WO2017023734A1 - Préparation d'huile stable à l'oxydation ayant des acides gras oméga 3 à longue chaîne - Google Patents

Préparation d'huile stable à l'oxydation ayant des acides gras oméga 3 à longue chaîne Download PDF

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Publication number
WO2017023734A1
WO2017023734A1 PCT/US2016/044660 US2016044660W WO2017023734A1 WO 2017023734 A1 WO2017023734 A1 WO 2017023734A1 US 2016044660 W US2016044660 W US 2016044660W WO 2017023734 A1 WO2017023734 A1 WO 2017023734A1
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Prior art keywords
oil
seed
dha
epa
canola
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PCT/US2016/044660
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English (en)
Inventor
Diliara Iassonova
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Cargill, Incorporated
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Publication of WO2017023734A1 publication Critical patent/WO2017023734A1/fr

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Classifications

    • 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
    • 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
    • C11B1/00—Production of fats or fatty oils from raw materials
    • C11B1/02—Pretreatment
    • C11B1/04—Pretreatment of vegetable raw material
    • 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
    • C11B1/00—Production of fats or fatty oils from raw materials
    • C11B1/06—Production of fats or fatty oils from raw materials by pressing
    • 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
    • C11B1/00—Production of fats or fatty oils from raw materials
    • C11B1/06—Production of fats or fatty oils from raw materials by pressing
    • C11B1/08—Production of fats or fatty oils from raw materials by pressing by hot pressing
    • 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
    • C11B3/10—Refining fats or fatty oils by adsorption
    • 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
    • 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
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants
    • C11B5/0021—Preserving by using additives, e.g. anti-oxidants containing oxygen
    • C11B5/0035—Phenols; Their halogenated and aminated derivates, their salts, their esters with carboxylic acids

