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WO1994013743A1 - Procede d'isolation d'oleoresines vegetales pouvant etre obtenues par extraction par hexane - Google Patents

Procede d'isolation d'oleoresines vegetales pouvant etre obtenues par extraction par hexane Download PDF

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Publication number
WO1994013743A1
WO1994013743A1 PCT/DK1993/000422 DK9300422W WO9413743A1 WO 1994013743 A1 WO1994013743 A1 WO 1994013743A1 DK 9300422 W DK9300422 W DK 9300422W WO 9413743 A1 WO9413743 A1 WO 9413743A1
Authority
WO
WIPO (PCT)
Prior art keywords
fact
starting products
cell wall
degrading enzyme
wall degrading
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.)
Ceased
Application number
PCT/DK1993/000422
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English (en)
Inventor
Klaus Pommer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novo Nordisk AS
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Novo Nordisk AS
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Filing date
Publication date
Application filed by Novo Nordisk AS filed Critical Novo Nordisk AS
Publication of WO1994013743A1 publication Critical patent/WO1994013743A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y302/00—Hydrolases acting on glycosyl compounds, i.e. glycosylases (3.2)
    • C12Y302/01—Glycosidases, i.e. enzymes hydrolysing O- and S-glycosyl compounds (3.2.1)
    • 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
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B1/00—Production of fats or fatty oils from raw materials
    • C11B1/10—Production of fats or fatty oils from raw materials by extracting
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y302/00—Hydrolases acting on glycosyl compounds, i.e. glycosylases (3.2)
    • C12Y302/01—Glycosidases, i.e. enzymes hydrolysing O- and S-glycosyl compounds (3.2.1)
    • C12Y302/01004—Cellulase (3.2.1.4), i.e. endo-1,4-beta-glucanase
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y302/00—Hydrolases acting on glycosyl compounds, i.e. glycosylases (3.2)
    • C12Y302/01—Glycosidases, i.e. enzymes hydrolysing O- and S-glycosyl compounds (3.2.1)
    • C12Y302/01015—Polygalacturonase (3.2.1.15)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y302/00—Hydrolases acting on glycosyl compounds, i.e. glycosylases (3.2)
    • C12Y302/01—Glycosidases, i.e. enzymes hydrolysing O- and S-glycosyl compounds (3.2.1)
    • C12Y302/01022—Alpha-galactosidase (3.2.1.22)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y302/00—Hydrolases acting on glycosyl compounds, i.e. glycosylases (3.2)
    • C12Y302/01—Glycosidases, i.e. enzymes hydrolysing O- and S-glycosyl compounds (3.2.1)
    • C12Y302/01032—Xylan endo-1,3-beta-xylosidase (3.2.1.32), i.e. endo-1-3-beta-xylanase
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y304/00—Hydrolases acting on peptide bonds, i.e. peptidases (3.4)
    • C12Y304/21—Serine endopeptidases (3.4.21)
    • C12Y304/21004—Trypsin (3.4.21.4)

