H-6′), 7.57 (dd, 1H, J^H-F = 13.1 Hz, J⁴ = 2.2 Hz (H-H), 1H, H-2′), 7.66 (d, 1H, J³ = 8.4, H-5), 8.18 (s, 1H, H-4), 10.09 (s, 1H, Ph-OH). ¹³C-NMR (75.5 MHz, d⁶-DMSO) δ: 55.91, 100.16, 112.61, 113.04, 115.95 (d, J^C-F = 20 Hz), 117.37 (d, J^C-F = 3.3 Hz), 121.78 (J^C-F = 2.0 Hz), 124.54 (d, J^C-F = 3.0 Hz), 126.08 (d, J^C-F = 7.0 Hz), 129.49, 139.62, 145.0 (J^C-F = 13 Hz), 150.46 (d, J^C-F = 240 Hz), 154.52, 159.87 and 162.19. HRMS (ESI): Calcd for C₁₆H₁₁F₁O₄Na₁ [M + Na]⁺: 309.0539, found 309.0553.
3–(3-fluoro-4-hydroxyphenyl)-6-methoxy-2H-chromen-2-one (7). In the first step, 2-fluoro-4–(6-methoxy-2-oxo-2H-chromen-3-yl)phenyl acetate was obtained. Yield 66%; ¹H-NMR (400 MHz, d⁶-DMSO) δ: 2.33 (s, 3H, CH₃C(O)O-Ph), 3.82 (s, 3H (CH₃O-Ph), 7.23 (dd, 1H, J³ = 9.0 Hz, J⁴ = 3.0 Hz, H-7), 7.30 (d, 1H, J⁴ = 3.0 Hz, H-5), 7.35 (d, 1H, J³ = 9.2 Hz, H-8), 7.61 (d, 1H, J³ = 8.5 Hz, H-5′), 7.75 (dd, 1H, J^H-F = 12.0 Hz, J⁴ = 1.7 Hz (H-H), 1H, H-2′), 8.30 (s, 1H, H-4); ¹³C-NMR (100.6 MHz, d⁶-DMSO) δ: 20.22, 55.69, 110.83, 116.67, 117.02, 119.66, 123.96, 125.10, 135.96, 141.18, 147.44, 151.78, 154.23, 155.70, 159.53 and 168.21. In the second step, 3–(3-fluoro-4-hydroxyphenyl)-6-methoxy-2H-chromen-2-one was obtained. Yield 71%; ¹H-NMR (400 MHz, d⁶-DMSO) δ: 3.81 (s, 3H (CH₃O-Ph), 7.02 (dd, 1H, J³ = 9.2 Hz, H-6′), 7.18–7.28 (m, 1H, H-5, H-7), 7.35 (d, J³ = 9.0 Hz, H-8), 7.42 (d, 1H, J³ = 8.4 Hz, H-5′), 7.57 (dd, 1H, J^H-F = 13.0 Hz, J⁴ = 2.2 Hz (H-H), 1H, H-2′), 8.17 (s, 1H, H-4), 10.19 (s, 1H, Ph-OH); ¹³C-NMR (100.6 MHz, d⁶-DMSO) δ: 55.66, 110.59, 116.67, 117.02, 119.66, 123.96, 125.10, 135.96, 141.18, 147.44, 151.78, 154.23, 155.70, 159.53 and 168.21. HRMS (ESI): Calcd for C₁₆H₁₁F₁O₄Na₁ [M + Na]⁺: 309.0539, found 309.0521.
3–(1H-imidazol-1-yl)-2H-chromen-2-one (10). Yield: 39% light brown solid; R_f=0.18 (EtOAc); ¹H-NMR (300 MHz, d⁶-DMSO) δ: 7.10 (br s, 1H, H-4′), 7.44 (apparent td, J³= 7.5 Hz, J⁴=1.0 Hz, 1H, H-6), 7.51 (d, J³=8.3 Hz, 1H, H-8), 7.64–7.70 (m, two overlapping signals, 2H, H-7 and H-5′), 7.77 (dd, J³=7.7 Hz, J⁴=1.5 Hz, 1H, H-5), 8.16 (br s, 1H, H-2′), 8.34 (s, 1H, H-4). ¹³C-NMR (75 MHz, d⁶-DMSO) δ: 116.06 (C-H8), 118.51 (H5-C-C-C-H4), 119.57 (C-H5′), 123.37 (N-C-C = O), 125.09 (C-H6), 128.63 (C-H4′), 128.80 (C-H5), 131.87 (C-H7), 132.97 (C-H4), 137.12 (N-C(-H2′)=N), 151.78 (H8-C-C-O), 156.83 (C=O). IR (KBr): 1727, 1708, 1630, 1608, 1486, 1318, 1083 and 760. ESI-MS: m/z (rel. abund. %): calculated for (M + Na⁺) = 235.0478, measured 235.0476, Δ = 0.2 mDa. Elemental analysis for C₁₂H₈N₂O₂: calc. C% 67.92, H% 3.80, N% 13.20, found C% 67.49, H% 3.72 and N% 13.13. Mp. 180–182 °C.

