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. 2022 Nov 4;7(45):40950–40962. doi: 10.1021/acsomega.2c04102

Investigations to Explore Molecular Interactions and Sweetness Response of Polyhydroxy Compounds with Amino Acids in Aqueous Systems

Muhammad Asghar Jamal †,*, Uzma Shahazidy †, Fatimah A Al-Saeed ‡,○,*, Khalid M Al Syaad §, Majid Muneer †, Ikram Ahmed ∥, Ahmed Ezzat Ahmed §,⊥
PMCID: PMC9670697  PMID: 36406515

Abstract

graphic file with name ao2c04102_0011.jpg

In conjunction with the development of people’s living standards, the modern world demands good-quality food such as sweets, candies, chocolates, diet drinks, beverages, and so on, but because of obesity and other health issues people concentrate more on sugar-free or low-calorie products. Polyols are such a kind of food with desirable qualities, and they play a role in controlling the blood glucose level in diabetic patients. The density (ρ) and sound speed (u) of sugar alcohol in water and in (0.02, 0.04, and 0.06) mol kg–1l-arginine solutions at different temperatures (293.15–318.15 K) and atmospheric pressure were measured by using Anton Paar DSA5000M. Experimental density and sound velocity data were further used to compute volumetric and acoustic parameters such as apparent molar volume (ØV), partial molar volume (ØV0), compressibility (Øk), expansibility (ØE0), and so on. The positive trends of apparent molar volume (ØV), and partial molar volume ØV), values indicate strong hydrophilic interactions in ternary solutions. These interactions give a complete picture about solvation behavior, the effect of temperature, and hydrogen bonding present among (galactitol + l-arginine) mixtures. The apparent specific volume values were calculated, and it was found that these values of the investigated mixtures lie on the borderline with the reported values of sweeteners. This study may offer a new vision in elucidation of mechanistic modifications between sugar alcohol, amino acid, and their mode of interactions.

1. Introduction

Polyhydroxy compounds like carbohydrates and their derivatives (sugar alcohols) carry out numerous functions in biological procedures such as body growth, apoptosis, metabolic regulation, and cryo-preservation.1,2 Polyhydroxy compounds have received excessive consideration because of their preservation abilities in biological systems for preservation of vaccines and use in protein therapy, especially their role in the pharmaceutical and cosmetics industries. In particular, their existence may improve the antioxidant capacity of compounds to some degree.1 Sugar alcohol as galactitol is a sweetener, and its sweetness behavior is about 50–60% like the sweetness of sucrose.3 The interactions of sugar alcohol with model molecules of proteins at different temperatures play a significant role in understanding the nature of action of bioactive molecules and the thermodynamic behavior of the biochemical process in the living organisms.4

Because proteins are particularly macromolecules, it is very difficult to directly study proteins, where amino acids are very appropriate model compounds of proteins. Amino acids are essential chemicals in the life cycle. Therefore, studies on sugar alcohol–amino acid interactions are very significant in food technology, immunology, biosynthesis, pharmacology, and medicines.5 However, thermo-physical studies of the interactions between sugar alcohol and amino acids in solutions are rare. The transport properties of amino acids in mixed aqueous solutions are affected by variations in solute concentration and temperature.6

The amino acid used in the present study is l-arginine. l-Arginine is a nonessential amino acid and the building block of protein, and it has vast applications such as helping in controlling the blood pressure in the body and preventing swelling in the gastrointestinal area in newborn babies. Literature analysis revealed the thermodynamic studies of binary mixtures of sugar alcohol,7,8 but ternary systems of sugar alcohol with amino acid in aqueous systems are very complex and rare. These thermodynamic parameters are also affected by concentration and temperature variations.9

In continuation of our earlier studies on sugar alcohol/sweeteners in aqueous system,10 in the present study density and sound velocity for galactitol in aqueous amino acids (l-arginine) solutions at different temperatures (293.15–318.15 K) have been measured. Using measured data, acoustic and volumetric parameters such as isentropic compressibility, specific molar volume, partial molar volume, expansibility, intermolecular free length, and transfer volume of galactitol from water to arginine solutions were computed. These parameters have been used to deliberate molecular interactions occurring in solutions and the structure-making/breaking tendency of the components in working solutions.11 The objective of the present work is to lift the primary knowledge related to amino acid–sugar alcohol interactions in aqueous solutions, which is still oblivious.

2. Materials and Methods

2.1. Materials

Galactitol (Sigma-Aldrich CAS no. 608-66-2) and l-arginine (Merck CAS no. 74-79-3) were procured from Sigma-Aldrich and Merck. The doubly distilled and deionized water was obtained from Sigma-Aldrich (CAS no. 7732-18-5) and used in solution preparation. All chemicals used in the present work are given in Table 1. Furthermore, all apparatus used in this work was completely cleaned and dried before using it.

