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WO2017103838A1 - Complexe de sésamine à 90 % sans solvant et son procédé de synthèse - Google Patents

Complexe de sésamine à 90 % sans solvant et son procédé de synthèse Download PDF

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Publication number
WO2017103838A1
WO2017103838A1 PCT/IB2016/057652 IB2016057652W WO2017103838A1 WO 2017103838 A1 WO2017103838 A1 WO 2017103838A1 IB 2016057652 W IB2016057652 W IB 2016057652W WO 2017103838 A1 WO2017103838 A1 WO 2017103838A1
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WO
WIPO (PCT)
Prior art keywords
sesamin
solvent
crude
complex
extract
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Application number
PCT/IB2016/057652
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English (en)
Inventor
Baidyanath MISHRA
Sujan GANAPATHY
T Shariq Afsar
Original Assignee
MOHAMED ABDULLA ANZAR, Cheppattu
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by MOHAMED ABDULLA ANZAR, Cheppattu filed Critical MOHAMED ABDULLA ANZAR, Cheppattu
Publication of WO2017103838A1 publication Critical patent/WO2017103838A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems
    • 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

Definitions

  • the embodiments herein generally relate to the field of herbal extracts and compositions.
  • the embodiments herein particularly relate to the extraction of bioactive lignans.
  • the embodiments herein more particularly relate to the extraction of solvent free sesamin complex 90% from sesame oil.
  • Sesamum indicum is a flowering plant. Various wild species occur in tropical regions of the world. Sesamum indicum is widely cultivated for edible seeds and oil extraction. The analysis of Sesamum indicum oil indicates that the oil comprises 5.7% moisture, 48.5% crude oil, 20% crude protein, 7.78% carbohydrate, 9.4% crude fiber and 4.2% ash.
  • Sesame oil is an edible vegetable oil derived from sesame seeds. Besides being used as a cooking oil in South India, Sesame oil is often used for enhancing flavors in Chinese, Japanese, Middle-Eastern, Korean and South-East Asian cuisines. Out of the total production of the Sesame oil, about 75% is used for edible purpose, 5% for Vanaspathy industry and about 4% for industrial use as paints, soaps, perfumes etc.
  • Sesame oil is highly resistant to oxidative deterioration as compared to other edible oils. This is attributed to the presence of biologically active compounds namely lignans and lignan glucosides.
  • Lignans are a group of natural products of phenylpropanoid origin.
  • the main lignans in Sesame oil are Sesamin and Sesamolin.
  • lignans are a group of natural products of phenylpropanoid origin.
  • the main lignans in Sesame oil are Sesamin and Sesamolin.
  • Several food, industrial and pharmaceutical uses have been reported for these lignans.
  • Studies have shown that Sesamin is the major compound present in Sesame seeds to inhibit cholesterol absorption and synthesis in rats. Both Sesamin and Sesamolin are reported to increase hepatic mitochondrial and peroxisomal fatty acid oxidation rate.
  • Sesamin is a lignan isolated from Sesamum indicum oil. Sesamin is used as dietary fat-reduction supplement. Sesamin and sesamolin are minor components of sesame oil on average comprising only 0.14% of the sesame oil.
  • the primary objective of the embodiments herein is to provide a method for preparation of solvent free sesamin complex 90% extract from sesame oil.
  • Another objective of the embodiments herein is to provide a solvent free sesamin complex 90% extract which is free from all organic solvents and is safe for consumption.
  • Yet another objective of the embodiments herein is to provide an economical method for preparation of solvent free sesamin complex 90% extract from sesame oil.
  • Yet another objective of the embodiments herein is to provide amethod for preparation of solvent free sesamin complex 90% extract with high yield and purity.
  • Yet another objective of the embodiments herein is to provide solvent free sesamin complex 90% extract for the functional and nutritional support to the individuals struggling with obesity.
  • Yet another objective of the embodiments herein is to provide non-toxic solvent free sesamin complex 90%.
  • the embodiments herein provide a method for synthesizing solvent free sesamin complex 90% extract from sesame oil.
  • the embodiments herein also provide a solvent free sesamin complex 90% extract which is free from all organic solvents and is safe for consumption.
  • the method of synthesizing solvent free sesamin complex comprises the following steps.
  • a crude sesame oil is extracted from sesame seeds by a cold pressing method.
  • the sesame oil is purified from the crude sesame oil with polar solvents.
  • the extraction process is repeated for a plurality of times with polar solvents to get a complete recovery of a crude sesamin complex.
