WO2006134152A1 - Utilisation d'huile de germes de soya, procede de preparation de cette huile et huile de germes de soya a purete elevee - Google Patents

Utilisation d'huile de germes de soya, procede de preparation de cette huile et huile de germes de soya a purete elevee Download PDF

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Publication number
WO2006134152A1
WO2006134152A1 PCT/EP2006/063252 EP2006063252W WO2006134152A1 WO 2006134152 A1 WO2006134152 A1 WO 2006134152A1 EP 2006063252 W EP2006063252 W EP 2006063252W WO 2006134152 A1 WO2006134152 A1 WO 2006134152A1
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WIPO (PCT)
Prior art keywords
oil
soybean germ
germ oil
phase
soybean
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Ceased
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PCT/EP2006/063252
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English (en)
Inventor
Giancarlo Cravotto
Milvio Avogadro
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BF PHARMA SpA
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BF PHARMA SpA
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Anticipated expiration legal-status Critical
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Classifications

    • 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
    • C11B1/104—Production of fats or fatty oils from raw materials by extracting using super critical gases or vapours
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
    • A23B20/00—Preservation of edible oils or fats
    • A23B20/30—Preservation of other edible oils or fats, e.g. shortenings or cooking oils
    • 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
    • C11B1/02—Pretreatment
    • C11B1/04—Pretreatment of vegetable raw material
    • 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
    • C11B1/06—Production of fats or fatty oils from raw materials by pressing
    • 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
    • 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
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants
    • C11B5/0085—Substances of natural origin of unknown constitution, f.i. plant extracts
    • 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
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants
    • C11B5/0092—Mixtures

Definitions

  • the present invention relates to the use of soybean germ oil as a preservative and against oxidation by degradation, preferably of unsaturated molecules or of products containing such molecules, and to procedures for its production and to a high-purity soybean germ oil.
  • OC-tocopherol as such, commonly known as vitamin E, as an antioxidant additive both in cosmetic and pharmaceutical preparations and in food products rich in fats and oils .
  • Vitamin E though is a not very heat-stable molecule which therefore does not allow for prolonged preservation of products rich in unsaturated molecules, particularly if exposed to high temperatures.
  • epidemiological evidence published by the American Heart Association (2004) indicating an increase in mortality associated with Vitamin E intake in large doses (above 400 U.I. a day) . Therefore, in the food, pharmaceutical and cosmetic fields the need is felt for a preservative, particularly with an antioxidant activity, that is able to protect from degradation molecules containing unsaturations even at high temperatures, that is natural, devoid of side effects and therefore usable even in high concentrations .
  • soybean germ oil according to claims 1, 2 and 3 a combination of soybean germ oil and fish oil according to claim 16 and its use according to claim 19, a process for the preparation of soybean germ oil according to claim 20 and a soybean germ oil according to claims 31, 32 and 33.
  • Soybean germ i.e. the hypocotyle of the seed of soy (Glycine max L.), of which it represents only 2-3% wt., is rich in natural substances with a high nutritional and therapeutic value.
  • the substances mainly contained in the soybean germ are isoflavones, such as for instance genisteine, gliciteine and daidzeine, both omega-3 and omega-6 polyunsaturated fatty acids, such as linoleic acid in an amount of 55 ⁇ 57%, linolenic acid in an amount of 14- 16% and oleic acid in an amount of 10-12%) . This content is much higher compared to the rest of the plant. Furthermore the soybean germ contains lipids present in an amount of approximately 12% wt .
  • vitamins such as niacin (25-30 mg/kg) , pantotenic acid (11-15 mg/kg) , riboflavin (5mg/kg) and further thiamin, pyridoxin, folates, vitamin B12 and vitamin K.
  • soybean germ unsaponifiable lipidic fraction is a concentrate of bioactive molecules comprising for example saponines and particularly phytosterols (approximately 43-46 g/kg) .
  • soybean germ also contains high concentrations of tocopherols as shown in Table 1.
  • the high content in unsaponifiable fraction supplies an important amount of liposoluble vitamins, and at the same time it protects polyunsaturated fatty acids from their easy oxidation by air and light.
  • the present invention provides the use of soybean germ oil as a preservative.
  • soybean germ oil against chemical and biological oxidation and against the degradation of unsaturated molecules .
  • soybean germ oil has a purity higher than 80%, more preferably higher than 95%. Further, preferably soybean germ oil is obtained from soybean germ powder with a content in germ higher than 80%, more preferable from soybean germ powder with a content in germ of 95%.
  • unsaturated molecules are selected from the group comprising polyunsaturated acids, esters of polyunsaturated acids, polyunsaturated alcohols, terpenoids, defines and their derivatives such as salts, amids, aldehydes and ethers.
  • polyunsaturated acids belong to the omega-3 or omega-6 series or, alternatively, they are selected from the group comprising eicosapentaenoc acid, docosahesaenoic acid, linoleic acid, linolenic acid, gamma-linolenic acid, arachidonic acid, eleostearic acid and their derivatives, such as for example isomers like cis-linolenic acid or cis-linoleic acid) .
  • esters of polyunsaturated acids are selected from the group comprising esters of sterols, stands, lecithins, polyalcohols, more preferably glycerol .
  • terpenoids are carotenoids, more preferably selected from the group comprising Vitamin A, lycopene, Beta-Carotene.
  • soybean germ oil can be advantageously used against the degradation of products containing unsaturated molecules .
  • these products are selected from the group comprising fish oil, rapeseed oil, seed oils, flax oil, hemp oil, chia oil, kiwi oil, musqueta rose oil, pumpkin oil, walnut oil, oil extracted from seaweeds, oil extracted from mushrooms, oil extracted from monomolecular biomasses and their mixtures, butter, margarine and food creams.
  • soybean germ oil to unsaturated molecules or to products containing these molecules remarkably increases their resistance to oxidation with respect to antioxidants normally employed in industry.
  • this increased resistance to oxidation is due to a synergic action of components present in the soybean germ oil itself.
  • the present invention provides the use of a combination of soybean germ oil and fish oil, preferably comprising soybean germ oil at a concentration up to 30%, more preferably from 10 to 20%. According to the present invention there is also provided the use of a combination of soybean germ oil and fish oil for the preparation of a medicament for the treatment of dyslipidemias . Further, the present invention provides a new process for the preparation of soybean germ oil.
  • soy seeds after a first cleaning step, are hulled superficially.
  • the decortication phase is performed by friction hulling, wherein friction determines the mechanical detachment of the cuticle and the germ.
  • the decortication phase is performed by steam humidification hulling which is follwed by a toasting phase. The swelling caused by water allows the cuticle and germ to be removed, thus leaving the seed intact.
  • a phase of separating the cuticle from the soybean germ follows, which is perfoermed by sifting, for example a pneumatic sifting, followed by aspiration.
  • the soybean oil production is carried out through extraction with an organic solvent.
  • the organic solvent is selected from the grouo comprising hexane, pentane, petrolether and cyclohexane, .
  • the phase of evaporating the organic solvent from said soybean germ oil can be carried out.
  • the soybean germ oil production is carried out through a phase of pressing the soy germs followed by a filtration phase. This process advantageously allows one to avoid the solvent evaporation phase.
  • the soybean germ oil production is carried out by means of an extraction phase with supercritical fluids extraction, preferably with carbon dioxide.
  • the supercritical fluid is an excellent solvent for unsaturated molecules .
  • the oil obtained according to the processes described above can be used in different forms, e.g. raw, semirefined, refined both by chemical methods through reaction with alkaline substances and by physical distillation.
  • a soybean germ oil is yielded with a degree of purity exceeding 80%, more preferably exceeding 95%.
  • soy seeds after the harvest, and possibly drying, are subjected to a first sifting phase e.g. through vibrating screens.
  • soy seeds are separated from portions of the plant having a larger diameter such as for instance leaves, portions of the pod, wood and from those having a smaller diameter such as broken seeds, powder, small stones.
  • the so obtained seeds are subjected to a hulling phase through cuticle friction.
  • the friction induces the detachment of the cuticle from the germ, the formation of dust and yields a seed without cuticle.
  • an aspiration phase is carried out that separates the light parts, i.e. the cuticle, the germ and the dust, from the seed.
  • the Products obtained during the aspiration phase are submitted to a second sifting, carried out for example by means of a three-way vibrating screen.
  • a gravimetric separation follows which is carried out by means of vibrating gravimetric tables with turbulent air flow.
  • This phase that takes advantage of the different weight of the soybean germ with respect to the remaining cuticle fragments is carried out by means of a fluid bed system that enables soybean germ selection based on density.
  • a soybean germ is produced with a degree of purity exceeding 95%.
  • soybean germ can be used as such or it can be processed to yield soybean germ oil.
  • soybean germ oil production is carried out by means of an extraction phase with hexane at 6O 0 C.
  • the solvent evaporation phase at its boiling point and drying of the oil in a nitrogen stream follow.
  • the final yield in soybean germ oil is about 10-12% by weight with respect to the germ.
  • Table 2 shows the results obtained after heating at 100 0 C.
  • Example 3 Preservation tests, through Rancimat, were carried out on fish oil added with 5000 ppm of Vitamin E and different amounts of soybean germ oil respectively.
  • Table 3 shows the results obtained after heating at HO 0 C.
  • Table 4 shows the results obtained after heating at 9O 0 C TABLE 4
  • soybean germ oil with 95% purity shows a resistance to oxidation nearly twice as large as a Soybean oil enriched at 37 % with soybean germ available on the market .
  • the four groups were respectively treated with: soybean germ oil according to the present invention (OGS) , fish oil (OP) , fish oil added with soybean germ oil according to the present invention at 15% (OP + OGS) and a placebo composition. Measured values are shown in table 5. TABLE 5
  • data reported in table 5 show a reduction in cholesterol and triglyceride levels in the blood of rats treated with fish oil added with soybean germ oil according to the present invention at 15% with respect to groups treated with fish oil and soybean germ oil only.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Zoology (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Botany (AREA)
  • Medicines Containing Plant Substances (AREA)

Abstract

La présente invention concerne l'utilisation d'une huile de germes de soya comme agent de conservation et contre l'oxydation par dégradation, de préférence, de molécules insaturées ou de produits contenant ces molécules, ainsi que des procédés de production de cette huile et une huile de germes de soya à pureté élevée.
PCT/EP2006/063252 2005-06-16 2006-06-15 Utilisation d'huile de germes de soya, procede de preparation de cette huile et huile de germes de soya a purete elevee Ceased WO2006134152A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT000424A ITTO20050424A1 (it) 2005-06-16 2005-06-16 Uso di olio di germe di soia, procedimento per la sua preparazione e olio di germe di soia ad elevata purezza
ITTO2005A000424 2005-06-16

Publications (1)

Publication Number Publication Date
WO2006134152A1 true WO2006134152A1 (fr) 2006-12-21

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PCT/EP2006/063252 Ceased WO2006134152A1 (fr) 2005-06-16 2006-06-15 Utilisation d'huile de germes de soya, procede de preparation de cette huile et huile de germes de soya a purete elevee

Country Status (2)

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IT (1) ITTO20050424A1 (fr)
WO (1) WO2006134152A1 (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2326773A1 (es) * 2008-03-11 2009-10-19 Vicente Bernabeu Poveda Metodo para procesar semillas.
CN101816949B (zh) * 2008-10-14 2011-09-14 中国林业科学研究院林产化学工业研究所 一种氧化降解复合催化剂及在类胡萝卜素制备香料中的应用
CN101380579B (zh) * 2008-10-14 2011-10-05 中国林业科学研究院林产化学工业研究所 氧化降解复合催化剂及其在类胡萝卜素制备香料中的应用
US9119405B2 (en) 2010-12-22 2015-09-01 Conopco, Inc. Water-in-oil emulsion comprising omega-3 fatty acids and process for the manufacture of same
CN106566653A (zh) * 2016-11-03 2017-04-19 山东龙大粮油有限公司 一种减少油脂中挥发性香味成分损失的油脂脱水干燥方法
US9661864B2 (en) 2005-02-17 2017-05-30 Unilever Bcs Us, Inc. Process for the preparation of a spreadable dispersion
US9924730B2 (en) 2010-06-22 2018-03-27 Unilever Bcs Us, Inc. Edible fat powders
US10219523B2 (en) 2010-12-17 2019-03-05 Upfield Us Inc. Process of compacting a microporous fat powder and compacted fat powder so obtained
US11278038B2 (en) 2003-07-17 2022-03-22 Upfield Europe B.V. Process for the preparation of an edible dispersion comprising oil and structuring agent

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US20040241288A1 (en) * 2001-06-28 2004-12-02 Jacob Lahav Composition for coating fruits vegetables and fowl eggs especially useful for organic produce

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US5952230A (en) * 1997-12-16 1999-09-14 Shin Dong Bang Corporation Mechanical method for separating soybean embryos in high purity
JPH11243894A (ja) * 1998-03-02 1999-09-14 Suzuyo Kogyo Kk 浸漬大豆の脱皮装置
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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11278038B2 (en) 2003-07-17 2022-03-22 Upfield Europe B.V. Process for the preparation of an edible dispersion comprising oil and structuring agent
US9661864B2 (en) 2005-02-17 2017-05-30 Unilever Bcs Us, Inc. Process for the preparation of a spreadable dispersion
ES2326773A1 (es) * 2008-03-11 2009-10-19 Vicente Bernabeu Poveda Metodo para procesar semillas.
ES2326773B2 (es) * 2008-03-11 2010-10-27 Vicente Bernabeu Poveda Metodo para procesar semillas.
CN101816949B (zh) * 2008-10-14 2011-09-14 中国林业科学研究院林产化学工业研究所 一种氧化降解复合催化剂及在类胡萝卜素制备香料中的应用
CN101380579B (zh) * 2008-10-14 2011-10-05 中国林业科学研究院林产化学工业研究所 氧化降解复合催化剂及其在类胡萝卜素制备香料中的应用
US9924730B2 (en) 2010-06-22 2018-03-27 Unilever Bcs Us, Inc. Edible fat powders
US10219523B2 (en) 2010-12-17 2019-03-05 Upfield Us Inc. Process of compacting a microporous fat powder and compacted fat powder so obtained
US11071307B2 (en) 2010-12-17 2021-07-27 Upfield Europe B.V. Process of compacting a microporous fat powder and compacted powder so obtained
US9119405B2 (en) 2010-12-22 2015-09-01 Conopco, Inc. Water-in-oil emulsion comprising omega-3 fatty acids and process for the manufacture of same
CN106566653A (zh) * 2016-11-03 2017-04-19 山东龙大粮油有限公司 一种减少油脂中挥发性香味成分损失的油脂脱水干燥方法

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