CA2112277A1 - Crocetin-containing coloring - Google Patents
Crocetin-containing coloringInfo
- Publication number
- CA2112277A1 CA2112277A1 CA002112277A CA2112277A CA2112277A1 CA 2112277 A1 CA2112277 A1 CA 2112277A1 CA 002112277 A CA002112277 A CA 002112277A CA 2112277 A CA2112277 A CA 2112277A CA 2112277 A1 CA2112277 A1 CA 2112277A1
- Authority
- CA
- Canada
- Prior art keywords
- crocetin
- cyclodextrin
- colorant
- inclusion complex
- mixture
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
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
Abstract
ABSTRACT OF THE DISCLOSURE
A stabilized crocetin-containing colorant which has as an effective component a crocetin included by cyclodextrin.
This colorant is imparted with resistance against light and various chemicals to crocetin, which is a hydrolysate of crocin, the main component of the carotenoid gardenia yellow pigment. The colorant may be added to various food products for use of crocetin as a stable coloring matter.
A stabilized crocetin-containing colorant which has as an effective component a crocetin included by cyclodextrin.
This colorant is imparted with resistance against light and various chemicals to crocetin, which is a hydrolysate of crocin, the main component of the carotenoid gardenia yellow pigment. The colorant may be added to various food products for use of crocetin as a stable coloring matter.
Description
2 :~ .L rJ 2 7 7 I
CROCETIN-CONTAINING COLORING
~ield of the Invention The present invention relates to a crocetin-containing colorant, and specifically it relates to a crocetin-containing 1~' colorant which has been stabilized bY forming an inclusion I complex with cyclodextrin. Crocetin is a derivative of a yellow pigment found in plants such as gardenia and the like, and according to the present invention it is stabilized to ;~
widen the range of its use as a colorant.
. ~
~ Description of the Prior Art ~ `
~..
A method is known for stabilizing gardenia pigment (crocin) bY its inclusion complex with cYclodextrin (Japanese Patent Publication No.60-45229), but no method has been heretofore known for the stabilization of crocetin for its use as a pigment, which is an obiect of the Present invention.
~ Crocetin is a hydrolysate of crocin, the main component ¦ of the carotenoid gardenia yellow pigment, and it is ~ particularly unstable with resPeCt to light and chemicals.
¦ Methods have been proposed to improve its properties, such as I adding low concenSrations of ascorbic acid thereto, but the ¦ methods of use thereof are placed under strict control, and furthermore at present satisfactorY results cannot be obtained.
21~ ~,277 _mmar~ of the Invention An object of the present invention is to impart to crocetin resistance against li~ht and chemicals for its stability, thus providing a method for its use as a colorant.
The present invention provides a colorant consisting essentially of crocetin included by cyclodextrin.
The present invention also provides a process for producing the colorantt which comprises adding an aqueous alkaline solution of crocetin to a water paste of the cyclodextrin, and stirring to resulting mixture.
The present invention further provides a food or beverage colored by the colorant.
Brief Description of the Drawin~s Fi~ure 1 is a graph showing the results oi a light fastness test against fluorescent light.
Figure 2 is a qraph showing the results of a light ~-fastness test against ultraviolet light.
Detailed Description of the Invention Crocetin is obtained by hydrolyzing crocin, which is extracted from the above mentioned plant, but commercially available products (for example, products of Sigma, Inc.) may be -used.
Also, cyclodextrin (hereunder sometimes abbre~iated to "CD") is a cyclic oligosaccharide with a polymerization degree of 6-8 which is obtained by allowing cyclodextrin glucanotransferase (CGTase, EC 2.4.1.19) to act on starch or a hydrolysate thereof, and rpeclflc exarplee tùereof lnclude ~ -CD and r1xtures , "A ~
~J l ~ ~, 2 7 J) thereof, or mixtures of these and dextrin. Accordlng to the present invention, ~-CD alone and substances containing it are particularly suitable.
A crocetin-containing colorant according to the present invention may be obtained in the following manner.
First, a prescribed amount of crocetin which has been dissolved in an alkaline solution containing sodium hydroxidP, etc. is added to CD, particularly a--CD, which has been kneaded into a paste form with a small amount of water, and the mixture is vigorously stirred. The amount of water used is enough to form a stirrable paste, and in the case of a~CD, it may be added so that the solid concentration is about 40-60%. The stirring time will depend on the degree of stirring, but it is 10 minutes to 3 hours, and normally 60 minutes or more, and stirring may be effected while cooling so that the temperature does not rise too much over 80C.
After completion of the stirring, the pasty pigment which exists as an inclusion complex wlth CD is subjected to centrifugal separation (7,900 x G, 10 minutes, room temperature) to separate the non-lncluded pigment. The preclpitation portion obtained upon centrifugal separation is called a crocetin included by CD (hereunder sometimes shortened to "crocetin~CD inclusion complex") and this is used as the colorant according to the present invention.
The colorant according to the present invention may be used for coloring a wide variety of foods and beverages. For example, a refreshment beverage containing a sugar and a fruit ? s 1 't~'~;`)7 ~ J.~
juice (such as lemon juice) can be effectively colored by the colorant. Similarly, a fondant containing a sugar and starch may be effectively colored by the colorant. Further, a candy generally made of a sugar may be effectively colored by the colorant according to the present invention. The amount of the colorant varies widely depending upon various factors.
Exam~les A detailed description of the present invention will now be provided with reference to the Examples.
3a 2 ~ 7 7 ~ i Test Example 1 One part bY weight of crocetin dissolved in 0.1 M sodium hydroxide was added to 10 Parts by weight of a -CD 10 which had been prepared into a paste form with a small amount of water, and the mixture was vigorously stirred for 60 minutes and then subiected to centrifugal separation to obtain a -~
crocetin/ a -CD inclusion complex.
This crocetin included bY a -CD. ~ -CD. a mixture of a -. ~ - and ~ -CD (trade name: K-100. product of Ensuiko Sugar -Refining Co., Ltd.~. or a mixture of a -. ~ -CD and dextrin (trade name: K-50. product of Ensuiko Sugar Refining Co., Ltd.) and unprocessed crocetin were each dissolved in a Mcllvaine buffer solution (pH 7) containing 20% ethanol which had been diluted to 1/10 so that the absorbance at 420 nm and 450 nm was 0.4-0.8. to prePare test solutions.
A pre-determined amount of each of the test solutions was poured into a glass test tube and allowed to stand at room temperature under a fluorescent lamp at 900 lux. and the absorbance and the color difference were measured with time.
The results are shown in Eig. 1. As is clear from the figure. crocetin faded uPon exposure to fluorescent light.
but the fading was considerably supPressed with crocetin/ a -CD
inclusion complex. crocetin/ ~ -inclusion complex. croce~in/K-50 inclusion comPlex and crocetin/K-100 inclusion complex.
Test Example 2 The test solutions in Test Example 1 were poured onto '~ :
~ ~12~77 Petri dishes, the pH thereof was adiusted, they were allowed to stand uncovered under 256 nm ultraviolet light (30 cm from the light source). and the absorbance was measured with time.
~ The results are shown in Fig. 2. As is clear from the 'I figure, crocetin faded under ultraviolet light, but the -fading was considerablY suppressed with crocetin/ a -CD
CROCETIN-CONTAINING COLORING
~ield of the Invention The present invention relates to a crocetin-containing colorant, and specifically it relates to a crocetin-containing 1~' colorant which has been stabilized bY forming an inclusion I complex with cyclodextrin. Crocetin is a derivative of a yellow pigment found in plants such as gardenia and the like, and according to the present invention it is stabilized to ;~
widen the range of its use as a colorant.
. ~
~ Description of the Prior Art ~ `
~..
A method is known for stabilizing gardenia pigment (crocin) bY its inclusion complex with cYclodextrin (Japanese Patent Publication No.60-45229), but no method has been heretofore known for the stabilization of crocetin for its use as a pigment, which is an obiect of the Present invention.
~ Crocetin is a hydrolysate of crocin, the main component ¦ of the carotenoid gardenia yellow pigment, and it is ~ particularly unstable with resPeCt to light and chemicals.
¦ Methods have been proposed to improve its properties, such as I adding low concenSrations of ascorbic acid thereto, but the ¦ methods of use thereof are placed under strict control, and furthermore at present satisfactorY results cannot be obtained.
21~ ~,277 _mmar~ of the Invention An object of the present invention is to impart to crocetin resistance against li~ht and chemicals for its stability, thus providing a method for its use as a colorant.
The present invention provides a colorant consisting essentially of crocetin included by cyclodextrin.
The present invention also provides a process for producing the colorantt which comprises adding an aqueous alkaline solution of crocetin to a water paste of the cyclodextrin, and stirring to resulting mixture.
The present invention further provides a food or beverage colored by the colorant.
Brief Description of the Drawin~s Fi~ure 1 is a graph showing the results oi a light fastness test against fluorescent light.
Figure 2 is a qraph showing the results of a light ~-fastness test against ultraviolet light.
Detailed Description of the Invention Crocetin is obtained by hydrolyzing crocin, which is extracted from the above mentioned plant, but commercially available products (for example, products of Sigma, Inc.) may be -used.
Also, cyclodextrin (hereunder sometimes abbre~iated to "CD") is a cyclic oligosaccharide with a polymerization degree of 6-8 which is obtained by allowing cyclodextrin glucanotransferase (CGTase, EC 2.4.1.19) to act on starch or a hydrolysate thereof, and rpeclflc exarplee tùereof lnclude ~ -CD and r1xtures , "A ~
~J l ~ ~, 2 7 J) thereof, or mixtures of these and dextrin. Accordlng to the present invention, ~-CD alone and substances containing it are particularly suitable.
A crocetin-containing colorant according to the present invention may be obtained in the following manner.
First, a prescribed amount of crocetin which has been dissolved in an alkaline solution containing sodium hydroxidP, etc. is added to CD, particularly a--CD, which has been kneaded into a paste form with a small amount of water, and the mixture is vigorously stirred. The amount of water used is enough to form a stirrable paste, and in the case of a~CD, it may be added so that the solid concentration is about 40-60%. The stirring time will depend on the degree of stirring, but it is 10 minutes to 3 hours, and normally 60 minutes or more, and stirring may be effected while cooling so that the temperature does not rise too much over 80C.
After completion of the stirring, the pasty pigment which exists as an inclusion complex wlth CD is subjected to centrifugal separation (7,900 x G, 10 minutes, room temperature) to separate the non-lncluded pigment. The preclpitation portion obtained upon centrifugal separation is called a crocetin included by CD (hereunder sometimes shortened to "crocetin~CD inclusion complex") and this is used as the colorant according to the present invention.
The colorant according to the present invention may be used for coloring a wide variety of foods and beverages. For example, a refreshment beverage containing a sugar and a fruit ? s 1 't~'~;`)7 ~ J.~
juice (such as lemon juice) can be effectively colored by the colorant. Similarly, a fondant containing a sugar and starch may be effectively colored by the colorant. Further, a candy generally made of a sugar may be effectively colored by the colorant according to the present invention. The amount of the colorant varies widely depending upon various factors.
Exam~les A detailed description of the present invention will now be provided with reference to the Examples.
3a 2 ~ 7 7 ~ i Test Example 1 One part bY weight of crocetin dissolved in 0.1 M sodium hydroxide was added to 10 Parts by weight of a -CD 10 which had been prepared into a paste form with a small amount of water, and the mixture was vigorously stirred for 60 minutes and then subiected to centrifugal separation to obtain a -~
crocetin/ a -CD inclusion complex.
This crocetin included bY a -CD. ~ -CD. a mixture of a -. ~ - and ~ -CD (trade name: K-100. product of Ensuiko Sugar -Refining Co., Ltd.~. or a mixture of a -. ~ -CD and dextrin (trade name: K-50. product of Ensuiko Sugar Refining Co., Ltd.) and unprocessed crocetin were each dissolved in a Mcllvaine buffer solution (pH 7) containing 20% ethanol which had been diluted to 1/10 so that the absorbance at 420 nm and 450 nm was 0.4-0.8. to prePare test solutions.
A pre-determined amount of each of the test solutions was poured into a glass test tube and allowed to stand at room temperature under a fluorescent lamp at 900 lux. and the absorbance and the color difference were measured with time.
The results are shown in Eig. 1. As is clear from the figure. crocetin faded uPon exposure to fluorescent light.
but the fading was considerably supPressed with crocetin/ a -CD
inclusion complex. crocetin/ ~ -inclusion complex. croce~in/K-50 inclusion comPlex and crocetin/K-100 inclusion complex.
Test Example 2 The test solutions in Test Example 1 were poured onto '~ :
~ ~12~77 Petri dishes, the pH thereof was adiusted, they were allowed to stand uncovered under 256 nm ultraviolet light (30 cm from the light source). and the absorbance was measured with time.
~ The results are shown in Fig. 2. As is clear from the 'I figure, crocetin faded under ultraviolet light, but the -fading was considerablY suppressed with crocetin/ a -CD
3 inclusion complex. crocetin/ ~ -CD inclusion complex, crocetin/K-50 inclusion complex and crocetin/K-100 inclusion complex.
Test ExamPle 3 I A pre-determined amount of the reagents listed in Table 1 1 were added to each of the solutions in Test Example 1, and the fading with time was compared with a non-added solution. ~ -¦ Each of the reagents was added to a final concentration of 100 ppm. However, ferric chloride was added to a final concentration of 5 ppm. The solutions which had a 90% or higher rate of residual pigment comPared to the non-added solution were marked with a (t), and those below that were marked with a (-).
The results are shown in Table 1. As is clear from the table, crocetin alone rapidlY faded with sodium bisulfite, ferric chloride, sodium isoascorbate, cYsteine, sodium propionate, citric acid, etc., while with the crocetin/CD
inclusion complex, and particularlY the crocetin/ a -CD inclusion complex, crocetin/K-50 inclusion comPlex and crocetin/X-100 inclusion complex, the fading was considerably suPPressed.
Also, in the case of crocetin alone, fading was observed 1?,277 ,~
with a high concenlration of sodium chloride. but with crocetin/ a -CD inclusion complex. crocetin/ ~ -CD inclusion complex, crocetin/K-50 inclusion complex and crocetin/K-100 inclusion complex. the fading was considerably suppressed.
Table 1 Crocetin a -CD ~ -CD r -CD K-50 K-100 inclusion inclusion inclusion inclusion inclusion 1 complex complex complex comple~ complex Non-added + + + + + +
Sodium bisulfite - + - -Sodium perchlorate + + + + +
Aluminum chloride + + + + +
Zinc chloride + + + + +
Copper chloride + ~ + + +
Ferric chloride - + - - + + ~ :
Ascorbic acid - -~ + + + +
Isoascorbic acid - +
Cysteine - +
Citric acid - + + +
Propionic acid + + + + + +
Boric acid + + + + + -~
10% sodium chloride + + - + +
~ .
Test Example 4 The crocetin/ a ~ -./ r -CD inclusion comPlex and unprocessed crocetin were each dissolved in ~cllvaine buffer solutions (pH 6. 7. 8) which had been diluted to 1/10 so that the absorbance at 420 nm and 450 nm was 0.4-0.8. to prepare test solutions.
The color differences of the above mentioned test solutions were compared one hour after dissolution. The results are shown in 1'able 2. As is clear from the table.
with the crocetin alone the b value of the color tone at pH
x~ , , , ", ~ , , , " ", ~ ~ ,. . .
7 ~
1 6.0 was lower than that at pll 7.0, thus having a weaker ii development of yellow color. and the color difference was 3.5. with a lighter visual appearance. However. in the case of the crocetin/CD inclusion comPlex. the color difference was 0.6. with no great change in the visual aPPearance.
~ rom the above results. it is seen that the change in color tone due to pH is suppressed with crocetin/CD
inclusion complex.
Table 2 (Color difference) pH6.0 pH7.0 pH8.0 Crocetin 3.5 0 0.6 a -CD inclusion complex 0.2 0 0.5 -CD inclusion complex 0.3 0 0.5 ~ -CD inclusion complex 0.7 0 0.8 Bxample 1 (Refreshment beverage) To 100 g of sugar were added 0.2 g of citric acid, 0.05 g of malic acid and 10 cc of lemon juice. and a portion thereof prepared to 200 cc with a 1% sodium bicarbonate solution was adiusted to pH 7.0 with sodium bicarbonate. to make a iuice base.
I Four volumes of water was added per one volume of the ¦ juice base in which was dissolved crocetin. crocetin/ a -CD
¦ inclusion complex. crocetin/K-50 inclusion complex or crocetin/K-100 inclusion complex.and the mixtures were ¦ prepared so that the absorbance at 420 nm was 0.5.
~, - 7 -f'. ~ ~J ~ 7 7 l and then filled into glass containers which were sealed and j allowed to stand for one month in a sunny place, upon which the degree of fading thereof was comPared. As a result, as shown in Table 3, the beverages colored using each of the crocetin/CD inclusion comPlex were more stable under light than was the one using crocetin alone.
~.
¦ Table 3 Degree of fading (O ~ ~-Crocetin 80 Crocetin/ a -CD inclusion complex 30 Crocetin/K-50 inclusion complex 34 Crocetin/K-100 inclusion complex 35 Example 2 (~ondant) One-half tablespoon of corn starch and one tablespoon of water were heated for dissolution, 200 g of powdered sugar was added thereto and the mixture thoroughly mixed to prepare a smooth dough. Next, a solution prepared by dissolving crocetin or crocetin/ a -CD inclusion complex in 10 cc of a 1% sodium bicarbonate solution so that the absorbance at 420 nm was 2.5 was added to the above mentioned dough, and the mixture was gently heated to iust the right hardness and poured onto a solid base, One product obtained in this manner was allowed to stand in a sunny place.
while light was shielded from the other. As a result. when the fondant which was colored with the crocetin/ a -CD
- 8 - .
--`` 2 ~ 7 inclusion complex was used, there was no visible difference between the solution kept while shielding the light and the solution kept in the sunny place. and neither underwent fading. but with the crocetin alone. the fading of the solution which ~as allowed to stand in the sunny place was visibly noticeable. Thus it was determined that crocetin was stabilized by forming an inclusion comPlex with CD.
Example 3 (Hard candY) A complete solution of 130 g of sugar. 100 g of malt sYrup. 30 cc of water and 0.4 g of citric acid was heated to 50C in a vacuum until it reached a sugar concentration of 97% or greater. This concentrate was heated in a boiling water bath. and when it became soft crocetin or crocetin/K-50 inclusion complex was added thereto, and the mixture was adequately mixed and poured into a mold for forming. As a result. in the case of the candy which was colored with the crocetin/K-50 inclusion complex. there was no visible difference between the solution kept while shielding the light and the one kept in a sunny place. and neither showed fading. On the other hand. in the case of the candy colored with crocetin alone. the fading of the one which was allowed to stand in a sunnY place was observed to be visibly noticeable. Thus it was determined that crocetin was stabilized by forming an inclusion comPlex with CD.
As mentioned above. according to the present invention it is possible ~o imeart resis~ance a6ainst li~ht and various 7 7 i.
3 chemicals to crocetin. which is a hydrolYsate of crocin, the main component of the carotenoid gardenia yellow pigment.
Therefore, crocetin ~ay be added to various food products for ~-use as a stable colorant.
' :
:~
I
Test ExamPle 3 I A pre-determined amount of the reagents listed in Table 1 1 were added to each of the solutions in Test Example 1, and the fading with time was compared with a non-added solution. ~ -¦ Each of the reagents was added to a final concentration of 100 ppm. However, ferric chloride was added to a final concentration of 5 ppm. The solutions which had a 90% or higher rate of residual pigment comPared to the non-added solution were marked with a (t), and those below that were marked with a (-).
The results are shown in Table 1. As is clear from the table, crocetin alone rapidlY faded with sodium bisulfite, ferric chloride, sodium isoascorbate, cYsteine, sodium propionate, citric acid, etc., while with the crocetin/CD
inclusion complex, and particularlY the crocetin/ a -CD inclusion complex, crocetin/K-50 inclusion comPlex and crocetin/X-100 inclusion complex, the fading was considerably suPPressed.
Also, in the case of crocetin alone, fading was observed 1?,277 ,~
with a high concenlration of sodium chloride. but with crocetin/ a -CD inclusion complex. crocetin/ ~ -CD inclusion complex, crocetin/K-50 inclusion complex and crocetin/K-100 inclusion complex. the fading was considerably suppressed.
Table 1 Crocetin a -CD ~ -CD r -CD K-50 K-100 inclusion inclusion inclusion inclusion inclusion 1 complex complex complex comple~ complex Non-added + + + + + +
Sodium bisulfite - + - -Sodium perchlorate + + + + +
Aluminum chloride + + + + +
Zinc chloride + + + + +
Copper chloride + ~ + + +
Ferric chloride - + - - + + ~ :
Ascorbic acid - -~ + + + +
Isoascorbic acid - +
Cysteine - +
Citric acid - + + +
Propionic acid + + + + + +
Boric acid + + + + + -~
10% sodium chloride + + - + +
~ .
Test Example 4 The crocetin/ a ~ -./ r -CD inclusion comPlex and unprocessed crocetin were each dissolved in ~cllvaine buffer solutions (pH 6. 7. 8) which had been diluted to 1/10 so that the absorbance at 420 nm and 450 nm was 0.4-0.8. to prepare test solutions.
The color differences of the above mentioned test solutions were compared one hour after dissolution. The results are shown in 1'able 2. As is clear from the table.
with the crocetin alone the b value of the color tone at pH
x~ , , , ", ~ , , , " ", ~ ~ ,. . .
7 ~
1 6.0 was lower than that at pll 7.0, thus having a weaker ii development of yellow color. and the color difference was 3.5. with a lighter visual appearance. However. in the case of the crocetin/CD inclusion comPlex. the color difference was 0.6. with no great change in the visual aPPearance.
~ rom the above results. it is seen that the change in color tone due to pH is suppressed with crocetin/CD
inclusion complex.
Table 2 (Color difference) pH6.0 pH7.0 pH8.0 Crocetin 3.5 0 0.6 a -CD inclusion complex 0.2 0 0.5 -CD inclusion complex 0.3 0 0.5 ~ -CD inclusion complex 0.7 0 0.8 Bxample 1 (Refreshment beverage) To 100 g of sugar were added 0.2 g of citric acid, 0.05 g of malic acid and 10 cc of lemon juice. and a portion thereof prepared to 200 cc with a 1% sodium bicarbonate solution was adiusted to pH 7.0 with sodium bicarbonate. to make a iuice base.
I Four volumes of water was added per one volume of the ¦ juice base in which was dissolved crocetin. crocetin/ a -CD
¦ inclusion complex. crocetin/K-50 inclusion complex or crocetin/K-100 inclusion complex.and the mixtures were ¦ prepared so that the absorbance at 420 nm was 0.5.
~, - 7 -f'. ~ ~J ~ 7 7 l and then filled into glass containers which were sealed and j allowed to stand for one month in a sunny place, upon which the degree of fading thereof was comPared. As a result, as shown in Table 3, the beverages colored using each of the crocetin/CD inclusion comPlex were more stable under light than was the one using crocetin alone.
~.
¦ Table 3 Degree of fading (O ~ ~-Crocetin 80 Crocetin/ a -CD inclusion complex 30 Crocetin/K-50 inclusion complex 34 Crocetin/K-100 inclusion complex 35 Example 2 (~ondant) One-half tablespoon of corn starch and one tablespoon of water were heated for dissolution, 200 g of powdered sugar was added thereto and the mixture thoroughly mixed to prepare a smooth dough. Next, a solution prepared by dissolving crocetin or crocetin/ a -CD inclusion complex in 10 cc of a 1% sodium bicarbonate solution so that the absorbance at 420 nm was 2.5 was added to the above mentioned dough, and the mixture was gently heated to iust the right hardness and poured onto a solid base, One product obtained in this manner was allowed to stand in a sunny place.
while light was shielded from the other. As a result. when the fondant which was colored with the crocetin/ a -CD
- 8 - .
--`` 2 ~ 7 inclusion complex was used, there was no visible difference between the solution kept while shielding the light and the solution kept in the sunny place. and neither underwent fading. but with the crocetin alone. the fading of the solution which ~as allowed to stand in the sunny place was visibly noticeable. Thus it was determined that crocetin was stabilized by forming an inclusion comPlex with CD.
Example 3 (Hard candY) A complete solution of 130 g of sugar. 100 g of malt sYrup. 30 cc of water and 0.4 g of citric acid was heated to 50C in a vacuum until it reached a sugar concentration of 97% or greater. This concentrate was heated in a boiling water bath. and when it became soft crocetin or crocetin/K-50 inclusion complex was added thereto, and the mixture was adequately mixed and poured into a mold for forming. As a result. in the case of the candy which was colored with the crocetin/K-50 inclusion complex. there was no visible difference between the solution kept while shielding the light and the one kept in a sunny place. and neither showed fading. On the other hand. in the case of the candy colored with crocetin alone. the fading of the one which was allowed to stand in a sunnY place was observed to be visibly noticeable. Thus it was determined that crocetin was stabilized by forming an inclusion comPlex with CD.
As mentioned above. according to the present invention it is possible ~o imeart resis~ance a6ainst li~ht and various 7 7 i.
3 chemicals to crocetin. which is a hydrolYsate of crocin, the main component of the carotenoid gardenia yellow pigment.
Therefore, crocetin ~ay be added to various food products for ~-use as a stable colorant.
' :
:~
I
Claims (12)
1. A colorant consisting essentially of crocetin included by cyclodextrin.
2. The colorant according to Claim 1, wherein the cyclodextrin is .alpha.-cyclodextrin.
3. The colorant according to Claim 1, wherein the cyclodextrin is a mixture of .alpha.-cyclodextrin and at least one member selected from the group consisting of .beta.-cyclodextrin and .gamma.-cyclodextrin.
4. The colorant according to Claim 1, wherein the cyclodextrin is a mixture of .alpha.-, .beta.- and .gamma.-cyclodextrins.
5. The colorant according to Claim 1, wherein the cyclodextrin is a mixture of .alpha.-cyclodextrin, dextrin and at least one member selected from the group consisting of .beta.-cyclodextrin and .gamma.-cyclodextrin.
6. The colorant according to Claim 1, wherein the cyclodextrin is a mixture of dextrin and .alpha.-, .beta.- and .gamma.-cyclodextrin.
7. A process for producing the colorant as defined in Claim 1, 2, 3, 4, 5 or 6, which comprises:
adding an aqueous alkaline solution of crocetin to a water paste of the cyclodextrin, and stirring to resulting mixture.
adding an aqueous alkaline solution of crocetin to a water paste of the cyclodextrin, and stirring to resulting mixture.
8. The process according to Claim 7, wherein:
the stirring is conducted while cooling so that the temperature does not rise above 80°C, and the stirred mixture is subjected to centrifugal separation to separate the crocetin included by the cyclodextrin from the non-included crocetin.
the stirring is conducted while cooling so that the temperature does not rise above 80°C, and the stirred mixture is subjected to centrifugal separation to separate the crocetin included by the cyclodextrin from the non-included crocetin.
9. A food or beverage colored by the colorant as defined in Claim 1, 2, 3, 4, 5 or 6.
10. The colored food or beverage according to Claim 9, which is a refreshment beverage containing sugar and lemon juice.
11. The colored food or beverage according to Claim 9, which is a fondant containing corn starch and sugar.
12. The colored food or beverage according to Claim 9, which is a candy.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5059422A JPH06248193A (en) | 1993-02-25 | 1993-02-25 | Crocetin-containing pigment |
| JP59422/1993 | 1993-02-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2112277A1 true CA2112277A1 (en) | 1994-08-26 |
Family
ID=13112814
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002112277A Abandoned CA2112277A1 (en) | 1993-02-25 | 1993-12-23 | Crocetin-containing coloring |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US5424407A (en) |
| EP (1) | EP0612815B1 (en) |
| JP (1) | JPH06248193A (en) |
| CA (1) | CA2112277A1 (en) |
| DE (1) | DE69321338T2 (en) |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5700850A (en) | 1993-08-05 | 1997-12-23 | Kimberly-Clark Worldwide | Colorant compositions and colorant stabilizers |
| US6017661A (en) | 1994-11-09 | 2000-01-25 | Kimberly-Clark Corporation | Temporary marking using photoerasable colorants |
| US5733693A (en) | 1993-08-05 | 1998-03-31 | Kimberly-Clark Worldwide, Inc. | Method for improving the readability of data processing forms |
| US6017471A (en) | 1993-08-05 | 2000-01-25 | Kimberly-Clark Worldwide, Inc. | Colorants and colorant modifiers |
| US5865471A (en) | 1993-08-05 | 1999-02-02 | Kimberly-Clark Worldwide, Inc. | Photo-erasable data processing forms |
| US6211383B1 (en) | 1993-08-05 | 2001-04-03 | Kimberly-Clark Worldwide, Inc. | Nohr-McDonald elimination reaction |
| US5681380A (en) | 1995-06-05 | 1997-10-28 | Kimberly-Clark Worldwide, Inc. | Ink for ink jet printers |
| US5645964A (en) | 1993-08-05 | 1997-07-08 | Kimberly-Clark Corporation | Digital information recording media and method of using same |
| US5721287A (en) | 1993-08-05 | 1998-02-24 | Kimberly-Clark Worldwide, Inc. | Method of mutating a colorant by irradiation |
| US5773182A (en) | 1993-08-05 | 1998-06-30 | Kimberly-Clark Worldwide, Inc. | Method of light stabilizing a colorant |
| JP2704356B2 (en) * | 1994-02-08 | 1998-01-26 | 正和薬品株式会社 | Brain function improver |
| US6242057B1 (en) | 1994-06-30 | 2001-06-05 | Kimberly-Clark Worldwide, Inc. | Photoreactor composition and applications therefor |
| US5685754A (en) | 1994-06-30 | 1997-11-11 | Kimberly-Clark Corporation | Method of generating a reactive species and polymer coating applications therefor |
| US6071979A (en) | 1994-06-30 | 2000-06-06 | Kimberly-Clark Worldwide, Inc. | Photoreactor composition method of generating a reactive species and applications therefor |
| US6008268A (en) | 1994-10-21 | 1999-12-28 | Kimberly-Clark Worldwide, Inc. | Photoreactor composition, method of generating a reactive species, and applications therefor |
| SK160497A3 (en) | 1995-06-05 | 1998-06-03 | Kimberly Clark Co | Novel pre-dyes |
| US5786132A (en) | 1995-06-05 | 1998-07-28 | Kimberly-Clark Corporation | Pre-dyes, mutable dye compositions, and methods of developing a color |
| MX9710016A (en) | 1995-06-28 | 1998-07-31 | Kimberly Clark Co | Novel colorants and colorant modifiers. |
| US5782963A (en) | 1996-03-29 | 1998-07-21 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
| DE69620428T2 (en) | 1995-11-28 | 2002-11-14 | Kimberly Clark Co | LIGHT-STABILIZED FABRIC COMPOSITIONS |
| US5855655A (en) | 1996-03-29 | 1999-01-05 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
| US6099628A (en) | 1996-03-29 | 2000-08-08 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
| US5891229A (en) | 1996-03-29 | 1999-04-06 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
| US6524379B2 (en) | 1997-08-15 | 2003-02-25 | Kimberly-Clark Worldwide, Inc. | Colorants, colorant stabilizers, ink compositions, and improved methods of making the same |
| SK1552000A3 (en) | 1998-06-03 | 2000-08-14 | Kimberly Clark Co | Novel photoinitiators and applications therefor |
| JP2002517540A (en) | 1998-06-03 | 2002-06-18 | キンバリー クラーク ワールドワイド インコーポレイテッド | Neo nanoplast and microemulsion technology for ink and ink jet printing |
| BR9912003A (en) | 1998-07-20 | 2001-04-10 | Kimberly Clark Co | Enhanced inkjet ink compositions |
| CA2353685A1 (en) | 1998-09-28 | 2000-04-06 | Kimberly-Clark Worldwide, Inc. | Chelates comprising chinoid groups as photoinitiators |
| ES2195869T3 (en) | 1999-01-19 | 2003-12-16 | Kimberly Clark Co | NEW COLORS, COLOR STABILIZERS, INK COMPOUNDS AND IMPROVED METHODS FOR MANUFACTURING. |
| US6331056B1 (en) | 1999-02-25 | 2001-12-18 | Kimberly-Clark Worldwide, Inc. | Printing apparatus and applications therefor |
| US6294698B1 (en) | 1999-04-16 | 2001-09-25 | Kimberly-Clark Worldwide, Inc. | Photoinitiators and applications therefor |
| US6368395B1 (en) | 1999-05-24 | 2002-04-09 | Kimberly-Clark Worldwide, Inc. | Subphthalocyanine colorants, ink compositions, and method of making the same |
| IL163685A0 (en) | 2002-02-25 | 2005-12-18 | Diffusion Pharmaceuticals Llc | Bipolar trans carotenoid salts and their uses |
| US7759506B2 (en) * | 2002-02-25 | 2010-07-20 | Diffusion Pharmaceuticals Llc | Bipolar trans carotenoid salts and their uses |
| EP1667954B1 (en) * | 2003-08-25 | 2018-11-14 | Diffusion Pharmaceuticals LLC | Bipolar trans carotenoid salts and their uses |
| JP2005225842A (en) * | 2004-02-16 | 2005-08-25 | Riken Vitamin Co Ltd | Brain function improver |
| DE102004062857A1 (en) * | 2004-12-27 | 2006-07-13 | Siemens Ag | Method for determining at least one scaling factor for measured values of a computer tomography device |
| KR101315904B1 (en) | 2005-02-24 | 2013-10-08 | 디퓨젼 파마슈티컬즈 엘엘씨 | Trans Carotenoids, Their Synthesis, Formulation and Uses |
| JP2010524855A (en) | 2007-04-13 | 2010-07-22 | ディフュージョン・ファーマシューティカルズ・エルエルシー | Use of bipolar trans carotenoids as and in the pretreatment of peripheral vascular disease |
| MX2010004803A (en) | 2007-10-31 | 2010-09-09 | Diffusion Pharmaceuticals Llc | A new class of therapeutics that enhance small molecule diffusion. |
| US10130689B2 (en) | 2009-06-22 | 2018-11-20 | Diffusion Pharmaceuticals Llc | Diffusion enhancing compounds and their use alone or with thrombolytics |
| CA2801292C (en) | 2010-06-02 | 2019-01-22 | Diffusion Pharmaceuticals Llc | Oral formulations of bipolar trans carotenoids |
| JP5826674B2 (en) * | 2012-03-03 | 2015-12-02 | 理研ビタミン株式会社 | Gardenia yellowish liquid formulation |
| CN102898864B (en) * | 2012-11-09 | 2013-12-18 | 苏州衷中医药科技有限公司 | Method for refining gardenia yellow pigment by adopting solvent crystallization |
| CN104548628B (en) * | 2015-01-23 | 2015-10-21 | 广水市东晨农业科技有限公司 | A kind of Gardenia Yellow extraction element and gardenia yellow pigment with high color value extracting method |
| CN109152839A (en) | 2016-03-24 | 2019-01-04 | 扩散药品有限公司 | Purposes of the bipolarity trans-carotenoid together with chemotherapy and radiotherapy in treating cancer |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6045229B2 (en) * | 1978-03-04 | 1985-10-08 | 川島 文雄 | Stabilization method for natural dyes |
| JPS6045229A (en) * | 1983-08-23 | 1985-03-11 | Canon Inc | Electrically-driven rewinding device of film of camera |
| US4699664A (en) * | 1985-05-01 | 1987-10-13 | Nestec S.A. | Stabilized natural pigment complexes |
| HU199444B (en) * | 1985-09-10 | 1990-02-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing 7-isopropoxy-isoflavone-cyclodextrene inclusion complex and pharmaceutical compositions therefrom |
| JP2993724B2 (en) * | 1990-10-16 | 1999-12-27 | サントリー株式会社 | Stabilized yellow dye |
-
1993
- 1993-02-25 JP JP5059422A patent/JPH06248193A/en active Pending
- 1993-11-22 US US08/156,810 patent/US5424407A/en not_active Expired - Fee Related
- 1993-11-25 DE DE69321338T patent/DE69321338T2/en not_active Expired - Fee Related
- 1993-11-25 EP EP93118965A patent/EP0612815B1/en not_active Expired - Lifetime
- 1993-12-23 CA CA002112277A patent/CA2112277A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| DE69321338T2 (en) | 1999-03-25 |
| DE69321338D1 (en) | 1998-11-05 |
| EP0612815B1 (en) | 1998-09-30 |
| JPH06248193A (en) | 1994-09-06 |
| US5424407A (en) | 1995-06-13 |
| EP0612815A1 (en) | 1994-08-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2112277A1 (en) | Crocetin-containing coloring | |
| US5445842A (en) | Quercetin-containing coloring | |
| EP0877562B1 (en) | Water dispersible compositions containing natural hydrophilic, water-insoluble pigments, methods of preparing same and their use | |
| US4332825A (en) | Citrus food containing a cyclodextrin | |
| US6572906B1 (en) | Method for inhibiting fading of a natural pigment using nigerooligosaccharide or maltooligosaccharide or panose with or without an antioxidant | |
| IT9021866A1 (en) | PROCEDURE FOR PREPARING A NORBIXIN COMPLEX WITH A CYCLIC POLYESACCHARIDE OR WITH BRANCHED CHAIN SOLUBLE IN WATER OR A PROTEIN SOLUBLE IN WATER OR DISPERSIBLE IN WATER | |
| CN106459602B (en) | Tea-based to brown-based pigments | |
| US6329010B1 (en) | Process for producing a food colorant, colorant thus obtained and uses thereof | |
| US6630186B1 (en) | Drinks containing cochineal colorant and method of preventing discoloration thereof | |
| CN109601824A (en) | A kind of red yeast rice haematochrome color fixative and its application | |
| JPH02135070A (en) | Method for stabilizing carotenoid dye | |
| JP4996807B2 (en) | Dye stabilizer and dye stabilization method | |
| JPH02110164A (en) | Stabilization of anthocyan pigment | |
| WO2020111165A1 (en) | Composition for suppressing anthocyanin coloring-material deterioration | |
| JPH10248526A (en) | Manufacture of soft capsule for health auxiliary food | |
| CN107532187A (en) | The monascorubin that light resistance improves | |
| JPS623741A (en) | Method of coloring cakes in red or reddish purple | |
| JP2000253850A (en) | Pigment whose color fading is inhibited | |
| CN115844013A (en) | Method for improving stability of procyanidine in lycium ruthenicum murr | |
| Cosentino et al. | Stability of γ-irradiated carmine | |
| JPS623765A (en) | Red-purplish red powdery food | |
| Reineccius | Food Colorants | |
| JPS62269650A (en) | Production of salt-containing viscous food |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |