WO1998004636A1 - Obtencion de derivados solidos de curcumina - Google Patents
Obtencion de derivados solidos de curcumina Download PDFInfo
- Publication number
- WO1998004636A1 WO1998004636A1 PCT/ES1997/000187 ES9700187W WO9804636A1 WO 1998004636 A1 WO1998004636 A1 WO 1998004636A1 ES 9700187 W ES9700187 W ES 9700187W WO 9804636 A1 WO9804636 A1 WO 9804636A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- solution
- curcumin
- water
- resin
- acid
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B61/00—Dyes of natural origin prepared from natural sources, e.g. vegetable sources
-
- 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
Definitions
- the present invention relates to a process for obtaining a yellow, water-soluble and stable dye, both in aqueous and powder solution, which can be used in animal and human feed.
- the procedure contemplates the use of a natural product, such as curcumin resin, and another water-soluble natural product with abundant hydroxyl groups, such as polyethylene glycol, a chain of glycerin units, or starch.
- the procedure is to stir the curcumin resin in liquid medium at a temperature below 100 ° C for five to ninety minutes, in the presence of the other natural compound.
- the dye is obtained from the solution cooled to room temperature.
- the stability can be adjusted during preparation in order to direct the dye to some applications, where the stability of the dye is important, or to others where the color intensity is important.
- a curcumin resin released from oils is used by any of the methods in the literature, such as for example crystallization in organic solvent or preferably purification in supercritical fluid (PCT / ES97 / 00015 ).
- PCT / ES97 / 00015 purification in supercritical fluid
- the vehicle is a polyethylene glycol of molecular weight preferably between 4,000 and 6,000, with a melting point below 85 ° C.
- the curcumin resin is completely dissolved in the molten polyethylene glycol, the proportion being by weight between the curcumin resin and the active organic oxygen of the polyethylene glycol less than 1:20, preferably close to 1: 600.
- the solution is stirred for a few minutes, keeping the temperature between 70 ° C and 80 ° C.
- the solution is allowed to cool in an anhydrous environment and the resulting material is subjected to conditions that provide the solid in an industrially manageable form, for example in the form of granules, flakes, or dust, for which the machine is used. corresponding that the current technique facilitates, for example a grinder if desired in powder form.
- the resulting solid product is soluble in water without generating turbidity, has not lost any amount of the main raw material that is curcumin resin, is not contaminated by any decomposition by-product, and is of a strong clean yellow color.
- the vehicle is a starch.
- the curcumin resin is dissolved in an alkaline aqueous solution of pH 11-14 previously heated to 30-40 ° C. To this solution is added another 10% to 20% starch in water.
- the weight ratio of curcumin resin to starch is between 1: 1 to 1:50.
- the solution is stirred at the indicated temperature for 5 to 90 minutes, after that It is acidified to pH between 8 and 5.
- the acid to be used may be a food grade inorganic acid, such as phosphoric, hydrochloric or sulfuric acid, or an organic acid, such as citric or acetic acid.
- the precipitate obtained is filtered and dried in an oven at 40 ° C. Once dry, it is milled until the desired particle size is achieved for its application.
- This variant allows to design the characteristics of the final solid, to adapt it to the physical and chemical conditions of a large number of matrices among which are various foods, beverages, pharmaceuticals, and others.
- matrices among which are various foods, beverages, pharmaceuticals, and others.
- temperatures and pH products with high chromatic stability can be reached for the effect of temperature and light, which makes them especially interesting for applications in pastry and catering, or with high coloring power especially interesting for refreshing or pickled drinks.
- the dye obtained according to the present variant is of greater dyeing capacity, greater light stability, and greater storage stability than if obtained by the methods of the literature. Measurements are made according to methods in the usual literature. In addition, the quantitative yield increases.
- Example 1 0.518 g of curcumin resin, obtained according to the procedure in PCT / ES07 / 00015, is dissolved in 21 g of 6,000 molecular weight polyethylene glycol previously melted at 78 ° C. The mixture is maintained at that temperature and under stirring during A time of 8 minutes. After the stirring time, let the paste solidify in anhydrous atmosphere. 21.5 g of a water-soluble solid dye are obtained.
- Example 2. 3.0007 g of water-soluble starch are dissolved in 18.8 ml of water at 40 ° C. 0.6 ml of 40% sodium hydroxide (w / v) are added, homogenized and then 1,0005 g of curcumin resin obtained according to the procedure in PCT / ES07 / 00015. The mixture is stirred for 60 minutes, maintaining the pH between 12 and 12.5 and the temperature between 40 ° C. and 45 ° C.
- the resulting paste is allowed to dry in an oven at 40 ° C for 48 to 72 hours, obtaining 3.4 g of water-soluble yellow solid product.
- the dried product was kept in a controlled atmosphere oven at 60 ° C and 90% humidity for 30 calendar days. As a result, the product lost 28.6% of its chromatic activity and also partially lost its water solubility capacity, since 221 ppm solutions have permanent turbidity even after heating at 40-50 ° C.
- Example 3 3.0007 g of water-soluble starch are dissolved in 18.8 ml of water at 40 ° C. 0.6 ml of 40% sodium hydroxide (w / v) are added, homogenized and then 10002 g of curcumin resin obtained according to the procedure in PCT / ES07 / 00015. The mixture is stirred for 60 minutes, maintaining the pH between 12 and 12.5 and the temperature between 40 ° C. and 45 ° C.
- the resulting paste is allowed to dry in an oven at 40 ° C for 48 to 72 hours, obtaining 4.4 g of water-soluble yellow solid product.
- the dried product was kept in a controlled atmosphere oven at 60 ° C and 90% humidity for 30 calendar days. As a result, the product lost 28.6% of its chromatic activity and also partially lost its water solubility capacity, since 221 ppm solutions have permanent turbidity even after heating at 40-50 ° C.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Medicinal Preparation (AREA)
- Non-Alcoholic Beverages (AREA)
Abstract
Description
Claims
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU36238/97A AU3623897A (en) | 1996-07-25 | 1997-07-23 | Production of solid derivatives of curcumine |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES09601654A ES2121539B1 (es) | 1996-07-25 | 1996-07-25 | Procedimiento para la obtencion de un colorante alimentario estable a base de curcumina. |
ES09601653A ES2121538B1 (es) | 1996-07-25 | 1996-07-25 | Procedimiento para la obtencion de un colorante alimentario a base de curcumina. |
ESP9601654 | 1996-07-25 | ||
ESP9601653 | 1996-07-25 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1998004636A1 true WO1998004636A1 (es) | 1998-02-05 |
Family
ID=26154982
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/ES1997/000187 WO1998004636A1 (es) | 1996-07-25 | 1997-07-23 | Obtencion de derivados solidos de curcumina |
Country Status (3)
Country | Link |
---|---|
AU (1) | AU3623897A (es) |
CA (1) | CA2230895A1 (es) |
WO (1) | WO1998004636A1 (es) |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0037204A1 (en) * | 1980-03-27 | 1981-10-07 | General Foods Corporation | A dry stabilized curcumin-colorant additive |
US4475919A (en) * | 1980-04-28 | 1984-10-09 | Colorcon, Inc. | Colored medicinal tablet, natural color pigment and method for using the pigment in coloring food, drug and cosmetic products |
US4683256A (en) * | 1980-11-06 | 1987-07-28 | Colorcon, Inc. | Dry edible film coating composition, method and coating form |
DE4026118A1 (de) * | 1989-08-17 | 1991-02-21 | Kalamazoo Holdings Inc | Curcumin-komplexe |
-
1997
- 1997-07-23 WO PCT/ES1997/000187 patent/WO1998004636A1/es active Application Filing
- 1997-07-23 CA CA002230895A patent/CA2230895A1/en not_active Abandoned
- 1997-07-23 AU AU36238/97A patent/AU3623897A/en not_active Abandoned
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0037204A1 (en) * | 1980-03-27 | 1981-10-07 | General Foods Corporation | A dry stabilized curcumin-colorant additive |
US4475919A (en) * | 1980-04-28 | 1984-10-09 | Colorcon, Inc. | Colored medicinal tablet, natural color pigment and method for using the pigment in coloring food, drug and cosmetic products |
US4683256A (en) * | 1980-11-06 | 1987-07-28 | Colorcon, Inc. | Dry edible film coating composition, method and coating form |
DE4026118A1 (de) * | 1989-08-17 | 1991-02-21 | Kalamazoo Holdings Inc | Curcumin-komplexe |
Also Published As
Publication number | Publication date |
---|---|
AU3623897A (en) | 1998-02-20 |
CA2230895A1 (en) | 1998-02-05 |
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