Skip to main content

Lipid Processing and Lipase Activity Under High Pressure Conditions

  • Chapter
  • First Online:
High Pressure Fluid Technology for Green Food Processing

Part of the book series: Food Engineering Series ((FSES))

  • 1586 Accesses

Abstract

Increased understanding of the nutritional values of lipids, has led to the development of novel technologies for modifying fats and oils, or enrichment and isolation of bioactive lipophilic compounds to enhance health benefits resulting from ingestion of these substances. In the last decade, supercritical fluids have proved their ability as an environmentally benign media for extraction, chemical and enzymatic reactions and related processes. Many new processes and products have been developed, using the inherent physical and chemical properties of supercritical fluids.

In this chapter supercritical fluid extraction (SFE) of fat and lipid compounds is reviewed. The effect of pre-treatment and additional conditioning processes on SFE processing is discussed. Finally, supercritical CO2 biocatalytic strategies focusing on the production of bioactive lipids for food industry are presented.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 129.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Hardcover Book
USD 169.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  • Agostini F, Bertussi RA, Agostini G et al (2012) Supercritical extraction from vinification residues: fatty acids, α-tocopherol, and phenolic compounds in the oil seeds from different varieties of grape. ScientificWorldJournal 2012:9

    Article  CAS  Google Scholar 

  • Alexander WS, Brusewitz GH, Maness NO (1997) Pecan oil recovery and composition as affected by temperature, pressure, and supercritical CO2 flow rate. J Food Sci 62:762–766

    Article  CAS  Google Scholar 

  • Almeida PP, Mezzomo N, Ferreira SRS (2012) Extraction of Mentha spicata L. volatile compounds: evaluation of process parameters and extract composition. Food Bioprocess Technol 5:548–559

    Article  CAS  Google Scholar 

  • Al-Zuhair S, Hussein A, Al-Marzouqi AH et al (2012) Continuous production of biodiesel from fat extracted from lamb meat in supercritical CO2 media. Biochem Eng J 60:106–110

    Article  CAS  Google Scholar 

  • Andersson MBO, Demirbuker M, Blomberg LG (1997) Semi-continuous extraction/purification of lipids by means of supercritical fluids. J Chromatogr A 785:337–343

    Article  CAS  Google Scholar 

  • Ansari K, Goodarznia I (2012) Optimization of supercritical carbon dioxide extraction of essential oil from spearmint (Mentha spicata L.) leaves by using Taguchi methodology. J Supercrit Fluids 67:123–130

    Article  CAS  Google Scholar 

  • Arnáiz E, Bernal J, Martín MT et al (2011) Supercritical fluid extraction of lipids from broccoli leaves. Eur J Lipid Sci Technol 113:479–486

    Article  CAS  Google Scholar 

  • Arul J, Boudreau A, Makhlouf J et al (1987) Fractionation of anhydrous milk fat by superficial carbon dioxide. J Food Sci 52:1231–1236

    Article  CAS  Google Scholar 

  • Astaire JC, Ward R, German JB et al (2003) Concentration of polar MFGM lipids from buttermilk by microfiltration and supercritical fluid extraction. J Dairy Sci 86:2297–2307

    Article  CAS  Google Scholar 

  • Barth D, Chouchi D, Porta GD et al (1994) Desorption of lemon peel oil by supercritical carbon dioxide: deterpenation and psoralens elimination. J Supercrit Fluids 7:177

    Article  CAS  Google Scholar 

  • Bauer C, Gamse T, Marr R (2001) Quality improvement of crude porcine pancreatic lipase preparations by treatment with humid supercritical carbon dioxide. Biochem Eng J 9:119–123

    Article  CAS  Google Scholar 

  • Baysal T, Ersus S, Starmans DSJ (2000) Supercritical CO2 extraction of β-carotene and lycopene from tomato paste waste. J Agric Food Chem 48:5507–5511

    Article  CAS  Google Scholar 

  • Berg H, Magard M, Johansson G et al (1997) Development of a supercritical fluid extraction method for determination of lipid classes and total fat in meats and its comparison with conventional methods. J Chromatogr A 785:345–352

    Article  CAS  Google Scholar 

  • Bernal J, Lozano P, Garcia-Verdugo E et al (2012) Supercritical synthesis of biodiesel. Molecules 17:8696–8719

    Article  CAS  Google Scholar 

  • Billakanti JM, Catchpole OJ, Fenton TA et al (2013) Enzyme-assisted extraction of fucoxanthin and lipids containing polyunsaturated fatty acids from Undaria pinnatifida using dimethylether and ethanol. Process Biochem 48:1999–2008

    Article  CAS  Google Scholar 

  • Blasco M, Tárrega A, Capilla V et al (1999) Applications of SCF in food industry. AINIA, Valencia, Spain

    Google Scholar 

  • Bruhl L, Matthaus B (1999) Extraction of oilseeds by SFE—a comparison with other methods for the determination of the oil content. Fresen J Anal Chem 364:631–634

    Article  CAS  Google Scholar 

  • Brunner G (2000) Fractionation of fats with supercritical carbon dioxide. Eur J Lipid Sci Technol 102:240–245

    Article  CAS  Google Scholar 

  • Bulley N, Fattori M, Meisen A et al (1984) Supercritical fluid extraction of vegetable oil seeds. J Am Oil Chem Soc 61:1362–1365

    Article  CAS  Google Scholar 

  • Calvo L, Cocero M, Díez J (1994) Oxidative stability of sunflower oil extracted with supercritical carbon dioxide. J Am Oil Chem Soc 71:1251–1254

