Posted on Authorea 11 Sep 2020 — The copyright holder is the author/funder. All rights reserved. No reuse without permission. — https://doi.org/10.22541/au.159985362.21997243 — This a preprint and has not been peer reviewed. Data may be preliminary. iy Cheng Xinyi of combination molecular a and by acid palmitoleic of Enrichment ukhr.Teeoe e ukhr upol(P)i osdrdt etebs a aeilfrpalmitoleic for material raw best geographical sea the to the be compared and to cultivation considered obtained, commercial is enrichment. for are (SPO) for suitable acid oil less acid pulp propor- palmitoleic them buckthorn high of making sea distributed contain narrow, yields Therefore, widely that is buckthorn. is extraction plants plants buckthorn low wild these sea up other only of only From contains distribution acid, contains plants, China. buckthorn palmitoleic three oil in sea these of nut potential Of from development tions Macadamia cultivation 2019). oil 2012). al., good of pulp al., et has oil the (Smida et and seed and (Wu acid concen- The palmitoleic 2016), oil low acid. 30% al., the very palmitoleic to (Aquino-Bola˜nos in et in of acid acid usually sources palmitoleic palmitoleic but main 24%-36% 64% origin, the comprises plant are or America, plants Central animal wild of present, ( At oils claw 2012). any cat’s al., almost companies et in nutrition nails, (Wu found trations and and be hair of can biopharmaceutical some skin, acid many preparations; Palmitoleic of present pharmaceutical aging marketed. At and used the successfully products 2011). is delay been health acid anti-inflammatory have al., skin, acid-based which palmitoleic promising the et palmitoleic addition, developing of a (Bal In vigorously elasticity as health 2008). are and al., spotlight eye retention et improve the water (Cao and improve in disorders been to been metabolic (Trico has cosmetics sensitivity ameliorate has tissue in insulin help acid adipose improves may disease, and palmitoleic that metabolic steatosis Consequently, lipid hepatic of 2019). suppresses models al., which animal chemical acid, et in and palmitoleic medicine example, nutrition, release For in to applications 2018). of shown al., range wide et a (Luan demonstrated has industries acid fatty This 2018). al., et (9 or acid, Palmitoleic acid palmitoleic of Introduction preparation the for industries medical and food the studies. by nutritional adoption for for potential concentrate great -20 has method at This (w/v) 56.31%. conditions methanol crystallization optimal to that SPOMFs found 100 various was and of was of It time) ratio effect crystallization scale. 1:15 (w/v), 5-g the solvent a a Subsequently, on to were assessed SPOMFs from acid. were of acid palmitoleic converted temperature) ratio first (distillation 27.17% palmitoleic solvent, distillation was contained temperature, of molecular oil crystallization that enrichment pulp (i.e., study, (SPOMFs) buckthorn crystallization Sea this acids on investigated. fatty In factors was mixed distillation health. corresponding molecular human its and to crystallization to by properties oil beneficial pulp of buckthorn variety sea a shows acid Palmitoleic Abstract 2020 11, September 2 1 nvriyo ense Knoxville Tennessee of University University Jiangnan ° .Teecniin eeuiie ooti iudolcmrsn 41%plioecai iha vrl il of yield overall an with acid palmitoleic 54.18% comprising oil liquid a obtain to utilized were conditions These C. oataunguis-cati Doxantha 1 aiHuang Yaqi , Z -eae--ni cd sa1-abnoea7mnustrtdftyai (Astudillo acid fatty monounsaturated omega-7 16-carbon a is acid, )-hexadec-9-enoic 1 haghagYang Zhuangzhuang , .,awoyvn aiet h mznrifrs,SuhAeiaand America South rainforest, Amazon the to native vine woody a L.), ° o 2h hl h pia eprtr o oeua distillation molecular for temperature optimal the while h, 12 for C 1 1 ogWang Tong , 2 n ioa Wang Xiaosan and , 1 Posted on Authorea 11 Sep 2020 — The copyright holder is the author/funder. All rights reserved. No reuse without permission. — https://doi.org/10.22541/au.159985362.21997243 — This a preprint and has not been peer reviewed. Data may be preliminary. PMst ovn wv n rsalzto ie ieslet eeue opeaetefe at acid fatty free the of prepare to ratio used substrate were solvent, solvents Five temperature, time. crystallization crystallization and were acid (w/v) which fatty solvent SPOMF/mL. The to optimized, mg pressure. SPOMFs 2 were reduced to low- to under diluted parameters by allowed evaporated being removed obtained was Several was after were were sample mixture Samples GC crystals acid. the the by palmitoleic in the analyzed then in solvent was crystallization, rich and In and was composition the solvents, intervals, reactor. that of 1 of time batch fraction end regular ratio mL liquid at the certain the 100 obtain At a