  • the polar solvent fractions or extractives comprising the crude sesamin complex are collected.
  • the polar solvent fractions or extractives are analyzed with HPLC.
  • the crude sesamin complex is concentrated in the polar solvent fractions or extractives at a temperature range of 50-75 °C.
  • the polar solvent present with the crude sesamin complex is distilled at a temperature range.
  • the temperature range is 50-75 °C under a vacuum condition.
  • the pressure is maintained at 600-700 mm/Hg vacuum.
  • a thick paste comprising a crude sesamin extract is obtained.
  • the thick paste comprising the crude sesamin extract is washed with a solvent.
  • a preset volume of thick paste comprising the crude sesamin extract is analyzed.
  • 1 volume of solvent is added to 1 volume of the thick paste comprising the crude sesamin.
  • the solvent is selected from a group consisting of hexane and petroleum ether.
  • a mixture of thick paste comprising crude sesamin extract and solvent is stirred.
  • the mixture of thick paste comprising the crude sesamin extract and solvent is filtered.
  • the mixture of thick paste comprising crude sesamin extract and solvent is filtered by a Nutsche filter.
  • a crude sesamin extract is obtained and drying the sesamin crude extract in a vacuum tray drier (VTD).
  • the sesamin crude extract is added with a 2.5 volume of a solvent in a reactor.
  • the solvent is added based on a quantity of sesamin crude extract.
  • the mixture of the sesamin crude extract and the solvent is stirred in the reactor for 15 minutes.
  • the sesamin crude extract is dissolved in the solvent.
  • the sesamin crude extract dissolute is extracted with the solvent.
  • the sesamin crude extract along with the solvent is loaded into a reactor comprising 2.5 volume of the solvent for washing.
  • a mixture comprising the sesamin crude extract and the solvent is obtained from the reactor.
  • the mixture comprising the sesamin crude extract and the solvent is filtered through a thin film in a high flow bed reactor/thin film fixed bed reactor.
  • the mixture comprising the sesamin crude extract and the solvent is washed with 0.5 volume of the solvent.
  • a clear filtrate of the sesamin crude extract is collected.
  • the clear filtrate of the sesamin crude extract is added with 60 volumes of distilled water in a reactor.
  • the reactor comprising clear filtrate of the sesamin crude extract and distilled water is stirred for one hour at a room temperature to obtain a mixture.
  • the mixture is filtered with a Nutsche filter to obtain a slurry.
  • the slurry comprises a sesamin complex.
  • the sesamin complex is a solvent free complex.
  • the sesamin complex has no solvent.
  • the slurry comprising the sesamin complex is washed and dried at a temperature of 50-65 °C under vacuum for 8 hours.
  • the washed and dried slurry comprising the sesamin complex is pulverized and re-dried at a temperature of 50-65 °C for 8 hours.
  • the dried slurry comprising sesamin complex is analyzed.
  • the method of extracting sesame oil from crude sesame oil comprises the following steps.
  • the crude sesame oil is soaked in polar solvents.
  • the polar solvents are selected from a group consisting of methanol, ethanol and isopropyl alcohol.
  • the crude sesame oil with polar solvent is incubated for a time period of 3 hours at a predetermined temperature.
  • the predetermined temperature is within a range of 50-70°C.
  • the polar solvent is removed by a process selected from a group consisting of filtering and siphoning.
  • the purified sesame oil is obtained.
  • the extraction process of sesame oil is repeated for a plurality of times by adding the polar solvents to crude sesame oil.
  • the slurry comprising Sesamin complex comprises sesamin and sesamolin.
  • the concentration of sesamin in the slurry is within a range of 70-75 weight %.
  • the concentration of sesamolin in the slurry is within a range of 15-20 weight%.
  • the dried slurry is analyzed by gas chromatography.
  • the gas chromatography illustrates/indicates an absence of solvent in the slurry comprising sesamin complex.
  • the sesamin complex is present at a concentration of 90 weight% in the slurry.
  • the sesamin complex is present in the slurry without any solvent.
  • the polar solvent is selected from a group consisting of methanol, ethanol, butanol and isopropyl alcohol.
  • the solvent is selected from a group consisting of cyclohexane and petroleum ether.
  • a solvent free sesamin complex is provided/disclosed.
  • the composition comprises sesamin and sesamolin.
  • the concentration of sesamin is in a range of 70-75 weight %.
  • the concentration of sesamolin is in a range of 15-20 weight%.
  • a sesamin complex composition is provided/disclosed.
  • the sesamin complex is present at a concentration of 90 weight% without any solvent.
  • the sesamin complex reduces cholesterol in the body.
  • the sesamin complex increases an antioxidant in plasma (blood).
  • the antioxidant is vitamin E.
  • the sesamin complex reduces cholesterol in the body.
  • a process for the preparation of solvent free sesamin complex 90% extract form sesame oil.
  • the sesamin complex 90% is completely free form all organic solvents and is safe for consumption. Obesity is due to deposition of high level of cholesterol in the body.
  • the sesamin complex hasan ability to reduce the cholesterol in the body and enhances vitamin E level in plasma which acts as antioxidant. Thus sesamin complex is a valuable functional and nutritional product.
  • the sesamin complex reduces the cholesterol level in the body thereby reducing the body weight and enhancing all the physical activities and good health.
  • methanol, ethanol, isopropyl alcohol, hexane, petroleum ether, cyclo-hexane are procured from Rankem.
  • the method for preparation of solvent free sesamin complex 90% comprises the following steps.
  • the crude sesame oil is extracted with polar solvents like methanol, ethanol, and isopropyl alcohol. Sesame oil is also extracted under low-temperature conditions using an expeller press in a process called cold pressing. Crude sesame oil is soaked in solvent like methanol or ethanol or isopropyl alcohol for three hours at a temperature of 50-70°C. The solvents are filtered or siphoned off. The solvents like methanol or ethanol or isopropyl alcohol are again added to the sesame oil. The extraction process is repeated for several times to completely recover a sesamin complex.
  • the crude sesame oil is analyzed with HPLC to get a complete recovery of sesamin complex. All the sesamin crude extracts are concentrated at temperature range of 50 to 75 °C. After the extraction is completed, all the sesamin crude extracts are pooled in a reactor and the solvent is distilled at a temperature of 50-70°C under a vacuum condition (600 mm/hg).
  • the thick paste obtained in the extraction phase is washed with 1 volume of hexane or petroleum ether. The weight of the thick paste is checked. Same volume of hexane or petroleum ether is measured and added to the thick paste. The mixture of thick paste and the petroleum ether or hexane is stirred well and filtered through Nutche filter.
  • the sesamin crude extract is filtered and dried in a Vacuum Tray Drier (VTD).
  • 2.5 volume of cyclohexane is added to the reactor, based on the quantity of sesamin crude extract.
  • Sesamin crude extract is added to the reactor with constant stirring. The reactor is stirred for 15 minutes for a complete dissolution of sesamin crude extract.
  • Sesamin crude extract is loaded to the reactor comprising 2.5 volume of cyclohexane for washing.
  • the mixture obtained from reactor is filtered through a thin high flow bed. A bed wash is given with 0.5 volume of cyclo hexane.
  • the clear filtrate of sesamin crude extract is collected and 60 volume of distilled water is added to the reactor.
  • the clear filtrate of sesamin crude extract is slowly added to the reactor comprising distilled water.
  • the reactor is subjected to stirring for 1 hour at room temperature. After 1 hour of stirring, the mixture obtained from reactor is filtered with a nutsche filter. The product is washed and dried at 50 to 65 °C under vacuum condition for 8 hrs.
  • the product comprising sesamin is pulverized and re-dried at 50 to 65 °C for 8 hrs.
  • the final product comprises Sesamin with 70-75% and Sesamolin with 15-20%.
  • gas chromatography data revels that the product comprising sesamin and sesamolin is completely devoid of any solvents.
  • FIG.1A-1B jointly illustrate a flow chart explaining a method of synthesizing solvent free sesamin complex 90% extract from sesame oil, according to an embodiment herein.
  • the embodiments herein provide a method for synthesis of solvent free sesamin complex 90% extract from sesame oil.
  • the embodiments herein also provide a solvent free sesamin complex 90% extract which is free from all organic solvents and is safe for consumption.
  • the method of synthesizing solvent free sesamin complex comprises the following steps.
  • a crude sesame oil is extracted from sesame seeds by a cold pressing method.
  • the sesame oil is purified from the crude sesame oil with polar solvents.
  • the extraction process is repeated for a plurality of times with polar solvents to get a complete recovery of a crude sesamin complex.
  • the polar solvent fractions or extractives comprising the crude sesamin complex are collected.
  • the polar solvent fractions or extractives are analyzed with HPLC.
  • the crude sesamin complex is concentrated in the polar solvent fractions or extractives at a temperature range of 50-75 °C.
  • the polar solvent present with the crude sesamin complex is distilled at a temperature range.
