WO2019121517A1 - Formules en poudre - Google Patents

Formules en poudre Download PDF

Info

Publication number
WO2019121517A1
WO2019121517A1 PCT/EP2018/085208 EP2018085208W WO2019121517A1 WO 2019121517 A1 WO2019121517 A1 WO 2019121517A1 EP 2018085208 W EP2018085208 W EP 2018085208W WO 2019121517 A1 WO2019121517 A1 WO 2019121517A1
Authority
WO
WIPO (PCT)
Prior art keywords
solid formulation
curcuminoids
present
starch
solid
Prior art date
Application number
PCT/EP2018/085208
Other languages
English (en)
Inventor
Andrea Hitzfeld
Christa Luise ROLKE
Christian Schaefer
Dirk Oliver WOERNE
Thomas Zwick
Original Assignee
Dsm Ip Assets B.V.
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 Dsm Ip Assets B.V. filed Critical Dsm Ip Assets B.V.
Publication of WO2019121517A1 publication Critical patent/WO2019121517A1/fr

Links

Classifications

    • 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
    • A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
    • A23L5/40—Colouring or decolouring of foods
    • A23L5/42—Addition of dyes or pigments, e.g. in combination with optical brighteners
    • A23L5/43—Addition of dyes or pigments, e.g. in combination with optical brighteners using naturally occurring organic dyes or pigments, 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 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
    • A23L2/58—Colouring agents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
    • A23P10/00—Shaping or working of foodstuffs characterised by the products
    • A23P10/30—Encapsulation of particles, e.g. foodstuff additives

