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Characteristics of Langmuir monomolecular monolayers formed by the novel oil blends

  • Wiktoria Kamińska ORCID logo , Wojciech Cichocki ORCID logo , Hanna Maria Baranowska ORCID logo , Katarzyna Walkowiak ORCID logo , Dominik Kmiecik ORCID logo and Przemysław Łukasz Kowalczewski ORCID logo EMAIL logo
Published/Copyright: December 19, 2023
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Open Chemistry
From the journal Open Chemistry Volume 21 Issue 1

Abstract

The aim of this work was to assess the physical properties of Langmuir monolayers of three new oil blends “RBWg” (obtained by mixing rapeseed oil, black cumin oil, and wheat germ oil), “REp” (rapeseed oil and evening primrose oil), and “CRb” (camelina oil and rice bran oil), as well as to characterize the molecular dynamics of their protons using low-field nuclear magnetic resonance (LF NMR) method. The studied blends are rich in oleic acid (C18:1), linolenic acid (C18:2), and α-linolenic acid (18:3). The chromatographically determined ratio of n6 to n3 fatty acids was found to be in the range of 5.18–5.27. The appropriate n6/n3 fatty acid ratio was also confirmed by FT-IR analysis. The spin–lattice relaxation rate (R 1) and spin–spin relaxation time (R 2) measured by LF NMR method were similar for the RBWg and REp blends but different from the third oil blend (CRb), which indicates lower proton mobility in CRb. The observed changes in the properties of monolayers of oil blends suggest that the refined rice bran oil in the CRb blend also significantly changes the viscoelastic properties of this blend. The results obtained in this study provide a theoretical basis for the development of a well-balanced approach to using oils in food production technology.

Graphical abstract

Keywords: Langmuir monolayers; physicochemical properties; edible oils; cold-pressed oils; molecular properties of oils; fatty acid profile

1 Introduction

Fats and oils play a crucial role in the human diet, providing essential nutrients and contributing to overall health. For individuals adhering to plant-based diets, oils become even more critical in meeting nutritional requirements, particularly for essential fatty acids (EFAs) that the body cannot synthesize on its own [1]. EFAs are a subset of polyunsaturated fatty acids that are essential for the human body’s proper functioning. Two main types of EFAs are linoleic acid (LA), an n6 fatty acid, and α-linolenic acid (ALA), an n3 fatty acid [2]. Omega-6 fatty acids are abundant in various plant-based oils, such as soybean oil, sunflower oil, and safflower oil. On the other hand, n3 fatty acids are primarily found in flaxseed oil, chia seed oil, and canola oil. While some plants like algae and seaweed contain long-chain n3 fatty acids like eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), they are relatively scarce in most plant-based oils. Thus, it is essential for vegans and vegetarians to be mindful of their n3 intake. An ideal diet should maintain a balanced ratio of n6 to n3 fatty acids. Historically, human diets had a ratio close to 1:1 or 2:1 [3]; however, modern Western diets have shifted to a much higher ratio, often reaching 15:1 or even 20:1, primarily due to the increased consumption of processed foods and vegetable oils rich in n6 fatty acids [4,5]. A high n6 to n3 ratio has been associated with inflammation and various chronic health conditions.

Plant-based diets are becoming increasingly popular, especially among younger individuals. Maintaining a balanced n6/n3 ratio in these diets is of growing importance. In diets based on plant raw materials, the availability of DHA and EPA is minimal, potentially leading to adverse health outcomes [2,6,7]. Nevertheless, it is feasible to produce these EFAs through synthesis from their precursor, i.e., ALA [8,9]. Therefore, it is important to ensure an adequate supply of ALA for vegans and vegetarians, which may be an important factor in preventing n3 fatty acid deficiencies due to the exclusion of marine sources of these fatty acids [10]. Vegan and vegetarian diets may already contain an abundance of n6 fatty acids from plant-based oils, so it becomes crucial to incorporate sources of ALA-rich sources to help balance the ratio [2,6,11]. By incorporating a variety of plant-based oils and being mindful of n6 to n3 ratios, individuals can meet their nutritional needs while enjoying the many benefits oils offer. A well-balanced approach to using oils in a plant-based diet can contribute to overall health and well-being.

The fundamental understanding of the physical properties of edible oils is pivotal for comprehending their diverse roles in the realm of food production. From deep-frying to baking and salad dressings, the unique physical characteristics of edible oils significantly influence the texture, taste, and overall quality of numerous culinary creations [12,13,14]. While the chemical composition of edible oils has been extensively studied, the intricate interplay between their physical properties and technological applications continues to be a subject of intense scientific exploration. Previous studies analyzed the behavior of various oil blends during thermal treatment [15,16] and selected the three most favorable ones, which were further encapsulated in yeast cells [17]. However, it turned out that different oil blends have different properties and encapsulation efficiency. This may be related to their molecular and surface properties; therefore, this work is a report of the physical properties of monolayers of new blends of vegetable oils, as well as to characterize the molecular dynamics of their protons using low-field nuclear magnetic resonance (LF NMR) method.

2 Materials and methods

2.1 Raw materials and blends preparation

The basic materials analyzed in this study were three oil blends prepared using cold pressed oils (rapeseed oil, black cumin oil, wheat germ oil, evening primrose oil, and flaxseed oil) and refined rice bran oil. All oils used in the study were purchased directly from the manufacturer. The cold pressed oils were purchased from Semco Sp.z o.o. Sp.k., Śmiłowo, Poland), while the rice bran oil was purchased from Kasisuri Group (Bangkok, Thailand). The oil blends were prepared by mixing the oils in the specified proportions (Table 1). Briefly, oils were measured by volume, sealed in a dark bottle under a nitrogen atmosphere, and mixed for 1 h. The prepared blends were stored at 5°C until analysis.