    Article  CAS  Google Scholar 

  • Carvalho RHR, Galvao EL, Barros JÃC et al (2012) Extraction, fatty acid profile and antioxidant activity of sesame extract (Sesamum indicum L.). Braz J Chem Eng 29:409–420

    Article  CAS  Google Scholar 

  • Catchpole OJ, Grey JB, Noermark KA (2000) Fractionation of fish oils using supercritical CO2 and CO2+ethanol mixtures. J Supercrit Fluids 19:25–37

    Article  CAS  Google Scholar 

  • Catchpole O, Tallon S, Dyer P et al (2012) Integrated supercritical fluid extraction and bioprocessing. Am J Biochem Biotechnol 8:263–287

    Article  CAS  Google Scholar 

  • Certik M, Horenitzky R (1999) Supercritical CO2 extraction of fungal oil containing g-linolenic acid. Biotechnol Technol 13:11–15

    Article  CAS  Google Scholar 

  • Chao RR, Mulvaney SJ, Bailey ME et al (1991) Supercritical CO2 conditions affecting extraction of lipid and cholesterol from ground beef. J Food Sci 56:183–187

    Article  CAS  Google Scholar 

  • Chen Z, Chao J, Wang B et al (2012) Study on extraction technology of the pigment from spinach. Adv Mater Res 518–523:3931–3937

    Article  Google Scholar 

  • Cheung PCK, Leung AYH, Ang POJ (1998) Comparison of supercritical carbon dioxide and soxhlet extraction of lipids from a Brown Seaweed, Sargassum hemiphyllum (Turn.) C. Ag. J Agric Food Chem 46(10):4228–4232

    Article  CAS  Google Scholar 

  • Chiou RYY, Yu Z-R, Wu P-Y et al (1996) Partial defatting of roasted peanut meals and kernels by supercritical CO2using semicontinuous and intermittently depressurized processes. J Agric Food Chem 44:574–578

    Article  CAS  Google Scholar 

  • Chouchi D, Barth D, Reverchon E et al (1995) Supercritical CO2 desorption of bergamot peel oil. Ind Eng Chem Res 34:4508

    Article  CAS  Google Scholar 

  • Chouchi D, Barth D, Reverchon E et al (1996) Bigarade peel oil fractionation by supercritical carbon dioxide desorption. J Agric Food Chem 44:1100–1104

    Article  CAS  Google Scholar 

  • Christianson DD, Friedrich JP, List GR et al (1984) Supercritical fluid extraction of dry-milled corn germ with carbon dioxide. J Food Sci 49:229–232

    Article  Google Scholar 

  • Ciftci ON (2011) Continuous production of fatty acid methyl esters from corn oil in a supercritical carbon dioxide bioreactor. J Supercrit Fluids 58:79–87

    Article  CAS  Google Scholar 

  • Ciftci ON (2013) Enzymatic conversion of corn oil into biodiesel in a batch supercritical carbon dioxide reactor and kinetic modeling. J Supercrit Fluids 75:172–180

    Article  CAS  Google Scholar 

  • Coelho JP, Cristino AF, Matos PG et al (2012) Extraction of volatile oil from aromatic plants with supercritical carbon dioxide: experiments and modeling. Molecules 17:10550–10573

    Article  CAS  Google Scholar 

  • Crowe T, White P (2003a) Oxidation, flavor, and texture of walnuts reduced in fat content by supercritical carbon dioxide. J Am Oil Chem Soc 80:569–574

    Article  CAS  Google Scholar 

  • Crowe T, White P (2003b) Oxidative stability of walnut oils extracted with supercritical carbon dioxide. J Am Oil Chem Soc 80:575–578

    Article  CAS  Google Scholar 

  • Crowe T, Crowe T, Johnson L et al (2002) Impact of extraction method on yield of lipid oxidation products from oxidized and unoxidized walnuts. J Am Oil Chem Soc 79:453–456

    Article  CAS  Google Scholar 

  • Da Porto C, Decorti D, Tubaro F (2012) Fatty acid composition and oxidation stability of hemp (Cannabis sativa L.) seed oil extracted by supercritical carbon dioxide. Ind Crop Prod 36:401–404

    Article  CAS  Google Scholar 

  • Daković S, Turkulov J, Dimić E (1989) The quality of vegetable oils got by extraction with CO2. Fett-Lipid 91:116–119

    Article  Google Scholar 

  • Dalla Rosa C, Morandim MB, Ninow JL et al (2009) Continuous lipase-catalyzed production of fatty acid ethyl esters from soybean oil in compressed fluids. Bioresour Technol 100:5818–5826

    Article  CAS  Google Scholar 

  • de Oliveira PF, Machado RAF, Bolzan A et al (2012) Supercritical fluid extraction of hernandulcin from Lippia dulcis Trev. J Supercrit Fluids 63:161–168

    Article  CAS  Google Scholar 

  • Degnan AJ, Von Elbe JH, Hartel RW (1991) Extraction of annatto seed pigment by supercritical carbon dioxide. J Food Sci 56:1655–1659

    Article  CAS  Google Scholar 

  • Del Valle JM, Aguilera JM (1989) Effects of substrate densification and CO2 conditions on supercritical extraction of mushroom oleoresins. J Food Sci 54:135–141

    Article  Google Scholar 

  • Díaz-Reinoso B, Moure A, Domínguez H et al (2006) Supercritical CO2 extraction and purification of compounds with antioxidant activity. J Agric Food Chem 54:2441–2469

    Article  CAS  Google Scholar 

  • Dossat V, Combes D, Marty A (1999) Continuous enzymatic transesterification of high oleic sunflower oil in a packed bed reactor: influence of the glycerol production. Enzyme Microbiol Technol 25:194–200

