Classifications

• • 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
  • C11B3/12—Refining fats or fatty oils by distillation
  • C11B3/14—Refining fats or fatty oils by distillation with the use of indifferent gases or vapours, e.g. steam
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
  • A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
  • A23D9/02—Other edible oils or fats, e.g. shortenings or cooking oils characterised by the production or working-up
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
  • A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
  • A23D9/02—Other edible oils or fats, e.g. shortenings or cooking oils characterised by the production or working-up
  • A23D9/04—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
  • A23K—FODDER
  • A23K50/00—Feeding-stuffs specially adapted for particular animals
  • A23K50/40—Feeding-stuffs specially adapted for particular animals for carnivorous animals, e.g. cats or dogs
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23K—FODDER
  • A23K50/00—Feeding-stuffs specially adapted for particular animals
  • A23K50/40—Feeding-stuffs specially adapted for particular animals for carnivorous animals, e.g. cats or dogs
  • A23K50/42—Dry feed
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
  • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
  • A23L29/03—Organic compounds
  • A23L29/035—Organic compounds containing oxygen as heteroatom
  • A23L29/04—Fatty acids or derivatives
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
  • 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
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
  • A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
  • A23L5/20—Removal of unwanted matter, e.g. deodorisation or detoxification
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
  • B01D—SEPARATION
  • B01D1/00—Evaporating
  • B01D1/06—Evaporators with vertical tubes
  • B01D1/08—Evaporators with vertical tubes with short tubes
• • 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
  • C11B3/12—Refining fats or fatty oils by distillation
• • 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

Definitions

• the present invention relates to a pet food and a human food of improved palatability whereas such food contains polyunsaturated fatty acids.
• the present invention relates to a method for manufacturing the above food ingredient.
• Makers of animal food have a business incentive to produce food which meet the following three criteria: high in nutritional value, high in palatability and low in production cost.
• PUFAs polyunsaturated fatty acids
• omega-3 fatty acids are biologically important molecules which affect cellular physiology due to their presence in cell membrane, regulate production of gene expression of biologically active compounds, and serve as biosynthetic substrates.
• DHA docosahexaenoic acid
• omega-3 fatty acids cannot be synthesized de novo by land animals, these fatty acids must be obtained from nutritional sources.
• Polyunsaturated fatty acids are synthesized by microbes such as microalgae and fungi. Fish acquires polyunsaturated fatty acids by feeding on such microbes. Commercially, polyunsaturated fatty acids are obtained by extraction from fish, as well as by harvesting from microalgae or fungi via fermentation and extraction. Many chemicals are used in the process of extracting PUFA oil in order to expedite the extraction process via chemical reactions. Volatile byproducts are generated during such reaction. Many volatile byproducts, such as lipid oxidation products and Maillard reaction products, are produced in the extraction process.
• Crude oil When PUFA oil is initially extracted from fish or microalgae without any further refinement, it is called crude oil. Crude oil has offensive smell and taste, and thus is not well received and even rejected by human and animals.
• Crude oil needs to be purified before it is made ready for human consumption.
• the purification process involves the steps of refinement, bleaching, winterization, and deodorization.
• refinement involves removal of free fatty acids, phospholipids, oil soluble material, trace metal, and water-soluble molecules.
• Bleaching removes pigments, secondary oxidation products, trace metals, vitamins, environmental pollutants, and other polar
• Winterization is the name given to the process of removing sediments that will appear in oils at low temperature.
• Deodorization refers to the removal of volatile components, secondary oxidation products, free fatty acids, mono- and diglycerides, aldehydes, ketones, chlorinated hydrocarbons, pigments, and persistent organic pollutants.
• the above process is also referred to as RBWD process by the initial letter of the four steps.
• U.S. Patent Application No. 12/442,828 discloses an algal biomeal-based palatability enhancer which was claimed to be able to improve the texture and flavor of pet food.
• U.S. Patent Application No. 15/038545 discloses a method of preparing a palatability enhancer by including appropriate fat sources and edible agents in the food.
• the goal for this invention is to find a method for making a PUFA oil that is high in palatability, but low in cost to produce.
• the present invention is directed to a method for enhancing the palatability of a polyunsaturated fatty acids (PUFA) oil to a companion animal, wherein said method comprises the steps of: a) obtaining a crude PUFA oil; b) optionally, degumming, or refining by using a short path evaporator (SPE), or both degumming and refining by using a SPE said PUFA oil from step a); and c) deodorizing the PUFA oil from step b); wherein the yield of the PUFA oil after step c) is no less than 85% of the amount of the crude oil started with at step a), wherein said palatability is measured by animal food preference test, and wherein the palatability score of the PUFA oil obtained after step c) is at least 10 percentage points higher than the crude oil started with at step a).
• SPE short path evaporator
• the yield of the PUFA oil is no less than 90% of the crude oil started with at step a).
• the above animal food preference test is a two-bowl test.
• the palatability score of the PUFA oil obtained after step c) is at least 20, at least 30, at least 40, or at least 45 percentage points higher than the crude oil started with at step a).
• the deodorization step c) is conducted by using a VTA deodorizer or a DeSmet deodorizer.
• the PUFA oil is derived from fish, microorganism, or plants.
• the microorganisms are algae.
• the algae are Schizochytrium, Aurantiochytrium, or Thraustochytrium .
• the PUFA oil comprises one or more compounds of DHA
• the present invention is also directed to a polyunsaturated fatty acid (PUFA) oil, wherein said PUFA oil comprise less than 10 ppb of one or more Maillard reaction compounds and more than 1.5 ppb of one or more lipid oxidation products, when qualified as ethyl heptanoate.