Table 1

Percentages of oils constituting the analyzed blends

Code Type of oil Share (%)
RBWg Rapeseed oil Black cumin oil Wheat germ oil 50 30 20
REp Rapeseed oil Evening primrose oil 65 35 —
CRb Camelina oil Rice bran oil 12 88 —

2.2 Fatty acid composition

To determine the fatty acid composition, the procedure described in the international standard AOCS Ce 1h-05 was used [18]. Briefly, the oil was dissolved in hexane, and transesterified with sodium methylate. The obtained fatty acid methyl esters were analyzed using an Agilent 7890A gas chromatograph equipped with a flame ionization detector (FID) (Agilent Technologies, Santa Clara, CA, USA) and Zebron ZB-WAX Plus column (Phenomenex, Torrance, CA, USA) (30 m, 0.25 mm, 1 µm). The GC conditions were as follows: oven temperature was initially 60°C and increased to 240°C at 2°C/min; injector and detector temperatures were 250°C; split ratio 1:10; carrier gas was helium at 3 mL/min.

2.3 Fourier transform infrared (FT-IR) spectroscopy

Infrared spectra were gathered using a Perkin Elmer spectrophotometer (Waltham, MA, USA), which was equipped with an ATR device featuring a diamond as its internal reflection element in the spectral range of 4,000–400 cm−1 [19].

2.4 LF NMR study

The relaxation times spin-lattice T 1 and spin–spin T 2 were measured by using the pulse NMR spectrometer PS15T (Ellab, Poznań, Poland) operating at 15 MHz. The inversion-recovery (π−τ−π/2) pulse sequence was applied for the T 1 relaxation times. Distance (t) between pulses were changed of 0.2–400 ms. The repetition time was 20 s. Each time, 32 free induction decay signals (FID) and 119 points from each FID were collected. Calculations of the T 1 values were performed using the CracSpin software [20]. The CPMG pulse sequence (π/2−τ−(π) n ) was applied to measured T 2. The distance between π pulses were 1 ms or 2 ms depending on the samples. The tree signal accumulations were applied and the repetition time was 15 s. The calculations of the T 2 were performed with the dedicated PS15T software involving non-linear last square algorithm. The T 1 and T 2 values were calculated with standard deviation. All measurements were performed at controlled temperature of 20.0 ± 0.5°C. The R 1 and R 2 relaxation rates were obtained as the reciprocals of the measured spin-lattice and spin–spin relaxation times.

2.5 Creation of a monolayer at air–water interface

In order to study the monolayers formed by the tested oil mixtures, a Langmuir bath (KN 2002, KSV NIMA, Helsinki, Finland) was used. Monolayers of oil mixtures were compressed with hydrophilic moving barriers on a Teflon bath. During the measurement, the dependence of the change in surface pressure π on the area per single molecule A (π-A isotherm) was recorded using a Wilhelmy plate with a highly porous surface, hooked onto an electronic balance. The π-A isotherm was recorded at least three times each to confirm its repeatability. Before starting the measurement, the bath and barriers were thoroughly cleaned with a dust-free wipe (from KIMTECH) soaked in chloroform. Afterwards, the bath was filled with ultrapure deionized water with a resistivity of 18.2 MΩ × cm, which acted as a carrier phase. To prepare the solutions, we used chloroform of 99.8% purity (POCH, Lublin, Poland). The test substance was applied to the surface of the carrier phase using a glass microsyringe (Hamilton, Company, Reno, NV, USA). The barriers are slid down at a constant speed of 5 mm/min after waiting for a time needed for the solvent to evaporate (15 min). During the measurement, a constant subphase temperature (20°C) is maintained by a Julabo thermostat (Julabo GmbH, Seelbach, Germany). To ensure proper process conditions, the system was placed in a laminar chamber. In addition, the system is isolated from external vibrations by the VarioControl active anti-vibration system (Halcyonics GmbH, Göttingen, Germany).

2.6 Oscillatory barrier experiment

The dilatation viscoelasticity of Langmuir layers was studied using the oscillatory barrier method. During the experiment, the changes in surface pressure caused by putting the barriers into oscillatory motion of a certain frequency and amplitude are recorded. The monolayers were compressed to the corresponding surface pressure and allowed to relax for 20 min. The barriers then began to oscillate at a frequency of 0.1 Hz, inducing small changes in amplitude (5%). At least five cycles of oscillation were performed, with a time interval of 60 s between each cycle.

3 Results and discussion

3.1 Chemical composition

The levels of major fatty acids, saturated fats (SFA), monounsaturated fats, and polyunsaturated fats (PUFA) as well as n6/n3 and SFA/PUFA ratios in oils and blends are presented in Figure 1. The prevailing fatty acids identified were oleic acid (C18:1, n9), LA (C18:2, n6), and ALA (C18:3, n3). Evening primrose oil had the highest n6 fatty acid content, reaching the n6/n3 ratio of 295 ± 6. The second highest value of this ratio index was found in black cumin oil (235 ± 5). However, the obtained oil blends were characterized by a balanced ratio of n6 to n3 acids within the range of 5.18–5.27. There are presently no universally agreed-upon guidelines concerning the intake of n6 and n3 fatty acids. Recommendations for various population groups differ depending on the country and dietary patterns. The World Health Organization/Food and Agriculture Organization has proposed an ideal n6/n3 ratio ranging from 5:1 to 10:1 [21], but various national organizations often provide disparate guidance on this matter. On the other hand, n3 fatty acids play a role in regulating prostaglandin metabolism and reducing triglyceride levels. When consumed in high quantities, they effectively reduce cholesterol and possess anticoagulant and anti-inflammatory properties as well [5].

Figure 1 Fatty acids compositions and n6/n3 and SFA/PUFA ratios of oil blends.
Figure 1

Fatty acids compositions and n6/n3 and SFA/PUFA ratios of oil blends.

3.2 FT-IR spectroscopy

Figure 2 shows the infrared spectrum of oil mixtures in the fundamental infrared range. Infrared spectroscopy did not show any spectral changes between the tested oil blends, which is confirmed by the chromatographically determined ratio of n6 to n3 fatty acids of 5:1.

Figure 2 FT-IR spectra of analyzed oil blends.
Figure 2

FT-IR spectra of analyzed oil blends.

