Peiyao, Chen, et al. Food Control 166 (2024): 110683.
To develop the plant-derived active substance vanillin, hydroxypropyl-β-cyclodextrin (HPβCD) was employed to encapsulate vanillin, resulting in the preparation of a chitosan-based edible coating: Vanillin-HPβCD/CH, for the preservation of chicken meat.
Ultrasonic Preparation of Vanillin/HPβCD Inclusion Complex (IC)
The inclusion complex (IC) of vanillin and HPβCD was synthesized using an ultrasonic device. Initially, 0.1 mol of HPβCD was dissolved in 200 mL of water and heated to 60 °C using a temperature-controlled stirrer. Then, ethanol solutions of vanillin at different concentrations were added to the HPβCD solution, mixed at molar ratios of 2:1, 1:1, and 1:2. The solution was continuously stirred at ambient temperature for a duration of 24 hours. Thereafter, it was subjected to ultrasonic cell disruption at 65 W for 30 minutes. The resulting solution was freeze-dried for 72 hours to obtain Vanillin/HPβCD-IC powder, which was then stored in a sealed container at 4 °C.
Bai, Yuchen, et al. Journal of Cleaner Production 316 (2021): 128315.
A novel bio-based antioxidant, 1-(4-hydroxy-3-methoxyphenyl) pent-1-en-3-one (HMPPEO), with a chemical structure similar to ferulic acid (FA), was synthesized through an aldol condensation reaction between biomass-derived vanillin and methyl ethyl ketone (MEK).
General Procedure for HMPPEO Synthesis
To synthesize HMPPEO, 0.03 mol of vanillin was dissolved in 50 mL of methanol in a beaker. Next, 100 mL of MEK and 25 mL of a 10-20 wt% NaOH aqueous solution were added to the mixture, serving as a catalyst. The mixture was then continuously stirred in darkness at 55 °C for 48 hours. Initially, the reaction mixture was bright yellow, gradually turning dark brown as the reaction progressed.
After the reaction period, the mixture was allowed to settle, and the pH was adjusted to 2 using hydrochloric acid (2 M). The crude product was extracted with dichloromethane. The extract phase was collected and washed three times with distilled water, followed by vacuum evaporation at 35 °C to remove the dichloromethane. This yielded a yellowish-brown solid subjected to further purification.
For further purification, steam distillation was employed to remove as much of the residual vanillin as possible. The resulting solid was washed with toluene to remove any potential condensation byproducts. Finally, the product was washed three times with water and freeze-dried under a vacuum for over 48 hours.
Brito, Gabriela B., et al. Food Structure 32 (2022): 100264.
The combination of an emulsion template method with cross-linking modification of chitosan by vanillin allows chitosan to form edible oleogels, thereby offering processed foods that are free from trans fats and potentially possess health-promoting properties.
Chitosan-based oleogels were prepared via an emulsion template method using vanillin as a cross-linking agent, with or without the addition of Tween®60 as an emulsifier. Initially, a chitosan solution (1.5% w/v) was prepared in an acetic acid aqueous solution (1.0% v/v) under magnetic stirring at 50 °C for 2 hours. Ethanolic solutions of vanillin (10% and 30%; w/v) were also prepared. To create an oil-in-water (O/W) emulsion (40:60 v/v), canola oil was dispersed into the chitosan solution (50 mL) using a high-speed disperser at 9000 rpm, followed by the addition of vanillin solution (10 mL) under continuous shearing for 4 minutes. The final emulsions contained 0.75% (w/v) chitosan and 1.0 or 3.0% (w/v) vanillin. If necessary, Tween®60 was added at the maximum allowable concentration for food emulsions (0.4 wt%). The emulsions were then freeze-dried (-60 °C, 0.101 mBar), and the dried product was sheared (9000 rpm/2 minutes) to prepare the oleogels.
Aazam, Elham S., and Renjith Thomas. Journal of Molecular Liquids 395 (2024): 123820.
(E)-2-Methoxy-4-((phenylamino)methyl)phenol, abbreviated as ANVA, is a compound derived from aniline and vanillin. It exhibits significant fluorescence and vibrational characteristics, confirmed by FTIR, UV-Vis, and NMR.
Synthesis of (E)-2-Methoxy-4-((phenylamino)methyl)phenol (ANVA)
In this synthesis process, vanillin (1.52 g, 0.01 mmol) and aniline (0.93 mL, 0.01 mmol) are dissolved in a small amount of ethanol. Subsequently, the two components are mixed and ground together for half an hour. The mixture is then transferred to a 100 mL round-bottom flask and refluxed in a water bath for 5 hours. After refluxing, the mixture is allowed to cool to room temperature. The mixture is then filtered, and the residue is washed with ethanol. The resulting product, referred to as ANVA, is recrystallized in dimethyl sulfoxide (DMSO).
