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WO2018185780A1 - Composition biodisponible pour oléorésine de curcuma - Google Patents

Composition biodisponible pour oléorésine de curcuma Download PDF

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Publication number
WO2018185780A1
WO2018185780A1 PCT/IN2018/050193 IN2018050193W WO2018185780A1 WO 2018185780 A1 WO2018185780 A1 WO 2018185780A1 IN 2018050193 W IN2018050193 W IN 2018050193W WO 2018185780 A1 WO2018185780 A1 WO 2018185780A1
Authority
WO
WIPO (PCT)
Prior art keywords
oil
turmeric
formulation
oleoresin
essential oil
Prior art date
Application number
PCT/IN2018/050193
Other languages
English (en)
Inventor
Nirvanashetty Somashekara
Sripathy RAViCHANDRAN
Nilima MOHANTY
Sanjib Kumar PANDA
Vivek Anand PARACHUR
Original Assignee
Olene Life Sciences Private Limited
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Olene Life Sciences Private Limited filed Critical Olene Life Sciences Private Limited
Publication of WO2018185780A1 publication Critical patent/WO2018185780A1/fr

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Classifications

    • 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
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/4841—Filling excipients; Inactive ingredients
    • A61K9/4858—Organic compounds
    • 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)
    • A61K36/906—Zingiberaceae (Ginger family)
    • A61K36/9066—Curcuma, e.g. common turmeric, East Indian arrowroot or mango ginger
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
    • 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
    • A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels

Definitions

  • the present invention relates to a turmeric liquid oleoresin formulation. More particularly, the present invention specifically discloses a synergistic, bioavailable and slow or sustained release formulation for turmeric liquid oleoresin and/or its components containing, an essential oil and an emulsifier.
  • Turmeric (Curcuma longa) has been used extensively as a spice, a nutraceutical, food colourant and as a pharmaceutical agent.
  • turmeric has been used for treatment of a variety of disorders, such as inflammation, indigestion, throat infections, common colds, or liver ailments, as well as topically, to cleanse wounds or treat skin sores.
  • Curcumin one of the major curcuminoids present in the turmeric is responsible for its health benefits.
  • Turmeric liquid oleoresin is generally poorly soluble in water. As result of low solubility in water the eventual plasma concentration of actives from turmeric oleoresin is significantly low after oral administrations and hence poor health benefits. Other factors contributing to such low plasma concentration may be poor absorption, rapid metabolism, and rapid systemic elimination. Overall the turmeric oleoresin shows a very low oral bioavailability for Curcumin and/or Curcuminoids.
  • CN200410036402 discloses use of a curcumin-phospholipid complex for improving bioavailability.
  • Co-pending Indian Patent Application N°6738/CHE/2015 of the current inventor suggests a use of tri-molecular complex containing a curcumin, a metal ion and a phospholipid for improving the bioavailability of Curcumin.
  • 950/CHE/2010 filed by Arjuna Natural Extracts Ltd. indicates a composition comprising a curcuminoid mixture comprising curcumin, desmethoxycurcumin and b is demethoxycur cumin, curcumin essential oil comprising Ar-turmerone, for increasing the bioavailability of curcumin.
  • WO 2015/025263 Another formulation for increasing bioavailability has been discussed in WO 2015/025263.
  • the formulation as disclosed in WO 2015/025263 mainly comprises of a curcumin mixture and a water extract both derived from turmeric.
  • the enhancement of bioavailability of the curcumin is achieved by a water-soluble protein 'turmerin' derived from turmeric.
  • emulsifier Another option for increasing the water-solubility of hydrophobic molecule, such as Curcumin, is use of an emulsifier.
  • the emulsifier tends to reduce the surface tension between the immiscible liquids thereby increasing the solubility of the liquids.
  • the property of emulsifiers has been extensively exploited by many pharmacists for improving the bioavailability of said hydrophobic molecules.
  • Emulsifiers are generally used in manufacture of Self Emulsifying Drug Delivery Systems (SEDDS).
  • turmeric liquid oleoresin formulation which comprises of turmeric liquid oleoresin and/or its components combined with an essential oil, other than turmeric essential oil, and an emulsifier.
  • the invention provides a bioavailable turmeric oleoresin formulation which consists of a turmeric liquid oleoresin, an essential oil other than turmeric essential oil and an emulsifier and is devoid of any added essential oil of turmeric.
  • the enhanced bioavailability is due to the synergistic activity of the essential oil and the emulsifier, wherein essential oil has a dual purpose of aiding in enhancing the bioavailability and also acting as co-solvent in the composition, thereby synergistic ally working with emulsifier to enhance the bioavailability.
  • said essential oil is not essential oil of turmeric.
  • the formulation of the invention demonstrates enhanced bioavailability and also achieves slow or sustained release of the turmeric oleoresin components.
  • Turmeric oleoresin contains resins from turmeric co extracted with other actives.
  • Fig. 1 illustrates graph indicating solubility and slow release of curcumin from the Turmeric oleoresin formulation of Composition ⁇ in Water.
  • Fig, 2 illustrates graph indicating solubility and slow release of curcumin from the Turmeric oleoresin formulation of Composition XII in Water.
  • Fig. 3 illustrates graph indicating solubility and slow release of curcumin from the Turmeric oleoresin formulation of Composition XIII in Water.
  • Fig. 4 illustrates the graph indicating solubility and slow release of curcumin from the formulation of Composition XIV in Water. Detailed Description of Invention:
  • the present invention describes a turmeric oleoresin formulation containing a turmeric liquid oleoresin, an essential oil other than turmeric essential oil and an emulsifier and devoid of any added essential oil of turmeric.
  • the enhanced bioavailability is due to the synergistic activity of the essential oil and the emulsifier, wherein essential oil has a dual purpose of aiding in enhancing the bioavailability by acting as co-solvent in the composition and directly enhancing the bioavailability as a permeation enhancer, thereby synergistic ally working with emulsifier to enhance the bioavailability of turmeric oleoresin components.
  • the herbal composition of the invention contains
  • turmeric liquid oleoresin and/or its components 1. 0.1 to 99.8% turmeric liquid oleoresin and/or its components
  • the said turmeric oleoresin is extracted from Curcuma species selected from, but not limited to, C. longa, C .xanthorriza, C. aeruginosa, C. amarissima, C. alismatifolia, C. aromatica, C. attenuate, C. bicolor, C. chuanyujin, C. comosa, C. elata, C. exigua, C. kwangsiensis, C. phaeocaulis, C. roscoeana, C. sichuanensis, C. thorelii, C. wenyujin, C. yunnanensis, C. zedoariaetc.
  • the essential oil can be selected from, but not limited to, Ginger essential oil, Cinnamon essential oil, Orange essential oil, Annua essential oil, Boswellia serrata oil, Cardamom oil, Chamomile oil, Citronella oil, Olibanum oil, Fennel oil, Garlic oil, Jojoba oil, Lemon oil, Lemongrass oil, Pepper oil, Myrrh oil, Nutmeg oil, Oregano oil, Rosemary oil, Tea tree oil, Mint oil, Cedar oil, Thyme oil, Wintergreen oil, Ylang ylang oil, Calendula oil, Eugenol (Clove oil), Lippia sidoides, Origanum dictamnus, Artemisia arborecens, etc. either alone or in combination.
  • the essential oil is not essential oil of turmeric or turmeric essential oil.
  • the essential oil is obtained by steam distillation or supercritical extraction or extraction using organic and inorganic solvents from plant, spice or other source.