The FT-IR spectrum showed two strong bands at the wave number of 2,900 and 1,718 cm−1, which we can attribute to the Alkanes C═H stretch and the bands related to the –C–O group of ester fatty acids [22]. Bands originating from the C–C(═O)–O vibrations of saturated esters are visible in the range of 1,240–1,100 cm−1. However, the band for 1,400 cm−1 attributes to the vibrations of the methyl groups of the aliphatic chain [23]. Another high band at 1,150 cm−1 confirms the presence of stretching and bending vibrations –C–O, –CH2 (Table 2). Properly composed oil blends, with similar characteristics of the n6/n3 fatty acid ratio, may have different physical and technological properties due to the different ingredients that constitute them. Therefore, further analyzes were performed to characterize the analyzed blends.

Table 2

Distribution of absorption bands characteristic of vegetable oils

Range (cm−1) Functional group Mode of vibration
3,477–3,468 –C═0 Ester
3,030–2,994 ═C–H (trans) Stretching
═C–H (cis)
2,994–2,800 –C═H Stretching
–C–H (CH2) Stretching (asym)
2,884–2,751 –C–H (CH2) Stretching (sym)
1,861–1,623 –C═O Stretching
1,497–1,404 –C–H (CH2) Bending
1,389–1,338 –C–H (CH3) Bending (sym)
1,326–1,209 –C–O Stretching
–CH2– Bending
1,213–1,126 –C–O Stretching
–CH2– Bending
1,113–1,086 –C–O Stretching
784–648 –O–H Bending

3.3 LF NMR relaxometry

Pulse techniques allow for the dynamic characterization of protons of the tested biological material. Literature data indicate that if the only manifestation of molecular dynamics are the movements of molecules or groups of molecules that are carriers of resonating protons, LF NMR analysis involves measuring the spin-lattice (T 1) and spin–spin (T 2) relaxation times [24,25]. After the proton system is excited by an electromagnetic field pulse, energy is absorbed. After turning off the pulse, the excited proton spins return to equilibrium. This effect can be achieved by transferring energy from the excited system to the surroundings. The kinetics of this process is called longitudinal relaxation and the speed at which this process occurs determines the R 1 relaxation rate. The process related to the interactions of nuclear spins involves the disappearance of transverse magnetization [26,27]. This process depends on two factors: the heterogeneity of the magnetic field B 0 and the interactions of variable local magnetic fields. The rate of energy transfer in this process, described by the spin–spin relaxation rate R 2, determines the internal parameters and physicochemical properties of the sample. The higher the spin–spin relaxation rate R 2, the more ordered the system. However, the spin-lattice relaxation rate R 1 has minimum values for both liquid and solid systems. Therefore, when analyzing the molecular dynamics of systems, it is necessary to refer to both the spin-lattice and spin–spin relaxation rates and consider them together, especially when the examined material is ambiguously ordered.

The tested oil blends are a mixture of various oils, as described in Table 1. It was found that RBWg and CRb blends are characterized by similar, but lower than REp, spin–spin relaxation rate (R 2) values (Table 3). This proves that the structures of fatty acid chains in RBWg and CRb are less organized. The greater ordering of structure of REp is confirmed by the experimentally obtained value of the spin-lattice relaxation rate (R 1), which is the smallest for this blend. It can be assumed that these properties are determined by rice brain oil, because the blend contains as much as 88% of this oil.

Table 3

LF NMR study results of analyzed oil blends

Oil blend R 1 (1/s) R 2 (1/s) Mean correlation time τ c (s)
RBWg 8.65 ± 0.03 17.61 ± 1.18 7.2 × 10−9
Rep 9.44 ± 0.03 18.84 ± 0.82 7.1 × 10−9
CRb 8.24 ± 0.02 23.00 ± 2.34 10.1 × 10−9

RBWg and REp oil blends contain 50 and 65% rapeseed oil, respectively, and the spin–spin relaxation rates of both samples are slightly different (17.61 and 18.84 s−1). This means that the rapeseed oil determines the dynamic properties of protons in spin–spin interactions. The analysis of the spin-lattice relaxation rate values indicates much smaller differences in the R 1 values of the RBWg and REp blends (8.65 and 9.44 s−1, respectively) than in the R 2 values for these samples. Therefore, it should be stated that the molecular dynamics of protons in these blends is characteristic of systems with less structural order. In liquids, an increase in the value of the spin-lattice relaxation rate is observed with the increase in the viscosity. In some cases, the R 1 values reach a maximum, and then, with a further increase in viscosity, a decrease in the value of the spin-lattice relaxation rate is observed. The spin–spin relaxation rate R 2 monotonically increases from small values, characteristic of low viscosity liquids, to large values determined by interactions in solids characterized by a rigid, ordered structure [28].

The results of relaxation time measurements were used to determine the mean correlation time of the protons [16,29,30]. The higher the mean correlation time value, the more molecularly ordered the analyzed system is. It was found that CRb is characterized by approximately 41% higher mean correlation time than the other two oil blends (Table 3), which indicates lower proton mobility. This can be explained as a result of the presence of rice bran oil in the system, which was the only oil among those used to obtain the blends that was refined [31]. Therefore, the use of refined oils as ingredients of blends, along with cold-pressed oils, significantly affects the molecular dynamics of the resulting blend. Due to the low water content in refined oils (compared to cold-pressed ones), as well as the low content of other compounds, such as chlorophylls or tocopherols, refined oils determine the properties of oil blends determined by the LF NMR method.

3.4 Characterization of Langmuir monolayers formed by oil blends

In the following work, blends of oils rich in fatty acids with an amphiphilic structure were examined. Hydrophilic polar groups absorb on the surface of the carrier phase when the hydrocarbon chain orients vertically, forming a tightly packed layer. In the work of Langmuir, Pockels, and Rayleigh on the layers formed by fatty acids, it was shown that acids with different chain lengths occupy a similar surface area per single molecule of about 20 A2 [32,33,34,35].

3.4.1 π-A isotherms

Recorded isotherms of the change in surface pressure (π) as a function of the surface area per molecule of the individual blends and their components are shown in Figure 3. In addition, parameters were determined from the course of the curve, i.e., surface pressure (π c), average surface area available for a single molecule (A c) at the point of refraction of the layer, average surface area available for a single molecule at the time of increase in surface pressure (A 0), average value of the surface area per single molecule in a tightly packed monolayer (A ex), which are characteristic of Langmuir monolayers formed by the tested substances. The values obtained are summarized in Table 4.