    Article  CAS  Google Scholar 

  • Dunford N, King J (2001) Thermal gradient deacidification of crude rice bran oil utilizing supercritical carbon dioxide. J Am Oil Chem Soc 78:121–125

    Article  CAS  Google Scholar 

  • Egydio JA, Moraes AM, Rosa PTV (2010) Supercritical fluid extraction of lycopene from tomato juice and characterization of its antioxidation activity. J Supercrit Fluids 54:159–164

    Article  CAS  Google Scholar 

  • Fadel H, Marx F, El-Sawy A et al (1999) Effect of extraction techniques on the chemical composition and antioxidant activity of Eucalyptus camaldulensis var. brevirostris leaf oils. Z Lebensm Unters Forsch 208:212–216

    Article  CAS  Google Scholar 

  • Favati F, King JW, Friedrich JP et al (1988) Supercritical CO2 extraction of carotene and lutein from leaf protein concentrates. J Food Sci 53:1532–1536

    Article  CAS  Google Scholar 

  • Fiori L, Solana M, Tosi P et al (2012) Lipid profiles of oil from trout (Oncorhynchus mykiss) heads, spines and viscera: trout by-products as a possible source of omega-3 lipids? Food Chem 134:1088–1095

    Article  CAS  Google Scholar 

  • Fornari T, Ruiz-Rodriguez A, Vicente G et al (2012) Kinetic study of the supercritical CO2 extraction of different plants from Lamiaceae family. J Supercrit Fluids 64:1–8

    Article  CAS  Google Scholar 

  • Friedrich JP, List GR (1982) Characterization of soybean oil extracted by supercritical carbon dioxide and hexane. J Agric Food Chem 30:192–193

    Article  CAS  Google Scholar 

  • Froning GW, Wehling RL, Cuppett SL et al (1998) Moisture content and particle size of dehydrated egg yolk affect lipid and cholesterol extraction using supercritical carbon dioxide. Poultry Sci 77:1718–1722

    Article  CAS  Google Scholar 

  • Fujii K (2012) Process integration of supercritical carbon dioxide extraction and acid treatment for astaxanthin extraction from a vegetative microalga. Food Bioprod Process 90:762–766

    Article  CAS  Google Scholar 

  • Gießauf A, Magor W, Steinberger DJ et al (1999) A study of hydrolases stability in supercritical carbon dioxide (SC-CO2). Enzyme Microb Tech 24:577–583

    Article  Google Scholar 

  • Glowacz G, Bariszlovich M, Linke M et al (1996) Stereoselectivity of lipases in supercritical carbon dioxide. I. Dependence of the regio- and enantioselectivity of porcine pancreas lipase on the water content during the hydrolysis of triolein and its partial glycerides. Chem Phys Lipids 79:101–106

    Article  CAS  Google Scholar 

  • Gonzalez-Vila FJ, Bautista JM, Gutierrez A et al (2000) Supercritical carbon dioxide extraction of lipids from Eucalyptus globulus wood. J Biochem Biophys Methods 43:345–351

    Article  CAS  Google Scholar 

  • Gunnlaugsdottir H, Sivik B (1997) Lipase-catalyzed alcoholysis with supercritical carbon dioxide extraction 1: influence of flow rate. Am Oil Chem Soc 74:1483–1490

    Article  CAS  Google Scholar 

  • Habulin M, Knez Ž (2001) Activity and stability of lipases from different sources in supercritical carbon dioxide and near-critical propane. J Chem Technol Biotechnol 76:1260–1266

    Article  CAS  Google Scholar 

  • Hamdan S, Daood HG, Toth-Markus M et al (2008) Extraction of cardamom oil by supercritical carbon dioxide and sub-critical propane. J Supercrit Fluids 44:25–30

    Article  CAS  Google Scholar 

  • Hammond DA, Karel M, Klibanov AM et al (1985) Enzymatic reactions in supercritical gases. Appl Biochem Biotechnol 11:393–400

    Article  CAS  Google Scholar 

  • Haraldsson G, Kristinsson B, Sigurdardottir R et al (1997) The preparation of concentrates of eicosapentaenoic acid and docosahexaenoic acid by lipase-catalyzed transesterification of fish oil with ethanol. J Am Oil Chem Soc 74:1419–1424

    Article  CAS  Google Scholar 

  • Hauthal WH (2001) Advances with supercritical fluids (review). Chemosphere 43:123–135

    Article  CAS  Google Scholar 

  • He H-P, Cai Y, Mei S et al (2002) Extraction and purification of squalene from Amaranthus grain. J Agric Food Chem 50(2):368–372

    Article  CAS  Google Scholar 

  • He H-P, Corke H, Cai J-G (2003) Supercritical carbon dioxide extraction of oil and squalene from Amaranthus grain. J Agric Food Chem 51(27):7921–7925

    Article  CAS  Google Scholar 

  • Hernandez CE, Chen H-H, Chang C-I et al (2009) Direct lipase-catalyzed lipophilization of chlorogenic acid from coffee pulp in supercritical carbon dioxide. Ind Crop Prod 30:359–365

    Article  CAS  Google Scholar 

  • Hierro MTG, Santa-María G (1992) Supercritical fluid extraction of vegetable and animal fats with CO2—a mini review. Food Chem 45:189–192

    Article  CAS  Google Scholar 

  • Hildebrand C, Dalla Rosa C, Freire DMG (2009) Fatty acid ethyl esters production using a non-commercial lipase in pressurized propane medium. Food Sci Technol (Campinas) 29:603–608

    Google Scholar 

  • Hobbs HR, Thomas NR (2007) Biocatalysis in supercritical fluids, in fluorous solvents, and under solvent-free conditions. Chem Rev 107:2786–2820

