WO2000007458A1 - Method for the conversion of xanthophylls in plant material - Google Patents
Method for the conversion of xanthophylls in plant material Download PDFInfo
- Publication number
- WO2000007458A1 WO2000007458A1 PCT/US1998/016393 US9816393W WO0007458A1 WO 2000007458 A1 WO2000007458 A1 WO 2000007458A1 US 9816393 W US9816393 W US 9816393W WO 0007458 A1 WO0007458 A1 WO 0007458A1
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- WO
- WIPO (PCT)
- Prior art keywords
- plant material
- xanthophylls
- free form
- improved plant
- improved
- Prior art date
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/24—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by six-membered non-aromatic rings, e.g. beta-carotene
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/179—Colouring agents, e.g. pigmenting or dyeing agents
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K50/00—Feeding-stuffs specially adapted for particular animals
- A23K50/70—Feeding-stuffs specially adapted for particular animals for birds
- A23K50/75—Feeding-stuffs specially adapted for particular animals for birds for poultry
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/095—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of organic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/128—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by alcoholysis
- C07C29/1285—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by alcoholysis of esters of organic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Definitions
- This invention relates to the in situ process for converting non free form xanthophylls to free xanthophylls in the biological material of the plant.
- the method more particularly relates to a method that would liberate xanthophylls by transester ⁇ cation of acyl- xanthophylls in plant materials.
- Carotenoids are a group of red and yellow pigments contained in plants and fruits.
- Carotenoids include carotenes and hydroxylated carotenoids designated xanthophylls.
- Xanthophylls include lutein. zeaxanthin, capsorubin, capsanthiii. astaxanthin, and canthaxanthin.
- the animal feed industry and the food industry and the pharmaceutical industry have all indicated a slrong interest in xanthophylls.
- the poultry industry receives a benefit in adding the xanthophylls to increase the yolk color of eggs.
- the pharmaceutical companies have found that xanthophylls are useful in certain lumor treatments and as an anlioxidanl.
- the food industry has found that consumers are looking for naturally occurring food colorants. Annatto, saffron and paprika are a few natural carotenoids that have traditionally been used for food coloring.
- xanthophylls contain less chorophylls but often the xanthophylls exists in the esterified form with fatty acids such as myrislic, lauric, and palmitic acids.
- fatty acids such as myrislic, lauric, and palmitic acids.
- the xanthophylls ester must undergo conversion to the free xanthophylls. The free xanthophyll can then be metabolizable by the body.
- Various plant materials contain xanthophylls; the desired xanthophylls will drive the selection of thfi material used. For example it is well know to use the petals of the marigold flower. Tagetes erecta for the extraction of the lutein xanthophylls.
- Marigolds are readily cultivated and have been used as a pigment source for poultry. Lutein occurs in the marigold flower diacylated with palmitic and myristic acids in long fatty acid esters typically as diesters in the chromoplastids.
- the animal feed industry has taken two different approaches to providing xanthophylls in animal feeds, particularly lutein to poultry feeds.
- the industry lias used the dried marigold meal as a feed additive thus providing the lutein in the less useable acylated form.
- This form of the xanthophylls requires more consumption of the marigold meal to get the pigment desired.
- the industry has used a number of processes, starting with the extraction of the xanthophylls from the plant material and the formation of oleoresins.
- the industry then goes further and processes the oleoresins to convert the xanthophylls from the acylated form to the free form by a number of differing processes including trdnsesterfication for some oleoresin processing of paprika, though for lutein the process is primarily by saponification.
- the converted oleoresin requires less consumption by the animal to get the desired xanthophylls.
- formation of oleoresins and the processing tliereof by saponification is both time consuming and adds labor costs to the feed product.
- Saponificaiion is the conversion of the fatly acid lo into a soap by treating it with an alkali.
- the saponification number is the number of milligrams of potassium hydroxide required to saponify one gram of the ester.
- saponificaiion the industry has often used solvents lo crystallize the lutein from ihe oleoresin. This has made the xanthophylls more pure and available to the organism consuming the lutein but it has added lime and labor lo Ihe process of supplying ihe xanthophylls lo ihe feed mixture.
