WO1997000309A1 - Procede de preparation enzymatique d'extraits huileux enrichis en antioxydants naturels - Google Patents

Procede de preparation enzymatique d'extraits huileux enrichis en antioxydants naturels Download PDF

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Publication number
WO1997000309A1
WO1997000309A1 PCT/ES1996/000133 ES9600133W WO9700309A1 WO 1997000309 A1 WO1997000309 A1 WO 1997000309A1 ES 9600133 W ES9600133 W ES 9600133W WO 9700309 A1 WO9700309 A1 WO 9700309A1
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Prior art keywords
tocopherol
acidity
deodorized
distillation
antioxidants
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PCT/ES1996/000133
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English (en)
Spanish (es)
Inventor
Domingo Saura Lopez
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Domingo Saura Lopez
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Publication of WO1997000309A1 publication Critical patent/WO1997000309A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/02—Oxygen as only ring hetero atoms
    • C12P17/06—Oxygen as only ring hetero atoms containing a six-membered hetero ring, e.g. fluorescein
    • 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
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
    • C07D311/72—3,4-Dihydro derivatives having in position 2 at least one methyl radical and in position 6 one oxygen atom, e.g. tocopherols
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B7/00—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
    • C11B7/0008—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of solubilities, e.g. by extraction, by separation from a solution by means of anti-solvents
    • C11B7/0025—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of solubilities, e.g. by extraction, by separation from a solution by means of anti-solvents in solvents containing oxygen in their molecule
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
    • C11C1/02—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils
    • C11C1/04—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils by hydrolysis
    • C11C1/045—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils by hydrolysis using enzymes or microorganisms, living or dead
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
    • C11C1/08—Refining
    • C11C1/10—Refining by distillation
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/02—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with glycerol
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats

Definitions

  • the present invention relates to an enzymatic type process for obtaining oily extracts enriched in natural antioxidants, especially tocopherol.
  • antioxidants used in the industry is of a huge extent. More than 150 have been collected according to their chemical structure and form of action (radical scavengers, oxygen, peroxides or acts as a UV filter.)
  • the list of those allowed in food is much shorter and is subject to recent modifications in which phenolic antioxidants are the main object of speculation.
  • Tocoles There are eight different substances with vitamin E activity in nature. They are classified into two families with the generic names of tocoles and tocotrienols. The members of each family are designated by the Greek letters: alpha, beta, gamma and delta, and depending on the position of the methyl group (-CH3) in the chroman ring. Tocoles are usually called tocopherols.
  • Alpha tocopherol has three groups in the aromatic ring, while beta and gamma tocopherol have two and tocopherol has one.
  • To the fraction D- ⁇ Tocopherol is the only one that is officially recognized as vitamin E activity as indicated by the International units (Ul).
  • D- ⁇ -tocopherol is the most potent, but its isolation from natural sources is difficult. Food and pharmaceutical preparations are based on this product
  • tocopherols are found in: cereals, oilseeds, nuts and vegetables such as beans and carrots. Also the seeds of different fruits are important sources. This content is reduced by about 30 or 40% during the refining process.
  • Tocopherols are obtained both by extraction from natural sources and by chemical synthesis.
  • the tocopherols thus obtained contain 4 fractions of natural tocopherols: ⁇ , ⁇ , ⁇ , and ⁇ -tocopherol. These molecules differ in the number of methyl groups (-CH 3 ) in the chromane ring. As regards their antioxidant activity, they differ from each other. Thus, while the order of "in vivo" activity, from highest to lowest, is ⁇ > ⁇ > ⁇ > ⁇ >, the order of "in vitro" activity is ⁇ > ⁇ > ⁇ > ⁇ >.
  • tocopherol content of the extract is richer in one or another of its fractions.
  • corn or soybean oil deodorized extracts from North America are richer in D- ⁇ -tocopherol, while sunflower extracts are more enriched in D- ⁇ -tocopherol.
  • the only isomer found in animals naturally is D- ⁇ -tocopherol.
  • Chemically synthesized vitamin E may be a mixture of the eight possible diastereoisomers of D, L- ⁇ -tocopherol, if obtained by chemical reaction of trimethylhydrophenone and natural isofitol. If synthetic isofitol is used, a mixture of two isomers is obtained, namely 2R, 4'R, 8'R and 2S, 4'R, 8'R- ⁇ -tocopherol. This distribution is of great importance in the biological activity of vitamin E.
  • the eight diastereoisomers of synthetic vitamin E are more difficult to assimilate than the natural ones.
  • the biological availability range of natural vitamin E is 36% greater than synthetic.
  • the commercial distribution of natural tocopherols is carried out for the most part with a concentration of at least 50% wealth in natural tocopherols, the rest being an added vegetable oil as an excipient.
  • Brown and Mong (USPO 3,188,120) introduced the extraction of the unsaponifiable by solvent purification, using a prior saponification with CfeCa, followed by solvent extraction and a pulverulent agent.
  • the unsaponifiable is finally distilled to extract the antioxidants by molecular distillation.
  • the present invention refers to a process for the enzymatic preparation of oily extracts enriched in natural antioxidants and, more specifically, refers to the use of lipases in obtaining an extract enriched in natural antioxidants from deodorized edible oils.
  • the process of the present invention is basically carried out using high vacuum and short step distillation combined with the heterogeneous reverse catalysis that lipases can carry out when the appropriate conditions are given which will be described in detail later in this document.
  • the esterification reactions correspond to the balances:
  • AG.- are the free fatty acids present in the deodorized.
  • TAG.- are the triglycerics of the above fatty acids.
  • fatty acids are transformed into their corresponding more volatile esters, which allows a more effective separation of acids by distillation of esters.
  • Enzymatic catalysis can also be used but in a lysis reaction, adding water to the reaction medium and degrading fatty acid esters. In this way acids are free and can be separated from tocopherols more easily than monoglycerides and diglycerides.
  • deodorized animal or vegetable oils containing antioxidants especially tocopherols are used in appreciable amounts.
  • good sources are deodorized corn, cotton, wheat germ, sesame, rosemary, palm, soy and sunflower oils.
  • Deodorized oils of rice bran and grape seeds are also susceptible to use.
  • the starting material is subjected to a de-atomization process, to eliminate a series of volatile components, some of which are described below, and which are mostly low molecular weight aldehydes, ketones and esters, together with some aromatic compounds.
