The Impact of Solvent Polarity on the Stability, Electronic Properties, and 1H NMR Chemical Shift of the Conformers of 2-Chloro-3-Methylcyclohexan-1-One Oxime: a Conceptual DFT Approach

Milani, Neda Najjari; Ghiasi, Reza; Forghaniha, Ali

doi:10.1007/s10812-020-00949-9

Cited by 16 publications

(5 citation statements)

References 66 publications

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“…Previous studies also indicated that higher oil yields for aquatic products such as Antarctic krill (Euphausia superba) were achieved with ethanol extraction comparing to n-hexane and acetone extractions (Gigliotti et al, 2011;Xie et al, 2017;Zhou et al, 2017), which is in agreement with our results. There is no doubt that the dielectric constant (C²/(N•M²)) of a solvent is a convenient measure of polarity of a solvent (Milani et al, 2020). For example, compared with nonpolar organic solvents such as hexane (1.88 C²/(N•M²)), polar organic solvents including ethanol (24.5 C²/(N•M²)) are better for more consistent extraction of polar components (phospholipid and lipoproteins) from materials, and thus increase the extraction yield (Bauemler et al, 2016;Nichols et al, 2011).…”

Section: Extraction Yieldmentioning

confidence: 99%

Comparison of different solvents for extraction of oils from by‐products of shrimps Penaeus vannamei and Procambarus clarkia

Wang

Yin

et al. 2021

J. Food Process. Preserv.

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The effects of different extraction solvents on the extraction yield and chemical composition of oils from by-products of marine shrimp Penaeus vannamei (Pv) and freshwater shrimp Procambarus clarkia (Pc) were investigated. Our results indicated that the ethanol and n-hexane mixture (4:1, v/v) was suitable solvent for simultaneous extraction of phospholipid and nonpolar lipids. By contrast, the ethanol and n-hexane mixture (4:1, v/v) and single ethanol were suitable solvents for the extraction of polyunsaturated fatty acids-rich (36.10%-42.78% of total fatty acids for Pv and 23.57%-25.58% of total fatty acids for Pc) and phosphatidylcholine-rich (66.22-67.09 mol% of total phospholipids for Pv and 55.01-58.68 mol% of total phospholipids for Pc) oils, but acetone was suitable solvent for the extraction of astaxanthin-rich oil (436.19 μg/g oil for Pv and 799.27 μg/g oil for Pc). The findings will provide relevant information that can be used to improve the production of nutritional oils from shrimp by-products. Practical applicationsThis study provides a theoretical basis for creating proper extraction processing to recover nutritional oils from shrimp by-products. For example, the ethanol and n-hexane mixture (4:1, v/v) was a suitable solvent for simultaneous extraction of phospholipid and non-polar lipids. By contrast, both of the ethanol and n-hexane mixture (4:1, v/v) and single ethanol were suitable solvents for the extraction of polyunsaturated fatty acids (PUFA)-rich and phosphatidylcholine-rich oils, but acetone was a suitable solvent for the extraction of astaxanthin-rich oil. Therefore, the oils extracted from shrimp by-products are rich in phospholipid, PUFA, and astaxanthin, which may be used as new functional food ingredients.

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Section: Extraction Yieldmentioning

confidence: 99%

Comparison of different solvents for extraction of oils from by‐products of shrimps Penaeus vannamei and Procambarus clarkia

Wang

Yin

et al. 2021

J. Food Process. Preserv.

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“…In general, the solvent polarity can be determined based on its dielectric constant. Accordingly, polar solvents like ethanol (24.55 C 2 /N·M 2 , 25 °C) and isopropanol (19.92 C 2 /N·M 2 , 25 °C) compared to the nonpolar solvent such as n -hexane (1.88 C 2 /(N·M) are more able to extract polar constituents from natural substances, resulting in a higher EE [ 38 , 39 ]. In other words, the difference in oil extraction yields obtained from pure organic solvents (i.e., n -hexane, ethanol, and isopropanol) and their binary mixtures can be related to the co-extraction of any polar compounds, lipidic or not, enhancing the mass of extracted oil.…”