Definitions

  • EPA eicosapentaenoic acid
  • DHA docosahexaenoic acid
  • DPA docosapentaenoic acid
  • omega-3 polyunsaturated fatty acids may be beneficial in infant nutrition and development and in treating or preventing various mental disorders such as schizophrenia, attention deficit hyperactive disorder and
  • the present disclosure relates to the extraction and separation of an oxidatively stable oil containing at least eicosapentaenoic acid (“EPA”) and docosahexaenoic acid (“DHA”), and optionally docosapentaenoic acid (“DPA”), from a mix of a first seed that does not contain EPA or DHA, or optionally DPA, and a second seed that does contain EPA and DHA, and optionally DPA.
  • EPA eicosapentaenoic acid
  • DHA docosahexaenoic acid
  • DPA docosapentaenoic acid
  • the oil of the present disclosure may be used, for example, in human food applications, animal feed, pharmaceutical applications and cosmetic
  • a method of preparing an oil comprising DHA and EPA comprising the steps of a) obtaining a first seed and a second seed, wherein the first seed does not comprise DHA or EPA and wherein the second seed comprises DHA and EPA; b) mixing the first seed and the second seed in a ratio of about 1:9 to about 9:1 to provide a seed mix; and c) pressing the seed mix to provide the oil comprising DHA and EPA.
  • Figures 1 and 2 graphically demonstrate the oxidative stability of pressed oils of the present disclosure compared to the oxidative stability of oil blends.
  • Figures 3 and 4 graphically demonstrate the oxidative stability of pressed oils of the present disclosure containing antioxidants compared to the oxidative stability of oil blends containing antioxidants.
  • Figures 5 and 6 graphically demonstrate the oxidative stability of extracted meal oils of the present disclosure.
  • Figure 7 graphically demonstrates the color of pressed oils of the present disclosure.
  • Figure 8 graphically demonstrates the chlorophyll value of pressed oils of the present disclosure.
  • Figure 9 lists the fatty acid percentages in pressed oils of the present disclosure.
  • Figure 10 graphically demonstrates the oxidative stability index ("OSI") of oil from canola seeds including DHA, EPA, and/or DPA ("tCanola”) and seeds not including DHA, EPA, and/or DPA (“Canola”), where the seeds were subjected to a 40 °C storage temperature for up to 120 days.
  • Figure 11 graphically demonstrates weight percentage of total saturated fats measured in the oils oil from canola seeds including DHA, EPA, and/or DPA (“tCanola”) and seeds not including DHA, EPA, and/or DPA (“Canola”), where the seeds were subjected to a 40 °C storage temperature for up to 120 days.
  • Figure 12 graphically demonstrates the weight percentage of DHA + EPA present in oil from seeds including DHA, EPA, and/or DPA ("tCanola”), where the seeds were subjected to a 40 °C storage temperature for up to 120 days.
  • oil comprising DHA and EPA means pressed oil, meal oil, or Refined Bleached Deodorized (“RBD”) oil containing eicosapentaenoic acid (“EPA”) and docosahexaenoic acid (“DHA”).
  • RBD Refined Bleached Deodorized
  • EPA eicosapentaenoic acid
  • DHA docosahexaenoic acid
  • seed refers to the seed, bean, or nut of a plant from which oil can be expressed and/or extracted such as, for example, a rapeseed (e.g., canola), a sunflower seed, a poppy seed, a sesame seed, a soy bean, a pistachio, a peanut, a cashew, a walnut, a pine nut, or an almond.
  • rapeseed e.g., canola
  • sunflower seed e.g., a sunflower seed
  • poppy seed e.g., a sesame seed
  • soy bean e.g., a soy bean
  • a pistachio e.g., a peanut, a cashew, a walnut, a pine nut, or an almond.
  • the first seed i.e., the seed that does not comprise DHA and EPA
  • Canola seeds useful in in embodiments of the present application are available commercially, for example, from Cargill, Incorporated, Wayzata Minnesota, USA.
  • the second seed i.e., the seed that does comprise DHA and EPA
  • modified or transformed canola seeds for example, with increased levels of DHA and EPA, and optionally DPA, mixed with canola seeds with no or no significant levels of DHA, EPA, and/or DPA may be hot
  • a paint- like or fish- like aroma or odor is generally considered undesirable as it may indicate an edible oil of low nutritional value and poor oxidative status, i.e., an edible oil that is not fresh.
