WO1994008028A1 - Procede de preparation, par voie enzymatique, d'aromes, notamment des ionones et des aldehydes en c6 a c¿10? - Google Patents
Procede de preparation, par voie enzymatique, d'aromes, notamment des ionones et des aldehydes en c6 a c¿10? Download PDFInfo
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- WO1994008028A1 WO1994008028A1 PCT/FR1993/000943 FR9300943W WO9408028A1 WO 1994008028 A1 WO1994008028 A1 WO 1994008028A1 FR 9300943 W FR9300943 W FR 9300943W WO 9408028 A1 WO9408028 A1 WO 9408028A1
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- 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
- C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
- C12P7/04—Preparation of oxygen-containing organic compounds containing a hydroxy group acyclic
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- 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
- C12P7/24—Preparation of oxygen-containing organic compounds containing a carbonyl group
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- 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
- C12P7/24—Preparation of oxygen-containing organic compounds containing a carbonyl group
- C12P7/26—Ketones
Definitions
- the present invention relates to a novel process for the enzymatic preparation of flavors, in particular ionones and C 6 to C 10 aldehydes. It relates more particularly to a process for the preparation of optically active ⁇ -ionone, of ⁇ -ionone, of C 6 aldehydes such as n-hexanal, trans-2-hexenal, of C 10 aldehydes such as trans-2, cis-4-decadienal and trans-2, trans-4-decadienal.
- flavoring additives poses complex problems, because in most foodstuffs, the natural flavor, which we seek to find through flavorings, is the result of the mixture of multiple chemical components that it is most often difficult to determine with accuracy.
- ionones and more particularly ⁇ -ionone and 3-ionone are found in the aroma of many fruits such as raspberry, blackberry, blackcurrant, peach, apricot, melon, tomato in the aroma of plants such as violet, Boronia meqastiqma, in the aroma of processed plants such as black tea, tobacco, carrot, vanilla or in mushrooms such as chanterelle.
- FISCHER and GROSCH Z. Lebenson.Schs.-Forsch, 165, 137-139, 1977 obtained various aldehydes such as hexanal, 2-4 decadienal (two diastereoisomers), trans-2 hexenal and trans-2-octenal, by presenting the lipoxygenase L 2 from soybeans and linoleic acid.
- US Patent No. 4,769,24 describes a process for preparing green notes, such as n-hexanal, l-pentene-3-ol, l trans-2-hexanal and cis-2- pentenol (ex. 1 and 2, column 5) using a mixture consisting of ground soybeans, unsaturated fatty acids, in the presence of water (in the proportion of 3 to 20 times the weight of the soybeans) and an addition of lipase.
- the reaction temperature is between 5 and 60 ° C (preferably 25 and 50 ° C).
- the mixture is kept under stirring for a period which can range from 5 minutes to 24 hours (preferably 3 minutes to 10 hours), while adding air or oxygen during the reaction.
- the present inventors have developed a process which makes it possible to obtain aromas of high concentration.
- a source or preparation of lipoxygenase and hydroperoxide-lyase is brought into contact, a natural source of unsaturated fatty acids and optionally a natural source of carotene, with a view to biogenerating natural aldehydes, and where appropriate, ionones.
- the enzymatic reaction takes place in a "viscous" medium with high viscosity, which makes it possible to limit the transfer of the products into the medium and consequently, to minimize the inhibitory effect that the product exerts on the reaction.
- the enzymatic oxidation of the invention takes place in a medium whose water content is relatively low, therefore concentrated in bioreactive components.
- any factor that increases enzyme-substrate contact will accelerate the development of enzyme reactions.
- the gas transfer is ensured by agitation of the medium. We will therefore favor the enzymatic reactions by ensuring an intensified kneading of the various components.
- the yield of flavoring substances obtained according to the process of the invention is considerably higher than those obtained according to the prior techniques.
- the pasty medium of the process of the invention is a reaction medium with several phases comprising in particular a solid phase, one or more liquid phases and one or more gas phases, the solid phase and the liquid phase (s) being present in weight proportions of 100: 300 (solid: liquid) approximately.
- the solid phase can consist of a mixture of different solids, for example different flours, different plants or a mixture of flours and plants.
- the liquid phases include at least one oily phase. When there is a plurality of liquid phases, they are immiscible liquids.