Figure 3 (a) π-A isotherms and (b) compressibility module registered for the tested blends.
Figure 3

(a) π-A isotherms and (b) compressibility module registered for the tested blends.

Table 4

Parameters determined from the course of the isotherms

Oil blend A ex (A2) A c (A2) Π c (mN/m)
RBWg 43.10 ± 0.01 12.95 ± 0.01 17.57 ± 0.01
REp 39.15 ± 0.01 16.33 ± 0.01 15.71 ± 0.01
CRb 41.87 ± 0.01 23.67 ± 0.01 14.24 ± 0.01

The molecules of all the studied compounds form an insoluble monomolecular layer, as evidenced by the obtained π-A isotherms and the readout values of the parameters characterizing the layer. This means that the layer-forming molecules are essentially insoluble in the water subphase and at the interface, when compressed, are able to form two-dimensional layers. As the monolayer is compressed, the molecules begin to orient themselves relative to each other. The orientation of the molecules strongly depends on their chemical structure. In the initial stage of compression, the layer exists in a state of two-phase coexistence. As a result of further compression of the monolayer, the distance between the molecules decreases and at the same time the strength of their interactions increases. On the π-A isotherm, a monotonic increase in the value of surface pressure is observed, which leads to the transition to the condensed liquid phase. Depending on the compound under study, the area of increase in surface pressure takes place at a different value of surface area per single molecule. The transition begins with the extrapolated average molecular area A ex (Table 4), which increases with the number of double bonds present in a hydrocarbon chain having the same number of carbon atoms. Subsequent compression results in the appearance of a phase transition to the solid state. Finally, the Langmuir monolayer collapses. The collapse of the monolayer occurs at the characteristic surface pressure π c, the determined values for the tested mixtures are summarized in Table 4. Differences between the observed values of π c are due to the number of double bonds in the hydrocarbon chain. An increase in the unsaturation of aliphatic chains affects the reduced stability of the layers formed, which is observed for the blends studied. The highest value of π c is achieved by the RBWg blend (17.7 mN/m), which shows that among all the blends tested, it forms the most stable layer. In the case of layers formed by blends after the collapse, there is a decrease in surface pressure. The studied oil mixtures are rich in oleic acid (C18:1), LA (C18:2), palmitic acid (C16:0), and ALA (18:3). Comparing the obtained course of recorded π-A isotherms with the literature, we note that it is similar to that recorded for the acids that predominate in the studied mixtures (C18:1 and C18:2 acids). The combination of individual oils causes an increase in unsaturated chains, which increases the area occupied by the studied molecules at the interface. In addition, it was noted that an increase in the length of the apolar chain for molecules with the same number of double bonds affects the increase in the surface area per single molecule, which was previously observed in studies devoted to fatty acids [36,37,38,39,40,41]. The influence of the double bond directly affects the position of molecules at the water/air interface.

Use of the recorded values and equation (1) (Supplementary Materials) was used to determine the compressibility coefficient Cs−1 shown in Figure 3. The Davies and Rideal criterion specifies that the liquid expanded state is characterized by modulus values between 12.5 and 50 mN/m, while the liquid condensed state takes on values between 100 and 250 mN/m. Moreover, Cs−1 values in the range of 0–12.5 mN/m indicate the gas phase, 50–100 mN/m indicate the liquid phase, while above 250 mN/m we are dealing with the solid phase [36,37,38,39,40]. The maximum value of Cs−1 corresponds to the state in which the layer is most compressed. The highest determined value of the compressibility modulus is observed for the blends RBWg (119.40 mN/m) and REp (100.02 mN/m), which take values above 100 mN/m, indicating that both blends form a layer in the liquid condensed phase. On the other hand, the Cs−1 MAX value recorded for the CRb blend is 71.25 mN/m, which indicates the formation of a layer in the liquid phase. Based on the recorded values, it is clear that the RBWg mixture forms the most elastic monolayer during compression of the compound on the subphase surface. The observed decrease in the value of the compressibility modulus is due to the increase in unsaturation in the hydrocarbon chain, which has the greatest impact on this value for the CRb mixture.

3.4.2 Intermolecular interactions

In order to determine the type of possible interactions between molecules of blends of oils which are two- and three-component systems, the redundant surface An was determined (equation (3), Supplementary Materials). If An takes values greater than zero, then the interactions are repulsive. However, if An is less than zero, then the interactions are attractive. This indicates that the attractive forces between components in the monolayer are stronger than those acting between molecules in pure compounds [42,43]. The determined values of the redundant area are shown in Table 5.

Table 5

Determined values of the redundant surface An

Oil blend An (A2)
RBWg 19.3 ± 0.8
REp −0.384 ± 0.012
CRb −1.25 ± 0.26

The redundant surface area values for most mixtures are negative (REp and CRb), which indicates the attractive nature of the interactions between the molecules. In the case of the RBWg mixture (19.3 A2), the excess area values become positive, indicating the repulsive nature of the interactions.

3.4.3 Rheological properties

The important properties of interfacial layers are dilatation viscoelasticity and shear viscoelasticity. Based on measurements of the dynamic elasticity of the formed monolayers, the surface elasticity modulus ε is determined and presented in Table 6.

Table 6

Determined values of the modulus of viscoelastic properties

Oil blend ε MAX (mN/m) Cs−1 MAX (mN/m)
RBWg 112.1 ± 3.2 119.1 ± 3.0
REp 94.2 ± 1.0 100.0 ± 1.2
CRb 62.5 ± 0.4 71.5 ± 0.6

Depending on the value of surface elasticity, the recorded surface pressure can be divided into three zones. In the first zone, when the dynamic elasticity does not exceed 50 mN/m, long-range forces lead to the formation of a regular structure with distances between particles larger than their diameter. Further oscillatory motion of the barriers causes them to exceed the long-range repulsion forces, and the particles are more closely packed. In this zone, the value of ε can reach values from 50 to 250 mN/m. Surface elasticity values in this range are observed for all mixtures tested. The third zone, corresponding to ε values above 250 mN/m, is characterized by high compression and a closely packed monolayer [41]. We observed that the values of ε (describing the dynamic elasticity of the layer surface determined by the oscillatory barrier method), compared with the values of the compressibility modulus Cs−1 (which is a measure of the elasticity of the formed layer during compression) for all the tested oil blends, are not significantly different from each other, which means that the adsorbed molecules form an elastic monolayer at the interface.