Wang, Huanbo, et al. European Polymer Journal 196 (2023): 112309.
Producing repairable and recyclable polymers with balanced strength and ductility remains a challenge in polymer science. Herein, a wholly bio-based difunctional imine modifier (2VP) is synthesized through a Schiff base reaction between vanillin and a branched diamine (Priamine 1074) in a solvent-free one-pot process. High-biomass-content (about 70%) imine glassy trimers are prepared by reacting 2VP with isocyanates at moderate temperatures (80 °C), using hexamethylene diisocyanate trimer (HDI-T) as a cross-linking agent and isophorone diisocyanate (IPDI) as a chain extender.
Preparation of 2VP
Vanillin (3.04 g, 0.02 mol) and Priamine 1074 (5.9 g, 0.011 mol) are added to a 50 mL round-bottom flask equipped with a mechanical stirrer. The flask is placed in an oil bath at 85 °C and stirred for 2 hours. The resulting 2VP is then transferred to a 50 mL beaker and dried in a vacuum oven at 80 °C for 24 hours.
Preparation of 2VPT and 2VPTI
2VP (4 g, 0.005 mol) is placed in a 50 mL beaker containing 20 mL of THF and a magnetic stir bar. Once 2VP is fully dissolved in THF, HDI-T is added to the solution and stirred for 10 minutes. The solution is then poured into PTFE molds and left in a fume hood at room temperature for most of the solvent to evaporate, forming a solid product. The molds are placed in a vacuum oven at 80 °C for 24 hours to ensure complete curing of 2VPT. For 2VPTI samples, the preparation steps are identical.
Güngör, Özlem, and Levent Nuralin. Journal of Molecular Structure 1310 (2024): 138371.
Novel symmetric diimines D1 and D2 were prepared through the condensation reaction of ortho-vanillin with 2-nitro-p-phenylenediamine or 4-nitro-o-phenylenediamine. The diimines were selectively reduced to their amino derivatives and then reacted with terephthalaldehyde to obtain novel symmetric hexa-imines (H1 and H2).
Synthesis of Diimine Schiff Bases (D1 and D2)
Ortho-vanillin (4.0 equivalents) was dissolved in anhydrous ethanol (20 mL). This solution was slowly added dropwise to an ethanolic solution of the amine (2.0 equivalents). The resulting mixture was stirred and refluxed for 5 hours. The obtained precipitate was filtered and dried in the air. Recrystallization from anhydrous ethanol was performed.
Synthesis of Hexa-Imine Schiff Bases (H1 and H2)
Diimine (D1 or D2) (1.0 equivalent) was dissolved in an EtOH-H2O mixture (40:40 mL). Solid Na2S2O4 (5.0 equivalents) was slowly added to this solution, and the mixture was stirred at 50 ºC for one hour to complete the reduction process. Subsequently, a solution of terephthalaldehyde in ethanol (0.5 equivalent, 20 mL) was added dropwise to the amine derivative solution of the diimine. The resulting mixture was stirred at 50 °C for 6 hours and then allowed to stand at room temperature for several days. The crude precipitate was washed with warm water and ethanol.
What is the molecular formula of vanillin?
The molecular formula of vanillin is C8H8O3.
What functional groups are present in vanillin?
The functional groups present in vanillin include aldehyde, hydroxyl, and ether.
What is the primary component of the extract of the vanilla bean?
The primary component of the extract of the vanilla bean is vanillin.
What is the difference between vanillin and ethylvanillin?
The difference between vanillin and ethylvanillin is that ethylvanillin has an ethoxy group (-O-CH2CH3) instead of a methoxy group (-O-CH3).
Why is synthetic vanillin now used more often than natural vanilla extract as a flavoring agent in foods, beverages, and pharmaceuticals?
Synthetic vanillin is now used more often than natural vanilla extract due to its scarcity and expense.
What is the purify of vanillin?
The purity of vanillin is 95%+.
What is the appearance of vanillin?
The appearance of vanillin is crystalline needles.
What is the boiling point of vanillin?
The boiling point of vanillin is 170 °C.
What is the primary application of vanillin?
The primary application of vanillin is in perfumes.
What is the InChI Key of vanillin?
The InChI Key of vanillin is MWOOGOJBHIARFG-UHFFFAOYSA-N.
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