WO2019066887A1 - Teintures de flavonoïdes mélangées par lots et procédés de fabrication et d'infusion - Google Patents

Teintures de flavonoïdes mélangées par lots et procédés de fabrication et d'infusion Download PDF

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Publication number
WO2019066887A1
WO2019066887A1 PCT/US2017/054247 US2017054247W WO2019066887A1 WO 2019066887 A1 WO2019066887 A1 WO 2019066887A1 US 2017054247 W US2017054247 W US 2017054247W WO 2019066887 A1 WO2019066887 A1 WO 2019066887A1
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Prior art keywords
flavonoid
tincture
solvent
amount
resveratrol
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PCT/US2017/054247
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English (en)
Inventor
Kim A. POPEJOY
Jeffrey J. Keaffaber
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Heart Healthy Spirits, LLC
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Priority to PCT/US2017/054247 priority Critical patent/WO2019066887A1/fr
Publication of WO2019066887A1 publication Critical patent/WO2019066887A1/fr

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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/111—Aromatic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A61K31/05—Phenols
    • 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
    • A61K31/075—Ethers or acetals
    • A61K31/085—Ethers or acetals having an ether linkage to aromatic ring nuclear carbon
    • A61K31/09—Ethers or acetals having an ether linkage to aromatic ring nuclear carbon having two or more such linkages
    • 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
    • A61K31/12—Ketones
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/347—Phenols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/08—Solutions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
    • C12C5/00—Other raw materials for the preparation of beer
    • C12C5/02—Additives for beer
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12G—WINE; PREPARATION THEREOF; ALCOHOLIC BEVERAGES; PREPARATION OF ALCOHOLIC BEVERAGES NOT PROVIDED FOR IN SUBCLASSES C12C OR C12H
    • C12G2200/00—Special features
    • C12G2200/21—Wine additives, e.g. flavouring or colouring agents

Definitions

  • the present invention relates to methods to combine tinctures of bioavailable flavonoids and infuse them into beverages, foods, cosmetics, drugs, or even directly into the human or animal body.
  • the present invention further relates to methods for adding sufficient amount of flavonoid infused tinctures to provide sufficient and bioavailable amounts of homeopathic and anti-oxidative agents to a food, beverage, cosmetic or drug product, with minimal effect on the food, beverage, cosmetic or drug product's alcohol by volume (ABV).
  • ABSV alcohol by volume
  • Quercetin has become very popular because of the wide range of health benefits it offers in other areas including diabetes, cataracts, hay fever, peptic ulcer, schizophrenia, inflammation, asthma, gout, viral infections, chronic fatigue syndrome, preventing cancer and for treating chronic infections of the prostate.
  • Pterostilbene is found in almonds, vaccinium berries, and grape leaves and vines, but not in the actual grapes themselves and thus does not make their way into red wine. Quercetin is found in a variety of plants including red onion, radish, sweet potato, capers, fennel and more. Despite the high levels of flavonoids in many of these foods, studies have shown that the oral bioavailability is quite low and is rapidly cleared from the body. Because of the known antioxidant and anti-inflammatory health benefits as well as the support of the cardiovascular and nervous systems that comes from these flavonoids, a way to infuse them into food, beverage, cosmetic or drug products has become desired.
  • Flavonoids such as Resveratrol, Pterostilbene and quercetin have been found to have significant anti-oxidative effects on human metabolism and thus are believed to be efficacious in improving brain, heart, metabolic and other organ health. It has recently been confirmed that flavonoids such as resveratrol, pterostilbene, and quercetin in various combinations can act synergistically and additively. Thus, improving the benefits to human health over administering just a single flavonoid at a time.
  • flavonoid enhanced products simply include an amount of resveratrol or other flavonoid powder being added to the normal ingredients of the food or beverage since the resveratrol or other flavonoid powder adds very little to no flavor.
  • antioxidants are combined in powdered, capsuled, gelled or pilled form.
  • these powders are poorly soluble in water and thus, when ingested into the body, are minimally bioavailable and thus an inefficient way for the market to provide bioavailable flavonoids.