Niinivehmas S., Postila P.A., Rauhamäki S., Manivannan E., Kortet S., Ahinko M., Huuskonen P., Nyberg N., Koskimies P., Lätti S., Multamäki E., Juvonen R.O., Raunio H., Pasanen M., Huuskonen J, & Pentikäinen O.T. (2018). Blocking oestradiol synthesis pathways with potent and selective coumarin derivatives. Journal of Enzyme Inhibition and Medicinal Chemistry, 33(1), 743-754.

Publication 2018

Synthesis of Unnatural Amino Acid and Fluorophore Compounds

The unnatural amino acid 3-formyltyrosine was synthesized from BOC-L-tyrosine by the Reimer-Tiemann reaction followed by deprotection with trifluoroacetic acid in dichloromethane. The fluorophore 7-hydrazino-4-methyl coumarin was synthesized from 7-amino-4-methyl coumarin by treatment with nitrous acid followed by SnCl₂. The salicylaldehyde hydrazone of coumarin hydrazine was prepared in ethanol with trifluoroacetic acid catalysis. Procedures and spectroscopic data are detailed in Supporting Information.

Banerjee A., Panosian T.D., Mukherjee K., Ravindra R., Gal S., Sackett D.L, & Bane S. (2010). Site-Specific Orthogonal Labeling of the Carboxy Terminus of α-Tubulin. ACS chemical biology, 5(8), 777-785.

Publication 2010

Amino Acids Catalysis coumarin 7 Coumarins Ethanol hydrazine Hydrazones Methylene Chloride Nitrous Acid salicylaldehyde Spectrum Analysis Trifluoroacetic Acid Tyrosine

Macrophage iron chelation analysis

Thioglycollate-elicited peritoneal exudate cells were stained with phycoerythrin-conjugated F4/80 antibody (eBioscience) and 0.5 μM calcein-AM (Molecular Probes) before being subjected to flow cytometry analysis with a Becton–Dickinson FACScan using CELLQUEST software. The fluorescein channel was employed to detect calcein fluorescence after using forward and side scatter characteristics, as well as F4/80 positivity, to gate on macrophages. In some experiments, the membrane permeable iron chelator salicylaldehyde isonicotinoyl hydrazone (SIH, kindly provided by Dr. Prem Ponka, McGill University) was added to the cells at 5 or 10 μM 30 minutes before staining with calcein.

Wang L., Johnson E.E., Shi H.N., Allan Walker W., Wessling-Resnick M, & Cherayil B.J. (2008). Attenuated inflammatory responses in hemochromatosis reveal a role for iron in the regulation of macrophage cytokine translation. Journal of immunology (Baltimore, Md. : 1950), 181(4), 2723-2731.

