Synthesis and Characterization of Citral-Methylanthranilate Schiff Base, Relationship Between Synthesis Time and Some Physical Properties

Irawan, Candra; Nur, Luthfiyah; Mellisani, Bella; Arinzani,; Hanafi, Hanafi

doi:10.31788/rjc.2019.1225063

Cited by 3 publications

(3 citation statements)

References 12 publications

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“…Specific reaction conditions, such as hydrolysis, temperature changes, as well as the action of light, oxygen, enzymes, or microorganisms, can be used to liberate the many different chemical functionalities. For example, Schiff bases have been studied because they have a low volatility and, at the same time, they can be hydrolyzed in an acidic environment [ 22 , 38 , 39 , 40 ]. The hydrolysis is a crucial step and by regulating it, it is possible to prolong or shorten the time in which the fragrance is perceived.…”

Section: Introductionmentioning

confidence: 99%

Controlled Lactonization of o-Coumaric Esters Mediated by Supramolecular Gels

Cenciarelli

Falini

Giuri

et al. 2023

Gels

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Fragrances are volatile organic compounds widely used in our daily life. Unfortunately, the high volatility required to reach human receptors reduces their persistency in the air. To contrast this effect, several strategies may be used. Among them, we present here the combination of two techniques: the microencapsulation in supramolecular gels and the use of profragrances. We report a study on the controlled lactonization of four esters derived from o-coumaric acid. The ester lactonization spontaneously occurs after exposure to solar light, releasing coumarin and the corresponding alcohol. To determine the rate of fragrance release, we compared the reaction in solution and in a supramolecular gel and we demonstrated that the lactonization reaction always occurs slower in the gel. We also studied the more suitable gel for this aim, by comparing the properties of two supramolecular gels obtained with the gelator Boc-L-DOPA(Bn)2-OH in a 1:1 ethanol/water mixture in different gelator concentration (0.2% and 1% w/v). The gel prepared with 1% w/v gelator concentration is stronger and less transparent than the other and was used for the profragrances encapsulation. In any case, we obtained a significative reduction of lactonization reaction in gel, compared with the same reaction in solution.

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Section: Introductionmentioning

confidence: 99%

Controlled Lactonization of o-Coumaric Esters Mediated by Supramolecular Gels

Cenciarelli

Falini

Giuri

et al. 2023

Gels

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“…In this scenario, Schiff bases (SB) represent valid profragrances that can be synthesized starting from odorant aldehydes and primary amines through a condensation reaction [ 14 , 15 , 16 ]. The reaction is reversible, and the SB can be readily hydrolyzed to the starting materials in aqueous environments, mainly in acidic conditions [ 17 ].…”

Section: Introductionmentioning

confidence: 99%

Controlled Hydrolysis of Odorants Schiff Bases in Low-Molecular-Weight Gels

Nicastro

Black

Ravarino

et al. 2022

IJMS

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Imines or Schiff bases (SB) are formed by the condensation of an aldehyde or a ketone with a primary amine, with the removal of a water molecule. Schiff bases are central molecules in several biological processes for their ability to form and cleave by small variation of the medium. We report here the controlled hydrolysis of four SBs that may be applied in the fragrance industry, as they are profragrances all containing odorant molecules: methyl anthranilate as primary amine, and four aldehydes (cyclamal, helional, hydroxycitronellal and triplal) that are very volatile odorants. The SB stability was assessed over time by HPLC-MS in neutral or acidic conditions, both in solution and when trapped in low molecular weight gels. Our results demonstrate that it is possible to control the hydrolysis of the Schiff bases in the gel environment, thus tuning the quantity of aldehyde released and the persistency of the fragrance.

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“…INTRODUCTION: Schiff's bases, named after Hugo Schiff, are formed when, under specific conditions, any primary amine interacts with an aldehyde or a ketone 1 . Structurally a Schiff's base is an aldehyde or ketone nitrogen analogue in which the imine or the azomethane group has been substituted for the carbonyl group, and it has an ability to modulate the activities of many enzymes involved in metabolism.…”

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confidence: 99%

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2022

IJPSR

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A new series of Schiff's base compounds were synthesized by condensation of 1-(4-amino-4 phenyl) 3-phenyl triazene-1-ol) and substituted aldehyde and gave high yields of target compounds. Antimicrobial activity of compounds has been tested against bacterial and fungal species, namely gram-positive bacteria as S. aureus and S. pyogenes, gram-negative bacteria as E. coli and P. aeruginosa, and fungal species C. albicans and A. clavatus are selected based on their clinical and pharmacological importance. Bacterial and fungal tests were performed under the same conditions using Cefixime and Griseofulvin as standard drugs. It has been found that synthesized Schiff's base has shown efficient antibacterial and anti-fungal activities. Thus they can be revealed as potent antimicrobial compounds. They are widely used for industrial purposes and also exhibit a broad range of biological activities. The structures of synthesized compounds were confirmed by TLC, melting point, Infrared spectroscopy, and proton nuclear magnetic resonance spectroscopy ( 1 HNMR) data.

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Synthesis and Characterization of Citral-Methylanthranilate Schiff Base, Relationship Between Synthesis Time and Some Physical Properties

Cited by 3 publications

References 12 publications

Controlled Lactonization of o-Coumaric Esters Mediated by Supramolecular Gels

Controlled Lactonization of o-Coumaric Esters Mediated by Supramolecular Gels

Controlled Hydrolysis of Odorants Schiff Bases in Low-Molecular-Weight Gels

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