- the invention consists of a process for the enzymatic preparation of aromas, in particular of C 6 to C 10 aldehydes, by contacting at least one source of lipoxygenase and hydroperoxide-lyase , with a source of polyunsaturated fatty acids, the reaction being carried out with stirring, in the presence of oxygen, in a medium with several phases comprising at least one solid phase and an oily phase characterized in that said medium comprises, for 100 parts of solid phase, approximately 3 to 150 parts of an oily phase, and possibly 0 to 250 parts approximately of an aqueous phase.
- the medium is either a three-phase medium: solid phase, oily phase and gas phase, or a four-phase medium: solid phase, oily phase, aqueous phase and gas phase.
- These different phases are fully or partially functional, that is to say that they can consist of reagents involved in the enzymatic reaction, but can also include texturing agents, contributing to the "pasty" texture of the medium. .
- the sources of lipoxygenase, hydroperoxide lyase, polyunsaturated fatty acids and, where appropriate, carotene, as well as the texture agents, are chosen so that the reaction medium comprises all the phases mentioned above. , in appropriate proportions, to obtain the dough.
- the source of lipoxygenase and hydroperoxide lyase can constitute the solid phase or part of this phase, and the source of polyunsaturated fatty acids can constitute the oily phase.
- the presence of the solid phase is essential for obtaining a "pasty" medium.
- the concentrations of the reagents are: i) solid phase lipoxygenase activity: up to 1.5 mmol / min / g;
- - polyunsaturated fatty acids up to 78% linoleic acid, up to 60% linolenic acid;
- the medium is advantageously a four-phase medium, comprising for 100 parts of solid phase, 3 to 120 parts of oily phase (for example 4 to 50) and 20 to 250 parts of aqueous phase (for example 50 to 200), the phase oily and the aqueous phase together representing less than 300 parts, and more particularly less than 250 parts.
- the medium contains an aqueous source of carotene, it comprises per 100 parts of solid phase, 10 to 40 parts of oily phase and 80 to 200 parts of aqueous phase.
- the medium does not contain an aqueous source of carotene, it preferably comprises per 100 parts of solid phase, 3 to 100 parts of oily phase and up to 100 parts of aqueous phase.
- the aldehydes obtained according to this process result from the oxidative degradation of polyunsaturated fatty acids. These flavor compounds differ depending on the nature of the unsaturated fatty acids used.
- the ionones obtained are a- and 3-ionones and expoxy-ionones, and are produced by the co-oxidation of carotenoids by peroxyl radicals, released during the oxidation reaction of unsaturated fatty acids.
- the ⁇ -ionone obtained by the process is essentially R (+) trans- ⁇ -ionone.
- this enantiomer accounts for more than 90% in the natural aromas of raspberry, violet, Boronia meqastiqma, black tea, carrot or even vanilla.
- the method comprises contacting a source or a preparation of lipoxygenase and hydroperoxide-lyase, a natural source of polyunsaturated fatty acids and a natural source of carotene, the reaction being carried out in a mixer, in a concentrated medium with high viscosity, the oxygen supply of the reaction mixture being carried out during the mixing by a supply of air or oxygen or a mixture air / oxygen.
- the pressure prevailing in the reaction medium is at least equal to atmospheric pressure.
- the sources can be the following:
- oilseeds such as soybeans, rapeseed, sunflower
- protein crops such as peas, field beans, lupins
- cereals such as wheat, corn, barley, oats, rice, rye, buckwheat, sorghum and triticale
- tubers such as potato or cassava.
- Cereals can be used in the form of whole grains, grain fraction (resulting for example from an enzymatic, chemical, thermal or mechanical treatment of the grain), or any other product resulting from the grinding of the grain such as flour or semolina, provided that their enzymatic activity is preserved.
- the sources of lipoxygenases can be enzymatically active soybean flour, soybeans, sprouted or not.
- the germinated or non-germinated soybeans should preferably be ground using a grinder or a homogenizer, without thermal inactivation of the enzymes present.
- the enzymatic activity of these preparations can be verified by applying the methods described by GROSCH et al. (supra).
- soy flour, wheat flour or ground corn kernels will be used as a source of lipoxygenase and hydroperoxide-lyase.
- enzymes When enzymes are used in this form, they constitute the solid phase.
- the source of hydroperoxide lyase is normally the same as the source of lipoxygenases. This enzyme catalyzes the cleavage of hydroperoxides formed during the fatty acid oxidation reaction, thereby ensuring the production of aldehydes.