a to temperature. with in filtration temperature selected mixed temperature a was controlled at g a crystallize 5 at of performed SPOMFs was general, SPOMFs of crystallization The SPOMFs collected, of was dryness Crystallization acids to was fatty concentrated was solution free extract the containing the Subsequently, -20 layer Then at acids. sulfate. upper fatty sodium The free anhydrous 50 hexane. release using at removed ml to was 300 2 water pH total trace was soaps containing and to with separation. mixture layer acid for lower times saponification hydrochloric collected stand three the to the M extracted and funnel 3 and removed, separating were with a ethanol, phase acidified to hexane 95% transferred was the was mL in mixture matters 40 the unsaponifiable and and The added, KOH were mL) g (200 2.2 hexane with 75 combined at was stirred g) SPO (20 of SPO saponification by (Shanghai, preparation Ltd. acid Co., other Reagent fatty the Free Chemical of Sinopharm All from China). methyl obtained (Shanghai, acid were Regent and fatty China). Chemical pure 37 Sinopharm analytically of ethanol, by were methanol, Standards provided reagents Hexane, were Qinghai). China). (Shanghai, isopropanol (Xining, Ltd. and Ltd. Co., acetone Chemical Co., Sigma-Aldrich from Kangpu purchased Qinghai were esters from purchased was SPO scalable the Materials for source. natural suitable accep- accessible are methods an and methods and achieve inexpensive Materials these an to Importantly, acids from optimized acid. fatty acid were palmitoleic palmitoleic mixed temperature, to of of oil SPOMFs distillation production yield pulp of and the and ratio buckthorn crystallization and concentration solvent, study, sea table time, temperature, this from crystallization crystallization In acid the 2010). (w/v), namely Nag, palmitoleic solvent conditions, and enrich operating (Patil to The acids, preparation fatty used (SPOMFs). scalable unsaturated were for of feasible separation distillation or are molecular concentration few the a compared for only literature 27% the but only in by available increased are was SPO. methods fraction Various crude liquid in the proportion in initial acid the food palmitoleic the with of product in proportion SPO extract the the crystallized However, 15 of acid. (2008) at application Belkacemi acid) Guti´errez the and palmitoleic study, limiting palmitoleic carbamate of 2016), another methyl (41.4% or al., ester In ethyl et the industries. carcinogenic (Solaesa and in pharmaceutical inclusion (˜4%), enriched and urea low urea very highly during and was was formed method distillation be that this may transesterification, of product yield of a overall the process to (81.9%), acid led a acid palmitoleic this in the which although 50% highly of in However, approximately sources, obtain preparation crystallization. natural by the to from increased acid to used was palmitoleic paid trans commonly of concentration enrichment been partial is the has creates reported synthesis attention this (2004) Chemical little Meurer but very sources. acid, however, natural palmitoleic date, from pure To 2020). concentrate al., acid molecular Magallanes et extraction, palmitoleic 2016; Wang fluid al., 2019; et supercritical (Lei al., complexation, et liquid urea preparative and crystallization, transesterification by enzymatic separated distillation, be can acids Fatty ° nartr vprtrt banSOF.Tefia rdc a trdi eldauiu pot aluminum sealed a in stored was product final The SPOMFs. obtain to rotary a on C ° eoeuse. before C ° nawtrbt o .Atrtecmlto fterato,dsildwtr(0 L and mL) (100 water distilled reaction, the of completion the After h. 2 for bath water a in C ° naeoe eutn n˜3 nihetada2%yedo palmitoleic of yield 20% a and enrichment ˜53% in resulting acetone, in C - 2 amtli cd(uloha ta. 00.Kasand Klaas 2020). al., et (Guillocheau acid palmitoleic Posted on Authorea 11 Sep 2020 — The copyright holder is the author/funder. All rights reserved. No reuse without permission. — https://doi.org/10.22541/au.159985362.21997243 — This a preprint and has not been peer reviewed. Data may be preliminary. h olo hssuywst nihplioecai.A hw nTbe2 amtcai stemost the is acid palmitic 2, oleic Table by followed in acids, shown fatty total As of acid. 33.59% palmitoleic for accounting enrich SPOMFs, to the in was acid study fatty saturated this abundant of goal one-way ( and The differences USA), identify IL, discussion to Chicago, and performed Results (SPSS, was 24.0 test) SPSS means Tukey’s as the (ANOVA, expressed difference). using were variance results performed of the were analysis and analyses duplicates, in Statistical out (SD). carried were analyses All equation: following the by calculated was acid palmitoleic standards. FAME of the yield the of The of mixture comparison a by of quantified those and analysis with identified Statistical were peaks FAMEs sample The the min. of 23.875 was times program retention entire 230 the to of time increased and was injector temperature 0.25 The the x USA). mm Agilent, 165 0.25 (7820A, to chromatograph x increased gas m 250 were a (30 temperatures in column FID FAME and mounted DB-Fast min, (FID) a 5 detector for on flame-ionization The rpm separated mL). 