WO2018029338A1 - Procédé de production d'un pigment bleu de gardénia à partir de géniposide - Google Patents

Procédé de production d'un pigment bleu de gardénia à partir de géniposide Download PDF

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Publication number
WO2018029338A1
WO2018029338A1 PCT/EP2017/070421 EP2017070421W WO2018029338A1 WO 2018029338 A1 WO2018029338 A1 WO 2018029338A1 EP 2017070421 W EP2017070421 W EP 2017070421W WO 2018029338 A1 WO2018029338 A1 WO 2018029338A1
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WIPO (PCT)
Prior art keywords
process according
genipin
blue pigment
gardenia blue
solvent
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PCT/EP2017/070421
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English (en)
Inventor
Quing HE
Xiaoping Huang
Xiaojia HU
Kun Peng
Zhibin Zhu
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Dsm Ip Assets B.V.
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Publication of WO2018029338A1 publication Critical patent/WO2018029338A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/16—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing two or more hetero rings
    • 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
    • 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
    • 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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0096—Purification; Precipitation; Filtration

Definitions

  • the present invention is related to an improved process for producing a natural pigment.
  • the present invention is related to an improved process for producing the gardenia blue pigment.
  • the gardenia blue pigment is a water-soluble natural pigment widely used in food, pharmaceutical and cosmetics industries.
  • the gardenia blue pigment is usually produced from the raw material geniposide contained in Gardenia Jasminoides Ellis of Rubiaceae by the process of treating geniposide with a ⁇ -glucosidase to obtain genipin which reacts with an amino acid to obtain the gardenia blue pigment, (see Shijing WU, ei al., National Food Additive Communications, 1992 (3): 90-93)
  • the gardenia blue pigment obtained by this process is dark, it has a low color value and is of low quality.
  • the color reaction time of the process is long (10-50 hours). Accordingly, it is not suitable for industrial applications, (see e.g. CN103509368A and CN102021210A)
  • Feng CHEN discloses a process for producing the gardenia blue pigment with a high color value, which comprises ultra-filtering the gardenia blue pigment obtained from the reaction of genipin with an amino acid to remove the residual geniposide and then extracting the filtrate to obtain the gardenia blue pigment of a high color value (see CN103525883A).
  • Lijun SUN ei al. discloses another process, which comprises passing the raw material geniposide through a large mesh non- polar resin to remove a-crocin before treating it with ⁇ -glucosidase. (Lijun SUN ei al., Journal of Nanjing Agricultural University, 1994, 17(4): 98-101)
  • these processes involve high cost and complicated operations, and are not suitable for being carried out at large scale in industry.
  • the present invention provides an improved process for producing a gardenia blue pigment, comprising the following steps:
  • step a) Treating geniposide with a glycosidase to obtain a hydrolysate; and b) Extracting the hydrolysate obtained in step a) with a solvent and removing the solvent after the extraction to obtain a product comprising genipin;
  • step b) Reacting the product comprising genipin obtained in step b) with an amino acid and/or a salt thereof under an atmosphere of inert gas, and
  • step d) Introducing oxygen after genipin is consumed to produce the gardenia blue pigment; and e) Optionally, purifying the gardenia blue pigment produced in step d).
  • the process of the present invention is easy-to-workup and thus suitable for manufacture in the industry.
  • the obtained ga rdenia blue pigment is sky blue, brighter than the blue such as ultramarine blue produced by the known processes, and it has a color va lue of >100, so it is suitable for industrial applications.
  • the present invention provides a process for producing the ga rdenia blue pigment which is sky blue and may have a color va lue of >100.
  • the process of the present invention comprises the following steps:
  • step b) Extracting the hydrolysate obtained in step a) with a solvent and removing the solvent after the extraction to obtain a product comprising genipin;
  • step b) Reacting the product comprising genipin obtained in step b) with an amino acid and/or a salt thereof under an atmosphere of inert gas, and
  • step d) Introducing oxygen after genipin is consumed to produce the gardenia blue pigment; and e) Optionally, purifying the gardenia blue pigment produced in step d).
  • the geniposide used as raw material may be from various sou rces. It may be obta ined by extracting the fruit Gardenia Jasminoides Ellis by any known process, for example, that as d isclosed in Chinese patent publication CN 102732050A.
