PL83B1 - A method of making water-soluble, insoluble or sparingly soluble organic materials. - Google Patents
A method of making water-soluble, insoluble or sparingly soluble organic materials. Download PDFInfo
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- PL83B1 PL83B1 PL83A PL8319A PL83B1 PL 83 B1 PL83 B1 PL 83B1 PL 83 A PL83 A PL 83A PL 8319 A PL8319 A PL 8319A PL 83 B1 PL83 B1 PL 83B1
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- PL
- Poland
- Prior art keywords
- soluble
- insoluble
- making water
- organic materials
- sparingly soluble
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000011368 organic material Substances 0.000 title 1
- 239000003925 fat Substances 0.000 claims description 6
- 102000004169 proteins and genes Human genes 0.000 claims description 5
- 108090000623 proteins and genes Proteins 0.000 claims description 5
- -1 organic acid salts Chemical class 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 238000000034 method Methods 0.000 claims 2
- 150000007524 organic acids Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 210000002969 egg yolk Anatomy 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 235000018102 proteins Nutrition 0.000 description 3
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
- 102000002322 Egg Proteins Human genes 0.000 description 2
- 108010000912 Egg Proteins Proteins 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 238000005352 clarification Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
- 230000003165 hydrotropic effect Effects 0.000 description 2
- 239000000787 lecithin Substances 0.000 description 2
- 229940067606 lecithin Drugs 0.000 description 2
- 235000010445 lecithin Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 1
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- 102000011931 Nucleoproteins Human genes 0.000 description 1
- 108010061100 Nucleoproteins Proteins 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940050390 benzoate Drugs 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 235000013345 egg yolk Nutrition 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003752 hydrotrope Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 235000021243 milk fat Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000031787 nutrient reservoir activity Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- ZIRHAFGGEBQZKX-UHFFFAOYSA-N pentyl hydrogen sulfate Chemical compound CCCCCOS(O)(=O)=O ZIRHAFGGEBQZKX-UHFFFAOYSA-N 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229940103091 potassium benzoate Drugs 0.000 description 1
- 239000004300 potassium benzoate Substances 0.000 description 1
- 235000010235 potassium benzoate Nutrition 0.000 description 1
- GHKGUEZUGFJUEJ-UHFFFAOYSA-M potassium;4-methylbenzenesulfonate Chemical compound [K+].CC1=CC=C(S([O-])(=O)=O)C=C1 GHKGUEZUGFJUEJ-UHFFFAOYSA-M 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- XYITYKDGJLHYPW-UHFFFAOYSA-M sodium 2-iodohippurate Chemical compound [Na+].[O-]C(=O)CNC(=O)C1=CC=CC=C1I XYITYKDGJLHYPW-UHFFFAOYSA-M 0.000 description 1
- QUCDWLYKDRVKMI-UHFFFAOYSA-M sodium;3,4-dimethylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1C QUCDWLYKDRVKMI-UHFFFAOYSA-M 0.000 description 1
- KLZYTGLGWPHIDV-UHFFFAOYSA-M sodium;pentyl sulfate Chemical compound [Na+].CCCCCOS([O-])(=O)=O KLZYTGLGWPHIDV-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Description
Znaleziono, ze caly szereg soli i ami¬ dów kwasów organicznych, uzytych juz w malych ilosciach w roztworze wodnym ma zadziwiajaca wlasnosc przeprowadza¬ nia w tenze roztwór nierozpuszczalnych lub trudno rozpuszczalnych w wodzie tluszczów, cial bialkowych jak i produk¬ tów zawierajacych tluszcze i bialko, utrzy¬ mujac je takze na zimno, bez zmiany w stanie rozpuszczonym.Ten prosty sposób przeprowadzania w wodzie nierozpuszczalnych materjalów w latwo rozpuszczalne, moze byc krótko oznaczony jako „hydrotropja", a zwiazki o tej wlasciwej im zdolnosci, jako hy- drotropiczne. Jako hydrotropicznie dzia¬ lajace poznano n. p. sole nastepujacych kwasów: benzoesowego, hippurowego, karbolowego, nitrobenzoesowych, ami¬ no - benzoesowych, halogeno - benzoeso¬ wych, oksybenzoesowyeh,metoksybenzoe- sowych, toluilowego, krezotynowych, fta¬ lowego, dwuoksybenzoesowych, benzolo- sulfinowych i homologów, benzolosulfo- nowych i homologów, naftoesowych, ok- synaftoesowych, naftosulfonowych, nafte- nowych, zywicznych (kwas abietynowy) tiofenokarbonowych, furano- i pirydyno- karbonowych, tluszczowoaromatycznych (fenylooctowy kwas i homologi), niena¬ syconych (typ kwas cynamonowy), oksy- lowych (typ kwas migdalowy), hydro- aromatycznych, (typ szesciohydrobenzo- esowe kwasy), tluszczowych (homologi kwasu octowego), halogenotluszczowych, estrowosiarkowych (typ kwas amylosiar- kowy.Znaleziono dalej, ze prócz soli takze i proste i podstawione amidy wymienio¬ nych kwasów moga dzialac hydrotropicz-nie. Zachowanie to okazuja juz amidy kwasu weglowego i monotioweglowego, mocznik i sulfomocznik.Zwiazki te wykazuja hydrotropjewobec dowolnego rodzaju cial bialkowych, wo¬ bec tluszczów i lipoidów (lecytyny, sub¬ stancji mózgowej, tluszczu mlekowego), wobec zawiesin czesci organów i mikro¬ organizmów.Naturalnie, ze przez odparowanie roz¬ tworu hydrotropicznie dzialajacej soli z rozpuszczonym materjalem, mozna prze¬ prowadzic system w forme stala i przez pózniejsze dodanie wody ponownie roz¬ puscic. Otrzymane roztwory daja sie przeto latwo sterylizowac.Przyklady. 