- Patent No. 83, 173, 164 shows paprika pigments can be prepared by treating paprika oleoresin with alkali at temperatures below 50° C in the presence of halogen ions, sulfates. bicarbonate, carbonate, phosphate, and aliphatic carboxy ions, and then treated with an organic solvent and finally extracted with acetone.
- the US patent 5.382,714 describes a method of producing substantially pure lutein.
- the starting material was marigold petals.
- the process of saponification of the petals is briefly described in column 5 example 1.
- the flower petals were tested for herbicides and pesticides and then the xanthophylls containing material was subjected to saponification with aqueous potassium hydroxide. This was accomplished by continuous mixing under heat (65-70 degrees C) of food grade potassium hydroxide 45%. This accomplished conversion of 98% of lutein into a form that was free of fatty acids and present as a yellow oil. This material could then be used as a feed or food additive.
- the present invention provides a method of in situ conversion of the xanthophylls into the free fo ⁇ n by liberation of the xanthophylls by transesterification.
- This oleoresin conversion requires an organic solvent extraction of the material from the plant material. Hexane is often used.
- the present invention provides in situ free form xanthophylls by transesterification of in situ material thus eliminating the need for an oleoresin or saponification of the material.
- the present invention allows the marigold meal to be subjected to transesterification and then used without the extraction of the xanthophylls from the meal.
- the objective of this invention is to fulfill that need.
- Another object of my invention is lo provide a marigold meal thai has a high free lutein content.
- Yet another object of my invention is to provide a marigold meal as a feed additive that provides additional pigment to eggs when compared to the same marigold meal as a feed additive that has not undergone the treatment of the present invention.
- Another additional objective of my invention is to provide plant material that contains substantially a greater percentage of the free form of xanthophylls then contained in the original plant material prior to liberation.
- the present invention includes an improved plant material made from a natural plant material.
- This plant material contains at least some non free form xanthophylls. comprising plant materials containing in situ, less of said non free form xanthophylls, and more of free form xanthophylls wherein the free form of xanthophylls in situ in the improved plant material has increased beyond the amount in the natural plant material.
- the invention can have a number of different plant materials including flowers and the petals of flowers.
- a flower of particular usefulness is Tagetes erect . This type of flower is useful if the desired xanthophylls are lutein.
- the bulk of the xanthophylls in marigolds exists in nature as non free form xanthophylls. as fatty acid esters.
- the present invention is adapted to convert the nonfree xanthophylls into the free form of xanthophylls. When the marigold flowers are employed, this conversion by transesterification produces a nonacylated lutein.
- the present invention can improve plant material so that it contains at least 5% more free form xanthophllys than does the natural plant material in situ.
- Another embodiment of the present invention is an improved animal feed composition
- a source of carbohydrates selected from the group consisting of sovbean. peanuls, corn, alfalfa, wheat, barley and, improved plant material conlaining in situ more free form xanthophylls then the natural in situ amount of xanthophylls in the plant material that the improved plant material was formed from wherein the xanthophylls are more bioavailable lo an animal fed the animal feed.
- This feed can contain improved plant material that is flowers. If the desired xanthophyll is lutein then said flowers are marigolds. If the desired xanthophyll is capsanthin then paprika can be used.
- This animal feed is designed for the nutritional requirements of poultry, wherein Ihe animal products such as eggs and meat can have the xanthophyll act as a pigmenter.
- the present invention is believed particularly useful for chickens. Certain xanthophylls could also be useful in other animal feeds lo color the meal or olher animal byproducts.
- a feed for poultry is preferably characterized by having animal feed evidencing the bioavailability of the free form xanthophylls by having increased pigmentation from the consumption of said free form xanthophylls. especially when Ihe fed xanthophylls are lutein.
- the present invention encompasses a product and also the method of forming the free form xanthophylls.
- the present invention covers a method of improved plant material made from a natural plant material containing at least some non free form xanthophylls by the following steps of: treating said natural plant material in situ with a solvent; adding a base capable of transesterification of non free form xanthophylls to the free form xanthophylls; neutralizing the reaction wherein forming the improved plant material having more free form xanthophylls then the natural plant material.
- the method can also include the step of drying the improved plant materials to remove any solvent.
- the method of the present invention includes using planl material such as flowers. If the desired product is lutein, then flowers such as Tagetes erecta can be used.
- the method uses a solvent in the reaction.
- the solvent can be broadly an alcohol and more preferred an alkanol or alkenol. If an alcohol is used the alcohol preferably has one to four carbons.
- the alcohol is selected from the group consisting of methanol, etlianol. isopropyl alcohol, butanol and the like.
- the method of the present invention uses a base.
- the base can be selected from the group consisting of. potassium hydroxide, potassium sorbate. NaO e. animal liver lipase, yeast lipase, NaOEt. KOMe, KOEt. Na : C0 3 . K : C0 and the like.
- the melhod also includes the step of slopping ihe reaclion by neutralizing the reaction wilh a Lewis acid.
- the preferred Lewis acid is phosphoric acid.
- the Lewis acid can be selected from Ihe group consisting of HCL, NH 4 CL, sulfuric acid, acetic acid, ALCL 3 and the like.
- the method does not require an extractor such as petroleum ether or hexane or a number of other known extractors lo remove the xanthophyll from ihe plant material.
- the method can have plant material such as flowers, roots or fruit but preferably without chlorophyll in the product.
- FIGURE 1- chromatogram of marigold meal.
- FIGURE 3- shows the chromatogram of conversion to free form of capsanthin from treated paprika.
- FIGURE 4- shows the chromatogram of conversion to free form of lutein from treated marigold meal.
- FIGURE 5- shows the Roche fan scale over days for the egg yolk color of the present invention at two mg/Kg levels and of the commercial product.
- FIGURE 6- shows Ihe mg/Kg of xanthophylls in the egg yolks over days of Ihe three treatments.
- Tl ⁇ s invention relates to the in silu process for converting non free form xanthophylls to free xanthophylls in the biological material of the plant.
- the method more particularly relates to a method that would liberate xanthophylls by transesterification of acyl-xanthophylls in plant materials. And improved plant material having more free form xanthophyll then the original plant material from which it was made.
- the present invention provides a method of liberating xanthophylls in silu in plant or vegetable or fruit material.
- a xanthophyll in the free form such as lutein, zeaxanthin or capsanthin is formed from the xanthophyll diesler in the plant material.
- the plant material should have relatively concentrated amounts of the desired xanthophyll in the non free form that is usually and preferably the form of a tatty acid ester. Marigolds are an excellent source of lulein in the form of diesters.
- wolfberry fruit (Lycium barbarum) an excellent source of zeaxanthin diesters
- pepper plant Capsicum annuum an excellent source capsanthin as diesters.
- Other plants and fruils and Vegetables having high concentrations of desired xanthophylls can also be utilized.
- non free form xanthophyll- refers to an xanthophyll that is in a form that can be transesterified to the free form of the xanthophyll.
- the lerm free form xanthophv 11- refers lo an xanthophyll thai is not an in an esterified form.
- the lerm bioavailability- refers to the extent to which the xanthophyll is available to the body of the organism consuming it.
- base refers potassium hydroxide, potassium sorbate, NaOMe, animal liver lipase, NaOEt, KOMe. KOEt, Na 2 CO3, K : C0 3 and such other non-nucleopl ⁇ lic and non-strong kinetically deprotonating material which does not cause kinetic deprotonation in the alpha-position of the carbonyls and highly conjugated double bond systems, for example LDA or BuLi would be excluded from the definition of base because these chemicals cause deprotonation in the alpha-position of the carbonyls and highly conjugated double bond svstems.
- Ratio of Base to plant material (Meal) by Weight- refers to the amount of based used in the reaction compared to the weight of the plant material. This amount is determined by the pH of the reaction and the desired reaction times. Tlie preferred pH is between 11-14: lower pH can be used but increases the reaction time.
