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WO2005077930A1 - Purification de composes phenoliques - Google Patents

Purification de composes phenoliques Download PDF

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Publication number
WO2005077930A1
WO2005077930A1 PCT/US2005/004160 US2005004160W WO2005077930A1 WO 2005077930 A1 WO2005077930 A1 WO 2005077930A1 US 2005004160 W US2005004160 W US 2005004160W WO 2005077930 A1 WO2005077930 A1 WO 2005077930A1
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Prior art keywords
phenolic compound
percent
starting material
insolubles
solution
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PCT/US2005/004160
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English (en)
Inventor
Ian Purtle
Aharon Eyal
Asher Vitner
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Cargill Inc
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Cargill Inc
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
    • C07D311/40—Separation, e.g. from natural material; Purification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
    • C07D311/34—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 3 only
    • C07D311/36—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 3 only not hydrogenated in the hetero ring, e.g. isoflavones

Definitions

  • the present invention generally relates to a method of purifying a phenolic compound.
  • the present invention more particularly relates to a process for the purification of a starting material resulting from a biological source. More particularly, the present invention relates to a process for the purification of a starting material resulting from a biological source wherein the starting material comprises a mixture of at least one phenolic compound and at least one non- phenolic impurity. More particularly, the present invention relates to a process for purifying a phenolic compound such as isoflavones from plant materials such as soybean extracts.
  • Soy solubles contain three families of isoflavones: genistin, daidzin and glycitin. Each family may appear in four forms: aglycones, glycosides, malonyl glycosides, and acetyl glycosides (the malonyl and acetyl glycosides are also referred to as conjugates). Most of the isoflavones in the solubles are in the forms of malonyl glycosides and glycosides.
  • the present invention relates to a process for improving the purity of a phenolic compound from a starting material of a biological source.
  • the process comprises providing the starting material from the biological source comprising a mixture of at least one phenolic compound having a purity P1 and at least one non-phenolic compound.
  • the process also comprises forming at least a fraction of the starting material, an alkaline aqueous solution having at least a pH of about pKa minus 1.5, wherein the pKa is that of the at least one phenolic compound, and insolubles.
  • the process also comprises separating the insolubles from the alkaline solution, whereby there is formed a purified solution comprising at least one purified phenolic compound having a purity of P2 and insolubles containing the at leas one non-phenolic compound wherein P2 is greater thatn P1 and the insolubles contain less than about 20 percent (%) of the at least one phenolic compound present in the starting material.
  • the present invention also related to a process for improving the purity of a phenolic compound from a starting material of biological source.
  • the starting material comprises a mixture of at least one phenolic compound and at least one non-phenolic compound.
  • the starting material is characterized in that, on adjusting the total concentration of the solutes of the starting material, in an aqueous medium at a pH of up to about 8, to a concentration of between about 10 percent (%) and about 40 percent (%), the non-phenolic compound presents as a first precipitate, and in that weight ratio, R1 , of the first parcipitate, when dried, to the phenolicompound in the starting material, is at least 1.5:1.
  • the process comprises forming at least a fraction of the starting material, an alkaline aqueous solution having a pH of at least about pKa- 1.5, wherein the pKa is that of the at least one phenolic compound, a and total solutes concentration of between about 1 percent (%) and about 40 percent (%), 5 and insolubles containing the non-phenolic compound, wherein a weight ratio, R2, of the insolubles, when dried, to phenolic compound in the starting material is at least about 10 percent (%) of R1 , and wherein the insolubles contain less than about 20 percent (%) of the phenolic compound present in the starting material.
  • FIGURE 1 is a flow diagram of a method of purifying a phenolic compound according to an exemplary embodiment.
  • the starting material contains a phenolic compound according to a preferred embodiment, preferably a polyphenol, more preferably a flavonoid, most preferably an isoflavone.
  • the starting material also contains at least one non-phenolic compound according to ao preferred embodiment.
  • the starting material is an extract of plant material, preferably an extract of soy material.
  • the starting material is soy solubles (22) resulting from a process for protein purification (20).
  • a soy material (12) preferably5 soybean meal (SBM) or defatted and flash-desolventized soy flakes (DFWF) is contacted with water (14) and optionally also with an organic solvent.