  • flavonoids included in a tincture to provide for a synergistic result from a mixture of flavonoids. It should be understood that by mixing two or more flavonoids first, then exposing the flavonoid mixture to a solvent will result in an imbalance of the flavonoids in solution. Thus where a particular concentration of two or more flavonoids is desired, simply adding two or more flavonoids, then adding a solvent, will not result in the desired bioavailable concentration of the selected flavonoids. One solution is to add additional solvent until all the flavonoids dissolve in solution, however, in some cases large amounts of solvents are undesirable, for instance ethanol, in this case, may begin to affect the alcohol by volume of the food or beverage to above lawful levels.
  • a tincture and a process for making the same, that includes two or more flavonoids, and that results in the desired concentration of the selected flavonoids.
  • certain flavonoids have a higher affinity for dissolving in a solvent or in a particular solvent.
  • ABSV alcohol by volume
  • a batch-mixed tincture of one or more individual tinctures created from mixing a flavonoid in a food grade or pharmaceutical grade solvent is provided.
  • the batch- mixed tincture is added to any food, beverage, cosmetic or drug for infusing a bioavailable dose of the desired flavonoid(s) to the food, beverage, cosmetic or drug.
  • a method of making the batch-mixed tincture is also provided by creating a particular mixture of a first flavonoid tincture and a second flavonoid tincture.
  • Acceptable flavonoids include, at least, resveratrol, pterostilbene, quercetin, procyanidin, curcumin or combinations thereof.
  • Acceptable food grade or pharmaceutical grade solvents include, at least, dimethyl sulfoxide (DMSO), 1-butanol [n-butanol], 1-propanol, cyclodextrins or ethanol. It is appreciated that other acceptable flavonoids and solvents are known in the art, and nothing herein is intended to limit such available flavonoids.
  • the batch-mixed tincture is used to infuse a bioavailable dose of flavonoid(s) into a food, beverage, cosmetic or drug product.
  • FIG. 1 is a representation of trans-resveratrol/Ethanol solution formed by mixing trans-resveratrol with pure ethanol.
  • FIG. 2 is a block diagram providing an example of at least one embodiment of the present invention illustrating the method of 201 weighing approximately 420 milligrams trans-resveratrol, 202 measuring an amount of solvent containing 10 milliliters of pharmacy grade ethanol, 203 dissolving the 201 trans-resveratrol powder in the 202 solvent and 205 providing a golden yellow tincture containing resveratrol dissolved in ethanol.
  • the solution is 204 passed through a 10 micron filter to remove any undissolved resveratrol and any other impurities or suspended solids contained in the solution.
  • the solution is 204 agitated to aide in the dissolving of the 201 trans-resveratrol powder in the 202 solvent containing at least 10 milliliters of ethanol.
  • FIG. 3 is a representation of pterostilbene/Ethanol solution formed by mixing pterostilbene with pure ethanol.
  • mixture shall mean a physical combination of two or more substances on which the identities are retained and are mixed but are not combined chemically.
  • food or “beverage” may alternatively be a food, beverage, cosmetic or drug product.
  • ethanol shall mean pure ethanol or a solvent containing a majority by weight of ethanol.
  • solvent shall mean ethanol (as defined above), DMSO, or other solvent known in the art that is not harmful to humans in small quantities.
  • tincture shall mean an alcohol concentrate along with other materials that is used as an additive for a food or beverage.
  • “flavonoid” shall mean those plant metabolites thought to provide health benefits through cell signaling pathways and antioxidant effects, including resveratrol, pterostilbene and quercetin.
  • non-alcoholic beverage shall mean a beverage having an alcoholic content by volume between 0.0% alcohol by volume (ABV) and 2.8% ABV. In some embodiments of the present invention, a “non-alcoholic beverage” is between 0.0% and 0.5% ABV.
  • alcoholic beverage shall mean any beverage with ABV content greater than that amount which is considered to be a non-alcoholic beverage.
  • resveratrol shall mean trans-resveratrol, cis-resveratrol, or dihydro-resveratrol.