8000 were (2 FAMEs at hexane analysis. centrifuged The with (GC) sulfate, extracted chromatograph sodium were gas (FAMEs) anhydrous for over esters (BF methyl used dried acid trifluoride and then fatty separated boron resulting was 25% The layer using upper min. achieved 3 was for degC mg) 70 (50 SPOMFs of Esterification analysis composition calculated. acid was Fatty acid palmitoleic 70 of were of yield and temperature the fixed, feed and were a parameters rpm, operation 400 10 of other Germany).of The speed acid. rotation Alzenau-Hoerstein, palmitoleic a 95 GmbH, follows: of from as UIC proportion temperature high 1, evaporation a (KDL the containing using varying evaporator enriched liquid further performed glass was was crystallization standard distillation two-step a Molecular the from in obtained distillation 2 fraction molecular liquid in acid palmitoleic and 2 The below) fraction (see liquid analyzed of was composition distillation calculated. acid Molecular was fatty acid The palmitoleic 2. of fraction -40 liquid yield crystallization at giving the secondary conducted liquid, a was the 1, crystallization from fraction Secondary separated liquid acid. the palmitoleic in of remained for concentration ° variables further acids response for fatty main conducted saturated the was of amount as in small held used outlined a was were were is As content parameter others experiments acid this optimization the palmitoleic of these optimized, of value for time being enrichment optimal optimization. design crystallization was and the the The The yield parameters parameters. completed, 1:18. The these other was to 1. of of optimization Table 1:9 optimization one parameter was the While one investigation for h. After for used level. 16 range fixed to best a h the at 4 that from temperature found increased was Crystallization was it isopropanol. and and 0 used, acetone of were ethanol, range methanol, the hexane, in was were they and solutions, ymxn iudfato ih2 Lmtao o eido ie h eutn rsaswere crystals resulting The time. of period a for methanol mL 20 with 1 fraction liquid g 5 mixing by C -3 bradacnesrtmeaueo 5dg.Fnly h opsto fftyaiswsanalyzed was acids fatty of composition the Finally, degC. 55 of temperature condenser a and mbar il fplioec()= (%) palmitoleic of Yield ° a aeo 40 of rate a (at C ° o-40 to C ° ,teiiilclm eprtr a ananda 80 at maintained was temperature column initial the C, ° .Sxdffrn PMst-ovn aisi h ag f13t :8(w/v) 1:18 to 1:3 of range the in ratios SPOMFs-to-solvent different Six C. ih fplioecai ntesatn material starting the in acid palmitoleic of eight W ° /i) olwn hc twsmitie t165 at maintained was it which following C/min), ° a aeo 4 of rate a (at C ih fplioecai nafraction a in acid palmitoleic of eight W 3 ° /i)adhl t20fr4mn h running The min. 4 for 230 at held and C/min) ° ,afe aeo Lmn aumlevel vacuum a mL/min, 1 of rate feed a C, 3 nmtao 2m)at mL) (2 methanol in ) μ ° o110 to C ° )adqatfidb a by quantified and m) ( o . i n then and min 0.5 for C ± g ° ) p o i.Finally, min. 1 for C tnaddeviations standard < ( g ) % significant 5%, ° ooti a obtain to C × 100 Posted on Authorea 11 Sep 2020 — The copyright holder is the author/funder. All rights reserved. No reuse without permission. — https://doi.org/10.22541/au.159985362.21997243 — This a preprint and has not been peer reviewed. Data may be preliminary. rvossuyi ossetwt h eut fti xeiet ti ocue hthxn a o the not was hexane (Vazquez that crystallization concluded low-temperature by is acids It fatty experiment. free this of solvents. concentration of three the results these for among the solvents acetone, found with suitable were hexane, fraction level consistent Therefore, most the by acid in followed solvents. is palmitoleic acid 1, other study in palmitoleic fraction of differences with Previous increase insignificant liquid the those and the ethanol, limited than in and very isopropanol was higher acid acetone, palmitoleic significantly For ethanol. palmitoleic of was and the content which isopropanol solvent, highest crystallization 38.55%, the the to gave as -20 methanol up used at was solvent was methanol mL content When less 2017). 