US20120232163A1 - Methods of making olive juice extracts containing reduced solids - Google Patents
Methods of making olive juice extracts containing reduced solids Download PDFInfo
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- US20120232163A1 US20120232163A1 US13/480,442 US201213480442A US2012232163A1 US 20120232163 A1 US20120232163 A1 US 20120232163A1 US 201213480442 A US201213480442 A US 201213480442A US 2012232163 A1 US2012232163 A1 US 2012232163A1
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- US
- United States
- Prior art keywords
- olive juice
- olive
- juice extract
- extract
- elevated temperature
- 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
- 235000011389 fruit/vegetable juice Nutrition 0.000 title claims abstract description 88
- 240000007817 Olea europaea Species 0.000 title claims abstract description 87
- 239000007787 solid Substances 0.000 title claims abstract description 19
- 239000000284 extract Substances 0.000 title claims description 42
- 238000000034 method Methods 0.000 title claims description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 48
- 239000002904 solvent Substances 0.000 claims abstract description 23
- JUUBCHWRXWPFFH-UHFFFAOYSA-N Hydroxytyrosol Chemical compound OCCC1=CC=C(O)C(O)=C1 JUUBCHWRXWPFFH-UHFFFAOYSA-N 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 27
- 235000003248 hydroxytyrosol Nutrition 0.000 claims description 20
- 229940095066 hydroxytyrosol Drugs 0.000 claims description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 19
- 235000013824 polyphenols Nutrition 0.000 claims description 10
- 150000008442 polyphenolic compounds Chemical class 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- 235000016709 nutrition Nutrition 0.000 claims description 6
- 238000001704 evaporation Methods 0.000 claims description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 238000005119 centrifugation Methods 0.000 claims description 3
- 239000002537 cosmetic Substances 0.000 claims description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- 238000001694 spray drying Methods 0.000 claims description 2
- 239000003002 pH adjusting agent Substances 0.000 claims 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 238000004108 freeze drying Methods 0.000 claims 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 1
- 239000000835 fiber Substances 0.000 abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 239000007858 starting material Substances 0.000 description 14
- YCCILVSKPBXVIP-UHFFFAOYSA-N 2-(4-hydroxyphenyl)ethanol Chemical compound OCCC1=CC=C(O)C=C1 YCCILVSKPBXVIP-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 235000015872 dietary supplement Nutrition 0.000 description 6
- 239000004006 olive oil Substances 0.000 description 6
- 235000008390 olive oil Nutrition 0.000 description 6
- 238000005054 agglomeration Methods 0.000 description 5
- 230000002776 aggregation Effects 0.000 description 5
- 235000019658 bitter taste Nutrition 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- DBLDQZASZZMNSL-QMMMGPOBSA-N L-tyrosinol Natural products OC[C@@H](N)CC1=CC=C(O)C=C1 DBLDQZASZZMNSL-QMMMGPOBSA-N 0.000 description 4
- 150000001720 carbohydrates Chemical class 0.000 description 4
- 235000014633 carbohydrates Nutrition 0.000 description 4
- 235000013399 edible fruits Nutrition 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 235000004330 tyrosol Nutrition 0.000 description 4
- RFWGABANNQMHMZ-UHFFFAOYSA-N 8-acetoxy-7-acetyl-6,7,7a,8-tetrahydro-5H-benzo[g][1,3]dioxolo[4',5':4,5]benzo[1,2,3-de]quinoline Natural products CC=C1C(CC(=O)OCCC=2C=C(O)C(O)=CC=2)C(C(=O)OC)=COC1OC1OC(CO)C(O)C(O)C1O RFWGABANNQMHMZ-UHFFFAOYSA-N 0.000 description 3
- HKVGJQVJNQRJPO-UHFFFAOYSA-N Demethyloleuropein Natural products O1C=C(C(O)=O)C(CC(=O)OCCC=2C=C(O)C(O)=CC=2)C(=CC)C1OC1OC(CO)C(O)C(O)C1O HKVGJQVJNQRJPO-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- RFWGABANNQMHMZ-HYYSZPHDSA-N Oleuropein Chemical compound O([C@@H]1OC=C([C@H](C1=CC)CC(=O)OCCC=1C=C(O)C(O)=CC=1)C(=O)OC)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O RFWGABANNQMHMZ-HYYSZPHDSA-N 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 235000011576 oleuropein Nutrition 0.000 description 3
- RFWGABANNQMHMZ-CARRXEGNSA-N oleuropein Natural products COC(=O)C1=CO[C@@H](O[C@H]2O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]2O)C(=CC)[C@H]1CC(=O)OCCc3ccc(O)c(O)c3 RFWGABANNQMHMZ-CARRXEGNSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- 206010013911 Dysgeusia Diseases 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 235000017807 phytochemicals Nutrition 0.000 description 1
- 229930000223 plant secondary metabolite Natural products 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C05—FERTILISERS; MANUFACTURE THEREOF
- C05B—PHOSPHATIC FERTILISERS
- C05B13/00—Fertilisers produced by pyrogenic processes from phosphatic materials
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K10/00—Animal feeding-stuffs
- A23K10/30—Animal feeding-stuffs from material of plant origin, e.g. roots, seeds or hay; from material of fungal origin, e.g. mushrooms
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K10/00—Animal feeding-stuffs
- A23K10/30—Animal feeding-stuffs from material of plant origin, e.g. roots, seeds or hay; from material of fungal origin, e.g. mushrooms
- A23K10/37—Animal feeding-stuffs from material of plant origin, e.g. roots, seeds or hay; from material of fungal origin, e.g. mushrooms from waste material