  • Trans-resveratrol having the structure provided in formula (I):
  • quercetin shall mean quercetin having the structure provided in formula (II):
  • pterostilbene shall mean trans-pterostilbene having the structure provided in formula (III):
  • bioavailable shall mean the amount of a particular dose of a drug product that is available within the blood stream for absorption or metabolization.
  • bioavailable shall mean free trans-resveratrol and/or its conjugate forms or derivatives thereof available in a mixture or tincture.
  • flavonoid(s) shall mean resveratrol, quercetin, pterostilbene or combinations thereof.
  • the present invention provides a tincture which includes at least one flavonoid and solvent to be infused with a food, beverage, nutraceutical or cosmetic. It should be appreciated that by creating a flavonoid/solvent solution that a bioavailable dose of the flavonoid may be delivered to a subject orally. Without intending to be bound to a particular theory, it is believed that flavonoids, particularly resveratrol and pterostilbene, become hydrogen bonded upon making a solution with solvents, particularly ethanol or DMSO, in the present invention. The hydrogen bonded flavonoid can be added to any food or beverage and provide similar bioavailability as the tincture itself.
  • a tincture is made of a solution of a flavonoid, or a combination of flavonoids, immixed with a solvent where the tincture is a homogeneous (single-phase) solution with the flavonoid solute hydrogen bonded to the solvent.
  • a tincture of flavonoid and solvent is formed by mixing an amount of flavonoid with an amount of solvent to form a mixture and agitating the flavonoid and solvent mixture dissolving the flavonoid into solution.
  • the solvent used is of food grade or pharmacy grade ethanol or DMSO.
  • the ethanol or DMSO added to the tincture should be between 5% and 100% ethanol or DMSO.
  • the ethanol is at least 160 proof. In at least one embodiment of the present invention, the ethanol is 200 proof.
  • range is intended to encompass not only the end point values of the range but also intermediate values of the range as explicitly being included within the range and varying by the last significant figure of the range.
  • a recited range of from 1 to 4 is intended to include 1-2, 1-3, 2-4, 3-4, and 1-4.
  • the tincture may be added to a food or beverage. In at least one embodiment of the present invention, the tincture is added after all processing, distilling or heating has been performed on a food or beverage. In at least one embodiment of the present invention, the tincture is added to a food or beverage at the point of service of the food or beverage. In at least one embodiment, the tincture in encapsulated in a gel cap or immixed with a pharmaceutically acceptable carrier or gel and delivered as a pill or in a gel cap.
  • the tincture may be diluted with water.
  • a resveratrol concentration in a solvent of: a) 100% ethanol may be between 0 and 42 grams per liter of ethanol; b) 90% ethanol and 10% water may be between 0 and 32 grams per liter of ethanol; c) 80% ethanol and 20% water may be between 0 and 22 grams per liter of ethanol; d) 70% ethanol and 30% water is between 0 and 13 grams per liter of ethanol; e) 60% ethanol and 40% water is between 0 and 6.5 grams per liter of ethanol; 50% ethanol and 50% water is between 0 and 2.5 grams per liter of ethanol; f) 40% ethanol and 60% water is between 0 and 800 milligrams per liter of ethanol; g) 30% ethanol and 70% water is between 0 and 250 milligrams per liter of ethanol; h) 20% ethanol and 80 % water is between 0 and 70 milligrams per liter of liter of water.
  • the tincture may include one or more additional additives.
  • additional additives may be water, spices, vitamins and minerals, color additives, flavor additives, or combinations thereof.
  • spices may include pumpkin spice, cinnamon, sugar, sage, vanilla bean extract, or combinations thereof.
  • vitamins and minerals may include Thiamine hydrochloride, riboflavin (Vitamin B2), niacin, niacin amide, folate or folic acid, beta carotene, potassium iodide, iron or ferrous sulfate, alpha tocopherols, ascorbic acid, Vitamin D, amino acids (L- tryptophan, L-lysine, L-leucine, L-methionine), or combinations thereof.
  • color additives may include Orange B, Citrus Red No.