  • an enzymatic treatment stage can be verified by means of a commercial lipase that can be found in the market, but using these as a synthesis catalyst.
  • This process can be performed before or after the high vacuum distillation stages.
  • the application of the principle of displacement of the chemical equilibrium to the synthesis reaction of an ester from a fatty acid and an alcohol is used, continuously eliminating the water from the medium during the reaction, which is achieved by shifting the equilibrium towards the right.
  • the elimination of water is achieved by the application of heat to a container subjected to a vacuum of between 100 and 60 mmHg.
  • the enzyme given its cost, it is preferable to use it immobilized on a support of zeolites or organic polymers of different types, being as a manageable solid with different appearance, according to the commercial house, of sand or small pearls of earthy color.
  • the enzyme is disposed inside an enzymatic reactor, inside which the enzyme is confined during the reaction.
  • the lipase to be used in the present invention is not restricted to a specific type, any of the known ones can be used. Lipase may or may not be selective or specific. Examples of selective lipases are offered by microorganisms of the genus Rihzopus. Mucor and Alcaliqenes, and the pancreatic lipase. Examples of lipases without selectivity are those produced by microorganisms of the genus Chromobacterium and Candida.
  • the process of the invention is carried out at moderate temperatures, in which the enzyme is active, and under mild conditions that avoid the need for extreme acidity or basicity conditions typical of chemical esterification processes.
  • Preferred temperatures are in the range of 20 e to 80 9 C, especially above 50 Q C, with 70 9 C being the ideal temperature.
  • reaction proceeds in the liquid phase and can be facilitated if the reagents are dissolved in an organic solvent.
  • THF tetrahydrofuran
  • DMF dimethylformamide
  • certain organic substances such as acetic acid, certain aldehydes and ketones and some esters have inhibitory effects on the activity of the enzyme. Since compounds of this nature are found in abundance in deodorized agents, it is essential to carry out the enzymatic reaction always after the dearomatization process that eliminates them almost completely.
  • the enzymatic reaction can be applied to the lysis of the fatty acid esters contained in the deodorized.
  • the water in the reaction is necessary, usually in a percentage greater than 10%, but between 0.5% and 1% of water or buffer solution of the ideal pH of the enzyme is preferable. Therefore, no excessive precautions are necessary to remove moisture that deodorized agents may contain. This moisture helps facilitate the activity of the enzyme.
  • the fatty acids are those that contain the deodorized and whose proportion will vary according to the oil from which they come; palm, soy, corn, sunflower, and others.
  • the alcohol will be incorporated into the reaction medium and a wide variety of monohydroxylates of small molecular weight such as methanol or ethanol, to polyhydroxylates such as ethylene glycol and glycerin can be used.
  • monohydroxylates small molecular weight
  • polyhydroxylates such as ethylene glycol and glycerin
  • the latter together with methanol are preferred: the first, because it leads to the synthesis of acylglycerols, natural esters without any toxic character, and the second because it leads to acyl methoxylates suitable to be obtained before the high vacuum distillation process and favor thus their separation from tocopherols by the decrease in the boiling temperature of fatty acids.
  • Esterification is also used using fractional distillation during the course of the reaction, so that the alcohol that is lost by distillation can be added to the reaction mixture at the same rate as it is lost, and always maintaining the conditions of vacuum and temperature.
  • the object of treating enzymatically before distillation is to form derivatives of the most volatile fatty acids and thus allow distillation to be more easily separated from tocopherols.
  • the enzymatic treatment after distillation consists in lowering the acidity of the product with 50% tocopherols to transform fatty acids into triglycerides and obtain a product of perfect commercial acceptance. This avoids having to force distillation conditions to reach a product of 98-100% rich in natural tocopherols, which must then be reduced to 50% wealth to be commercially distributed with a refined oil.
  • This oil added on numerous occasions has nothing to do with the original source of antioxidants, while triglycerides of enzymatic origin have a profile of fatty acid composition identical to the oil of origin.
  • Distillation is carried out in two stages. In both the heating of a thin descending film of product with high vacuum is verified. Vapors are condensed on a surface separated from the film by a clear space without obstructions. The distance between the film and the condensation surface is preferably as short as possible. When the distance is less than the average distance of the residual gaseous molecules of the species to be separated, molecular distillation is discussed.
