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The insight into the separation of erucic acid, palmitic acid, and nervous acid in Acer truncatum seed oil from solid–liquid phase equilibrium and eutectic behaviors

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Abstract

Acer truncatum seed oil, extracted from the samaras of the yuanbaofeng (A. truncatum Bunge) tree, is rich in oleic acid, palmitic acid (PA), erucic acid (EA), and nervonic acid (NA). The melt crystallization is a crucial way to isolate NA. In this present study, the solid–liquid equilibrium of erucic acid/palmitic acid (EA– +PA), erucic acid/nervonic acid (EA–NA), and nervonic acid/palmitic acid (NA–PA) binary systems was investigated by differential scanning calorimetry. The solid–liquid phase diagrams of binary systems were constructed by thermodynamic analysis and model simulations, which illustrated the influence of molecular interaction on the melting point change of binary systems. The solid–liquid phase and the enthalpy change diagrams together demonstrated eutectic phenomenon. The eutectic behavior appeared in the EA–NA and EA–PA binary systems at the EA concentration more than 50% and 70%, respectively. Additionally, the FTIR spectra of PA, EA, NA, and various binary systems were characterized, which found that there was no chemical interaction between the binary components. Based on the calculation of the enthalpy, onset melting temperature, and peak temperature in the melting stage, the melting Gibbs free energy of binary systems during phase transformation was predicted. These findings provided a fresh light for the separation of NA from A. truncatum seed oil, hence providing theoretical instruction for the separation of fatty acids in plant oil.

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Abbreviations

OA:

Oleic acid

EA:

Erucic acid

PA:

Palmitic acid

NA:

Nervonic acid

DSC:

Differential scanning calorimetry

L PA :

The liquid phase of palmitic acid

L EA :

The liquid phase of erucic acid

S PA :

The solid phase of palmitic acid

S EA :

The solid phase of erucic acid

L NA :

The liquid phase of nervonic acid

S NA :

The solid phase of nervonic acid

FTIR:

Fourier transform infrared spectroscopy

References

  1. Velisek J, Cejpek K. Biosynthesis of food constituents: lipids. 1. Fatty acids and derived compounds—a review. Czech J Food Sci. 2006;24:193–216.

    Article  CAS  Google Scholar 

  2. Harwood JL. Recent advances in the biosynthesis of plant fatty acids. Biochim Biophys Acta. 1996;1301:7–56.

    Article  PubMed  Google Scholar 

  3. Ntoumani E, Strandvik B, Sabel KG. Nervonic acid is much lower in donor milk than in milk from mothers delivering premature infants—Of neglected importance? Prostaglandins Leukot Essent Fatty Acids. 2013;89:241–4.

    Article  CAS  PubMed  Google Scholar 

  4. Liu Y, Li Y, Shen H, Li Y, Xu Y, Zhou M, Xia X, Shi B. Association between the metabolic profile of serum fatty acids and diabetic nephropathy: a study conducted in northeastern China. Ther Adv Endocrinol Metab. 2022;13:291–9.

    Article  Google Scholar 

  5. Phung NV, Rong F, Xia WY, Fan Y, Li XY, Wang SA, Li FL. Nervonic acid and its sphingolipids: biological functions and potential food applications. Crit Rev Food Sci Nutr. 2023. https://doi.org/10.1080/10408398.2023.2203753.

    Article  PubMed  Google Scholar 

  6. Wang X, Zhu X, Li X, Li Z, Mao Y, Zhang S, Liu X, Liu X, Liu Y, Cao F, Zhang J. Transcriptomic and metabolomic analyses provide insights into the attenuation of neuroinflammation by nervonic acid in MPTP-stimulated PD model mice. Food Funct. 2023;14:277–91.

    Article  PubMed  Google Scholar 

  7. Liang Q, Wang W, Yuan F, Liu X, Li D, Yang KQ. Characterization of yuanbaofeng (Acer truncatum Bunge) samaras: oil, fatty acid, and phytosterol content. Ind Crops Prod. 2019;135:344–51.