• PUFA polyunsaturated fatty acid
• the PUFA oil comprise less than 1 ppb, less than 0.5 ppb, or less than 0.3 ppb Maillard reaction compounds when qualified as ethyl heptanoate.
• the amount of Maillard reaction compounds in said PUFA oil is undetectable when qualified as ethyl heptanoate.
• Maillard reaction compounds are selected from a group consisting of: trimethylpyrazine, 2-ethyl-3,5-dimethylpyrazine, 2-ethyl-3,6-dimethylpyrazine, tetramethyl pyrazine, 2-hydroxy-3-methyl-2-cyclopenten-l-one, methyl- lH-pyrrole-2- carboxaldehyde, and indole.
• the lipid oxidation products are selected from a group consisting of: l-penten-3-one, 4-heptenal, and 2,6-nonadienal.
• the present invention is also directed to a food composition for companion animals comprising a PUFA oil which is produced by the method of described above.
• the present invention is also directed to a food composition for a companion animal, wherein said food composition comprises the PUFA oil which comprise less than 10 ppb of one or more Maillard reaction compounds and more than 1.5 ppb of one or more lipid oxidation products, when qualified as ethyl heptanoate.
• the companion animal mentioned above is a dog or a cat.
• the above-mentioned food composition is a dog food, a cat food, a dog treat, or a cat treat.
• the food composition is a nutritional supplement.
• the present invention is also directed to a food composition for human consumption comprising a PUFA oil which is produced by the method of described above.
• the present invention is also directed to a food composition for human consumption, wherein said food composition comprises the PUFA oil which comprise less than 10 ppb of one or more Maillard reaction compounds and more than 1.5 ppb of one or more lipid oxidation products, when qualified as ethyl heptanoate.
• the present invention is further directed to a method for increasing the yield of a polyunsaturated fatty acids (PUFA) oil over a control oil which is the same oil but has been refined, bleached, winterized and deodorized (RBWD oil), wherein said method comprises the steps of: a) obtaining a crude PUFA oil; b) optionally, degumming said PUFA oil, or refining by using a short path evaporator (SPE) said PUFA oil, or both degumming and refining by using a SPE said PUFA oil from step a); and c) deodorizing the PUFA oil from step b); wherein the yield of the PUFA oil after step c) is more than 5 percentage points higher than the yield of the RBWD oil.
• the yield of the PUFA oil after step c) is more than 10 or more than 20 percentage points higher than the yield of the RBWD oil.
• the difference between the palatability scores of the PUFA oil after step c) and the RBWD oil is less than 10% in an animal food preference test in which a common control sample oil is used.
• the PUFA oil after step c) has a higher palatability score than the RBWD oil in an animal preference test in which a common control sample oil is used.
• the animal food preference test is a two-bowl test.
• the deodorization step c) is conducted by using a VTA deodorizer or a DeSmet deodorizer.
• the PUFA oil is derived from fish, microorganism, or plants.
• the microorganisms are algae.
• the algae are Schizochytrium, Aurantiochytrium, or Thraustochytrium .
• the PUFA oil comprises one or more compounds of DHA
• Fig. 1 is a graph showing human sensory result of algal PUFA oil samples, where the aroma score of the deodorized and undeodorized algal oils and the palatability score of the same oils are shown.
• Crude microbial PUFA oil and crude fish oil are rich in polyunsaturated fatty acids, especially omega-3 polyunsaturated fatty acids, such as DHA and EPA. It is widely recognized that omega-3 polyunsaturated fatty acids, especially DHA and EPA, are essential nutrients to animals. Mammals such as human and pets have to obtain omega-3 polyunsaturated fatty acids from external sources because they cannot synthesize such nutrients internally.
• the unprocessed crude microbial PUFA oil and crude fish oil have strong offensive odor and taste which need to be removed before becoming suitable for human and pet consumption.
• the refining process is complex and involves at least four steps including refinement, bleaching, winterization, and deodorization, and thus is very costly and low in yield. This makes it economically challenging to produce pet food which contains enough PUFAs while remains competitive in price. As a result, few pets have access to diet which is rich in beneficial nutrients such as PUFAs.
• deodorization is the most effective step in enhancing the palatability of the PUFA oil to a companion animal. It is further found that by adding either a degumming step or a refinement step, the palatability of the PUFA oil is further increased without much loss of yield in oil production. Thus, a palatable PUFA oil can be produced at a low cost by treating crude PUFA oil with a deodorizing step and optionally an additional degumming step or an additional refinement step, or both.
• the change of palatability is measured by an animal food preference test.
• the animal food preference test used in this invention is a two-bowl test.
• the two-bowl test (or paired stimulus or versus test) compares how much of two foods, presented simultaneously, is eaten in a defined period of time. This is a common test used in expert panels for dog and cat palatability assessment studies.
• two pet food samples, each containing a different PUFA oil are compared against each other.
• the first food contains a control PUFA oil.
• the second food contains a testing PUFA oil.
• the control PUFA oil can be any PUFA oil samples, either a crude oil or a processed oil.
• a commonly used control PUFA oil in this invention is a commercially available fish oil which has been treated by refining, bleaching, and deodorization steps.
• the control PUFA oil is a commercially available fish oil which has been treated by refining, bleaching, wintering and deodorization steps.
• the testing PUFA oil is a sample PUFA oil whose palatability is measured against the control PUFA oil.
• Such testing PUFA oil may be an unprocessed crude algal oil, or an algal oil which has been processed by one or more steps of degumming, short path evaporation, refining, bleaching, wintering, and deodorization.
• the palatability of a testing PUFA oil is considered as being improved over the other PUFA oil which it is paired with in a two-bowl test when the palatability score of the testing PUFA oil is above 50%. It means that the testing PUFA oil is preferred by the
• the two-bowl test and its scoring method are described in detail in Example 2 of this application.
• the two-bowl test is a type of animal food preference test, and it provides a quantitatively measurement of the food preference by an animal.
• the sum of the palatability score of the two sample being compared is always 100%. For example, if the palatability score of a testing PUFA oil is 56%, the palatability score of the other PUFA oil is 44%.
• test PUFA oil When several different testing PUFA oils are measured against the same PUFA oil, which in this case is called control PUFA oil or simply control oil, the relative preferences among the testing PUFA oil samples can be observed. For example, if the palatability score of testing PUFA oil samples A, B and C are 56%, 64% and 74%, respectively and all over a control oil, it can be concluded that sample C is the most palatable among the three samples. In this case, the identity of the control oil becomes irrelevant. This method is used in this invention to evaluate the effect of different processing steps on palatability improvement.
• the palatability of a first testing PUFA oil is considered as being significantly improved over a second testing PUFA oil when the palatability score of the first testing PUFA oil is 20 percentage points or higher than the second PUFA oil. For example, if the palatability score of a testing PUFA oil which has been refined, bleached and winterized is 46%, and another testing PUFA oil which has been refined, bleached, winterized, and deodorized is 74%, the palatability of the testing PUFA oil is considered having been significantly improved by the additional odorization step because the increment of palatability score is 38%.
• the yield of PUFA oil is defined as the percentage of PUFA oil which remains after one or several processing steps over the amount at the start of the process. Because each of the processing steps will remove some amount of the oil along with the impurities which it is designed to remove, it is generally expected that the yield of PUFA oil will decrease as more processing steps are added to the purification process.
• the deodorization step is far more effective in enhancing the palatability of a PUFA oil to a companion animal than any one of the refining, bleaching, winterization steps or even the three steps combined. It is further surprising to find that by adding either a degumming step or a refining step, or both steps, a high yield of 90% or more of the crude oil is attained after these processing steps. The resulting oil has an increased palatability of at least 45 percentage points higher than the palatability score of the crude oil. A common control oil sample is used in measuring the palatability score of the processed oil and the crude oil.
• the present invention is directed to a method for enhancing the palatability of a polyunsaturated fatty acids (PUFA) oil to a companion animal, wherein said method comprises the steps of: a) obtaining a crude PUFA oil; b) optionally, 1, or refining, or both degumming and refining said PUFA oil from step a); c) deodorizing the PUFA oil from step b); wherein the yield of the PUFA oil after step c) is no less than 85% of the amount of the crude oil started with at step a), wherein said palatability is measured by animal food preference test, and wherein the palatability score of the PUFA oil obtained after step c) is at least 10 percentage points or higher than the PUFA oil obtained after step c).
• PUFA polyunsaturated fatty acids
• the yield of the PUFA oil is no less than 80%, no less than 81%, no less than 82%, no less than 83%, no less than 84%, no less than 85%, no less than 86%, no less than 87%, no less than 88%, no less than 89%, no less than 90%, no less than 91%, no less than 92%, no less than 93%, no less than 94%, or no less than 95% when comparing the amount of PUFA oil obtained after step c) with the amount of the crude oil started with at step a).
• the yield of the PUFA oil is between 85% and 99%, between 85% and 95%, between 87% and 93%, between 90% and 95%, and between 92% and 95%, when comparing the amount of PUFA oil obtained after step c) with the amount of the crude oil started with at step a).
• the increase of palatability score of the PUFA oil at the above level of yield is at least 10 percentage points higher, at least 15 percentage points higher, at least 25 percentage points higher, at least 30 percentage points higher, at least 35 percentage points higher, at least 40 percentage points higher, at least 45 percentage points higher, at least 50 percentage points higher, at least 55 percentage points higher, at least 60 percentage points higher, or at least 65 percentage points higher than the palatability score of the crude oil before processing.
• the increase of palatability score of the PUFA oil at the above level of yield is between 20% and 65%, between 30% and 65%, between 40% and 65%, between 20% and 65%, between 30% and 50%, between 40% and 50%, between 30% and 60%, between 40% and 60%, between 20% and 30%, between 10% and 20%, or between 30% and 40% percentage points higher than the palatability score of the crude oil before processing.
• the yield of the resulting oil is more than 20 percentage points higher than the RBDW oil.
• the resulting oil also has an increased palatability of at least 10 percentage point higher than the palatability score of the RBWD oil.
• a common control oil sample is used in measuring the palatability score of the deodorized oil and the RBWD oil.
• the invention is directed to a method for increasing the yield of a polyunsaturated fatty acids (PUFA) oil over a control oil which is the same oil that has been refined, bleached, winterized and deodorized (RBWD oil), wherein said method comprises the steps of: a) obtaining a crude PUFA oil; b) optionally, degumming, or refining, or both degumming and refining said PUFA oil; c) deodorizing the PUFA oil from step b); wherein the yield of the PUFA oil after step c) is more than 30 percentage points higher than the yield of the RBWD oil.
• PUFA polyunsaturated fatty acids
• the yield of the RBWD oil is calculated as the percentage ratio between the amount of oil which remains after the crude oil at step a) is processed by refined, bleached, winterized and deodorized steeps and the amount of the crude oil at step a).
• the yield of the PUFA oil after step c) is more than 25 percentage points higher, more than 20 percentage points higher, more than 19 percentage points higher, more than 18 percentage points higher, more than 15 percentage points higher, more than 13 percentage points higher, or more than 10 percentage points, more than 5 percentage points higher than the yield of the RBWD oil.
• the palatability score of the above oil after step c) and the control oil are the same.
• the palatability score of the above oil and the control oil has a difference of no more than 10%.
• the difference of palatability score is no more than 9%, no more than 8%, no more than 7%, no more than 6%, no more than 5%, no more than 4%, no more than 3%, no more than 2%, or no more than 1%.
• the difference of palatability score is between 1% and 10%, between 2% to 10%, between 3% and 10%, between 4% and 10%, between 5% and 10%, between 6% and 10%, between 7% and 10%, and between 4% and 7%.
• the PUFA oil after step c) has a higher palatability score than the RBWD oil in an animal preference test in which a common control sample oil is used. In another embodiment, the PUFA oil after step c) has between 1 and 10, between 5 and 10, or between 7 to 10 percentage points higher palatability score than the RBWD oil in an animal preference test in which a common control sample oil is used. In another embodiment, the PUFA oil after step c) has a higher palatability score of between 1% and 10%, between 2% to 10%, between 3% and 10%, between 4% and 10%, between 5% and 10%, between 6% and 10%, between 7% and 10%, and between 4% and 7% than that of the RBWD oil.
• the above objectives are accomplished by a method of enhancing the palatability of a PUFA oil comprising the step of treating said oil with a deodorizer.
• the deodorizer is a VTA deodorizer.
• the deodorizer is a DeSmet deodorizer.
• the above method further comprises a degumming step and/or a short path evaporation step.
• the method does not comprise any refinement, bleaching or winterizing step, and thus significantly increases the yield of PUFA oil in the process and reduces the cost of production.
• the degumming step and the SPE step cause little oil yield loss.
• the refinement, bleach and winterization steps cause significant yield loss.
• the steps of degumming and refining are optional because the application of these steps will depend on the quality of the crude oil which is being processed. If the starting crude PUFA oil contains little free fatty acids, the refining step may be omitted. Similarly, if the starting crude oil contains little phospholipids or other impurities and thus the oil is unlikely to clog the deodorizer, the degumming step may be omitted too.
• volatiles produced during the process of extracting PUFA oil from its source generally cause off-odor(s) and flavor(s).
• off- odor causing volatiles include but are not limited to lipid oxidation products such as l-penten-3- one, 4-heptenal, 2,6-nonadienal, and Maillard reaction compounds such as trimethylpyrazine, 2- ethyl-3,5-dimethylpyrazine, 2-ethyl-3,6-dimethylpyrazine, tetramethyl pyrazine, 2-hydroxy-3- methyl-2-cyclopenten-l-one, tethyl-lH-pyrrole-2-carboxaldehyde, and indole.
• a crude PUFA oil is treated to remove all or substantially all
• Maillard reaction compounds wherein the resulting oil has a significantly higher palatability score than the crude PUFA oil.
• the above Maillard reaction compounds was narrowed down to the following list: trimethylpyrazine, 2-ethyl-3,5-dimethylpyrazine, 2-ethyl- 3,6-dimethylpyrazine, tetramethyl pyrazine, 2-hydroxy-3-methyl-2-cyclopenten-l-one, methyl- lH-pyrrole-2-carboxaldehyde, and indole. It is found in the present invention that the removal of the above seven compounds from a crude alga oil or a crude fish oil can significant increase the palatability of such oil to companion animals.
• lipid oxidation products in the PUFA oil does not significantly impact the palatability of the oil.
• lipid oxidation products include but are not limited to: l-penten-3-one, 4- heptenal, and 2,6-nonadienal.
• the palatability of PUFA oil is significantly improved by removing Maillard reaction compounds from crude PUFA oil to a none-detectable level.
• the method for detecting Maillard reaction compounds and lipid oxidation products is a SPME-GCMS analysis method.
• the palatability of PUFA oil to human and pet is significantly improved by reducing the level of Maillard reaction compounds in the PUFA oil to less than 10 ppb of Maillard reaction compounds when qualified as ethyl heptanoate.
• the palatability of PUFA oil to human and pet is significantly improved by reducing the level of Maillard reaction compounds in the PUFA oil to less than 10 ppb of Maillard reaction compounds when qualified as ethyl heptanoate, whereas the lipid oxidation products in the PUFA oil is at a level of more than 1.5 ppb when qualified as ethyl heptanoate.
• the palatability of PUFA oil to human and pet is significantly improved by reducing the level of Maillard reaction compounds in the crude oil to less than 1 ppb of Maillard reaction compounds when qualified as ethyl heptanoate.
• the palatability of PUFA oil to human and pet is significantly improved by reducing the level of Maillard reaction compounds in the crude oil to less than 0.5 ppb of Maillard reaction compounds when qualified as ethyl heptanoate. In another embodiment, the palatability of PUFA oil to human and pet is significantly improved by reducing the level of Maillard reaction compounds in the crude oil to less than 0.3 ppb of Maillard reaction compounds when qualified as ethyl heptanoate.
• the palatability of PUFA oil to human and pet is significantly improved by reducing the level of Maillard reaction compounds in the crude oil to less than 500, less than 200, less than 100, less than 50, less than 20, less than 5, less than 2, less than 0.2, less than 0.1 ppb when qualified as ethyl heptanoate.
• the palatability of PUFA oil to human and pet is significantly improved by reducing the level of Maillard reaction compounds in the crude oil to between 500 and 0.1 ppb, between 200 and 0.1, between 200 and 0.1, between 100 and 0.1, between 50 and 0.1, between 10 and 0.1, between 2 and 0.1, between 1 and 0.1, and between 20 and 1, and between 10 and 1 when qualified as ethyl heptanoate.
• the numerical value of the level of Maillard reaction compounds and lipid oxidation products which is referred to in this application (in the unit of ppb) is the total amount of Maillard reaction compounds and lipid oxidation products detected in the PUFA oil, unless it is specifically referred to as the level of an individual Maillard reaction compound and lipid oxidation product.
• the palatability of PUFA oil to a human and a pet animal is significantly improved by reducing the level of Maillard reaction compounds in the PUFA oil to less than 10 ppb of Maillard reaction compounds, whereas the PUFA oil comprises more than 1.5 ppb of one or more lipid oxidation products, when qualified as ethyl heptanoate.
• the lipid oxidation products are selected from a group consisting of: l-penten-3- one, 4-heptenal, and 2,6-nonadienal.
• the lipid oxidation products in the PUFA oil is at a level of more than 1 ppb, more than 2 ppb, more than 3 ppb, more than 4 ppb, or more than 5 ppb, more than 20 ppb, more than 50 ppb, or more than 100 ppb, when qualified as ethyl heptanoate. In other embodiments, the lipid oxidation products in the PUFA oil is at a level of between 100 and 1 ppb, between 50 and 1 ppb, between 20 and 1 ppb, and between 15 and 1 ppb, when qualified as ethyl heptanoate.
• the level of Maillard reaction compounds in the crude oil is less than 500, less than 200, less than 100, less than 50, less than 20, less than 5, less than 2, less than 0.2, less than 0.1 ppb when qualified as ethyl heptanoate.
• the palatability of PUFA oil is significantly improved by removing not only Maillard reaction compounds from crude PUFA oil to a low or none- detectable level, but also all or substantially all free fatty acids.
• the palatability of PUFA oil is significantly improved by removing not only Maillard reaction compounds from crude PUFA oil to a low or none-detectable level, but also all or substantially all phospholipids and cations.
• a crude oil is treated to remove all or substantially all of Maillard reaction compounds, free fatty acids, phospholipids and cation.
• the free fatty acids are removed from the PUFA oil to a level of less than 0.1% by weight of the oil.
• the level of Maillard reaction compounds in the crude oil is less than 500, less than 200, less than 100, less than 50, less than 20, less than 5, less than 2, less than 0.2, less than 0.1 ppb when qualified as ethyl heptanoate.
• the free fatty acids are removed from the PUFA oil to a level of between 1% and 0.01% by weight of the oil.
• the free fatty acids are removed from the PUFA oil to a level of less than 0.01% by weight of the oil.
• the phospholipids are removed from the PUFA oil to a level of less than 0.1% by weight of the oil.
• the phospholipids are removed from the PUFA oil to a level of between 1% and 0.01% by weight of the oil. In another embodiment, the phospholipids are removed from the PUFA oil to a level of less than 0.01% by weight of the oil. In one embodiment, the cations are removed from the PUFA oil to a level of less than 0.1% by weight of the oil. In another embodiment, the cations are removed from the PUFA oil to a level of less than 0.01% by weight of the oil. In one embodiment, the cations are removed from the PUFA oil to a level of between 1% and 0.01% by weight of the oil.
• the deodorizer is a DeSmet deodorizer.
• the deodorizer is a VTA deodorizer.
• the deodorizer can be any type of equipment which can effectively remove Maillard reaction compounds.
• the deodorizer can be any type of equipment which can effectively remove a list of Maillard reaction compounds comprising: trimethylpyrazine, 2-ethyl-3,5-dimethylpyrazine, 2-ethyl-3,6-dimethylpyrazine, tetramethyl pyrazine, 2-hydroxy-3-methyl-2-cyclopenten-l-one, methyl-lH-pyrrole-2-carboxaldehyde, and indole. Also disclosed herein is a method for enhancing palatability of a PUFA oil wherein the PUFA oil is treated by a short path evaporator. Further disclosed herein is a method for enhancing palatability of a PUFA oil wherein the PUFA oil is treated by a degumming process.
• a PUFA-containing pet food is made by mixing pet food ingredients with PUFA oil or PUFA powder.
• a PUFA-containing food for human consumption is made by mixing human food ingredient and PUFA oil or PUFA powder.
• the present invention provides for a palatability enhanced pet food by mixing pet food ingredients and the deodorized PUFA oil which is described above.
• the invention also provides for a palatability enhanced human food by mixing human food ingredients and the deodorized PUFA oil which is described above.
• the invention also provides for a palatability enhanced human nutritional supplement composition by mixing human nutritional supplement ingredients and the deodorized PUFA oil which is described above.
• the PUFA oil described herein refers to an oil which comprises PUFAs. In one embodiment, the PUFA oil described herein refers to an oil which comprises significant amount of PUFAs. In some embodiments, oil comprises at least 10%, at least 20%, at least 30%, at least 40%, at least 5%, at least 60%, at least 70%, or at least 80% by weight PUFAs.
• the source of such PUFAs in the PUFA oil may either comes from fish or microbes.
• the microbes are algae, bacteria, fungi, yeast, protist. If a significant amount of PUFAs are derived from microbe, it is referred to as microbial oil.
• PUFAs Polyunsaturated fatty acids
• docosahexaenoic acid is an omega-3 long chain polyunsaturated fatty acid (LC-PUFA) with a chain length of 22 carbons and 6 double bonds, often designated as "22:6n-3.”
• the PUFA is selected from an omega-3 fatty acid, an omega-6 fatty acid, and mixtures thereof.
• the PUFA is selected from LC-PUFAs.
• the PUFA is selected from docosahexaenoic acid (DHA), eicosapentaenoic acid (EPA), docosapentaenoic acid (DP A), arachidonic acid (ARA), gamma-linolenic acid (GLA), dihomo-gamma-linolenic acid (DGLA), stearidonic acid (SDA), and mixtures thereof.
• DHA docosahexaenoic acid
• EPA eicosapentaenoic acid
• DP A docosapentaenoic acid
• ARA arachidonic acid
• GLA gamma-linolenic acid
• DGLA dihomo-gamma-linolenic acid
• SDA stearidonic acid
• the PUFA is selected from DHA, EPA, DP A, ARA, and mixtures thereof.
• the PUFA is DHA.
• the PUFA is EPA
• the PUFAs can be in the form of a free fatty acid, salt, fatty acid ester (e.g.
• MAG monoacylglycerol
• DAG diacylglycerol
• TAG triacylglycerol
• PL phospholipid
• Free fatty acids are polyunsaturated fatty acids that have been lost from the triacylglyceride backbone or break away from oil molecules. Reduction of free fatty acids in PUFA oil is expected to reduce oxidation in long term and thus prolong shelf life of the PUFA oil.
• Crude microbial PUFA oil is normally extracted from microbial cells.
• a "cell” refers to an oil -containing biomaterial, such as biomaterial derived from oleaginous microorganisms.
• crude microbial oil refers to a crude oil extracted from the biomass of the microorganism without further processing. Crude microbial oil is normally treated before being used in pet food or human food.
• a "microbial cell” or “microorganism” refers to organisms such as algae, bacteria, fungi, yeast, protist, and combinations thereof, e.g., unicellular organisms.
• a microbial cell is a eukaryotic cell.
• a microbial cell includes, but is not limited to, golden algae (e.g., microorganisms of the kingdom Stramenopiles ); green algae; diatoms; dinoflagellates (e.g., microorganisms of the order Dinophyceae including members of the genus Crypthecodinium such as, for example, Crypthecodinium cohnii or C.
• microalgae of the order Thraustochytriales yeast ( Ascomycetes or Basidiomycetes ); and fungi of the genera Mucor, Mortierella , including but not limited to Mortierella alpina and Mortierella sect , schmuckeri , and Pythium , including but not limited to Pythium insidiosum.
• the microbial cells are from the genus Mortierella , genus
• the microbial cells are from Crypthecodinium cohnii. In yet an even further embodiment, the microbial cells are selected from Crypthecodinium cohnii , Mortierella alpina , genus Aurantiochytrium, genus Thraustochytrium , genus Schizochytrium , and mixtures thereof.
• Crude fish oil is normally extracted from fish without further processing.
• such fish may be sardine, anchovy, mackerel and/or tuna fish.
• Crude fish oil is normally treated before being used in pet food or human food.
• Plant oil is normally extracted from plant seeds.
• oil producing plant include canola, soybean, sunflower, flax, and camelina.
• the plant referred to in this invention are plants which are genetically modified to produce PUFA oil.
• a“companion animal” refers domesticated or domestic-bred animals whose physical, emotional, behavioral and social needs can be readily met as companions in the home, or in close daily relationship with humans. Examples of compasnion animals are dogs, cats, guinea pigs, rabbits, rats, mice, or horses. It is used interchangeably with the term“pet” or“pet animal” in this application.
• processed oil refers to a PUFA oil which has been processed from a crude PUFA oil.
• such treatment includes one or more step of refining, bleaching, winterizing, deodorizing, degumming or short path evaporation.
• such treatment includes only the deodorizing step.
• the treated PUFA oil of the present invention can be blended to a base pet food product, such as a dry pet or animal food.
• the pet food composition of the present intention includes various moist, oily, powdered or granular flavor additive compositions.
• the treated PUFA oil may be incorporated into the pet food as part of the manufacturing process.
• pet food products comprising treated PUFA oil from microbes or fish.
• the present invention is directed to a food product composition for a non-human animal or human, comprising any of the microbial oils of the invention.
• the food product is an additive for the non-human animal or human food.
• the food product is a nutritional supplement.
• the food product is an animal feed.
• the animal feed is a pet food.
• a crude algal oil used in this invention was extracted from the biomass of
• a crude algal PUFA oil(s) was heated to 50-55 °C under nitrogen.
• about 2% phosphoric acid was added and then mixed for 15 minutes.
• the amount of 50% caustic solution and soft water for making a caustic/tUO solution was calculated using the formula below. Excess caustic factor was increased to account for neutralizing phosphoric acid.
• the caustic/tUO solution was added to the algal oil/phosphoric acid mixture and was held for 30 minutes. 2.5% Brine Solution and 2.5% FhO were added. The resulting solution was then heat to 80-85°C and then centrifuged. The resulting oil was isolated, and was either tested for palatability or further processed by additional steps.
• the algal PUFA oil from the previous processing step such as the refinement step, was heated to 50-55 °C. 0.25-1.4% of Trisyl® (made by WR Grace Co. U.S.A.) based soaps was added to the heated solution and the solution was hold for 15min. A 2% F-72FF type of bleaching clay was added under vacuum. The oil was heated to 90-95°C and once the oil reaches set point, it was hold for 60min. After the hold the remaining oil was filtered at 91-95°C using a vertical leaf filter (VLF). The resulting oil was isolated, and was either tested for palatability or further processed by additional steps.
• VLF vertical leaf filter
• the algal PUFA oil from the previous processing step such as the bleach step, was heated to 60°C if below 45°C. The oil is then cooled to 19°C or 7°C, and was held at that temperature for 4 hours. Next, 1% Cel pure® was added (filter aid from Imerys Filtration Minerals Inc. U.S.A.) and the oil was mix for 15 minutes. The filter used in this step is a membrane filter press. The resulting oil was isolated, and was either tested for palatability or further processed by additional steps.
• the algal PUFA oil from the previous processing step was heated to 90-95°C. 3% citric acid (50% solution) and 10% FhO was added and mixed for 4 hours. After the hold time is complete, the oil solution was decanted for another 4 hours. The oil was washed with water with 10% of degummed oil weight. Mix for 4 hours and decant for 4 hrs. Dry the oil under vacuum and nitrogen at 50-60°C until moisture is ⁇ 0.5%. The filter used in this step is a membrane filter press. The resulting oil was isolated, and was either tested for palatability or further processed by additional steps.
• Short path evaporation or SPE is a specific type of refinement. It was conducted in a commercially avaible short path evaporator purchased from LCI Corporation, U.S.A.
• the rotor cage assembly surrounds an internal condenser and revolves at moderate speeds. Feed was fed through a nozzle at the top of the unit and is spread into a thin film on the inside surface of the shell via the rotor blades.
• the cage-type construction and location of the internal condenser create a short vapor flow path or“short path”.
• the operating pressure was set to 0.1 mbar compared.
• the heating media temperatures was set at 240°C.
• the flow rate was 13L/hour.
• Deodorization was performed in a VTA deodorizer or in a DeSmet deodorizers at either a continuous condition or a batch condition as shown in Table 1 below.
• VTA deodorizer was made by VTA Maschinenfabric GmbH &
• the DeSmet deodorizer was made by Desmet Ballestra Group, Belgium.
• the deodorization process was run at the condition specified by the manufactures.
• Pets such as domestic dogs and cats have different nutritional requirements and are sensitive to numerous palatability drivers.
• the animal food preference test used here is designed to identify the preference of PUFA-containing food by the tested animals.
• a total of 30 dogs were enrolled in every two-bowl tests conducted in this invention. Each test lasted for two days.
• Diet A and Diet B were prepared. Diet A is a Kibble brand pet food mixed with a testing PUFA oil sample. Diet B is the same Kibble brand pet food mixed with a control PUFA oil sample. The Kibble brand pet food may be either a dog food or a cat food, depending on which kind of animal that the test was performed on.
• the average daily consumption of each diet A and B of each dog or cat was measured.
• the amount of Diet A and Diet B consumed by each of the 30 dogs during the two-day period was measured.
• the individual intake ratios between Diet A and Diet B for each of the 30 dogs were calculated.
• the average of the 30 individual intake ratio for each diet A and B were calculated and used as indicator of the superiority of palatability of one of the two diets.
• algal oil samples processed by one or more of the refinement, bleach, winterization and deodorization steps described in Example 1 were collected. Palatability of these oil samples were measured using the testing protocol described in Example 2.
• the testing samples include an unprocessed crude algal oil as described in Example 1, and oils which were refined, and/or bleached, and/or winterized.
• a commercial fish oil sample was purchased from pet food producer and was labeled“RC fish oil”. This oil was refined, bleached, and deodorized by its manufacture before it was purchased.
• The“RC fish oil” was used as a control oil, and it was compared with the testing oil samples described above. The test results are summarized in Table 2.
• Example No. 9 which is about 24% increase from the 74.5% yield of the RBWD oil (Experiment No. 1).
• the palatability of this oil is 73.2% (Experiment No. 9), which is more than 9% higher than the 63.6% palatability score of the RBWD oil (Experiment No. 1).
• a list of ten volatiles which are commonly detected in crude fish PUFA oil and crude algal PUFA oil are described in Table 4.
• Lipid oxidation products such as l-penten-3-one, 4-heptenal, and 2,6-nonadienal are commonly found in crude fish oils and cause offensive flavor.
• the Maillard reaction products in Table 4 are commonly found in aqueous extracted algal oil and cause offensive flavor.
• an eleventh sample of ethyl heptanoate was added as an internal standard into the target volatiles list.
• ion peak area volatile peak area for selected ion for each volatile of interest
• cone IS in sample cone IS spike (123ppb) * IS spike weight / (sample weight + IS spike weight)
• The“Algal oil sample 1 crude” sample refers to an unprocessed crude algal oil extracted from Schizochytrium strain ATCC PTA-10208.
• The“Algal oil sample 1 RBWD deo VTA” sample refers to the ensuing oil after the crude algal oil sample“Algal oil sample 1 crude” was refined, bleached, winterized and deodorized by a VTA deodorizer.
• The“Algal oil sample 1 RBWD deo demet” sample refers to the ensuing oil after the crude algal oil sample“Algal oil sample 2 crude” was refined, bleached, winterized and deodorized by a DeSmet deodorizer.