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/111—Aromatic compounds
-
- 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
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/02—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation containing fruit or vegetable juices
- A23L2/04—Extraction of juices
-
- 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
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/385—Concentrates of non-alcoholic beverages
- A23L2/39—Dry compositions
-
- 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
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
-
- 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
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
- A61K8/9783—Angiosperms [Magnoliophyta]
- A61K8/9789—Magnoliopsida [dicotyledons]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/30—Fuel from waste, e.g. synthetic alcohol or diesel
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P60/00—Technologies relating to agriculture, livestock or agroalimentary industries
- Y02P60/80—Food processing, e.g. use of renewable energies or variable speed drives in handling, conveying or stacking
- Y02P60/87—Re-use of by-products of food processing for fodder production
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W30/00—Technologies for solid waste management
- Y02W30/40—Bio-organic fraction processing; Production of fertilisers from the organic fraction of waste or refuse
Definitions
- This invention relates to olive juice extracts containing an decreased amount of solids, and to methods of making these extracts.
- Olive juice extracts can be used as nutritional supplements, as they have potent antioxidant activities.
- Nutritional compositions containing these novel extracts are also part of this invention.
- this invention relates to a method of removing at least some of the solids present in an olive juice comprising: a) adding a water-miscible or nearly water-miscible solvent in an amount (by volume) equal to about 40-400% of the olive juice to form two phases; and b) separating the phases.
- a typical olive will contain approximately 50% water, 22% oil, 19% carbohydrates, 6% cellulose, 2% proteins, and oleuropein and hydroxytyrosol (combined) 0.2%. It should be appreciated that the exact makeup of the fruit (and its subsequent extract) will vary according to the variety of olive used, the time of harvest, and even growing conditions.
- HT means hydroxytyrosol
- “Olive Juice”, “Olive Waste Water” and “Vegetation Water” are terms all intended to be used interchangeably. They refer to the water phase produced during olive oil production. It is a slurry with a complex mixture of carbohydrates along with the compounds of interest, such as HT and oleuropein (which contains bound HT, and which may be subsequently broken down to yield HT).
- Any form of olive juice may be used as a starting material for the processes of this invention, although minor variations of the processes may be required for optimal results.
- Fresh juice typically containing about 85-90% water and 10-15% solid matter can be purchased and used as a starting material in the processes of this invention.
- Other forms of commercially available olive juice which have been filtered by the supplier to remove some or all of the solids, are also appropriate starting materials, as well.
- the olive juice may be conveniently purchased in a stabilized, freeze dried form where citric acid has been added to stabilize it, for example, HIDROX from CreAgri (California, USA).
- Dried olive juice typically contains about 60% carbohydrates, 10% fibres, 10% fat, and 6% polyphenols (this includes approximately 2% hydroxytyrosol, 0.2% tyrosol and other polyphenols), and organic acids, proteins and minerals.
- this dried form as a starting material for this invention, it should be hydrated.
- the resulting juice is a preferred starting material.
- the polyphenol concentration of any type of olive juice can be increased by maintaining the olive juice at an elevated temperature and increasing the pH to at least 6.
- the elevated temperature can exist over a wide range, i.e. from about 20 degrees C. up to about 100 degrees C.
- the actual temperature is not especially critical, as long as it is under the boiling point of the olive juice.
- Preferred temperature ranges are from about 60 to about 80 degrees C., and a more preferred temperature is about 80 degrees C.
- the pH of the juice should be adjusted to a higher pH than is originally present in the untreated olive juice.
- the adjusted pH should be in a range of about 6 to about 11, with the preferred pH being from about 7 to about 10, and a more preferred range is from about 8 to about 9.
- a pH above about 10 can result in the degradation of the final HT, so it is not preferred.
- Any basic compound capable of adjusting pH can be used: preferred compounds are NaOH, KOH, and mixtures thereof.
- the amount needed will vary from batch to batch, but a typical amount needed will be approximately 10-15% by weight based on the weight of the batch.
- the juice will contain a higher amount of HT than the starting material.
- the pH may change, and re-adjustment(s) may be required to maintain the desired pH. It is preferred to continually adjust the pH during the time of the reaction.