- the unsaturated fatty acids used in the process preferably have between 8 and 20 carbon atoms, and are advantageously polyunsaturated.
- fatty acids such as oleic acid, linoleic acid, ⁇ -linolenic acid, acid will be used. eicosapentaenoic, arachidonic acid and ricinoleic acid. It is also possible to use fats or oils of vegetable, animal or microbial origin, containing these fatty acids, and which will be subjected to a lipolysis reaction preferably by the enzymatic route using one or more lipases.
- fats or oils of vegetable origin can be, for example, soybean, sunflower, safflower, olive, grape seed, corn germ, wheat germ, peanut, sesame oils , nuts, flax, cotton seeds, borage, evening primrose, cynara, as well as cocoa butter.
- These fats can also be of animal origin such as butter, bacon, cod oils, sardines and various other fish or mammals.
- the hydrolysis will be carried out using one or more lipases or a preparation of lipases, originating from micro-organisms, plants or animals.
- the lipase preparation can be purified or not. Any lipase capable of carrying out the reaction on the chosen fat or oil can be used. It can be a purified preparation containing a single enzyme or, alternatively, a mixture of several enzymes exhibiting lipase activity.
- the enzyme having lipase activity can be immobilized on a solid support. This reaction can be carried out prior to the lipoxygenase reaction or concomitantly.
- the amount of lipase (s) added will generally vary from a few tens to a few hundred units per gram of oil or fat.
- the source of polyunsaturated fatty acids can be added before, during or after the grinding or mixing of the other raw materials, continuously or discontinuously.
- the medium contains a source of carotene
- natural carotene will be used, originating from higher plants, algae or micro ⁇ organisms. These are ⁇ and ⁇ -carotenes.
- the best sources are carrot, palm oil and certain algae.
- Carotene can be in the form of oleoresin, in which case it will be part of the oily phase. It can also be used in the form of an aqueous solution or also in the form of a suspension, for example a concentrated carrot juice containing for example 20% of suspended solids.
- aqueous phase preferably corresponding to a value comprised between 1/3 and 2 times the mass of flour or soya beans.
- the aqueous phase can be added before, during or after grinding or mixing of the other raw materials, discontinuously or continuously.
- the medium can also contain texturing agents, for example glycerin, as well as other additives such as emulsifying agents; agents for optimizing the enzymatic activity, for example calcium chloride, ferrous sulfate and ascorbic acid. It is important to include the proportions of these additives in the calculation of the shares of each phase.
- the reaction is carried out in a concentrated medium, at high viscosity, with stirring, in the presence of air and / or oxygen, under pressure.
- the oxygen is present in the form of a gas comprising at least 21% of oxygen, for example air, air enriched with oxygen or pure oxygen.
- This gas comprising at least 21% oxygen constitutes the gas phase of the reaction medium.
- Its incorporation into the medium is preferably such that the final apparent density, that is to say at the end of the reaction, is between 0.9 to 0.4 kg.L “1 , for example 0.5kg.L “ 1 , and is a function of the following three parameters: the flow of oxygen or air, the pressure under which the reaction is carried out and agitation.
- "Bulk density" means the density of the medium comprising the incorporated gas phase.
- the maximum flow of air and / or oxygen injected during the bioreaction can reach 15 times the volume of the bioreactive mixture per minute, for example 2 or 4 times. If the flow rate is too high, this will result in high loss of aromas by entrainment. 0 to 15 liters / min per liter of medium will be injected, for example from 1 to 2 1 / min of air and / or oxygen for 2 liters of pasty mixture.
- the air and / or oxygen pressure within the reactor is between atmospheric pressure and 50 bar (about 50 x 10 5 Pa), for example between 8 bar (about 8 x 10 5 Pa ) and 25 bar (approximately 25 x 10 5 Pa).
- the agitation of the medium is carried out by any suitable means, preferably by a planetary type agitator, used at a speed of rotation of between 20 to 200 rpm, for example 60 to 150 rpm "1 .
- the temperature will generally be between 10 and 60 ° C. preferably between 20 and 40 ° C.
- the viscosity of the pasty medium it can be characterized using two types of measurement, namely: a) the compressive force, the value of which was understood during the tests carried out between 3N (for a mixture with 55% water) and 5N (for a mixture with 45% water); b) the adhesion force, the value of which was understood during the tests carried out between 5N and 8N.