1. 5 g kazeiny rozpuszcza sie klarownie w 40 cm8 50%-eg° roztworu amylosiar- czanu sodowego. Mieszanine mozna za¬ dac równa objetoscia alkoholu n.p.40,0 cm3 alkoholu amylowego bez wystapienia zmetnienia. 2. 20,0 cm3 surowicy skopowej, bydlecej lub ludzkiej mozna po dodaniu równej objetosci 400/o"ego hippuranu sodowego dowolnie gotowac bez wystapienia scie¬ cia, a przeciwnie klaruja sie przytem nawet metne surowice, az do wyjasnienia wodnego.Równie zachowuja sie 50%-°we roz¬ twory mocznika i 339/0-°we tiomocznika, których dodana jest podwójna objetosc. 3. 20,0 cm3 zawiesiny zóltka jaj, otrzy¬ manej przez równomierne wymieszanie 15 g zóltka z 30 cm3 wody, daje przy ogrzaniu z 20 cm3 50%"eg° benzoatu lub krezotynatu prawie klarowny, wytrzy¬ maly na gotowanie roztwór, t. zn., ze prócz protein zóltka rozpuszczaja sie za¬ warte tam lepoidalne materje, lecytyna i oliwa z zóltka. 4. 2,0 g nukleoproteidu pankreasowego rozpuszcza sie w 20,0 cm3 50°/0-ego roz¬ tworu benzoenianu potasowego. Takze ten roztwór mozna gotowac bez wysta¬ pienia wydzielenia. 5.Rozpuszczanie tluszczów potwierdza sie prócz w 3. wspomnianego doswiad¬ czenia z oliwa zóltka i innych, takze tern, ze 100 cm3 nierozcienczonego mhka kla¬ ruje sie za dodaniem 250 cm8 roztworu p-toluolsulfonatu potasu prawie az do • wodnego wyjasnienia. PL PLIt has been found that a whole range of organic acid salts and amides, already used in small amounts in aqueous solution, has the surprising property of converting into a solution of water-insoluble or sparingly water-soluble fats, protein bodies and products containing fats and proteins, by keeping them also cold, without changing their dissolved state. This simple method of making water-insoluble materials readily soluble can be briefly labeled "hydrotropy" and compounds with this inherent capacity as hydrotropic. for example, the salts of the following acids are known: benzoic, hippuric, carbolic, nitrobenzoic, amino-benzoic, halogeno-benzoic, oxybenzoic, methoxybenzoic, toluic, cresotinic, phthalic, dioxybenzoic and benzoic homologues , benzolsulfonates and homologues, naphtha, oxynaphtho, naphthosulfone, naphtha, with resin (abietic acid), thiophenecarbonate, furan- and pyridine-carbonic, fatty aromatic (phenylacetic acid and homologues), unsaturated (cinnamic acid type), oxylic (mandelic acid type), hydroaromatic (hexahydrobenzoic acid type) ), fatty (acetic acid homologues), fatty halide, ester-sulfides (amylsulfuric acid type. It was further found that, apart from salts, also simple and substituted amides of the mentioned acids can act hydrotropically. This behavior is demonstrated by carbonic and monothiocarbon amides, urea and sulfourea. These compounds exhibit hydrotrope against any type of protein body, against fats and lipoids (lecithin, brain substances, milk fat), against organ suspensions and microorganisms. Naturally, by evaporating the hydrotropic salt solution with the dissolved material, the system can be made solid and redissolved by the subsequent addition of water. The resulting solutions are therefore easy to sterilize. Examples. 1. 5 g of casein are clearly dissolved in 40 ml of 50% -eg ° sodium amyl sulfate solution. The mixture may be given an equal volume of alcohol, e.g. 40.0 cm 3 of amyl alcohol, without any turbidity. 2.20.0 cm3 of fossil serum, bovine or human, after adding an equal volume of 400% of ego sodium hippuran, can be cooked freely without the occurrence of cutting, and on the contrary even thin sera clarify until water clarification. % In solutions of urea and 339% in thiourea, to which twice the volume is added. 3.20.0 cm3 of egg yolk suspension, obtained by uniformly mixing 15 g of yolk with 30 cm3 of water, gives on heating With 20 cm3 of 50% of eg benzoate or cresotinate, an almost clear, boiling-stable solution, i.e., that apart from the yolk proteins, the lepoidal materials contained therein, the lecithin and the yolk oil, are dissolved. 4. 2.0 g of pancreas nucleoprotein is dissolved in 20.0 cm 3 of a 50% solution of potassium benzoate. This solution can also be boiled without separating. 5. Dissolution of the fats is confirmed in the third experiment mentioned with olive oil, yolks and others, also the fact that 100 cm3 of undiluted mhk is confirmed by the addition of 250 cm3 of potassium p-toluolsulfonate solution almost until an aqueous clarification. PL PL
Claims (2)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL83B1 true PL83B1 (en) | 1924-05-26 |
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