- One way of determining that the reactions are substantially complete is that the pH will remain relatively stable (i.e. relatively unchanged) for at least about ten minutes. The amount of time it will take for a batch to reach the point of stability for about 10 minutes can vary greatly depending on the individual composition to of the batch. Generally, as higher the temperature and the pH the less time the reaction will take.
- this invention also includes a process for removing the bitterness from an olive juice extract comprising raising the temperature and pH of the olive juice to the above-mentioned conditions.
- the olive juice may be process as desired, using any of the known process steps in the art, or, optionally steps presented below.
- the starting material for this step may be the de-bittered, HT enhanced juice made in accordance with the above description A, or it may be any starting material (such as those described in Section A as suitable as starting materials for the optional step described there. Generally concentrated juice is preferred for economic reasons, but the method will work with a variety of juices. Thus, the starting material may have solids, fats (oils) and/or fibers present in it.
- unprocessed olive juice will contain a large amount of fine fibers. These are difficult to filter out as they tend to clog membrane filters, requiring a large amount of maintenance. It has been found, as another aspect of this invention, that fibers, residual oil and lipids, and/or other solids present in the olive juice can be agglomerated and then easily removed by a) adding a solvent in an amount (by volume) equal to about 40-400% of the olive juice or partially concentrated olive juice to form two phases; and then b) separating the two phases.
- the solvent which can be employed in this process can be any solvent or mixture of solvents which is water-miscible or nearly miscible like n-butanol.
- Alcohols, especially C1 to C4 (or mixtures thereof) are preferred, and ethanol is particularly preferred, especially when the end product is to be used in food or as part of a medicinal or nutritional supplement product.
- Other solvents which can also be utilized include: acetonitrile, acetone, and glycol.
- the amount of solvent is not especially critical, and will depend on the amount of water in the mixture. Usually the solvent will be needed in an amount that is at least equal to the amount of water present. For example, if ethanol is the solvent, for every 500 ml of water, about 600 ml of EtOH will be required. However, this is subject to a wide range: from about 40-400% solvent compared to the amount of water by weight, preferably 100-240%, and more preferably about 160-220% solvent compared to the amount of water. The important criteria is that enough solvent is added so that two distinct phases are formed.
- the temperature of this step is not particularly critical and may range from 0 degrees Celsius to about 80 degrees Celsius, or any temperature which is less than the boiling point of the mixture. Conveniently the temperature will be between about 20 and 60 degrees C., and most conveniently is room temperature, or about 25 degrees.
- any convenient means can be used to separate the two phases.
- the method of separation will depend on the actual make up of the material. For some batches, a filter can now be easily used, and/or a centrifuge. Other batches could be easily processed by simple decantation (if not too many solids were present, or if material is stuck to the wall of the vessel) or ordinary phase separation.
- this same process can be used with a starting olive juice which has been processed to remove fibers, but which has undergone the de-bittering/HT concentrating step described in the previous section. Addition of the solvent and separation of the resultant phases will allow separation of any precipitates which may have formed during the debittering process.
- the solvent can be recovered for re-use, if desired, making the process more economical. Evaporation is generally the easiest way to so recover the solvent. At this point, is has been found in yet another aspect of the invention, that if one chooses to employ an evaporation step to recover the solvent, then adjusting the pH of the extract to below 6, preferably below 5, will prevent unwanted foaming during the evaporation process.
- the resulting non-bitter, solids-free olive juice extract which forms another aspect of this invention can be used as is in any way desired.
- a nutritional composition for example a food or beverage composition.
- the food can be suitable for humans consumption, or can be an animal feed.
- it can be made into a nutritional supplement, for example, it can be formulated into capsules, tablets, or the like using known methods.
- the composition can be used in cosmetic compositions.
- the non-bitter, solids-free extract is spray dried or free-dried using conventional techniques to form a powder derivative, and then incorporated into a final product.
- stabilizers and the like amy be added to the juice prior to the drying step.
- the resulting powder can be directly incorporated into a nutritional composition, or it can be an animal feed. Alternatively, it can be made into a nutritional supplement; for examples it can be formulated into capsules, tablets, or the like using known methods. Alternatively, the composition can be used in cosmetic compositions.
- the non-bitter, solids-free extract is subjected to additional processing steps, such as de-fatting, further extraction, or distillation of the HT.
- additional processing steps such as de-fatting, further extraction, or distillation of the HT.
- Such processes may be known techniques, or the techniques as further described in co-pending patent application U.S. application Ser. No. 12/647,032 filed on Feb. 18, 2010 may be used.