- solvent- refers to a chemical in which the transesterification of the xanthophyll can be carried out.
- the chemical preferably has a hydroxyl group.
- the solvent is preferably an alcohol with 1-4 carbons More preferably the solvent is selected to have a boiling point that allows the reaction temperature of the transesterification to be kept at 75-85 degrees C, such as MeOH.
- Plant material refers to plants conlaining xanthophylls in the non free form of the xanthophyll.
- the contemplated plant sources contain xanthophylls in the esterified form as a mono- or di-C ⁇ -Cig long chain fatly acids such as lauric, myrislic, oleic, linolenic and palmitic acids.
- Marigolds are an excellent source of lutein in the form of diesters presently known in nature
- the wolfberry fruit (Lycium barbarum) is an excellent source of zeaxanthin diesters
- Ihe pepper plant Capsicum annuum
- Other plants and fruits and vegetables having high concentrations of desired xanthophylls can be employed.
- the prior art teaches that organic extractors have been used to extract carotenoids from plant material.
- Such extractors include hexane, acetone, petroleum ether, methanol, ethyl acetate, diethyl either, heptanes, chloroform, and tetrahydrofuran. These extractors result in what is called an oleoresin which contains diesters.
- the prior art then teaches the use of a saponification reaction that cleaves the fatty acids from the xanthophyll diesters. There are a number of known methods for the saponification. These produce free form xanthophylls along with soaps of the fatty acids.
- the soaps are made with alkali solutions such as potassium hydroxide and sodium hydroxide in an aqueous solution. Even though similar chemicals may be used in the saponification process clearly the present invention does not require the organic extraction step nor the saponification step to provide an improved plant material.
- diacyl-xanthophylls are converted by transesterification into free xanthophylls in situ (in the crude plant material). This process avoids the cost and processes and potentially hazardous chemicals associated with the production of an oleoresin. Additionally the plant material can act as the carrier material increasing the efficiently of Ihe process.
- the steps of the present method include placing the plant material containing the nonfree form of xanthophylls in the solvent and base.
- Ratio of base to plant material (Meal) by weight is the amount of based used in the reaction compared to the weight of the plant material. This amount is determined by the pH of the reaction and the desired reaction times. The preferred pH is between 11-14: lower pH increases the reaction time.
- the reaction solution was neutralized to a pH of 7 with phosphoric acid Any number of neutralizing acids and agents could be employed. But phosphoric acid is preferred
- the solvent preferably an alcohol and more preferably MeOH was remove with 16 hours of distillation at 69° C. The temperature of distillation can be higher or lower as long as it is above the boiling point of MeOH and the distillation is done in a commercially reasonable lime.
- the residue is dried after the distillation of the solvent either at room temperature at one ATM or by vacuum drying in an oven at a temperature ⁇ 50° C.
- the method of drying is a question of drying time and is nol critical.
- the planl residue material that now has in situ free form xanthophylls therein is mixed and a fine powder with a xanthophyll activity of 10-14 g/kg is achieved.
- the final product is preferably stored al room temperature under nitrogen.
- the following bases can also be used in ihe present invention. Their selection can be based on the economics of the process, the speed of the process and the acceptability of trace amounts of the components.
- the present invention a plant material having free form xanthophylls, can be marigold meal that has been converted
- the converted marigold meal was fed to poultry along with a control (the same marigold meal from Ihe same batch of plant materials) lo the same type and age of egg laying hens.
- the data indicates that there was increased use of the xanthophylls in the converted meal. In other words there was more pigmentation of Ihe yolks of the egg when Ihe same amount of converted plant material was consumed compared to the non converted plant material.
- the process is providing the xanlhophylls in a more bioavailable form lo the animal consuming the product.
- this lesl was run with marigold meal that was processed by the steps as listed below to provide in situ free form xanlhophylls.
- Step 3 The residue was then dried in a well ventilated room at room temperature and at 1 ATM or by means of vacuum drying in an oven (temperature ⁇ 50° C).
- Step 4 After mixing and blending, a fine powder was obtained with a total xanthophyll activity of 10 to 14 g/kg (depending on the duration of the reaction and drying process). The final product is stored at room temperature under nitrogen.
- the process described above can use a number of different bases that include but are not limited to potassium hydroxide, potassium sorbate, NaOMe. animal liver lipase, NaOEt, KOMe, KOEt. Na 2 C ⁇ 3, K CO 3 and such other non-nucleopl ⁇ lic and non-strong kinetically deprotonating material which does not cause deprotonation in the alpha-position of the carbonyls and highly conjugated double bond systems.
- the preferred base is KOH due to its availability at an inexpensive price and its effectiveness in avoiding the issues of deprotonation. The amount to use of other bases is readily determined
- the solvent is an alcohol solvent that further along in the process is removable by distillation.
- MeOH is preferred as a solvent, but olher types of alcohol, such as: isopropyl alcohol, ethanol and butanol and the like can be employed without undue experimentation by the ordinarily skilled person in tlie art.
- Tlie solvent clearly is a chemical in which tlie transeslerificalion of the xanthophyll can be carried out.
- the solvent preferably has a hydroxyl group and is not an aqueous solution.
- the neutralizing agent is preferably phosphoric acid.
- other Lewis acids such as: HCL, Sulfuric acid, AICI3, NHLCL, Acetic acid and the like can be used.
- Plant material refers lo plants conlaining xanlhophylls in the non free form xanthophyll.
- the contemplated plant sources contain xanthophylls in the esterified form as a mono- or di-Ci 2 -C )8 long chain fatty acids such as lauric, myrislic, oleic, linolenic and palmitic acids.
- Xanlliophylls are found in a number of differing plant materials. Marigold has lutein and paprika has capsanlhin. This process works to liberate a number of nonfree form xanthophylls in plant materials.
- the reaction turnover is monitored by HPLC.
- the residue is then dried on standing at rt. at 1 atm, and is followed by vacuum drying in an oven (50° C, 100 Torr) for 2 hours. After mixing a fine powder is obtained with a total xanthophyll activity to be determined per kg (depending on the duration of the drying process and efficacy of Ihe mixing).
- the untreated marigold meal had the following parameters and conditions: Column Pressure (PSI): 2391 Column Temperature (C): N/A
- Tlie graph in Figure 1 shows that the lutein of die marigold meals has a lot of ester activity in the 28-33 range and a lutein level in the 7-8 range.
- the transesterified marigold meal shows that the lutein peak is still high and die esters in the 31-33 area no longer exist.
- the following data was gathered from the marigold meal and Figure 1.
- microAU 5e+001 Drift (microAU/min): le+002 -
- Young Warren SEX-SAL-LINK hens were divided into three identical groups. Each group exists of 7 cages which contain each 3 hens. The pullets have access to feed and water at all times.
- the three groups were given the carrier feed (pigment free food) for 3 weeks as a control for the experiment.
- ORO GloTM a commercially available free form of lutein available form Kemin Industries, Inc. Des Moines, IA.
- Group B will be fed the new invenlion made according lo the process of experiment one (7.5mg of lulein activity per Kg of feed).
- Group C will be fed the new invenlion made according lo Ihe process of experiment one (15.0mg of lutein activity per Kg of feed). The experiment was run for 28 days. The feeding of the material requires 3 to 5 days before the effects on the yolk color are visible. Yolk color is uniform and consistent after approximately 21 days of feeding, ten ( 10) randomly chosen eggs laid by each group at day 0, 2, 4, 8, 16 and day 28 were broken and the egg yolk color was measured and the total amount of feed intake was determined on the 28th day. At days 0, 16 and day 28 the egg yolk of 3 randomly chosen eggs laid by each group had to be blended and weighed, followed by extraction and analysis of the egg yolk from each group.
- Figure 5 shows the Roche fan scale over days for the egg yolk color of die present invention and of die commercial product.
- Figure 6 shows die mg/Kg of xanthophylls in the egg yolks over days of the three treatments. The results show that the plant material is providing more pigment and color at the 15 mg level then is the commercial product. The 15mg level appears to be a more effective level then the 7.5 mg level. The lower level is providing less egg yolk color even though die egg appears to have more xanthophylls from the plant material in the egg yolk than die commercial product.
Abstract
Description
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Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/856,357 US5876782A (en) | 1997-05-14 | 1997-05-14 | Method for the conversion of xanthophylls in plant material |
PCT/US1998/016393 WO2000007458A1 (en) | 1997-05-14 | 1998-08-05 | Method for the conversion of xanthophylls in plant material |
CN988142368A CN1217586C (en) | 1997-05-14 | 1998-08-05 | Method for the conversion of xanthophylls in plant material |
JP2000563150A JP2002522038A (en) | 1998-08-05 | 1998-08-05 | Xanthophyll conversion method in plant material |
AU86951/98A AU759532B2 (en) | 1998-08-05 | 1998-08-05 | Method for the conversion of xanthophylls in plant material |
EP98938424A EP1102545A4 (en) | 1998-08-05 | 1998-08-05 | Method for the conversion of xanthophylls in plant material |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US08/856,357 US5876782A (en) | 1997-05-14 | 1997-05-14 | Method for the conversion of xanthophylls in plant material |
PCT/US1998/016393 WO2000007458A1 (en) | 1997-05-14 | 1998-08-05 | Method for the conversion of xanthophylls in plant material |
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WO2000007458A1 true WO2000007458A1 (en) | 2000-02-17 |
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CN (1) | CN1217586C (en) |
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US6811801B2 (en) | 2001-12-12 | 2004-11-02 | Abbott Laboratories | Methods and compositions for brightening the color of thermally processed nutritionals |
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PE130499A1 (en) * | 1997-10-31 | 1999-12-17 | Bioquimex Reka S A De C V | PROCEDURE FOR THE ISOMERIZATION OF LUTEIN TO ZEAXANTINE AND THE PRODUCT OBTAINED THEREOF |
US6191293B1 (en) | 1998-04-20 | 2001-02-20 | Inexa, Industria Extractora C.A. | Trans-xanthophyll ester concentrates of enhanced purity and methods of making same |
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US6504067B1 (en) * | 1999-11-24 | 2003-01-07 | Industrial Organica S.A. De C.V. | Process to obtain xanthophyll concentrates of high purity |
US6169217B1 (en) | 1999-10-20 | 2001-01-02 | Board Of Trustees Of The University Of Illinois | Method for extracting xanthophylls from corn |
US6797303B2 (en) * | 2001-09-04 | 2004-09-28 | Lycored Natural Products Industries Ltd. | Carotenoid extraction process |
AU2002234248A1 (en) | 2001-11-29 | 2003-06-17 | University Of Maryland | Process for extraction and purification of lutein, zeaxanthin and rare carotenoids from marigold flowers and plants |
CN1309693C (en) * | 2002-02-05 | 2007-04-11 | 海宁凤鸣叶绿素有限公司 | Lutein crystal preparing process from marigold flower |
ES2312779T3 (en) * | 2002-03-26 | 2009-03-01 | Dsm Ip Assets B.V. | ESTERIFICATION OF XANTOFILAS. |
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MXPA05001202A (en) * | 2002-07-29 | 2005-11-23 | Hawaii Biotech Inc | Structural carotenoid analogs for the inhibition and amelioration of disease. |
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US20050148517A1 (en) * | 2002-07-29 | 2005-07-07 | Lockwood Samuel F. | Carotenoid ether analogs or derivatives for controlling connexin 43 expression |
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CN100337602C (en) * | 2001-06-15 | 2007-09-19 | 卡尔蔡司医疗技术股份公司 | Method and apparatus for removal of material |
US6811801B2 (en) | 2001-12-12 | 2004-11-02 | Abbott Laboratories | Methods and compositions for brightening the color of thermally processed nutritionals |
Also Published As
Publication number | Publication date |
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CN1217586C (en) | 2005-09-07 |
US5876782A (en) | 1999-03-02 |
CN1310584A (en) | 2001-08-29 |
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