  • Oxidative stability of oils made from a mixture of seeds, some seeds including DHA, EPA, and/or DPA and other seeds not including DHA, EPA, and/or DPA, is surprisingly similar to oil not containing DHA, EPA and/or DPA, as one skilled in the art would expect an oil containing any of the oxidatively less stable polyunsaturated fatty acids such as DHA, EPA and DPA to be less stable when compared to an oil not containing such polyunsaturated fatty acids.
  • One embodiment of the present disclosure is a method of preparing an oil comprising DHA and EPA, the method comprising the steps of a) obtaining a first canola seed and a second canola seed, wherein the first canola seed does not comprise DHA or EPA and wherein the second canola seed comprises DHA and EPA (the second canola seed may optionally further comprises DPA); b) mixing the first canola seed and the second canola seed in a ratio of about 1:9 to about 9: 1 to provide mixed seed; and c) pressing the mixed seed to provide the oil.
  • the ratio of first and second canola seeds may be in ranges of 1:4, 3:7, 2:3, 1: 1, 3:2, 7:3, or 4: 1.
  • the ratio of first and second canola seed may be selected in order to provide an oil comprising about 0.1% to about 5% DHA, about 0.1% to about 15% of EPA, and optionally about 0.1% to about 15% DPA.
  • the second canola seed comprising DHA and EPA may be stable under storage conditions at 40 °C, demonstrating less than a 30%, less than a 29%, less than a 28%, less than a 27%, less than a 26%, or less than a 25% decrease in oxidative stability index ("OSI") at 110 °C after storage for at least 120 days.
  • OSI oxidative stability index
  • the second canola seed may further demonstrate no significant decrease in the weight percentage of total saturated fats and/or in the weight percentage of DHA + EPA in the seed oil after storage for at least 120 days.
  • the mixed seed of step b. may be tempered using conventional, known processing conditions to provide mixed seed with a moisture content of about 5% to about 15%.
  • Some embodiments of the present disclosure may include about 0.1% to about 5% DHA, about 0.1% to about 15% of EPA, and optionally about 0.1% to about 15% DPA.
  • the mixed seed may be ground or flaked before pressing in order to provide either a ground or flaked mixed seed.
  • the ground or flaked mix seed may be heat conditioned. Heat conditioning, in part, inactivates undesired enzymes in the seed that well detrimentally affect the physical properties or characteristics of the resulting oil. Suitable heat conditioning conditions may include heating the flaked mixed seed at a temperature in the range of about 80 °C to about 110 °C for a period of time of about 20 minutes to about 90 minutes, as well as other heating methods or processes conventionally used in the oil processing industry.
  • either the first or the second seed, or both the first and the second seed may be treated with an antioxidant.
  • Treatment with an antioxidant can occur before the first and second seed are combined, while the first and second seed are being combined, or after the first and second seed are combined.
  • the first seed may be treated with a first antioxidant and the second seed may be treated with a second antioxidant that is different than the first antioxidant.
  • the expressed oil, before or after further processing may be treated with an antioxidant. The antioxidant added to the expressed oil may be the same antioxidant used to treat the first and/or the second seed or it may be a different antioxidant.
  • Suitable antioxidants may include, for example, at least one of tert-butyl hydroquinone (“TBHQ”), butylated hydroxytoluene (“BHT”), butylated hydroxyanisole (“BHA”), and/or propyl gallate, as well as other conventional, known agents added to foods containing fats and oils to prevent oxidation.
  • TBHQ tert-butyl hydroquinone
  • BHT butylated hydroxytoluene
  • BHA butylated hydroxyanisole
  • propyl gallate propyl gallate
  • a suitable antioxidant is a TBHQ and propyl glycol blend sold under the trade name GRINDOX 512 by Danisco (DuPont Nutrition & Health, Copenhagen, Denmark).
  • Another example of a suitable antioxidant is a 0.3% rosemary and tocopherols blend sold by Naturex, Inc., Avignon, France.
  • Another example of a suitable antioxidant is a 0.3% rosemary and citric acid blend sold by Kalsec
  • antioxidants may include a suitable synthetic antioxidant typically used in food, feed, pharmaceuticals, or cosmetics.
  • a synthetic antioxidant for example, may be dissolved in a water or oil solution (e.g., propyl glycol), and may be then sprayed onto seed at a concentration of less than about 200 ppm.
  • pressing the oil further comprises hot pressing the mixed seed to provide a meal and solvent extracting the oil from the meal.