- HIDROX 6% from CreAgri, Haywood, Calif. Its content is: (in Lot 6022406002. This is freeze-dried olive juice which has been stabilized with citric acid. weight %):
- Carbohydrates Approx. 60% Lipids (olive oil) Approx. 15% Fibers Approx. 10% Hydroxytyrosol 2.1% Water Approx. 2%
- Solubility in water a turbid, fine suspension Taste bitter Color beige-brown powder
- HIDROX (CreAgri, from Example 1) 6% polyphenols, and 80 ml water were added to a reaction flask in a nitrogen atmosphere. The mixture was warmed up to 80° C. and adjusted to pH 9.0, followed by stirring for 30 minutes at 80° C. at pH 9.0 with continuous addition of a total of 38 ml sodium hydroxide 10 mol/l to maintain pH. The suspension was cooled to 60° C.
- the content of hydroxytyrosol increased by the base treatment to approx. 130%.
- the filtrate was adjusted to pH 5 with approx. 5 ml hydrochloric acid 10 mol/l and evaporated at the rotavapor (20 mbar, 60° C.) to recover the ethanol, the non volatile residue 33.5 g.
- the extract is not bitter at 1 mg/ml water
- yield % refers to the content of HT in the dried filtrate [w %]. Yield [w %] is based on the initial content of the starting material, HIDROX 6%.
- the content of hydroxytyrosol increased by the base treatment to approx. 115%.
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Abstract
Solids, including fibers can be easily removed from olive juice by mixing the olive juice with a water-miscible solvent to form two phases and separating the phases. Preferably the solvent is ethanol.
Description
- This application is a divisional of commonly owned co-pending U.S. Application Ser. No. 12/674,044 filed Feb. 18, 2010, which is the national phase under 35 USC §371 of International Application No. PCT/EP2008/006790 filed Aug. 19, 2008, which designated the U.S. and claims priority to Europe Application No. 07016344.9 filed Aug. 21, 2007, the entire contents of each of which are hereby incorporated by reference.
- This invention relates to olive juice extracts containing an decreased amount of solids, and to methods of making these extracts. Olive juice extracts can be used as nutritional supplements, as they have potent antioxidant activities. Nutritional compositions containing these novel extracts are also part of this invention.
- The medicinal benefits of olive oil and olive extracts is widely being recognized. To make olive oil, the olive fruits are ground into a paste. Pressure is applied to the paste to separate the oil from the ground fruit. In addition to providing olive oil, the pressing also releases the water content of the olive fruit, which contains many water soluble phytochemicals. This water is known by a number of names, including “vegetation water, olive juice, and olive waste water”. Interestingly, while olive juice and its disposal can be a problem for the olive oil producer, this olive juice can be a desirable rich source of phenolic compounds, which can have beneficial nutritional properties.
- In the past, methods to concentrate the nutritional olive juice involved time consuming incubation, filtration and/or centrifugation, and/or spray drying steps. Another problem is that the usability of dried or liquid olive juice in food or dietary supplements is limited due to the smell, bitterness, and turbidity of the olive juice, as well as the low content of hydroxytyrosol, one of the active polyphenols.
- It would therefore be desirable to develop a better method for producing an all-natural, hydroxytyrosol-rich, non-bitter olive juice extract which is efficient and cost-effective.
- In accordance with this invention, new processes for making an all-natural, hydroxytyrosol-rich, non bitter olive juice extract are presented. Also as part of this invention are novel juice extract, and compositions containing this novel olive juice extracts. Thus this invention relates to a method of removing at least some of the solids present in an olive juice comprising: a) adding a water-miscible or nearly water-miscible solvent in an amount (by volume) equal to about 40-400% of the olive juice to form two phases; and b) separating the phases.
- A typical olive will contain approximately 50% water, 22% oil, 19% carbohydrates, 6% cellulose, 2% proteins, and oleuropein and hydroxytyrosol (combined) 0.2%. It should be appreciated that the exact makeup of the fruit (and its subsequent extract) will vary according to the variety of olive used, the time of harvest, and even growing conditions.
- Contrary to literature reports (see e.g., Briante et al, 2002, J. Biotechn. 93: 109-119, and Soler-Rivas et al 2000, J Sci Food Agric 80:1013-1023) it has been found, in accordance with this invention, that the unknown compounds which impart a bitter taste to the olive juice are neither hydroxytyrosol nor oleuropein. While not wishing to be bound by theory, they may contain a labile phenolic ester group. Regardless of the identity of the bitter compounds, they are very sensitive to base, and are not stable at higher pH.
- As used throughout the specification and claims, the following definitions apply:
- “HT” means hydroxytyrosol.
- “Olive Juice”, “Olive Waste Water” and “Vegetation Water” are terms all intended to be used interchangeably. They refer to the water phase produced during olive oil production. It is a slurry with a complex mixture of carbohydrates along with the compounds of interest, such as HT and oleuropein (which contains bound HT, and which may be subsequently broken down to yield HT).
- The following step is an optional, but preferred step in the practice of this invention. Reference is made to co-pending U.S. application Ser. No. 12/674,213 filed on Jun. 6, 2011. If desired, the process can begin with the procedures described in Section B, below.