    Article  CAS  Google Scholar 

  • Holmes JD, Ziegler KJ, Audriani M et al (1999) Buffering the aqueous phase pH in water-in-CO2 microemulsions. J Phys Chem B 103:5703–5711

    Article  CAS  Google Scholar 

  • Hopper ML, King JW (1991) Enhanced supercritical fluid carbon dioxide extraction of pesticides from foods using pelletized diatomaceous earth. J Assoc Off Anal Chem 74:661–666

    CAS  Google Scholar 

  • Hsu Y-W, Tsai C-F, Chen W-K et al (2011) Determination of lutein and zeaxanthin and antioxidant capacity of supercritical carbon dioxide extract from daylily (Hemerocallis disticha). Food Chem 129:1813–1818

    Article  CAS  Google Scholar 

  • Huang Y-S, Smith RS, Redden PR et al (1991) Modification of liver fatty acid metabolism in mice by ω-3 andω-6 Δ6-desaturase substrates and products. Biochim Biophys Acta 1082:319–327

    Article  CAS  Google Scholar 

  • Ikushima Y, Saito N, Arai M et al (1995) Activation of a lipase triggered by interactions with supercritical carbon dioxide in the near-critical region. J Phys Chem 99:8941–8944

    Article  CAS  Google Scholar 

  • Jenab E, Temelli F, Curtis JM (2013) Lipase-catalysed interesterification between canola oil and fully hydrogenated canola oil in contact with supercritical carbon dioxide. Food Chem 141:2220–2228

    Article  CAS  Google Scholar 

  • Kagliwal LD, Patil SC, Pol AS et al (2011) Separation of bioactives from seabuckthorn seeds by supercritical carbon dioxide extraction methodology through solubility parameter approach. Sep Purif Technol 80:533–540

    Article  CAS  Google Scholar 

  • Kamat SV, Beckman EJ, Russell AJ (1995) Enzyme activity in supercritical fluids. Crit Rev Biotechnol 15:41–71

    Article  CAS  Google Scholar 

  • Kimball DA (1987) Debittering of citrus juices using supercritical carbon dioxide. J Food Sci 52:481–482

    Article  Google Scholar 

  • King JW, List GR (eds) (1996) Supercritical fluid technology in oil and lipid chemistry. AOCS, Champaign

    Google Scholar 

  • King JW, Eller FJ, Snyder J et al (1996) Extraction of fat from ground beef for nutrient analysis using analytical supercritical fluid extraction. J Agric Food Chem 44(9):2700–2704

    Article  CAS  Google Scholar 

  • King JW, Mohamed A, Taylor SL et al (2001a) Supercritical fluid extraction of Vernonia galamensis seeds. Ind Crop Prod 14:241–249

    Article  CAS  Google Scholar 

  • King J, Snyder J, Frykman H et al (2001b) Sterol ester production using lipase-catalyzed reactions in supercritical carbon dioxide. Eur Food Res Technol 212:566–569

    Article  CAS  Google Scholar 

  • Knez Ž, Laudani CG, Habulin M et al (2007) Exploiting the pressure effect on lipase-catalyzed wax ester synthesis in dense carbon dioxide. Biotechnol Bioeng 97:1366–1375

    Article  CAS  Google Scholar 

  • Ko TF, Weng YM, Chiou RY (2002) Squalene content and antioxidant activity of Terminalia catappa leaves and seeds. J Agric Food Chem 50:5343–5348

    Article  CAS  Google Scholar 

  • Ko S-N, Ha T-Y, In Hong S et al (2012) Enrichment of tocols from rice germ oil using supercritical carbon dioxide. Int J Food Sci Technol 47:761–767

    Article  CAS  Google Scholar 

  • Kong K-W, Rajab NF, Nagendra Prasad K et al (2010) Lycopene-rich fractions derived from pink guava by-product and their potential activity towards hydrogen peroxide-induced cellular and DNA damage. Food Chem 123:1142–1148

    Article  CAS  Google Scholar 

  • Krichnavaruk S, Shotipruk A, Goto M et al (2008) Supercritical carbon dioxide extraction of astaxanthin from Haematococcus pluvialis with vegetable oils as co-solvent. Bioresour Technol 99:5556–5560

    Article  CAS  Google Scholar 

  • Kwon K-T, Uddin MS, Jung G-W et al (2010) Supercritical carbon dioxide extraction of phenolics and tocopherols enriched oil from wheat bran. Int J Biol Life Sci 6:117

    Google Scholar 

  • Langezaal CR, Chandra A, Katsiotis ST et al (1990) Analysis of supercritical carbon dioxide extracts from cones and leaves of a Humuluslupulus L. cultivar. J Sci Food Agric 53:455–463

    Article  CAS  Google Scholar 

  • Laudani CG, Habulin M, Knez Ž et al (2007) Lipase-catalyzed long chain fatty ester synthesis in dense carbon dioxide: kinetics and thermodynamics. J Supercrit Fluids 41:92–101

    Article  CAS  Google Scholar 

  • Lee A, Bulley N, Fattori M et al (1986) Modelling of supercritical carbon dioxide extraction of canola oilseed in fixed beds. J Am Oil Chem Soc 63:921–925

    Article  CAS  Google Scholar 

  • Lee J, Kwon CH, Kang JW et al (2009) Biodiesel production from various oils under supercritical fluid conditions by Candida antartica lipase B using a stepwise reaction method. Appl Biochem Biotechnol 156:24–34

    Article  CAS  Google Scholar 

  • Lee J, Kim SB, Kang SW et al (2011) Biodiesel production by a mixture of Candida rugosa and Rhizopus oryzae lipases using a supercritical carbon dioxide process. Bioresour Technol 102:2105–2108