Table 1. Investigated Chemicals with Specification.

name of chemical source CAS no. purity (%) purity method
galactitol Sigma-Aldrich 608-66-2 99 crystallization
l-arginine Merck 74-79-3 99 crystallization
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2.2. Methods

The density ρ and sound velocity u of galactitol in water and in aqueous l-arginine solutions (0.02, 0.04, and 0.06) mol kg–1 have been measured in the temperature range of 293.15–318.15 K and at a pressure of 101 kPa using DSA 5000M. The calibration of DSA 5000M was made from density and speed of sound data of pure water and air at 293.15 K according to the instruction manual. The density of a sample was calculated by determining the frequency of the U-tube, first injected water and then with instigated sample solution.12 The principle of measuring density was based on the circulation time method. The investigated sample was placed just like a sandwich between two piezoelectric ultrasonic transducers: one radiated sound waves over the sample-occupied cavity (3 MHz frequency), while the second transducer received emitted waves from the first one. Sound speed measurements have been performed through dividing the traveled distance between the source and the collector and the calculated transmission time for sound velocity 0.5 m s–1, having accuracy 0.1 m s–1. The Sartorius electronic digital weight balance (model no. SAR CP2245, USA) with an accuracy of ±0.001 mg has been used for preparation of solutions.

3. Results and Discussion

3.1. Density and Sound Velocity

The density and sound velocity for pure water and along with literature values at various temperatures are listed in Table 2, which showed that measured values are comparable with literature values.

Table 2. Comparisons of Experimental Densities (ρ0) and Sound Velocities (u0) of Pure Water with Literature Values at Different Temperatures.

  experimental work
 literature values
T/K ρ0/g cm–3 u0/m s–1 ρ0/g cm–3 u0/m s–1
293.15 0.998203 1482.64 0.998202,3 0.9982202 1483.35,3 1483.102
298.15 0.997037 1497.65 0.997748,3 0.9971002 1497.12,3 1497.002
303.15 0.995675 1509.10 0.995241,1 0.99405817 1509.51,3 1509.402
308.15 0.994149 1519.56 0.994258,3 0.9940582 1520.17,3 1519.832
313.15 0.992240 1529.25 0.992570,3 0.9922102 1529.89,3 1528.805
318.15 0.990583 1537.49 0.990356,3 0.99020120 1537.11,3 1537.2119
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The measured values of density ρ and sound velocity u for galactitol in water and in aqueous l-arginine solutions at various temperatures are reported in Table 3.

Table 3. Densities (ρ) and Sound Velocities (u) of Galactitol in Water and in Aqueous l-Arginine Solutions at Various Molal Concentrations of Galactitol (m) and Temperaturesa.

