WO2012145119A2 - Huiles mélangées faiblement inflammatoires - Google Patents

Huiles mélangées faiblement inflammatoires Download PDF

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Publication number
WO2012145119A2
WO2012145119A2 PCT/US2012/030232 US2012030232W WO2012145119A2 WO 2012145119 A2 WO2012145119 A2 WO 2012145119A2 US 2012030232 W US2012030232 W US 2012030232W WO 2012145119 A2 WO2012145119 A2 WO 2012145119A2
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Prior art keywords
oil
omega
low inflammatory
weight
utilizing
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WO2012145119A3 (fr
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Michael Gurin
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
    • A61K31/202—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids having three or more double bonds, e.g. linolenic
    • 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
    • A23L33/105—Plant extracts, their artificial duplicates or their 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
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • A23L33/11—Plant sterols or derivatives thereof, e.g. phytosterols
    • 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
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/48—Fabaceae or Leguminosae (Pea or Legume family); Caesalpiniaceae; Mimosaceae; Papilionaceae
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/53—Lamiaceae or Labiatae (Mint family), e.g. thyme, rosemary or lavender
    • A61K36/537—Salvia (sage)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/55—Linaceae (Flax family), e.g. Linum
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/88—Liliopsida (monocotyledons)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/88—Liliopsida (monocotyledons)
    • A61K36/889—Arecaceae, Palmae or Palmaceae (Palm family), e.g. date or coconut palm or palmetto
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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

