CA2117409A1 - Process for the extraction of antioxidant of vegetable origin in liquid form - Google Patents
Process for the extraction of antioxidant of vegetable origin in liquid formInfo
- Publication number
- CA2117409A1 CA2117409A1 CA002117409A CA2117409A CA2117409A1 CA 2117409 A1 CA2117409 A1 CA 2117409A1 CA 002117409 A CA002117409 A CA 002117409A CA 2117409 A CA2117409 A CA 2117409A CA 2117409 A1 CA2117409 A1 CA 2117409A1
- Authority
- CA
- Canada
- Prior art keywords
- vegetable
- oil
- antioxidant
- starting material
- mixture
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
- A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
- A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
- A23L3/3463—Organic compounds; Microorganisms; Enzymes
- A23L3/3472—Compounds of undetermined constitution obtained from animals or plants
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Botany (AREA)
- Microbiology (AREA)
- Polymers & Plastics (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Fats And Perfumes (AREA)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
- Compounds Of Unknown Constitution (AREA)
- Edible Oils And Fats (AREA)
- Steroid Compounds (AREA)
Abstract
The invention relates to a process for obtaining a liquid antioxidant extract from a vegetable material in which the vegetable material and an oil acting as vehicle are mixed and the mixture is pressed and filtered to obtain a clear oil containing the antioxidant.
Description
CA21 1 7~q This invention relates to a process for the extrac-tion of an antioxidant from a vegetable substance in liquid form.
The food industry uses antioxidants in order to retard the oxidative degradation of fats by inhibiting the formation of free radicals. The food-quality anti-oxidants typically used may be of synthetic origin, for example butylhydroxyanisole (BHA) and butylhydroxytoluene (BHT), although the use of synthetic antioxidants such as these is being increasingly opposed under food legisla-tion, but are preferably of natural origin and mainly vegetable origin in the form of plant extracts. Rosemary is currently the most widely used starting material for this purpose.
Various methods have been used to extract the antioxidant principles from the vegetable materials and to convert them into powder form or more or less viscous liquid form. Among the methods which lead to an anti-oxidant in powder form, a two-stage extraction process involving the successive use of hexane and ethanol is described for example in EP-A-0 307 626.
As an example of a process leading to an antioxidant in liquid form, EP-A-0 507 064 describes a process for solubilizing antioxidants of vegetable origin in a medium-chain triglyceride (MCT) by means of solvents. A
triglyceride such as this is liquid over an extremely wide temperature range, is resistant to oxidative degra-dation and has a good dissolving potential for antioxi-dants of vegetable origin.
The problem addressed by the present invention was to provide a clear, non-thixotropic liquid solution of antioxidants of vegetable origin in a lipidic support, which would not form any deposits in storage, by simple mechanical extraction which would not involve the use of solvents which would have to be eliminated.
CA2i 174~
Accordingly, the present invention relates to a process for the extraction of an antioxidant of vegetable origin in liquid form, characterized in that a vegetable material rich in phenolic antioxidants and an oil acting as vehicle are contacted, the resulting mixture is pressed under a pressure of 40bar or higher and is then filtered to remove the solids suspended therein without eliminating the oil used.
The vegetable starting material used may be any spice containing phenolic antioxidants, such as rosemary, sage, thyme, oregano, savory, ginger, turmeric, pimento or cocoa bean skins either individually or in admixture.
Of these starting materials, rosemary is a preferred material because it contains the antioxidants carnosic acid and carnosol which are odourless, colourless and substantially tasteless. The starting material may be fresh, whole or more or less finely ground. It may be stripped with steam to remove most of the odoriferous principles which are unwanted for certain applications where the antioxidant is required to be as neutral as possible. In other cases, it is desired to retain at least part of the odoriferous principles of the spices in the liquid antioxidant; in cases such as these, the starting material is not stripped. It is preferably in~5 dried form whether or not it has been ground or stripped.
The oil used as vehicle should be liquid at ambient temperature, should be a good solvent for the antioxidant principles and should be stable to oxidation, even at high temperatures. It is selected from a mixture of saturated C612 fatty acid triglycerides, olive oil, a hybrid safflower/sunflower oil, a hydrogenated and fractionated, non-lauric vegetable cottonseed or soybean oil. A polar triglyceride, for example of the medium chain type (MCT), containing caprylic and capric acids is preferably used.