ρ/g cm–3
m/mol kg–1 293.15 K 298.15 K 303.15 K 308.15 K 313.15 K 318.15 K
Galactitol + Water
0.03226 1.000241 0.999056 0.997243 0.996139 0.994205 0.992321
0.05033 1.001369 1.000175 0.998352 0.997241 0.995293 0.993404
0.07495 1.002889 1.001682 0.999847 0.998726 0.996760 0.994865
0.09028 1.003826 1.002612 1.000768 0.999643 0.997665 0.995756
0.11480 1.005310 1.004084 1.002228 1.001093 0.999100 0.997179
0.13342 1.006423 1.005188 1.003323 1.002184 1.000176 0.998239
0.15304 1.007583 1.006341 1.004464 1.003320 1.001298 0.999339
0.17528 1.008884 1.007634 1.005744 1.004590 1.002556 1.000584
0.19501 1.010019 1.008764 1.006862 1.005701 1.003654 1.001661
Galactitol + 0.02 mol kg–1l-Arginine
0.03403 1.001502 1.000287 0.998867 0.997312 0.994428 0.993462
0.05273 1.002662 1.001438 1.000004 0.998441 0.995544 0.994555
0.07689 1.004146 1.002911 1.001460 0.999888 0.996975 0.995956
0.09895 1.005485 1.004242 1.002774 1.001197 0.998269 0.997224
0.11849 1.006659 1.005409 1.003926 1.002346 0.999407 0.998338
0.13555 1.007675 1.006419 1.004922 1.003341 1.000391 0.999303
0.15470 1.008805 1.007542 1.006030 1.004449 1.001490 1.000377
0.17757 1.010138 1.008867 1.007338 1.005759 1.002788 1.001647
0.19572 1.011181 1.009909 1.008363 1.006789 1.003807 1.002646
Galactitol + 0.04 mol kg–1l-Arginine
0.03403 1.001631 1.000508 0.999836 0.998452 0.995424 0.994387
0.05273 1.002788 1.001655 1.000968 0.999577 0.996536 0.995474
0.07689 1.004267 1.003123 1.002417 1.001019 0.997961 0.996868
0.09895 1.005602 1.00445 1.003727 1.002323 0.99925 0.998128
0.11849 1.006773 1.005613 1.004876 1.003469 1.000384 0.999236
0.13555 1.007784 1.006619 1.005870 1.004461 1.001365 1.000195
0.15470 1.008909 1.007738 1.006978 1.005566 1.002459 1.001264
0.17757 1.010237 1.009058 1.008284 1.006871 1.003752 1.002529
0.19572 1.011276 1.010095 1.009311 1.007899 1.004769 1.003525
Galactitol + 0.06 mol kg–1l-Arginine
0.03403 1.004063 1.002964 1.00151 0.999903 0.996953 0.994934
0.05273 1.005209 1.004102 1.002638 1.001020 0.998054 0.996011
0.07689 1.006676 1.005558 1.004082 1.002451 0.999464 0.997392
0.09895 1.008002 1.006873 1.005385 1.003745 1.000739 0.998641
0.11849 1.009167 1.008028 1.006528 1.004881 1.001858 0.999739
0.13555 1.010174 1.009026 1.007517 1.005863 1.002827 1.000689
0.15470 1.011296 1.010135 1.008616 1.006957 1.003904 1.001749
0.17757 1.012623 1.011444 1.00991 1.008249 1.005175 1.003002
0.19572 1.013666 1.012471 1.010927 1.009264 1.006172 1.003988
u/m s–1
m/mol kg–1 293.15 K 298.15 K 303.15 K 308.15 K 313.15 K 318.15 K
Galactitol + Water
0.03226 1488.80 1503.39 1515.82 1525.39 1535.1 1542.95
0.05033 1492.21 1506.88 1519.33 1528.62 1538.34 1546.19
0.07495 1496.86 1511.60 1524.06 1532.97 1542.69 1550.55
0.09028 1499.66 1514.52 1526.99 1535.65 1545.37 1553.25
0.11480 1504.21 1519.15 1531.62 1539.87 1549.6 1557.51
0.13342 1507.59 1522.61 1535.09 1543.01 1552.75 1560.68
0.15304 1511.12 1526.23 1538.74 1546.30 1556.04 1564.01
0.17528 1515.13 1530.27 1542.79 1549.91 1559.71 1567.71
0.19501 1518.59 1533.78 1546.34 1553.04 1562.91 1570.96
Galactitol + 0.02 mol kg–1l-Arginine
0.03403 1485.80 1504.73 1517.08 1527.64 1536.61 1544.52
0.05273 1486.89 1508.40 1520.71 1531.21 1540.13 1548.02
0.07689 1488.31 1513.09 1525.32 1535.72 1544.59 1552.45
0.09895 1489.62 1517.34 1529.48 1539.75 1548.58 1556.41
0.11849 1490.79 1521.04 1533.11 1543.24 1552.07 1559.84
0.13555 1491.82 1524.23 1536.21 1546.26 1555.02 1562.77
0.15470 1492.98 1527.80 1539.68 1549.57 1558.29 1565.98
0.17757 1494.38 1532.00 1543.78 1553.44 1562.09 1569.73
0.19572 1495.51 1535.25 1546.97 1556.43 1565.01 1572.63
Galactitol + 0.04 mol kg–1l-Arginine
0.03403 1492.54 1506.32 1519.77 1529.36 1538.25 1548.07
0.05273 1496.32 1510.06 1523.52 1533.06 1541.90 1551.71
0.07689 1501.15 1514.84 1528.31 1537.78 1546.53 1556.33
0.09895 1505.50 1519.14 1532.62 1542.02 1550.68 1560.46
0.11849 1509.31 1522.93 1536.40 1545.73 1554.27 1564.04
0.13555 1512.55 1526.17 1539.65 1548.91 1557.35 1567.11
0.15470 1516.15 1529.78 1543.26 1552.43 1560.72 1570.43
0.17757 1520.40 1534.06 1547.47 1556.59 1564.63 1574.33
0.19572 1523.69 1537.35 1550.78 1559.85 1567.59 1577.27
Galactitol + 0.06 mol kg–1l-Arginine
0.03403 1495.34 1508.11 1520.32 1530.94 1539.9 1548.13
0.05273 1499.23 1511.96 1524.16 1534.77 1543.67 1551.89
0.07689 1504.19 1516.9 1529.09 1539.67 1548.45 1556.63
0.09895 1508.67 1521.38 1533.56 1544.09 1552.72 1560.85
0.11849 1512.58 1525.32 1537.49 1547.96 1556.40 1564.49
0.13555 1515.94 1528.72 1540.90 1551.31 1559.53 1567.58
0.15470 1519.66 1532.49 1544.68 1555.01 1562.91 1570.95
0.17757 1524.04 1536.95 1549.19 1559.37 1566.89 1574.89
0.19572 1527.41 1540.43 1552.73 1562.72 1569.91 1577.87
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a

m is the molality of galactitol. The standard uncertainties of molality (m), density (ρ), sound velocity (u), and temperature (T) are ±0.00003 mol kg–1, ±0.000006 g cm–3, ±0.029 m s–1, and 0.02 K, respectively. The expanded uncertainties (k = 2) in ρ and u are ±1.32 × 10–6 g cm–3 and ±0.058 m s–1 respectively.

Schemes S1 and S2 for galactitol in water and in aqueous l-arginine solutions are reported in the Supporting Information. In aqueous galactitol solution, the solvent molecules surround the solute molecules. As a result, solute–solvent interaction occurred, but the addition of l-arginine in aqueous solution replaced the solvent molecules. Thus, the structure become more compact and rigged than aqueous solutions.13 The presence of solute–solute and solute–solvent interactions leads to a change in density and sound velocity values.

Figure 1 represents the linear relationship between density versus molality for the binary system of galactitol in water. The addition of l-arginine to aqueous galactitol solution is performed. The density values increase with the rise in the molal concentration (0.02, 0.04, and 0.06) mol kg–1 of l-arginine, which indicates the fact that water molecules develop hydrogen bonds not only with galactitol but also with of l-arginine molecules that make the structure compact and it became more prominent at large concentrations of l-arginine at the same temperatures.

Figure 1.

Figure 1

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Variation of experimental density of galactitol in water corresponding to molality at different temperatures.