- Any form of olive juice may be used as a starting material for the processes of this invention, although minor variations of the processes may be required for optimal results. Fresh juice typically containing about 85-90% water and 10-15% solid matter can be purchased and used as a starting material in the processes of this invention. Other forms of commercially available olive juice which have been filtered by the supplier to remove some or all of the solids, are also appropriate starting materials, as well. Also appropriate is olive juice which is purchased in a concentrated form (for example, 3-4×), or concentrated prior to use by simple evaporating techniques known in the art.
- In other cases, the olive juice may be conveniently purchased in a stabilized, freeze dried form where citric acid has been added to stabilize it, for example, HIDROX from CreAgri (California, USA). Dried olive juice typically contains about 60% carbohydrates, 10% fibres, 10% fat, and 6% polyphenols (this includes approximately 2% hydroxytyrosol, 0.2% tyrosol and other polyphenols), and organic acids, proteins and minerals. To use this dried form as a starting material for this invention, it should be hydrated. The resulting juice is a preferred starting material.
- It has been found, in accordance with one aspect of this invention, that the polyphenol concentration of any type of olive juice can be increased by maintaining the olive juice at an elevated temperature and increasing the pH to at least 6.
- The elevated temperature can exist over a wide range, i.e. from about 20 degrees C. up to about 100 degrees C. The actual temperature is not especially critical, as long as it is under the boiling point of the olive juice. Preferred temperature ranges are from about 60 to about 80 degrees C., and a more preferred temperature is about 80 degrees C.
- Along with the increase in the temperature, the pH of the juice should be adjusted to a higher pH than is originally present in the untreated olive juice. The adjusted pH should be in a range of about 6 to about 11, with the preferred pH being from about 7 to about 10, and a more preferred range is from about 8 to about 9. A pH above about 10 can result in the degradation of the final HT, so it is not preferred. Any basic compound capable of adjusting pH can be used: preferred compounds are NaOH, KOH, and mixtures thereof. Generally, the amount needed will vary from batch to batch, but a typical amount needed will be approximately 10-15% by weight based on the weight of the batch.
- Under the conditions of the elevated temperature and pH-complex compounds which contain bound HT may break down, liberating HT. Thus, after the reactions are substantially complete, the juice will contain a higher amount of HT than the starting material. During the time that the reactions are taking place, the pH may change, and re-adjustment(s) may be required to maintain the desired pH. It is preferred to continually adjust the pH during the time of the reaction. One way of determining that the reactions are substantially complete is that the pH will remain relatively stable (i.e. relatively unchanged) for at least about ten minutes. The amount of time it will take for a batch to reach the point of stability for about 10 minutes can vary greatly depending on the individual composition to of the batch. Generally, as higher the temperature and the pH the less time the reaction will take.
- At this point, the partially processed olive juice no longer is bitter. Thus this invention also includes a process for removing the bitterness from an olive juice extract comprising raising the temperature and pH of the olive juice to the above-mentioned conditions. At this point, the olive juice may be process as desired, using any of the known process steps in the art, or, optionally steps presented below.
- The starting material for this step may be the de-bittered, HT enhanced juice made in accordance with the above description A, or it may be any starting material (such as those described in Section A as suitable as starting materials for the optional step described there. Generally concentrated juice is preferred for economic reasons, but the method will work with a variety of juices. Thus, the starting material may have solids, fats (oils) and/or fibers present in it.
- Typically unprocessed olive juice will contain a large amount of fine fibers. These are difficult to filter out as they tend to clog membrane filters, requiring a large amount of maintenance. It has been found, as another aspect of this invention, that fibers, residual oil and lipids, and/or other solids present in the olive juice can be agglomerated and then easily removed by a) adding a solvent in an amount (by volume) equal to about 40-400% of the olive juice or partially concentrated olive juice to form two phases; and then b) separating the two phases.
- The solvent which can be employed in this process can be any solvent or mixture of solvents which is water-miscible or nearly miscible like n-butanol. Alcohols, especially C1 to C4 (or mixtures thereof) are preferred, and ethanol is particularly preferred, especially when the end product is to be used in food or as part of a medicinal or nutritional supplement product. Other solvents which can also be utilized include: acetonitrile, acetone, and glycol.
- The amount of solvent is not especially critical, and will depend on the amount of water in the mixture. Usually the solvent will be needed in an amount that is at least equal to the amount of water present. For example, if ethanol is the solvent, for every 500 ml of water, about 600 ml of EtOH will be required. However, this is subject to a wide range: from about 40-400% solvent compared to the amount of water by weight, preferably 100-240%, and more preferably about 160-220% solvent compared to the amount of water. The important criteria is that enough solvent is added so that two distinct phases are formed.