    Article  CAS  Google Scholar 

  8. Yu X, Ang HC, Yang H, Zheng C, Zhang Y. Low temperature cleanup combined with magnetic nanoparticle extraction to determine pyrethroids residue in vegetables oils. Food Control. 2017;74:112–20.

    Article  CAS  Google Scholar 

  9. Pejin B, Bianco A, Newmaster S, Sabovljevic M, Vujisic L, Tesevic V, Vajs V, De Rosa S. Fatty acids of Rhodobryum ontariense (Bryaceae). Nat Prod Res. 2012;26:696–702.

    Article  CAS  PubMed  Google Scholar 

  10. Maximo GJ, Aquino RT, Meirelles AJA, Krahenbuhl MA, Costa MC. Enhancing the description of SSLE data for binary and ternary fatty mixtures. Fluid Phase Equilib. 2016;426:119–30.

    Article  CAS  Google Scholar 

  11. Maximo GJ, Costa MC, Coutinho JAP, Meirelles AJA. Trends and demands in the solid–liquid equilibrium of lipidic mixtures. RSC Adv. 2014;4:31840–50.

    Article  CAS  Google Scholar 

  12. Costa MC, Rolemberg MP, Boros LAD, Krähenbühl MA, De Oliveira MG, Meirelles AJA. Solid−liquid equilibrium of binary fatty acid mixtures. J Chem Eng Data. 2007;52:30–6.

    Article  CAS  Google Scholar 

  13. Mirpoorian SM, Vakili M, Baghban SHN, Roohi P. Determination and measurement of solid-liquid equilibrium for binary fatty acid mixtures based on NRTL and UNIQUAC activity models. J Therm Anal Calorim. 2019;137:679–88.

    Article  CAS  Google Scholar 

  14. Qiu S, Wang X, Zan M, Wang Z, Dang L. The insight into separation of oleic, linoleic, and α-linolenic acid in peony seed oil from eutectic behaviors, polymorphic transition and solid-liquid phase equilibrium. LWT. 2021;138:110738.

    Article  CAS  Google Scholar 

  15. Gandolfo FG, Bot A, Flöter E. Phase diagram of mixtures of stearic acid and stearyl alcohol. Thermochim Acta. 2003;404:9–17.

    Article  CAS  Google Scholar 

  16. Inoue T, Hisatsugu Y, Suzuki M, Wang ZN, Zheng LQ. Solid-liquid phase behavior of binary fatty acid mixtures 3. Mixtures of oleic acid with capric acid (decanoic acid) and caprylic acid (octanoic acid). Chem Phys Lipids. 2004;132:225–34.

    CAS  PubMed  Google Scholar 

  17. Maximo GJ, Costa MC, Meirelles AJA. Solid–liquid equilibrium of triolein with fatty alcohols. Braz J Chem Eng. 2013;30:33–43.

    Article  Google Scholar 

  18. De Matos FC, Da Costa MC, Meirelles AJD, Batista EAC. Binary solid-liquid equilibrium systems containing fatty acids, fatty alcohols and trilaurin by differential scanning calorimetry. Fluid Phase Equilib. 2016;423:74–83.

    Article  Google Scholar 

  19. Unsal M, Aktas N. Fractionation and characterization of edible sheep tail fat. Meat Sci. 2003;63:235–9.

    Article  CAS  PubMed  Google Scholar 

  20. Carareto NDD, Castagnaro T, Costa MC, Meirelles AJA. The binary (solid plus liquid) phase diagrams of (caprylic or capric acid) + (1-octanol or 1-decanol). J Chem Thermodyn. 2014;78:99–108.

    Article  CAS  Google Scholar 

  21. Tan CP, Man YBC. Recent developments in differential scanning calorimetry for assessing oxidative deterioration of vegetable oils. Trends Food Sci Technol. 2002;13:312–8.

    Article  CAS  Google Scholar 

  22. Zhang L, Ueno S, Sato K, Adlof RO, List GR. Thermal and structural properties of binary mixtures of 1,3-distearoyl-2-oleoyl-glycerol (SOS) and 1,2-dioleoyl-3-stearoyl-sn-glycerol (sn-OOS). J Therm Anal Calorim. 2009;98:105–11.