4 Conclusion

The use of oils with appropriate nutritional value is crucial from the point of view of nutritional value, but appropriate composition of oil blends allows you to obtain blends with a much higher nutritional value than pure oils. The analyses of the newly developed oil blends indicate that despite the lack of differences in the chromatographically determined n6/n3 acid ratios, also confirmed by the FT-IR method, they differ significantly from the molecular point of view. The use of refined oil from which water has been removed in the blend causes the fatty acid chains to become stiffer. This is manifested by an increase in the mean correlation time and the largest viscoelastic modulus. It was also found that the oil constituting the largest share in the blend determines the properties of the obtained blend, which was also observed in the results obtained from the analysis of the properties of the monolayer. When designing new oil blends, it is worth approaching this issue holistically, because not only the chemical composition itself, but even the method of obtaining the oils significantly affects the physical properties of the obtained blends. The obtained results constitute a starting point for further research that can improve our knowledge about the influence of the viscoelastic properties of oils on the ability to transport blends through biological membranes.

# These authors contributed equally.

  1. Funding information: The National Centre for Research and Development of Poland (NCBR) is acknowledged for funding provided within the program LIDER under grant agreement No. LIDER/27/0105/L-11/19/NCBR/2020 (PI: Przemysław Kowalczewski).

  2. Author contributions: W.K: investigation, methodology, and writing – original draft; W.C.: data curation, investigation, methodology, and writing – original draft; H.M.B.: investigation and methodology; K.W.: investigation; D.K.: visualization; P.Ł.K.: conceptualization, data curation, formal analysis, funding acquisition, methodology, project administration, supervision, validation, writing – original draft, and writing – review and editing.

  3. Conflict of interest: The authors declare no conflict of interest.

  4. Ethical approval: The conducted research is not related to either human or animal use.

  5. Data availability statement: The datasets generated during and/or analyzed during the current study are available from the corresponding author on reasonable request.

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Received: 2023-10-25
Revised: 2023-11-21
Accepted: 2023-11-28
Published Online: 2023-12-19

© 2023 the author(s), published by De Gruyter

This work is licensed under the Creative Commons Attribution 4.0 International License.

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https://doi.org/10.1515/chem-2023-0173
Keywords for this article
Langmuir monolayers; physicochemical properties; edible oils; cold-pressed oils; molecular properties of oils; fatty acid profile
Creative Commons
BY 4.0