However, there is a decline in density data with the rise in the temperature, because of the increase in kinetic energy of system molecules that govern structure binding energy of solvent molecules and make them less dense.14 The kinetic energies of solution molecules increase with the increase in temperature, and the solution becomes less dense. At the same time, sound waves pass over the solutions more comfortably at high temperature. Moreover, at high concentration of both galactitol and l-arginine in aqueous systems at constant temperature, molecular interactions are produced, which reduce the movement of free ions or molecules in solutions; as a result, interference decreased in the way of moving sound waves from solutions and it increased the sound velocity.15

3.2. Apparent Molar and Partial Molar Volume

The apparent molar volume ØV is significant to determine the molecular interactions of the galactitol in water and aqueous l-arginine solutions at different temperatures.10,16

The apparent molar volume ØV has been calculated through the experimental density values using the following equation:16

3.2. 1

where M, m, ρ, and ρ0 are the molar mass of the solute, molality of solutions, density of solution, and density of the solvent, respectively. The calculated apparent molar volume ØV values are presented at different temperatures in Table S1 of the Supporting Information. The partial molar volume ØV0 was obtained by a regression analysis based on the least squares method through the following equation:16

3.2. 2

In eq 2, SV is the experimental slope, which shows the strength of solute–solute interactions and is influenced by a number of factors.11 The computed results of apparent molar volume ØV, partial molar volume ØV0, and experimental slope SV for the investigated mixture (galactitol in aqueous l-arginine) at various temperatures are reported in Table 4.

Table 4. Partial Molar Volumes (ØV0) and Experimental Slopes (SV) of Galactitol in Water and in Aqueous l-Arginine Solutions at Various Molal Concentrations of l-Arginine (mArg) and Temperaturesa.

mArg/mol kg–1 293.15 K 298.15 K 303.15 K 308.15 K 313.15 K 318.15 K
ØV0/cm3 mol–1
0.00 118.608 ± 0.045 119.275 ± 0.002 119.926 ± 0.008 120.378 ± 0.034 121.287 ± 0.005 121.871 ± 0.01
0.02 119.014 ± 0.008 119.606 ± 0.017 120.509 ± 0.008 121.112 ± 0.005 122.051 ± 0.007 123.412 ± 0.004
0.04 119.162 ± 0.006 119.832 ± 0.008 120.740 ± 0.009 121.280 ± 0.058 122.257 ± 0.017 123.657 ± 0.009
0.06 119.703 ± 0.012 120.184 ± 0.019 120.842 ± 0.022 121.631 ± 0.001 122.719 ± 0.016 124.157 ± 0.009
SV/kg cm3 mol–1
0.00 7.256 6.667 6.282 6.154 5.967 4.006
0.02 5.555 4.987 4.046 3.276 2.687 2.119
0.04 5.514 4.534 4.032 3.058 2.366 2.060
0.06 4.786 4.494 3.925 2.875 2.314 2.996
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a

mArg is the molality of l-arginine. The standard uncertainties of molality (m), partial molar volume (ØV0), and temperature (T) are ±0.00003 mol kg–1, ±0.03043 cm3 mol–1, and ±0.02 K, respectively.

The plots of ØV against molality are presented in Figures 2–5, which reveal that an increase in ØV values with the rise in temperature indicates that greater interactions occur in solutions. A positive increase in ØV values leads to the formation of cavities in the structure.17

Figure 2.

Figure 2

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Plot between apparent molar volume (ØV) and molality (m) of galactitol in water at different temperatures.

Figure 5.

Figure 5

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Plot between apparent molar volume (ØV) and molality (m) of galactitol in 0.06 mol kg–1l-arginine at different temperatures.

Figure 3.

Figure 3

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Plot between apparent molar volume (ØV) and molality (m) of galactitol in 0.02 mol kg–1l-arginine at different temperatures.

Figure 4.

Figure 4

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Plot between apparent molar volume (ØV) and molality (m) of galactitol in 0.04 mol kg–1l-arginine at different temperatures.

At low temperature (293.15 K), galactitol molecules do not avail greater space to adjust themselves with solvent molecules, whereas at high temperature (318.15 K) cavities have greater space for the accommodation of solute components to adequate in water molecules through a better approach.18 The apparent molar volume ØV values of mixtures give understanding about molecular interactions existing among the particles of solution mixtures. Greater values of ØV at high concentration and temperature also suggest for greater molecular interactions in solution mixtures, while at lower temperature solute molecules have less space to take in themselves with solvent molecules.17 Similarly, at higher concentration of solute, more solute–solvent interactions are observed because the solvent molecules do not directly attach to the solute surface through hydrogen bonding, hence generating the gap among solution molecules that leads to positive change in apparent molar volume.19 The trends of ØV in solutions of galactitol in aqueous l-arginine and water (0.06 mol kg–1l-Arg > 0.04 mol kg–1l-Arg > 0.02 mol kg–1l-Arg > water) are noted.

Similar trends have been reported in aqueous carbohydrate solutions, and strong ongoing interactions were observed because of the presence of various force components present among solutions. The temperature also has slight effect on the ØV values, and values are also increased with the rise in temperature.20

Commonly the following types of molecular interactions in the solutions of galactitol in water and in aqueous l-arginine are supposed:21

  • Hydrophilic–hydrophobic molecular interactions among the hydrophilic part of galactitol molecules and the hydrophobic part of l-arginine molecules.

  • Hydrophobic–hydrophobic molecular interactions among the galactitol molecules and nonpolar components of l-arginine molecules.