  • the emulsifier present in the formulation of invention can be a natural emulsifier or synthetic emulsifier and their derivatives.
  • the natural emulsifier may be selected from, but not limited to, soya phospholipids, soya lecithin, soya lysolecithin, sunflower lecithin/phospholipids, sunflower lecithin, sunflower lysolecithin, phospholipids from plant/marine source, and egg phospholipids.
  • the synthetic polymer emulsifier may be selected from, but not limited to, Polysorbates and derivatives, polyethylene glycols and derivatives, glyceryl, glyceryl monooleates and derivatives, Brij-65, D-a-Tocopheryl Polyethylene glycol 1000 Succinate, etc. either alone or in combination.
  • the formulation of the invention sustains the release of the turmeric oleoresin components.
  • the slow or sustained release effect is achieved by maintaining the viscosity of the formulation in range of 1000 to 2500000 centipoise (at 25°C).
  • Suitable excipients may be added to achieve desired viscosity in the product.
  • the formulation of the invention is in semisolid or liquid form.
  • Said liquid or semisolid herbal composition can be formulated in the form of soft gelatine capsules, hard gelatine capsules, syrup, ointments, gels, patches, suspension, syrup, liquid sachets, bottles and/or any other suitable packing material.
  • the formulation may also contains suitable, permissible excipients such as, but not limited to, suitable diluents, viscosity enhancers, selected from, but not limited to, Olive oil, Gingili oil, Omega-3 fatty acids, Krill oil, Lard Oil, Salmon oil, Medium Chain Triglycerides, Microcrystalline cellulose, polyvinylpyrrolidone, Hydroxypropyl methylcellulose, Natural Gums, Synthetic gums, calcium silicate, silicon dioxide, silica, Magnesium stearate, antioxidants, preservatives, pH modifiers, acidifiers, viscosity modifiers etc.
  • suitable diluents selected from, but not limited to, Olive oil, Gingili oil, Omega-3 fatty acids, Krill oil, Lard Oil, Salmon oil, Medium Chain Triglycerides, Microcrystalline cellulose, polyvinylpyrrolidone, Hydroxypropyl methylcellulose, Natural Gums, Synthetic gums, calcium silicate, silicon dioxide, silica,
  • the formulation may also contains other plant extract, animal extract, liquid or semisolid or solid oleoresins, liquid or semisolid or solid oleo gum resins and liquid or semisolid or solid gum resins, including, but not limited to Clove Oleoresins, Curry leaf Oleoresins, Pepper Oleoresins, Cardamom Oleoresins, Chilli Oleoresins, Capsicum Oleoresins, Paprika Oleoresins, Ginger Oleoresins, Coleus Oleoresin, Milk Thistle Oleoresin.
  • Clove Oleoresins including, but not limited to Clove Oleoresins, Curry leaf Oleoresins, Pepper Oleoresins, Cardamom Oleoresins, Chilli Oleoresins, Capsicum Oleoresins, Paprika Oleoresins, Ginger Oleoresins, Coleus Oleoresin, Milk Thistle Oleoresin.
  • Terminalia arjuna Grifolia simplicifolia, Echinacea, Coriander Oleoresins, Cumin Oleoresins, Celery Oleoresins, Boswellia oleoresin/oleogumresin.
  • the formulation may also contains other purified natural or synthetic compounds selected from but not limited to group of flavonoids, phenolic compounds, terpene, resins, alkaloids, stilbenes, lignins.
  • Proanthocyanidins, and their metabolites/derivatives such as Boswellic acids, Bacosides, Lutein, Berberine, El!agie acid, ResveratroL Caiechin , quereitin, Gingerols, caffeine, Pterostilbene, AUicin, Astaxanthin, Siiymarin, Beta- cryptoxanthin, Daidzein, Geisseiii, hupericin, alkamides.
  • Omega 3 fatty acids Krill oil, L-DOPA, Huperizine A, etc. with the purity ranging from 0.1 to 99.9%.
  • the said formulation can be used as pharmaceutical, nutraceutical, dietary supplement, feed supplements/additives, food supplement/additives, beverage supplement, flavours, colouring agents, cosmetic formulations, special health supplement, food, gym supplements and other medicaments.
  • the composition of invention is useful in the prevention, management and treatment of animal and human disease such as bone disease, eye diseases, cancers, blood diseases, Gut health/Digestive health, Immune health, oral health and hygiene, metabolic syndrome, glucose health, Age Related Macular Degeneration (AMD), Glaucoma, joint health, Alzheimer's disease, depression, diabetes, CNS diseases, cardiovascular diseases, brain diseases, anti- aging, inflammatory diseases, weight management, hypercholesterolemia obesity, skin health, hair health, nail health, infectious diseases, injuries, sports nutrition etc.
  • animal and human disease such as bone disease, eye diseases, cancers, blood diseases, Gut health/Digestive health, Immune health, oral health and hygiene, metabolic syndrome, glucose health, Age Related Macular Degeneration (AMD), Glaucoma, joint health, Alzheimer's disease, depression, diabetes, CNS diseases, cardiovascular diseases, brain diseases, anti- aging, inflammatory diseases, weight management, hypercholesterolemia obesity, skin health, hair health, nail health, infectious diseases, injuries, sports nutrition etc.
  • the invention provides a process for manufacturing the formulation of the invention, the process comprises of following steps:
  • step (b) adding emulsifier to reaction mixtures of step (a) and mixing the same for 5 to 180 minutes at 30°C to 130°C to get uniform mixture and cool;
  • step (c) adding essential oil to mixture of step (b) at 30 to 80°C and mixing the reaction mixture to obtain a liquid/semisolid product;
  • step (e) mixing with optional antioxidants and preservatives to product of step (d) to obtain final product;
  • step (f) transferring the final product of step (e) into HDPE jerry cans or any suitable packaging material
  • Composition I is Composition I;
  • the formulation is prepared by the process comprising following steps:
  • turmeric liquid oleoresin was taken in a reaction vessel and, heated to 80°C for 30 minutes with continuous stirring;
  • step (b) Leeithin was added to reaction mixtures of step (a) and mixed for 30 minutes with continuous heating to get a uniform mixture and cooled to room temperature;
  • step (b) Ginger essential oil was added to the mixture of step (b) and mixed for 10 minutes have uniform mixture;
  • composition II Composition II:
  • the formulation is prepared by the process comprising following steps:
  • turmeric liquid oleoresin was taken in a reaction vessel and, heated to 80°C for 30 minutes with continuous stirring;