Definitions

  • the present invention relates to a new and improved solid (powderous) formulation, which comprises a high amount of curcuminoids.
  • Curcuminoids are found in the turmeric plant.
  • Turmeric Curcuma longa
  • Turmeric Curcuma is a rhizomatous herbaceous perennial plant of the ginger family, Zingiberaceae.
  • the plant is native to the Indian Subcontinent and Southeast Asia.
  • the turmeric powder which consists of approximately 60-70% carbohydrates, 6- 13% water, 6-8% protein, 5-10% fat, 3-7% dietary minerals, 3-7% essential oil, s, 2-7% dietary fiber, and 1-6% curcuminoids, is very often used in any kind of formulations. (K.M. Nelson et al, J. Med, Chem. 2017, 60, 1620 - 1637). It is used as such or in a formulation.
  • curcuminoids in turmeric powder is very low (between 1 - 6 %).
  • the curcuminoids are the following group of compounds of formulae (I), (G), (II) and (III):
  • the compounds of formulae (I) and (G), which are tautomers, are called curcumin and they are the main components of the curcuminoids and present in an amount of 60 - 80%.
  • the compound of formula (II), which name is demethoxycurcumin is present in an amount of 15 - 27% and the compound of formula (III), which name is bisdemethoxycurcumin is present in an amount of 2 - 15%.
  • the exact composition can vary a lot.
  • curcuminoid or curcuminoids is always related to the mixture of the 4 different compounds of formula (I), (I’), (II) and (III) as disclosed above. As stated the terms curcuminoid or curcuminoids is always related to the mixture of the 4 different compounds of formula (I), (I’), (II) and (III) as disclosed above. As stated the
  • the main component of the mixture of the curcuminoid is curcumin (present in its keto- or enol-form) is a bright yellow compound in its powderous form.
  • the color of the curcuminoids is pH dependent (yellow at acidic pH, under alkaline conditions soluble and red).
  • the curcuminoids (as well as the turmeric powder) is used as herbal supplement (Ayurvedic medicine), dietary supplement, cosmetics ingredient, food flavoring, and food coloring.
  • As a food additive for gold-orange coloring its E number is E100.
  • curcuminoids Due to its relevance (especially in food coloring), there is always a need to provide improved formulations of curcuminoids. An important aim was to obtain high concentrated and nevertheless storage stable formulations of curcuminoids.
  • the present invention relates to a solid formulation of curcuminoids, wherein the content of the curcuminoid is at least 10 wt-%, based on the total weight of the solid formulation.
  • the solid formulation according to the present invention is very storage as such (in its powder form) as well has very nice properties when used as coloring ingredient in liquid (or gel-like) application forms.
  • the present invention relates to a solid formulation (SF) comprising
  • the content of the curcuminoid is usually 10 - 30 wt-%, based on the total weight of the solid formulation (preferably 10 - 25 wt-%).
  • the present invention relates to a solid formulation (SF1 ), which is the solid formulation (SF), comprising 10 - 30 wt-%, based on the total weight of the solid formulation (preferably 10 - 25 wt-%) of curcuminoid.
  • the curcuminoids are available as an extract from the turmeric plant from various suppliers (e.g. BioActives Europe GmbH). Most of these extracts have content of the curcuminoids of over 90 %.
  • the solid formulation comprises 70 wt-% - 90 wt-%, preferably 75 - 90 wt-%, based on the total weight of the solid formulation, of at least one protective colloid.
  • the present invention relates to a solid formulation (SF2), which is the solid formulation (SF) or (SF1 ), comprising 10 - 30 wt-%, based on the total weight of the solid formulation (preferably 10 - 25 wt-%) of at least one protective colloid.
  • the protective colloids in the formulations of the present invention are modified starches or mixtures of modified starches with sugars such as sucrose.
  • the present invention relates to a solid formulation (SF3), which is the solid formulation (SF), (SF1 ) or (SF2), wherein the protective colloids are modified starches or mixtures of modified starches with sugars such as sucrose.
  • SF3 solid formulation
  • the protective colloids are modified starches or mixtures of modified starches with sugars such as sucrose.
  • modified starches In contrast to starches (non-modified starches) which are hydrophilic and therefore do not have emulsifying capacities, modified starches do have emulsifying capacities.
  • Modified starches are e.g. made from starches substituted by known chemical methods with hydrophobic moieties. For example, starch may be treated with cyclic dicarboxylic acid anhydrides such as succinic anhydrides, substituted with a hydrocarbon chain (see O. B. Wurzburg (editor), "Modified Starches: Properties and Uses, CRC Press, Inc. Boca Raton, Fla., 1986 (and subsequent editions).
  • a particularly preferred modified starch of this invention has the following formula
  • St is a starch
  • R is an alkylene radical
  • R' is a hydrophobic group.
  • R is a lower alkylene radical such as dimethylene or trimethylene.
  • R' may be an alkyl or alkenyl group, preferably having 5 to 18 carbon atoms.
  • a preferred compound of formula (I) is an "OSA-starch” (starch sodium octenyl succinate).