  • purified soy proteins (24) are separated using methods such as filtration, centrifugation, precipitation, decantation and membrane filtration, e.g. ultrafiltration.
  • the polyphenol e.g.
  • isoflavone may be separated from soy solubles by adjusting the solution concentration of the soy solubles to between about 10 percent (%) and 40 percent (%), more preferably between about 15 percent (%) and 30 percent (%). Such adjustment of concentration induces the precipitation of a solid with increased polyphenol (e.g. isoflavone) purity compared to the soy solubles, typically about 4-7 percent (%) on a solvent-free basis. Typically, polyphenol (e.g. isoflavone) in such precipitate are further purified to 40 percent (%) purity in a costly process such as chromatographic separation.
  • isoflavone includes purifying polyphenols (e.g. isoflavone) in the precipitate so that that precipitate is a suitable starting material.
  • aqueous solution sometimes referred to as soy solubles, soy molasses or soy whey (22).
  • Such solution contains polyphenols (e.g. isoflavone) and many other components, including various carbohydrates (main components), soluble proteins and/or peptides, saponins, mineral salts (ashes), amino acids and other solutes.
  • the concentration of the solution depends on the method of the protein purification. In those cases where an organic solvent is used for protein purification, it is evaporated from the co-product solution along with water to reach a solution of about 50 percent (%) concentration, typically referred to as soy molasses.
  • the solution is dilute, particularly when membrane filtration is used for separating the purified proteins.
  • the solutes are of low molecular weight and end up in the membrane permeate.
  • the permeate is of few percent concentration and is concentrated by reverse osmosis (RO) and/or evaporation according to a preferred embodiment.
  • RO reverse osmosis
  • Other soy solubles suitable for use as a starting material may be obtained by extraction of solubles from defatted soybean germ according to alternative embodiments.
  • the starting material e.g.
  • soy solubles or a precipitate obtained from those is combined with a basic compound in an aqueous medium to form an aqueous solution with pH greater than at least about the isoflavones pKa minus about 1.5.
  • the pKa is that of the stronger acid isoflavone, according to a preferred embodiment.
  • the conditions are adjusted such that insolubles are formed.
  • insolubles as used in thfe disclosure means material that does not dissolve in the solution at the selected conditions.
  • an alkali (26) is added to the solubles (22) and the concentration of the solution is adjusted to between about 1 percent (%) and about 40 percent (%) total solids.
  • concentration adjustment may involve dilution with water or water removal, depending on the concentration of the solubles. Water removal could use e.g. evaporation, multiple-effect evaporation, reverse osmosis and their combination. According to a preferred embodiment, water removal is conducted at a temperature not greater than about 60 degrees Celsius. If the starting material is solid, it is preferably introduced into an alkali solution. Means for facilitating dissolution are preferably applied, e.g. mixing and ultrasound.
  • the total solids concentration in that step is selected so that insolubles exist according to a preferred embodiment.
  • the preferred concentration is a matter of economic optimization based on the cost of water removal and preferred conditions for the recovery of the product.
  • the preferred concentration is typically smaller in the case of a solid starting material than in the case of starting with a solution such as soy solubles.
  • the insolubles formed contain non-phenolic compounds so that the solution is purified with regards to the phenolic compound (e.g. isoflavones) according to a preferred embodiment.
  • the insolubles may contain less than about 20 percent (%) phenolic compound (e.g. isoflavones), typically less than about 10 percent (%), suitably less than about 5 percent (%) and most preferably less than about 1 percent (%) phenolic compound (e.g. isoflavones).
  • Those insolubles are preferably separated (step 40 in FIGURE 1) by means such as centrifugation, filtration, decantation, etc. and various combinations of those.
  • the separated insolubles (42) may be used for various applications, e.g. in animal feed.
  • the purified solution (44) is further treated for separation of the phenolic compound (e.g. isoflavones) according to a preferred embodiment.
  • a preferred method for such separation is lowering the pH of the solution by at least 0.2 pH unit.
  • an acid (46) is added (step 50) to the purified solution (44), whereby insolubles are formed.
  • Those insolubles are enriched in isoflavones, i.e. their isoflavones concentration, on a solvent-free basis, is greater than that in the purified solution according to a preferred embodiment.
  • Those isoflavones-enriched solids are separated from the isoflavones-depleted solution (step 60 in FIGURE 1) by methods such as centrifugation, filtration, decantation, etc. and various combinations of those according to an alternative embodiment.