  • gen iposide powders which contain about 20wt% to about 70wt% of geniposide and are commercially available, and the waste stream from the gardenia yellow production, wh ich conta ins about 40wt% of geniposide and is also commercially available, may be used into the process directly or after simple refining, (see CN 103509368A, CN 103525883A etc.)
  • the glycosidase is an enzyme under EC 3.2.1 according to the Recommendations of the Nomenclature Committee of the International Union of Biochemistry and Molecular Biology on the Nomenclature and Classification of Enzymes by the Reactions they Catalyse.
  • the glycosidase is cellulase (EC 3.2.1.4) and ⁇ -glucosidase (EC 3.2.1.21).
  • the examples of the glycosidase include but a re not limited to cellobiase commercially available from Sunson Biotechnology Co. Ltd . (Guangzhou, China), Cellulase 4000 commercially available from DSM (China) Ltd.
  • the glycosidase may be added into the reaction of the step a) in an amount in the range of from 0.01 g to 1.0 g, preferably in an amount in the range of from 0.1 g to 0.9 g, more preferably in an amount in the range of from 0.3 g to 0.8 g, per 1 g of geniposide.
  • the treatment of the step a) may be carried out at a pH in the range of from 3.0 to 6.5, preferably at a pH in the range of from 3.6 to 6.0, and more preferably at a pH in the range of from 4.0 to 4.6.
  • the treatment of the step a) is carried out in a buffer solution which can provide the above pH ranges.
  • buffer solution is known in the art, and the examples include but are not limited to an aqueous HCOOH/NaOAc solution or an aqueous citric acid/Na 2 HP0 4 solution.
  • the buffer solution may be added in an amount in the range of from 8 mL to 80 mL, preferably in an amount in the range of from 10 mL to 70 mL, more preferably in an amount in the range of from 15 mL to 50 mL, per 1 g of geniposide.
  • the treatment of the step a) may be carried out at a temperature in the range of from about 20°C to about 60°C, preferably at a temperature of about 50°C.
  • the reaction of the step a) may last about 2 hours to about 30 hours, preferably 4 hours to 10 hours, and more preferably less than 8 hours.
  • the obtained hydrolysate contains genipin as main component and other components.
  • the hydrolysate can be used for the extraction in step b) directly.
  • the hydrolysate obtained from the step a) is normally reacted with an amino acid directly to produce gardenia blue pigment.
  • the gardenia blue pigment obtained from the prior process is dark and not good for some industrial applications such as beverages.
  • the inventors of the present invention surprisingly discovered that an additional extraction of the step b) results in sky blue color, a bright blue pigment which is more applicable for industrial applications like beverages.
  • the solvent used for extraction in the step b) is important and may be any one suitable for the purpose of the invention, and examples include but are not limited to diethyl ether, ethyl acetate, butanol, a mixture of butanol with petroleum and/or hexane, or mixtures thereof.
  • the solvent is a mixture of butanol with petroleum and/or hexane
  • the volume ratio of butanol with petroleum and/or hexane is in the range of from 1:5 to 5:1, preferably in the range of from 1:3 to 3:1, and more preferably in the range of from 1:2 to 2:1.
  • the solvent used in the step b) is ethyl acetate.
  • the amount of the solvent used in the step b) may be from 0.5 mL to 5 mL, preferably from 1.0 mL to 3 mL, per 1 mL of the hydrolysate.
  • the extraction of the step b) may be carried out at a temperature in the range of from 10°C to 60°C, preferably at room temperature. According to the present invention, the extraction of the step b) may be repeated two to four times.
  • the product comprising genipin is obtained after the organic phases are collected and the solvent is removed in the step b).
  • the solvent may also be recycled.
  • the extraction procedures and the procedures for collecting solvents and removing/recycling solvents during the extraction are known to the person skilled in the art. Therefore, they are not discussed in more detail here.
  • genipin reacts with an amino acid or a salt thereof in one step to provide gardenia blue pigment.
  • the present invention provides an improved process with a two-steps color reaction to produce the gardenia blue pigment.
  • steps c) and d) of the process of the present invention the product comprising genipin obtained in the step b) is reacted with an amino acid or a salt thereof under an atmosphere of inert gas at first, and then oxygen is introduced after the genipin is consumed to produce the gardenia blue pigment.
  • the process of the present invention provides more consistent and stable gardenia blue pigment with higher color value, and the color reaction time is reduced significantly from more than 30 hours to less than 10 hours.
  • the amino acid may be selected from the group consisting of glutamate, phenylalanine, histidine, leucine, isoleucine, arginine and mixture thereof.
  • the salt may be any alkali metal salt such as sodium salt.
  • the salt is sodium glutamate.
  • the amino acid and the salt used in the step c) are also important because they can provide sky blue color as disclosed in the present invention.
  • the amino acid used in the step c) is sodium glutamate.