Publication 2008

Ascites Cell Membrane Permeability Cells Chelating Agents Flow Cytometry Fluorescein Fluorescence fluorexon Immunoglobulins Iron Macrophage Molecular Probes Phycoerythrin salicylaldehyde isonicotinoyl hydrazone Thioglycolates

Optimizing UV Absorbers for 3D Printed Resins

The focus of our resin formulation efforts is finding one or more UV absorbers that will give the optical properties needed to achieve small void size in the z dimension. Similar to our previous work, ^{11 (link),19 ,31 (link)} we use poly(ethylene glycol) diacry-late (PEGDA, MW258) as the monomer and phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide (Irgacure 819) as the photoinitiator. They are obtained from Sigma-Aldrich (St. Louis, MO) and BASF (Vandalia, Illinois), respectively.
Part of the motivation for use of a PEGDA-based resin is that we have already shown ^{32 (link)} that it has low non-specific adsorption and is suitable for electrophoretic separations. Moreover, Urrios et al. showed that their PEGDA resin formulation could be made bio-compatible with a specific post-processing treatment. ³³ Regarding solvent compatibility, we have found 3D printed PEGDA resins to be compatible with some solvents such as isopropyl alcohol and ethanol, but not others such as acetone and toluene.
As indicated in Fig. 2, we evaluate 20 potential UV absorbers. Their molecular structures are shown in Fig. S2, ESI^†. Nearly all are inexpensive and readily available. The absorbers are avoben-zone, 2,5-bis(5-tert-butyl-benzoxazol-2-yl)thiophene (Benetex OB+), disodium 4,4′-bis(2-sulfonatostyryl)biphenyl (Benetex OB-M1), benzenepropanoic acid (BLS 99-2), 2,3,6,7-tetrahydro-9-methyl-1H,5H-quinolizino(9,1-gh)coumarin (Coumarin 102), Martius Yellow, morin hydrate, nitrofurazone, 2-nitrophenyl phenyl sulfide (NPS), 5,12-naphthacenequinone (NTAQ), octocrylene, phenazine, 1,4-bis-(2-(5-phenyloxazolyl))-benzene (POPOP), Quinoline Yellow, 3,3′,4′,5,6-pentahydroxyflavone (Quercetin), salicylaldehyde, Sudan I, triamterene, UV386A, and 9,10-diethoxyanthracene (UVS-1101). Avobenzone and octocrylene are purchased from MakingCosmetics (Snoqualmie, WA); Benetex OB+, Martius Yellow, morin hydrate, Quinoline Yellow, quercetin, and Sudan I from Sigma-Aldrich (St. Louis, MO); Benetex OB-M1, nitrofurazone, and NPS from TCI America (Portland, OR); Coumarin 102, triamterene, and UVS-1101 from Alfa Aesar (Haverhill, MA); BLS 99-2 from Mayzo (Suwanee, GA); NTAQ and phenazine from Santa Cruz Biotechnology (Dallas, TX); salicylaldehyde from Thermo Fisher Scientific (Waltham, MA); and UV386A from QCR Solutions (St. Lucie, FL). Each chemical is used as received.
Resins studied for 3D printing are prepared by mixing 1% (w/w) Irgacure 819 and the desired concentration of UV absorber with PEGDA, and sonicating for 30 min. All photoinitiator-containing resins are stored in amber glass bottles after mixing.

Gong H., Bickham B.P., Woolley A.T, & Nordin G.P. (2017). Custom 3D printer and resin for 18 μ m × 20 μ m microfluidic flow channels. Lab on a chip, 17(17), 2899-2909.

Publication 2017

Acetone Acids Adsorption Amber AS resin avobenzone Benzene coumarin diphenyl Electrophoresis Ethanol Isopropyl Alcohol Martius yellow Molecular Structure morin hydrate Motivation Nitrofurazone octocrylene Oxides peflavit Phenazines phosphine poly(ethylene glycol)diacrylate Polyethylene Glycols POPOP Quercetin quinoline yellow Resins, Plant salicylaldehyde Solvents Solvent Yellow 14 Sulfides TERT protein, human Thiophene Toluene Triamterene Urination Vision

Most recents protocols related to «Salicylaldehyde»

Chitosan-Salicylaldehyde-β-CD-ZnO NPs Synthesis

Chitosan (deacetylation degree above 85%, CAS. No = 9012-76-4), salicylaldehyde (98.5%, CAS. No = 90-02-8), β-CD (CAS. No = 7585-39-9), ZnO NPs (purity over 97%, > 50 nm), glacial acetic acid, and dimethylformamide (DMF) (≥ 99.8%) were supplied from Sigma-Aldrich, Milwaukee, Wisconsin, USA. All chemicals and solvents used are of analytical grade and are used as received without further purification.