60 enrichment. Initially, acid al., acid. is and acid palmitoleic et palmitoleic solvent, SPOMFs of (Zhu on yield g nonpolar plants and type 5 content a crushing the with on oilseed Hexane, type performed in industry. solvent were solvent of food effect extraction the polar in the shows a 2a solvent as acids Figure Acetone, used fatty permitted solvent widely free 2019). a and and 2 al., is triglycerides methanol Class et of It than separation (Kameyama a toxic 2012). the ppm is for Akoh, solvent 3000 Methanol and crystallization cry- of (Vazquez (USP). as acid selected limit Pharmacopoeia fatty commonly concentrations concentration is States free allowable residual solvent, United the an (ppm) the for with parts-per-million to examined at associated according were permitted isopropanol pharmaceuticals are acetone, solvents in These ethanol, fractionation. methanol, stallization hexane, study, this In -20 and types at temperature, solvent optimum crystallization process. various the the crystallization of as results, following Effect determined the agree- these was in in on yields used are Based reasonable was results 2017). and The temperature al., contents this temperature. acid et low palmitoleic (Zhang very high the study -40 had at previous at formed a lowest crystals with the acid was ment fatty 1b, more of Figure removal because in 0 temperature the shown and causing as (-20 temperature, acid, lower 2016). temperatures palmitoleic a al., of et at yield (Mu solution The fraction the liquid from the acid from palmitoleic acid palmitoleic of In crystallization content. the initial to the -20 than the at ° higher When obtained significantly b. product and were 1a acid which 0 Figure respectively, palmitoleic in 33.82%, the shown crystals and addition, as few 38.55% SPOMFs, only to to that increased compared -20 the observed solvents at of was two conducted was in goal It crystallization slightly main temperature. increased the crystallization only 0 Therefore, of was SPOMFs acetone) 35.48%. at effect and in was (methanol the formed acid solvents acids two examine were study, palmitic fatty this in to of In saturated content remain acids. selected fatty the will of were saturated remove that contents acids a to shows was fatty total in 2 process unsaturated the crystallization stored Table and 2012). and then solvent Akoh, crystallization and 33.59%, in and solvent undergo was solubility (Vazquez lower selected will fraction and a temperature, liquid points with low melting the mixed higher a have were at which acids acids, particularly fatty fatty free saturated temperature, the (0 reduced When temperature investigated. crystallization was of yield to effect distillation the molecular to First, temperature subject was crystallization 2 the fraction of liquid product. -40 Effect the final at remained Then, acid performed still 2. palmitoleic was stage fraction acids concentrated crystallization liquid crystallization fatty a secondary the saturated yield first a in residual thus the resulted 1, Some during this type, fraction crystallization. and time solvent liquid of crystallization then collected results and the and the in (w/v) improve evaluated, solvent to was to optimized crystallization SPOMFs were low-temperature of for ratio temperature substrate optimal the First, (27.17%). acid palmitoleic and (32.16%), acid ,tecneto amtli cddcesdsihl oprdt hta -20 at that to compared slightly decreased acid palmitoleic of content the C, ° eadeso hc ovn a sd oee,we h rsalzto a ute erae o-40 to decreased further was crystallization the when However, used. was solvent which of regardless C ° .Atog h ilso amtli cdwr ih h otn fplioecacid palmitoleic of content the high, were acid palmitoleic of yields the Although C. ° ) h il fplioecai hwdasgicn euto ihdecreased with reduction significant a showed acid palmitoleic of yield The C). ° ,telvl fplioecai sn ehnladaeoea solvents as acetone and methanol using acid palmitoleic of levels the C, ° ,-20 C, 4 ° a infiatyhge otn oprdto compared content higher significantly a had C ° ,ad-40 and C, ° o 2ht netgt h ffc fsolvent of effect the investigate to h 12 for C ° )o amtli cdcnetand content acid palmitoleic on C) ° oprdt ilsa other at yields to compared C ° .Terslsmgtb due be might results The C. ° ormv these, remove to C ° that C Posted on Authorea 11 Sep 2020 — The copyright holder is the author/funder. All rights reserved. No reuse without permission. — https://doi.org/10.22541/au.159985362.21997243 — This a preprint and has not been peer reviewed. Data may be preliminary. h otn fplii cdwssgicnl eue,fo .7 o21%i hsfato.Therefore, 40.55% fraction. from fraction, this 95.49%. liquid of in of the purity 2.13% yield in the content to a 2, acid 9.37% with palmitoleic Table from 45.22%, of in was reduced, increase shown significant crystallization significantly As a secondary was to degC. by acid led -40 2 palmitic re-crystallization at fraction of re-crystallization has liquid content after the it these The acid. collected on However, in