  • Pressures less than 1 mmHg are used, it is even preferable that they are less than 0.1 mmHg, such as 0.01 or 0.001 mmHg.
  • the antioxidant is obtained in a first fraction that distills immediately after obtaining the fatty acids.
  • the temperatures at which The fatty acid fraction obtained can vary considerably depending on the conditions of pressure, distillation and the type of deodorized used.
  • the temperature is usually between 200 and 240 9 C, and especially between 230 and 240 e O It also occurs with the subsequent distillation temperature of tocopherols that is generally between 210 and 280 5 C, and especially between 270 and 280 Q O subsequently, whatever the stage, a treatment with an organic solvent of the fraction enriched in antioxidant and enzymatically treated is verified.
  • the solvents may be aromatic hydrocarbons, alkanes such as hexane and preferably alcohols, especially ethanol and methanol.
  • an extract having a normalized tocopherol richness at 50% concentration is obtained.
  • most manufacturers force operating conditions to reach higher concentrations and then normalize to 50% wealth by adding vegetable oils.
  • a typical extract obtained by the process of the present invention has the following composition:
  • tocopherols are common in vegetable oils. Some, such as mono and diglycerides, are specific adjuvants of tocopherol in its antioxidant function, by facilitating its dispersion in fat or its absorption through the stomach.
  • Figure 1 Shows a gas chromatogram of a deodorized mixture of soybean and sunflower oils (1: indicates ⁇ -tocopherol; 2: indicates ⁇ + ⁇ -tocopherol; and 3: indicates ⁇ -tocopherol; AG indicates the position of fatty acids).
  • Figure 2. Shows a gas chromatogram of the distilled tocopherol, after having subjected it to the two distillation processes of Example 1.
  • Figure 3. Shows a gas chromatogram of the final product obtained after the enzymatic treatment, where the effect is shown that this treatment has on fatty acids, which are practically no longer detected.
  • Figure 4.- It is a graphic representation that shows the evolution of acidity in the process of Example 4. In ordinates the% of acidity is represented and in abscissa the time in hours.
  • Figure 5. It is a graphic representation that shows the evolution of acidity in the process of Example 5. In ordinates the% of acidity is represented and in abscissa the time in hours.
  • Example 1 The present invention is further illustrated by the following Examples, which are not intended to be limiting in scope.
  • Example 1 The present invention is further illustrated by the following Examples, which are not intended to be limiting in scope.
  • a deodorized mixture of soybean and sunflower oils was used as the starting product, with an acidity of 28% refractive index of 1, 48040 and a tocopherol content of 5.06%. He underwent a dearomatization process at 150 s C and moderate vacuum. The residue that remained had 13.5% acidity, a refractive index at 20 9 C of 1,48740, the tocopherol content being 7.57% distributed as follows: 1, 16% ⁇ -tocopherol, 2 , 55% ⁇ + ⁇ -tocopherol and 3.85% ⁇ -tocopherol.
  • a vapor phase where no tocopherol is detected with an acidity of 85% and a squalene content of 4.76%, of stigmasterol (as an example of sterols) of 1.1%.
  • the refractive index in this phase was 1,47040 to 20 9 C.
  • the residual phase that did not distilled had the following characteristics, 12.4% acidity, 26.0% of tocopherols distributed as follows: 2, 74% of ⁇ -tocopherol, 5.94% of ⁇ + ⁇ -tocopherol and 17.34% of ⁇ -tocopherol.
  • Figure 1 shows a gas chromatogram of a deodorized mixture of soybean and sunflower oils (1 indicates ⁇ -tocopherol, 2 indicates - ⁇ + ⁇ -tocopherol and 3 indicates ⁇ -tocopherol, AG indicates position of fatty acids) where the large proportion of fatty acids is appreciated.
  • Example 2 A sample of soy deodorized with an acidity of 48.5% and a tocopherol content of 7-8% was used as the starting product. As in Example 1, it was subjected to a de-atomization process that eliminated volatiles at 250 9 C and low pressure. Subsequently, the antioxidant was subjected to a distillation process that generated a residue with 1.3% acidity and 11-15% tocopherol and a distillate with 69.1% acidity and between 5-7% tocopherol .
  • the amount of sample obtained from an amount of 640 Kg raw material of sunflower oil deodorized with an acidity of 31% and a tocopherol content of 7.45% that were subjected to deodorization at a temperature is quantified of 150 9 C and vacuum, obtaining 30 Kg of deodorized with an acidity of 27.1% and a tocopherol content of 1.45%.
  • the first distillation at 230-240 5 C 350 kg of residue remained with 15.6% acidity and 5.76% total tocopherols, and distilled 120 kg of fatty acids with 89.2% acidity and a 1.5% tocopherols.
  • This example is intended to illustrate the use of lipase for esterification of deodorized with an alcohol, in this case glycerin.
  • the formation of triglycerides that cannot accompany tocopherol in distillation is intended.
  • the evolution of acidity with the reaction time at 70 9 C and 70 mmHg is shown in Figure 4.

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Abstract

Le procédé consiste (a) à soumettre à une réaction enzymatique un déodorat d'huiles animales ou végétales ayant été soumis au préalable à une distillation sous vide; (b) à soumettre le produit obtenu à une distillation en deux étapes, la première à 200-240 °C et la seconde à 210-280 °C; (c) à traiter la fraction de distillation riche en antioxydants puis à effectuer une filtration, une centrifugation et une distillation. Application à l'industrie alimentaire pour l'homme et les animaux.
PCT/ES1996/000133 1995-06-15 1996-06-14 Procede de preparation enzymatique d'extraits huileux enrichis en antioxydants naturels WO1997000309A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ES9501209A ES2093570B1 (es) 1995-06-15 1995-06-15 Procedimiento para la preparacion enzimatica de extractos oleosos enriquecidos en antioxidantes naturales.
ESP9501209 1995-06-15

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WO1997000309A1 true WO1997000309A1 (fr) 1997-01-03

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002000640A1 (fr) * 2000-06-28 2002-01-03 Vitae - Caps, S.A. Procede d'extraction et de purification de tocopherols naturels et de sterols par esterification avec du trimethylol propane
WO2002050221A1 (fr) * 2000-12-21 2002-06-27 Aarhus Oliefabrik A/S Procede pour la preparation de fractions d'huile vegetale riches en matiere insaponifiable, non tocolique et a point de fusion eleve
CN112194647A (zh) * 2020-09-28 2021-01-08 福建福迩金生物科技有限公司 一种天然维生素e的制备方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2691974A1 (fr) * 1992-06-05 1993-12-10 Sarpap Procédé de séparation de la fraction insaponifiable libre ou estérifiée d'une huile, d'un corps gras ou d'un extrait lipidique d'origine végétale, produit isolé ainsi obtenu et compositions le contenant.
US5424457A (en) * 1994-05-27 1995-06-13 Eastman Chemical Company Process for the production of sterol and tocopherol concentrates

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2691974A1 (fr) * 1992-06-05 1993-12-10 Sarpap Procédé de séparation de la fraction insaponifiable libre ou estérifiée d'une huile, d'un corps gras ou d'un extrait lipidique d'origine végétale, produit isolé ainsi obtenu et compositions le contenant.
US5424457A (en) * 1994-05-27 1995-06-13 Eastman Chemical Company Process for the production of sterol and tocopherol concentrates

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
S. RAMAMURTHI: "ENZYMATIC PRETREATMENT OF DEODORIZER DISTILLATE FOR CONCENTRATION OF STEROLS AND TOCOPHEROLS", JOURNAL OF AMERICAN OIL CHEMIST SOCIETY, vol. 70, no. 3, March 1993 (1993-03-01), ILLINOIS (USA), pages 287 - 295, XP002013835 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002000640A1 (fr) * 2000-06-28 2002-01-03 Vitae - Caps, S.A. Procede d'extraction et de purification de tocopherols naturels et de sterols par esterification avec du trimethylol propane
ES2177401A1 (es) * 2000-06-28 2002-12-01 Vitae Caps S A Procedimiento de extraccion y purificacion de tocoferoles naturales y esteroles por esterificacion con trimetilol propano.
WO2002050221A1 (fr) * 2000-12-21 2002-06-27 Aarhus Oliefabrik A/S Procede pour la preparation de fractions d'huile vegetale riches en matiere insaponifiable, non tocolique et a point de fusion eleve
CN112194647A (zh) * 2020-09-28 2021-01-08 福建福迩金生物科技有限公司 一种天然维生素e的制备方法

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ES2093570A1 (es) 1996-12-16

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