  • the isoflavones-enriched solid obtained is concentrated in isoflavones.
  • the concentration of the isoflavones in the isoflavones-enriched solid is typically greater than about 30 percent (%), preferably greater than about 40 percent (%), most preferably greater than about 50 percent (%).
  • Those solids may contain at least about 30 percent (%) of the amount of the isoflavones in the starting material (i.e.
  • the isoflavones recovery yield is at least about 30 percent (%)), more preferably at least 50 percent (%), most preferably at least about 60 percent (%).
  • the isoflavones-enriched solids can be further purified, e.g. by solvent extraction, chromatographic separation, ion-exchange, adsorption on resin of low polarity, re-crystallization, etc.
  • the following is a preferred method of conducting re-crystallization for further purification of the isoflavones-enriched insolubles.
  • Water and alkali are added to the insolubles to form a solution having at least pH of about pKa minus 1.5, and a total solid concentration of between about 1 percent (%) and 40 percent (%).
  • a purified solution is formed, containing the isoflavones, and further insolubles containing at least one impurity and a minimal content of isoflavones, if any. Those insolubles are removed by methods as disclosed above.
  • the pH of the purified solution is lowered, inducing thereby precipitation of a precipitate further enriched in isoflavones. That precipitate is separated from the depleted solution, and if desired, purified again by another step of re- crystallization.
  • the pH is reduced by contact with a stream (e.g. solution or a solid) that has buffering capacity.
  • a stream e.g. solution or a solid
  • the contact is with a protein, preferably a purified one.
  • Such contact results in precipitation of isoflavones and can form an isoflavones- enriched purified protein.
  • the concentration of the solution at reduced pH (e.g. in step 50 of FIGURE 1) is about the same as that of the solution at the elevated pH (e.g. in step 30 of FIGURE 1) or smaller.
  • the temperature of the solution at the reduced pH is about the same as that of the solution at the elevated pH or higher.
  • both temperature and concentration of the solution at reduced pH are similar to those of the solution at elevated pH.
  • the malonyl glycoside and acetyl glycosides in the solution are hydrolyzed to form the glycoside form prior to the separation of the isoflavones-enriched solids, more preferably prior to the lowering of the pH.
  • the hydrolysis is preferably catalyzed chemically, enzymatically or in a combination of the two.
  • Chemical catalysis is conducted at elevated pH according to a preferred embodiment and optionally also at elevated temperature. Typically, the higher the temperature, the lower is the pH needed and vice versa. Part of the hydrolysis may take place at the elevated pH (see step 30 of FIGURE 1) according to an alternative embodiment.
  • the method of purifying a phenolic compound e.g.
  • isoflavones is suitable for the recovery of purified isoflavones from a variety of sources.
  • sources such as soy solubles are ones of high solubility, e.g. carbohydrates, which do not tend to co-precipitate with isoflavones.
  • soy solubles are ones of high solubility, e.g. carbohydrates, which do not tend to co-precipitate with isoflavones.
  • concentration is high enough to limit the isoflavones purity in the precipitate in the common industrial practice to about 4-7 percent (%).
  • a measure of the concentration of impurities that tend to co-precipitate with isoflavones is the amount of solid formed on adjusting the concentration of the source in an aqueous medium to between about 10 percent (%) and 40 percent (%) solids at pH of up to about 8. That amount (dried solids) is compared to the amount of isoflavones in the starting material and the ratio between the two is referred to in this disclosure as "R1."
  • the greater R1 the greater is the amount of impurities that tend to co- precipitate with isoflavones and lower the isoflavones purity in the precipitate.
  • R1 is greater than about 1.5, in most cases greater than about 3 and in particularly problematic cases greater than about 5.
  • R1 The greater is the need for removing impurities as insolubles, i.e. the greater should the amount of insolubles be at about pH > pKa minus 1.5.
  • R2 can reach more than about 10 percent (%), preferably more than about 30 percent (%) and most preferably more than 50 percent (%) of R1.
  • the insolubles to be removed are substantially free of isoflavones so that their removal presents no significant yield loss.
  • the starting material may contain solutes that are of commercial value.