  • the method may include grinding or flaking the mixed seed of step b. to provide ground or flaked mixed seed as well as heat conditioning the ground or flaked mixed seed to provide heat conditioned ground or flaked mixed seed by, for example, heating the flaked mixed seed at a temperature in the range of about 80 °C to about 110 °C for a period of time of about 20 minutes to about 90 minutes.
  • the oil of the present disclosure may be further treated or processed using conventional, known refining, bleaching and deodorizing treatments, such as the refining, bleaching, and deodorizing treatments described by Daun et al. Canola: Chemistry,
  • the DHA and EPA oil has an desirable physical properties or characteristics such as an oxidative stability index (“OSI”) per the American Oil
  • Chemist's Society Official Method Cd 12b-92 (revised 2013) of about at least about 4 hours for refined, bleached, and deodorized (“RBD”) oil and at least about 1 hour for pressed oil and meal oil, a stability determined by an accelerated oxidative stability test at 60°C (Schall oven test) of hydroperoxide formation (Peroxide Value (“PV”) AOCS Cd 8b-90), about less than 10 miUieqivalents peroxide/kg of oil after 3 days at 60 °C , less than 20 PV after 6 days at 60°C, less than 30 PV after 9 days at 60°C , less than 70 PV after 12 days at 60°C; a color of about less than 1 Red for RBD using AOCS Method # Cc 13b-45 ( as reapproved 2009) and about less than 20 Red for pressed and meal oils that is measured according to AOCS Method Td la-64.
  • oil of the present disclosure may be used in a variety of applications such as, for example, dietetic, pharmaceutical, or cosmetic compositions. Suitable compositions using oil of the present disclosure are reported in US 7,807,849, US Pub No 2005/0129739, EP 1 117 303B1 and EP 1 401 259B1, all incorporated by reference herein.
  • OSI Oxidative Stability Index
  • AOCS American Oil Chemist's Society
  • OSI testing of each sample must occur at the same temperature; OSI values determined at 110 °C are most common in the edible oil industry.
  • OSI is used for prediction of oil stability during storage (i.e., oil shelf life) and how oils may behave during food processing (e.g., frying, baking) and product storage (i.e., product shelf life).
  • a typical OSI value at 110°C for sunflower oil is 3-5 hours, and for soybean oil is 4-7 hours.
  • Table 1 The correlation of OSI values at 110 °C to physical characteristics of an oil are summarized in Table 1.
  • PV Peroxide Value
  • the color of RBD oils of the present disclosure may be readily determined using AOCS Official Method Cc 13b-45 (reapproved 2009) titled "Wesson Method Using Color Glasses Calibrated in Accordance with the AOCS-Tinometer Color Scale".
  • the color of a liquid oil is determined by comparing the color of the oil with the color of one or more standardized color glasses using particular colorimeters as specified by the published method.
  • the color for pressed and meal oils (the "Gardner red” value) of the present disclosure may be readily determined using AOCS Method Td la-64.
  • Color is important quality characteristic of an oil because it correlates with oil freshness and composition. For example, red pigments formed during thermal oil degradation (e.g., during frying), may affect the final product color of baked goods and fried foods.
  • Typical industry color (red) specification (“R") is less than aboutlR for an RBD oil and less than about 20 R for pressed and meal oils.
  • Chlorophyll level is an important quality parameter for seed, pressed oil, meal oil and bleached oil. Chlorophyll is a group of green pigments and is important not only because it may affect the final appearance of a product, but also because it indicates the maturity of seeds, it can affect oil refining parameters(e.g., the amount of bleaching earth needed), and the oxidative stability of oils (chlorophyll is a prooxidant). For seeds and pressed oil, a typical chlorophyll specification is ⁇ 30 ppm. For bleached oil, a typical chlorophyll specification is ⁇ 30 ppb.
  • the fats are analyzed via a gas chromatograph determination of fatty acid profile per AOCS Official Method Ce li- 07.
  • a desired ratio e.g., first seed:second seed ratio of 1:9 to 9: 1
  • CENTRIFIC 225a centrifuge (Thermo Fisher Scientific Inc., Waltham, MA USA) at speed setting #6 for 5 minutes. Pipet the clear oil from the centrifuge tube for testing.
  • test clear oil immediately or transfer it to a vial that has been purged with an inert gas, (e.g., nitrogen), flush with and inert gas (e.g., nitrogen), seal immediately, and refrigerate sample at 4 °C.