Definitions

  • the invention comprises a method for isolation of vegetable oleoresins producible by hexane extraction.
  • vegetable oleoresins are plant pigments, such as the yellow pigment oleoresin from Tagetes erect , carotenoides from carrots and spices, such as pebber or paprika oleoresins.
  • plant pigments such as the yellow pigment oleoresin from Tagetes erect , carotenoides from carrots and spices, such as pebber or paprika oleoresins.
  • the purpose of the invention can be fulfilled, if the extraction is carried out with a mixture of water and an organic acid immiscible with water under specified conditions. It is most surprising that the method according to the invention exhibits both the advantage that it does not use volatile solvents or other environmentally dangerous processes, and the advantage that the wanted oleoresins are produced in a yield not less than the yield of the oleoresins if produced conventionally. Actually it has been found that the yield of the oleoresins produced by means of the method according to the invention is of the order of magnitude 70%, whereas the yield of the oleoresins produced conventionally is of the order of magnitude 60%.
  • an organic acid immiscible with water is to be understood as an organic acid, of which the part thereof which exists as acid in an equilibrated mixture of water and organic acid is present in a concentration of less than 1 % in the water phase at a pH below 5.5.
  • organic acids with less than around 6 carbon atoms are not classified as organic acids immiscible with water in the sense of this invention.
  • the organic acid immiscible with water should be fluid at reaction temperature (usually around 40-60°C), and should preferably exhibit relatively low viscosity. This means that organic acids with more than around 12 carbon atoms are not well suited for the invention.
  • step 2) the separated organic phase from step 2) is mixed with fresh water, whereafter pH is adjusted to a value above 8.0, whereby the extracted vegetable oleoresins are liberated, and
  • the vegetable starting products in relation to the method according to the invention preferably should be comminuted to a particle size of less than 5 mm, more preferable less than 2 mm.
  • the final products i.e. the vegetable oleoresins
  • This product can be further purified and/or dried, if necessary.
  • a preferred embodiment of the method according to the invention is characterized by the fact that the vegetable starting products are annato seeds, paprika, rhizome of Curcuma longa, Tagetes erecta, lucerne, carrots, tomatoes (all pigments), paprika, pepper, tumeric, ginger, cinnamon, cassia, nutmeg, mace, clove, pimento, or cardamon (all spices). These are the most common vegetable starting products. Also, waste of the above indicated vegetables are included as starting products in the method according to the invention, especially carrot waste.
  • a preferred embodiment of the method according to the invention is characterized by the fact that the organic acid immiscible with water is a straight chain, saturated fatty acid with a total number of C atoms between 6 and 12, inclusive, preferably between 8 and 10, inclusive. If the total number of C atoms in the organic acid is below 6, the smell of the organic acid is unagreeably strong, and
  • a preferred embodiment of the method according to the invention is characterized by the fact that during step 1) a cell wall degrading enzyme is added.
  • a preferred embodiment of the method according to the invention is characterized by the fact that the cell wall degrading enzyme is SPS-ase, which is preferably added in an amount corresponding to between 25 and 2500 SPS-ase
  • dry vegetable starting products does not mean that the vegetable starting products used in the method according to the invention are dried. If the enzyme is used in an activity less than the above indicated minimum amount, the effect of the enzyme will be negligible during a reasonable time, and if the enzyme is used in an amount above the above
  • the SPS- ase activity unit is defined in AF 201.
  • a preferred embodiment of the method according to the invention is characterized by the fact that the cell wall degrading enzyme is a pentosanase, which is preferably added in an amount corresponding to between 3600 and
  • the pentosanase activity unit PTU is defined in AF 284.
  • a preferred embodiment of the method according to the invention is characterized by the fact that the cell wall degrading enzyme is a xylanase, which is preferably added in an amount corresponding to between 360 and 36,000 xylanase activity units/kg of dry vegetable starting products.
  • the xylanase activity unit EXU is defined in AF 293.9.
  • a preferred embodiment of the method according to the invention is characterized by the fact that the cell wall degrading enzyme is a celiulase, which is preferably added in an amount corresponding to between 900 and 90,000 celiulase activity units/kg of dry vegetable starting products. If the enzyme is used in an activity less than the above indicated minimum amount, the effect of the enzyme will be negligible during a reasonable time, and if the enzyme is used in an amount above the above indicated maximum amount, the method will be commercially unattractive.
  • the celiulase activity unit NCU is defined in AF 174.
  • a preferred embodiment of the method according to the invention is characterized by the fact that the cell wall degrading enzyme is a protease, which is preferably added in an amount corresponding to between 1.2 and 120 protease activity units/kg of dry vegetable starting products, preferably Neutrase ® . If the enzyme is used in an activity less than the above indicated minimum amount, the effect of the enzyme will be negligible during a reasonable time, and if the enzyme is used in an amount above the above indicated maximum amount, the method will be commercially unattractive.