  • Hi Oleic Peanut Oil hereinafter referred to as "Peanut-Hi9"
  • Peanut-Hi9 has both ⁇ 3.5% of linoleic, preferably ⁇ 3.2%, and specifically preferred ⁇ 2.95% on a weight basis, w/ oleic > 75%) and specifcally preferred > 79% on a weight basis.
  • High-oleic Moringa Oleifera seed oil hereinafter referred to as "MO-Hi" has both ⁇ 3.0%) of linoleic, preferably ⁇ 2.0%, and specifically preferred ⁇ 1.0%> on a weight basis, with an oleic composition > 70%> and specifcally preferred > 74% on a weight basis.
  • High linolenic Flax Oil is hereinafter referred to as "Flax-Hi3"
  • Flax-Hi3 has a linolenic to linoleic ratio > 6, preferably > 6.2, specifically preferred > 6.4, and also linolenic > 65%, preferably > 68%, specifically preferred > 72% on a weight basis.
  • Salvia hispanicaL.(chia) is hereinafter referred to as "Salba", is the most nutritionally dense form of chia. There are over 80 generic strains of chia, and Salba is a blend of the only two registered varieties - SahiAlba 911 & 912.
  • One embodiment of the 03-PUFA delivery system is an omega-3 long chain PUFA concentrate comprised of multiple oils resulting in an aggregate of omega-6 to omega-3 long chain PUFA ratio is from 0.01 to 2.8. The preferred ratio is between 0.01 to 0.24.
  • the preferred second oil has an omega-9 to omega-6 ratio from 5 to 20, and is blended with an omega-3 enriched oil (e.g., fish oil, concentrate fish oil, microalgae oil such as Martek TM, etc.) having a 03-PUFA content of at least 20 percent on a weight basis.
  • the specifically preferred second oil has less than 2.5% by weight of linolenic acid in order to minimize oxidation between the manufacturing and consumption periods of time.
  • Linolenic which is a short chain omega-3, does not have a competing interaction with long-chain omega-3, but as noted will adversely impact shelf life.
  • the particularly preferred second oil also has an omega-6 to omega-3 long chain PUFA ratio from 0.01 to 2.8, and more preferably between 0.01 to 0.24; and an omega-9 to omega-6 ratio of at least 5 to 1 (preferably between about 50 to 1, and more preferably between from about 20 to 5, and particularly preferable between from about 50 to 20).
  • the omega-3 long chain PUFA concentrate is subsequently added to a wide range of consumer products including food, beverage, nutritional supplement, or pharmaceutical products having an omega-3 dosage of greater than 50 mg per serving, but at least 30 mg per serving.
  • the particularly preferred formulation notably for food products that are rich in oil (e.g., mayonaisse, salad dressings, peanut butter, etc.) utilize oils having an aggregate of omega-6 having a weight % less than 5%, though preferably less than 2.1%.
  • a preferred formulation further comprises a sinapyl compound including the sinapyl compound as isolated from pineapple juice.
  • the particularly preferred formulation does not require pineapple juice, but utilizes a sinapyl compound as isolated from pineapple juice into the omega-3 long chain concentrate.
  • the concentrate contains a sulfur containing antioxidant particularly when iron is present in the food, beverage, nutritional supplement, or pharmaceutical products.
  • the particularly preferred sulfur containing antioxidant is isolated from broccoli.
  • Yet another alternative antioxidant, and the specifically preferred contains at least one of sulforaphane and a sulforaphane precursor glucosinolate including sulforaphane glucosinolate.
  • Another embodiment of antioxidant is ferulic acid, particularly from coffee fruit.
  • Another embodiment is the resulting blended oil having an omega-6 to omega-3 ratio from 0.1 :1 to 1 :3, and at least the first oil and the second oil containing less than 6% by weight of linolenic acid.
  • omega- 6 to omega-3 ratio is from 0.01 to 1.0.
  • a particularly preferred blend of antioxidant is a curcumin C3 complex on a weight basis of at least 10 ppm, and Vitamin E of at least 100 ppm.
  • a specifically preferred blend alternatively includes a manganese oxide emitting a blue color at ambient temperatures on a weight basis of at least 10 ppm, and Vitamin E of at least 100 ppm.
  • a preferred method of utilizing the omega-3 long chain PUFA concentrate is to prepare the omega-3 long chain PUFA oil into an emulsion (preferably a microemulsion, and particularly preferred as a nanoemulsion) with the antioxidant subsequently added to the water phase with the already prepared omega-3 long chain PUFA concentrate micro- or nano- emulsion.
  • the particularly preferred method of preparing the emulsion is the addition of medium chain triglyceride at a weight ratio to omega-3 long chain PUFA of at least .25 to 3, and an emulsifier at a ratio to omega-3 long chain PUFA of at least .25 to 3.
  • the prepared micro- or nano- emulsion is then subsequently added to a food or beverage product at a level of at least 35 to 2000 mg of omega-3 long chain PUFA per serving.
  • phytosterols converted from non-esterified phytosterols to triglyceride- recrystallized phytosterols provide superior performance, but the inventive recrystallized phytosterols are converted from non-esterified phytosterols to triglyceride-recrystallized phytosterols using medium chain triglycerides.
  • the triglyceride-recrystallized phytosterols is infused into the omega-3 long chain PUFA concentrate by at least one of the sequential steps of:
  • Yet another embodiment of the omega-3 long chain PUFA concentrate utilizes at least one of vegetal chitosan and chitin-glucan at 0.1 to 4.0 percent by weight of a second oil wherein the at least one of vegetal chitosan and chitin-glucan is mixed into the second oil prior to being incorporated into the omega-3 long chain PUFA concentrate.
  • the vegetal chitosan and/or chitin-glucan preferentialy adsorbs the second oil (i.e., the non-omega-3 long chain PUFA containing oil) limiting it's bioavailability while providing an "encapsulant" around the omega-3 long chain rich portion of the micro- or nano- emulsion.
  • Maximizing the adsorption of the non-omega-3 long chain oil is preferentially achieved inclusion of the at least one of vegetal chitosan and chitin-glucan into the second oil, preferentially combined with supercritical carbon dioxide at a ratio of between 100 and 0.5 for second oil to supercritical carbon dioxide.
  • the preferred sources of ingredients utilized in the invention are:
  • Vegetal chitosan and/or chitin-glucan from KitoZyme Vegetal chitosan and/or chitin-glucan from KitoZyme.
  • Second oil is coconut oil.
  • the more preferred is a high oleic peanut oil including cultivars AT-201, GA-02C, and FR-458.
  • the specifically preferred is MO-Hi.
  • Ferulic acid is from coffee fruit by KonaRed of Sandwich Isles Trading Company, Inc.
  • At least 2% of pineapple juice on a weight basis to the omega-3 long chain PUFA weight is sulforaphane and a sulforaphane precursor glucosinolate including sulforaphane glucosinolate from pineapple.
  • Curcumin C3 complex on a weight basis of at least 10 ppm, inositol on a weight basis of at least 50 ppm and mixed tocotrienols of at least 100 ppm
  • Manganese oxide emitting a blue color at ambient temperatures as known in the art by by Mas Subramanian of Oregon State University in Corvallis
  • Medium chain triglyceride is MC-5 from Stepan
  • Food product e.g., Peanut for OCLC mg oil weight Juice for g per for g per in grams Oil GA-02C per serving fraction serving serving
  • a method for improving the glucose tolerance of a glucose intolerant individual comprising administering a lipid system comprising alpha-linolenic acid (C18:3n-3), omega- 6 fatty acids, and omega-9 fatty acids wherein the ratio of said omega-6 fatty acids to said alpha-linolenic acid (C18:3n-3) is from about 0.25:1 to about 3: 1, and the ratio of said omega-9 fatty acids to said alpha-linolenic acid (C18:3n-3) is from about 0.4: 1 to about 3: 1.
  • a method for improving the glucose tolerance of a glucose intolerant individual comprising administering a lipid system to said glucose intolerant individual, said lipid system comprising omega-3 fatty acids, omega-6 fatty acids, and omega-9 fatty acids wherein the ratio of said omega-6 fatty acids to said omega-3 fatty acids is between 0.25: 1 and 3: 1; and the ratio of said omega-9 fatty acids to said omega-3 fatty acids is between 0.4: 1 and 3: 1.
  • a nutritional supplement for administration to children comprising: a protein component; a carbohydrate component; and a lipid component comprising a source of DHA, wherein the supplement has an omega.-6: .omega.- 3 fatty acid ratio of about 6: 1 or less.
  • a nutritional supplement for administration to children comprising: a protein component; a carbohydrate component; and a lipid component comprising, in % w/w of the total lipid component: between about 10% and about 50%> canola oil; between about 5%> and about 40%> soy oil; between about 5%> and about 40%> high oleic sunflower oil; between about 5%> and about 40%> medium chain triglyceride oil;
  • a prepared food product comprising a cholesterol- free fat composition having a balanced mixture of fatty acids, comprising between 15 > by weight and 40%> by weight linoleic acid, between 20%> and 40%> by weight saturated fatty acid comprising at least one saturated fatty acid selected from the group consisting of lauric acid, myristic acid, and palmitic acid, and no more than 1% elaidic acid or other unnatural trans fatty acids by weight; wherein the ratio of polyunsaturated fatty acids, including linoleic acid, to saturated fatty acids is from 0.5: 1 to 2: 1, and wherein said fat composition and said food product are suitable for human or animal ingestion for increasing the HDL concentration and the HDL/LDL concentration ratio in the blood serum.
  • a cholesterol-free fat composition having a balanced mixture of fatty acids, comprising between 15% by weight and 40% by weight linoleic acid, between 20%> and 40%> by weight saturated fatty acids, wherein at least one said saturated fatty acid is selected from the group consisting of lauric acid, myristic acid, and palmitic acid, and no more than 1% elaidic acid or other unnatural trans fatty acids by weight; wherein the ratio of