palmitic Based was acid remove acid. 2 2017). palmitoleic to al., palmitic fraction performed et was from liquid (Jin 1 acid A purity fraction palmitoleic the liquid improve palmitoleic separate of much further crystallization separate cannot as can secondary removed only but fractionation are considerations, can multistage acids, carbons distillation 1 that [?]16 fatty molecular fraction proven having subsequent C18 liquid acids been for because fatty the the accounting the fraction 2, abundant, from that liquid Table most important acid the the in is from being It shown possible acid acids. As fatty palmitic as conditions. composition total with acid optimal the acids, fatty of fatty the the 9.37% saturated under stage, of obtained contents first was low the contained 1 at conditions fraction crystallization liquid significantly. of of yield optimization its the completing reducing 1 After acid, complete fraction palmitoleic almost liquid the was slight of of crystallization only . crystallization crystallization . that were . Secondary the best. suggesting There to the 41.55%. h, is lead to 16 time 27.17% will to what from time h time Add ranged Longer 12 crystallization acid h. from the palmitoleic 16 of purity When of purity at time. acid purity the the with Overall, palmitoleic 2c. h, decreased in Figure 16 yield increases in to the shown 4 as whereas from acid time, palmitoleic ranged with with of investigated increased yield were and h) acid process purity 16 palmitoleic -20 crystallization the and at the h on 1:15 12 in influence h, of significant phases 8 a ratio liquid h, methanol and (4 to solid times SPOMFs crystallization the four the between Thus, transfer 2016). mass al., the et (Morales-Medina on influence an has 88.47% Time an studies. to time crystallization translates crystallization further that of for obtained, Effect was used the acid was gave palmitoleic (w/v) (w/v) 40.43% 1:15 1:15 1:15. yield. of with of and acid ratio solution 1:12 ratio palmitoleic methanol a of methanol to conditions, ratios to SPOMFs these methanol SPOMF an Under to an acid, SPOMFs Hence, palmitoleic between result. of found yield best was and SPOMFs difference purity indicating volume. the significant both solvent decreased, as no Considering high solution However, yield, the in of 2016). to acid terms (Shahidi, due palmitoleic In methanol acids crystallization of fatty the effective proportion saturated the of the the to use 1:15, of due volume beyond solubilization is purity high changed This the ratio at 1:15, 40.43%. methanol to acid to 1:9 to fatty 36.32% from changed from saturated was increased (w/v) the methanol solution of to acid SPOMFs solutions palmitoleic of SPOMF ratio the methanolic the of the when 2b, and Figure (w/v), in 1:18 the shown At and Therefore, monitoring. 1:15 2b. allow 1:12, Figure -20 to 1:9, in quickly at at relative shown too stored set froze acid are were were solution results ratios palmitoleic the methanol the (% because to and inappropriate, purity SPOMF were investigated, on 1:6 were to (w/v) acid -20 1:3 at solvent palmitoleic from out of to carried yield was SPOMFs crystallization and of When acid) ratio fatty the total among (w/v) to of yield solvent for effects in to solvent the SPOMFs difference optimal Subsequently, of an statistical as ratio no selected the is liquid was of There methanol the Effect account, 2a. applied in into treatments Figure acid yield the treatments. in by and palmitoleic crystallization affected shown purity further as of both are acid proportion taking palmitoleic results Thus, of highest the solvents. yields the The and improved. to compared be to were led needs methanol yield the in fraction, crystallization the Although 2011). Akoh, and ° o 2h. 12 for C ° ,orpeiiaysuysoe htSOF:mtao ratios methanol SPOMFs: that showed study preliminary our C, ° .I a bevdta h hneo rsalzto iehad time crystallization of change the that observed was It C. 5 Posted on Authorea 11 Sep 2020 — The copyright holder is the author/funder. All rights reserved. No reuse without permission. — https://doi.org/10.22541/au.159985362.21997243 — This a preprint and has not been peer reviewed. Data may be preliminary. h uhr elr htte aen oflc finterest. of conflict No.: no (Grant have they China that declare of authors Foundation The Science Natural interest of “National Conflict by 31701559)”. supported No.: Grant financially and 31972035 was and study food the This for acid fatty unique fraction this acid raw of Acknowledgements palmitoleic the a process concentrated as to scale-up enriched a lead industrial as obtaining can for twice industries. basis for degC was be provides pharmaceutical 100 method which source to at effective 56.31%, natural performed of an found a distillation yield of from was molecular a demonstration Methanol in Then, This acid h. The palmitoleic material. acid. 12 54.18% temperature crystallization. of palmitoleic contains crystallization by time a that of incubation solution (w/v), distillate 1:15 and in proportion of degC, concentration ratio high -20 methanol acid a of SPOMFs: palmitoleic were containing leading increase conditions distillation, liquid crystallization to optimal molecular solvent a and organic of crystallization optimum combining yield the by high enriched a was acid to palmitoleic study, in this obtained, was In acid degC palmitoleic 100 of at combining liquid by 54.18% pure Conclusions Thus, was was 54.18% it distillation. 