~ ~ CA 2 i 1 74(~
The vegetable starting material and the oil may be mixed at ambient temperature, for example at around 20~C, where it is desired to retain at least part of the odoriferous principles of a starting material consisting of a cocktail of spices. Mixing may also be carried out at high temperatures of 100 to 140~C and preferably of the order of 120~C in cases where it is desired to produce a neutral antioxidant. This pretreatment may take place, for example, in a mixer with intensive stirring, in a scraped-surface heat exchanger or in a UHT
steam injector using superheated steam. The pretreatment time is preferably of the order of 60 minutes in a mixer to ensure suitable extraction of the antioxidants. In cases where a scraped-surface heat exchanger or a steam injector is used, the pretreatment time is preferably of the order of a few seconds to a few minutes.
It has been found to be of advantage to carry out the pretreatment in the presence of water by adding to the mixture a quantity of preferably about 10% by weight of water, based on the vegetable starting material, in order to increase the amount of antioxidant extracted.
In addition, an enzymatic pretreatment of the starting material enables the extraction yield to be increased by 20 to 30%, for example in the case of rosemary. To this end, the vegetable material, for example leaves of rosemary, is incubated with 1% by weight of a glucanase in aqueous medium, for example with stirring for about 4 h at around 40~C, after which the suspension is filtered or centrifuged and the vegetable material thus treated is dried.
The ratio by weight of oil to vegetable material is selected to obtain a high concentration of antioxidant with an acceptable yield and is preferably 0.3 to 0.7:1.
The pretreatment is followed by extraction under high pressure during which the suspension of vegetable C~2i 174~
material in the oil is also filtered. A press, preferab-ly in the form of a piston press equipped with a filter at its exit, is used for this purpose. The pressure applied is progressively increased, for example in stages to a value of 40 bar or higher and maintained for one or more hours.
In order further to increase the quantity of anti-oxidant extracted, the extraction process may be repeated by recycling a first extract of antioxidant in the oil and contacting it with a new batch of vegetable material.
It is thus possible to obtain a lipidic composition containing up to 7~ by weight of antioxidant.
The antioxidant extract may have to be decoloured and deodorized depending on the type of vegetable materi-al used, for example a spice, and the type of application envisaged. For decolouring, the lipidic composition is mixed with active charcoal or bleaching ear~, heated and filtered. The substances responsible for colour are thus retained on the adsorbent.
Deodorization is preferably carried out by vacuum distillation, for example in countercurrent in a falling-film or thin-layer apparatus using superheated steam.
The present invention also relates to a process for protecting the lipidic phase of a food, a cosmetic product or a pharmaceutical product, characterized in that an effective quantity of a lipidic composition containing an antioxidant of vegetable origin is incor-porated in the lipidic phase.
The invention is illustrated by the following Examples in which parts and percentages are by weight, unless otherwise indicated.
Example 1 250 ml of MCT are added with stirring to 500 g of chopped rosemary leaves which have been stripped with e ~ - CA2i 1 74 ~':q steam and the whole is kept for 60 minutes at 100~C in a Lodige~ mixer. After pressing for 60 minutes at 500 bar in a Carver~ piston press equipped with a filtration cage, a clear oil containing 1.76% of antioxidant (analyzed as the sum of carnosol and carnosic acid by high-perfor-mance liquidechromatography, HPLC) is collected. The yield is 63% (based on the MCT used).
Example 2 The procedure is as in Example 1, except that 250 ml of demineralized water are added to the chopped and stripped rosemary leaves before they are mixed with the MCT. A clear oil containing 2.11% of antioxidant is obtained. The yield, based on the MCT used, amounts to 57%.
Example 3 40 kg of steam-stripped and ground rosemary are moistened with 4 kg of demineralized water with stirring for 20 minutes at 120~C in a Lodige~ mixer. 20 kg of MCT
are then added at 100~C, after which the mixture is homogenized for 60 minutes at 100~C. The mixture is then pressed for 3 h at 70 bar in a Fujiwara~ piston press equipped a filtration cage. A clear oil containing 4.8%
of antioxidant is obtained in a yield of 66%, based on the MCT used.
Example 4 1 kg of non-stripped and ground rosemary leaves are treated with 100 ml of water and 500 ml of non-lauric vegetable oil rich in C18:1 trans, Durkex LC 550~, for 1 h at lOO C. Pressing as in Example 1 leads to a clear oil containing 1.3% of antioxidant in a yield of 55%
(based on the oil used).
~A 2 i .1 74 ~
Example 5 3 kg of stripped and ground rosemary are treated with 300 ml of demineralized water containing 1.5 kg of MCT for 60 minutes at 100~C. The mixture is then pressed as in Example 1 and 730 g of clear extract are collected.
1.46 kg of stripped and ground rosemary and 146 ml of demineralized water are added to the extract after which the mixture is treated for another 60 minutes at lOO C
and pressed as before. A clear oil containing 3.5% of antioxidant is thus collected.
Examples 6 - 9 6. 740 g of non-stripped and ground rosemary are treated with 7.5 g of Glucanex~ (Novo) for four hours at 40~C/pH 4 in the presence of 4.5 1 of water, after which the mixture is filtered and the residue is dried. 75 ml of demineralized water and then 370 g of MCT are added to the enzymatically treated vegetable material, after which the mixture is treated for 1 h at 100~C. Finally, the mixture is pressed as in Example 1 and a clear oil containing 1.95% of antioxidant is collected in a yield of 74%, based on the MCT used.
7. The same treatment as in Example 6 with 1% of enzyme Olivex~ (Novo) for 4 h at 35~C/pH 5.3 gives a clear oil containing 1.8% of antioxidant.
8. The treatment of rosemary as in Example 6 with the enzyme Rohament CT~ (Rohm) for 4 h at 45 C/pH 4 gives a clear oil containing 1.85% of antioxidant.
9. The same treatment as in Example 6 with the enzyme Rohament 0~ (Rohm) for 4 h at 50 C/pH 4.5 gives a clear oil containing 1.8% of antioxidant.
CA ~ i 1 /4QCl Example 10 200 g of dry non-stripped sage leaves are treatet with 100 ml of demineralized wa,er and then with 100 g of MCT for 1 h at 100~C, after which the mixture is pressed as in E.ample 1 in a Carver~ piston press equipped with a filtration cage. A clear oil is obtained in a yield of 68%, based on the MCT used.
Examples 11 - 13 11. 100 g of a cocktail of Provencal spices comprising 40% of rosemary, 20% of sage, 20% of thyme and 20% of oregano are treated as in Example 10 in the presence of 10 ml of demineralized water and 50 g of MCT except that the treatment is carried for 1 h at 20~C. After pres-sing, a clear oil is collected in a yield of 79%, based on the MCT used.
12. The same treatment as in Example 11 with 100 g of a cocktail of oriental spices comprising 50% of ginger, 25%
of turmeric and 25% of cayenne pepper gives a clear oil in a yield of 88%, based on the MCT used.
13. The same treatment as in Example 11 with 500 g of dry cocoa bean skins in the presence of 100 ml of de-mineralized water and 250 g of MCT, the extraction stepbeing carried out at 100~C, gives a yellow-coloured oil in a yield of 33%, based on the MCT used.
The food industry uses antioxidants in order to retard the oxidative degradation of fats by inhibiting the formation of free radicals. The food-quality anti-oxidants typically used may be of synthetic origin, for example butylhydroxyanisole (BHA) and butylhydroxytoluene (BHT), although the use of synthetic antioxidants such as these is being increasingly opposed under food legisla-tion, but are preferably of natural origin and mainly vegetable origin in the form of plant extracts. Rosemary is currently the most widely used starting material for this purpose.
Various methods have been used to extract the antioxidant principles from the vegetable materials and to convert them into powder form or more or less viscous liquid form. Among the methods which lead to an anti-oxidant in powder form, a two-stage extraction process involving the successive use of hexane and ethanol is described for example in EP-A-0 307 626.
As an example of a process leading to an antioxidant in liquid form, EP-A-0 507 064 describes a process for solubilizing antioxidants of vegetable origin in a medium-chain triglyceride (MCT) by means of solvents. A
triglyceride such as this is liquid over an extremely wide temperature range, is resistant to oxidative degra-dation and has a good dissolving potential for antioxi-dants of vegetable origin.