  • soy solubles/molasses contain carbohydrates, saponins, proteins and other components. Some of those, which tend to co-precipitate with isoflavones and, in that respect are considered as impurities, could also be recovered for some applications.
  • the method of purifying a phenolic compound e.g. isoflavones
  • solutes can be recovered from the various streams of the process, e.g.
  • solutes from the starting material may also be introduced as a pre-treatment before pH adjustment to above about pKa minus 1.5 according to an alternative embodiment, j
  • proteins present in the starting material may be separated by adjusting the pH of the solution to about the protein isoelectric point (pi), by membrane filtration, or by a combination of those. In many cases, such removed proteins are enriched in the Bowman-Birk tryspin inhibitor (BBI) and present a source for its recovery.
  • BBI Bowman-Birk tryspin inhibitor
  • a preferred embodiment involves treating the starting material to remove protein at conditions such that those removed proteins are enriched in BBI.
  • BBI can be recovered from other process streams, e.g. the isoflavones-depleted solution.
  • the process may also involve separation of other solutes from the starting material or from other process streams according to alternative embodiments. For example, ashes and amino acids may be removed by means such as ion-exchange.
  • Carbohydrates may also be separated from the starting material and from other process streams according to another alternative embodiment.
  • carbohydrates may be removed by degradation to other components. Such degradation may involve enzymatic hydrolysis and/or fermentation of the carbohydrates to solutes that are easy to separate, e.g. by distillation, by extraction, by crystallization, or by known methods of solid-liquid separation. Fermentation products may be recovered according to an alternative embodiment.
  • carbohydrates may be fermented to form enzymes suitable for the isoflavones process, e.g. ones for the hydrolysis of the malonyl and acetyl forms.
  • the ratio between the weight of the precipitate formed and removed at pH 4.5 and the isoflavones content was about 10:1 ⁇ Concentration of the permeate to about 20 percent (%) total solutes without the pre-treatment at pH 4.5 would likely have resulted in R1 greater than 5.9.
  • the precipitate contained about 40 percent (%) of the initial isoflavones in the solution and the isoflavones concentration in the dried precipitate was 8.9 percent (%).
  • This comparative example shows that the amount of impurities in the permeate that tend to co-precipitate with the isoflavones is relatively high and that on concentration to about 20 percent (%) an isoflavones-containing precipitate can be formed, but the concentration of isoflavones there is relatively small.
  • Example A was concentrated to total solutes concentration of 49 percent (%).
  • the pH in the solution was 5.3. Insolubles were observed.
  • COMPARATIVE EXAMPLE C A permeate was produced according to the method of Comparative Example A.
  • the permeate was concentrated by reverse osmosis (RO) to 3 percent (%) total solids.
  • the obtained solution was further concentrated by water evaporation to total solids concentration of 110.5 percent (%).
  • the concentrated solution was cooled to ambient temperature.
  • a precipitate was formed.
  • the precipitate was separated from the concentrated solution by centrifugation, dried, weighed and analyzed for isoflavones. The weight of the dried precipitate was about 0.21 g.
  • the amount of isoflavones in the treated solution was 0.045g.
  • the ratio between the dried precipitate and the isoflavones in the starting material (R1) was 4.7. This shows that the amount of impurities that tend to co-precipitate with isoflavones is high also in permeates that did not go through the alkali treatment for hydrolysis of malonyls and acetyls.
  • EXAMPLE 1 About 440g of concentrated-treated permeate were prepared as in Comparative Example B.
  • the concentrated-treated permeate contained 0.212 percent (%) isoflavones.
  • the concentrated-treated permeate was mixed with about 110Og water and about 10Og NaOH solution of 1.5N concentration. The pH of the formed solution was 11. Mixing was then continued for 2 hours at ambient temperature and for additional 0.5 hour at 60 degrees Celsius. The temperature was lowered to the ambient one. A solution with total solids concentration of 14.3 and a precipitate were formed. The precipitate was removed and the clarified solution was analyzed. The precipitate was washed, dried, weighed and analyzed. The precipitate weighed about 4g.
  • the amount of isoflavones in the initial concentrated-treated solution was about 0.93g, so that the ratio between that dried precipitate and the isoflavones in the starting material (R2) was about 4, which is similar to R1 (see Comparative Example B).
  • Isoflavones concentrations in the clarified solution and in the washed and dried precipitate were 0.053 percent (%) and 0.03 percent (%), respectively.