  • Ion–ion molecular interactions among (−OH) groups of galactitol molecules and functional group of l-arginine molecules.

  • Ion-hydrophilic molecular interactions among hydrophilic components galactitol molecules and ion of l-arginine molecules.

All these molecular interactions can affect the stability of the solvent structure in solutions and have been subjected to the molalities and kind of ions existing in solutions.22 All SV values reported in Table 4 are positive, which show weak solute–solvent interactions in aqueous l-arginine solutions. The apparent molar volume ØV and partial molar volume ØV0 values indicate a linear relationship with rising temperature and concentration of l-arginine (amino acid) that illustrates strong solute–solvent interactions due to hydration of solvent molecules around the solute molecules in the solution mixture.10 All these interactions are caused because of hydrogen bonding among hydroxyl groups of galactitol, water molecules, and anionic parts of l-arginine and amino group. In this research work, molecular interactions in aqueous galactitol and aqueous l-arginine systems can be described in the terms of solvation behavior and sweetness response.

Table 4 showed that positive values of partial molar volume, which indicate more dominance of solute–solute interactions in aqueous l-arginine solutions than galactitol in water.10 This increasing value of partial molar volume ØV0 can be explained through hydrogen bonding among solutions components, in which l-arginine molecules replaced the water molecules. As a result, solute–solute interactions became dominant, and this behavior of galactitol leads to the structure-making behavior.23

3.3. Partial Molar Transfer Volume

The partial molar transfer volume ΔtØV0 explains solute–solvent interactions in binary and ternary solutions. It is calculated using eq 3:

3.3. 3

The transfer volume ΔtØV0 values for the galactitol in water and in aqueous l-arginine are observed and reported in Table 5. All values are positive and can be explained in the light of the cosphere overlapping model.24

Table 5. Partial Molar Transfer Volume (ΔtØV0) of Galactitol in Water and in Aqueous l-Arginine Solutions at Various Molal Concentrations of l-Arginine (mArg) and Temperatures.

  ΔtØV0/cm3 mol–1
mArg/mol kg–1 293.15 K 298.15 K 303.15 K 308.15 K 313.15 K 318.15 K
0.02 0.406 0.431 0.583 0.734 0.764 1.541
0.04 0.554 0.557 0.814 0.902 0.97 1.786
0.06 1.095 0.909 0.916 1.253 1.432 2.286
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According to the overlapping model, when two and more than two molecules come in contact with one another in solution, alteration in overlapping occurred; as a result, a change in their thermodynamic values occurred, which was termed as partial molar transfer volume.25 The positive trend of partial molar transfer volume ΔtØV0 shows the impact of solute–solute and solute-solvent interactions. Table 5 indicates that by increasing the concentration of l-arginine in aqueous solutions, more and more l-arginine molecules replaced the water molecules as a result greater solute–solute interactions.26

3.4. Partial Molar Expansibility and Hepler’s Constant

The partial molar expansibility is used to probe the molecular associations in various systems and can be explained in terms of structure-making or structure-breaking ability of solute components in solutions, and the following equation is used to express the variation of ØV0 at different temperatures:17,27

3.4. 4

where a, b, and c are fitting coefficients of eq 4 and are reported in Table 6.

Table 6. Fitting Coefficients of Equation 4 of Galactitol in Water and Galactitol in Aqueous l-Arginine Solution.

mArg/mol kg–1 a/(cm3 mol–1) b/(cm3 mol–1) c/(cm3 mol–1)
0.00 121.54 –0.1391 0.0004
0.02 334.66 –1.5708 0.0028
0.04 330.03 –1.5412 0.0028
0.06 501.72 –2.6651 0.0046
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The partial molar expansibility ØE0 is determined as follows:

3.4. 5

The partial molar expansibility ØE0 values obtained from eq 5 are listed in Table 7. From Table 7, positive ØE value increases with the rise of temperature of the investigated mixture indicate the structure-making property of solute in solution, which may occur because of the existence of more powerful molecular interactions than electrostatic forces of attraction.28

Table 7. Partial Molar Expansibility (ØE0) and Temperature Derivatives of Partial Molar Expansibility [(∂ØE/∂T)p] for Galactitol in Water and in Aqueous l-Arginine Solutions at Different Temperatures.

T/K ØE0/cm3 mol–1 K–1 (∂ØE0/∂T)p/cm3 mol–1 K–2
Galactitol + Water
293.15 0.09542 0.0008
298.15 0.09942
303.15 0.10342
308.15 0.10742
313.15 0.11142
318.15 0.11542
Galactitol + 0.02 mol kg–1l-Arginine
293.15 0.07084 0.0056
298.15 0.09884
303.15 0.12684
308.15 0.15484
313.15 0.18284
318.15 0.21084
Galactitol + 0.04 mol kg–1l-Arginine
293.15 0.10044 0.0075
298.15 0.12844
303.15 0.15644
308.15 0.18444
313.15 0.21244
318.15 0.24044
Galactitol + 0.06 mol kg–1l-Arginine
293.15 0.03188 0.0092
298.15 0.07788
303.15 0.12388
308.15 0.16988
313.15 0.21588
318.15 0.26188
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Hepler’s proposed a statistical equation to define the affinity of solute components, which support or interrupt solvent arrangement around solute particle in the solution. It is calculated by using eq 4 in the following way:29

3.4. 6

The values obtained for (∂2ØV0/∂T2)p stand for Hepler’s constant and are given in Table 7. This constant describes the structure-forming or structure-deforming ability of solute in solution. Galactitol solutions have positive trends of Hepler’s constant, showing that in these solutions the galactitol acts as a structure maker. From Table 7, positive and increasing trends of partial molar expansibility indicated that at less concentration of arginine, molecules develop less interactions with surrounding water molecules via hydrogen bonding between water and solute molecules, such type solute acts as structure-making compounds.30,31 Moreover, when there are greater numbers of l-arginine molecules in solutions, then amino groups of l-arginine molecules developed greater hydrogen bonding both with water molecules and −OH groups of galactitol, so such solutions (∂2ØV/∂T2)p have greater positive values and show more structure-making behavior.