The problem addressed by the present invention was to provide a clear, non-thixotropic liquid solution of antioxidants of vegetable origin in a lipidic support, which would not form any deposits in storage, by simple mechanical extraction which would not involve the use of solvents which would have to be eliminated.
CA2i 174~
Accordingly, the present invention relates to a process for the extraction of an antioxidant of vegetable origin in liquid form, characterized in that a vegetable material rich in phenolic antioxidants and an oil acting as vehicle are contacted, the resulting mixture is pressed under a pressure of 40bar or higher and is then filtered to remove the solids suspended therein without eliminating the oil used.
The vegetable starting material used may be any spice containing phenolic antioxidants, such as rosemary, sage, thyme, oregano, savory, ginger, turmeric, pimento or cocoa bean skins either individually or in admixture.
Of these starting materials, rosemary is a preferred material because it contains the antioxidants carnosic acid and carnosol which are odourless, colourless and substantially tasteless. The starting material may be fresh, whole or more or less finely ground. It may be stripped with steam to remove most of the odoriferous principles which are unwanted for certain applications where the antioxidant is required to be as neutral as possible. In other cases, it is desired to retain at least part of the odoriferous principles of the spices in the liquid antioxidant; in cases such as these, the starting material is not stripped. It is preferably in~5 dried form whether or not it has been ground or stripped.
The oil used as vehicle should be liquid at ambient temperature, should be a good solvent for the antioxidant principles and should be stable to oxidation, even at high temperatures. It is selected from a mixture of saturated C612 fatty acid triglycerides, olive oil, a hybrid safflower/sunflower oil, a hydrogenated and fractionated, non-lauric vegetable cottonseed or soybean oil. A polar triglyceride, for example of the medium chain type (MCT), containing caprylic and capric acids is preferably used.
~ ~ CA 2 i 1 74(~
The vegetable starting material and the oil may be mixed at ambient temperature, for example at around 20~C, where it is desired to retain at least part of the odoriferous principles of a starting material consisting of a cocktail of spices. Mixing may also be carried out at high temperatures of 100 to 140~C and preferably of the order of 120~C in cases where it is desired to produce a neutral antioxidant. This pretreatment may take place, for example, in a mixer with intensive stirring, in a scraped-surface heat exchanger or in a UHT
steam injector using superheated steam. The pretreatment time is preferably of the order of 60 minutes in a mixer to ensure suitable extraction of the antioxidants. In cases where a scraped-surface heat exchanger or a steam injector is used, the pretreatment time is preferably of the order of a few seconds to a few minutes.
It has been found to be of advantage to carry out the pretreatment in the presence of water by adding to the mixture a quantity of preferably about 10% by weight of water, based on the vegetable starting material, in order to increase the amount of antioxidant extracted.
In addition, an enzymatic pretreatment of the starting material enables the extraction yield to be increased by 20 to 30%, for example in the case of rosemary. To this end, the vegetable material, for example leaves of rosemary, is incubated with 1% by weight of a glucanase in aqueous medium, for example with stirring for about 4 h at around 40~C, after which the suspension is filtered or centrifuged and the vegetable material thus treated is dried.
The ratio by weight of oil to vegetable material is selected to obtain a high concentration of antioxidant with an acceptable yield and is preferably 0.3 to 0.7:1.
The pretreatment is followed by extraction under high pressure during which the suspension of vegetable C~2i 174~
material in the oil is also filtered. A press, preferab-ly in the form of a piston press equipped with a filter at its exit, is used for this purpose. The pressure applied is progressively increased, for example in stages to a value of 40 bar or higher and maintained for one or more hours.
In order further to increase the quantity of anti-oxidant extracted, the extraction process may be repeated by recycling a first extract of antioxidant in the oil and contacting it with a new batch of vegetable material.
It is thus possible to obtain a lipidic composition containing up to 7~ by weight of antioxidant.
The antioxidant extract may have to be decoloured and deodorized depending on the type of vegetable materi-al used, for example a spice, and the type of application envisaged. For decolouring, the lipidic composition is mixed with active charcoal or bleaching ear~, heated and filtered. The substances responsible for colour are thus retained on the adsorbent.
Deodorization is preferably carried out by vacuum distillation, for example in countercurrent in a falling-film or thin-layer apparatus using superheated steam.