  • flavor additives may be vinegar, citric acid, tartaric acid, malic acid, fumaric acid, lactic acid, high fructose corn syrup, hydrolyzed proteins, artificial sweeteners, or food extracts.
  • the amount of flavonoid delivered in a tincture is to be of sufficient doses that are known to provide the health benefits associated with the selected flavonoid.
  • the flavonoid concentration is between 0.001 and 42 grams per liter of solvent. In at least one embodiment of the present invention, the flavonoid concentration is between 1 and 18 milligrams per liter of solvent. In at least one embodiment of the present invention, 1 to 100 milliliters of a 0.001 to 42 gram flavonoid per liter of solvent tincture is added to a 12 ounce beverage. In at least one embodiment 1 to 10 milliliters of the flavonoid tincture is added to a 12 ounce beverage.
  • bioavailable trans-resveratrol is equivalent to 10 - 25 servings of red wine, understanding that red wines have variable amounts of bioavailable trans-resveratrol.
  • Example 9 for instance, the red wine used for testing bioavailable trans-resveratrol was below the detection limits of the measuring device, while adding the inventive tincture provided 450 times more bioavailable resveratrol than what appeared in the red wine without the tincture.
  • the present invention provides for a method of infusing a tincture of ethanol and flavonoid in a food or beverage, with minimal effect on the alcohol content of the food or beverage.
  • Alternative solvents, such as DMSO may not have the same effects on alcohol content.
  • a tincture of solvent and flavonoid is prepared and added to a beverage, and allowed sufficient time for the tincture to infuse with the beverage.
  • the amount of tincture added to the beverage changes the amount of alcohol by volume (ABV) of the beverage between 0.01% and 1.0%. In at least one embodiment of the present invention, the amount of tincture changes the ABV of the beverage between 0.02% and 0.5%.
  • the beverage is a nonalcoholic beverage.
  • an amount of 10 milligram per liter tincture is added to a 12 ounce non-alcoholic beverage thus providing a bioavailable amount of flavonoid while minimally changing the alcohol by volume of the non-alcoholic beverage from 0.0% to 0.02%.
  • a 0.1 milliliter dose of tincture is added to a 12 ounce non-alcoholic beverage thus providing a bioavailable amount of flavonoid while minimally changing the alcohol by volume of the non-alcoholic beverage from 0.0% to 0.02%.
  • an amount of 100 milligram per liter tincture is added to a 12 ounce non-alcoholic beverage thus providing a bioavailable amount of flavonoid while minimally changing the alcohol by volume of the non-alcoholic beverage from 0.0% to 0.2%.
  • a 1 milliliter dose of tincture is added to a 12 ounce non-alcoholic beverage thus providing a bioavailable amount of flavonoid while minimally changing the alcohol by volume of the non-alcoholic beverage from 0.0% to 0.2%.
  • the beverage is an alcoholic beverage.
  • an amount of a 10 milligram per liter tincture is added to a 12 ounce alcoholic beverage thus providing a bioavailable amount of flavonoid while minimally changing the alcohol by volume of the alcoholic beverage from 5.0% to 5.02%.
  • a 0.1 milliliter dose of tincture is added to a 12 ounce alcoholic beverage thus providing a bioavailable amount of flavonoid while minimally changing the alcohol by volume of the alcoholic beverage from 5.0% to 5.02%.
  • an amount of a 100 milligram per liter tincture is added to a 12 ounce alcoholic beverage thus providing a bioavailable amount of flavonoid while minimally changing the alcohol by volume of the alcoholic beverage from 5.0% to 5.2%.
  • a 1.0 milliliter dose of tincture is added to a 12 ounce alcoholic beverage thus providing a bioavailable amount of flavonoid while minimally changing the alcohol by volume of the alcoholic beverage from 5.0% to 5.2%.
  • the tincture for a beverage infusion with 42 grams of flavonoid and a solvent containing 0% water and 100% solvent with a saturation of 42g/L In at least one embodiment a solution containing 42 grams of flavonoid in liter of solvent is passable through a 10 micron filter. In at least one embodiment the amount of bioavailable flavonoid present in a beverage containing the flavonoid tincture is 25 milligrams. In at least one embodiment 0.6 milliliters of tincture is added to a 355 milliliter (12 ounce) beverage to deliver a flavonoid dose of 25 milligrams. In at least one embodiment, the tincture for a food infusion is a solvent of 70% water and 30% ethanol, yielding 250 mg of flavonoid per liter of tincture.
  • flavonoids included in a tincture to provide for a synergistic result from a mixture of flavonoids. It should be understood that by mixing two or more flavonoids first, then exposing the flavonoid mixture to a solvent will result in an imbalance of the flavonoids in solution. Moreover, since solutions in the food and pharmaceutical industry are exposed to a filtration process, many of the intended flavonoids may be filtered out. Without being bound to any particular theory, it is believed that if a flavonoid is not appropriately dissolved or hydrogen bonded to the solvent, then it will remain undissolved, and thus likely will not become bioavailable. This is because certain flavonoids have a higher affinity for dissolving in a solvent, or certain solvents may be stronger solvents than others. As a result, simply mixing flavonoids then mixing with a solvent will likely not result in the desired flavonoid concentration intended.
  • a method of mixing an amount of one or more individual tinctures of flavonoids for making batch mixtures of specifically desired combinations of bioavailable flavonoids is provided.
  • the batch-mixture is intended for infusing a beverage, food, cosmetic or drug to provide a bioavailable dose of said flavonoids.
  • the tincture may be administered to a patient or animal directly by direct infusion into a body through known administration methods in the art, including without limit, intravenously, subcutaneously, intradermally, intramuscularly, sublingually, or any other method of parenterally delivered products and including products delivered through various feeding tubes.
  • the method includes creating a first flavonoid tincture by mixing an amount of a flavonoid with an amount of solvent and agitating the flavonoid and solvent mixture until said flavonoid is dissolved in the solvent, then creating a second flavonoid tincture by mixing an amount of a flavonoid with an amount of solvent and agitating the flavonoid and solvent mixture until said flavonoid is dissolved in the solvent.
  • the pre-mixing of the individual tinctures is believed to bond the desired fiavonoids to the solvent.
  • the method further includes mixing an amount of the first flavonoid tincture with the second flavonoid tincture to form a batch-mixed tincture solution.
  • the batch-mixed tincture results in the desired concentration of the bioavailable fiavonoids despite their differing affinities since the fiavonoids are dissolved and believed to be hydrogen bonded to the solvent, thus preventing a preferential dissolution of the fiavonoids for given solvents.
  • the first flavonoid tincture has a different flavonoid than the second flavonoid tincture. In at least one embodiment, the first flavonoid tincture has a different solvent than the second flavonoid tincture. In at least one embodiment, the amount of the first flavonoid tincture and the amount of the second flavonoid tincture to be mixed is determined by calculating the relative concentrations of the flavonoid in the tinctures and mixing the appropriate volumes of the respective tinctures to achieve the desired flavonoid concentrations in the batch-mixed tinctures.
  • the amount of the first flavonoid tincture and the amount of the second flavonoid tincture to be mixed is determined by calculating the relative alcohol by volume of the respective tinctures and mixing the appropriate volumes of the respective tinctures to achieve the desired alcohol by volume of the batch-mixed tincture. It should be appreciated that where different solvents are used, that in some embodiments the flavonoid used in the first and second flavonoid tincture may be the same flavonoid. Similarly, it should be appreciated that where different flavonoids are used, that in some embodiments the solvent used in the first and second flavonoid tincture may be the same solvent.
  • solvents used for making any tincture shall be pharmaceutical or food grade, but otherwise may be any solvent known in the art.
  • the solvent may include, without limit, ethanol, dimethyl sulfoxide (DMSO), 1-butanol [n-butanol], 1-propanol, cyclodextrins, or combinations thereof.
  • flavonoids used for making any tincture may be any flavonoid known in the art.
  • the flavonoid may include, without limit, resveratrol, pterostilbene, quercetin, procyanidin, curcumin, or combinations thereof.
  • the tinctures may not have been pre-filtered prior to making the batch-mixed tincture.
  • some amount of undissolved flavonoid, or some amount of precipitated flavonoid may separate from solution after the mixture of the first and second flavonoid tinctures.
  • the batch-mixed tincture solution is filtered after mixing in order to remove any undissolved flavonoid, any impurities, any other suspended solids, or combinations thereof.
  • the intent of the present invention is to provide a bioavailable dose of flavonoids to beverages, foods, cosmetics, or pharmaceuticals.
  • the flavonoid concentration of any flavonoid tincture is between 0.001 and 50 grams per liter of solvent.
  • the present invention further includes method for infusing the batch-mixed tinctures as previously described herein.
  • the batch-mixed tincture is added a food, beverage, cosmetic or drug product. It is appreciated that in some instances immediate application of the tincture to a food or beverage may provide a bioavailable dose, but in some embodiments it may be preferred to allow sufficient time for the tincture to infuse with the food, beverage, cosmetic or drug product.
  • This wait-time could be for a homogeneous mixture (or as near as one could be achieved) of the tincture within the food or cosmetic, or providing enough of a sufficient time for an amount of the tincture to distribute within the food or beverage to avoid the addition of the tincture from altering the taste of the food or beverage.
  • the present invention further provides a batch-mixed flavonoid tincture.
  • the batch-mixed tincture is created using the methods described herein.
  • the flavonoid concentration in a solvent of 5%-40% ethanol is between 1 and 800 milligrams per liter of ethanol.
  • the flavonoid concentration in a solvent containing 5% - 40% ethanol is between 1 and 800 milligrams per liter of ethanol.
  • the method or the tincture described herein may contain additional additives which are not flavonoids.
  • the tincture includes additional additives of water, spices, vitamins and minerals, color additives, flavor additives, pro-drugs, pharmaceuticals, nutraceuticals, or combinations thereof.
  • the method for making a batch-mixed tincture includes the step of adding to the individual tincture solutions additional additives of water, spices, vitamins and minerals, color additives, flavor additives, pro-drugs, pharmaceuticals, nutraceuticals, or combinations thereof.
  • a tincture of resveratrol and ethanol is made by immixing resveratrol and ethanol to provide 100 milligrams of resveratrol per liter of ethanol.
  • a beer containing 5.0% ABV is poured into a glass.
  • a direct measure of 0.1 mL dose of tincture is added to the 12 ounce beer. The added tincture raises the ABV of the beer to 5.02% while providing a bioavailable dose of resveratrol.
  • Example 1 is repeated, but instead using a high-end mega-dose of 1.0 mL of tincture raising the ABV of the beer with tincture to 5.2%.
  • a tincture of resveratrol and ethanol is made by immixing resveratrol and ethanol to provide 100 milligrams of resveratrol per liter of ethanol.
  • a 12 ounce glass of water is poured and a syringe is used to measure a 0.1 mL dose of tincture and is added to the 12 ounces of water.
  • the addition of the tincture raises the ABV of the water to 0.02% while providing a bioavailable dose of resveratrol.
  • Example 3 is repeated, but instead using a high-end mega-dose of 1.0 mL of tincture raising the ABV of the water with tincture to 0.2%.
  • FIG. 2 provides a method for making a tincture.
  • First 201 approximately 420 milligrams of trans-resveratrol powder is weighed.
  • Next 202 an amount of solvent containing 10 milliliters of pharmacy grade ethanol is measured, immixed and agitated with the 201 approximately 420 milligrams of trans-resveratrol powder.
  • the solution is agitated causing an amount of 203 the trans-resveratrol powder to dissolve in the solvent.
  • the mixed solution appears 205 golden yellow in color that contains 42 milligrams trans- resveratrol per milliliter of ethanol contained in the solvent.
  • Example 5 is repeated, but includes the additional step 204 of passing the solution through a 10 micron filter to remove any undissolved resveratrol and any other impurities contained in the resveratrol powder.
  • a tincture is made containing concentrated (near-saturated at 25°C) resveratrol and ethanol tinctures of 420 mg/10 mL (42.0 mg/mL). To deliver a 25 mg dose, 0.60 mL of tincture is required regardless of volume of beverage.