- The temperature of this step is not particularly critical and may range from 0 degrees Celsius to about 80 degrees Celsius, or any temperature which is less than the boiling point of the mixture. Conveniently the temperature will be between about 20 and 60 degrees C., and most conveniently is room temperature, or about 25 degrees.
- At this point, two phases exist and any convenient means can be used to separate the two phases. The method of separation will depend on the actual make up of the material. For some batches, a filter can now be easily used, and/or a centrifuge. Other batches could be easily processed by simple decantation (if not too many solids were present, or if material is stuck to the wall of the vessel) or ordinary phase separation.
- In another embodiment of this invention, this same process can be used with a starting olive juice which has been processed to remove fibers, but which has undergone the de-bittering/HT concentrating step described in the previous section. Addition of the solvent and separation of the resultant phases will allow separation of any precipitates which may have formed during the debittering process.
- The solvent can be recovered for re-use, if desired, making the process more economical. Evaporation is generally the easiest way to so recover the solvent. At this point, is has been found in yet another aspect of the invention, that if one chooses to employ an evaporation step to recover the solvent, then adjusting the pH of the extract to below 6, preferably below 5, will prevent unwanted foaming during the evaporation process.
- At this point, the resulting non-bitter, solids-free olive juice extract, which forms another aspect of this invention can be used as is in any way desired. For example, it can be directly incorporated into a nutritional composition, for example a food or beverage composition. The food can be suitable for humans consumption, or can be an animal feed. Alternatively, it can be made into a nutritional supplement, for example, it can be formulated into capsules, tablets, or the like using known methods. Alternatively, the composition can be used in cosmetic compositions.
- In other embodiments of this invention, the non-bitter, solids-free extract is spray dried or free-dried using conventional techniques to form a powder derivative, and then incorporated into a final product. Optionally, stabilizers and the like amy be added to the juice prior to the drying step. The resulting powder can be directly incorporated into a nutritional composition, or it can be an animal feed. Alternatively, it can be made into a nutritional supplement; for examples it can be formulated into capsules, tablets, or the like using known methods. Alternatively, the composition can be used in cosmetic compositions.
- In other embodiments of this invention, the non-bitter, solids-free extract is subjected to additional processing steps, such as de-fatting, further extraction, or distillation of the HT. Such processes may be known techniques, or the techniques as further described in co-pending patent application U.S. application Ser. No. 12/647,032 filed on Feb. 18, 2010 may be used.
- The invention is now further illustrated in the following non-limiting examples.
- Unless otherwise stated, all % s given refer to weight percent.
- Starting material was HIDROX 6% (from CreAgri, Haywood, Calif. Its content is: (in Lot 6022406002. This is freeze-dried olive juice which has been stabilized with citric acid. weight %):
-
Carbohydrates Approx. 60% Lipids (olive oil) Approx. 15% Fibers Approx. 10% Hydroxytyrosol 2.1% Water Approx. 2% -
-
Solubility in water: a turbid, fine suspension Taste bitter Color beige-brown powder - 100 g HIDROX (CreAgri, from Example 1) 6% polyphenols, and 80 ml water were added to a reaction flask in a nitrogen atmosphere. The mixture was warmed up to 80° C. and adjusted to pH 9.0, followed by stirring for 30 minutes at 80° C. at pH 9.0 with continuous addition of a total of 38 ml sodium hydroxide 10 mol/l to maintain pH. The suspension was cooled to 60° C.
- The content of hydroxytyrosol increased by the base treatment to approx. 130%.
- The solids where precipitated at 60° C. by addition of 200 g ethanol. The mixture was cooled, stirred at ambient for 30 minutes and filtered by a Buchner funnel. The filtercake was washed with 50 g of ethanol 70%/water 30%.
- The filtrate was adjusted to pH 5 with approx. 5 ml hydrochloric acid 10 mol/l and evaporated at the rotavapor (20 mbar, 60° C.) to recover the ethanol, the non volatile residue 33.5 g.
- Content [w %]: 7.4% hydroxytyrosol, 0.8% tyrosol.
- Yield: 119% of the initial hydroxytyrosol
- The extract is not bitter at 1 mg/ml water
- In Table 1, below, “yield %” refers to the content of HT in the dried filtrate [w %]. Yield [w %] is based on the initial content of the starting material, HIDROX 6%.
-
TABLE 1 Ethanol Needed for the agglomerations of solids from hydrolyzed olive juice Agglomeration HT in filtrate pH with ethanol [m]* Filtration w % yield % 3.5 ~3 slow 4.2% 132% 5.0 ~2.3 rapid 7.2% 128% 6.5 ~1.1 rapid** 8.9% 126% 8.0 ~0.6 rapid** 8.1% 108% *Agglomeration was at ambient of a 50% solution of HIDROX (see Ex. 1) in water hydrolyzed at 80° C. pH = 9. pH was adjusted with conc. HCl at RT. [m] = amounts of ethanol: 50% solution.[w/w] Filterability and coagulation can be adjusted by the amount of ethanol (optimum different for each pH. The dried precipated mass contained 0.1-0.4% HT - 100 g HIDROX 6% polyphenols (CreAgri, Example 1) and 80 ml water were added to a reaction flask in an inert gas atmosphere. The mixture was warmed up to 60° C. under a nitrogen blanket and adjusted to pH6.0 followed by stirring for 30 minutes at 60° C. at pH 6.0 with continuous addition of a total of 36 ml sodium hydroxide 10 mol/l to maintain pH.
- The content of hydroxytyrosol increased by the base treatment to approx. 115%.
- The solids where precipitated at 60° C. by addition of 240 g ethanol. The mixture was cooled, stirred at ambient for 30 minutes and filtered by a Buchner funnel. The filtercake was washed with 50 ethanol 70%/water 30%
- The filtrate was evaporated at the rotavapor (20 mbar, 60° C.) to recover the ethanol. We recovered: 33.5 g residue. Content [w %]: 6.3% hydroxytyrosol, 0.7% tyrosol. The residue is slightly bitter at 1 mg/ml water
- The following samples where made in accordance with the above Examples
- 100 g HIDROX 6% (starting material, Example 1) was mixed with 100 g water to give a 50% solution. pH was adjusted to pH 9 at 80° C. with 10 m sodium hydroxyde. After approximately 30 minutes at 80° C., hydroxytyrosol which was in bound form is liberated, and the yield increases (theoretical yield is approx. 135%). With increasing pH, less ethanol is needed to agglomerate the particles, as described in the Table, below. Too little ethanol will not agglomerate the particles enough to precipitate efficiently to form a easily removable part. Higher amounts of ethanol results in a higher yield. The highest concentration of hydroxytyrosol in the filtrates resulted at a pH 8-9. For a 50% solution of olive juice, about the same amount of ethanol seems optimal.
-
Hydrolysis pH pH 3.5 pH 8.0 pH 8.0 pH 9.0 pH 9.0 temp 60° C. 80° C. 80° C. 80° C. 80° C. Agglomeration pH pH 8 pH 6.5 pH 8 pH 8 pH 8 Ethanol 120 g 188 g 210 g 165 g 215 g RT 60° C. 60° C. RT 60° C. Soluble 36.4 g 32.0 g 32.9 g 33.9 g 31.6 g Residue [g] HT [w %] 5.34% 7.17% 7.24% 7.22% 7.64% Yield [w %] 92.6% 109% 113% 117% 115% Bitterness at Bitter Sl. Not Not Not 1 mg/ml bitter bitter bitter bitter - 243 g of a commercially available olive juice extract which has been processed by the to provider to remove fibers (content=0.89% hydroxytyrosol) was concentrated in a vacuum to 190 g. In a reaction flask under an atmosphere of nitrogen, the concentrate was heated to 80° C. and pH was adjusted to 8.0, followed by stirring for 30 minutes at 80° C. at pH 8.0 with continuous addition of a total of 24 ml sodium hydroxide 10 mol/l to maintain pH.
- To the dark colored mixture was added 280 g ethanol to make the precipitate. The mixture was cooled and stirred at ambient for 1 h. The upper solution was decanted from the precipitate and evaporated at the rotavapor to recover the ethanol. The nonvolatile residue was 78 g. Content [w %]: 2.6% hydroxytyrosol, 0.6% tyrosol. Yield: 93% of the initial hydroxytyrosol. The residue is not bitter at 1 mg/ml water.
Claims (24)
1. A non-bitter hydroxytyrosol enriched olive juice extract produced by removing at least some of the solids present in an olive juice by a method consisting essentially of:
(a) adding a pH adjuster to the olive juice to obtain a pH of at least 6;
(b) adding to the olive juice at least one water-miscible or nearly water-miscible solvent selected from the group consisting of methanol, ethanol, propanol, butanol, acetonitrile, acetone and glycol in an amount equal to about 40-200% by volume of the olive juice to form two phases; and
(c) separating the two phases and recovering the phase containing an olive juice which has at least some of the solids removed.
2. The olive juice extract according to claim 1 , wherein the solvent is ethanol.
3. The olive juice extract according to claim 1 , wherein step (c) comprises at least one step selected from the group consisting of a filtering step, a centrifugation step, a decanting step, and a step of removing a layer of the two phases.
4. The olive juice extract according to claim 1 , wherein the method further consisting essentially of (d) recovering the solvent of step (b).
5. The olive juice extract according to claim 4 , wherein the step (d) is practiced by evaporating the solvent while maintaining a pH below 6.
6. The olive juice extract of claim 1 or 4 , wherein step (a) is practiced by maintaining the olive juice at an elevated temperature and increasing the pH to at least 6 by adding the pH adjuster until the polyphenol concentration of the olive juice is increased.
7. The olive juice extract according to claim 1 , wherein the solids present in olive juice are not fibres.
8. The olive juice extract according to claim 6 , wherein the elevated temperature is from about 20 degrees to 100 degrees C., and the pH is from about 6 to about 10.
9. The olive juice extract according to claim 8 , wherein the elevated temperature is maintained until the pH remains unchanged for at least about 10 minutes.
10. The olive juice extract according to claim 6 , wherein step (a) is practiced by adding NaOH, KOH or mixtures thereof as the pH adjuster to the olive juice.
11. The olive juice extract according to claim 9 , wherein the temperature is about 60-90° C. and the pH is about 7-9.
12. The olive juice extract of claim 1 , wherein the method further consisting essentially of (d) freeze drying or spray drying the olive juice.
13. The olive juice extract of claim 4 or 12 , wherein step (c) comprises at least one step selected from the group consisting of a filtering step, a centrifugation step, a decanting step, and a step of removing a layer of the two phases.
14. The olive juice extract of claim 12 , wherein step (a) is practiced by maintaining the olive juice at an elevated temperature and increasing the pH to at least 6 by adding the pH adjuster until the polyphenol concentration of the olive juice is increased.
15. The olive juice extract of claim 12 , wherein the solids present in the olive juice are not fibres.
16. The olive juice extract of claim 15 , wherein the elevated temperature is from about 20 degrees to 100 degrees C., and the pH is from about 6 to about 10.
17. The olive juice extract of claim 16 , wherein the elevated temperature is maintained until the pH remains unchanged for at least about 10 minutes.
18. The olive juice extract of claim 14 , wherein step (a) is practiced by adding NaOH, KOH or mixtures thereof as the pH adjuster to the olive juice.
19. The olive juice extract of claim 17 , wherein the temperature is about 60-90° C. and the pH is about 7-9.
20. The olive juice extract of claim 1 , comprising at least about 2-8% hydroxytyrosol, other olive polyphenols, and no solids.
21. The olive juice extract of claim 20 which is in powdered form.
22. A nutritional composition comprising the olive juice extract of claim 1 .
23. A feed composition comprising the olive juice extract of claim 1 .
24. A cosmetic composition comprising the olive juice extract of claim 1 .
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US13/480,442 US20120232163A1 (en) | 2007-08-21 | 2012-05-24 | Methods of making olive juice extracts containing reduced solids |
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EP07016344.9 | 2007-08-21 | ||
EP07016344 | 2007-08-21 | ||
PCT/EP2008/006790 WO2009024318A1 (en) | 2007-08-21 | 2008-08-19 | Methods of making olive juice extracts containing reduced solids |
US67404410A | 2010-02-18 | 2010-02-18 | |
US13/480,442 US20120232163A1 (en) | 2007-08-21 | 2012-05-24 | Methods of making olive juice extracts containing reduced solids |
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US67404410A Division | 2007-08-21 | 2010-02-18 |
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US13/480,442 Abandoned US20120232163A1 (en) | 2007-08-21 | 2012-05-24 | Methods of making olive juice extracts containing reduced solids |
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EP2027781A1 (en) * | 2007-08-21 | 2009-02-25 | DSMIP Assets B.V. | Method of removal of bitter taste from olive juice extract |
IT201600099539A1 (en) * | 2016-10-07 | 2018-04-07 | Linfa S C A R L | New product based on olives added with functional extracts from Olea Europea with 10% hydroxytyrosol and its derivatives |
CN106359943A (en) * | 2016-10-18 | 2017-02-01 | 杨继刚 | Feed additive capable of improving producing performance and foraging performance of early-weaned lamb |
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US6358542B2 (en) | 1999-12-20 | 2002-03-19 | Usana, Inc. | Antioxidant compositions extracted from olives and olive by-products |
US7713569B2 (en) | 2000-09-01 | 2010-05-11 | Creagri, Inc. | Hydroxytyrosol-rich composition from olive vegetation water and method of use thereof |
GB2415136A (en) * | 2004-06-17 | 2005-12-21 | Natraceutical Sa | Obtaining olive polyphenol concentrate from a by-product of olive oil extraction using membrane separation techniques |
JP2006219433A (en) * | 2005-02-10 | 2006-08-24 | Kanebo Cosmetics Inc | Agent for preventing ultraviolet hazard |
PT103326A (en) | 2005-07-27 | 2007-01-31 | Inst De Biolog Ex E Tecnologic | METHOD FOR OBTAINING A RICH NATURAL CONCENTRATE IN HYDROXYTANOLSOL FROM WASTE OF OLIVE OIL PRODUCTION USING CLEAN TECHNOLOGIES |
KR101351674B1 (en) * | 2005-09-30 | 2014-01-14 | 디에스엠 아이피 어셋츠 비.브이. | Novel compositions containing polyphenols |
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CN101784202A (en) | 2010-07-21 |
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