3.5. Apparent Specific Volume

The apparent specific volume (ASV) was determined by the given equation.32

3.5. 7

where ASV, ØV, and M stand for apparent specific volume, apparent molar volume, and molar mass of solute (galactitol) respectively, and values obtained from eq 7 are shown in Table 8. The ASV values increase with the concentration of solute. The reported values for the sweetness range are (0.51–0.71) cm3 g–1, and the results obtained in such a range are considered as sweeteners.16,33

Table 8. Apparent Specific Volumes (ASVs) for Galactitol in Water and in Aqueous l-Arginine Solutions at Various Molal Concentrations of Galactitol (m) and Temperaturesa.

  ASV/cm3 g–1
m/mol kg–1 293.15 K 298.15 K 303.15 K 308.15 K 313.15 K 318.15 K
Galactitol + Water
0.03226 0.6523 0.6559 0.6594 0.6618 0.6668 0.6697
0.05033 0.6531 0.6566 0.6601 0.6626 0.6675 0.6704
0.07495 0.6542 0.6576 0.6611 0.6636 0.6685 0.6712
0.09028 0.6549 0.6583 0.6618 0.6644 0.6691 0.6719
0.11480 0.6560 0.6593 0.6628 0.6652 0.6700 0.6729
0.13342 0.6569 0.6602 0.6636 0.6660 0.6708 0.6737
0.15304 0.6579 0.6610 0.6646 0.6669 0.6716 0.6748
0.17528 0.6590 0.6620 0.6656 0.6680 0.6726 0.6761
0.19501 0.6601 0.6630 0.6661 0.6690 0.6737 0.6775
Galactitol + 0.02 mol kg–1l-Arginine
0.03403 0.6544 0.6575 0.6623 0.6654 0.6705 0.6778
0.05273 0.6550 0.6581 0.6628 0.6659 0.6708 0.6782
0.07689 0.6559 0.6589 0.6635 0.6664 0.6713 0.6786
0.09895 0.6567 0.6596 0.6643 0.6669 0.6718 0.6790
0.11849 0.6576 0.6604 0.6650 0.6675 0.6722 0.6795
0.13555 0.6582 0.6610 0.6657 0.6680 0.6727 0.6799
0.15470 0.6590 0.6618 0.6665 0.6685 0.6731 0.6804
0.17757 0.6601 0.6628 0.6675 0.6693 0.6738 0.6810
0.19572 0.6610 0.6635 0.6683 0.6699 0.6744 0.6816
Galactitol + 0.04 mol kg–1l-Arginine
0.03403 0.6553 0.6587 0.6636 0.6664 0.6716 0.6793
0.05273 0.6559 0.6593 0.6641 0.6668 0.6719 0.6796
0.07689 0.6568 0.6600 0.6648 0.6673 0.6723 0.6800
0.09895 0.6577 0.6607 0.6654 0.6678 0.6728 0.6805
0.11849 0.6585 0.6615 0.6661 0.6683 0.6732 0.6809
0.13555 0.6593 0.6621 0.6662 0.6687 0.6736 0.6814
0.15470 0.6601 0.6629 0.6673 0.6693 0.6741 0.6818
0.17757 0.6612 0.6639 0.6682 0.6700 0.6747 0.6827
0.19572 0.6621 0.6647 0.6689 0.6706 0.6753 0.6829
Galactitol + 0.06 mol kg–1l-Arginine
0.03403 0.6581 0.6607 0.6642 0.6683 0.6742 0.6821
0.05273 0.6586 0.6612 0.6647 0.6687 0.6745 0.6824
0.07689 0.6593 0.6620 0.6654 0.6692 0.6752 0.6828
0.09895 0.6599 0.6627 0.6662 0.6698 0.6756 0.6833
0.11849 0.6605 0.6634 0.6669 0.6703 0.6762 0.6837
0.13555 0.6611 0.6640 0.6675 0.6709 0.6767 0.6841
0.15470 0.6617 0.6648 0.6683 0.6715 0.6773 0.6845
0.17757 0.6625 0.6658 0.6694 0.6723 0.6782 0.6851
0.19572 0.6631 0.6666 0.6702 0.6729 0.6789 0.6856
Open in a new tab
a

m is the molality of aqueous galactitol. The standard uncertainties of molality (m), ASV, and temperature (T) are ±0.00003 mol kg–1, ±0.0005 cm3 g–1, and ±0.02 K, respectively.

On the other hand, aqueous galactitol solution has an ASV range of (0.65 – 0.67) mol g–1 but aqueous l-arginine systems have ranges (0.65 – 0.68) mol g–1respectively.34,35 The ASV values for galactitol in the presence of l-arginine have nearly ideal sweet range values. It is also observed that the sweetness of galactitol enhanced in the presence of l-arginine.