- the reaction time will generally be between 5 and 48 hours, preferably between 10 and 24 hours.
- the reaction is normally carried out at a pH between 4.5 and 10, more generally between 5 and 7.
- the volatile fraction containing the aromas will be extracted by any suitable means, such as accelerated hydro ⁇ distillation, for example in a turbo-extractor, or by steam entrainment or even by means of supercritical CO 2 .
- the yields of ionones and aldehydes are, according to the invention, exploitable on an industrial scale.
- the concentration of ⁇ - and 3-ionones can reach between 100 and 400 mg.kg " 1 medium.
- the concentration of aldehydes can reach 100 mg.kg " 1 medium.
- the process of the invention is preferably applied for the production of optically active ⁇ -ionones, 9-ionones, n-hexanal, trans-2- hexenal, trans-2, cis-4 -decadienal, trans-2, trans-4-decadienal, epoxy-5,6-, 9-ionone and dihydroactinidiolide.
- the invention also relates to a process for the production, by enzymatic route, of alcohol, in particular of C 6 to C 10 alcohols, characterized in that it comprises: i) the preparation, according to the process of the invention described below above, C 6 to C 10 aldehydes; ii) bringing the aldehydes obtained according to i) into contact with one or more alcohol dehydrogenases; iii) recovery of the alcohols thus obtained.
- one or more alcohol dehydrogenases are used. This stage of the procedure can be carried out concomitantly with the oxidation reaction, or successively.
- the production of cis-3-hexenol and hexanol is particularly preferred.
- This reactor is composed of a sealed enclosure or tank 1, the upper part of which is closed off by a fixed cover 2 in which a movable plate 2a can rotate a support of a rotating main axis 3. Rotating joints 4 allowing the rotation of said plate 2a, while leaving the tank 1 stationary and ensuring the seal.
- the fixed cover 2 is assembled to the tank 1 in a leaktight manner, by means of a circular fixed joint 5.
- This rotating tool can be either a loop , either a blade, a pallet or any mesh, metal or other chemically inert substance.
- the gaseous medium is injected into the reactor enclosure at the level of a supply conduit 10a, while a permanent leak from the same gaseous medium is provided via a conduit 10b ensuring a controlled leak so as to ensure the renewal of the gaseous fluid permanently, on the basis of 2 times the volume of the fluid per minute, while maintaining the pressure in the enclosure at the desired value for the bioreaction.
- compositions which use the reactor described above, illustrate some characteristic compositions of mixtures, implementing the process according to the present invention, with a view to the enzymatic production of C 6 -C 10 ionones and aldehydes.
- the compositions are defined as a percentage by weight calculated on the basis of the total mass of the various components.
- the bioreactive mixture was prepared in a mixer-kneader, of the type of the reactor described above, with an internal volume of 6 liters, with stirring.
- soybean flour raw full fat enzymatic
- carrot oleoresin in the proportion of 4.41%
- safflower oil in the proportion of 9.30%
- water in the proportion of 48.96%.
- a pasty medium was obtained, which was kneaded at a rate of 90 rpm at 25 ° C.
- the oxygen supply to the mixture was ensured by a continuous flow of pure oxygen at the rate of 0.5 L.min-1, under atmospheric pressure.
- the apparent density of the medium is between 0.7 and 0.8 kg.l "1 .
- the flavor substances synthesized were extracted by steam entrainment, under atmospheric pressure, for different durations of bioproduction.
- the volatile fraction is analyzed by gas chromatography and optionally by mass spectrometry.
- the best ionone concentrations obtained after a test period of 26 hours, are 95 mg.kg- ⁇ of paste for the ⁇ -ionone and 300mg.kg- ⁇ of paste for the / 0-ionone.
- the epoxy-5,6-? -Ionone concentration is 575 mg.kg- ⁇ of paste and the dihydroactinidiolide concentration is I30mg.kg-1 of paste.
- the ⁇ -ionone produced is optically active.
- the enantiomer obtained is very predominantly R (+) trans- ⁇ -ionone.
- Example 1 The protocol described in Example 1 was repeated, except that the flow of oxygen supplied to the bioreactive mixture is double (1 L.min-1).
- the duration of the bioreaction was another 26 hours and it was found that the concentrations of epoxy-5,6-3-ionone and dihydroactinidiolide were in increasing throughout the duration of the test and reached respectively at the 26th hour the values of 100 g.kg "1 of dough and 300 mg.kg " 1 of dough.
- concentrations of ⁇ - and ⁇ -ionones they reached their maximum values at the 20th hour and remained stable until the end of the duration of the bioreaction. At the 26th hour, the concentrations of ⁇ - and ⁇ -ionones were 230mg.kg 1 of paste and lOOmg.kg "1 of paste respectively.
- the bioreactive mixture was prepared in a mixer-kneader of the type of the reactor described above, with an internal volume of 6 liters, with stirring.
- the mixture consists of carrot juice (20% suspended solids) in the proportion of 65.87%, soy flour in the proportion of 25.80% and safflower oil in the proportion of 6.81%.
- lipase An addition of 595 KU of lipase was carried out, as well as an addition of calcium chloride (at a rate of 0.86%), ferrous sulfate (at a rate of 0.07%) and ascorbic acid ( about 0.01%).
- a pasty medium was obtained, which was worked under the same conditions as in Example 2 (continuous flow of pure oxygen, at a rate of 1 L.min ⁇ 1 , under atmospheric pressure).
- the concentrations of ⁇ - and ⁇ -ionones respectively reached the values of 210 mg.kg “1 of paste and I85mg.kg” 1 of paste.
- the epoxy-5,6-) 0-ionone and dihydroactinidiolide concentrations they respectively reached the values of 140 mg.kg “1 of paste and 20mg.kg " 1 of paste after 12 hours of bioreaction.
- Example 4 The protocol described in Example 4 was repeated, except that the intakes of iron sulphate and ascorbic acid were omitted.
- the duration of the bioreaction was 28 hours and it was found that the concentrations of ⁇ - and ⁇ -ionones reached respectively after 16 hours of bioreaction the values of 255mg.kg "1 of paste and of ⁇ Omg.kg " 1 of dough.
- n-hexanal and 2,4-decadienal concentrations of I55mg.kg "1 of dough and 200mg.kg " 1 of dough were obtained at the 16th hour. Measurements made at the 21st hour of bioreaction gave the respective values of 220mg.kg “1 of dough and 2l0mg.kg " 1 of dough.
- Example 5 The protocol described in Example 5 was repeated, except that it was passed through the mixture bioreactive a double flow of oxygen (2 L. in "1 , under atmospheric pressure).
- the duration of the bioreaction was still 28 hours and 1 • it was found that the concentrations of ⁇ - and ⁇ -ionones reached respectively after 16 hours of bioreaction the values of l ⁇ Omg.kg "1 of dough and I30mg.kg "1 of dough. Measurements carried out at the 28th hour of bioreaction gave the respective values of 270mg.kg “1 of dough and 175mg.kg " 1 of dough, that is to say values in increase of about 50%.
- the bioreactive mixture was prepared in a mixer-kneader of the type of the reactor described above, with an internal volume of 6 liters, with stirring.
- the mixture consists of concentrated carrot juice (20% suspended solids) in the proportion of 77.67%, soy flour in the proportion of 16.05% and safflower oil in the proportion of 5.18%.
- the bioreactive mixture obtained was worked under the same conditions as in Example 2 (oxygen flow rate: 1 L. in "1 , under atmospheric pressure).
- the duration of the bioreaction was 35 hours and 1 * it was found that the concentrations of ⁇ - and ⁇ -ionones were respectively only 78mg.kg ' 1 of dough and 70mg.kg ' 1 of dough the 35th hour. In addition, they were only very slightly growing during the course of the reaction until the 35th hour.
- the concentration of 5,6 -? - ionone epoxy was 70 mg.kg " 1 of paste after 35 hours of bioreaction. At the same time, the concentration of dihydroactinidiolide reached the value of ⁇ Omg.kg " 1 of dough.
- the bioreactive mixture was prepared in a mixer-kneader of the type of the reactor described above, with an internal volume of 80 liters, with stirring.
- This mixture consists of concentrated carrot juice (20% suspended solids) in the proportion of 55.50%, soy flour in the proportion of 37.50% and safflower oil in the proportion of 5.72%.
- a pasty medium was obtained, which was kneaded at the rate of 70 rpm "1 , at 26 ° * 1 ° C.
- the oxygen supply to the mixture was ensured by a continuous flow of air at the rate of 10 L.min "1 approximately.
- the atmosphere which surmounted the bioreactive medium was under a pressure of 2 bars.