  • step (b) Ginger essential oil was added to the mixture of step (b) and mixed for 10 minutes have uniform mixture;
  • Composition III is a composition III:
  • the formulation is prepared by the process comprising following steps:
  • turmeric liquid oleoresin was taken in a reaction vessel and, heated to 90°C for 30 minutes with continuous stirring;
  • the formulation is prepared by the process comprising following steps:
  • turmeric liquid oleoresin was taken in a reaction vessel and, heated to 90°C for 30 minutes with continuous stirring;
  • Cinnamon essential oil was added to the mixture of step (b) and mixed for 10 minutes get uniform mixture;
  • the formulation is prepared by the process comprising following steps:
  • turmeric liquid oleoresin was taken in a reaction vessel and, heated to 90°C for 30 minutes with continuous stirring;
  • step (b) Nutmeg essential oil was added to the mixture of step (b) and mixed for 10 minutes get final product;
  • the formulation is prepared by the process comprising following steps:
  • turmeric liquid oleoresin was taken in a reaction vessel and, heated to 90°C for 30 minutes with continuous stirring;
  • step (b) Orange and Ginger essential oil was added to the mixture of step (b) and mixed for 10 minutes get final product; d) Final product was transferred to HDPE container for further processing
  • the formulation is prepared by the process comprising following steps:
  • turmeric liquid oleoresin was taken in a reaction vessel and, heated to 90°C for 30 minutes with continuous stirring;
  • Turmeric liquid oleoresin components 30.00 2. Orange oil 15.00
  • Total 100.00 lhc formulation is prepared by the process comprising following steps:
  • turmeric liquid oleoresin was taken in a reaction vessel and, heated to 90°C for 30 minutes with continuous stirring;
  • the formulation is prepared by the process comprising following steps:
  • turmeric liquid oleoresin was taken in a reaction vessel and, heated to 90°C for 30 minutes with continuous stirring;
  • the formulation was tested for its active ingredient solubility and release in water. 5Q0mg of product from composition IX was added into the water under intermittent stirring at 37°C. Samples were drawn for up to five hours and tested for active ingredient release by measuring absorbance at 424nm using UV-Vis spectrophotometer. Absorbance vs time graph was plotted as indicated in Fig. 1. Result indicates slow release of curcumin from the formulation into the water.
  • the formulation is prepared by the process comprising following steps:
  • turmeric liquid oleoresin was taken in a reaction vessel and, heated to 90°C for 30 minutes with continuous stirring;
  • step (b) Polysorbate was added to reaction mixtures of step (a) and mixed for 30 minutes with continuous heating to get a uniform mixture and cooled to room temperature;
  • step (b) Ginger essential oil was added to the mixture of step (b) and mixed for 10 minutes get uni orm mixture;
  • the formulation is prepared by the process comprising following steps:
  • step (b) Orange and Ginger essential oil was added to the mixture of step (b) and mixed for 10 minutes get uniform mixture;
  • the formulation is prepared by the process comprising following steps:
  • turmeric liquid oleoresin was taken in a reaction vessel and, heated to 90°C for 30 minutes with continuous stirring;
  • Hie formulation was tested for its active ingredient solubility and release in water. 500mg of product from composition XII was added into the water under intermittent stirring at 37°C. Samples were drawn for up to five hours and tested for active ingredient release by measuring absorbance at 424nm using UV-Vis spectrophotometer. Absorbance vs time graph was plotted as indicated in Fig. 2. Result indicates slow release of cureumin from the formulation into the water.
  • Composition XIII
  • the formulation is prepared by the process comprising following steps:
  • turmeric liquid oleoresin was taken in a reaction vessel and, heated to 90°C for 30 minutes with continuous stirring;
  • step (b) Thyme essential oil was added to the mixture of step (b) and mixed for 10 minutes get uniform mixture;
  • the formulation was tested for its active ingredient solubility and release in water. 500mg of product from composition XIII was added into the water under intermittent stirring at 37°C. Samples were drawn for up to five hours and tested for active ingredient release by measuring absorbance at 424nm using UV-Vis spectrophotometer. Absorbance vs time graph was plotted as illustrated in Fig. 3. Result indicates slow release of curcumin from the formulation into the water.
  • the formulation is prepared by the process comprising following steps:
  • turmeric liquid oleoresin was taken in a reaction vessel and, heated to 90°C for 30 minutes with continuous stirring;
  • step (b) Thyme essential oil was added to the mixture of step (b) and mixed for 10 minutes get uniform mixture;
  • composition XIV was added into the water under intermittent stirring at 37°C. Samples were drawn for up to five hours and tested for active ingredient release by measuring absorbance at 424nm using UV-Vis spectrophotometer. Absorbance vs time graph was plotted as illustrated in Fig. 4. Result indicates slow release of curcumin from the formulation into the water.
  • the formulation is prepared by the process comprising following steps: a) turmeric liquid oleoresin was taken in a reaction vessel and, heated to 90 C for 30 minutes with continuous stirring;
  • step (b) Polysorbate-80 was added to reaction mixture of step (a) and mixed for 30 minutes with continuous heating to get a uniform mixture and cooled to room temperature;
  • step (b) Thyme essential oil was added to the mixture of step (b) and mixed for 10 minutes get uniform mixture;
  • the formulation was tested for its active ingredient solubility and release in water. 500mg of product from composition XV was added into the water under intermittent stirring at 37°C. Samples were drawn for up to five hours and tested for active ingredient release by measuring absorbance at 424nm using UV-Vis spectrophotometer. Absorbance vs time graph was plotted as illustrated in Fig. 5. Result indicates slow release of curcumin from the formulation into the water.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
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  • Oil, Petroleum & Natural Gas (AREA)
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Abstract