The present invention also relates to a process for protecting the lipidic phase of a food, a cosmetic product or a pharmaceutical product, characterized in that an effective quantity of a lipidic composition containing an antioxidant of vegetable origin is incor-porated in the lipidic phase.
The invention is illustrated by the following Examples in which parts and percentages are by weight, unless otherwise indicated.
Example 1 250 ml of MCT are added with stirring to 500 g of chopped rosemary leaves which have been stripped with e ~ - CA2i 1 74 ~':q steam and the whole is kept for 60 minutes at 100~C in a Lodige~ mixer. After pressing for 60 minutes at 500 bar in a Carver~ piston press equipped with a filtration cage, a clear oil containing 1.76% of antioxidant (analyzed as the sum of carnosol and carnosic acid by high-perfor-mance liquidechromatography, HPLC) is collected. The yield is 63% (based on the MCT used).
Example 2 The procedure is as in Example 1, except that 250 ml of demineralized water are added to the chopped and stripped rosemary leaves before they are mixed with the MCT. A clear oil containing 2.11% of antioxidant is obtained. The yield, based on the MCT used, amounts to 57%.
Example 3 40 kg of steam-stripped and ground rosemary are moistened with 4 kg of demineralized water with stirring for 20 minutes at 120~C in a Lodige~ mixer. 20 kg of MCT
are then added at 100~C, after which the mixture is homogenized for 60 minutes at 100~C. The mixture is then pressed for 3 h at 70 bar in a Fujiwara~ piston press equipped a filtration cage. A clear oil containing 4.8%
of antioxidant is obtained in a yield of 66%, based on the MCT used.
Example 4 1 kg of non-stripped and ground rosemary leaves are treated with 100 ml of water and 500 ml of non-lauric vegetable oil rich in C18:1 trans, Durkex LC 550~, for 1 h at lOO C. Pressing as in Example 1 leads to a clear oil containing 1.3% of antioxidant in a yield of 55%
(based on the oil used).
~A 2 i .1 74 ~
Example 5 3 kg of stripped and ground rosemary are treated with 300 ml of demineralized water containing 1.5 kg of MCT for 60 minutes at 100~C. The mixture is then pressed as in Example 1 and 730 g of clear extract are collected.
1.46 kg of stripped and ground rosemary and 146 ml of demineralized water are added to the extract after which the mixture is treated for another 60 minutes at lOO C
and pressed as before. A clear oil containing 3.5% of antioxidant is thus collected.
Examples 6 - 9 6. 740 g of non-stripped and ground rosemary are treated with 7.5 g of Glucanex~ (Novo) for four hours at 40~C/pH 4 in the presence of 4.5 1 of water, after which the mixture is filtered and the residue is dried. 75 ml of demineralized water and then 370 g of MCT are added to the enzymatically treated vegetable material, after which the mixture is treated for 1 h at 100~C. Finally, the mixture is pressed as in Example 1 and a clear oil containing 1.95% of antioxidant is collected in a yield of 74%, based on the MCT used.
7. The same treatment as in Example 6 with 1% of enzyme Olivex~ (Novo) for 4 h at 35~C/pH 5.3 gives a clear oil containing 1.8% of antioxidant.
8. The treatment of rosemary as in Example 6 with the enzyme Rohament CT~ (Rohm) for 4 h at 45 C/pH 4 gives a clear oil containing 1.85% of antioxidant.
9. The same treatment as in Example 6 with the enzyme Rohament 0~ (Rohm) for 4 h at 50 C/pH 4.5 gives a clear oil containing 1.8% of antioxidant.
CA ~ i 1 /4QCl Example 10 200 g of dry non-stripped sage leaves are treatet with 100 ml of demineralized wa,er and then with 100 g of MCT for 1 h at 100~C, after which the mixture is pressed as in E.ample 1 in a Carver~ piston press equipped with a filtration cage. A clear oil is obtained in a yield of 68%, based on the MCT used.
Examples 11 - 13 11. 100 g of a cocktail of Provencal spices comprising 40% of rosemary, 20% of sage, 20% of thyme and 20% of oregano are treated as in Example 10 in the presence of 10 ml of demineralized water and 50 g of MCT except that the treatment is carried for 1 h at 20~C. After pres-sing, a clear oil is collected in a yield of 79%, based on the MCT used.