  • a tincture of trans-resveratrol with ethanol is prepared with food grade or pharmaceutical grade 180 to 200 proof ethanol. Observations under multiple environmental settings confirmed the stability of the tincture created. Using medical grade measuring devices, the tincture was added to various beverages in volumes necessary to replicate and exceed the amount of trans-resveratrol in a typical serving of red wine from the Mediterranean stock. Observations demonstrated that there was no precipitation, no change in color, no change in taste and calculations confirmed that the amount of increase in alcohol by volume was maintained below any regulatory standards for required reporting. EXAMPLE 9
  • trans-resveratrol tincture is prepared with food grade 200 proof ethanol.
  • the trans-resveratrol tincture is was prepared by adding 421.5 mg trans-resveratrol to 10 mL of 200 proof (100%) food grade ethanol. This resulted in a clear, golden-colored solution with concentration of 42.15 mg/mL.
  • a dose of 25 mg of trans-resveratrol is delivered to a serving volume of various drinks including red wine, white wine, beer (Yuengling), spirits such as vodka and bourbon (Jim Beam), energy drinks (5 Hour Energy), sodas (diet Coke, Coke, Sprite) and orange juice (Tropicana).
  • An amount of the trans- resveratrol tincture is added to each beverage and is calculated based on the volume of the serving.
  • the serving volume for a glass of wine is 187 mL.
  • the serving volume for spirits is 50 mL, resulting in 499.8 ug/mL of trans-resveratrol infused.
  • the serving volume is 57 mL, resulting in 439.1 ug/mL of trans-resveratrol infused.
  • a red wine blank was used as a control in order to show natural resveratrol being present in the beverage.
  • a syringe is used to transfer 0.6 mL of trans- resveratrol tincture to a serving volume of each beverage. The tincture is delivered to each serving volume below the surface of the liquid.
  • trans-resveratrol tincture appears to dissolve as a homogenous solution. All beverages receiving the tincture are thoroughly mixed, and a few milliliters of each are transferred to amber-colored sample vials. Samples are stored from each beverage in a refrigerator for analysis.
  • UV detection reveals higher trans-resveratrol concentrations than did MS/MS detection.
  • MS/MS detection focuses on the 228 mass number, resveratrol's molecular weight.
  • the percent recovery of free trans-resveratrol recovered in the vodka during analysis is 97.9% MS/MS and 109.9% UV, and in the bourbon is 116.9% MS/MS and 107% UV. It is appreciated that the percent recovery in some instances is greater than 100% because of +/- 17% error because of the techniques used to measure trans resveratrol. As a result these values can be considered to be 100% recovery in the vodka and bourbon beverages. These results show the bioavailability of the trans-resveratrol tincture added to beverages.
  • trans-resveratrol powder 25 mg is added to a serving volume of various drinks including red wine, white wine, beer (Yuengling), spirits such as vodka and bourbon (Jim Beam), energy drinks (5 Hour Energy), sodas (diet Coke, Coke, Sprite) and orange juice (Tropicana).
  • the trans-resveratrol appears to suspend in solution forming a cloudy layer. All beverages receiving the powder are thoroughly mixed. Each beverage is passed through a 10 micron filter to remove any undissolved resveratrol and any other impurities contained in the resveratrol powder. A few milliliters of each beverage are transferred to amber-colored sample vials. Samples are stored from each beverage in a refrigerator for analysis.
  • Examples 1 through 9 are repeated using the solvent DMSO and the flavonoid pterostilbene.
  • a tincture of pterostilbene and solvent is made by dissolving approximately
  • trans-pterostilbene powder into 10 mL of pharmacy grade ethanol.
  • a tincture of resveratrol, pterostilbene, and ethanol is made by combining separate volumes of tincture of resveratrol and tincture of pterostilbene in a range of the following volume resveratrol to volume pterostilbene ratios: 9: 1, 4: 1, 7:3, 3 :2, 1 : 1, 2:3, 3 :7, 1 :4, and 1 :9.