La présente invention concerne une formulation biodisponible pour oléorésine liquide de curcuma. La formulation selon l'invention comprend une oléorésine liquide de curcuma dans une plage de 0,1 à 99,8 %; une huile essentielle, autre que l'huile essentielle de curcuma, dans une plage de 1 à 98 %, et un émulsifiant dans la plage de 1 à 98 %. La formulation de l'invention présente en outre une biodisponibilité améliorée et une libération lente ou prolongée des composants oléorésine de curcuma.
PCT/IN2018/050193 2017-04-04 2018-04-04 Composition biodisponible pour oléorésine de curcuma WO2018185780A1 (fr)

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IN201741012081 2017-04-04

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WO2018185780A1 true WO2018185780A1 (fr) 2018-10-11

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022115063A1 (fr) * 2020-11-30 2022-06-02 Kavak Çi̇ftci̇ Gida İçecek Organi̇k Gübre Sanayi̇ Ve Ti̇caret Li̇mi̇ted Şi̇rketi̇ Composition d'un complément alimentaire et son procédé de production
US20220273570A1 (en) * 2019-10-18 2022-09-01 Quicksilver Scientific, Inc. Self-Microemulsifying Multi-Deliverable Systems

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3906116A (en) * 1972-09-25 1975-09-16 Bush Boake Allen Ltd Concentrated oleoresin products and emulsification process for preparing them
WO2006129323A1 (fr) * 2005-05-30 2006-12-07 Antony Benny Composition destinee a ameliorer la biodisponibilite du curcumin
US20160166516A1 (en) * 2014-12-11 2016-06-16 Designs For Health, Inc. Novel curcuminoid formulations and related methods of treatment

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3906116A (en) * 1972-09-25 1975-09-16 Bush Boake Allen Ltd Concentrated oleoresin products and emulsification process for preparing them
WO2006129323A1 (fr) * 2005-05-30 2006-12-07 Antony Benny Composition destinee a ameliorer la biodisponibilite du curcumin
US20160166516A1 (en) * 2014-12-11 2016-06-16 Designs For Health, Inc. Novel curcuminoid formulations and related methods of treatment

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20220273570A1 (en) * 2019-10-18 2022-09-01 Quicksilver Scientific, Inc. Self-Microemulsifying Multi-Deliverable Systems
CN115038430A (zh) * 2019-10-18 2022-09-09 快饮科学公司 自微乳化的多种可递送物的系统
EP4045012A4 (fr) * 2019-10-18 2023-11-15 Quicksilver Scientific, Inc. Systèmes multi-livrables auto-microémulsifiants
WO2022115063A1 (fr) * 2020-11-30 2022-06-02 Kavak Çi̇ftci̇ Gida İçecek Organi̇k Gübre Sanayi̇ Ve Ti̇caret Li̇mi̇ted Şi̇rketi̇ Composition d'un complément alimentaire et son procédé de production

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