12. The same treatment as in Example 11 with 100 g of a cocktail of oriental spices comprising 50% of ginger, 25%
of turmeric and 25% of cayenne pepper gives a clear oil in a yield of 88%, based on the MCT used.
13. The same treatment as in Example 11 with 500 g of dry cocoa bean skins in the presence of 100 ml of de-mineralized water and 250 g of MCT, the extraction stepbeing carried out at 100~C, gives a yellow-coloured oil in a yield of 33%, based on the MCT used.
Claims (10)
1. A process for the extraction of an antioxidant of vegetable origin in liquid form, characterized in that a vegetable material rich in phenolic antioxidants and an oil acting as vehicle are contacted, the resulting mixture is pressed under a pressure of 40 bar or higher and is then filtered to remove the solids suspended therein without eliminating the oil used.
2. A process as claimed in claim 1, characterized in that the vegetable starting material used is any spice containing phenolic antioxidants, more particularly rosemary, sage, thyme, oregano, savory, ginger, turmeric, pimento or cocoa bean skins used either individually or in admixture.
3. A process as claimed in claim 1, characterized in that the oil used as vehicle is selected from a mixture of saturated C6-12 fatty acid triglycerides, olive oil, a hybrid safflower/sunflower oil or a hydrogenated and fractionated, non-lauric vegetable cottonseed or soybean oil.
4. A process as claimed in claim 1, characterized in that the vegetable starting material and the oil are mixed at ambient temperature to retain the aromatic principles.
5. A process as claimed in claim 1, characterized in that the vegetable starting material and the oil are mixed at a high temperature of 100 to 140°C and preferably around 120°C.
6. A process as claimed in claim 4 or 5, characterized in that the pretreatment is carried out in the presence of water by adding to the mixture a quantity of preferably about 10% by weight of water, based on the vegetable material.
7. A process as claimed in claim 4 or 5, characterized in that the starting material is subjected to an enzymatic pretreatment by incubating it with a glucanase in aqueous medium, filtering or centrifuging the suspension and drying the vegetable material thus treated.
8. A process as claimed in claim 4 or 5, characterized in that the ratio by weight of oil to vegetable material is 0.3 to 0.7:1.
9. A process as claimed in claim 1, characterized in that pressing is carried out in a piston press equipped with a filtration cage so that pressing and filtration can be completed in a single step.
10. A process for protecting the lipidic phase of a food, a cosmetic product or a pharmaceutical product, characterized in that an effective quantity of a lipidic composition containing an antioxidant of vegetable origin obtained by the process claimed in any of claims 1 to 9 is incorporated in the lipidic phase.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP93113120.5 | 1993-08-17 | ||
| EP93113120A EP0639336B1 (en) | 1993-08-17 | 1993-08-17 | Process for extracting antioxydants of vegetable origin as liquids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2117409A1 true CA2117409A1 (en) | 1995-02-18 |
Family
ID=8213183
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002117409A Abandoned CA2117409A1 (en) | 1993-08-17 | 1994-07-25 | Process for the extraction of antioxidant of vegetable origin in liquid form |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0639336B1 (en) |
| JP (1) | JPH07173465A (en) |
| AT (1) | ATE163838T1 (en) |
| CA (1) | CA2117409A1 (en) |
| DE (1) | DE69317419T2 (en) |
| ES (1) | ES2114982T3 (en) |
| GR (1) | GR3026539T3 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0728421A1 (en) * | 1995-02-21 | 1996-08-28 | Societe Des Produits Nestle S.A. | Antioxidant extraction process from plant material |
