CA2112942A1 - Quercetin-containing coloring - Google Patents
Quercetin-containing coloringInfo
- Publication number
- CA2112942A1 CA2112942A1 CA002112942A CA2112942A CA2112942A1 CA 2112942 A1 CA2112942 A1 CA 2112942A1 CA 002112942 A CA002112942 A CA 002112942A CA 2112942 A CA2112942 A CA 2112942A CA 2112942 A1 CA2112942 A1 CA 2112942A1
- Authority
- CA
- Canada
- Prior art keywords
- quercetin
- colorant
- substance
- cyclodextrin
- inclusion complex
- 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 quercetin-containing colorant which has as an effective component a quercetin included by cyclodextrin.
Effective use thereof as a colorant is possible by imparting thereto resistance against light, heat and chemicals to quercetin which is a flavonoid yellow substance. The colorant may be added to various food products for use of quercetin as a stable coloring matter.
A quercetin-containing colorant which has as an effective component a quercetin included by cyclodextrin.
Effective use thereof as a colorant is possible by imparting thereto resistance against light, heat and chemicals to quercetin which is a flavonoid yellow substance. The colorant may be added to various food products for use of quercetin as a stable coloring matter.
Description
2~2942 QUERCETIN-CONTAINING COLORING
Field of the Invention The present invention relates to a quercetin-containing colorant, and sPecificallY it relates to a quercetin-containing colorant which has been stabilized by forming an inclusion complex with cYclodextrin. Quercetin is a Yellow substance contained in plants such as Japanese pagoda. onion and the like, and according to the present invention it is ~ ;
stabilized for use as a colorant.
Description of the Prior Art A method has been proposed for using quercetin in food preservation. for the improvement of solubility and as an antioxidant. by its inclusion comPlex with cyclodextrin (Japanese Patent Publication No.Hei 2-268643), but no method has been heretofore known for the use of quercetin/cYclodextrin inclusion complexes as pigments.
Summary of the Invention Quercetin is alkali-soluble, but at pHs lower than neutral it becomes poorly soluble and its color changes considerablY.
Quercetin is an aglycon of rutin and quercitrin, and it is widely distributed among plants, imparting a bright Yellow color thereto under alkaline conditions. However. quercetin 29~2 ¦ is unstable under light and heat. and therefore it is almost never used as a colorant.
An obiect of the present invention is to impart to quercetin resistance against light, heat and chemicals. thus providing a method for its use as a colorant.
d ~ Brief Description of the Drawings : ~ig. 1 is a graph showing the results of a light ~ fastness test against fluorescent light.
¦ Fig. 2 is a graph showing the results of a light fastness test against ultraviolet light.
~ ig. 3 is a graph showing the results of a light fastness test against ultraviolet light after thermal -treatment.
~ :
Detailed Description of the Invention The present invention relates to a quercetin-containing colorant having as an effective component a quercetin included bY cyclodextrin.
The quercetin to be used maY be, in addition to crude and purified products obtained by extraction from the above mentioned plants, commercially available products (for example, products of Tokyo Kasei, Inc.)O
Also. cyclodextrin (hereunder abbreviated 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 OD starch or a hYdrolysate thereof. and ~' ~ 12 9 ~ 2 73299-24 specific examples thereof include ~-t ~- and y-CD. According to the present invention, ~-CD is particularly suitable.
A quercetin-containing colorant accordiny to the present invention may be obtained in the following manner.
First, 1-2 parts by weight of quercetin which has been dissolved in an organic solvent such as ethanol, is added to lO `~
parts by weight of CD which is dissolved to saturation in water, etc. as the solvent, and the mixture is vigorously stirred.
Depending on the degree of stirring, it is carried out for lO
minutes to 3 hours, and normally 60 minutes or more, and cooling is effected while stirring with care so that the temperature does not rise too much over 80.
After completion of the stirring, since most of the pigment precipitates with the quercetin, the mixture is subjected to centrifugal separation (7,900 x G, lO minutes, room temperature) to separate the non-included pigment. The quercetin included by CD (hereunder sometimes shortened to quercetin/CD inclusion complex), is used as the colorant according to the present invention.
The colorant of the present invention is used in various substances and mainly in beverage, food, cosmetics, etc.
and the amount and the manner of mixing are in accordance with the usual way. For example, when the colorant is used in beverage such as fruit juice or fruit juice-based drink, the colorant may be used in an amount of O.OOl to 1% by weight of the beverage. When the colorant is used in food such as hard candy it may be used in an amount of 0.001 to 5~ by weight.
Field of the Invention The present invention relates to a quercetin-containing colorant, and sPecificallY it relates to a quercetin-containing colorant which has been stabilized by forming an inclusion complex with cYclodextrin. Quercetin is a Yellow substance contained in plants such as Japanese pagoda. onion and the like, and according to the present invention it is ~ ;
stabilized for use as a colorant.
Description of the Prior Art A method has been proposed for using quercetin in food preservation. for the improvement of solubility and as an antioxidant. by its inclusion comPlex with cyclodextrin (Japanese Patent Publication No.Hei 2-268643), but no method has been heretofore known for the use of quercetin/cYclodextrin inclusion complexes as pigments.
Summary of the Invention Quercetin is alkali-soluble, but at pHs lower than neutral it becomes poorly soluble and its color changes considerablY.
Quercetin is an aglycon of rutin and quercitrin, and it is widely distributed among plants, imparting a bright Yellow color thereto under alkaline conditions. However. quercetin 29~2 ¦ is unstable under light and heat. and therefore it is almost never used as a colorant.
An obiect of the present invention is to impart to quercetin resistance against light, heat and chemicals. thus providing a method for its use as a colorant.
d ~ Brief Description of the Drawings : ~ig. 1 is a graph showing the results of a light ~ fastness test against fluorescent light.
¦ Fig. 2 is a graph showing the results of a light fastness test against ultraviolet light.
~ ig. 3 is a graph showing the results of a light fastness test against ultraviolet light after thermal -treatment.
~ :
Detailed Description of the Invention The present invention relates to a quercetin-containing colorant having as an effective component a quercetin included bY cyclodextrin.
The quercetin to be used maY be, in addition to crude and purified products obtained by extraction from the above mentioned plants, commercially available products (for example, products of Tokyo Kasei, Inc.)O
Also. cyclodextrin (hereunder abbreviated 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 OD starch or a hYdrolysate thereof. and ~' ~ 12 9 ~ 2 73299-24 specific examples thereof include ~-t ~- and y-CD. According to the present invention, ~-CD is particularly suitable.
A quercetin-containing colorant accordiny to the present invention may be obtained in the following manner.
First, 1-2 parts by weight of quercetin which has been dissolved in an organic solvent such as ethanol, is added to lO `~
parts by weight of CD which is dissolved to saturation in water, etc. as the solvent, and the mixture is vigorously stirred.
Depending on the degree of stirring, it is carried out for lO
minutes to 3 hours, and normally 60 minutes or more, and cooling is effected while stirring with care so that the temperature does not rise too much over 80.
After completion of the stirring, since most of the pigment precipitates with the quercetin, the mixture is subjected to centrifugal separation (7,900 x G, lO minutes, room temperature) to separate the non-included pigment. The quercetin included by CD (hereunder sometimes shortened to quercetin/CD inclusion complex), is used as the colorant according to the present invention.
The colorant of the present invention is used in various substances and mainly in beverage, food, cosmetics, etc.
and the amount and the manner of mixing are in accordance with the usual way. For example, when the colorant is used in beverage such as fruit juice or fruit juice-based drink, the colorant may be used in an amount of O.OOl to 1% by weight of the beverage. When the colorant is used in food such as hard candy it may be used in an amount of 0.001 to 5~ by weight.
~ ?~ 1 1 2 9 ~ 2 3299 24 Similarly, when the colorant is used in cosmetics, it may be used in an amoun-t of 0.001 to 5% by weight. Although these substances may be those which tend to be oxidized and an anti-oxidation is desirable, the present invention can be applied to such substances which normally are not easily oxidizable and an anti-oxidation is not required.
Examples A detailed description of the present invention will now be provided with reference to the Examples.
- 10 Test Example 1 One part by weight of quercetin dissolved in 99% ethanol was added to 2 parts hy weight of CD which was dlssolved ln ~ .~
?; ~, ~ - 3a -~ ` ~
.,`~,,i ?~1129427329g-24 water to saturation, and the mixture ~as vigorously stirred .~ for 60 minutes and then subiected to centri~ugal separation to obtain a quercetin/CD inclusion complex.
This quercetin/ ~ -CD inclusion complex and unprocessed quercetin 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 400 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 Fig. 1. As is clear from the figure. quercetin faded under fluorescent light. but the fading was considerably suppressed with quercetin/CD
inclusion complex. and no change in the color tone was observed.
Test Example 2 After the pH of each of the test solutions in Test Example 1 was adiusted. they were poured into transparent polyethylene bags ~ade-nELrk Stomacker 80. product of Organo. Inc.) and sealed and allowed to stand for 2 daYs under 256 nm ultraviolet light (30 cm from the light source), after which the absorbance was measured. The results are shown in Fig. 2. As is clear from the figure. quercetin faded under ultraviolet light. but the fading was considerably b~ suppressed with quercetin/ ~ -CD inclusion complex.
~ ..
~..
~ - 4 -" ~' '.!
3 1 ~ 2~2 , ;.~..
Test Example 3 After the pH of each of the test solutions in Test Example 1 was adiusted. theY were subjected to thermal treatment at 121C for 30 minutes, after which the absorbance and color difference were measured in the same manner as in Test Example 2. The results are shown in Fig. 3. As îs clear from the figure. quercetin faded. but the fading was considerably suppressed with quercetin/ ~ -CD inclusion complex.
Test Example 4 A predetermined amount of the chemicals listed in Table 1 were added to the solutions in Test Example 1, and the performance was compared with that of a non-added solution.
The same procedure was carried out with quercetin/ a -CD
inclusion complex and quercetin/ r -CD inclusion complex. Each of the chemicals 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 residue of the colorant residue compared to the non-added solution were marked with a (+). and those below that were mar~ed with a (-).
The results are shown in Table 1. As is clear from the table. quercetin alone. quercetin/ a -CD inclusion complex and quercetin/ r -CD inclusion complex rapidly faded with sodium ~i ,:"..,1 ~ bisulfite, while with the quercetin/ ~ -CD inclusion complex.
'ii ~ the fading was significantly suPpressed.
.`'`'~ ,.
,~; - 5 -E``':~
~'.~,' :~ .
Table 1 Quercetin~ -CD inclusion complex Non-added + +
Sodium bisulfite - +
Sodium perchlorate + +
Aluminum chloride + +
Zinc chloride + +
Copper chloride + +
Ferric chloride +
Example 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 200 cc of mixture prepared by addition of a 1% sodium bicarbonate solution thereto was adiusted to pH 7.0 to make a iuice base.
~ our volumes of water was added per one volume of the juice base in which had been dissolved quercetin. or quercetin/ ~ -CD inclusion complex, and the mixtures were prepared so that the absorbance at 420 nm was 0.5. and then filled into glass containers which were sealed and allowed to stand for 3 weeks in a sunny place. upon which the degree of fading thereof was compared. As a result. the beverage which was colored using the quercetin/ ~ -CD inclusion comPlex was more stable under light than was the one using quercetin alone.
Example 2 (Hard candY) A complete solution of 130 g of sugar. 100 g of malt 2 9 ~ ~
, syrup. 30 cc of water and 0.4 g of citric acid was heated to 50C in vacuo until it reached a sugar concentration of 97% or greater. This concentrate was heated in a boiling water bath, and when it became soft quercetin or quercetin/ ~ -CD 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 quercetin/ ~ -CD
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 underwent fading. On the other hand, in the case of the candy colored with quercetin alone.
~1,,' ,~
r~ the fading of the one which was allowed to stand in a sunnY
~ ..
place was observed to be vlslbly notlceable. Thus it was determined that quercetin was stabilized by forming an inclusion complex with CD.
As mentioned above. according to the present invention it is possible to effectively use quercetin. which is a flavonoid yellow substance. as a colorant by imparting thereto resistance against light. heat and chemicals.
Therefore. quercetin may be added to various food products .!.'~. ,~
~i~ for use as a stable coloring matter.
~' .'~""~ .
,:'.'"~ ' ,,;,i~.l ~ 7 -
Examples A detailed description of the present invention will now be provided with reference to the Examples.
- 10 Test Example 1 One part by weight of quercetin dissolved in 99% ethanol was added to 2 parts hy weight of CD which was dlssolved ln ~ .~
?; ~, ~ - 3a -~ ` ~
.,`~,,i ?~1129427329g-24 water to saturation, and the mixture ~as vigorously stirred .~ for 60 minutes and then subiected to centri~ugal separation to obtain a quercetin/CD inclusion complex.
This quercetin/ ~ -CD inclusion complex and unprocessed quercetin 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 400 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 Fig. 1. As is clear from the figure. quercetin faded under fluorescent light. but the fading was considerably suppressed with quercetin/CD
inclusion complex. and no change in the color tone was observed.
Test Example 2 After the pH of each of the test solutions in Test Example 1 was adiusted. they were poured into transparent polyethylene bags ~ade-nELrk Stomacker 80. product of Organo. Inc.) and sealed and allowed to stand for 2 daYs under 256 nm ultraviolet light (30 cm from the light source), after which the absorbance was measured. The results are shown in Fig. 2. As is clear from the figure. quercetin faded under ultraviolet light. but the fading was considerably b~ suppressed with quercetin/ ~ -CD inclusion complex.
~ ..
~..
~ - 4 -" ~' '.!
3 1 ~ 2~2 , ;.~..
Test Example 3 After the pH of each of the test solutions in Test Example 1 was adiusted. theY were subjected to thermal treatment at 121C for 30 minutes, after which the absorbance and color difference were measured in the same manner as in Test Example 2. The results are shown in Fig. 3. As îs clear from the figure. quercetin faded. but the fading was considerably suppressed with quercetin/ ~ -CD inclusion complex.
Test Example 4 A predetermined amount of the chemicals listed in Table 1 were added to the solutions in Test Example 1, and the performance was compared with that of a non-added solution.
The same procedure was carried out with quercetin/ a -CD
inclusion complex and quercetin/ r -CD inclusion complex. Each of the chemicals 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 residue of the colorant residue compared to the non-added solution were marked with a (+). and those below that were mar~ed with a (-).
The results are shown in Table 1. As is clear from the table. quercetin alone. quercetin/ a -CD inclusion complex and quercetin/ r -CD inclusion complex rapidly faded with sodium ~i ,:"..,1 ~ bisulfite, while with the quercetin/ ~ -CD inclusion complex.
'ii ~ the fading was significantly suPpressed.
.`'`'~ ,.
,~; - 5 -E``':~
~'.~,' :~ .
Table 1 Quercetin~ -CD inclusion complex Non-added + +
Sodium bisulfite - +
Sodium perchlorate + +
Aluminum chloride + +
Zinc chloride + +
Copper chloride + +
Ferric chloride +
Example 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 200 cc of mixture prepared by addition of a 1% sodium bicarbonate solution thereto was adiusted to pH 7.0 to make a iuice base.
~ our volumes of water was added per one volume of the juice base in which had been dissolved quercetin. or quercetin/ ~ -CD inclusion complex, and the mixtures were prepared so that the absorbance at 420 nm was 0.5. and then filled into glass containers which were sealed and allowed to stand for 3 weeks in a sunny place. upon which the degree of fading thereof was compared. As a result. the beverage which was colored using the quercetin/ ~ -CD inclusion comPlex was more stable under light than was the one using quercetin alone.
Example 2 (Hard candY) A complete solution of 130 g of sugar. 100 g of malt 2 9 ~ ~
, syrup. 30 cc of water and 0.4 g of citric acid was heated to 50C in vacuo until it reached a sugar concentration of 97% or greater. This concentrate was heated in a boiling water bath, and when it became soft quercetin or quercetin/ ~ -CD 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 quercetin/ ~ -CD
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 underwent fading. On the other hand, in the case of the candy colored with quercetin alone.
~1,,' ,~
r~ the fading of the one which was allowed to stand in a sunnY
~ ..
place was observed to be vlslbly notlceable. Thus it was determined that quercetin was stabilized by forming an inclusion complex with CD.
As mentioned above. according to the present invention it is possible to effectively use quercetin. which is a flavonoid yellow substance. as a colorant by imparting thereto resistance against light. heat and chemicals.
Therefore. quercetin may be added to various food products .!.'~. ,~
~i~ for use as a stable coloring matter.
~' .'~""~ .
,:'.'"~ ' ,,;,i~.l ~ 7 -
Claims (11)
1. A colorant consisting essentially of quercetin included by cyclodextrin.
2. The colorant according to claim 1, wherein the cyclo-dextrin is .beta.-cyclodextrin.
3. The colorant according to claim 1, wherein the quercetin included by cyclodextrin is obtained by adding a quercetin solution to a mixture of cyclodextrin and water, and stirring the resulting mixture.
4. A method of imparting a yellow color to a substance, which comprises mixing with the substance a coloring effective amount of the colorant as defined in claim 1, 2 or 3.
5. The method according to claim 4, wherein the substance is beverage.
6. The method according to claim 4, wherein the substance is food.
7. The method according to claim 4, wherein the substance is cosmetics.
8. A substance yellow colored by the colorant as defined in claim 1, 2 or 3.
9. The substance according to claim 8, wherein the substance is beverage.
10. The substance according to claim 8, wherein the substance is food.
11. The substance according to claim 8, wherein the substance is cosmetics.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5059421A JPH06248194A (en) | 1993-02-25 | 1993-02-25 | Coloring matter containing quercetin |
| JP59421/1993 | 1993-02-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2112942A1 true CA2112942A1 (en) | 1994-08-26 |
Family
ID=13112788
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002112942A Abandoned CA2112942A1 (en) | 1993-02-25 | 1994-01-06 | Quercetin-containing coloring |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US5445842A (en) |
| EP (1) | EP0612814A1 (en) |
| JP (1) | JPH06248194A (en) |
| CA (1) | CA2112942A1 (en) |
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5721287A (en) | 1993-08-05 | 1998-02-24 | Kimberly-Clark Worldwide, Inc. | Method of mutating a colorant by irradiation |
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| US5891229A (en) | 1996-03-29 | 1999-04-06 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
| FR2763342B1 (en) * | 1997-05-13 | 2000-11-03 | Biochimie Appliquee Soc | CULTURE MEDIUM FOR THE SPECIFIC DETECTION OF ENTEROBACTERIA, METHOD FOR OBTAINING AND USING SAME |
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| AUPP254598A0 (en) * | 1998-03-23 | 1998-04-23 | Quality Wheat Crc Limited | Food colouring and method for producing same |
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| US6287603B1 (en) * | 1999-09-16 | 2001-09-11 | Nestec S.A. | Cyclodextrin flavor delivery systems |
| US7132296B2 (en) * | 2002-02-15 | 2006-11-07 | Medical Products Manufacturing, Llc | Method for assaying the antioxidant capacity of a sample |
| CA2538126A1 (en) * | 2003-10-06 | 2005-05-06 | Smith & Nephew, Inc. | Modular navigated portal |
| DE102004038728A1 (en) * | 2004-08-10 | 2006-03-02 | Merck Patent Gmbh | Flavonoid complexes |
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| EP2755499A1 (en) * | 2011-09-13 | 2014-07-23 | Nestec S.A. | Quercetin for browning food surfaces |
| PL408195A1 (en) * | 2014-05-12 | 2015-11-23 | Zito Spółka Cywilna | Dyeing composition and applications of the dyeing composition |
| CN107312355B (en) * | 2017-06-12 | 2020-09-04 | 暨南大学 | Preparation and application of purple-skin onion pigment |
| CN112236525A (en) | 2018-06-01 | 2021-01-15 | 太阳化学株式会社 | Compositions containing flavonoid-cyclodextrin inclusion compounds |
| JP6931747B2 (en) * | 2018-10-30 | 2021-09-08 | 太陽化学株式会社 | Beverages in containers |
Family Cites Families (9)
| 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 |
| JPS63190815A (en) * | 1987-02-04 | 1988-08-08 | Hoou Kk | Powdery hair dye composition |
| JPH0299563A (en) * | 1988-10-06 | 1990-04-11 | San Ei Chem Ind Ltd | Method for deepening color and stabilization of anthocyan pigment |
| ES2071010T3 (en) * | 1989-03-08 | 1995-06-16 | Hayashibara Biochem Lab | PREPARATION AND USES OF THE ALPHA-GLYCOSYL ROUTINE. |
| JPH02268643A (en) * | 1989-04-07 | 1990-11-02 | Seiwa Kasei Kk | Preservation of food |
| JP2898019B2 (en) * | 1989-08-21 | 1999-05-31 | 三栄源エフ・エフ・アイ株式会社 | Method for dissolving poorly water-soluble flavonoids |
| US5171573A (en) * | 1989-09-28 | 1992-12-15 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | 4G -alpha-D-glucopyranosyl rutin, and its preparation and uses |
| JPH04136075A (en) * | 1990-09-26 | 1992-05-11 | Mitsubishi Electric Corp | Method for clathration of coloring matter |
| US5230915A (en) * | 1990-10-24 | 1993-07-27 | Fereidoon Shahidi | Process for preparing a powdered cooked cured-meat pigment |
-
1993
- 1993-02-25 JP JP5059421A patent/JPH06248194A/en active Pending
- 1993-11-22 US US08/156,805 patent/US5445842A/en not_active Expired - Fee Related
- 1993-11-25 EP EP93118964A patent/EP0612814A1/en not_active Withdrawn
-
1994
- 1994-01-06 CA CA002112942A patent/CA2112942A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP0612814A1 (en) | 1994-08-31 |
| JPH06248194A (en) | 1994-09-06 |
| US5445842A (en) | 1995-08-29 |
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| Date | Code | Title | Description |
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| FZDE | Discontinued |