  • Example 1 shows that a large fraction of the impurities that tend to co-precipitate with isoflavones can be removed, but with very little loss of yield.
  • the precipitate contained less than 1 percent (%) of the amount of isoflavones in the initial concentrated-treated solution.
  • EXAMPLE 2 About 1600g of the clarified solution obtained in Example 1 were mixed with 30 percent (%) HCI in an amount suitable to bring the pH down from 11 to 7. Mixing was applied for 2.5 hours at ambient temperature. A precipitate was formed. The precipitate was separated, washed, dried, weighed and analyzed. Its weight was about 0.6g. Isoflavones concentrations in the isoflavones-depleted solution and in the washed and dried precipitate were 0.036 percent (%) and 63 percent (%), respectively. The precipitate contained about 40 percent (%) of the amount of isoflavones in the initial concentrated-treated permeate.
  • Example 2 shows that a highly-concentrated isoflavones product is formed. Isoflavones concentration there was 63 percent (%) compared with 6.1 percent (%) in Comparative Example B.
  • EXAMPLE 3 About 150g of concentrated-treated solution were prepared as in Comparative Example B. The solution was mixed with about 200g water and about 50g NaOH solution of 1.5N. The pH of the formed solution was 11. Mixing was then continued for 7 hours at 20C. A solution with total solids concentration of 14.7 and a precipitate were formed. The precipitate was separated by centrifugation and the clarified solution was analyzed. The precipitate was washed, dried, weighed and analyzed. Its weight was about 2.4g. The amount of isoflavones in the initial concentrated-treated solution was about 0.45g, so that the ratio between that dried precipitate and the isoflavones in the starting material (R2) was about 5 (somewhat greater than R1 as found in Comparative Example B).
  • Isoflavones concentrations in the clarified solution and in the washed and dried precipitate were 0.081 percent (%) and 0.049 percent (%), respectively.
  • the precipitate contained less than 1 percent (%) of the amount of isoflavones in the initial concentrated-treated solution. I In this Example, much of the c ⁇ -precipitating impurities were removed with substantially no loss of isoflavones.
  • EXAMPLE 4 About 515g of the clarified solution obtained in Example 3 were mixed with 1.5N HCI in an amount suitable to bring the pH down from 11 to 7. Mixing was applied for 48 hours at ambient temperature. A precipitate was formed. The precipitate was separated, washed, dried, weighed and analyzed. Its weight was about 0.67g. Isoflavones concentrations in the isoflavones- depleted solution and in the washed and dried precipitate were 0.027 percent (%) and 46 percent (%), respectively.
  • EXAMPLE 5 5.5g of the wet precipitate formed in Comparative Example B (about 0.8g on dry basis) was mixed with about 30g water and about 0.5g of 1.5N NaOH solution. The pH of the formed solution was 11. Mixing was then continued for 2 hours at ambient temperature. A solution with total solids concentration of 0.9 percent (%) and a precipitate were formed. The precipitate was separated and the clarified solution was analyzed. The precipitate was washed, dried, weighed and analyzed. Its weight was about 0.14g.
  • the amount of isoflavones in the starting wet precipitate was about 0.05g, so that the ratio between that dried precipitate formed at the elevated pH and the isoflavones in the starting material (R2) was about 2.8, which is about 70 percent (%) of R1 as found in Comparative Example B.
  • Isoflavones concentrations in the clarified solution and in the washed and dried precipitate were 0.21 percent (%) and 0.47 percent (%), respectively.
  • the precipitate contained less than 1 percent (%) of the amount of isoflavones in the initial wet precipitate.
  • Example 5 The starting material in Example 5, i.e. a precipitate containing about 6.1 percent (%) isoflavones, was obtained from a permeate, rather than the permeate itself. Here too, much of the co-precipitating impurities are removed at the elevated pH with substantially no loss of isoflavones.
  • EXAMPLE 6 About 29g of the clarified solution obtained in Example 5 were mixed with 30 percent (%) HCI in an amount suitable to bring the pH down from 1 1 to 7. Mixing was applied overnight at ambient temperature. A precipitate was formed. T he precipitate was separated, washed, dried, weighed and analyzed. Its weight was about 0.098g. Isoflavones concentrations in the isoflavones-depleted solution and in the washed and dried precipitate were 0.013 percent (%) and 42 percent (%), respectively.