  • the amino acid may be added in an amount of 0.5-10 moles, preferably 0.8-6 moles, and more preferably 1-3 moles, per 1 mole of genipin in the reaction.
  • the amino acid is added in an aqueous solution.
  • the product comprising genipin obtained from the step b) is dissolved in a water-soluble solvent to react with the amino acid in the step c).
  • the water-soluble solvent may be any one known in the art that can dissolve the product comprising genipin and examples include but are not limited to Ci-io alkanols such as methanol and ethanol, and C3-10 ketones such as acetone.
  • the water-soluble solvent is methanol, ethanol or acetone or any mixture thereof.
  • the product comprising genipin obtained from the step b) is reacted with an aqueous solution of the amino acid in the absence of any organic solvent in the step c). No organic solvent process would be preferred in the industry because of safety advantage and others like easy-to-workup, reduced organic solvent residue and low cost.
  • the inert gas used in step c) may be any gas that cannot react with any material in the reaction liquid.
  • the example of the inert gas includes but is not limited to nitrogen gas, argon gas and helium gas.
  • the reaction of the step c) may be carried out at about 30°C to about 100°C, preferably about 60°C to 80°C, such as 60°C, 65°C, 70°C and 75°C.
  • the progress of the reaction can be monitored by any known method, such as H PLC and TLC.
  • the step c) is carried out at a pH value in the range of from 7.0 to 11.
  • a base selected from but not limited to NaOH, KOH, NaC0 3 and NaHC0 3 is added to adjust the reaction mixture of the step c) to an appropriate pH value.
  • oxygen is introduced into the reaction liquid to produce the gardenia blue pigment as step d) of the present invention.
  • the oxygen may be introduced as pure oxygen, air and/or diluted oxygen or air.
  • the oxygen is introduced as air.
  • the reaction of the step d) of the present invention may continue till the desired gardenia blue is obtained.
  • the reaction lasts from 4 hours to 20 hours, more preferable from 6 hours to 15 hours, under the same range of temperature as the step c).
  • the reaction may be terminated or quenched by any know method in the art, for example, by introducing vacuum or inert gas when the desired gardenia blue is obtained.
  • the gardenia blue pigment can be obtained as a solid by removing the organic solvent and water in the reaction mixture. Accordingly, the process of the present invention optionally further comprises the step of removing the solvent and water to provide a solid of the gardenia blue pigment by, for example, lyophilization or spray drying.
  • the obtained gardenia blue pigment can be purified further by any procedures known in the art such as ultrafiltration to obtain an even purer gardenia blue pigment.
  • the process of the present invention produces the gardenia blue pigment which is sky blue, brighter than the blue color such as ultramarine blue produced by the known processes and thus more popular for some industrial applications such as beverages.
  • the obtained gardenia blue pigment of the present invention has a color value of >100, that means low dosage is needed in applications and more stable in beverage. Further, by an additional extraction step, the obtained gardenia blue pigments can be easily separated and purified from the reaction mixture without complicated operations. Furthermore, by the two- steps color reaction, the process of the present invention becomes easy-to-workup and has reduced reaction time, and the obtained gardenia blue pigment is more consistent.
  • color (lightness, chroma, and hue) of the gardenia blue pigment is determined with a HunterLab Ultra Scan Pro spectrocolorimeter (Hunter Associates Laboratory, Reston, VA, USA) and expressed on basis of the CIELAB color scale.
  • the mode used is RSIN which stands for Reflectance - Specular Included.
  • the small area view (SAV) with a diameter of 4.826 mm (0.190 inch) is chosen. Color measurements are carried out after CIE guidelines
  • Chroma sometimes called saturation describes the vividness or dullness of a color which can be calculated as followed:
  • the maximum absorption wavelength (A max ) and the color value are measured according to the national standard GB 28311-2012 of China.
  • the combined organic phase was concentrated under vacuum to remove part of ethyl acetate to left 150 L of ethyl acetate solution. 730 ml of the ethyl acetate solution was further precipitated at about 50°C, 200 mbar to offer 38.3 g crude genipin powder with 91.15% HPLC purity.
  • Example 4 - comparative Ltd.(Xi'an, China) was added into 64 ml of an aqueous citric acid/Na 2 HP0 4 buffer solution (pH 4.6). 240 mg of Cellulase 4000 purchased from DSM (China) Ltd. (Shanghai, China ) was further added for reaction for 24 hours at 50°C. Then 2.0 g of sodium glutamate was added into the reaction mixture for 96 hours at 50°C.
  • the reaction mixture was filtered, purified by ultrafiltration, and then lyophilized to obtain 2.8 g of gardenia blue pigment as solid powder, with a maximum absorption wavelength of 591 nm and a color value of 11.25.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
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Abstract