Section: Resultsmentioning

confidence: 99%

Ultrasound-Assisted Alcoholic Extraction of Lesser Mealworm Larvae Oil: Process Optimization, Physicochemical Characteristics, and Energy Consumption

Gharibzahedi

Altıntaş

2022

Antioxidants

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The ultrasound-assisted extraction (UAE) of oil from lesser mealworm (Alphitobius diaperinus L.) larvae powders (LMLPs) using ethanol/isopropanol as the superior solvent was optimized. The evaluation of time (9.89–35.11 min), solvent-to-LMLPs (2.39–27.61 v/w), and temperature (16.36–83.64 °C) showed that the highest extraction efficiency (EE, 88.08%) and in vitro antioxidant activity (IVAA) of reducing power (0.651), and DPPH free-radical scavenging capacity (70.79%) were achieved at 22.5 v/w solvent-to-LMLPs and 70 °C for 22.64 min. Optimal ultrasound conditions significantly improved the EE than n-hexane extraction (60.09%) by reducing the electric energy consumption by ~18.5 times from 0.637 to 0.035 kWh/g. The oil diffusivity in ethanol-isopropanol during the UAE (0.97 × 10−9 m2/s) was much better than that of n-hexane (5.07 × 10−11 m2/s). The microstructural images confirmed the high efficiency of ethanol-isopropanol in the presence of ultrasounds to remove oil flakes from the internal and external surfaces of LMLPs. The improved IVAA was significantly associated with the total phenolic (4.306 mg GAE/g, r = 0.991) and carotenoid (0.778 mg/g, r = 0.937) contents (p < 0.01). Although there was no significant difference in the fatty acid profile between the two extracted oils, ethanol-isopropanol under sonication acceptably improved oxidative stability with lower peroxides, conjugated dienes and trienes, and free fatty acids.

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“…Post‐self‐consistent field calculations of zero‐point vibrational energy and Gibbs free energy were performed using G4(MP2), 34 B3LYP/6–311++G(2d,p), 35–37 and MP2/6–311++G(d,p) 38 . It is well known that the accounting of solvent during the investigation of fine structural effects is important 39–49 . Therefore, we estimated the effect of the reaction medium by using the polarizable continuum model 50 with B3LYP/6–311++G (2d,p) approximation.…”

Section: Computational Detailsmentioning

confidence: 99%

“…38 It is well known that the accounting of solvent during the investigation of fine structural effects is important. [39][40][41][42][43][44][45][46][47][48][49] Therefore, we estimated the effect of the reaction medium by using the polarizable continuum model 50 with B3LYP/6-311++G (2d,p) approximation. The following solvents were used: CCl 4 , CHCl 3 , CH 3 COCH 3 , CH 3 OH, DMSO and water.…”

Section: Introductionmentioning

confidence: 99%

Quantum chemical investigation of structure and stability conformers (R)‐4‐menthen‐3‐one

Вакулин

Latipova

Rafikova

et al. 2020

J Chinese Chemical Soc

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In this work, we study the structure and ratio of (R)‐4‐menthen‐3‐one conformers using ab initio methods. It was shown that the methyl group in (R)‐4‐menthen‐3‐one preferred an equatorial position. In the most stable conformer of the (R)‐4‐menthen‐3‐one, the methyl radical of the i‐Pr group is oriented to C=C double bond, so this group has a more steric hindrance effect on double bond. The ratio of conformers in solvents increases in favor of the most stable conformer.

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The Impact of Solvent Polarity on the Stability, Electronic Properties, and 1H NMR Chemical Shift of the Conformers of 2-Chloro-3-Methylcyclohexan-1-One Oxime: a Conceptual DFT Approach

Cited by 16 publications

References 66 publications

Comparison of different solvents for extraction of oils from by‐products of shrimps Penaeus vannamei and Procambarus clarkia

Comparison of different solvents for extraction of oils from by‐products of shrimps Penaeus vannamei and Procambarus clarkia

Ultrasound-Assisted Alcoholic Extraction of Lesser Mealworm Larvae Oil: Process Optimization, Physicochemical Characteristics, and Energy Consumption

Quantum chemical investigation of structure and stability conformers (R)‐4‐menthen‐3‐one

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