  • polyunsaturated fatty acids including linoleic acid, to saturated fatty acids is from 0.5: 1 to 2: 1, and wherein said cholesterol-free fat composition is suitable for human or animal ingestion for increasing the HDL concentration and the HDL/LDL concentration ratio in the blood serum.
  • the nutritional additive of claim 2 wherein the ratio of omega-3 fatty acids to omega-
  • the invention desires to achieve a balanced omega-3 to omega-6 ratio (i.e., greater than 1, and under all circumstances less than 0.25 which remains superior to the oil ratio utilized within the classic Western diet).
  • the oil blend is comprised of at least two oils, a first oil high in linolenic and a second oil high in with ultra-low linoleic oil.
  • a particularly preferred third oil is further included an omega-3 (in the form of DHA and/or EPA) concentrate wherein the omega-3 is greater than 25%, preferably greater than 50%, and specifically preferred greater than 55%.
  • the oil blend composition is a blend of at least two oils comprised of a first oil Flax- Hi3 where the Flax-Hi3 is ⁇ 8%> (preferably ⁇ 7.5%>, specifically ⁇ 7.4%>) and a second oil of Peanut Oil - GA-02C > 91%.
  • the oil blend has an oleic composition > 60%, preferably > 63%, and specifically > 64.5%.
  • the oil blend composition is a blend of at least two oils comprised of a first oil Flax- Hi3 where the Flax-Hi3 within the balanced Omega-3 :Omega-6 oil (a ratio of > 1) oil composition having ⁇ 6% Flax-Hi3 oil, preferably ⁇ 5%, and more specifically ⁇ 4%; with a second oil of Peanut-Hi9 > 95%, such that the blend has an oleic weight composition > 65%, preferably > 70%>, and more specifically > 74%.
  • oil blend composition with the term oil blend composition interchangeable used as omega-3 concentrate, is a balanced Omega-3 :Omega-6 oil (a ratio of
  • oil blend composition with the term oil blend composition interchangeable used as omega-3 concentrate, is a balanced Omega-3 :Omega-6 oil (a ratio of
  • oil blend composition with the term oil blend composition interchangeable used as omega-3 concentrate, is a balanced Omega-3 :Omega-6 oil (a ratio of
  • the oil blend is best with an omega-6 to omega-3 ratio from 0.01 to 2.8, and preferably from 0.3 to 1.2. More preferred is such that the omega-6 to omega-3 ratio is less than, such as from 0.5 to 0.99.
  • the omega-3 content of the first oil has at least 20 percent on a weight basis, and the second oil has an omega-9 to omega-6 ratio from 5 to 90.
  • omega-3 oil blend that contains less than 6% by weight of linolenic acid and the omega-6 to omega-3 ratio is from 0.5 to 0.99. More preferred is an oil blend that contains less than 4% linolenic by weight basis and specifically preferred is less than 2% linolenic.
  • the ultimate low inflammatory oil has less than 2% by weight basis of linoleic and an omega-6 to omega-3 ratio less than 1.
  • the best and healthiest method of achieving a balanced omega-6 to omega-3 ratio is by minimizing the weight percentage of linoleic acid.
  • the preferred oleic weight percentage basis is greater than 60% or alternatively when using coconut oil the oleic weight percentage basis is less than 3%.
  • the particularly preferred oleic weight basis is greater than 65%, and the specifically preferred oleic weight basis is greater than 70%.
  • the second oil preferably has an omega-9 to omega-6 ratio greater than 9, and preferably greater than 25.
  • the first oil has a linolenic weight percentage greater than 70%.
  • the first oil exception is the use of Salba that naturally has anti-inflammatory benefits further amplified by minimizing linoleic acid in the blend and the second oil exception is coconut oil that is virtually void of oils having carbon length greater than 13.
  • the omega-3 blend is further comprised of a third oil to incorporate long-chain omega-3, as compared to short chain (i.e., linolenic) having an omega-6 to omega-3 ratio from 0.01 to 0.20, wherein the third oil is comprised of at least 30% by weight of a combination of DHA and EPA.
  • At least a first oil and a second oil resulting in a blended oil having an omega-6 to omega-3 ratio from 0.01 to 3, has a blended composition of at least 60% oleic acid, at least 0.5% linolenic acid, and at most 8.0% linoleic acid; or
  • At least 65% oleic acid at least 8.0% linolenic acid, and at most 3.0% linoleic acid; or at least 65% oleic acid, at most 4.0% linolenic acid, and at most 3.0% linoleic acid.
  • the utilization of the preferred LI Oil is included a wide range of food and nutraceutical products as known in the art. It is further understood that dual (or otherwise known as isolated) packages such that the first oil and third oil are within one of the dual packages and the second oil is in the other of the dual packages.
  • the inclusion of the LI Oil is utilized in the same method as inclusion of traditional food oils, omega-3 enriched oils, etc.
  • Each of the above formulations further utilize the omega-3 oil blend further comprised of a third oil containing at least 30% by weight of combined DHA and EPA.
  • the now omega-6 to omega-3 oil blend is balanced and incorporated into at least one of a food, beverage, nutritional supplement, or pharmaceutical, and wherein the combination of DHA and EPA is at least 30 mg per serving.