  • isoflavones-containing solid having a purity of 6.1 percent (%) were purified to 42 percent (%) purity.
  • EXAMPLE 7 Permeate was concentrated by RO to 3 percent (%) total-solutes as in Comparative Example C. Its isoflavones concentration was 0.02 percent (%). 283g of that solution was farther concentrated to 7.5 percent (%) total solids, cooled and 1.5N HCI solution was added to bring the pH to 4.5. A precipitate was observed. It was separated by centrifugation, washed, dried, weighed and analyzed for isoflavones. Its dry weight was about 0.22g.
  • the amount of isoflavones in the starting material was 0.057g so that the weight ratio between the precipitate and the initial isoflavones content is 3.9.
  • the precipitate contained no detectable amount of isoflavones.
  • the pH of the clear solution was brought to 10.5 by the addition of NaOH and the solution was concentrated by water evaporation to 12.4 percent (%) total solids. More NaOH was added to reach a pH of 11 and the solution was mixed for 1.5 hours at ambient temperature and for 3 additional hours at 17C. A precipitate appeared. It was separated by centrifugation, washed, dried, weighed and analyzed for isoflavones. Its dry weight was about 0.40g, i.e. the weight ratio between the precipitate and the initial isoflavones content (R2) was 7.0. The precipitate contained less than 1 percent (%)'of the initial amount of isoflavones.
  • EXAMPLE 8 About 55g of the clarified solution obtained in Example 7 were mixed with 1.5N HCI in an amount suitable to bring the pH down from 1 1 to 7. Mixing was applied overnight at 17 degrees Celsius. A precipitate was formed. The precipitate was separated, washed, dried, weighed and analyzed. Its weight was about 0.059g. Isoflavones concentrations in the isoflavones-depleted solution and in the washed and dried precipitate were 0.044 percent (%) and 27 percent (%), respectively.
  • EXAMPLE 9 Permeate was concentrated by RO to 16 percent (%) total-solutes and its isoflavones concentration was 0.08 percent (%). NaOH solution of 1.5N was added to 128g of that solution to bring the pH to 1 1 and the solution was mixed at ambient temperature for 2 hours. A precipitate appeared. It was separated by centrifugation, washed, dried, weighed and analyzed for isoflavones. Its dry weight was about 0.24g. The precipitate contained less than 1 percent (%) of the initial amount of isoflavones. EXAMPLE 10 About 130g of the clarified solution obtained in Example 9 were mixed with HCI in an amount suitable to bring the pH down from 1 1 to 7. Mixing was applied overnight at 18C. A precipitate was formed.
  • the precipitate was separated, washed, dried, weighed and analyzed. Its weight was about 0.061 g. Isoflavones concentrations in the formed clarified solution and in the washed and dried precipitate were 0.087 percent (%) and 86 percent (%), respectively. . * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * *

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Abstract

L'invention concerne un procédé permettant d'accroître le degré de pureté d'un composé phénolique dérivé d'une matière première d'origine biologique. Ce procédé consiste à prendre une matière première d'origine biologique comprenant un mélange d'au moins un composé phénolique présentant une pureté P1 et d'au moins un composé non phénolique, à former au moins une fraction de la matière première, une solution aqueuse alcaline présentant un pH correspondant au moins au pKa moins 1,5, le pKa étant celui du composé phénolique, et des matières insolubles, à séparer les matières insolubles de la solution alcaline, de manière à former une solution purifiée contenant un composé phénolique purifié présentant une pureté P2 et des matières insolubles contenant le ou les composés non phénoliques, P2 étant plus grand que P1, et les matières insolubles contenant moins de 20 pour-cent (%) environ du ou des composés phénoliques présents dans la matière première.
PCT/US2005/004160 2004-02-09 2005-02-09 Purification de composes phenoliques Ceased WO2005077930A1 (fr)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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CN117099955A (zh) * 2023-08-28 2023-11-24 江苏大学 一种可负载不同pKa多酚的酪蛋白水溶液及其制备方法

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CN117099955A (zh) * 2023-08-28 2023-11-24 江苏大学 一种可负载不同pKa多酚的酪蛋白水溶液及其制备方法

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