  • the temperature range is 50-75 °C under a vacuum condition.
  • the pressure is maintained at 600-700 mm/Hg vacuum.
  • a thick paste comprising a crude sesamin extract is obtained.
  • the thick paste comprising the crude sesamin extract is washed with a solvent.
  • a preset volume of thick paste comprising the crude sesamin extract is analyzed.
  • 1 volume of solvent is added to 1 volume of the thick paste comprising the crude sesamin.
  • the solvent is selected from a group consisting of hexane and petroleum ether.
  • a mixture of thick paste comprising crude sesamin extract and solvent is stirred.
  • the mixture of thick paste comprising the crude sesamin extract and solvent is filtered.
  • the mixture of thick paste comprising crude sesamin extract and solvent is filtered by a Nutsche filter.
  • a crude sesamin extract is obtained and drying the sesamin crude extract in a vacuum tray drier (VTD).
  • the sesamin crude extract is added with a 2.5 volume of a solvent in a reactor.
  • the solvent is added based on a quantity of sesamin crude extract.
  • the mixture of the sesamin crude extract and the solvent is stirred in the reactor for 15 minutes.
  • the sesamin crude extract is dissolved in the solvent.
  • the sesamin crude extract dissolute is extracted with the solvent.
  • the sesamin crude extract along with the solvent is loaded into a reactor comprising 2.5 volume of the solvent for washing.
  • a mixture comprising the sesamin crude extract and the solvent is obtained from the reactor.
  • the mixture comprising the sesamin crude extract and the solvent is filtered through a thin film in a high flow bed reactor/thin film fixed bed reactor.
  • the mixture comprising the sesamin crude extract and the solvent is washed with 0.5 volume of the solvent.
  • a clear filtrate of the sesamin crude extract is collected.
  • the clear filtrate of the sesamin crude extract is added with 60 volumes of distilled water in a reactor.
  • the reactor comprising clear filtrate of the sesamin crude extract and distilled water is stirred for one hour at a room temperature to obtain a mixture.
  • the mixture is filtered with a Nutsche filter to obtain a slurry.
  • the slurry comprises a sesamin complex.
  • the sesamin complex is a solvent free complex.
  • the sesamin complex has no solvent.
  • the slurry comprising the sesamin complex is washed and dried at a temperature of 50-65 °C under vacuum for 8 hours.
  • the washed and dried slurry comprising the sesamin complex is pulverized and re-dried at a temperature of 50-65 °C for 8 hours.
  • the dried slurry comprising sesamin complex is analyzed.
  • the method of extracting sesame oil from crude sesame oil comprises the following steps.
  • the crude sesame oil is soaked in polar solvents.
  • the polar solvents are selected from a group consisting of methanol, ethanol and isopropyl alcohol.
  • the crude sesame oil with polar solvent is incubated for a time period of 3 hours at a predetermined temperature.
  • the predetermined temperature is within a range of 50-70°C.
  • the polar solvent is removed by a process selected from a group consisting of filtering and siphoning.
  • the purified sesame oil is obtained.
  • the extraction process of sesame oil is repeated for a plurality of times by adding the polar solvents to crude sesame oil.
  • the slurry comprising Sesamin complex comprises sesamin and sesamolin.
  • the concentration of sesamin in the slurry is within a range of 70-75 weight %.
  • the concentration of sesamolin in the slurry is within a range of 15-20 weight%.
  • the dried slurry is analyzed by gas chromatography.
  • the gas chromatography illustrates/indicates an absence of solvent in the slurry comprising sesamin complex.
  • the sesamin complex is present at a concentration of 90 weight% in the slurry.
  • the sesamin complex is present in the slurry without any solvent.
  • the polar solvent is selected from a group consisting of methanol, ethanol, butanol and isopropyl alcohol.
  • the solvent is selected from a group consisting of cyclohexane and petroleum ether.
  • a solvent free sesamin complex is provided/disclosed.
  • the composition comprises sesamin and sesamolin.
  • the concentration of sesamin is in a range of 70-75 weight %.
  • the concentration of sesamolin is in a range of 15-20 weight%.
  • a sesamin complex composition is provided/disclosed.
  • the sesamin complex is present at a concentration of 90 weight% without any solvent.
  • the sesamin complex reduces cholesterol in the body.
  • the sesamin complex increases an antioxidant in plasma (blood).
  • the antioxidant is vitamin E.
  • the sesamin complex reduces cholesterol in the body.
  • a process for the preparation of solvent free sesamin complex 90% extract form sesame oil.
  • the sesamin complex 90% is completely free form all organic solvents and is safe for consumption. Obesity is due to deposition of high level of cholesterol in the body.
  • the sesamin complex has an ability to reduce the cholesterol in the body and enhances vitamin E level in plasma which acts as antioxidant. Thus sesamin complex is a valuable functional and nutritional product.
  • the sesamin complex reduces the cholesterol level in the body thereby reducing the body weight and enhancing all the physical activities and good health.
  • methanol, ethanol, isopropyl alcohol, hexane, petroleum ether, cyclo-hexane are procured from Rankem.
  • the method for preparation of solvent free sesamin complex 90% comprises the following steps.
  • the crude sesame oil is extracted with polar solvents like methanol, ethanol, and isopropyl alcohol. Sesame oil is also extracted under low-temperature conditions using an expeller press in a process called cold pressing. Crude sesame oil is soaked in solvent like methanol or ethanol or isopropyl alcohol for three hours at a temperature of 50-70°C. The solvents are filtered or siphoned off. The solvents like methanol or ethanol or isopropyl alcohol are again added to the sesame oil. The extraction process is repeated for several times to completely recover a sesamin complex.
  • the crude sesame oil is analyzed with HPLC to get a complete recovery of sesamin complex. All the sesamin crude extracts are concentrated at temperature range of 50 to 75 °C. After the extraction is completed, all the sesamin crude extracts are pooled in a reactor and the solvent is distilled at a temperature of 50-70°C under a vacuum condition (600 mm/hg).
  • the thick paste obtained in the extraction phase is washed with 1 volume of hexane or petroleum ether. The weight of the thick paste is checked. Same volume of hexane or petroleum ether is measured and added to the thick paste. The mixture of thick paste and the petroleum ether or hexane is stirred well and filtered through Nutche filter.
  • the sesamin crude extract is filtered and dried in a Vacuum Tray Drier (VTD).
  • 2.5 volume of cyclohexane is added to the reactor, based on the quantity of sesamin crude extract.
  • Sesamin crude extract is added to the reactor with a constant stirring. The reactor is stirred for 15 minutes for a complete dissolution of sesamin crude extract.
  • Sesamin crude extract is loaded to the reactor comprising 2.5 volume of cyclohexane for washing.
  • the mixture obtained from reactor is filtered through a thin high flow bed. A bed wash is given with 0.5 volume of cyclo hexane.
  • the clear filtrate of sesamin crude extract is collected and 60 volume of distilled water is added to the reactor.
  • the clear filtrate of sesamin crude extract is slowly added to the reactor comprising distilled water.
  • the reactor is subjected to stirring for 1 hour at room temperature. After 1 hour of stirring, the mixture obtained from reactor is filtered witha nutsche filter. The product is washed and dried at 50 to 65 °C under vacuum condition for 8 hrs.
  • the product comprising sesamin is pulverized and re-dried at 50 to 65 °C for 8 hrs.
  • the final product comprises Sesamin with 70-75% and Sesamolin with 15-20%.
  • gas chromatography data revels that the product comprising sesamin and sesamolin is completely devoid any solvents.
  • FIG.1A-1B jointly illustrate a flow chart explaining a method of synthesizing solvent free sesamin complex 90% extract from sesame oil, according to one embodiment herein.
  • the crude sesame oil is extracted with polar solvents methanol or ethanol or isopropyl alcohol (101).
  • the extraction process is repeated for a plurality of times to get a full recovery of crude sesamin complex (102). All the extracts are concentrated at a temperature range of 50-75°C (103).
  • a thick paste of sesamin crude extract is obtained (104).
  • the obtained thick paste of sesamin crude extract is washed with one volume of hexane or petroleum ether (105).
  • the sesamin crude extract is filtered and dried in a vacuum tray drier (106).
  • the sesamin crude extract is added in a reactor and cyclohexane is added (107).
  • the reactor comprising sesamin crude extract and cyclohexane mixture is stirred for 15 minutes (108).
  • the mixture is filtered through a thin high flow bed after performing a bed washing with 0.5 volume of cyclohexane (109).
  • the clear filtrate of sesamin crude extract is collected (110).
  • 60 volume of distilled water is added to the reactor (111).
  • the clear filtrate of sesamin crude extract is added to the reactor comprising distilled water (112).
  • the mixture of distilled water and sesamin crude extract is stirred in reactor for 1 hour (113).
  • the product comprising sesamin extract is filtered with a nutche filter (114).
  • the sesamin extract is washed with water and dried at 50-60 °C under vacuum atmosphere for 8 hours (115).
  • the product comprising sesamin extract is pulverized and re-dried at 50-65°C for 8

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

La présente invention concerne concerne un procédé de synthèse d'un extrait à 90 % de complexe de sésamine sans solvant. L'huile de sésame brute est extraite de manière répétée à l'aide de solvants polaires. Les extraits sont concentrés pour obtenir une pâte épaisse qui est lavée avec de l'hexane ou de l'éther de pétrole. L'extrait brut de sésamine est filtré et séché en VTD. Du cyclohexane et l'extrait brut de sésamine sont ajoutés au réacteur sous agitation constante. Le mélange est filtré et lavé avec du cyclohexane pour obtenir un filtrat limpide. De l'eau distillée et l'extrait brut de sésamine sont ajoutés au réacteur sous agitation constante. Le mélange obtenu à partir du réacteur est filtré à l'aide d'un filtre Nutsche. Le produit est lavé et séché à 50-65 °C sous vide pendant 8 heures. Le produit comprenant la sésamine est pulvérisé et séché de nouveau. Le produit final comprend 70 à 75 % de sésamine et 15 à 20 % de sésamoline.
PCT/IB2016/057652 2015-12-16 2016-12-15 Complexe de sésamine à 90 % sans solvant et son procédé de synthèse WO2017103838A1 (fr)

Applications Claiming Priority (2)

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IN1295/KOL/2015 2015-12-16
IN1295KO2015 2015-12-16

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111100143A (zh) * 2019-12-26 2020-05-05 山东新和成精化科技有限公司 一种维生素b6中间体的连续化制备方法
CN112255339A (zh) * 2020-10-12 2021-01-22 南京海关动植物与食品检测中心 一种快速测定芝麻油中三种芝麻木脂素含量的方法
CN113717191A (zh) * 2021-09-18 2021-11-30 安徽省凤阳县御膳油脂有限公司 一种利用芝麻粕制备芝麻素的方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8350066B2 (en) * 2007-03-30 2013-01-08 Council of Scientific & Industrial Design Process for the extraction of bioactive lignans with high yield and purity from sesame oil

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Publication number Priority date Publication date Assignee Title
US8350066B2 (en) * 2007-03-30 2013-01-08 Council of Scientific & Industrial Design Process for the extraction of bioactive lignans with high yield and purity from sesame oil

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MIYUKI DATE ET AL.: "Supercritical Carbon Dioxide Extraction of Lignan from Cold-Press By-product of Sesame Seed", POSTER P80-INTERNATIONAL SOCIETY FOR ADVANCEMENT OF SUPERCRITICAL FLUIDS., 2 April 2014 (2014-04-02), XP055391482, Retrieved from the Internet <URL:http://www.isasf.net/fileadmin/files/Docs/DenHaag/HtmlDir/Papers/P80.pdf> *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111100143A (zh) * 2019-12-26 2020-05-05 山东新和成精化科技有限公司 一种维生素b6中间体的连续化制备方法
CN111100143B (zh) * 2019-12-26 2021-09-17 山东新和成精化科技有限公司 一种维生素b6中间体的连续化制备方法
CN112255339A (zh) * 2020-10-12 2021-01-22 南京海关动植物与食品检测中心 一种快速测定芝麻油中三种芝麻木脂素含量的方法
CN113717191A (zh) * 2021-09-18 2021-11-30 安徽省凤阳县御膳油脂有限公司 一种利用芝麻粕制备芝麻素的方法
CN113717191B (zh) * 2021-09-18 2024-06-11 安徽省凤阳县御膳油脂有限公司 一种利用芝麻粕制备芝麻素的方法

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