Articles in the same Issue

  1. Characteristics, source, and health risk assessment of aerosol polyaromatic hydrocarbons in the rural and urban regions of western Saudi Arabia
  2. Regular Articles
  3. A network-based correlation research between element electronegativity and node importance
  4. Pomegranate attenuates kidney injury in cyclosporine-induced nephrotoxicity in rats by suppressing oxidative stress
  5. Ab initio study of fundamental properties of XInO3 (X = K, Rb, Cs) perovskites
  6. Responses of feldspathic sandstone and sand-reconstituted soil C and N to freeze–thaw cycles
  7. Robust fractional control based on high gain observers design (RNFC) for a Spirulina maxima culture interfaced with an advanced oxidation process
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  11. Characterization of effective constituents in Acanthopanax senticosus fruit for blood deficiency syndrome based on the chinmedomics strategy
  12. Comparative analysis of the metabolites in Pinellia ternata from two producing regions using ultra-high-performance liquid chromatography–electrospray ionization–tandem mass spectrometry
  13. The assessment of environmental parameter along the desalination plants in the Kingdom of Saudi Arabia
  14. Effects of harpin and carbendazim on antioxidant accumulation in young jujube leaves
  15. The effects of in ovo injected with sodium borate on hatching performance and small intestine morphology in broiler chicks
  16. Optimization of cutting forces and surface roughness via ANOVA and grey relational analysis in machining of In718
  17. Essential oils of Origanum compactum Benth: Chemical characterization, in vitro, in silico, antioxidant, and antibacterial activities
  18. Translocation of tungsten(vi) oxide/gadolinium(iii) fluoride in tellurite glasses towards improvement of gamma-ray attenuation features in high-density glass shields
  19. Mechanical properties, elastic moduli, and gamma ray attenuation competencies of some TeO2–WO3–GdF3 glasses: Tailoring WO3–GdF3 substitution toward optimum behavioral state range
  20. Comparison between the CIDR or sponge with hormone injection to induce estrus synchronization for twining and sex preselection in Naimi sheep
  21. Exergetic performance analyses of three different cogeneration plants
  22. Psoralea corylifolia (babchi) seeds enhance proliferation of normal human cultured melanocytes: GC–MS profiling and biological investigation
  23. A novel electrochemical micro-titration method for quantitative evaluation of the DPPH free radical scavenging capacity of caffeic acid
  24. Comparative study between supported bimetallic catalysts for nitrate remediation in water
  25. Persicaline, an alkaloid from Salvadora persica, inhibits proliferation and induces apoptosis and cell-cycle arrest in MCF-7 cells
  26. Determination of nicotine content in locally produced smokeless tobacco (Shammah) samples from Jazan region of Saudi Arabia using a convenient HPLC-MS/MS method
  27. Changes in oxidative stress markers in pediatric burn injury over a 1-week period
  28. Integrated geophysical techniques applied for petroleum basins structural characterization in the central part of the Western Desert, Egypt
  29. The impact of chemical modifications on gamma-ray attenuation properties of some WO3-reinforced tellurite glasses
  30. Microwave and Cs+-assisted chemo selective reaction protocol for synthesizing 2-styryl quinoline biorelevant molecules
  31. Structural, physical, and radiation absorption properties of a significant nuclear power plant component: A comparison between REX-734 and 316L SS austenitic stainless steels
  32. Effect of Moringa oleifera on serum YKL-40 level: In vivo rat periodontitis model
  33. Investigating the impact of CO2 emissions on the COVID-19 pandemic by generalized linear mixed model approach with inverse Gaussian and gamma distributions
  34. Influence of WO3 content on gamma rays attenuation characteristics of phosphate glasses at low energy range
  35. Study on CO2 absorption performance of ternary DES formed based on DEA as promoting factor
  36. Performance analyses of detonation engine cogeneration cycles
  37. Sterols from Centaurea pumilio L. with cell proliferative activity: In vitro and in silico studies
  38. Untargeted metabolomics revealing changes in aroma substances in flue-cured tobacco
  39. Effect of pumpkin enriched with calcium lactate on iron status in an animal model of postmenopausal osteoporosis
  40. Energy consumption, mechanical and metallographic properties of cryogenically treated tool steels
  41. Optimization of ultra-high pressure-assisted extraction of total phenols from Eucommia ulmoides leaves by response surface methodology
  42. Harpin enhances antioxidant nutrient accumulation and decreases enzymatic browning in stored soybean sprouts
  43. Physicochemical and biological properties of carvacrol
  44. Radix puerariae in the treatment of diabetic nephropathy: A network pharmacology analysis and experimental validation
  45. Anti-Alzheimer, antioxidants, glucose-6-phosphate dehydrogenase effects of Taverniera glabra mediated ZnO and Fe2O3 nanoparticles in alloxan-induced diabetic rats
  46. Experimental study on photocatalytic CO2 reduction performance of ZnS/CdS-TiO2 nanotube array thin films
  47. Epoxy-reinforced heavy metal oxides for gamma ray shielding purposes
  48. Black mulberry (Morus nigra L.) fruits: As a medicinal plant rich in human health-promoting compounds
  49. Promising antioxidant and antimicrobial effects of essential oils extracted from fruits of Juniperus thurifera: In vitro and in silico investigations
  50. Chloramine-T-induced oxidation of Rizatriptan Benzoate: An integral chemical and spectroscopic study of products, mechanisms and kinetics
  51. Study on antioxidant and antimicrobial potential of chemically profiled essential oils extracted from Juniperus phoenicea (L.) by use of in vitro and in silico approaches
  52. Screening and characterization of fungal taxol-producing endophytic fungi for evaluation of antimicrobial and anticancer activities
  53. Mineral composition, principal polyphenolic components, and evaluation of the anti-inflammatory, analgesic, and antioxidant properties of Cytisus villosus Pourr leaf extracts
  54. In vitro antiproliferative efficacy of Annona muricata seed and fruit extracts on several cancer cell lines
  55. An experimental study for chemical characterization of artificial anterior cruciate ligament with coated chitosan as biomaterial
  56. Prevalence of residual risks of the transfusion-transmitted infections in Riyadh hospitals: A two-year retrospective study
  57. Computational and experimental investigation of antibacterial and antifungal properties of Nicotiana tabacum extracts
  58. Reinforcement of cementitious mortars with hemp fibers and shives
  59. X-ray shielding properties of bismuth-borate glass doped with rare earth ions
  60. Green supported silver nanoparticles over modified reduced graphene oxide: Investigation of its antioxidant and anti-ovarian cancer effects
  61. Orthogonal synthesis of a versatile building block for dual functionalization of targeting vectors
  62. Thymbra spicata leaf extract driven biogenic synthesis of Au/Fe3O4 nanocomposite and its bio-application in the treatment of different types of leukemia
  63. The role of Ag2O incorporation in nuclear radiation shielding behaviors of the Li2O–Pb3O4–SiO2 glass system: A multi-step characterization study
  64. A stimuli-responsive in situ spray hydrogel co-loaded with naringenin and gentamicin for chronic wounds
  65. Assessment of the impact of γ-irradiation on the piperine content and microbial quality of black pepper