56.31%. a acid for while of distillation, palmitoleic temperature ˜54%, yield and best of was overall the crystallization distillate 65%) an was of the degC (about steps of 100 yield Accordingly, above purity greater the the 63.64%. a degC, of yield 110 increased, a to was 17.79%. with At degC temperature was 100 distillate. distillate the At were the to the as in obtained. acid of degC that going yield 120 shows palmitic products the at 3 all and but set Table almost achieved, acid first to was was myristic led separation temperature this some as Unfortunately, evaporation degC, such study, separation. 95 10 this acids of of in effect fatty level vacuum the feedstock temperature. saturated investigate a the proper under 2016), in a degC under difference al., 125 distillate composition at et distillation the distillate the in (Solaesa the and collected in by point, be evaporated would boiling study acid its a palmitoleic affect while acid In fatty residue a the Thus, with of in but bonds remain crystallization. acid 2. double carbons by palmitoleic fraction of separate more is number liquid two to the order the acid. difficult having and in palmitoleic length are acid former chain of was acids palmitoleic the The 2 proportion enrich fatty with fraction to two the liquid acid, applied These as the was palmitoleic same in distillation bond. to acid the molecular double oleic structure approximately one the in was containing that similar which shows both 2 is acids, Table fatty acid 2018). total Oleic al., residence free the the et mean and Zhang of different temperature 2016; with 45.06% evaporation partial Compounds al., the and et decreases 2018). weight which (Solaesa al., molecular condition, et time vacuum different (Zhang under with homologs separated mixtures of are separation of paths the separation for the and for pressure, enrichment used vapor be acid of can palmitoleic distillation steps on Molecular two temperature after distillation molecular 97.52% by molecular reached purification of 2 further Effect fraction for material liquid enriched in sufficiently content obtained liquid distillation. acid had the fatty values. we in Finally, percentage acids unsaturated fatty relative the crystallization. saturated in relative thus of increase are proportion and contents to the these tend phase, decreased the that will significantly in others crystallization noted and removed, secondary that acid be Overall, is linoleic from should of acid differed It fatty proportions significantly crystallization. the one 1 in secondary If fraction found after percentages. liquid were solution differences the in significant in acid statistically content linolenic no acid and oleic 2, the fraction liquid addition, In 45.22%. to > li cd[]lnli cd(hn ta. 03.Tu,oecai sepce to expected is acid oleic Thus, 2013). al., et (Zhang acid linoleic [?] acid oleic 6 -3 br hs osdrn h at acid fatty the considering Thus, mbar. Posted on Authorea 11 Sep 2020 — The copyright holder is the author/funder. All rights reserved. No reuse without permission. — https://doi.org/10.22541/au.159985362.21997243 — This a preprint and has not been peer reviewed. Data may be preliminary. md,I,Pneec,C,Pneec,O,Sedn . lveo . erc . aaa-hcoi Z. Tamanai-Shacoori, & V., Meuric, N., Oliviero, Microbiology A., Applied ( Sweidan, buckthorn of sea O., Wiley. of Pentelescu, (USA): Benefits York C., (2019) New Pentelescu, ed.). I., by-products. oil (6th Smida, and Products acids Fat fatty of and purification Oil and isolation Industrial for Bailey’s techniques separation Novel pomace. (2005) seabuckthorn F. from Shahidi, Technology concentrate and ester Science acid palmitoleic Lipid A of (2004) U. Journal P. waste. Meurer, processing & fish M., and Klaas, Society poultry Chemists’ from concentrates Oil PUFA American of Production the (2010) of A. DHA Nag, and & n-6 DPA D., of Patil, Enrichment (2016) X. Wang, & Q. Jin, Research X., Wang, Y., Zhang, of Y., modeling from Li, transfer H., Zhang, Mass H., (2016) Mu, crystallization. E. temperature Guadix, low by & concentration A., (PUFA) Engineering Guadix, acid Food fatty M., polyunsaturated Munio, oil G., sardine Leon, cod De associated in R., inversely acids Morales-Medina, adults. is acid fatty Rican palmitoleic omega-3 Costa tissue of in Adipose Enrichment infarction (2018) Diseases (2016) A. myocardial Baylin, T. acute & Li, nonfatal H., & with Campos, of D., Y., Wang, interesterification. J. convergence D., enzymatic Lee, Luan, further and Y., winterization the solvent Wei, Toward alternate H., via Zhang, oil States: Comparative liver S., (2019) United Ba, S. the Q., Miyazaki, and Lei, & Europe, T., Ando, Japan, standards. R., pharmacopoeial in sn-1,3- Saito, international of pharmacopoeias C., Production of Mizumaru, (2017) X. study M., Wang, Matsuhama, Y., . . 