  • the protease activity unit AU is defined in AF 4.
  • a preferred embodiment of the method according to the invention is characterized by the fact that the cell wall degrading enzyme is galactomannase, which is preferably added in an amount corresponding to between 900 and 90,000 gammanase activity units/kg of dry vegetable starting products. If the enzyme is used in an activity less than the above indicated minimum amount, the effect of the enzyme will be negligible during a reasonable time, and if the enzyme is used in an amount above the above indicated maximum amount, the method will be commercially unattractive.
  • the galactomannase activity unit KVHCU is defined in AF 156.
  • a preferred embodiment of the method according to the invention is characterized by the fact that the cell wall degrading enzyme is a pectinase, which is preferably added in an amount corresponding to between 7200 and 72,000 pectinase activity units/kg of dry vegetable starting products. If the enzyme is used in an activity less than the above indicated minimum amount, the effect of the enzyme will be negligible during a reasonable time, and if the enzyme is used in an amount above the above indicated maximum amount, the method will be commercially unattractive.
  • the pectinase activity unit PSU is defined in AF 269.
  • a preferred embodiment of the method according to the invention is characterized by the fact that the cell wall degrading enzyme is a 0-glucanase, which is preferably added in an amount corresponding to between 60 and 6000 ⁇ - glucanase activity units/kg of dry vegetable starting products. If the enzyme is used in an activity less than the above indicated minimum amount, the effect of the enzyme will be negligible during a reasonable time, and if the enzyme is used in an amount above the above indicated maximum amount, the method will be commercially unattractive.
  • the 0-glucanase activity unit FBU is defined in AF 70. It is to be understood that the invention can be carried out without any enzymes as auxiliary process aids or with one of the above enzymes as an auxiliary process aid or with any combination of two or more of the above enzymes as auxiliary process aids.
  • a preferred embodiment of the method according to the invention is characterized by the fact that the separation in step 2) is carried out by means of a three phase decanter centrifuge. This is a cheap and effective separation, which can be carried out in one single step.
  • a preferred embodiment of the method according to the invention is characterized by the fact that the separation in step 4) is carried out by centrifugation. This separation is rapid and effective.
  • a preferred embodiment of the method according to the invention is characterized by the fact that the following two supplementary reaction steps are carried out after step 4):
  • step 5) the alkaline phase from step 4) is reacidified to a pH value of below 5 4.0, whereby an acid phase is formed, and
  • step 6) the acid phase from step 5) is separated and reused as the organic acid in step 1) for a following extraction.
  • the content of lutein in the organic phase was determined by 0 spectrophotometric analysis at 474 nm, by means of petroleum ether and according to the following equation, reference being made to Handbook of U.S. Colorants, Third Edition, 1991, page 248 (recalculated to mg of lutein/g of organic phase).
  • LT is the total amount of lutein, here the concentration of lutein in mg/g, the dilution is indicated in ml, and the sample weight is indicated in g.
  • the factor 2360 is the absorptivity for lutein in petroleum ether, in L/cm.
  • Tagetes erecta contains 162.8 mg Lutein.
  • the total lutein extracted LT x 45 mg
  • the extraction efficiency _ LT x 45 x 100%
  • the extraction was carried out for 60 minutes under thorough agitation, and subsequently the mixtures were heated to 80°C and held at this temperature for 10 10 minutes in order to inactivate the enzymes.
  • the organic top phase (I) was isolated and mixed with 2 parts of deionized water.
  • the pH was adjusted to pH 9.0 with 15 potassium hydroxide, and the whole mixture was centrifuged again at 4,000 RPM in a Heraeus Labofuge centrifuge type 2202 for 5 minutes.
  • the top layer (oleoresin type) was collected and air dried (II).
  • the water phase was reacidified to pH 4.0 with hydrochloric acid.
  • the organic top layer (III) was isolated by centrifugation for 5 minutes in a Heraeus Labofuge centrifuge type 2202, and thus it can be reused in 0 future extractions.
  • the content of lutein in the organic phase was determined by spectrophotometric analysis at 474 nm, by means of petroleum ether and according to the following equation, reference being made to Handbook of U.S. Colorants, Third Edition, 1991 , page 248 (recalculated to mg of lutein/g of organic phase).:
  • LT is the total amount of lutein, here the concentration of lutein in mg/g, the dilution is indicated in ml, and the sample weight is indicated in g.
  • the factor 2360 is the absorptivity for lutein in petroleum ether, in L/cm. Results:
  • Tagetes erecta contains 162.8 mg of lutein.
  • Total lutein, I LT (I) x 45
  • SPS-ase provides better extraction yields than water, whereas the use of protease provides better product separation than water.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Zoology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