  • an inert gas e.g., nitrogen
  • flush with and inert gas e.g., nitrogen
  • Canola oil Samples A and B were prepared from CV80 high oleic canola seeds without DHA and EPA, commercially available from Cargill, Incorporated, as described in Example 1.
  • Canola oil Samples C and D were prepared from mixed canola seeds, i.e., 40 wt% CV80 high oleic canola seeds without DHA and EPA commercially available from Cargill, Incorporated, plus 60 wt% of a canola seed including about 8.5 wt% EPA+DHA ("tCanola").
  • the oils were tested for the physical characteristics and properties listed in Table 2, below. The tests were made on the crude oils as well as oils that were refined, bleached, and deodorized according to the further treatment steps described above.
  • 3501b of seed blend was prepared (60% tCanola blended with 40% CV80).
  • Sample D 21 kg pressed tCanola oil were blended with 5kg CV80 crude oil (81%/19% blend). Seeds moisture was measured and then adjusted with water to achieve about 12% moisture. Seeds were blended with tumbler blender and tempered for at least 8 hours. Tempered seeds were flaked with roller flaker to achieve about 0.22mm flake thickness. Flakes were transferred to a FRENCH Model 324 Vertical, Stacked Conditioner (French Oil Mill Machinery Co., Piqua, OH, USA) and treated at 100 °C for 30 min. Hot conditioned flakes were
  • Sample oils A-D meet RBD oil quality specification of good quality RBD oil (free fatty acids (“FFA”), color, and chlorophyll). All oils have a clean aroma without any off notes.
  • Sample oil C has an OSI at 110 °C of 8 hours and Sample oil D has an OSI at 110 °C of4 hours, OSI hours comparable to commodity oils.
  • Sample D was further stabilized by blending RBD high oleic canola oil (CV80) and antioxidants to achieve OSI hours of a high-stability oils, as shown in Table 3.
  • tCanola DHA + EPA canola seed
  • Blends of CV80 high oleic canola seeds (“CV80”) or commodity canola seeds (“Canola”) without DHA and EPA, commercially available from Cargill, Incorporated, and canola seed including about 8.5 wt% EPA+DHA (“tCanola”) were prepared to the desired ratios of CV80 or Canola:tCanola, i.e., 1:9, 2:8,3:7, 4:6, 5:5, 6:4, 7:3, 8:2, and 9: 1 to provide mixed seed.
  • the seed mixes were individually ground/expelled and the resulting meals were extracted as described in Example 1 and are hereinafter referred to as "oils made from seed blends" ("SB").
  • OB oil blends
  • Figure 1 is a graph of the oxidative stability index ("OSI”) at 110 °C of pressed oils made from CV80/tCanola seed blends (“SB”) and oil blends ("OB”).
  • Figure 2 is a graph of the oxidative stability index (“OSI”) at 110 °C of pressed oils made from Canola/tCanola seed blends (“SB”) and oil blends (“OB”).
  • oils having a DHA+EPA content of less than 5% prepared with CV80 ( Figure 1, as well those oils prepared with Canola ( Figure 2), surprisingly demonstrated oxidative stability typical of commodity canola oils, i.e., 4-10 hours, or even the oxidative stability typical of high stability oils, i.e., greater thanlO hours.
  • Figure 3 is a graph of the oxidative stability index ("OSI”) at 110 °C of pressed oils with added antioxidant (3000 ppm) made from CV80/tCanola seed blends (“SB”) and oil blends ("OB”).
  • Figure 4 is a graph of the oxidative stability index (“OSI”) at 110 °C of pressed oils with added antioxidant (3000 ppm) made from CV80/tCanola seed blends (“SB”) and oil blends (“OB”).
  • oils having DHA+EPA content of less than 8.5% prepared with CV80 ( Figure 3), as well with Canola ( Figure 4), with rosemary and ascorbic acid antioxidants added demonstrated a strong response to antioxidants addition, i.e., Samples with DHA+EPA content of 6.7-8.5% had oxidative stability typical of commodity oils, and samples with DHA+EPA content of less than 6% had oxidative stability typical of high-stability oils.
  • Canola seeds including about 8.5 wt% DHA + EPA (“tCanola”) and commodity canola seeds not including DHA or EPA (“Canola”) were stored 40 °C in a forced-air oven without humidity control. Oils were pressed from the seeds as described in Example 1 after storage for up to 120 days. The oxidative stability index ("OSI”) at 110 °C, weight percentage of total saturated fats, and weight percentage of DHA + EPA were determined as described above.
  • OSI oxidative stability index
  • Figure 10 is a graph of the oxidative stability index ("OSI") at 110 °C of pressed oils made from Canola seeds and tCanola seeds.
  • OSI oxidative stability index