  • the degree of substitution, i.e. the number of esterified hydroxyl groups to the number of free non-esterified hydroxyl groups usually varies in a range of from 0.1 percent to 10 percent, preferably in a range of from 0.5 percent to 4 percent, more preferably in a range of from 3 percent to 4 percent.
  • the present invention relates to a solid formulation (SF4), which is the solid formulation (SF), (SF1 ), (SF2) or (SF3), wherein the protective colloid is a modified starch of formula
  • St is a starch
  • R is an alkylene radical
  • R' is a hydrophobic group.
  • OSA-starch denotes any starch (from any natural source such as corn, waxy maize, waxy corn, wheat, tapioca and potato or synthesized) that was treated with octenyl succinic anhydride (OSA).
  • the degree of substitution i.e. the number of hydroxyl groups esterified with OSA to the number of free non-esterified hydroxyl groups usually varies in a range of from 0.1 percent to 10 percent, preferably in a range of from 0.5 percent to 4 percent, more preferably in a range of from 3 percent to 4 percent.
  • OSA-starches are also known under the expression "modified food starch".
  • OSA-starches may contain further hydrocolloids, such as starch, maltodextrin, carbohydrates, gum, corn syrup etc. and optionally any typical emulsifier (as co- emulsifier), such as mono- and diglycerides of fatty acids, polyglycerol esters of fatty acids, lecithins, sorbitan monostearate, and plant fibre or sugar.
  • emulsifier as co- emulsifier
  • OSA-starches encompasses also such starches that are commercially available from various suppliers under the tradenames such as HiCap 100, Capsul, Capsul HS, Purity Gum 2000, UNI-PURE, HYLON VII or C * EmCap.
  • modified starches and "OSA-starches” encompass further also modified starches/OSA-starches that were partly hydrolysed enzymatically, e.g. by glycosylases (EC 3.2; see http://www.chem.qmul.ac.uldiubmb/enzyme/EC3.2/) or hydrolases, as well as to modified starches/OSA-starches that were partly hydrolysed chemically by know methods.
  • modified starches and “OSA-starches” encompass also modified starches/OSA-starches that were first partly hydrolysed enzymatically and afterwards additionally hydrolysed chemically.
  • hydrolyse starch (either enzymatically or chemically or both) and then to treat this partly hydrolysed starch with cyclic dicarboxylic acid anhydrides such as succinic anhydrides, substituted with a hydrocarbon chain, preferably to treat it with octenyl succinic anhydride.
  • cyclic dicarboxylic acid anhydrides such as succinic anhydrides, substituted with a hydrocarbon chain
  • novel formulations of this invention may further contain adjuvants and/or excipients such as one or more of a mono- di-, oligo- or polysaccharide, a triglyceride, a water-soluble antioxidant, a fat-soluble antioxidant, humectants such as glycerol, sorbitol, polyethylene glycol, propylene glycol, extenders and solubilizers., silicic acid, Ca-silicate, Ca-carbonate and water. Therefore, the present invention relates to a solid formulation (SF5), which is the solid formulation (SF), (SF1 ), (SF2), (SF3) or (SF4), wherein solid formulation further comprises at least one adjuvant and/or at least one excipient.
  • adjuvants and/or excipients such as one or more of a mono- di-, oligo- or polysaccharide, a triglyceride, a water-soluble antioxidant, a fat-soluble antioxidant, humectant
  • the present invention relates to a solid formulation (SF5’), which is the solid formulation (SF5), wherein the at least oneadjuvant and/or at least one excipients is chosen from the group consisting of mono- di-, oligo- or polysaccharide, triglyceride, water-soluble antioxidant, fat-soluble antioxidant, humectants, extenders, solubilizers., silicic acid, Ca-silicate, Ca-carbonate and water.
  • Examples of mono- and disaccharides which may further be present in the formulations of the present invention are saccharose, invert sugar, glucose, fructose, xylose, lactose and maltose.
  • Examples of oligo- or polysaccharides which may further be present in the compositions of the present invention are xanthan gum, acacia gum, OSA modified acacia gum, pectins, guar, caroub gums, alginates, celluloses, cellulose derivatives like carboxymethylcellulose, starch, modified starch and starch hydrolysates, such as dextrins and maltodextrins, especially such in the range of 5- 65 dextrose equivalents (hereinafter: DE) and glucose syrup, especially such in the range of 20-95 DE.
  • DE dextrins and maltodextrins
  • the term“dextrose equivalent” (DE) denotes the degree of hydrolysation and is measure for the amount of reducing sugar calculated as D
  • the triglyceride is suitably a vegetable oil or fat, such as corn oil, sunflower oil, soybean oil, safflower oil, rape seed oil, peanut oil, arachis oil, palm oil, palm kernel oil, cotton seed oil or cocos oil.
  • the water-soluble antioxidant may be ascorbic acid and salts thereof, e.g., sodium ascorbate, and the like.
  • the fat-soluble antioxidant may be a tocopherol, e.g., dl-a- tocopherol (i.e., synthetic tocopherol), d-a-tocopherol (i.e., natural tocopherol), b- and g-tocopherol and mixtures thereof; ascorbic acid esters of fatty acids such as ascorbyl palmitate or stearate; butyl hydroxy toluene (BHT); butyl hydroxy anisol (BHA); propyl gallate; or t-butyl hydroxy quinoline.
