WO2022018162A1 - FORMULATIONS D'UNE NOUVELLE FORME CRISTALLINE DE β-CRYPTOXANTHINE, PROCÉDÉS POUR LEUR PRÉPARATION ET LEURS UTILISATIONS - Google Patents

FORMULATIONS D'UNE NOUVELLE FORME CRISTALLINE DE β-CRYPTOXANTHINE, PROCÉDÉS POUR LEUR PRÉPARATION ET LEURS UTILISATIONS Download PDF

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Publication number
WO2022018162A1
WO2022018162A1 PCT/EP2021/070441 EP2021070441W WO2022018162A1 WO 2022018162 A1 WO2022018162 A1 WO 2022018162A1 EP 2021070441 W EP2021070441 W EP 2021070441W WO 2022018162 A1 WO2022018162 A1 WO 2022018162A1
Authority
WO
WIPO (PCT)
Prior art keywords
cryptoxanthin
weight
range
crystal form
formulation
Prior art date
Application number
PCT/EP2021/070441
Other languages
English (en)
Inventor
Grace BAAKLINI
Carlo Ronco
Christian Schaefer
Bernd Schlegel
Elodie VERDURAND
Christa Luise VOECKLER
Bettina Wuestenberg
Céline Sophie Charlotte FANTOU
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 WO2022018162A1 publication Critical patent/WO2022018162A1/fr

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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
    • 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
    • A23L33/15—Vitamins
    • 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
    • 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
    • A61K31/07—Retinol compounds, e.g. vitamin A
    • 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
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1617—Organic compounds, e.g. phospholipids, fats
    • A61K9/1623—Sugars or sugar alcohols, e.g. lactose; Derivatives thereof; Homeopathic globules

Definitions

  • Starch hydrolysates are classified according to their dextrose equivalents. “Dextrose” is a synonym for “glucose”.
  • the term “dextrose equivalent” (DE) denotes the degree of hydrolysis and is a measure of the amount of reducing sugar calculated as D-glucose based on dry weight; the scale is based on native starch having a DE close to 0 and glucose having a DE of 100.
  • the dried formulation according to the present invention comprises preferably 0.1 to 30.0 weight-%/0.3 to 25.0 weight-%, more preferably 0.5 to 20.0 weight-%, even more preferably 0.7 to 15.0 weight-%/0.8 to 10.0 weight-%, most preferably 1.0 to 7.0 weight-%, of crystal form I of b-cryptoxanthin, based on the total weight of the dried formulation.
  • 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% to 10%, preferably in a range of from 0.5% to 4%, more preferably in a range of from 3% to 4%.
  • OSA-starches are also known under the expression “modified food starch”.
  • glycerophospholipids are phosphatidic acid, bisphosphatidic acid, lecithin (phosphatidylcholine), phosphatidylethanolamine, phosphatidylmethyl- ethanolamine, phosphatidylserine, phosphatidylinositol, phosphatidylglycerol, and diphosphatidylglycerol (cardiolipin), as well as products containing any of these above and derived from plants such as soy bean, corn, peanut, rape seed, wheat, or the like, products containing any of the above and derived from egg yolk or an animal such as cattle, and various lecithins derived from microorganisms such as Escherichia coli.
  • lecithin phosphatidylcholine
  • phosphatidylethanolamine phosphatidylmethyl- ethanolamine
  • phosphatidylserine phosphatidylinositol
  • phosphatidylglycerol
  • the hydrogenation may be performed by allowing lecithin to react with hydrogen in the presence of a catalyst, whereby the unsaturated bond of the fatty acid moiety is hydrogenated.
  • the hydrogenation improves the stability of lecithin against oxidation.
  • the hydroxylation may be performed by heating lecithin together with high concentrations of hydrogen peroxide and an organic acid such as acetic acid, tartaric acid, or butyric acid, in which the unsaturated bond of the fatty acid moiety is hydroxylated. The hydroxylation improves the hydrophilicity of lecithin.
  • Preferred saponins are those from Quillaja.
  • the total amount of the anti-oxidant (especially DL-a-tocopherol or mixed tocopherols) in the aqueous dispersion is preferably in the range of from 0.1 to 10 weight-%, more preferably in the range of from 0.2 to 2 weight-%, most preferably in the range of from 0.3 to 1.5 weight-%, based on the total weight of the aqueous dispersion.
  • Formulations A to D are spray-dried powders; formulation E is an aqueous dispersion.
  • the pre-cursors of the spray-dried formulations A to D, i.e. the corresponding aqueous dispersions are also preferred embodiments of the present invention.
  • the water content of the dispersed suspension is adjusted to 66%.
  • the suspension is kept at 40°C under stirring.
  • Spray drying is performed with a NIRO Mobile MINOR 2000 Typ D1 device by rotary atomization with a nozzle air pressure of 2.0 bar, with inlet air temperature of 180°C ,and outlet air temperature of max. 96°C. Particle size distribution of the powder is measured by laser diffraction.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Mycology (AREA)
  • Polymers & Plastics (AREA)
  • Food Science & Technology (AREA)
  • Nutrition Science (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Botany (AREA)
  • Biophysics (AREA)
  • Molecular Biology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

L'invention concerne des formulations d'une nouvelle forme cristalline de β-cryptoxanthine, des procédés pour leur préparation et leurs utilisations, ainsi que des produits adaptés à la consommation humaine comprenant de telles formulations.
PCT/EP2021/070441 2020-07-22 2021-07-21 FORMULATIONS D'UNE NOUVELLE FORME CRISTALLINE DE β-CRYPTOXANTHINE, PROCÉDÉS POUR LEUR PRÉPARATION ET LEURS UTILISATIONS WO2022018162A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP20187284.3 2020-07-22
EP20187284 2020-07-22

Publications (1)

Publication Number Publication Date
WO2022018162A1 true WO2022018162A1 (fr) 2022-01-27

Family

ID=71783832

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2021/070441 WO2022018162A1 (fr) 2020-07-22 2021-07-21 FORMULATIONS D'UNE NOUVELLE FORME CRISTALLINE DE β-CRYPTOXANTHINE, PROCÉDÉS POUR LEUR PRÉPARATION ET LEURS UTILISATIONS

Country Status (2)

Country Link
TW (1) TW202211807A (fr)
WO (1) WO2022018162A1 (fr)

Citations (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004037236A1 (fr) 2002-10-25 2004-05-06 KEMIN FOODS, L. C. d/b/a KEMIN HEALTH, L. C. Promoteur d'osteogenese contenant $g(b)-cryptoxanthine en tant qu'ingredient actif
WO2005110122A1 (fr) 2004-05-18 2005-11-24 Dsm Ip Assets B.V. Utilisation de $g(b)-cryptoxanthine
WO2006053761A2 (fr) 2004-11-19 2006-05-26 Dsm Ip Assets B.V. Gommes naturelles modifiees pour preparations de principes actifs
WO2008045405A2 (fr) 2006-10-12 2008-04-17 Kemin Industries, Inc. Biosynthèse de bêta-cryptoxanthine
WO2008079287A1 (fr) 2006-12-20 2008-07-03 Kemin Foods, L.C. Procédé d'amélioration de la santé cardiovasculaire
WO2008110225A1 (fr) 2007-03-15 2008-09-18 Dsm Ip Assets B.V. Compositions de caroténoïdes contenant de la gomme arabique modifiée
US20090093015A1 (en) 2007-10-09 2009-04-09 Kemin Foods, L.C. Beta-cryptoxanthin production using a novel lycopene beta-monocyclase gene
US20090311761A1 (en) 2008-06-13 2009-12-17 Frederick Khachik Process for Synthesis of (3S)- and (3R)-3-Hydroxy-Beta-Ionone, and Their Transformation to Zeaxanthin and Beta-Cryptoxanthin
WO2011039336A1 (fr) 2009-10-02 2011-04-07 Dsm Ip Assets B.V. Nouveau conjugué de gomme végétale et d'amidon alimentaire modifié sous la forme d'émulsifiant pour ingrédients liposolubles
WO2012059286A1 (fr) 2010-11-03 2012-05-10 Dsm Ip Assets B.V. Compositions à base de caroténoïdes contenant de la gomme arabique modifiée par de l'anhydride octénylsuccinique
WO2014115037A2 (fr) 2013-01-24 2014-07-31 Omniactive Health Technologies Ltd. Bêta-cryptoxanthine provenant d'une source végétale et un procédé pour sa préparation
WO2014186683A1 (fr) 2013-05-16 2014-11-20 University Of Maryland, College Park Procédé pour une transformation en enceinte unique directe de lutéine en β-cryptoxanthine par son ester acétate
WO2015089385A1 (fr) 2013-12-12 2015-06-18 Kemin Industries, Inc. Produits de soins d'hygiène personnelle contenant des extraits de lanterne chinoise (physalis alkekengi)
WO2016157157A1 (fr) 2015-04-02 2016-10-06 Omniactive Health Technologies Limited Méthodes de prévention et de traitement du syndrome cardiométabolique et compositions utilisées pour ces dernières
WO2016174600A1 (fr) 2015-04-27 2016-11-03 Omniactive Health Technologies Limited Compositions à base de bêta-cryptoxanthine, ses procédés de préparation et ses utilisations
CN111346059A (zh) 2020-04-17 2020-06-30 山东天音生物科技有限公司 水溶性隐黄质的制备方法

Patent Citations (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004037236A1 (fr) 2002-10-25 2004-05-06 KEMIN FOODS, L. C. d/b/a KEMIN HEALTH, L. C. Promoteur d'osteogenese contenant $g(b)-cryptoxanthine en tant qu'ingredient actif
WO2005110122A1 (fr) 2004-05-18 2005-11-24 Dsm Ip Assets B.V. Utilisation de $g(b)-cryptoxanthine
WO2006053761A2 (fr) 2004-11-19 2006-05-26 Dsm Ip Assets B.V. Gommes naturelles modifiees pour preparations de principes actifs
WO2008045405A2 (fr) 2006-10-12 2008-04-17 Kemin Industries, Inc. Biosynthèse de bêta-cryptoxanthine
WO2008079287A1 (fr) 2006-12-20 2008-07-03 Kemin Foods, L.C. Procédé d'amélioration de la santé cardiovasculaire
WO2008110225A1 (fr) 2007-03-15 2008-09-18 Dsm Ip Assets B.V. Compositions de caroténoïdes contenant de la gomme arabique modifiée
US20090093015A1 (en) 2007-10-09 2009-04-09 Kemin Foods, L.C. Beta-cryptoxanthin production using a novel lycopene beta-monocyclase gene
US20090311761A1 (en) 2008-06-13 2009-12-17 Frederick Khachik Process for Synthesis of (3S)- and (3R)-3-Hydroxy-Beta-Ionone, and Their Transformation to Zeaxanthin and Beta-Cryptoxanthin
WO2011039336A1 (fr) 2009-10-02 2011-04-07 Dsm Ip Assets B.V. Nouveau conjugué de gomme végétale et d'amidon alimentaire modifié sous la forme d'émulsifiant pour ingrédients liposolubles
WO2012059286A1 (fr) 2010-11-03 2012-05-10 Dsm Ip Assets B.V. Compositions à base de caroténoïdes contenant de la gomme arabique modifiée par de l'anhydride octénylsuccinique
WO2014115037A2 (fr) 2013-01-24 2014-07-31 Omniactive Health Technologies Ltd. Bêta-cryptoxanthine provenant d'une source végétale et un procédé pour sa préparation
WO2014186683A1 (fr) 2013-05-16 2014-11-20 University Of Maryland, College Park Procédé pour une transformation en enceinte unique directe de lutéine en β-cryptoxanthine par son ester acétate
WO2015089385A1 (fr) 2013-12-12 2015-06-18 Kemin Industries, Inc. Produits de soins d'hygiène personnelle contenant des extraits de lanterne chinoise (physalis alkekengi)
WO2016157157A1 (fr) 2015-04-02 2016-10-06 Omniactive Health Technologies Limited Méthodes de prévention et de traitement du syndrome cardiométabolique et compositions utilisées pour ces dernières
WO2016174600A1 (fr) 2015-04-27 2016-11-03 Omniactive Health Technologies Limited Compositions à base de bêta-cryptoxanthine, ses procédés de préparation et ses utilisations
CN111346059A (zh) 2020-04-17 2020-06-30 山东天音生物科技有限公司 水溶性隐黄质的制备方法

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
"Modified Starches: Properties and Uses", 1986, CRC PRESS, INC.
D. E. LOEBER ET AL., J. CHEM. SOC. C, vol. 404, 1971
F. KHACHIK ET AL., SYNTHESIS, vol. 3, 2011, pages 509 - 516
R. KUHNC. GRUNDMANN, CHEMISCHE BERICHTE, 1933, pages 1746 - 1750
RICHARD KUHN ET AL: "Über Kryptoxanthin, ein Xanthophyll der Formel C40H56O (Über das Vitamin des Wachstums, V. Mitteil.)", CHEMISCHE BERICHTE, 1 January 1933 (1933-01-01), pages 1746 - 1750, XP055759209, DOI: 10.1002/cber.19330661126 *
XIN WEN ET AL., JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 65, 2017, pages 6140 - 6151

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