    Article  CAS  Google Scholar 

  • Lee M, Lee D, Cho J et al (2012) Improved high-pressure enzymatic biodiesel batch synthesis in near-critical carbon dioxide. Bioprocess Biosyst Eng 35:105–113

    Article  CAS  Google Scholar 

  • Lee M, Lee D, Cho J et al (2013a) Enzymatic biodiesel synthesis in semi-pilot continuous process in near-critical carbon dioxide. Appl Biochem Biotechnol 171:1118–1127

    Article  CAS  Google Scholar 

  • Lee M, Lee D, Cho J et al (2013b) Optimization of enzymatic biodiesel synthesis using RSM in high pressure carbon dioxide and its scale up. Bioprocess Biosyst Eng 36:775–780

    Article  CAS  Google Scholar 

  • Lenucci MS, Caccioppola A, Durante M et al (2010) Optimisation of biological and physical parameters for lycopene supercritical CO2 extraction from ordinary and high-pigment tomato cultivars. J Sci Food Agric 90:1709–1718

    Article  CAS  Google Scholar 

  • Liau B-C, Shen C-T, Liang F-P et al (2010) Supercritical fluids extraction and anti-solvent purification of carotenoids from microalgae and associated bioactivity. J Supercrit Fluids 55:169–175

    Article  CAS  Google Scholar 

  • Lim S, Rizvi SSH (1995) Continuous supercritical fluid processing of anhydrous milk fat in a packed column. J Food Sci 60:889–893

    Article  CAS  Google Scholar 

  • Lim S, Rizvi SSH (1996) Adsorption and desorption of cholesterol in continuous supercritical fluid processing of anhydrous milk fat. J Food Sci 61:817–820

    Article  CAS  Google Scholar 

  • Lin T-J, Chen S-W (2008) Enrichment of ω-3 polyunsaturated fatty acids into acylglycerols of borage oil via lipase-catalyzed reactions under supercritical conditions. Chem Eng J 141:318–326

    Article  CAS  Google Scholar 

  • Linder M, Matouba E, Fanni J et al (2002) Enrichment of salmon oil with ω-3 PUFA by lipolysis, filtration and enzymatic re-esterification. Eur J Lipid Sci Technol 104:455–462

    Article  CAS  Google Scholar 

  • Lisboa P, Rodrigues AR, Martin JL et al (2014) Economic analysis of a plant for biodiesel production from waste cooking oil via enzymatic transesterification using supercritical carbon dioxide. J Supercrit Fluids 85:31–40

    Article  CAS  Google Scholar 

  • List G, Friedrich J, Christianson D (1984a) Properties and processing of corn oils obtained by extraction with supercritical carbon dioxide. J Am Oil Chem Soc 61:1849–1851

    Article  CAS  Google Scholar 

  • List GR, Friedrich JP, Pominski J (1984b) Characterization and processing of cottonseed oil obtained by extraction with supercritical carbon dioxide. J Am Oil Chem Soc 61:1847–1849

    Article  CAS  Google Scholar 

  • Liu G, Xu X, Gong Y et al (2012) Effects of supercritical CO2 extraction parameters on chemical composition and free radical-scavenging activity of pomegranate (Punica granatum L.) seed oil. Food Bioprod Process 90:573–578

    Article  CAS  Google Scholar 

  • Lopes BLF, Sanchez-Camargo AP, Ferreira ALK et al (2012) Selectivity of supercritical carbon dioxide in the fractionation of fish oil with a lower content of EPA + DHA. J Supercrit Fluids 61:78–85

    Article  CAS  Google Scholar 

  • Lozano P, Garcia-Verdugo E, Bernal JM et al (2012) Immobilised lipase on structured supports containing covalently attached ionic liquids for the continuous synthesis of biodiesel in scCO2. ChemSusChem 5:790–798

    Article  CAS  Google Scholar 

  • Lubary M, Hofland GW, ter Horst JH (2010a) Synthesis and isolation of added-value milk fat derivatives using lipase-catalyzed reactions and supercritical carbon dioxide. Lipid Technol 22:54–57

    Article  CAS  Google Scholar 

  • Lubary M, Jansens PJ, ter Horst JH et al (2010b) Integrated synthesis and extraction of short-chain fatty acid esters by supercritical carbon dioxide. AIChE J 56:1080–1089

    CAS  Google Scholar 

  • Machmudah S, Kawahito Y, Sasaki M et al (2007) Supercritical CO2 extraction of rosehip seed oil: fatty acids composition and process optimization. J Supercrit Fluids 41:421–428

    Article  CAS  Google Scholar 

  • Machmudah S, Zakaria Winardi S, Sasaki M et al (2012) Lycopene extraction from tomato peel by-product containing tomato seed using supercritical carbon dioxide. J Food Eng 108:290–296

    Article  CAS  Google Scholar 

  • Macias-Sanchez MD, Fernandez-Sevilla JM, Fernandez FGA et al (2010) Supercritical fluid extraction of carotenoids from Scenedesmus almeriensis. Food Chem 123:928–935

    Article  CAS  Google Scholar 

  • Mangold HK (1983) Extraction and fractionation of lipids with supercritical carbon dioxide and other inorganic solvents. In: International conference on oils, fats and waxes: fats for the future. Auckland, New Zealand, pp 44–55

    Google Scholar 

  • Mendiola JA, Herrero M, Castro-Puyana M et al (2013) Supercritical fluid extraction. In: Rostagno MA, Prado JM (eds) Natural product extraction. Published by The Royal Society of Chemistry, Thomas Graham House, Sience Park, Milton Road, Cambridge, CB4 0WF, UK

    Google Scholar 

  • Merkle JA, Larick DK (1995) Fatty acid content of supercritical carbon dioxide extracted fractions of beef fat. J Food Sci 60:959–962

    Article  CAS  Google Scholar 

  • Mezzomo N, Mileo BR, Friedrich MT et al (2010) Supercritical fluid extraction of peach (Prunus persica) almond oil: process yield and extract composition. Bioresour Technol 101:5622–5632

    Article  CAS  Google Scholar 

  • Micic V, Lepojevic Z, Jotanoviaæ M et al (2011) Supercritical Extraction of Salvia officinalis L. J Appl Sci 11:3630

    Article  CAS  Google Scholar 

  • Molero Gómez A, Martínez de la Ossa E (2000) Quality of wheat germ oil extracted by liquid and supercritical carbon dioxide. J Am Oil Chem Soc 77:969–974

    Article  Google Scholar 

  • Molero X, Guarner F, Salas A et al (1995) Nitric oxide modulates pancreatic basal secretion and response to cerulein in the rat: effects in acute pancreatitis. Gastroenterology 108:1855–1862

    Article  CAS  Google Scholar 

  • Mori T, Kobayashi A, Okahata Y (1998) Biocatalytic esterification in supercritical carbon dioxide by using a lipid-coated lipase. Chem Lett 27:921–922

    Article  Google Scholar 

  • Muñio MM, Esteban L, Robles A et al (2008) Synthesis of 2-monoacylglycerols rich in polyunsaturated fattyacids by ethanolysis of fish oil catalyzed by 1,3 specific lipases. Process Biochem 43:1033–1039

    Article  CAS  Google Scholar 

  • Nyam K, Tan C, Lai O et al (2011) Optimization of supercritical CO2 extraction of phytosterol-enriched oil from Kalahari melon seeds. Food Bioprocess Tech 4:1432–1441

    Article  CAS  Google Scholar 

  • Oliveira D (2001) Enzymatic alcoholysis of palm kernel oil in n-hexane and SCCO2. J Supercrit Fluids 19:141–148

    Article  CAS  Google Scholar 

  • Ollanketo M, Hartonen K, Riekkola M-L et al (2001) Supercritical carbon dioxide extraction of lycopene in tomato skins. Eur Food Res Technol 212:561–565

    Article  CAS  Google Scholar 

  • Pereira CG, Meireles MAA (2010) Supercritical fluid extraction of bioactive compounds: fundamentals, applications and economic perspectives. Food Bioprocess Tech 3:340–372

    Article  CAS  Google Scholar 

  • Prado GHC, Khan M, Saldaña MDA et al (2012) Enzymatic hydrolysis of conjugated linoleic acid-enriched anhydrous milk fat in supercritical carbon dioxide. J Supercrit Fluids 66:198–206

    Article  CAS  Google Scholar 

  • Ramandi NF, Najafi NM, Raofie F et al (2011) Central composite design for the optimization of supercritical carbon dioxide fluid extraction of fatty acids from Borago officinalis L. flower. J Food Sci 76:C1262–C1266

    Article  CAS  Google Scholar 

  • Randolph TW, Blanch HW, Prausnitz JM et al (1985) Enzymatic catalysis in a supercritical fluid. Biotechnol Lett 7:325–328

    Article  CAS  Google Scholar 

  • Rathore V, Madras G (2007) Synthesis of biodiesel from edible and non-edible oils in supercritical alcohols and enzymatic synthesis in supercritical carbon dioxide. Fuel 86:2650–2659

    Article  CAS  Google Scholar 

  • Riha V, Brunner G (2000) Separation of fish oil ethyl esters with supercritical carbon dioxide. J Supercrit Fluids 17:55–64

    Article  CAS  Google Scholar 

  • Rizvi SSH, Benado AL, Zollweg JA et al (1986) Supercritical fluid extraction: fundamental principles and modelling methods. Food Technol Biotechnol 40:55–65

    CAS  Google Scholar 

  • Rodrigues AR, Paiva A, da Silva MG et al (2011) Continuous enzymatic production of biodiesel from virgin and waste sunflower oil in supercritical carbon dioxide. J Supercrit Fluids 56:259–264

    Article  CAS  Google Scholar 

  • Roh M-K, Uddin MS, Chun B-S (2008) Extraction of fucoxanthin and polyphenol from Undaria pinnatifida using supercritical carbon dioxide with co-solvent. Biotechnol Bioproc Eng 13:724–729

    Article  CAS  Google Scholar 

  • Romo-Hualde A, Yetano-Cunchillos AI, Gonzalez-Ferrero C et al (2011) Supercritical fluid extraction and microencapsulation of bioactive compounds from red pepper (Capsicum annum L.) by-products. Food Chem 133:1045–1049

    Article  CAS  Google Scholar 

  • Ronyai E, Simandi B, Tomoskozi S et al (1998) Supercritical fluid extraction of corn germ with carbon dioxide-ethyl alcohol mixture. J Supercrit Fluids 14:75–81

    Article  CAS  Google Scholar 

  • Rozzi NL, Singh RK (2002) Supercritical fluids and the food industry. Compr Rev Food Sci Food Safety 1:33–44

    Article  CAS  Google Scholar 

  • Rubio-Rodriguez N, Beltran S, Jaime I et al (2010) Production of omega-3 polyunsaturated fatty acid concentrates: a review. Innov Food Sci Emerg Technol 11:1–12

    Article  CAS  Google Scholar 

  • Ruen-ngam D, Shotipruk A, Pavasant P et al (2012) Selective extraction of lutein from alcohol treated Chlorella vulgaris by supercritical CO2. Chem Eng Technol 35:255–260