- the duration of the bioreaction was 40 hours and 1 • it was found that the concentration of ⁇ -ionone produced was 230mg.kg "1 of paste at the 40th hour, when it was only 110 mg. kg "1 of dough after 24 hours of bioreaction.
- the bioreactive mixture was prepared in a mixer-kneader of the type of the reactor described above, with an internal volume of 6 liters, with stirring.
- This mixture consists of soy flour in the proportion of 47.30%, safflower oil in the proportion of 1.97% and water in the proportion of 49.27%. An emulsion of the components was thus produced in the aqueous phase.
- a pasty medium was obtained, which was kneaded at a rate of 110 t. in "1 , at 26 ° ⁇ 1 ° C.
- the oxygen supply to the mixture was ensured by a continuous flow of air at the rate of 1.66 L.min " 1 , under atmospheric pressure.
- the synthesized flavor substances were extracted by steam entrainment, at atmospheric pressure, for different durations of bioreaction.
- the duration of the bioreaction was 23 hours and it was found that the concentrations of n-hexanal and 2,4-decadienal, the main flavor compounds obtained in the present trial reached respectively after 23 hours of bioreaction the values of 1.71g.kg * 1 of dough and 0.70g.kg " 1 of dough.
- Example 9 The protocol described in Example 9 was repeated, except that the quantity of safflower oil was increased, the concentration of which was increased to the detriment of that of soy flour (45.33%), (100 parts of solid phase, 8.76 parts of oily phase and 108.4 parts of aqueous phase).
- a pasty medium was obtained, which was kneaded at the rate of 100 rpm "1 , at 25 ° ⁇ 1 ° C.
- the duration of the bioreaction was 23 hours and it was found that the concentrations in n -hexanal and 2,4-decadienal reached respectively at the 23rd hour the values of 3.40g. g "1 of dough and 0.86g.kg " 1 of dough.
- the bioreactive mixture was prepared in a mixer-kneader of the type of the reactor described above, with an internal volume of 80 liters, with stirring.
- lipase 14,600 KU was added, as well as calcium chloride (0.73%), ferrous sulfate (0.07%) and ascorbic acid (about 0.01%).
- a pasty medium was obtained, which was kneaded at the rate of 70 rpm "1 , at 32 ° ⁇ 1 C.
- the oxygen supply to the mixture was ensured by a continuous flow of air at the rate of 10 L .min ' about 1.
- the atmosphere which surmounted the bioreactive medium was under a pressure of 2 bars.
- the duration of the bioreaction was 17 hours.
- the two main flavoring substances present in the volatile fraction have been found to be n-hexanal and 2,4-decadienal. They respectively reached the concentrations of 2.99g.kg "1 of paste and 0.40g.kg " 1 of paste at the 17th hour of bioreaction.
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Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP93920938A EP0662141A1 (fr) | 1992-09-28 | 1993-09-27 | Procede de preparation, par voie enzymatique, d'aromes, notamment des ionones et des aldehydes en c 6? a c 10? |
JP6500902A JPH08504084A (ja) | 1992-09-28 | 1993-09-27 | 芳香物質、特にイオノン及びc▲下6▼〜c▲下1▼▲下0▼のアルデヒドの、酵素による調製方法 |
US08/406,959 US5705372A (en) | 1992-09-28 | 1993-09-27 | Enzymatic process for the preparation of flavours, in particular the ionones and C6 to C10 aldehydes |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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FR9211513A FR2696192B1 (fr) | 1992-09-28 | 1992-09-28 | Procédé de préparation par voie enzymatique d'ionones et d'aldéhydes volatils. |
FR92/11513 | 1992-09-28 |
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WO1994008028A1 true WO1994008028A1 (fr) | 1994-04-14 |
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PCT/FR1993/000943 WO1994008028A1 (fr) | 1992-09-28 | 1993-09-27 | Procede de preparation, par voie enzymatique, d'aromes, notamment des ionones et des aldehydes en c6 a c¿10? |
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US (1) | US5705372A (fr) |
EP (1) | EP0662141A1 (fr) |
JP (1) | JPH08504084A (fr) |
CA (1) | CA2145526A1 (fr) |
FR (1) | FR2696192B1 (fr) |
WO (1) | WO1994008028A1 (fr) |
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EP0911414A1 (fr) * | 1997-10-23 | 1999-04-28 | Givaudan-Roure (International) Sa | Procédé pour la préparation des produits de la dégradation d'acides gras |
US6150145A (en) * | 1997-10-23 | 2000-11-21 | Givaudan Roure (International) Sa | Process for the production of degradation products of fatty acids |
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ES2197573T3 (es) | 1998-09-02 | 2004-01-01 | Unilever N.V. | Productos de tomate enriquecidos en beta-ciclocitral. |
EP0983725B1 (fr) * | 1998-09-02 | 2003-05-02 | Unilever N.V. | Produits à base de tomates enrichis en beta-cyclocitral |
CA2392118A1 (fr) * | 1999-12-02 | 2001-06-07 | Quest International B.V. | Procede de preparation enzymatique d'aromes enrichies en c6-c10 aldehydes |
US6787684B2 (en) * | 2000-10-16 | 2004-09-07 | E. & J. Gallo Winery | Lipoxygenase genes from Vitis vinifera |
DE10206504A1 (de) * | 2002-02-16 | 2003-08-28 | Cognis Deutschland Gmbh | Verfahren zur Gewinnung von Hydroperoxiden |
DE112006002419T5 (de) * | 2005-09-13 | 2008-07-17 | Takasago International Corp. | Verfahren zur Herstellung von optisch aktivem α-Ionen |
WO2017033674A1 (fr) * | 2015-08-24 | 2017-03-02 | 株式会社J-オイルミルズ | Procédé de production d'huile de soja, procédé de production d'huile mixte, et procédé d'inhibition de l'odeur de l'huile de soja dans les endroits lumineux |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4769243A (en) * | 1985-12-03 | 1988-09-06 | Takasago Perfumery Co., Ltd. | Method for preparing green aroma compounds |
EP0443926A1 (fr) * | 1990-02-22 | 1991-08-28 | Elf Aquitaine | Procédé d'obtention d'irone par voie enzymatique |
EP0481147A1 (fr) * | 1989-10-03 | 1992-04-22 | Pernod-Ricard | Procédé de synthèse du cis-3-hexene-1-ol à partir d'acide gras insaturé |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US100790A (en) * | 1870-03-15 | Improvement in buckwheat-hulling machines | ||
DE69320302T2 (de) * | 1992-05-26 | 1999-01-28 | Firmenich & Cie | Enzymatisches Verfahren zur Herstellung von n-Hexanal, 3-(Z)-Hexen-1-al, 2-(E)-hexen-1-al, oder entsprechenden Alkoholen mittels einer Soja-Lipoxygenase und einer Guave-Lyase |
-
1992
- 1992-09-28 FR FR9211513A patent/FR2696192B1/fr not_active Expired - Lifetime
-
1993
- 1993-09-27 EP EP93920938A patent/EP0662141A1/fr not_active Withdrawn
- 1993-09-27 JP JP6500902A patent/JPH08504084A/ja active Pending
- 1993-09-27 CA CA002145526A patent/CA2145526A1/fr not_active Abandoned
- 1993-09-27 WO PCT/FR1993/000943 patent/WO1994008028A1/fr not_active Application Discontinuation
- 1993-09-27 US US08/406,959 patent/US5705372A/en not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4769243A (en) * | 1985-12-03 | 1988-09-06 | Takasago Perfumery Co., Ltd. | Method for preparing green aroma compounds |
EP0481147A1 (fr) * | 1989-10-03 | 1992-04-22 | Pernod-Ricard | Procédé de synthèse du cis-3-hexene-1-ol à partir d'acide gras insaturé |
EP0443926A1 (fr) * | 1990-02-22 | 1991-08-28 | Elf Aquitaine | Procédé d'obtention d'irone par voie enzymatique |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0911414A1 (fr) * | 1997-10-23 | 1999-04-28 | Givaudan-Roure (International) Sa | Procédé pour la préparation des produits de la dégradation d'acides gras |
US6150145A (en) * | 1997-10-23 | 2000-11-21 | Givaudan Roure (International) Sa | Process for the production of degradation products of fatty acids |
Also Published As
Publication number | Publication date |
---|---|
EP0662141A1 (fr) | 1995-07-12 |
CA2145526A1 (fr) | 1994-04-14 |
FR2696192B1 (fr) | 1994-12-02 |
FR2696192A1 (fr) | 1994-04-01 |
US5705372A (en) | 1998-01-06 |
JPH08504084A (ja) | 1996-05-07 |
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