    Article  CAS  Google Scholar 

  23. Della Gatta G, Richardson MJ, Sarge SM, Stolen S. Standards, calibration, and guidelines in microcalorimetry—part 2. Calibration standards for differential scanning calorimetry—(IUPAC technical report). Pure Appl Chem. 2006;78:1455–76.

    Article  CAS  Google Scholar 

  24. Yui K, Itsukaichi Y, Kobayashi T, Tsuji T, Fukui K, Maeda K, Kuramochi H. Solid–Liquid equilibria in the binary systems of saturated fatty acids or triglycerides (C12 to C18) + hexadecane. J Chem Eng Data. 2017;62:35–43.

    Article  CAS  Google Scholar 

  25. Lee AG. Lipid phase transitions and phase diagrams. II. Mictures involving lipids. Biochim Biophys Acta. 1977;472:285–344.

    Article  CAS  PubMed  Google Scholar 

  26. Tenchov BG. Nonuniform lipid distribution in membranes. Prog Surf Sci. 1985;20:273–340.

    Article  CAS  Google Scholar 

  27. Eckert K-A, Dasgupta S, Selge B, Ay P. Novel model for the prediction of SSLE temperatures and crystallization paths of any mixture containing palmitic, stearic, oleic, linoleic and linolenic acid. Thermochim Acta. 2017;652:126–40.

    Article  CAS  Google Scholar 

  28. Lu C, Zhang B, Zhang H, Guo Y, Dang L, Liu Z, Shu Q, Wang Z. Solid-Liquid Phase Equilibrium and Phase Behaviors for Binary Mixtures Composed of Tripalmitoylglycerol (PPP), 1,3-Dipalmitoyl-2-oleoyl-glycerol (POP), and 1,2-Dioleoyl-3-palmitoyl-glycerol (POO). Ind Eng Chem Res. 2019;58:10044–52.

    Article  CAS  Google Scholar 

  29. Hernández-Veloz MJ, Rousseau D, Dibildox-Alvarado E, Pérez-Meza LV, Reyes-Hernández J, Ruiz-Cabrera MA, Pérez-Martínez JD. Phase diagrams and microstructure of mixtures of n-hentriacontane and saturated fatty acids. Thermochim Acta. 2023;728: 179595.

    Article  Google Scholar 

  30. Kaneko F, Tashiro K, Kobayashi M. Polymorphic transformations during crystallization processes of fatty acids studied with FT-IR spectroscopy. J Cryst Growth. 1999;198:1352–9.

    Article  Google Scholar 

  31. Inoue T, Hisatsugu Y, Yamamoto R, Suzuki M. Solid-liquid phase behavior of binary fatty acid mixtures 1. Oleic acid stearic acid and oleic acid behenic acid mixtures. Chem Phys Lipids. 2004;127:143–52.

    Article  CAS  PubMed  Google Scholar 

  32. Zeng JL, Cao Z, Yang DW, Xu F, Sun LX, Zhang L, Zhang XF. Phase diagram of palmitic acid-tetradecanol mixtures obtained by DSC experiments. J Therm Anal Calorim. 2009;95:501–5.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. School of Chemical Engineering and Technology, Tianjin University, Tianjin, 300072, China

    Yaqing Fan, Mingyang Zan, Ruixue Wang, Leping Dang & Zhanzhong Wang

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  1. Yaqing Fan
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  2. Mingyang Zan
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  3. Ruixue Wang
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Contributions

All authors contributed to the study conception and design. Material preparation, data collection, and analysis were performed by Yaqing Fan, Mingyang Zan, Ruixue Wang, and Leping Dang. Zhanzhong Wang provided supervision for this work. The first draft of the manuscript was written by Yaqing Fan and Mingyang Zan. All authors read and approved the final manuscript.

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Correspondence to Zhanzhong Wang.

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Fan, Y., Zan, M., Wang, R. et al. The insight into the separation of erucic acid, palmitic acid, and nervous acid in Acer truncatum seed oil from solid–liquid phase equilibrium and eutectic behaviors. J Therm Anal Calorim (2024). https://doi.org/10.1007/s10973-024-13258-6

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