    Article  CAS  Google Scholar 

  • Sahena F, Zaidul ISM, Jinap S et al (2009) Application of supercritical CO2 in lipid extraction—a review. J Food Eng 95:240–253

    Article  CAS  Google Scholar 

  • Sahena F, Zaidul ISM, Jinap S et al (2010) Extraction of fish oil from the skin of Indian mackerel using supercritical fluids. J Food Eng 99:63–69

    Article  CAS  Google Scholar 

  • Sanchez-Camargo AP, Martinez-Correa HA, Paviani LC et al (2011) Supercritical CO2 extraction of lipids and astaxanthin from Brazilian redspotted shrimp waste (Farfantepenaeus paulensis). J Supercrit Fluids 56:164–173

    Article  CAS  Google Scholar 

  • Sanchez-Camargo AP, Meireles MAA, Ferreira ALK et al (2012) Extraction of ω-3 fatty acids and astaxanthin from Brazilian redspotted shrimp waste using supercritical CO2 + ethanol mixtures. J Supercrit Fluids 61:71–77

    Article  CAS  Google Scholar 

  • Sato M, Goto M, Kodama A et al (1998) New fractionation process for citrus oil by pressure swing adsorption in supercritical carbon dioxide. Chem Eng Sci 53:4095–4104

    Article  CAS  Google Scholar 

  • Schütz E (2007) Supercritical fluids and applications—a patent review. Chem Eng Technol 30:685–688

    Article  CAS  Google Scholar 

  • Seifried B, Temelli F (2009) Density of marine lipids in equilibrium with carbon dioxide. J Supercrit Fluids 50:97–104

    Article  CAS  Google Scholar 

  • Shao P, Sun P, Ying Y (2008) Response surface optimization of wheat germ oil yield by supercritical carbon dioxide extraction. Food Bioprod Process 86:227–231

    Article  CAS  Google Scholar 

  • Sheibani A, Ghaziaskar HS (2008) Pressurized fluid extraction of pistachio oil using a modified supercritical fluid extractor and factorial design for optimization. LWT—Food Sci Technol 41:1472–1477

    Article  CAS  Google Scholar 

  • Shen Z, Palmer MV, Ting SST et al (1996) Pilot scale extraction of rice bran oil with dense carbon dioxide. J Agric Food Chem 44:3033–3039

    Article  CAS  Google Scholar 

  • Shen Z, Palmer M, Ting S et al (1997) Pilot scale extraction and fractionation of rice bran oil using supercritical carbon dioxide. J Agric Food Chem 45(12):4540–4544

    Article  CAS  Google Scholar 

  • Shimada Y, Sugihara A, Nakano H et al (1997) Fatty acid specificity of rhizopusdelemar lipase in acidolysis. J Ferment Bioeng 83:321–327

    Article  CAS  Google Scholar 

  • Shimada Y, Fukushima N, Fujita H et al (1998) Selective hydrolysis of borage oil with Candida rugosa lipase: two factors affecting the reaction. J Am Oil Chem Soc 75:1581–1586

    Article  CAS  Google Scholar 

  • Shimada Y, Watanabe Y, Samukawa T et al (1999) Conversion of vegetable oil to biodiesel using immobilized Candida antarctica lipase. Am Oil Chem Soc 76:789–793

    Article  CAS  Google Scholar 

  • Shin S-K, Sim J-E, Kishimura H et al (2012) Characteristics of menhaden oil ethanolysis by immobilized lipase in supercritical carbon dioxide. J Ind Eng Chem 18:546–550

    Article  CAS  Google Scholar 

  • Sovova H, Stateva RP, Galushko AA (2001) Essential oils from seeds: solubility of limonene in supercritical CO2 and how it is affected by fatty oil. J Supercrit Fluids 20:113–129

    Article  CAS  Google Scholar 

  • Spanos GA, Chen HAO, Schwartz SJ (1993) Supercritical CO2 extraction of β-carotene from sweet potatoes. J Food Sci 58:817–820

    Article  CAS  Google Scholar 

  • Stahl E, Schuetz E, Mangold HK (1980) Extraction of seed oils with liquid and supercritical carbon dioxide. J Agric Food Chem 28:1153–1157

    Article  CAS  Google Scholar 

  • Taher H, Al-Zuhair S, Al-Marzouqi AH et al (2011) A review of enzymatic transesterification of microalgal oil-based biodiesel using supercritical technology. Enzyme Res 2011:1–25

    Article  CAS  Google Scholar 

  • Tai HP, Brunner G (2011) Mono- and di-acylglycerol synthesis in CO2-expanded acetone. J Supercrit Fluids 59:87–91

    Article  CAS  Google Scholar 

  • Tang S, Qin C, Wang H et al (2011) Study on supercritical extraction of lipids and enrichment of DHA from oil-rich microalgae. J Supercrit Fluids 57:44–49

    Article  CAS  Google Scholar 

  • Taniguchi M, Tsuji T, Shibata M et al (1985) Extraction of oils from wheat germ with supercritical carbon dioxide. Agric Biol Chem 49:2367–2372

    Article  CAS  Google Scholar 

  • Tao M, Li Q, Qu J et al (2013) Enzymatic synthesis of dipalmitin in supercritical carbon dioxide and mechanism study. Ind Eng Chem Res 52:13528–13535

    Article  CAS  Google Scholar 

  • Taylor SL, Eller FJ, King JW (1997) A comparison of oil and fat content in oilseeds and ground beef using supercritical fluid extraction and related analytical techniques. Food Res Int 30:365–370

    Article  CAS  Google Scholar 

  • Taylor SL, King JW, Montanari L et al (2000) Enrichment and fractionation of phospholipid concentrates by supercritical fluid extraction and chromatography. Ital J Food Sci 12:65–76