3.6. Apparent and Partial Molar Isentropic Compressibility

The apparent molar isentropic compressibility Øk provides understanding of intermolecular collaborations in solutions and is calculated by the following equation:36,10

3.6. 8

where βs stands for compressibility of solutions and βs0 for water, respectively and βs is determined by the following equation:

3.6. 9

Calculated results of Økfor aqueous galactitol and aqueous l-arginine solutions are reported in supplementary Table S2. The Øk shows negative decreasing trends for all investigated solutions, which indicate that part of solutions involved by hydrate solute components is compressed lightly because of the existence of strong molecular collaborations than in bulk mixtures.37

Figures 6–9 represent the negative decreasing trend due to compatibility of the structure.38 The investigated solutions have a negative decreasing trend with concentration and temperature for aqueous sugar alcohol and aqueous l-arginine systems because of the development of the complex arrangement in solutions.10,17 From measured data of Øk, the apparent molar compressibility at infinite dilution is known as partial molar compressibility Øk0 and is calculated as39

3.6. 10

where Øk0 stands for partial molar compressibility, Sk stands for the experimental slope, and m is molality of solution. Calculated data of Øk are stated in Table 9. Negative trends of Øk0 describe that molecular interactions became weak in the ternary mixture of in solute-solvent due to participation of l-arginine molecules as a cosolute, which replaced the water molecules from solution and increased the solute–solute interactions so, l-arginine molecules are dynamic in the solution that modified the structure.

Figure 6.

Figure 6

Open in a new tab

Plot between apparent molar isentropic compressibility (Øk) and molality (m) of galactitol in aqueous solution at different temperatures.

Figure 9.

Figure 9

Open in a new tab

Plot between apparent molar isentropic compressibility (Øk) and molality (m) of galactitol in 0.06 mol kg–1l-arginine at different temperatures.

Table 9. Partial Molar Compressibilities (Øk0) and Experimental Slopes (Sk) for Galactitol in Water and in Aqueous l-Arginine Solutions at Various Molal Concentrations of l-Arginine (mArg) and Temperaturesa.

marg/mol kg–1 293.15 K 298.15 K 303.15 K 308.15 K 313.15 K 318.15 K
Øk0/cm3 mol–1 Pa–1
0.00 –9.405 ± 0.032 –9.270 ± 0.007 –9.172 ± 0.029 –8.051 ± 0.053 –7.963 ± 0.001 –7.775 ± 0.048
0.02 –9.714 ± 0.011 –9.365 ± 0.006 –9.041 ± 0.010 –8.683 ± 0.011 –8.395 ± 0.006 –8.152 ± 0.003
0.04 –10.078 ± 0.006 –9.614 ± 0.007 –9.287 ± 0.005 –8.976 ± 0.006 –8.646 ± 0.005 –8.383 ± 0.006
0.06 –10.132 ± 0.006 –9.648 ± 0.004 –9.406 ± 0.003 –9.160 ± 0.005 –9.040 ± 0.009 –8.795 ± 0.006
Sk/kg cm3 mol–2
0.00 4.402 4.771 3.793 3.498 2.966 2.927
0.02 4.636 4.738 5.953 4.267 3.901 3.314
0.04 5.890 5.694 5.169 5.548 4.850 4.077
0.06 4.659 3.478 4.233 4.054 4.324 4.087
Open in a new tab
a

mArg is the molality of aqueous l-arginine. The standard uncertainties of molality (m), partial molar isentropic compressibility (Øk0) are ±0.00003 mol kg–1, ±0.015 cm3 mol–1 Pa–1, and ±0.02 K, respectively.

Figure 7.

Figure 7

Open in a new tab

Plot between apparent molar isentropic compressibility (Øk) and molality (m) of galactitol in 0.02 mol kg–1l-arginine at different temperatures.

Figure 8.

Figure 8

Open in a new tab

Plot between apparent molar isentropic compressibility (Øk) and molality (m) of galactitol in 0.04 mol kg–1l-arginine at different temperatures.

Likewise, attractive forces, various types of molecular interactions among hydrophilic groups of l-arginine and water molecules create contact with sugar alcohol molecules and as a result form hydrophilic–hydrophilic interactions. Table 9 shows the experimental slope Sk data, which provide information about solute–solute interactions.

3.7. Intermolecular Free Length

Ultrasonic velocity is a parameter known as intermolecular free length Lf, which has been determined by the use of adiabatic compressibility values of solutions. It measures the degree of intermolecular interactivity that exists in solutions. A statistical equation is used to measure the intermolecular free length:40

3.7. 11

where k is the Jacobson constant of temperatures (k = (93.875 + 0.375T) × 10–8).

Results of Lf are given in Table 10 that showed with the rise in temperature and concentrations of solute of solutions, the values of Lf decrease as a result of strong association among solute (galactitol), solvent (water), and amino acid molecules, which make the structure more complex and packed and as a result Lf values are decreased.41,42

Table 10. Intermolecular Free Lengths (Lf) for Galactitol in Water and in Aqueous l-Arginine Solutions at Different Temperatures and Molalities of Galactitol (m)a.