  66. Antioxidant, sensory, and functional properties of low-alcoholic IPA beer with Pinus sylvestris L. shoots addition fermented using unconventional yeast
  67. Screening and optimization of extracellular pectinase produced by Bacillus thuringiensis SH7
  68. Determination of polyphenols in Chinese jujube using ultra-performance liquid chromatography–mass spectrometry
  69. Synergistic effects of harpin and NaCl in determining soybean sprout quality under non-sterile conditions
  70. Field evaluation of different eco-friendly alternative control methods against Panonychus citri [Acari: Tetranychidae] spider mite and its predators in citrus orchards
  71. Exploring the antimicrobial potential of biologically synthesized zero valent iron nanoparticles
  72. NaCl regulates goldfish growth and survival at three food supply levels under hypoxia
  73. An exploration of the physical, optical, mechanical, and radiation shielding properties of PbO–MgO–ZnO–B2O3 glasses
  74. A novel statistical modeling of air pollution and the COVID-19 pandemic mortality data by Poisson, geometric, and negative binomial regression models with fixed and random effects
  75. Treatment activity of the injectable hydrogels loaded with dexamethasone In(iii) complex on glioma by inhibiting the VEGF signaling pathway
  76. An alternative approach for the excess lifetime cancer risk and prediction of radiological parameters
  77. Panax ginseng leaf aqueous extract mediated green synthesis of AgNPs under ultrasound condition and investigation of its anti-lung adenocarcinoma effects
  78. Study of hydrolysis and production of instant ginger (Zingiber officinale) tea
  79. Novel green synthesis of zinc oxide nanoparticles using Salvia rosmarinus extract for treatment of human lung cancer
  80. Evaluation of second trimester plasma lipoxin A4, VEGFR-1, IL-6, and TNF-α levels in pregnant women with gestational diabetes mellitus
  81. Antidiabetic, antioxidant and cytotoxicity activities of ortho- and para-substituted Schiff bases derived from metformin hydrochloride: Validation by molecular docking and in silico ADME studies
  82. Antioxidant, antidiabetic, antiglaucoma, and anticholinergic effects of Tayfi grape (Vitis vinifera): A phytochemical screening by LC-MS/MS analysis
  83. Identification of genetic polymorphisms in the stearoyl CoA desaturase gene and its association with milk quality traits in Najdi sheep
  84. Cold-acclimation effect on cadmium absorption and biosynthesis of polyphenolics, and free proline and photosynthetic pigments in Spirogyra aequinoctialis
  85. Analysis of secondary metabolites in Xinjiang Morus nigra leaves using different extraction methods with UPLC-Q/TOF-MS/MS technology
  86. Nanoarchitectonics and performance evaluation of a Fe3O4-stabilized Pickering emulsion-type differential pressure plugging agent
  87. Investigating pyrolysis characteristics of Shengdong coal through Py-GC/MS
  88. Extraction, phytochemical characterization, and antifungal activity of Salvia rosmarinus extract
  89. Introducing a novel and natural antibiotic for the treatment of oral pathogens: Abelmoschus esculentus green-formulated silver nanoparticles
  90. Optimization of gallic acid-enriched ultrasonic-assisted extraction from mango peels
  91. Effect of gamma rays irradiation in the structure, optical, and electrical properties of samarium doped bismuth titanate ceramics
  92. Combinatory in silico investigation for potential inhibitors from Curcuma sahuynhensis Škorničk. & N.S. Lý volatile phytoconstituents against influenza A hemagglutinin, SARS-CoV-2 main protease, and Omicron-variant spike protein
  93. Physical, mechanical, and gamma ray shielding properties of the Bi2O3–BaO–B2O3–ZnO–As2O3–MgO–Na2O glass system
  94. Twofold interpenetrated 3D Cd(ii) complex: Crystal structure and luminescent property
  95. Study on the microstructure and soil quality variation of composite soil with soft rock and sand
  96. Ancient spring waters still emerging and accessible in the Roman Forum area: Chemical–physical and microbiological characterization
  97. Extraction and characterization of type I collagen from scales of Mexican Biajaiba fish
  98. Finding small molecular compounds to decrease trimethylamine oxide levels in atherosclerosis by virtual screening
  99. Prefatory in silico studies and in vitro insecticidal effect of Nigella sativa (L.) essential oil and its active compound (carvacrol) against the Callosobruchus maculatus adults (Fab), a major pest of chickpea
  100. Polymerized methyl imidazole silver bromide (CH3C6H5AgBr)6: Synthesis, crystal structures, and catalytic activity
  101. Using calcined waste fish bones as a green solid catalyst for biodiesel production from date seed oil
  102. Influence of the addition of WO3 on TeO2–Na2O glass systems in view of the feature of mechanical, optical, and photon attenuation
  103. Naringin ameliorates 5-fluorouracil elicited neurotoxicity by curtailing oxidative stress and iNOS/NF-ĸB/caspase-3 pathway
  104. GC-MS profile of extracts of an endophytic fungus Alternaria and evaluation of its anticancer and antibacterial potentialities
  105. Green synthesis, chemical characterization, and antioxidant and anti-colorectal cancer effects of vanadium nanoparticles
  106. Determination of caffeine content in coffee drinks prepared in some coffee shops in the local market in Jeddah City, Saudi Arabia
  107. A new 3D supramolecular Cu(ii) framework: Crystal structure and photocatalytic characteristics
  108. Bordeaux mixture accelerates ripening, delays senescence, and promotes metabolite accumulation in jujube fruit
  109. Important application value of injectable hydrogels loaded with omeprazole Schiff base complex in the treatment of pancreatitis
  110. Color tunable benzothiadiazole-based small molecules for lightening applications
  111. Investigation of structural, dielectric, impedance, and mechanical properties of hydroxyapatite-modified barium titanate composites for biomedical applications
  112. Metal gel particles loaded with epidermal cell growth factor promote skin wound repair mechanism by regulating miRNA
  113. In vitro exploration of Hypsizygus ulmarius (Bull.) mushroom fruiting bodies: Potential antidiabetic and anti-inflammatory agent
  114. Alteration in the molecular structure of the adenine base exposed to gamma irradiation: An ESR study
  115. Comprehensive study of optical, thermal, and gamma-ray shielding properties of Bi2O3–ZnO–PbO–B2O3 glasses
  116. Lewis acids as co-catalysts in Pd-based catalyzed systems of the octene-1 hydroethoxycarbonylation reaction
  117. Synthesis, Hirshfeld surface analysis, thermal, and selective α-glucosidase inhibitory studies of Schiff base transition metal complexes
  118. Protective properties of AgNPs green-synthesized by Abelmoschus esculentus on retinal damage on the virtue of its anti-inflammatory and antioxidant effects in diabetic rat
  119. Effects of green decorated AgNPs on lignin-modified magnetic nanoparticles mediated by Cydonia on cecal ligation and puncture-induced sepsis
  120. Treatment of gastric cancer by green mediated silver nanoparticles using Pistacia atlantica bark aqueous extract
  121. Preparation of newly developed porcelain ceramics containing WO3 nanoparticles for radiation shielding applications
  122. Utilization of computational methods for the identification of new natural inhibitors of human neutrophil elastase in inflammation therapy
  123. Some anticancer agents as effective glutathione S-transferase (GST) inhibitors
  124. Clay-based bricks’ rich illite mineral for gamma-ray shielding applications: An experimental evaluation of the effect of pressure rates on gamma-ray attenuation parameters