On produit des oléorésines végétales par extraction de produits de départ végétaux comprenant les oléorésines et un mélange d'eau et d'un acide organique immiscible avec de l'eau. De cette manière, on évite l'utilisation de l'hexane ou d'autres solvants nuisibles pour l'environnement, et le rendement en oléorésines est amélioré.
PCT/DK1993/000422 1992-12-17 1993-12-16 Procede d'isolation d'oleoresines vegetales pouvant etre obtenues par extraction par hexane Ceased WO1994013743A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DK151092 1992-12-17
DK1510/92 1992-12-17

Publications (1)

Publication Number Publication Date
WO1994013743A1 true WO1994013743A1 (fr) 1994-06-23

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Application Number Title Priority Date Filing Date
PCT/DK1993/000422 Ceased WO1994013743A1 (fr) 1992-12-17 1993-12-16 Procede d'isolation d'oleoresines vegetales pouvant etre obtenues par extraction par hexane

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0839037A4 (fr) * 1995-07-14 1999-03-03 Sabinsa Corp Composition bioprotectrice, son procede d'utilisation et procede d'extraction de curcuminoides
US6156360A (en) * 1997-09-27 2000-12-05 General Mills, Inc. Stabilized annatto-caramel food colorant
WO2002098530A3 (fr) * 2001-06-06 2003-04-24 Naturel Corp Llc Procede a basse temperature d'extraction de composes principaux provenant de vegetaux ou de matieres vegetales et d'extraits vegetaux ainsi produits
WO2005103212A1 (fr) * 2004-04-23 2005-11-03 Nicolaas Daniel Lombard Burger Procede et appareil utilises dans l'extraction de l'huile vegetale
WO2009060482A1 (fr) * 2007-11-06 2009-05-14 Pectine Industria S.P.A. Procédé d'extraction de caroténoïdes de matières végétales
CN103073915A (zh) * 2013-02-07 2013-05-01 湖南威嘉生物科技有限公司 一种生物酶处理提取分离辣椒红色素和辣椒碱的工艺
CN113583471A (zh) * 2021-09-17 2021-11-02 云南博瑞生物科技有限公司 工业化生产高品质辣椒红色素的方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0113165A1 (fr) * 1982-09-28 1984-07-11 Imperial Biotechnology Limited Extraction d'huiles et de protéines végétales à partir de graines
WO1991013956A1 (fr) * 1990-03-06 1991-09-19 Öljynpuristamo Oy Procede de production d'une huile vegetale
US5112637A (en) * 1990-11-05 1992-05-12 The United States Of America As Represented By The Secretary Of Agriculture Extraction of gossypol from cottonseed

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0113165A1 (fr) * 1982-09-28 1984-07-11 Imperial Biotechnology Limited Extraction d'huiles et de protéines végétales à partir de graines
WO1991013956A1 (fr) * 1990-03-06 1991-09-19 Öljynpuristamo Oy Procede de production d'une huile vegetale
US5112637A (en) * 1990-11-05 1992-05-12 The United States Of America As Represented By The Secretary Of Agriculture Extraction of gossypol from cottonseed

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTACTS OF JAPAN, Vol. 8, No. 199, C-242; & JP,A,59 091 155, (SANEI KAGAKU KOGYO K.K.), 25 May 1984. *
PATENT ABSTRACTS OF JAPAN, Vol. 8, No. 19, C-207; & JP,A,58 185 654, (SANEI KAGAKU KOGYO K.K.), 29 October 1983. *
PATENT ABSTRACTS OF JAPAN, Vol. 8, No. 3, C-203; & JP,A,58 173 163, (SANEI KAGAKU KOGYO K.K.), 12 October 1983. *

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0839037A4 (fr) * 1995-07-14 1999-03-03 Sabinsa Corp Composition bioprotectrice, son procede d'utilisation et procede d'extraction de curcuminoides
US6156360A (en) * 1997-09-27 2000-12-05 General Mills, Inc. Stabilized annatto-caramel food colorant
US6391372B1 (en) 1997-09-27 2002-05-21 General Mills, Inc. Stabilized annatto-caramel food colorant for RTE cereal
US6444249B1 (en) 1997-09-27 2002-09-03 General Mills, Inc. Stabilized annatto-caramel food colorant
WO2002098530A3 (fr) * 2001-06-06 2003-04-24 Naturel Corp Llc Procede a basse temperature d'extraction de composes principaux provenant de vegetaux ou de matieres vegetales et d'extraits vegetaux ainsi produits
WO2005103212A1 (fr) * 2004-04-23 2005-11-03 Nicolaas Daniel Lombard Burger Procede et appareil utilises dans l'extraction de l'huile vegetale
WO2009060482A1 (fr) * 2007-11-06 2009-05-14 Pectine Industria S.P.A. Procédé d'extraction de caroténoïdes de matières végétales
CN103073915A (zh) * 2013-02-07 2013-05-01 湖南威嘉生物科技有限公司 一种生物酶处理提取分离辣椒红色素和辣椒碱的工艺
CN103073915B (zh) * 2013-02-07 2014-08-20 湖南威嘉生物科技有限公司 一种生物酶处理提取分离辣椒红色素和辣椒碱的工艺
CN113583471A (zh) * 2021-09-17 2021-11-02 云南博瑞生物科技有限公司 工业化生产高品质辣椒红色素的方法
CN113583471B (zh) * 2021-09-17 2023-04-07 云南博瑞生物科技有限公司 工业化生产高品质辣椒红色素的方法

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