  Lf/10–7 m
m/mol kg–1 293.15 K 298.15 K 303.15 K 308.15 K 313.15 K 318.15 K
Galactitol + Water
0.032 1.856 1.839 1.825 1.819 1.815 1.809
0.050 1.850 1.833 1.820 1.810 1.800 1.790
0.074 1.843 1.826 1.813 1.805 1.799 1.795
0.090 1.839 1.822 1.809 1.800 1.795 1.789
0.114 1.832 1.815 1.802 1.799 1.789 1.785
0.133 1.827 1.810 1.797 1.795 1.785 1.779
0.153 1.821 1.805 1.792 1.789 1.779 1.775
0.175 1.815 1.799 1.786 1.785 1.775 1.769
0.195 1.810 1.794 1.781 1.770 1.769 1.765
Galactitol + 0.02 mol kg–1l-Arginine
0.034 1.861 1.844 1.831 1.820 1.810 1.802
0.052 1.858 1.836 1.822 1.811 1.803 1.795
0.076 1.856 1.830 1.817 1.806 1.798 1.790
0.098 1.853 1.823 1.810 1.799 1.791 1.783
0.118 1.855 1.817 1.804 1.793 1.786 1.778
0.135 1.847 1.812 1.799 1.788 1.781 1.773
0.154 1.845 1.807 1.794 1.784 1.776 1.769
0.177 1.842 1.802 1.789 1.779 1.772 1.764
0.195 1.840 1.796 1.783 1.773 1.766 1.759
Galactitol + 0.04 mol kg–1l-Arginine
0.032 1.860 1.844 1.831 1.820 1.817 1.802
0.050 1.850 1.834 1.818 1.808 1.800 1.790
0.074 1.844 1.828 1.813 1.803 1.795 1.785
0.090 1.837 1.821 1.806 1.796 1.788 1.778
0.114 1.830 1.815 1.799 1.790 1.782 1.772
0.133 1.824 1.809 1.794 1.784 1.777 1.767
0.153 1.820 1.804 1.789 1.780 1.773 1.763
0.175 1.814 1.799 1.784 1.775 1.768 1.758
0.195 1.808 1.793 1.778 1.769 1.763 1.753
Galactitol + 0.06 mol kg–1l-Arginine
0.032 1.860 1.844 1.831 1.820 1.817 1.810
0.050 1.844 1.829 1.816 1.805 1.797 1.789
0.074 1.838 1.824 1.810 1.799 1.792 1.784
0.090 1.831 1.816 1.803 1.792 1.785 1.777
0.114 1.824 1.810 1.797 1.786 1.779 1.771
0.133 1.818 1.804 1.791 1.781 1.774 1.766
0.153 1.813 1.799 1.786 1.776 1.769 1.762
0.175 1.808 1.794 1.781 1.771 1.764 1.757
0.195 1.802 1.787 1.775 1.765 1.759 1.752
Open in a new tab
a

m is the molality of aqueous galactitol. The standard uncertainties of molality (m), intermolecular free length (Lf), and temperature (T) are ±0.00003 mol kg–1, ±0.001 m, and ±0.02 K, respectively.

The solute molecules or ions may lead to structural change around solvent molecules. These structural changes depend on the corresponding strength of hydrogen or other types of bonding in the solutions. The calculated values of Lf for aqueous sugar alcohol and l-arginine solutions in water show that by rising concentrations of solute, cosolute, and temperature, the Lf values decline, which indicate the strong molecular interactions such as solute–solute and solute–solvent molecules. This decreasing trend of Lf with concentration and temperature makes the structure compact.43 A decreasing trend in Lf values also indicates the close stuffing of molecules and structure-making behavior.1

4. Conclusions

In the present work, volumetric and acoustic parameters for galactitol in aqueous l-arginine solutions at different temperatures were observed and used to explore the solvation behavior and sweetness response in terms of solute–solute and solute–solvent molecular interactions, and the effect of l-arginine on aqueous galactitol solutions at different temperatures (293.15, 298.15, 303.15, 313.15, and 318.15 K) was also described. Positive trends of apparent molar volumes ØV and partial molar volume ØV0 have been observed, which were retained on increasing the concentration of both galactitol and l-arginine due to hydration of water molecules around the galactitol molecules in the solution mixture. A positive trend of ΔtØV indicated greater strength of electrostatic forces of attractions among solutions, which were much stronger due to the presence of solute–solute interactions in ternary solutions as compared with binary systems. These forces can affect the stability of the solvent structure in solutions and have been subjected to the molalities and kinds of ions existing in solutions. ASV described that investigated galactitol lies in the sweeteners range and its sweetness improved in the presence of l-arginine and the solvation behavior of aqueous galactitol also enriched in the existence of l-arginine than aqueous sugar alcohol solution. Positive trends of ØE0 indicated the structure-promoting response of galactitol in l-arginine solutions.

Acknowledgments

The authors extend their appreciation to the Deanship of Scientific Research at King Khalid University, Abha, Saudi Arabia for funding this work through General Research Project under grant number (G.R.P/23/43).

Supporting Information Available

The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acsomega.2c04102.

  • Scheme S1 for galactitol in aqueous solution, Scheme S2 for galactitol in aqueous l-arginine, Table S1 containing data for apparent molar volume (ØV), and Table S2 for apparent molar isentropic compressibility (Øk) (PDF)

The authors declare no competing financial interest.

Supplementary Material

ao2c04102_si_001.pdf (287KB, pdf)

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