  • a 1.0 mL volume of the resulting tincture in Example 13 contains the following range of mg doses of resveratrol and pterostilbene respectively: 37.8, 4.2; 33.6, 8.4; 29.4, 12.6; 25.2, 16.8; 21.0, 21.0; 16.8, 25.2; 12.6, 29.4; 8.4, 33.6; and 4.2, 37.8.
  • a tincture of resveratrol, quercetin, and ethanol is made by dissolving 1.5 mg of quercetin powder into 1.0 mL of tincture of resveratrol. The resulting tincture contains 42 mg resveratrol and 1.5 mg quercetin.
  • a 100% saturated ethanol based tincture of R mixed 1 : 1 (equal volumes) with a 100%) saturated ethanol based tincture of Curcumin yields a batch -mixed tincture with 50 mg of Resveratrol and 10 mg of Curcumin per volume of tincture.
  • the batch- mixed tincture would yield a concentration of 25 mg/mL Resveratrol and 5 mg/mL Curcumin.
  • a 100% saturated ethanol based tincture of Resveratrol mixed 1 : 1 (equal volumes) with al00% saturated DMSO based tincture of Curcumin yields a batch-mixed tincture with 50 mg of Resveratrol and 25 mg of Curcumin per volume of tincture and a ratio of ethanol to DMSO of 1 : 1 by volume.
  • the batch-mixed tincture would yield a concentration of 25 mg/mL Resveratrol and 12.5 mg/mL Curcumin in the co-solvent (ethanol/DMSO) solution.
  • Combinations of Examples 17 and 18 will yield various ratios of resveratrol, curcumin, ethanol and DMSO, one combination being a tincture that yields a ratio of ethanol to DMSO of 3 : 1 by volume, and a ratio of resveratrol to curcumin of 100:35 by mass

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Abstract

L'invention concerne des procédés et des formulations pour le mélange par lots de teintures de flavonoïdes et l'infusion de la teinture mélangée par lot de flavonoïdes dans un aliment, une boisson, des produits cosmétiques ou médicamenteux avec un effet minimal ou nul sur l'alcool par volume du produit, et pour délivrer avec précision la concentration de mélange souhaitée des flavonoïdes. Une teinture de flavonoïdes mélangée par lots comprend une quantité d'au moins deux teintures de flavonoïdes individuelles, chaque teinture de flavonoïdes étant un mélange d'au moins un flavonoïde et d'un solvant. La teinture mélangée par lots est ajoutée à divers aliments et boissons, ou bien administrées directement à un être humain ou à un animal, pour obtenir une quantité biodisponible de flavonoïdes devant être absorbée et métabolisée par le corps fournissant des bénéfices de santé démontrés.
PCT/US2017/054247 2017-09-29 2017-09-29 Teintures de flavonoïdes mélangées par lots et procédés de fabrication et d'infusion WO2019066887A1 (fr)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2078802C1 (ru) * 1992-10-06 1997-05-10 Житомирский ликеро-водочный завод концерна "Укрспирт" Способ получения горькой настойки "житомирская ароматная"
WO2006099217A2 (fr) * 2005-03-10 2006-09-21 Unigen Pharmaceuticals, Inc. Formulation d'un melange de flavonoides et de flavanes a noyau b libre utilise comme agent therapeutique
US20160250157A1 (en) * 2014-08-02 2016-09-01 Heart Healthy Spirits, LLC Tincture For Infusing Flavonoids And Methods Of Use

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2078802C1 (ru) * 1992-10-06 1997-05-10 Житомирский ликеро-водочный завод концерна "Укрспирт" Способ получения горькой настойки "житомирская ароматная"
WO2006099217A2 (fr) * 2005-03-10 2006-09-21 Unigen Pharmaceuticals, Inc. Formulation d'un melange de flavonoides et de flavanes a noyau b libre utilise comme agent therapeutique
US20160250157A1 (en) * 2014-08-02 2016-09-01 Heart Healthy Spirits, LLC Tincture For Infusing Flavonoids And Methods Of Use

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