Saeed A.M., Taha A.G., Dardeer H.M, & Aly M.F. (2024). One-pot synthesis of novel chitosan-salicylaldehyde polymer composites for ammonia sensing. Scientific Reports, 14, 239.

Publication 2024

Synthesis of Chs-Sal Polymer Composites

A solution of salicylaldehyde (0.40 g in 10 ml MeOH) was prepared at room temperature with stirring for 6 h before the temperature was raised to 100 °C for 1 h, according to Fig. 1a. Chitosan powder (1.0 g) in 50 ml of glacial acetic acid (1% v/v) was then added. The Chs-Sal polymer was obtained as a yellow powder by evaporating the solvent at room temperature.Figure 1

Synthesis of (a) Chs-Sal polymer, (b) Chs-Sal/β-CD composite, (c) of Chs-Sal/ZnO NPs composite, and (d) Chs-Sal/β-CD/ZnO NPs composite, respectively.

Saeed A.M., Taha A.G., Dardeer H.M, & Aly M.F. (2024). One-pot synthesis of novel chitosan-salicylaldehyde polymer composites for ammonia sensing. Scientific Reports, 14, 239.

Publication 2024

Synthesis of N,N'-bis(salicylaldehyde)-1,2-diaminobenzene

First, 1,2-diaminobenzene (5 mmol) and salicylaldehyde (13.10 mmol) were dissolved and stirred in methanol for 30 min to afford a new Schiff base N,N′-bis(salicylaldehyde)-1,2-diaminobenzene (SDA), which was washed, repeatedly dried and then recrystallized using methanol and a high-quality product (∼70–75%) was obtained (Scheme 2).

Gayathri J., Roniboss A., Sivalingam S, & Sangeetha Selvan K. (2024). Electrochemical sensing of Hg(ii) in chicken liver and snail shell extract samples using novel modified SDA/MWCNT electrodes. RSC Advances, 14(23), 16056-16068.

Publication 2024

Multifunctional Schiff Base Nanomaterial

Not available on PMC !

Sodium alginate (NaA) and PVP were purchased from Sigma-Aldrich as polymeric sources. Salicylaldehyde and O-phenylenediamine (Sigma-Aldrich) were applied to form a Schiff base ligand. Tetraethyl orthosilicate (TEOS), Zinc acetate dihydrate, 3-aminopropyltriethoxylsilane (APTES), dimethylformamide, KOH, NaOH, HNO 3 , nickel and copper nitrates were provided from Sigma-Aldrich.

Moridi H, & Gh A.B. (2024). Functionalization of a cast NaAl/binary ZnO/SiO₂ nanohybrid with amine and Schiff base ligands as an adsorbent of divalent cations in water system. Environmental science and pollution research international, 31(19).

Publication 2024

Synthesis of N2O2 Donor Schiff Base Ligand

The N₂O₂ donor Schiff base ligand, H₂L^a, was prepared by refluxing 2,2-dimethylpropane-1,3-diamine (0.2 mL, ∼2 mmol) with salicylaldehyde (0.4 mL, ∼4 mmol) in methanol (10 mL) for ca. 1 h. To obtain the appropriate reduced counterparts of these Schiff base, the ligand was reduced using sodium borohydride (vide infra).

Bhunia S., Das M., Banerjee S., Drew M.G., Ray P.P, & Chattopadhyay S. (2024). Application of a distinctly bent, trinuclear, end-to-end azide bridged, mixed valence cobalt(iii/ii/iii) complex in the fabrication of photosensitive Schottky barrier diodes. RSC Advances, 14(16), 11185-11196.