  125. Stability kinetics of orevactaene pigments produced by Epicoccum nigrum in solid-state fermentation
  126. Treatment of denture stomatitis using iron nanoparticles green-synthesized by Silybum marianum extract
  127. Characterization and antioxidant potential of white mustard (Brassica hirta) leaf extract and stabilization of sunflower oil
  128. Characteristics of Langmuir monomolecular monolayers formed by the novel oil blends
  129. Strategies for optimizing the single GdSrFeO4 phase synthesis
  130. Oleic acid and linoleic acid nanosomes boost immunity and provoke cell death via the upregulation of beta-defensin-4 at genetic and epigenetic levels
  131. Unraveling the therapeutic potential of Bombax ceiba roots: A comprehensive study of chemical composition, heavy metal content, antibacterial activity, and in silico analysis
  132. Green synthesis of AgNPs using plant extract and investigation of its anti-human colorectal cancer application
  133. The adsorption of naproxen on adsorbents obtained from pepper stalk extract by green synthesis
  134. Treatment of gastric cancer by silver nanoparticles encapsulated by chitosan polymers mediated by Pistacia atlantica extract under ultrasound condition
  135. In vitro protective and anti-inflammatory effects of Capparis spinosa and its flavonoids profile
  136. Wear and corrosion behavior of TiC and WC coatings deposited on high-speed steels by electro-spark deposition
  137. Therapeutic effects of green-formulated gold nanoparticles by Origanum majorana on spinal cord injury in rats
  138. Melanin antibacterial activity of two new strains, SN1 and SN2, of Exophiala phaeomuriformis against five human pathogens
  139. Evaluation of the analgesic and anesthetic properties of silver nanoparticles supported over biodegradable acacia gum-modified magnetic nanoparticles
  140. Review Articles
  141. Role and mechanism of fruit waste polyphenols in diabetes management
  142. A comprehensive review of non-alkaloidal metabolites from the subfamily Amaryllidoideae (Amaryllidaceae)
  143. Discovery of the chemical constituents, structural characteristics, and pharmacological functions of Chinese caterpillar fungus
  144. Eco-friendly green approach of nickel oxide nanoparticles for biomedical applications
  145. Advances in the pharmaceutical research of curcumin for oral administration
  146. Rapid Communication
  147. Determination of the contents of bioactive compounds in St. John’s wort (Hypericum perforatum): Comparison of commercial and wild samples
  148. Retraction
  149. Retraction of “Two mixed-ligand coordination polymers based on 2,5-thiophenedicarboxylic acid and flexible N-donor ligands: The protective effect on periodontitis via reducing the release of IL-1β and TNF-α”
  150. Topical Issue on Phytochemicals, biological and toxicological analysis of aromatic medicinal plants
  151. Anti-plasmodial potential of selected medicinal plants and a compound Atropine isolated from Eucalyptus obliqua
  152. Anthocyanin extract from black rice attenuates chronic inflammation in DSS-induced colitis mouse model by modulating the gut microbiota
  153. Evaluation of antibiofilm and cytotoxicity effect of Rumex vesicarius methanol extract
  154. Chemical compositions of Litsea umbellata and inhibition activities
  155. Green synthesis, characterization of silver nanoparticles using Rhynchosia capitata leaf extract and their biological activities
  156. GC-MS analysis and antibacterial activities of some plants belonging to the genus Euphorbia on selected bacterial isolates
  157. The abrogative effect of propolis on acrylamide-induced toxicity in male albino rats: Histological study
  158. A phytoconstituent 6-aminoflavone ameliorates lipopolysaccharide-induced oxidative stress mediated synapse and memory dysfunction via p-Akt/NF-kB pathway in albino mice
  159. Anti-diabetic potentials of Sorbaria tomentosa Lindl. Rehder: Phytochemistry (GC-MS analysis), α-amylase, α-glucosidase inhibitory, in vivo hypoglycemic, and biochemical analysis
  160. Assessment of cytotoxic and apoptotic activities of the Cassia angustifolia aqueous extract against SW480 colon cancer
  161. Biochemical analysis, antioxidant, and antibacterial efficacy of the bee propolis extract (Hymenoptera: Apis mellifera) against Staphylococcus aureus-induced infection in BALB/c mice: In vitro and in vivo study
  162. Assessment of essential elements and heavy metals in Saudi Arabian rice samples underwent various processing methods
  163. Two new compounds from leaves of Capparis dongvanensis (Sy, B. H. Quang & D. V. Hai) and inhibition activities
  164. Hydroxyquinoline sulfanilamide ameliorates STZ-induced hyperglycemia-mediated amyleoid beta burden and memory impairment in adult mice
  165. An automated reading of semi-quantitative hemagglutination results in microplates: Micro-assay for plant lectins
  166. Inductively coupled plasma mass spectrometry assessment of essential and toxic trace elements in traditional spices consumed by the population of the Middle Eastern region in their recipes
  167. Phytochemical analysis and anticancer activity of the Pithecellobium dulce seed extract in colorectal cancer cells
  168. Impact of climatic disturbances on the chemical compositions and metabolites of Salvia officinalis
  169. Physicochemical characterization, antioxidant and antifungal activities of essential oils of Urginea maritima and Allium sativum
  170. Phytochemical analysis and antifungal efficiency of Origanum majorana extracts against some phytopathogenic fungi causing tomato damping-off diseases
  171. Special Issue on 4th IC3PE
  172. Graphene quantum dots: A comprehensive overview
  173. Studies on the intercalation of calcium–aluminium layered double hydroxide-MCPA and its controlled release mechanism as a potential green herbicide
  174. Synergetic effect of adsorption and photocatalysis by zinc ferrite-anchored graphitic carbon nitride nanosheet for the removal of ciprofloxacin under visible light irradiation
  175. Exploring anticancer activity of the Indonesian guava leaf (Psidium guajava L.) fraction on various human cancer cell lines in an in vitro cell-based approach
  176. The comparison of gold extraction methods from the rock using thiourea and thiosulfate
  177. Special Issue on Marine environmental sciences and significance of the multidisciplinary approaches
  178. Sorption of alkylphenols and estrogens on microplastics in marine conditions
  179. Cytotoxic ketosteroids from the Red Sea soft coral Dendronephthya sp.
  180. Antibacterial and biofilm prevention metabolites from Acanthophora spicifera
  181. Characteristics, source, and health risk assessment of aerosol polyaromatic hydrocarbons in the rural and urban regions of western Saudi Arabia
  182. Special Issue on Advanced Nanomaterials for Energy, Environmental and Biological Applications - Part II
  183. Green synthesis, characterization, and evaluation of antibacterial activities of cobalt nanoparticles produced by marine fungal species Periconia prolifica
  184. Combustion-mediated sol–gel preparation of cobalt-doped ZnO nanohybrids for the degradation of acid red and antibacterial performance
  185. Perinatal supplementation with selenium nanoparticles modified with ascorbic acid improves hepatotoxicity in rat gestational diabetes
  186. Evaluation and chemical characterization of bioactive secondary metabolites from endophytic fungi associated with the ethnomedicinal plant Bergenia ciliata
  187. Enhancing photovoltaic efficiency with SQI-Br and SQI-I sensitizers: A comparative analysis
  188. Nanostructured p-PbS/p-CuO sulfide/oxide bilayer heterojunction as a promising photoelectrode for hydrogen gas generation
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