  • the curcuminoids in the formulation according to the present invention usually have an average particle size below 5miti.
  • the present invention relates to a solid formulation (SF6), which is the solid formulation (SF), (SF1 ), (SF2), (SF3), (SF4), (SF5) or (SF5’), wherein the curcuminoids in the formulation have an average particle size (Dv50) below 5m ⁇ ti.
  • the average particle size (Dv50) is from 100nm to 5m ⁇ ti (preferably from 100nm - 1 pm)
  • the present invention relates to a solid formulation (SF7), which is the solid formulation (SF), (SF1 ), (SF2), (SF3), (SF4), (SF5), (SF5’) or (SF6), wherein the curcuminoids in the formulation have an average particle size (Dv50) of from 100nm to 5pm (preferably from 100nm - 1 pm).
  • the overall size and the shape of the particle of the solid formulation are not relevant for the invention. The same applies for the shape of the particles of the curcuminoids.
  • the solid formulations (SF), (SF1 ), (SF2), (SF3), (SF3’), (SF4), (SF5), (SF5’), (SF6) and (SF7) are produced using well-known production technology, such as spray drying, granulation, agglomeration. As stated above these formulations are (as such) storage stable for a long time (months). This means that the content of curcuminoids is not decreasing significantly.
  • the solid formulations (SF), (SF1 ), (SF2), (SF3), (SF3’), (SF4), (SF5), (SF5’), (SF6) and (SF7) can be used as such or in any kind of application forms. They can be mixed into an application form or also used as a part of a coating system (such as the coating of a chocolate lens)
  • the solid formulations (SF), (SF1 ), (SF2), (SF3), (SF3’), (SF4), (SF5), (SF5’), (SF6) and (SF7) are used in food products, feed products, dietary supplements, personal care and/or pharmaceutical products.
  • the solid formulations (SF), (SF1 ), (SF2), (SF3), (SF3’), (SF4), (SF5), (SF5’), (SF6) and (SF7) are used in the production of food products, feed products, dietary supplements, personal care and/or pharmaceutical products.
  • a preferred embodiment of the present invention is the use of at least one solid formulation SF), (SF1 ) (SF2), (SF3), (SF3’), (SF4), (SF5), (SF5’), (SF6) and/or (SF7) in a non-pasteurised beverage.
  • Another preferred embodiment of the present invention is the use of at least one solid formulation SF), (SF1 ), (SF2), (SF3), (SF3’), (SF4), (SF5), (SF5’), (SF6) and/or (SF7) in a coating of a chocolate lens.
  • the present invention also related to food products, feed products, dietary supplements, personal care and/or pharmaceutical products comprising at least one solid formulations (SF), (SF1 ), (SF2), (SF3), (SF3’), (SF4), (SF5), (SF5’), (SF6) and (SF7).
  • SF solid formulations
  • the amount of the solid formulation in any of the above-mentioned application forms depends on the application as well as of the concentration of the curcuminoids in the solid formulations. It can very a lot.
  • a further important aspect of the present invention is that the formulations according to the present invention are resulting in very stable application forms. These applications forms do have good properties regarding light stability.
  • the following examples illustrate the present invention.
  • the matrix was prepared by dispersing the modified starch (E1450, E1442), sucrose, maltodextrin and gum arabic in deionized water at 65 °C for at least 1 hour.
  • the curcumin extract (Curcuma Longa extract from BioActives Europe GmbH) was added and dispersed, resulting in a raw suspension.
  • Raw suspension was run through a laboratory ball mill (Dispermat SL 12 M1 , VMA-Getzmann GmbH) in circulation mode for 4 hours.
  • Sodium ascorbate or ascorbic acid were added to the milled suspension and if needed pH was lowered to 3.5 by use of sulfuric acid.
  • milled suspension was spray dried with a laboratory spray dryer (Mobile Minor, GEA Niro).
  • spray dried powder was granulated with a lab scale fluid bed processor (Type WFP-Mini, DMR Rothtechnologie GmbH).
  • All of these solid formulations can comprise a small amount of water (due to its production process). The content is less than 5 wt-%.
  • An adequate amount of the formulation is dispersed (to obtain a 5 ppm concentration), dissolved and/or diluted in/with water by use of ultrasonic in a water bath of 50 to 55°C.
  • the resulting "solution” is diluted to a final concentration of the fat-soluble active ingredient of 10 ppm and its UV/VIS-spectrum is measured against water as reference. From the resulting UV/VIS spectrum the absorbance at the specified wavelength of maximum or shoulder, Amax, is determined. Furthermore, the absorbance at 650 nm, A650, is determined.
  • the so formulated soft drink was tested in a light box as well as in a suntester
  • a soft drink was prepared (base formulation above) with a content of 10ppm of curcuminoids
  • the most realistic way to assess the quality of a soft drink is to mimic supermarket conditions with artificial light and day/night rhythm. Therefore, the soft drinks beverages were stored at room temperature under controlled light conditions in a light box.
  • the light box was set up by employing the following parameters:
  • a soft drink was prepared (base formulation above) with a content of 10ppm of curcuminoids.
  • formulations according to the present invention show excellent properties and stabilites.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicinal Preparation (AREA)

Abstract

La présente invention concerne une nouvelle formule solide (en poudre) améliorée, qui comprend une quantité élevée de curcuminoïdes.
PCT/EP2018/085208 2017-12-20 2018-12-17 Formules en poudre WO2019121517A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP17208945.0 2017-12-20
EP17208945 2017-12-20

Publications (1)

Publication Number Publication Date
WO2019121517A1 true WO2019121517A1 (fr) 2019-06-27

Family

ID=60954708

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2018/085208 WO2019121517A1 (fr) 2017-12-20 2018-12-17 Formules en poudre

Country Status (1)

Country Link
WO (1) WO2019121517A1 (fr)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101703490A (zh) * 2009-11-13 2010-05-12 杭州师范大学 聚多糖/无机纳米粒子杂化微纳米载药胶囊
WO2014191556A1 (fr) * 2013-05-30 2014-12-04 Chr. Hansen A/S Procédé de coloration de poudres permettant de préparer des aliments
US20160243240A1 (en) * 2005-06-30 2016-08-25 Basf Se Preparation in the form of a powder containing at least one carotenoid, at least one modified starch, and sucrose
EP3072400A1 (fr) * 2015-03-26 2016-09-28 DSM IP Assets B.V. Nouvelle couleur pour boissons
WO2017168006A1 (fr) * 2016-04-01 2017-10-05 Dsm Ip Assets B.V. Boissons comprenant des granules stables de lutéine broyée

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20160243240A1 (en) * 2005-06-30 2016-08-25 Basf Se Preparation in the form of a powder containing at least one carotenoid, at least one modified starch, and sucrose
CN101703490A (zh) * 2009-11-13 2010-05-12 杭州师范大学 聚多糖/无机纳米粒子杂化微纳米载药胶囊
WO2014191556A1 (fr) * 2013-05-30 2014-12-04 Chr. Hansen A/S Procédé de coloration de poudres permettant de préparer des aliments
EP3072400A1 (fr) * 2015-03-26 2016-09-28 DSM IP Assets B.V. Nouvelle couleur pour boissons
WO2017168006A1 (fr) * 2016-04-01 2017-10-05 Dsm Ip Assets B.V. Boissons comprenant des granules stables de lutéine broyée

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
"Modified Starches: Properties and Uses", 1986, CRC PRESS, INC.
K.M. NELSON ET AL., J. MED, CHEM., vol. 60, 2017, pages 1620 - 1637

Similar Documents

Publication Publication Date Title
JP5122485B2 (ja) β−カロテンを含有する組成物
JP5364894B2 (ja) 変性アカシアガムを含有するカロテノイド組成物
Peanparkdee et al. Physicochemical stability and in vitro bioaccessibility of phenolic compounds and anthocyanins from Thai rice bran extracts
US8597642B2 (en) Tablettable formulations of lipophilic health ingredients
KR101202607B1 (ko) 영양 보조제의 조절된 방출을 위한 방법 및 조성물
JP2010193890A (ja) 蛋白質−多糖類複合体を含む脂溶性有効成分の組成物
JP7388608B2 (ja) ルテインおよび／またはゼアキサンチンの新規の錠剤化可能な製剤
Patel et al. Development of microencapsulated anthocyanin-rich powder using soy protein isolate, jackfruit seed starch and an emulsifier (NBRE-15) as encapsulating materials
T Barcia et al. Bioactive compounds, antioxidant activity and percent composition of jambolão fruits (Syzygium cumini)
US20220071237A1 (en) Beverages comprising stable granules of milled lutein
Hui et al. Bioactive compounds from blueberry and blackcurrant powder alter the physicochemical and hypoglycaemic properties of oat bran paste
TW201703644A (zh) 包含胭脂木酯的酸穩定飲品
Vergara et al. Encapsulation of phenolic compounds through the complex coacervation technique for the enrichment of diet chewable candies
EP3054788A1 (fr) Colorant rouge pour boissons, aliments et compositions pharmaceutiques
dos Santos et al. Bioavailability of blackberry pomace microcapsules by using different techniques: An approach for yogurt application
US20130281550A1 (en) Carotenoid compositions containing octenyl succinate anhydride-modified gum acacia
KR102386185B1 (ko) 유아용 식품 제형에 적합한 루테인 조성물
WO2019121517A1 (fr) Formules en poudre
US20140199396A1 (en) Process for the manufacture of a powder containing lutein
TW201639469A (zh) 用於飲品之新顏色
Marpaung et al. Effect of sucrose on pH and thermal stability of anthocyanin, total phenolic content, and antioxidant activity of senduduk (Melastoma malabathricum) fruit extract
Vigh et al. Spectrophotometric analysis of plum jams
Robert Canales et al. The Encapsulation of Anthocyanins from Berry-Type Fruits. Trends in Foods

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 18816091

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 18816091

Country of ref document: EP

Kind code of ref document: A1