Publication 2024

Top products related to «Salicylaldehyde»

Salicylaldehyde by Merck Group

Sourced in Germany, United States

Salicylaldehyde is a colorless to pale yellow liquid compound used as a laboratory reagent. It has the chemical formula C₆H₄(O)CH₂. The compound serves as a versatile intermediate in the synthesis of various 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.

Sodium hydroxide (naoh) by Merck Group

Sourced in Germany, United States, India, United Kingdom, Italy, China, Spain, France, Australia, Canada, Poland, Switzerland, Singapore, Belgium, Sao Tome and Principe, Ireland, Sweden, Brazil, Israel, Mexico, Macao, Chile, Japan, Hungary, Malaysia, Denmark, Portugal, Indonesia, Netherlands, Czechia, Finland, Austria, Romania, Pakistan, Cameroon, Egypt, Greece, Bulgaria, Norway, Colombia, New Zealand, Lithuania

Sodium hydroxide is a chemical compound with the formula NaOH. It is a white, odorless, crystalline solid that is highly soluble in water and is a strong base. It is commonly used in various laboratory applications as a reagent.

Ethylenediamine by Merck Group

Sourced in United States, Germany, United Kingdom, Canada, Spain, Italy, Switzerland, China, Czechia, India

Ethylenediamine is a colorless, flammable liquid with a characteristic ammonia-like odor. It is commonly used as a building block for the synthesis of various chemical compounds in laboratory settings.

5 bromosalicylaldehyde by Merck Group

Sourced in United States, India

5-bromosalicylaldehyde is a chemical compound used as a laboratory reagent. It is a yellow crystalline solid with the chemical formula C₇H₅BrO₂. The compound is commonly used in organic synthesis reactions and as a precursor for other chemical products.

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.

Salicylaldehyde by Thermo Fisher Scientific

Sourced in India, Germany, Belgium

Salicylaldehyde is a colorless to pale yellow liquid chemical compound. It is commonly used as a reagent in organic synthesis and analytical chemistry applications.

Acetonitrile by Merck Group

Sourced in Germany, United States, Italy, India, China, United Kingdom, France, Poland, Spain, Switzerland, Australia, Canada, Brazil, Sao Tome and Principe, Ireland, Belgium, Macao, Japan, Singapore, Mexico, Austria, Czechia, Bulgaria, Hungary, Egypt, Denmark, Chile, Malaysia, Israel, Croatia, Portugal, New Zealand, Romania, Norway, Sweden, Indonesia

Acetonitrile is a colorless, volatile, flammable liquid. It is a commonly used solvent in various analytical and chemical applications, including liquid chromatography, gas chromatography, and other laboratory procedures. Acetonitrile is known for its high polarity and ability to dissolve a wide range of organic compounds.

Ethanol by Merck Group

Sourced in Germany, United States, United Kingdom, Italy, India, France, China, Australia, Spain, Canada, Switzerland, Japan, Brazil, Poland, Sao Tome and Principe, Singapore, Chile, Malaysia, Belgium, Macao, Mexico, Ireland, Sweden, Indonesia, Pakistan, Romania, Czechia, Denmark, Hungary, Egypt, Israel, Portugal, Taiwan, Province of China, Austria, Thailand

Ethanol is a clear, colorless liquid chemical compound commonly used in laboratory settings. It is a key component in various scientific applications, serving as a solvent, disinfectant, and fuel source. Ethanol has a molecular formula of C2H6O and a range of industrial and research uses.

Benzaldehyde by Merck Group

Sourced in United States, Germany, China, India, United Kingdom, Canada, Italy, Spain, Belgium, Australia

Benzaldehyde is a clear, colorless liquid with a characteristic almond-like odor. It is a widely used organic compound that serves as a precursor and intermediate in the synthesis of various chemicals and pharmaceuticals.

What are some common uses and applications of Salicylaldehyde?