2-methylpentane . Kameyama, using X., fractionation Wang, selective D., by Xie, isohexane. fat J., kernel based Zhang, mango M., from W. fats Pembe, distearoyl-2-oleoyl-glycerol-rich L., Zheng, J., Jin, ( seabuckthorn of enrichment acid Palmitoleic (2008) L. K. Belkacemi, A & F., synthesis. L. chemical Gutierrez, and n-7): methods trans-C16:1 analytical or data, (trans-9-C16:1, compositional acid review. Trans-palmitoleic origin, (2020) metabolism. metabolism, V. systemic impacts, Identification Rioux, (2008) to Nutritional & S. tissue P., G. Legrand, adipose Hotamisligil, valuable E., & linking Guillocheau, M., of hormone S. source Watkins, lipid potential M., a M. A lipokine, Wiest, a berries: R., J. buckthorn of Mayers, Sea K., (2011) (2018) Gerhold, H., S. J. Cao, Satya, Balsinde, & cosmoceuticals. N., & and S. nutraceuticals A., Naik, for V., M. nutrients Meda, Balboa, M., P., L. cells. Bal, Lebrero, phagocytic L., in isomers Pereira, acid C., palmitoleic of , Guijas, activity C., biological ofMacadamianut. and Meana, varieties Occurrence nine M., from A. J., oil Astudillo, A. of Martinez, profile L., Properties Food acids J. Fatty of Chavez-Servia, Journal T., (2016) S. I. Martin-del-Campo, Verdalet-Guzman, L., & Mapel-Velazco, N., E. Aquino-Bolanos, References 59 upolb rsalzto process. crystallization by oil pulp ) :237-249. ciohtimsp. Schizochytrium Biochimie , , 28 55 :973-979. :737–746. odChemistry Food , , 183 169 :16-23. , i ylwtmeauesletcrystallization. solvent low-temperature by oil :144-160. 126 , 20 :1594-1605. :1262-1269. ippa rhamnoides Hippophae , 234 , :46-54. eaainSineadTechnology and Science Separation 88 hmcl&Pamcuia Bulletin Pharmaceutical & Chemical , 106 :589-593. :412-416. odRsac International Research Food 7 upolbsdmuhaho rlhealth. oral on mouthwash oil-based pulp ) urto,Mtbls Cardiovascular & Metabolism Nutrition, nutil&EgneigChemistry Engineering & Industrial , 43 odChemistry Food Cell , 44 , :2003-2022. 67 :1718-1727. ora fLpdResearch Lipid of Journal , 134 :1301-1313. ippa rhamnoides Hippophae :933-944. , 199 International ora of Journal European :364-371. Journal Journal Posted on Authorea 11 Sep 2020 — The copyright holder is the author/funder. All rights reserved. No reuse without permission. — https://doi.org/10.22541/au.159985362.21997243 — This a preprint and has not been peer reviewed. Data may be preliminary. ee ovn rsalzto ovn rsalzto ovn rsalzto ovn rsalzto eodr rsalzto oeua distillation Molecular crystallization Secondary crystallization Solvent crystallization Solvent crystallization Solvent crystallization Solvent Level distillation molecular and methanol crystallization mL (w/v), 75 h 1 1:18 4 Table SPOMF, to of g 1:9 time 5 crystallization of Tables degC, ratio of (c): -20 methanol List of h; to temperature 12 SPOMF crystallization of of h. SPOMF, (w/v)], temperature 12 time g 1:15 crystallization to ratio 5 crystallization (w/v)], methanol degC, 1:12 (b): to ratio -20 [SPOMF h; solvent of 12 [SPOMF: temperature of solvent crystallization time mL the crystallization 60 as SPOMF, degC, acetone g -20 and 5 methanol (a): (w/v)], ditions 1:12 Crystallization ratio 2 solvent (b). Figure stage [SPOMF: h. crystallization solvent 12 first mL of the time 60 at crystallization SPOMF, acid solvents, g palmitoleic 5 the of conditions: yield on temperature tallization 2- of 1 Figure concentration and Synthesis crystallization. captions (2018) two-step a Figure X. by 1,2-diacylglycerols Research Wang, of Chemistry Purification & (2017) Engineering X. Wang, & Q., & Industrial X., Jin, Wang, Q., S., Jin, Y., Zhu, Zou, acids. fatty D., polyunsaturated Xie, in rich X., monoacylglycerols Wang, Y., fatty unsaturated Zhang, highly of concentration of One-Step (2017) oil X. Wang, from :475-483. & acids Y., Li, fatty from D., acids Xie, polyunsaturated X., omega-3 Wang, Y., of Zhang, Concentration (2013) Research Y. Chemistry Liu, Engineering & limacinum J., Schizochytrium Liu, produc- G., palmitoleate industry. of Zhang, sustainable engineering and metabolic health and human Biosynthesis to fatty (2012) :340-349. contributor chain F. important