L'invention concerne un procédé de production du pigment bleu de gardénia comprenant le traitement de géniposide avec une glycosidase pour obtenir un hydrolysat, l'extraction de l'hydrolysat avec un solvant et l'élimination du solvant après l'extraction pour obtenir un produit comprenant de la génipine, la réaction du produit comprenant de la génipine avec un acide aminé et/ou un sel de celui-ci dans une atmosphère de gaz inerte, et l'introduction d'oxygène après la consommation de la génipine pour produire le pigment bleu de gardénia. Le procédé est facile à mettre en œuvre et convient à l'industrie et le pigment bleu de gardénia obtenu est lumineux et convient à une application industrielle.
PCT/EP2017/070421 2016-08-12 2017-08-11 Procédé de production d'un pigment bleu de gardénia à partir de géniposide WO2018029338A1 (fr)

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CNPCT/CN2016/095058 2016-08-12

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020213448A1 (fr) * 2019-04-16 2020-10-22 グリコ栄養食品株式会社 Pigment bleu de gardénia et procédé pour la production de celui-ci
WO2020213447A1 (fr) * 2019-04-16 2020-10-22 グリコ栄養食品株式会社 Pigment bleu de gardénia et son procédé de production
CN113402460A (zh) * 2021-05-10 2021-09-17 南京中医药大学 一种具有抗精神类疾病的栀子蓝色素及其制备方法与应用
WO2022044291A1 (fr) * 2020-08-28 2022-03-03 グリコ栄養食品株式会社 Pigment bleu et son procédé de production
EP4203708A4 (fr) * 2020-08-26 2024-10-09 Archer Daniels Midland Company Procédés de production de colorants de diverses teintes à partir de fruit de huito

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115223782B (zh) * 2022-07-26 2024-07-16 西安交通大学 一种分数匝平面变压器及变换器