Salicylaldehyde is a versatile aromatic aldehyde with a variety of applications in the pharmaceutical and industrial sectors. It is commonly used as a starting material in the synthesis of various pharmaceutical compounds, such as aspirin and other salicylate derivatives. Salicylaldehyde has also been studied for its potential antioxidant, antimicrobial, and anti-inflammatory properties, making it useful in the development of therapeutic agents. Additionally, it finds use in the production of dyes, fragrances, and other industrial chemicals.

What are some common challenges or considerations when working with Salicylaldehyde in the lab?

One of the main challenges in working with Salicylaldehyde is its relatively high volatility and pungent odor, which can make handling and storage tricky. Researchers must take appropriate safety precautions, such as working in a fume hood and using proper personal protective equipment. Another consideration is Salicylaldehyde's potential for oxidation, which can affect its reactivity and stability over time. Proper storage conditions, such as refrigeration and exclusion of air, are important to maintain the quality and integrity of Salicylaldehyde samples.

Are there different variations or types of Salicylaldehyde, and how do they differ?

While Salicylaldehyde typically refers to the common aromatic aldehyde with the chemical formula C6H5CHO, there can be some variations in the form or purity of the compound. For example, Salicylaldehyde may be available in different grades, such as reagent-grade or pharmaceutical-grade, which can have different levels of purity and associated impurities. Additionally, there are some structural analogs or derivatives of Salicylaldehyde, such as substituted Salicylaldehydes, which may have slightly different chemical and physical properties. Researchers should carefully select the appropriate form of Salicylaldehyde for their specific application and needs.

How can PubCompare.ai help optimize the use of Salicylaldehyde in research?

PubCompare.ai can be a valuable tool for researchers working with Salicylaldehyde. The platform allows you to effeciently screen the protocol literature to identify the most effective and reproducible procedures related to Salicylaldehyde. The AI-driven analysis can highlight key differences in protocol effectiveness, enabling you to choose the best option for your specific research goals and ensure accurate and reliable results. By leveraging the insights from PubCompare.ai, you can save time, reduce experimental variability, and have greater confidence in the validity of your Salicylaldehyde-based experiments.

More about "Salicylaldehyde"

Salicylaldehyde, also known as o-hydroxybenzaldehyde or 2-formylphenol, is an aromatic aldehyde with the chemical formula C6H5CHO.
It is a colorless to pale yellow liquid with a characteristic bitter almond odor.
Salicylaldehyde is a versatile compound used in the synthesis of various pharmaceutical and industrial compounds, and has been studied for its potential antioxidant, antimicrobial, and anti-inflammatory properties.
In laboratory research, salicylaldehyde is often used in conjunction with other chemicals like DMSO (dimethyl sulfoxide), sodium hydroxide, ethylenediamine, and 5-bromosalicylaldehyde.
These compounds can be used as solvents, reagents, or precursors in the synthesis and analysis of salicylaldehyde-based materials.
To optimize your salicylaldehyde-related experiments, leveraging tools like PubCompare.ai can be highly beneficial.
This AI-powered platform helps researchers identify the best protocols from published literature, preprints, and patents, ensuring reproducibility and accuracy in their work.
By comparing experimental procedures and identifying the most effective approaches, PubCompare.ai empowers researchers to confidently select the optimal methods and products for their salicylaldehyde studies.
Whether you're investigating the antioxidant properties of salicylaldehyde, exploring its antimicrobial applications, or synthesizing novel salicylaldehyde-derived compounds, PubCompare.ai can be a valuable resource.
The platform's AI-enhanced protocol comparisons can help you navigate the wealth of available information, saving time and improving the quality of your research.
In addition to salicylaldehyde, related compounds like benzaldehyde and its derivatives, such as 5-bromosalicylaldehyde, may also be of interest in your work.
By leveraging the insights and tools provided by PubCompare.ai, you can ensure that your salicylaldehyde-related experiments are conducted with the utmost reproducibility and accuracy, leading to more reliable and impactful research outcomes.