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  • Engineering & Computer Science (AREA)
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Abstract

L'invention concerne une composition d'huile faiblement inflammatoire et un procédé pour supplémenter des systèmes d'alimentation animale, de nutrition et de régime par des huiles équilibrées en oméga-3 à oméga-6 composées d'un mélange synergique d'au moins deux huiles. La composition comprend en outre un mélange synergique d'une huile oméga-3 à longue chaîne en tant que moyen pour augmenter encore la valeur nutritionnelle. La composition assure en outre une augmentation efficace de la réduction de l'inflammation pour un traitement thérapeutique et pharmacologique en addition à des systèmes généraux de nutrition et de régime.
PCT/US2012/030232 2011-04-17 2012-03-23 Huiles mélangées faiblement inflammatoires Ceased WO2012145119A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201113088417A 2011-04-17 2011-04-17
US13/088,417 2011-04-17

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WO2012145119A2 true WO2012145119A2 (fr) 2012-10-26
WO2012145119A3 WO2012145119A3 (fr) 2012-12-27

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2968990A4 (fr) * 2013-03-15 2016-08-24 Nutramax Lab Inc Compositions comprenant du sulforaphane ou un précurseur de sulforaphane et un phytostérol ou un phytostanol

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6224926B1 (en) * 1999-08-23 2001-05-01 The State Of Oregon Acting By And Through The State Board Of Higher Education On Behalf Of Oregon State University Natural antibrowning and antioxidant compositions and methods for making the same
US7759507B2 (en) * 2003-09-05 2010-07-20 Abbott Laboratories Lipid system and methods of use
US7344747B2 (en) * 2004-04-29 2008-03-18 Gfa Brands, Inc. Oxidative stabilization of omega-3 fatty acids in low linoleic acid-containing peanut butter
BRPI0512864B8 (pt) * 2004-07-01 2021-05-25 Johnson & Johnson Vision Care composição oftálmica, uso de pelo menos um ácido graxo ômega-6 e pelo menos um ácido graxo ômega-3 e método para preparar a referida composição
US7575768B2 (en) * 2005-09-07 2009-08-18 Brandeis University Dietary supplements and prepared foods containing triglyceride-recrystallized non-esterified phytosterols
CA2567879C (fr) * 2006-11-14 2013-03-26 Thomas Greither Compositions d'huile alimentaire nutritive et methodes pour les produire

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2968990A4 (fr) * 2013-03-15 2016-08-24 Nutramax Lab Inc Compositions comprenant du sulforaphane ou un précurseur de sulforaphane et un phytostérol ou un phytostanol

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