    CAS  Google Scholar 

  • Temelli F, Leblanc E, Fu L (1995) Supercritical carbon dioxide extraction of oil from Atlantic Mackerel (Scomber scombrus) and protein functionality. Food Sci Technol Int 60:703–706

    CAS  Google Scholar 

  • Torres CF, Vázquez L, Señoráns FJ et al (2007) An efficient methodology for the preparation of alkoxyglycerols rich in conjugated linoleic acid and eicosapentaenoic acid. J Am Oil Chem Soc 84:443–448

    Article  CAS  Google Scholar 

  • Treyvaud Amiguet V, Kramp KL, Mao J et al (2012) Supercritical carbon dioxide extraction of polyunsaturated fatty acids from Northern shrimp (Pandalus borealis Kreyer) processing by-products. Food Chem 130:853–858

    Article  CAS  Google Scholar 

  • Varma MN, Deshpande PA, Madras G (2010) Synthesis of biodiesel in supercritical alcohols and supercritical carbon dioxide. Fuel 89:1641-–1646

    Article  CAS  Google Scholar 

  • Vázquez L, Torres CF, Fornari T et al (2006) Supercritical fluid extraction of minor lipids from pretreated sunflower oil deodorizer distillates. Eur J Lipid Sci Technol 108:659–665

    Article  CAS  Google Scholar 

  • Vázquez L, Torres CF, Fornari T et al (2007) Recovery of squalene from vegetable oil sources using countercurrent supercritical carbon dioxide extraction. J Supercrit Fluids 40:59–66

    Article  CAS  Google Scholar 

  • Vázquez L, Fornari T, Señoráns FJ et al (2008) Supercritical carbon dioxide fractionation of nonesterified alkoxyglycerols obtained from shark liver oil. J Agric Food Chem 56:1078–1083

    Article  CAS  Google Scholar 

  • Vega PJ, Balaban MO, Sims CA et al (1996) Supercritical carbon dioxide extraction efficiency for carotenes from carrots by RSM. J Food Sci 61:757–759

    Article  CAS  Google Scholar 

  • Vidovic S, Mujic I, Zekovic Z et al (2011) Extraction of fatty acids from Boletus edulis by subcritical and supercritical carbon dioxide. J Am Oil Chem Soc 88:1189–1196

    Article  CAS  Google Scholar 

  • Walker T, Cochran H, Hulbert G (1999) Supercritical carbon dioxide extraction of lipids from Pythium irregulare. J Am Oil Chem Soc 76:595–602

    Article  CAS  Google Scholar 

  • Wang H, Goto M, Sasaki M et al (2004) Separation of α-tocopherol and squalene by pressure swing adsorption in supercritical carbon dioxide. Ind Eng Chem Res 43:2753–2758

    Article  CAS  Google Scholar 

  • Wang Y, Sun D, Chen H et al (2011) Fatty acid composition and antioxidant activity of tea (Camellia sinensis L.) seed oil extracted by optimized supercritical carbon dioxide. Int J Mol Sci 12:7708–7719

    Article  CAS  Google Scholar 

  • Wang H, Liu Y, Wei S et al (2012) Application of response surface methodology to optimise supercritical carbon dioxide extraction of essential oil from Cyperus rotundus Linn. Food Chem 132:582–587

    Article  CAS  Google Scholar 

  • Weber A, Catchpole O, Eltringham W (2008) Supercritical fluid assisted, integrated process for the synthesis and separation of different lipid derivatives. J Sep Sci 31:1346–1351

    Article  CAS  Google Scholar 

  • Wyatt V, Haas M (2009) Production of fatty acid methyl esters via the in situ transesterification of soybean oil in carbon dioxide-expanded methanol. J Am Oil Chem Soc 86:1009–1016

    Article  CAS  Google Scholar 

  • Xu X, Gao Y, Liu G et al (2008) Optimization of supercritical carbon dioxide extraction of sea buckthorn (Hippophae thamnoides L.) oil using response surface methodology. LWT—Food Sci Technol 41:1223–1231

    Article  CAS  Google Scholar 

  • Yu J, Wang J, Liu C et al (2012) Application of response surface methodology to optimise supercritical carbon dioxide extraction of oil from rapeseed (Brassica napus L.). Int J Food Sci Technol 47:1115–1121

    Article  CAS  Google Scholar 

  • Zaidul ISM, Norulaini NNA, Omar AKM et al (2007) Supercritical carbon dioxide (SC-CO2) extraction of palm kernel oil from palm kernel. J Food Eng 79:1007–1014

    Article  CAS  Google Scholar 

  • Zhou D-Y, Tong LEI, Zhu B-W et al (2012) Extraction of lipid from Abalone (Haliotis discus hannai Ino) gonad by supercritical carbon dioxide and enzyme-assisted organic solvent methods. J Food Process Preserv 36:126–132

    Article  CAS  Google Scholar 

  • Zhu B-W, Qin L, Zhou D-Y et al (2010) Extraction of lipid from sea urchin (Strongylocentrotus nudus) gonad by enzyme-assisted aqueous and supercritical carbon dioxide methods. Eur Food Res Technol 230:737–743

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Luis Vázquez .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2015 Springer International Publishing Switzerland

About this chapter

Cite this chapter

Vázquez, L., Torres, C.F. (2015). Lipid Processing and Lipase Activity Under High Pressure Conditions. In: Fornari, T., Stateva, R. (eds) High Pressure Fluid Technology for Green Food Processing. Food Engineering Series. Springer, Cham. https://doi.org/10.1007/978-3-319-10611-3_12

Download citation

Publish with us

Policies and ethics