| EP0728420A1 (en) * | 1995-02-21 | 1996-08-28 | Societe Des Produits Nestle S.A. | Antioxidant extraction process from plant material |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU6455596A (en) * | 1995-07-14 | 1997-02-18 | Sabinsa Corporation | Bioprotectant composition, method of use and extraction process of curcuminoids |
| US5902622A (en) * | 1996-06-04 | 1999-05-11 | Konstantinos Poulgouras | Natural heat stable flavorings for bakery applications |
| EP0811678A1 (en) † | 1996-06-08 | 1997-12-10 | Societe Des Produits Nestle S.A. | Extraction of antioxidants |
| US8277852B2 (en) * | 2002-01-25 | 2012-10-02 | Akzo Nobel Surface Chemistry Llc | Bioactive botanical cosmetic compositions and processes for their production |
| US7442391B2 (en) * | 2002-01-25 | 2008-10-28 | Integrated Botanical Technologies, Llc | Bioactive botanical cosmetic compositions and processes for their production |
| JP5308121B2 (en) * | 2008-11-04 | 2013-10-09 | サミット製油株式会社 | Method for producing pepper oil and method for producing food |
| JP5308124B2 (en) * | 2008-11-11 | 2013-10-09 | サミット製油株式会社 | Method for producing salamander oil and method for producing food |
| FR2943684B1 (en) * | 2009-03-30 | 2011-04-22 | Castera Anne Rossignol | PROCESS FOR EXTRACTING NON-VOLATILE COMPOUNDS |
| JP2013001666A (en) * | 2011-06-14 | 2013-01-07 | Yasuharu Omura | Nutrient composition |
| FR2986534B1 (en) | 2012-02-07 | 2014-06-27 | Univ D'avignon Et Des Pays De Vaucluse | PROCESS FOR ENRICHING A CAROTENOID FAT BODY |
| DE102015111743B4 (en) * | 2015-07-20 | 2019-05-23 | Sensient Colors Europe Gmbh | Process for the preparation of coloring preparations using enzymes, the coloring preparations themselves and foods containing them |
| FR3110342A1 (en) * | 2020-05-21 | 2021-11-26 | Id4Feed | Process for preparing a totum or a filtrate allowing the stabilization of fresh plant material |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2115073A (en) * | 1936-02-06 | 1938-04-26 | Glidden Co | Salad dressing and flavoring therefor |
| US3950266A (en) * | 1973-11-28 | 1976-04-13 | Rutgers Research And Educational Foundation | Method of producing an antioxidant composition from rosemary and sage |
| JPS56144078A (en) * | 1980-04-08 | 1981-11-10 | Lion Corp | Preparation of preservative |
| CH647654A5 (en) * | 1980-05-14 | 1985-02-15 | Knorr Naehrmittel Ag | METHOD FOR PRODUCING AROMA CONCENTRATES FROM VEGETABLE AND / OR ANIMAL SUBSTANCES. |
| JPS58162258A (en) * | 1982-03-19 | 1983-09-26 | Kao Corp | Making method for liquid spice |
| CH672048A5 (en) * | 1987-09-16 | 1989-10-31 | Nestle Sa | |
| DE69202716T2 (en) * | 1991-03-30 | 1995-10-12 | Nestle Sa | Process for the preparation of a liquid antioxidant extract from spices. |
-
1993
- 1993-08-17 DE DE69317419T patent/DE69317419T2/en not_active Expired - Lifetime
- 1993-08-17 EP EP93113120A patent/EP0639336B1/en not_active Expired - Lifetime
- 1993-08-17 ES ES93113120T patent/ES2114982T3/en not_active Expired - Lifetime
- 1993-08-17 AT AT93113120T patent/ATE163838T1/en not_active IP Right Cessation
-
1994
- 1994-07-25 CA CA002117409A patent/CA2117409A1/en not_active Abandoned
- 1994-08-16 JP JP6192404A patent/JPH07173465A/en not_active Withdrawn
-
1998
- 1998-04-03 GR GR980400723T patent/GR3026539T3/en unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0728421A1 (en) * | 1995-02-21 | 1996-08-28 | Societe Des Produits Nestle S.A. | Antioxidant extraction process from plant material |
| EP0728420A1 (en) * | 1995-02-21 | 1996-08-28 | Societe Des Produits Nestle S.A. | Antioxidant extraction process from plant material |
| US5795609A (en) * | 1995-02-21 | 1998-08-18 | Nestec S.A. | Alkylene glycol extraction of antioxidants from vegetable matter |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE163838T1 (en) | 1998-03-15 |
| DE69317419T2 (en) | 1998-07-02 |
| JPH07173465A (en) | 1995-07-11 |
| EP0639336B1 (en) | 1998-03-11 |
| EP0639336A1 (en) | 1995-02-22 |
| ES2114982T3 (en) | 1998-06-16 |
| DE69317419D1 (en) | 1998-04-16 |
| GR3026539T3 (en) | 1998-07-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |