WO2010010219A1 - Aceite de orujo de oliva comestible concentrado en ácidos triterpénicos, procedimiento de refinación física utilizado para su obtención y recuperación de los componentes funcionales presentes en el aceite crudo - Google Patents
Aceite de orujo de oliva comestible concentrado en ácidos triterpénicos, procedimiento de refinación física utilizado para su obtención y recuperación de los componentes funcionales presentes en el aceite crudo Download PDFInfo
- Publication number
- WO2010010219A1 WO2010010219A1 PCT/ES2009/070298 ES2009070298W WO2010010219A1 WO 2010010219 A1 WO2010010219 A1 WO 2010010219A1 ES 2009070298 W ES2009070298 W ES 2009070298W WO 2010010219 A1 WO2010010219 A1 WO 2010010219A1
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- WIPO (PCT)
- Prior art keywords
- oil
- distillation
- mbar
- distillate
- pomace
- Prior art date
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- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B13/00—Recovery of fats, fatty oils or fatty acids from waste materials
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/02—Other edible oils or fats, e.g. shortenings, cooking oils characterised by the production or working-up
-
- 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
- A23K20/158—Fatty acids; Fats; Products containing oils or fats
-
- 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
- A23L33/115—Fatty acids or derivatives thereof; Fats or oils
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/001—Refining fats or fatty oils by a combination of two or more of the means hereafter
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/006—Refining fats or fatty oils by extraction
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/008—Refining fats or fatty oils by filtration, e.g. including ultra filtration, dialysis
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/02—Refining fats or fatty oils by chemical reaction
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/12—Refining fats or fatty oils by distillation
-
- 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
- Y02E50/10—Biofuels, e.g. bio-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
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W30/00—Technologies for solid waste management
- Y02W30/50—Reuse, recycling or recovery technologies
- Y02W30/74—Recovery of fats, fatty oils, fatty acids or other fatty substances, e.g. lanolin or waxes
Definitions
- the present invention is included within the food technology sector by describing a new physical refining process based on the neutralization of free fatty acids by successive distillations at high temperature and vacuum. Specifically, it describes the process of obtaining, from an olive pomace oil of centrifugation or decantation, of an edible oil with a high concentration of triterpenic acids with direct application as a constituent in the feed. Additionally, it is also the object of the invention to recover a concentrate rich in triterpenic acids, as well as other functional components present in the crude oil, from the by-products of the process and which can be destined to sectors as diverse as food, cosmetics, energy, as a source of compounds of interest for the chemical industry, and pharmaceutical, as medicinal and veterinary preparations.
- oil mills once the olives have undergone the primary process of extracting olive oil by mechanical means. It is composed mostly of solid waste from the pulp, skin and bone or seed of olives, oil retained in said solid waste (and that has not been extracted by conventional mechanical procedures) and water both constitution ( own of the olive) as added during the oil extraction process (Sánchez Moral y Ruiz Méndez, 2006).
- the traditional process to extract this oil and produce the so-called "crude pomace oil” is using hexane, light hydrocarbon from petroleum and immiscible with water. The process consists of two stages, an initial stage of drying the pomace to approximately 8% humidity and a subsequent stage of solvent extraction.
- pomace oils extracted following this traditional method have two clear drawbacks.
- the extracted oils have a greater amount of phospholipids, waxes and an important amount of anomalous compounds such as soaps and ethyl esters.
- the subsequent drying of the pomace must be carried out at very high temperatures and, due to the drastic conditions used, the crude pomace oil obtained, additionally, presents unusually high amounts of Polycyclic Aromatic Hydrocarbons (hereinafter HPAs) (400-200 ppb of benzo-alpha-pyrene) (León Camacho et al., 2003).
- HPAs Polycyclic Aromatic Hydrocarbons
- This oil commercially classified as “crude pomace oil”, stands out for presenting a minimum amount of HPAs, its formation does not take place because there is no drying stage, and phospholipids, because no solvents are used in its process of obtaining. Additionally, and in addition to significantly reducing the presence of these compounds, the main characteristic of olive pomace oil resulting from mechanical extraction is that it contains very high amounts of bioactive and functional compounds of great interest such as, for example, triterpenic acids .
- Triterpenic acids are natural compounds present in plants and in foods to which health beneficial properties are attributed and, therefore, are subject to demand by the food, cosmetic and pharmacological industries.
- beneficial properties attributed to triterpenic acids are its antimicrobial and anti-hyperglycemic activities (Horiuchi et al, 2007, Sato et al, 2007), anti-inflammatory and antitumor activities (Márquez-Mart ⁇ n et al., 2006, Braga et al.
- the triterpenic acids constituents of the skin of the olive, pass into the oil due to the hydrolytic processes that take place in the olive and in the pomace. Thus, no appreciable amounts of these acids are found in extra virgins, but in pomace oils and virgin olive oils with an acidity greater than 1% (Pérez Camino and Cert., 1999).
- concentration in triterpenic acids increases with the time of storage of the pomace, being able to reach concentrations greater than 15 g / kg after seven months and being, oleanolic and maslinic the two main identified triterpenic acids.
- the content of maslinic acid is greater than that of oleanolic acid in the pomace oil obtained by centrifugation (Garc ⁇ a et al., 2008).
- oils must be refined for use as edibles.
- the refining of oils is a process that aims at the elimination of undesirable compounds either because they communicate characteristics of color, smell and taste not pleasing to the consumer, or because they affect the stability of the product.
- These compounds can be natural in oils (such as phospholipids or free acidity), degradation compounds (peroxides) or reagents added during the process (soda, soils, etc.) (De Greyt and Kellens, 2000).
- the conventional process that is usually applied to olive pomace oil is the so-called chemical refining that consists of the following stages: degumming, neutralization, winterization, discoloration and deodorization (Antonopoulos et al., 2006).
- degumming has the objective of eliminating phospholipids by means of the addition of moisturizing agents.
- the degummed oil is treated with an alkaline solution to precipitate free fatty acids such as soaps and, at the same time, remove the remaining traces of phospholipids.
- Another advantage of the physical refining procedure presented is that it allows recovering high quality by-products.
- the initial filtration of the oil allows to separate the insoluble triterpenic acids in the oil and obtain a concentrate with more than 50% purity and on the other hand, the by-products from the different distillations of the physical refining process constitute, by themselves, a good raw material for obtaining compounds of high added value.
- these by-products during the process object of the patent in addition to the final olive pomace oil, concentrated in triterpenic acids, not only the Free fatty acids but also appreciable amounts of phytosterols, hydrocarbons and tocopherols, which have been the subject of intense research activity for several decades.
- the present invention is based on a new physical refining process where, using olive pomace oil obtained by centrifugation or decantation as the starting raw material, the decrease in free fatty acids is produced by controlled distillation stages avoiding the use of chemical compounds such as phosphoric acid and sodium hydroxide during the process.
- This allows the triterpenic acids of lower volatility to be maintained in the final oil, thus obtaining an oil suitable for consumption enriched in the triterpenic acids present in the initial pomace and, additionally, various fractions and concentrates enriched in triterpenic acids, methyl esters and Ethyl, sterols or squalene of enormous industrial and medical interest.
- a refining process is described that allows to obtain, for the first time, a refined olive pomace oil, rich in triterpenic acids typical of the oil and suitable for consumption.
- a physical refining process is presented that, using as a product the product obtained from filtering an olive pomace oil obtained by centrifugation or decantation, is based on the elimination of the free fatty acids present by distillation, in controlled stages, of filtered and discolored oil.
- the refining procedure presented allows the use of all the high added value by-products generated during the process.
- a first aspect of the present invention constitutes the filtration process, step a) of Figure 1, of an olive pomace oil obtained by centrifugation or decantation characterized in that the filtration of the starting raw olive pomace oil It is carried out through filters between 20-0.1 microns of light, at temperatures above ambient and below 70 ° C, preferably between 35-45 ° C.
- a second aspect of the invention constitutes the refining process to eliminate the free fatty acids present in the filtered olive pomace oil obtained in the previous stage that is carried out by successive controlled distillations, the degumming, neutralization steps not taking place. alkaline, washings and winterization established in the traditional chemical refining, with the purpose of maintaining triterpenic acids, of lower volatility, present in the final oil and comprising the following stages (Figure 1):
- b.- decolorization by adding the appropriate amount of technological adjuvants, preferably activated bleaching earth (0.5-2%), amorphous silica (trisyl) (0.1-0.5%) and active carbon (0.05 and 0.2%), of the oil filtering obtained in the previous stage (a).
- technological adjuvants preferably activated bleaching earth (0.5-2%), amorphous silica (trisyl) (0.1-0.5%) and active carbon (0.05 and 0.2%)
- the oil filtering obtained in the previous stage (a) the filtered starting oil is degassed and heated to the normal bleaching temperature, between 80 and 120 ° C.
- the necessary technological adjuvants are added while being kept under stirring for a maximum of 30 minutes under pressure conditions less than 70 mbar, preferably 40 mbar.
- a filtration process is carried out to remove the added technological adjuvants;
- a distillation of free fatty acids In a first distillation (d), the product discolored oil obtained in section (b) is subjected to a distillation at a temperature below 200 ° C and a vacuum below 10 mbar, in a thin layer type distiller with or without steam entrainment or nitrogen, obtaining as a byproduct a distillate [2] is obtained.
- a second distillation (c2) at a temperature below 250 ° C and vacuum below 5 mbar the residual free fatty acids in the oil resulting from the treatment (d) are removed, with the distillate [3] being additionally obtained,
- step (c) deodorization and stabilization of the oil obtained in step (c) by vacuum distillation of less than 3 mbar and at a low temperature, below 220 ° C, with steam entrainment, obtaining an oil [4] with a triterpenic acid content greater than 150 ppm suitable for consumption;
- a third aspect of the invention constitutes a solid-liquid extraction process, step f), with organic solvents, preferably hexane and ethanol, of the product retained in stage a) of filtration.
- a fourth aspect of the invention constitutes a concentrated extract.
- [1] characterized in that it is obtained by application of stages a) and f), and because it has a concentration of triterpenic acids greater than 20%, normally greater than 50%, and where the proportion of maslinic acid is greater than that of oleanolic acid .
- a fifth aspect of the invention constitutes a distillate [2] characterized in that it is obtained by application of steps a), b) and d), and because it has a concentration of free fatty acids greater than 60% and total ethyl esters greater than 10%
- a sixth aspect of the invention constitutes a distillate [3] characterized in that it is obtained by application of steps a), b), d) and c2), and because it has a concentration of free fatty acids greater than 30% and total ethyl esters greater than 5%.
- a seventh aspect of the invention constitutes a refined olive pomace oil [4] characterized in that it is obtained by application of steps a), b), d), c2) and d), and because it has a concentration of triterpenic acids, preferably maslinic and oleanolic, greater than 150 ppm.
- a seventh aspect of the invention constitutes a distillate [5] characterized in that it is obtained by application of steps a), b), d), c2) and e), and because it contains, at least, esters of fatty acids with linear alcohols Short chain, squalene and free fatty acids.
- An eighth aspect of the invention constitutes a concentrate [6] characterized in that it is obtained by application of steps a), b), d), c2) and e), and because it has an unsaponifiable content in excess of 15%, constituted mostly by sterols.
- the present invention faces the problem of offering a refined pomace oil suitable for consumption, which retains the maximum of the triterpenic acids present in the olive pomace oil obtained by centrifugation.
- This olive pomace oil rich in triterpenic acids is obtained through a physical refining process that avoids the use of chemical compounds such as phosphoric acid and sodium hydroxide during the process.
- the process presented in this patent begins with an initial filtration stage (a) of mechanically obtained olive pomace oil.
- Oil filtration is carried out sequentially through filters of 20 microns, 10 microns, 5 microns, 1 mill and 0.1 min, since the pomace oil obtained by centrifugation, it contains a significant amount of suspended solids and if the mesh is small initially, the filters collapse preventing the flow of oil, so filters are placed in series decreasing the size of the light in each one.
- the retained solids consist mostly of triterpenic acids insoluble in the oil due to their high concentration and low solubility.
- the filtration is carried out at temperatures above the ambient and below 70 ° C, to decrease the viscosity of the oil and increase its fluidity without solubilizing the triterpenic acids to be separated.
- the solid residue in a by-product rich in triterpenic acids and the filtrate is a transparent pomace oil that is subsequently subjected to the refining process that begins with a fading stage.
- bleaching earths alumino-magnesium silicates
- Polar substances such as soaps and phospholipids collapse the active centers of the earth and do not allow them to act effectively against chlorophylls and other chromophores compounds, which is why it is crucial that elimination is performed effectively using amorphous silicas such as Trisyl (Grace ) to achieve the objective of this stage and subsequent distillation stages.
- active carbon is also recommended to eliminate oxidized compounds responsible for the brown color present in the pomace oil, and pollutants such as polycyclic aromatic hydrocarbons.
- the treatment is carried out under vacuum less than 70 mbar, the usual procedure being as follows: the oil is degassed and heated to The working temperature, between 80 and 120 ° C. Next, the necessary technological adjuvants are added and a maximum of 30 minutes is maintained with stirring. Subsequently, the oil is filtered to remove the added adjuvants.
- the bleached oil obtained is subjected to distillation (c) whose objective is to eliminate free fatty acids from the oil, until its content is less than 0.5%.
- distillation takes advantage of the differences in volatility and boiling points of the liquid components to be separated and depends on variables such as temperature, pressure, composition of the mixture and liquid-vapor balance. If the operating pressure decreases, the volatility of the compounds increases and the boiling occurs at lower temperatures, which prevents thermolabile compounds from degrading.
- thin layer distillers are preferably used, very suitable for the elimination of free fatty acids, which are in this case the majority volatile compounds that are eliminated by the upper part of the column.
- distillations are carried out in several stages, varying the temperature as the composition of the boiling liquid varies. In this case, two distillation stages have been applied.
- the first distillation (d) allows obtaining a low acidity oil ( ⁇ 3% expressed as oleic acid) and a distillate [2] containing as main compounds free fatty acids, esters of fatty acids with short chain alcohols such as they are ethyl and methyl and have a low content of unsaponifiable matter, being susceptible to application in the field of oleochemistry and bio-energy.
- the distillation is carried out at a temperature below 200 ° C and vacuum below 10 mbar, in a thin layer type distiller obtaining an oil with acidity still greater than 0.5% (expressed as a percentage of oleic acid).
- the second distillation (c2) of the oil is intended to complete the separation of free fatty acids.
- the product obtained in section (d) is subjected to distillation at a temperature below 250 ° C and vacuum below 5 mbar in a thin layer type distiller, with or without steam or nitrogen entrainment.
- the process is completed with the classic deodorization stage of the refining process (d). It is a process of distillation under vacuum and at high temperature, which is carried out with water vapor drag, although the use of nitrogen is an alternative (Huesa and Dobarganes, 1990).
- the temperatures used for deodorization are between 180 ° C and 270 ° C. These temperature limits are established by the chemical reactions of decomposition and hydrolysis that occur during this stage (Sjoberg, 1991).
- the minimum time required normally depends on the degree of thermal discoloration that is desired.
- the amount of volatiles generated in this stage is less than 0.1% of the amount of oil subjected to the treatment.
- non-polar organic solvents are required that do not solubilize triterpenic acids, preferably hexane, to remove the oil occluded in the filters, mainly triglycerides and waxes, and then a polar solvent, preferably ethanol at 60 -80 ° C to solubilize and separate triterpenic acids.
- the clarification is carried out, by filtration or centrifugation, of the extracts and subsequently at the concentration of the clarified by evaporation under vacuum of the solvent, until a volume of the crude extract between 20% and 50% of the maceration volume is achieved. initial.
- the extract can also be dried under vacuum until it is obtained as a powder.
- step (c2) From the distillate [3] obtained in step (c2) and by means of a third distillation the most volatile fraction [5] and a concentrate in matter is obtained unsaponifiable [6].
- a high vacuum short path distillation (0.1-0.001 mbar), or a molecular distillation is used, with working temperatures below 215 ° C, obtaining fractions that are enriched in certain bioactive compounds.
- the operating conditions are adjusted according to the quality of the distillate [3] obtained.
- distillate [5] The most volatile fraction, called distillate [5], is characterized by a fatty acid esters content with linear short chain alcohols, squalene and free fatty acids, in varying proportions.
- concentrate [6] the less volatile fraction, called concentrate [6]
- concentrate [6] has an unsaponifiable content in excess of 15%, consisting mainly of squalene and sterols, and has great industrial potential, with immediate application in human and animal feed, as well as in Pharmacology and cosmetics, either in its integral form, or concentrated or diluted in its entirety or fractions, or eliminating fractions, which will be the subject of claims in the formulation of the patent.
- Stage 1.- Obtaining olive pomace oil with a high content of triterpenic acids suitable for consumption.
- the bleached oil was subjected to a first distillation of fatty acid esters with short chain alcohols and free fatty acids, at a temperature of less than 190 ° C and vacuum of 4.5 mbar in a thin layer distiller without steam or nitrogen entrainment. An oil with 2.6% oleic acid and a distillate [2] was obtained.
- the process of obtaining the triterpenic acid concentrate was carried out using a 2kg sohxlet extractor with a capacity of the solid container and a 20 I capacity of the liquid flask for solid-liquid extraction.
- the cellulose filters of 10 microns, 5 microns, 1 micron and 0.1 microns were introduced into the solids container and were first subjected to a hexane extraction of the non-polar compounds, for 4 hours.
- the extract obtained dragged insoluble compounds in hexane through which clarification was then carried out, by filtration or centrifugation of the extract, and a solid was obtained that binds to the concentrate obtained in the next step
- the compounds retained in the filters were extracted with ethanol for 8 hours and the extract obtained was subjected to vacuum drying until a powder concentrate was obtained.
- a concentrate [1] was obtained with 60% terpenic acids, 40% corresponding to maslinic acid and 20% oleanolic acid.
- the distillates obtained were characterized by their high content in non-glyceride esters of fatty acids with short chain alcohols such as ethyl and methyl greater than 10% and a free fatty acid content close to 50%.
- the Distilled fraction [2] is mainly composed of free fatty acids (73.33%), and esters of fatty acids with short chain alcohols (16.85%), and a small proportion of Unsponsable matter (0.88%) .
- distillate [3] From the distillate [3] the most volatile fraction, distillate [5], and a less volatile fraction, concentrated in unsaponifiable matter [6], were obtained.
- a distillation was used in a short path of high vacuum (0.01 mbar) at 210 ° C, obtaining two fractions that are enriched in certain active ingredients (Table 4).
- the unsaponifiable fraction present in the most volatile fraction is constituted essentially by squalene while the less volatile is enriched in sterols.
- TGR5 agonist isolated from Olea europaea. Biochem Biophys Res. Commun. 2007, 362, 793-798.
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- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Microbiology (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Nutrition Science (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Mycology (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
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Abstract
Description
Claims
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES09800097.9T ES2687774T3 (es) | 2008-07-22 | 2009-07-21 | Procedimiento de refinación física utilizado para la obtención de aceite de orujo de oliva comestible concentrado en ácidos triterpénicos y recuperación de los componentes funcionales presentes en el aceite crudo |
US13/055,167 US8361518B2 (en) | 2008-07-22 | 2009-07-21 | Edible olive pomace oil concentrated in triterpenic acids, procedure of physical refining utilised for obtainment thereof and recovery of functional components present in the crude oil |
EP09800097.9A EP2305783B1 (en) | 2008-07-22 | 2009-07-21 | Procedure of physical refining utilised for obtainment of edible olive pomace oil concentrated in triterpenic acids and recovery of functional components present in the crude oil |
CA2731917A CA2731917C (en) | 2008-07-22 | 2009-07-21 | Edible olive pomace oil concentrated in triterpenic acids, physical refining process used for obtainment thereof and recovery of functional components present in the crude oil |
JP2011519199A JP5512671B2 (ja) | 2008-07-22 | 2009-07-21 | トリテルペン酸を豊富に含む食用オリーブポマースオイル、該オイルを取得するために使用される物理的精製プロセス、および粗製オイル内に存在する機能成分の回収 |
MX2011000786A MX2011000786A (es) | 2008-07-22 | 2009-07-21 | Aceite de orujo de oliva comestible concentrado en acidos triterpenicos, procedimiento de refinacion fisica utilizando para su obtencion y recuperacion de los componentes funcionales presentes en el aceite crudo. |
NZ590649A NZ590649A (en) | 2008-07-22 | 2009-07-21 | Edible olive pomace oil concentrated in triterpenic acids, procedure of physical refining utilised for obtainment thereof and recovery of functional components present in the crude oil |
AU2009273171A AU2009273171B2 (en) | 2008-07-22 | 2009-07-21 | Edible olive pomace oil concentrated in triterpenic acids, procedure of physical refining utilised for obtainment thereof and recovery of functional components present in the crude oil |
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Application Number | Priority Date | Filing Date | Title |
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ESP200802178 | 2008-07-22 | ||
ES200802178A ES2332977B1 (es) | 2008-07-22 | 2008-07-22 | Aceite de orujo de oliva comestible concentrado en acidos triterpenicos, procedimiento de refinacion fisica utilizado para su obtencion y recuperacion de los componentes funcionales presentes en el aceite crudo. |
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WO2010010219A1 true WO2010010219A1 (es) | 2010-01-28 |
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PCT/ES2009/070298 WO2010010219A1 (es) | 2008-07-22 | 2009-07-21 | Aceite de orujo de oliva comestible concentrado en ácidos triterpénicos, procedimiento de refinación física utilizado para su obtención y recuperación de los componentes funcionales presentes en el aceite crudo |
Country Status (9)
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US (1) | US8361518B2 (es) |
EP (1) | EP2305783B1 (es) |
JP (1) | JP5512671B2 (es) |
AU (1) | AU2009273171B2 (es) |
CA (1) | CA2731917C (es) |
ES (2) | ES2332977B1 (es) |
MX (1) | MX2011000786A (es) |
NZ (1) | NZ590649A (es) |
WO (1) | WO2010010219A1 (es) |
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US10334870B2 (en) | 2010-10-07 | 2019-07-02 | Tropicana Products, Inc. | Processing of whole fruits and vegetables, processing of side-stream ingredients of fruits and vegetables, and use of the processed fruits and vegetables in beverage and food products |
US10667546B2 (en) | 2013-02-15 | 2020-06-02 | Pepsico, Inc. | Preparation and incorporation of co-products into beverages to enhance nutrition and sensory attributes |
WO2022035593A1 (en) * | 2020-08-11 | 2022-02-17 | Cargill, Incorporated | Removal of unwanted mineral oil hydrocarbons |
WO2022035595A1 (en) * | 2020-08-11 | 2022-02-17 | Cargill, Incorporated | Removal of unwanted mineral oil hydrocarbons |
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US10667546B2 (en) | 2013-02-15 | 2020-06-02 | Pepsico, Inc. | Preparation and incorporation of co-products into beverages to enhance nutrition and sensory attributes |
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EP2305783A1 (en) | 2011-04-06 |
JP5512671B2 (ja) | 2014-06-04 |
AU2009273171A1 (en) | 2010-01-28 |
EP2305783A4 (en) | 2013-08-07 |
US8361518B2 (en) | 2013-01-29 |
NZ590649A (en) | 2012-11-30 |
JP2011528748A (ja) | 2011-11-24 |
CA2731917C (en) | 2017-03-28 |
MX2011000786A (es) | 2011-07-29 |
CA2731917A1 (en) | 2010-01-28 |
AU2009273171B2 (en) | 2015-08-13 |
EP2305783B1 (en) | 2018-06-20 |
ES2687774T3 (es) | 2018-10-29 |
ES2332977B1 (es) | 2011-02-09 |
US20110189320A1 (en) | 2011-08-04 |
ES2332977A1 (es) | 2010-02-15 |
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