D. branched Hildebrand, an of & tion, Enrichment R., (2020) Li, X. Y., Wang, Wu, use. formula & infant Q., for Jin, complexation 10.1016/j.lwt.2019.108627 W., urea doi: Jin, via lanolin C., from Yang, temperature acids X., low by Wang, oil X., soybean Wang, modified in acid stearidonic ethyl of Enrichment acid (2012) fatty C. crystallisation. C. and Akoh, acid & fatty L., Vazquez, free in acid winterization. stearidonic by of oil 1785. Concentration soybean (2011) modified associated C. from is C. forms Akoh, acid & palmitoleic L., Circulating individuals. Vazquez, non-diabetic (2019) in A. tolerance Natali, glucose & and function A., concentration :206–218. cell Mari, and beta L., sensitivity, Production insulin molecular Nesti, with (2016) and A., Z. glycerolysis Mengozzi, Guo, enzymatic D., by Trico, & acids S., fatty Beltran, polyunsaturated M., omega-3 Falkeborg, distillation. in T., rich M. monoacylglycerols Sanz, of G., A. Solaesa, X xeietldsg o piiaino amtli cdprfiainb obnto fsolvent of combination a by purification acid palmitoleic of optimization for design Experimental 1 h ffc fcytliaintmeaueo otn fplioecai a n h ffc fcrys- of effect the and (a) acid palmitoleic of content on temperature crystallization of effect The piiaino rsalzto odtosa h rtcytliainsae rsalzto con- Crystallization stage. crystallization first the at conditions crystallization of Optimization Tuna ( odChemistry Food ° )X C) odChemistry Food i ylwtmeauecrystallization. low-temperature by oil ymlclrdsilto:otmzto ftcnlgclconditions. technological of optimization distillation: molecular by , 190 , , 130 2 52 :960-967. :3918-3925. :147-155. , 56 ora fteAeia i hmssSociety Chemists Oil American the of Journal :2197-2204. 8 odChemistry Food ora fteAeia i hmssSociety Chemists Oil American the of Journal X 3 wv X (w/v) W-odSineadTechnology and Science LWT-Food , 250 rgesi ii Research Lipid in Progress :60-66. 4 h X (h) Diabetologia nutil& Industrial , 88 , :1775- 117 , , , 51 94 63 . 1 ( ° )X C) 1 ( ° C) Posted on Authorea 11 Sep 2020 — The copyright holder is the author/funder. All rights reserved. No reuse without permission. — https://doi.org/10.22541/au.159985362.21997243 — This a preprint and has not been peer reviewed. Data may be preliminary. palmitoleic-acid-by-a-combination-of-crystallization-and-molecular-distillation Figure.docx at difference 110 significant are letters file different Hosted with row same the 105 in Values 100 detected; not ND, 95 -40 at difference significant are letters 3 different Table with row 16 same acid; the linolenic in + Values acid linoleic + detected; acid not oleic 12 acid; ND, + stearic acid + UFA=palmitoleic acid 8 acids. palmitic fatty + unsaturated 4 UFA, acid myristic SFA= acids, fatty saturated SFA, 18 1: 15 1: 12 1: 9 1: isopropanol Hexane acetone ethanol methanol 2 Table X distillation Molecular crystallization -40 Secondary 5 -20 crystallization Solvent 4 0 crystallization Solvent 3 crystallization 2 Solvent 1 crystallization Solvent Level 1 rsalzto eprtr,X temperature, crystallization = tai cdN DN DND ND ND ND 0.75 45.06 ND acid Oleic 95 acid 2.13 45.22 Stearic 2 ND acid fraction Palmitoleic Liquid acid Palmitic acid Myristic acid Fatty il % D17.79 ND 2.50 5.11 (%) Yield acid Linolenic acid Linoleic at cdcmoiino h itlaeb oeua distillation molecular by distillate the of composition acid Fatty distillate the and 2 fraction liquid 1, fraction liquid SPOMFs, of composition acid Fatty at cdSOF iudfato iudfato h distillate The 2 fraction Liquid 1 fraction Liquid 0.37 SPOMFs acid Myristic acid Fatty amtcai 33.59 acid Palmitic ioecai 3.50 32.16 1.52 acid Linoleic acid Oleic acid 27.17 Stearic acid Palmitoleic ioei cd1.70 acid Linolenic F 64.53 35.48 UFA SFA vial at available ± ± ± ± ± https://authorea.com/users/355737/articles/478871-enrichment-of- 0.08 0.11 0.13 0.18 0.12 ± ± ± ± ± ± ± ± ± a c c 0.01 0.05 0.05 0.05 c a 2 0.12 0.02 0.01 0.04 0.23 ovn ye X type, solvent = a a b a c b a a c 0.44 9.37 5.02 41.33 0.40 40.55 2.34 89.24 10.21 28.47 58.4 8.09 1.46 2.91 ° 100 C ± ± ± ± ± ± ± ± ± ± ± ± ± ± ± ± 0.02 0.06 0.28 0.11 0.04 0.13 0.01 0.06 0.07 0.03 0.16 0.48 0.32 0.03 0.06 1.56 9 b b b a b c a b a a a c b b a a 3 ai fSOF oslet X solvent, to SPOMFs of ratio = 54.18 0.74 31.66 7.92 63.64 1.76 3.76 ± ± ± ± ° D0.74 ND 45.06 45.22 2.13 DND 5.11 ND 97.52 2.13 2.50 105 C ± ± ± 0.01 0.22 0.05 0.06 0.27 0.38 1.43 ± ± ± ± ± ± ± a b b b 0.08 0.13 0.08 0.11 b b b 0.18 0.12 0.11 p p a b a b 53.56 32.44 0.71 7.66 65.65 1.79 3.86 d b c < < 0.05 0.05 ± ± ± ± ° 110 C ± ± ± 0.05 0.14 0.00 0.08 0.61 0.71 1.74 31.66 54.18 7.92 3.76 8.66 1.76 91.36 a b b b b b b ± ± ± ± ± ± ± ± 53.49 0.67 32.61 7.57 64.14 1.8 3.87 0.01 0.22 0.06 0.23 0.05 0.38 0.27 0.22 4 ± time. = ± ± ± ° c b a b a 0.01 C ± ± ± a c a 0.00 0.01 0.06 0.51 0.47 1.13 b a b b b b b