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102021210A (zh) 2009-09-18 2011-04-20 桂林莱茵生物科技股份有限公司 一种栀子蓝色素的制备方法
CN102732050A (zh) 2012-06-06 2012-10-17 浙江科技学院 一种从栀子中制备栀子色素的方法
WO2013070682A1 (fr) * 2011-11-07 2013-05-16 Wild Flavors, Inc. Matériau riche en génipine et son utilisation
CN103509368A (zh) 2013-10-09 2014-01-15 邵阳学院 超临界co2催化栀子苷水解制备栀子蓝色素的方法
CN103525883A (zh) 2013-10-23 2014-01-22 宁德师范学院 一种制备高色价栀子蓝色素的方法
WO2016041500A1 (fr) * 2014-09-17 2016-03-24 Dsm Ip Assets B.V. Procédé de production de pigment bleu de gardénia
CN105624198A (zh) * 2016-03-10 2016-06-01 河南中大恒源生物科技股份有限公司 一种制备不同色调高纯度栀子蓝色素的工艺

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102021210A (zh) 2009-09-18 2011-04-20 桂林莱茵生物科技股份有限公司 一种栀子蓝色素的制备方法
WO2013070682A1 (fr) * 2011-11-07 2013-05-16 Wild Flavors, Inc. Matériau riche en génipine et son utilisation
CN102732050A (zh) 2012-06-06 2012-10-17 浙江科技学院 一种从栀子中制备栀子色素的方法
CN103509368A (zh) 2013-10-09 2014-01-15 邵阳学院 超临界co2催化栀子苷水解制备栀子蓝色素的方法
CN103525883A (zh) 2013-10-23 2014-01-22 宁德师范学院 一种制备高色价栀子蓝色素的方法
WO2016041500A1 (fr) * 2014-09-17 2016-03-24 Dsm Ip Assets B.V. Procédé de production de pigment bleu de gardénia
CN105624198A (zh) * 2016-03-10 2016-06-01 河南中大恒源生物科技股份有限公司 一种制备不同色调高纯度栀子蓝色素的工艺

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
LIJUN SUN ET AL., JOURNAL OF NANJING AGRICULTURAL UNIVERSITY, vol. 17, no. 4, 1994, pages 98 - 101
SHIJING WU, NATIONAL FOOD ADDITIVE COMMUNICATIONS, vol. 3, 1992, pages 90 - 93

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020213448A1 (fr) * 2019-04-16 2020-10-22 グリコ栄養食品株式会社 Pigment bleu de gardénia et procédé pour la production de celui-ci
WO2020213447A1 (fr) * 2019-04-16 2020-10-22 グリコ栄養食品株式会社 Pigment bleu de gardénia et son procédé de production
EP3957690A4 (fr) * 2019-04-16 2023-01-25 Glico Nutrition Co., Ltd. Pigment bleu de gardénia et procédé pour la production de celui-ci
EP3957689A4 (fr) * 2019-04-16 2023-01-25 Glico Nutrition Co., Ltd. Pigment bleu de gardénia et son procédé de production
JP7558154B2 (ja) 2019-04-16 2024-09-30 グリコ栄養食品株式会社 クチナシ青色素及びその製造方法
EP4203708A4 (fr) * 2020-08-26 2024-10-09 Archer Daniels Midland Company Procédés de production de colorants de diverses teintes à partir de fruit de huito
WO2022044291A1 (fr) * 2020-08-28 2022-03-03 グリコ栄養食品株式会社 Pigment bleu et son procédé de production
EP4206288A1 (fr) * 2020-08-28 2023-07-05 Glico Nutrition Co., Ltd. Pigment bleu et son procédé de production
EP4206288A4 (fr) * 2020-08-28 2024-09-18 Glico Nutrition Co Ltd Pigment bleu et son procédé de production
CN113402460A (zh) * 2021-05-10 2021-09-17 南京中医药大学 一种具有抗精神类疾病的栀子蓝色素及其制备方法与应用

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