DE102004030791A1 - Fraktionierung von Allylisothiocyanat und P-Hydroxybenzylisothiocyanat aus Senf - Google Patents

Fraktionierung von Allylisothiocyanat und P-Hydroxybenzylisothiocyanat aus Senf Download PDF

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Publication number
DE102004030791A1
DE102004030791A1 DE102004030791A DE102004030791A DE102004030791A1 DE 102004030791 A1 DE102004030791 A1 DE 102004030791A1 DE 102004030791 A DE102004030791 A DE 102004030791A DE 102004030791 A DE102004030791 A DE 102004030791A DE 102004030791 A1 DE102004030791 A1 DE 102004030791A1
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Germany
Prior art keywords
mustard
seed
allyl isothiocyanate
hydroxybenzylisothiocyanate
fractionation
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DE102004030791A
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DE102004030791B4 (de
Inventor
Shiro Sakai
Makoto Sakai
Hisao Tanaka
Toshio Kon
Kenji Tsukazaki
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Publication of DE102004030791B4 publication Critical patent/DE102004030791B4/de
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
    • C07C331/16—Isothiocyanates
    • C07C331/18—Isothiocyanates having isothiocyanate groups bound to acyclic carbon atoms
    • C07C331/22—Isothiocyanates having isothiocyanate groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
    • C07C331/16—Isothiocyanates
    • C07C331/18—Isothiocyanates having isothiocyanate groups bound to acyclic carbon atoms
    • C07C331/22—Isothiocyanates having isothiocyanate groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
    • C07C331/24—Isothiocyanates having isothiocyanate groups bound to acyclic carbon atoms of an unsaturated carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • 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
    • C11B9/00—Essential oils; Perfumes
    • C11B9/02—Recovery or refining of essential oils from raw materials
    • 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
    • C12P11/00—Preparation of sulfur-containing organic compounds
    • 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
    • C12P13/00—Preparation of nitrogen-containing organic compounds
    • 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
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
    • C12P7/22—Preparation of oxygen-containing organic compounds containing a hydroxy group aromatic

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • Microbiology (AREA)
  • Genetics & Genomics (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Seasonings (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Fats And Perfumes (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Edible Oils And Fats (AREA)

Abstract

Zur Herstellung von Allylisothiocyanat und p-Hydroxybenzylisothiocyanat kann weißer oder schwarzer Senfsamen fraktioniert werden. Es sind Verfahren zur Herstellung dieser Fraktionen aus Senfsamen-Ausgangsstoff offenbart. Der Saat-Ausgangsstoff wird mit Wasser vermischt, um eine aktivierte Suspension zu ergeben, in welcher im Saat-Ausgangsstoff vorhandene Glykosinolate durch das Enzym Myrosinase zu Isothiocyanaten hydrolysiert und abgebaut werden. Danach kann die übrig gebliebene Suspension sterilisiert und weiter auf herkömmliche Weise verarbeitet werden, um verbesserte fertige Senfprodukte zu ergeben.
DE102004030791A 2003-08-07 2004-06-25 Verfahren zur Fraktionierung von Senfsamen, Senfsuspension und Verfahren zur Herstellung von Allylisothiocyanat Expired - Fee Related DE102004030791B4 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CA002436711A CA2436711A1 (en) 2003-08-07 2003-08-07 Fractionation of allyl isothiocyanate, p-hydroxybenzyl-isothiocyanate, protein and fiber from mustard
CA2436711 2003-08-07

Publications (2)

Publication Number Publication Date
DE102004030791A1 true DE102004030791A1 (de) 2005-03-10
DE102004030791B4 DE102004030791B4 (de) 2007-08-23

Family

ID=32873402

Family Applications (1)

Application Number Title Priority Date Filing Date
DE102004030791A Expired - Fee Related DE102004030791B4 (de) 2003-08-07 2004-06-25 Verfahren zur Fraktionierung von Senfsamen, Senfsuspension und Verfahren zur Herstellung von Allylisothiocyanat

Country Status (7)

Country Link
US (1) US20050031768A1 (de)
JP (1) JP2005052139A (de)
CN (1) CN1579222A (de)
CA (1) CA2436711A1 (de)
DE (1) DE102004030791B4 (de)
FR (1) FR2860003B1 (de)
GB (1) GB2404659A (de)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7658961B2 (en) * 2003-10-01 2010-02-09 The Procter & Gamble Company Isothiocyanate preservatives and methods of their use
US8475862B2 (en) 2003-10-01 2013-07-02 The Procter & Gamble Company Isothiocyanate preservatives and methods of their use
US7744937B2 (en) * 2005-08-09 2010-06-29 Kraft Foods Global Brands Llc Chemoprotectants from crucifer seeds and sprouts
US20080311276A1 (en) * 2007-06-12 2008-12-18 Kraft Foods Holdings, Inc. Production of Glucosinolates from Agricultural By-Products & Waste
US20080311192A1 (en) * 2007-06-12 2008-12-18 Kraft Foods Holdings, Inc. Enteric-Coated Glucosinolates And Beta-Thioglucosidases
EP2229824A1 (de) 2009-03-12 2010-09-22 Nestec S.A. Kovalente Milchprotein/isothiocyanatkomplexe
CN101768611B (zh) * 2009-12-31 2012-11-14 北京农鹰现代农业技术研究院 以芥菜籽为原料提取辣根素的方法
US8697150B2 (en) * 2010-03-31 2014-04-15 The Procter & Gamble Company Process of extracting isothiocyanates
US20110244078A1 (en) * 2010-03-31 2011-10-06 Athula Ekanayake Mustard Compositions
CN102277227B (zh) * 2010-06-13 2012-12-12 宏芳香料（昆山）有限公司 一种从芥末籽中提取芥末油和芥末精油的方法
US10925934B2 (en) 2011-02-22 2021-02-23 Caudill Seed and Warehouse Co., Inc. Spray dried myrosinase and use to produce isothiocynates
CN102871066A (zh) * 2011-07-11 2013-01-16 浙江科技学院 应用超临界co2萃取技术制备食品级天然异硫氰酸酯
CN104356178B (zh) * 2014-12-02 2017-04-19 丽江百岁坊生物科技开发有限公司 一种芥子油苷及其代谢产物异硫氰酸苄酯的制备方法
PT3253227T (pt) * 2015-12-02 2020-10-19 Nuseed Global Innovation Ltd Método para remoção de glicosinolatos de farinhas de sementes oleaginosas
US11554104B2 (en) 2017-08-18 2023-01-17 The Schepens Eye Research Institute, Inc. Compositions for the treatment of dry eye and methods of use thereof
CN108130192B (zh) * 2018-02-28 2021-07-06 浙江舟山彩麟之食品有限公司 一种从芥末籽中提取高纯度芥末精油的方法
CN111850062A (zh) * 2020-07-06 2020-10-30 暨南大学 一种超高静压结合转化液辅助水解芥子中硫代葡萄糖苷为异硫氰酸酯的方法
CN113831958A (zh) * 2021-11-03 2021-12-24 仲景食品股份有限公司 一种同步提取芥末精油和芥末油的方法和芥末籽提取物

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB367865A (en) * 1929-08-26 1932-02-25 Ladislaus Berczeller A process for preventing the oxidation of soya beans and bran obtained therefrom
DE702521C (de) * 1935-08-16 1941-02-10 August Zobus Verfahren und Anlage zur Herstellung von Speisesenf
DE1166601B (de) * 1958-06-10 1964-03-26 Oil Seed Products Inc Verfahren zur Herstellung eines Futtermittels durch Entgiften der Extraktionsrueckstaende von Senf- oder Rapssaat
GB883836A (en) * 1958-06-10 1961-12-06 Oil Seed Products Inc Process of obtaining proteinaceous feed material from mustard seed, rape seed and similar seeds
US2987399A (en) * 1959-01-23 1961-06-06 Oil Seed Products Inc Process of obtaining the proteinaceous feed material from mustard seed, rape seed and similar seeds
US3044876A (en) * 1960-04-19 1962-07-17 Oil Seed Products Inc Treatment of mustard seed
US3106469A (en) * 1960-12-02 1963-10-08 Gus C Mustakas Method of obtaining detoxified mustard seed products
US3574640A (en) * 1966-02-21 1971-04-13 Plochman Inc Treatment of mustard seed
GB1286370A (en) * 1970-05-26 1972-08-23 Unilever Ltd Flavouring
US4062979A (en) * 1975-08-01 1977-12-13 Mccormick & Company, Incorporated Spray dried mustard flour
JPS5851754B2 (ja) * 1981-10-08 1983-11-18 四郎 酒井 高タンパク含有マスキング材料
JPS606175A (ja) * 1983-06-24 1985-01-12 T Hasegawa Co Ltd 芥子油抽出物
JP3919489B2 (ja) * 2001-09-10 2007-05-23 金印株式会社 アリルイソチオシアネートを含まないイソチオシアネート類含有食品素材の製造方法

Also Published As

Publication number Publication date
FR2860003B1 (fr) 2009-11-13
GB2404659A (en) 2005-02-09
JP2005052139A (ja) 2005-03-03
CA2436711A1 (en) 2005-02-07
US20050031768A1 (en) 2005-02-10
GB0415696D0 (en) 2004-08-18
FR2860003A1 (fr) 2005-03-25
CN1579222A (zh) 2005-02-16
DE102004030791B4 (de) 2007-08-23

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