• The“Algal oil sample 1 BWD deo demet” sample refers to the ensuing oil after the crude algal oil sample“Algal oil sample 1 crude” was bleached, winterized and deodorized by a DeSmet deodorizer.
• The“Algal oil sample 2 BWD deo demet” sample refers to the ensuing oil after a second sample of an unprocessed crude algal oil extracted from Schizochytrium strain ATCC PTA-10208 was bleached, winterized and deodorized by a DeSmet deodorizer.
• a commercial fish oil sample was purchased from Ocean Nutrition Corp. and was labeled“Fish oil Sample 3”. This oil was refined, bleached, and deodorized. This oil was used as the control oil sample for“Fish oil sample 3 RBWD” in the two-bowl food preference test.
• The“Fish oil sample 3 RBWD” sample refers to the ensuing oil after“Fish oil sample 3” was refined, bleached, winterized and deodorized by a DeSmet deodorizer.
• The“Algal oil sample 4 crude” sample refers to a forth sample of an unprocessed crude algal oil extracted from Schizochytrium strain ATCC PTA-10208.
• The“Algal oil sample 4 RBWD deo demet” sample refers to the ensuing oil after the crude algal oil sample“Algal oil sample 4 crude” was refined, bleached, winterized and deodorized by a DeSmet deodorizer.
• Crude algal oil samples 1, 2 and 4 are from separate batches of crude algal oil extracted from Schizochytrium strain ATCC PTA-10208.
• Crude algal oils as shown in“Algal oil Sample 1 crude” algal oil and“Algal oil sample 4 crude” algal oil, have much higher concentrations of the Maillard reaction products than their deodorized counterparts such as“Algal oil sample 2 BWD deo desmet” algal oil, and“Algal oil sample 4 RBWD deo desmet” algal oil, respectively.
• the concentration the pyrazines is particularly high where the concentrations reach hundreds to thousands of ppb (as ethyl heptanoate). In the deodorized oils, these pyrazines are either not detected or detected at ⁇ 0.3 ppb (as ethyl heptanoate).
• the other Maillard reaction products are also at significantly higher concentrations in the crude algal oils (in the 10 to 100 ppb range), whereas they are not detected in most of the deodorized oils.
• the deodorized algal oils show much smaller peaks for most compounds compared to the crude algal oils, with many of the Maillard reaction products no longer detected after deodorization.
• the use of VTA deodorization (“Algal oil sample 1 RBWD deo VTA”) shows even more improvement with fewer Maillard reaction product peaks detected and lower levels of some lipid oxidation products compared to the Desmet deodorization (“Algal oil sample 1 RBWD deo desmet”). Based on this data, as fewer of the target volatiles are detected, the palatability rating tends to improve (increase).
• the lipid oxidation products were detected at lower concentrations in the deodorized oils compared to the crude oils, but the overall concentration range of the lipid oxidation products was relatively low ( ⁇ 0.3 ppb to about 20 ppb range) and most were not fully removed by deodorization.
• the peak area of the above-mentioned volatiles for each sample were measured under the condition described above.
• sample“Fish oil Sample 3 RBWD” was deodorized using a VTA deodorizer and thus has even lower concentration of Maillard Reaction Products.
• Sample“Fish oil Sample 3 RBWD” showed an improved palatability score over an already deodorized“Fish oil Sample 3” when a VTA deodorizer was used.
• Sample“Algal oil sample 4 crude” is the control for“Algal oil sample 4 crude” in the two-bowl test.
• “Algal oil sample 4 crude” is another batch of crude algal oil which once again showed it was high in Maillard Reaction Products. After the crude algal oil is processed with refinement, bleach, winterization and deodorization steps, it was low in Maillard Reaction Products and thus has improve palatability over the control sample.
• The“1099 crude” is an unprocessed crude algal oil which was extracted from
• Schizochytrium strain ATCC PTA-10208 It was used as the starting oil for refinement, bleaching, chill-filtering and deodorization.“RC fish oil” as mentioned in Example 3 was used for the control oil in the two-bowl palatability test.
• The“1099 Refined” sample refers to the ensuing oil after the crude algal oil sample“1099 crude” was refined, but not bleached, winterized or deodorized.
• The“1099 Bleached” sample refers to the ensuing oil after the crude algal oil sample“1099 crude” was bleached, but not refined, winterized or deodorized.
• The“1099 A Chill-filtered” sample refers to the ensuing oil after the crude algal oil sample“1099 crude” was bill filtered 7 °C, but not refined, bleached, winterized or deodorized.
• The“1099B Chill-filtered” sample refers to the ensuing oil after the crude algal oil sample“1099 crude” was bill filtered 19 °C, but not refined, bleached, winterized or deodorized.
• The“1099 A Deod” sample refers to the ensuing oil after the crude algal oil sample“1099 crude” was deodorized by a VTA deodorizer and refined, bleached, and winterized at 7 °C.
• The“1099B Deod” sample refers to the ensuing oil after the crude algal oil sample“1099 crude” was deodorized by a VTA deodorizer and refined, bleached, and winterized at 19 °C.
• the deodorized algal oil shows the least intensity of offensive flavor.
• the undeodorized algal oils all have shown at least five folds or even higher intensity of offensive flavor.
• Such difference reversely correlates with the palatability scores of deodorized algal oil and algal oils which were not deodorized.
• deodorized oil has high palatability score and has low intensity of offensive flavor than algal oils which were not deodorized.
• the algal oils which were not deodorized all have low palatability score and high intensity of offensive flavor.

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