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Abstract

La présente invention concerne l'extraction et la séparation d'une huile stable à l'oxydation contenant au moins de l'acide eicosapentaénoïque ("EPA") et de l'acide docosahexaénoïque ("DHA"), et éventuellement de l'acide docosapentaénoïque ("DPA"), à partir d'un mélange d'une première graine qui ne contient pas d'EPA ou de DHA, ou éventuellement de DPA, et d'une deuxième graine qui contient de l'EPA et du DHA, et éventuellement du DPA.
PCT/US2016/044660 2015-07-31 2016-07-29 Préparation d'huile stable à l'oxydation ayant des acides gras oméga 3 à longue chaîne WO2017023734A1 (fr)

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Cited By (2)

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Publication number Priority date Publication date Assignee Title
WO2017156059A1 (fr) * 2016-03-08 2017-09-14 Cargill, Incorporated Huile de colza stabilisée comprenant des acides gras polyinsaturés et des antioxydants solubles dans l'huile
CN112040766A (zh) * 2018-04-13 2020-12-04 嘉吉公司 栽培含lc-pufa的转基因芸苔属植物的方法

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US20060110521A1 (en) * 2004-11-04 2006-05-25 Monsanto Technology, Llc High PUFA oil compositions
US20070066565A1 (en) * 2003-08-28 2007-03-22 Kazuhisa Mukai Cyclic maltosylmatose
US20080280009A1 (en) * 2006-11-14 2008-11-13 Thomas Greither Nutritional food oil compositions and methods of making same
US20130177692A1 (en) * 2011-12-30 2013-07-11 Dow Agrosciences Llc Dha retention during canola processing
WO2014089274A1 (fr) * 2012-12-05 2014-06-12 Cargill, Incorporated Graisses stabilisées de manière oxydante contenant des acides gras polyinsaturés oméga 3 à très longue chaîne et leurs utilisations

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Publication number Priority date Publication date Assignee Title
GB2147911A (en) * 1983-10-14 1985-05-22 Nestle Sa A process for the preparation of fatty substances
US5696278A (en) * 1993-03-17 1997-12-09 Unilever Patent Holdings B.V. Degumming of crude glyceride oils not exposed to prior enzymatic activity
US20070066565A1 (en) * 2003-08-28 2007-03-22 Kazuhisa Mukai Cyclic maltosylmatose
US20060110521A1 (en) * 2004-11-04 2006-05-25 Monsanto Technology, Llc High PUFA oil compositions
US20080280009A1 (en) * 2006-11-14 2008-11-13 Thomas Greither Nutritional food oil compositions and methods of making same
US20130177692A1 (en) * 2011-12-30 2013-07-11 Dow Agrosciences Llc Dha retention during canola processing
WO2014089274A1 (fr) * 2012-12-05 2014-06-12 Cargill, Incorporated Graisses stabilisées de manière oxydante contenant des acides gras polyinsaturés oméga 3 à très longue chaîne et leurs utilisations

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017156059A1 (fr) * 2016-03-08 2017-09-14 Cargill, Incorporated Huile de colza stabilisée comprenant des acides gras polyinsaturés et des antioxydants solubles dans l'huile
CN112040766A (zh) * 2018-04-13 2020-12-04 嘉吉公司 栽培含lc-pufa的转基因芸苔属植物的方法
US11957098B2 (en) 2018-04-13 2024-04-16 Basf Plant Science Company Gmbh Method of cultivating LC-PUFA containing transgenic brassica plants

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