EP0199354A2 - Huiles essentielles traitées pour en éliminer les notes âpres - Google Patents

Huiles essentielles traitées pour en éliminer les notes âpres Download PDF

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Publication number
EP0199354A2
EP0199354A2 EP86105661A EP86105661A EP0199354A2 EP 0199354 A2 EP0199354 A2 EP 0199354A2 EP 86105661 A EP86105661 A EP 86105661A EP 86105661 A EP86105661 A EP 86105661A EP 0199354 A2 EP0199354 A2 EP 0199354A2
Authority
EP
European Patent Office
Prior art keywords
oil
peroxide
acid
essential oil
notes
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.)
Granted
Application number
EP86105661A
Other languages
German (de)
English (en)
Other versions
EP0199354A3 (en
EP0199354B1 (fr
Inventor
Mamoun M. Hussein
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.)
Nabisco Brands Inc
Original Assignee
Nabisco Brands Inc
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 Nabisco Brands Inc filed Critical Nabisco Brands Inc
Publication of EP0199354A2 publication Critical patent/EP0199354A2/fr
Publication of EP0199354A3 publication Critical patent/EP0199354A3/en
Application granted granted Critical
Publication of EP0199354B1 publication Critical patent/EP0199354B1/fr
Expired legal-status Critical Current

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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
    • C11B9/00—Essential oils; Perfumes
    • C11B9/02—Recovery or refining of essential oils from raw materials
    • C11B9/022—Refining

Definitions

  • the present invention relates to essential oils extracted from botanical matter which are treated with a peroxide-acid reagent to remove harsh flavor notes therefrom.
  • Essential oils which are freshly distilled from botanical matter usually have, when freshly made, what are known as harsh tasting flavor notes. These harsh flavor off-notes are also known as green, burnt, still off-notes. This is particularly true in the case of peppermint oil or spearmint oil which is freshly made by means of steam distillation of the parent botanical matter from which the oil is extracted.
  • the customary procedure employed for removing those harsh flavor notes which are present in the freshly obtained oil is to allow the oil to age or mellow for periods of about 6 to 24 months, in full containers in the presence of oxygen and in the absence of actinic radiation. This aging-mellowing process is economically unattractive since it requires the use of carefully monitored storage facilities, for long periods of time and supervised by technically trained personnel. All of these storage requirements are economically burdensome.
  • the peroxide-acid reagent which is used to treat the essential oils in accordance with the present invention is a combination of one or more water soluble inorganic peroxides such as hydrogen peroxide and/or ozone and one or more water soluble inorganic acids such as hydrochloric acid, sulfuric acid and phosphoric acid.
  • the peroxide is the active agent in the reagent system of the present invention.
  • the acid is merely used to acidify the peroxide.
  • the peroxides and the acids are preferably employed as aqueous solutions having a peroxide or acid concentration of about 30 to 40 weight percent.
  • Aqueous solutions of the peroxides and/or acids having higher or lower concentrations may also be used.
  • the peroxide and acid components of the reagent are added together to the oil to be treated therewith, as disclosed below.
  • the essential oils which are to be treated with the peroxide-acid reagent in accordance with the present invention are the freshly extracted essential oils of botanical matter. These oils are used as flavorants in the food, confectionary, perfume and cosmetic industries. These oils would include those obtained from the following botanical materials: anise, basil, dill weed, chamomile, eucalyptus, fennel, geranium, hop, laurel leaf, lemongrass, bois de rose, caraway, amber, camphor, amyris, galbanum, davana, mentha (spearmint and peppermint).
  • the essential oils which are to be treated with the peroxide-acid reagent in accordance with the present invention may be extracted from their parent botanical matter, i.e., leaves, fruit, bark, root, grass, wood, heartwood, gum, balsam, berries, seed, flowers, twigs and buds, by the commonly employed technique for doing so, i.e., steam distillation.
  • U.S. 4,478,864 discloses the treatment of freshly prepared peppermint oil with maleic anhydride for the purposes of preventing the formation of certain off flavor notes during the aging process. This process removes most of the menthofuran from the fresh peppermint oil, in the form of a menthofuran-maleic anhydride complex. Thus, very little menthofuran is present, during the aging process, to oxidize to produce undesirable flavor notes. This process, however, does not cure all the off-flavor note problems inherent in fresh peppermint oil. An essential oil treated by the process of U.S. 4,478,864 may still have to undergo an aging process to remove off-flavor notes that are present in the freshly prepared oil.
  • the present invention relates to an essential oil of botanical material treated with an acidified peroxide and/or ozone to remove harsh flavor off-notes therefrom.
  • the present invention also relates to a process for removing harsh flavor off-notes from the essential oil of a botanical material which comprises treating said oil with an acidified peroxide and/or ozone.
  • the fresh oil may be rectified (redistilled) prior to or after treatment with the peroxide-acid reagent to improve a particular property characteristic.
  • peppermint oil may be rectified to remove dimethyl sulfide therefrom which provides a green weedy note.
  • the harsh flavor off-notes in the fresh essential oils, which are to be removed by treatment with the peroxide-acid reagent may be characterized, as such, organoleptically. Organoleptically these harsh off-flavor notes may be characterized as: harsh, green, raw, weedy, skunky and burnt.
  • volatile components those components of the oil which are volatile enough as to be capable of being detected by gas chromatography analysis using a Carbowax-20M column operated at a maximum temperature of 230°C and with an injector temperature of a maximum of 250°C.
  • the oil may be extracted in a liquid/liquid extraction with the peroxide-acid reagent, or it may be contacted with the peroxide-acid reagent immobilized on a solid support.
  • each of the peroxide and the acid components of the reagent of the present invention is used in treating the oil therewith, when using the peroxides and acids as 30 to 40% by weight aqueous solutions.
  • the peroxide and acid components are added to the oil, for the purposes of conducting the treatment therewith of the present invention, by adding such components together.
  • the acid is used to form an acidified peroxide.
  • the treatment with the peroxide-acid reagent may be conducted at room temperature, of about 20-25°C, although at higher temperatures a more rapid/efficient extraction may be effected.
  • the liquid/liquid extraction may be done by vigorously shaking a mixture of the oil and the peroxide-acid reagent in commonly employed shaking devices designed to effect efficient liquid/liquid extraction systems.
  • the extraction time required may be about one to ten minutes.
  • aqueous peroxide-acid reagent is used to treat the essential oil in the liquid/liquid extraction process, it is readily moved therefrom by the use of oil/water separating devices such as a separatory funnel, with or without prior centrifuging. Residual traces of the peroxide-acid reagent can be further readily extracted from the oil by treatment with a solution of Na 2 C0 3 (to neutralize the acid) followed by washing with distilled water. The oil is then dried by high speed centrifugation.
  • the treatment of the fresh essential oil with the peroxide-acid reagent can be accomplished before or after any treatment of the oil according to the process of U . S . 4,478,864.
  • the various types of products into which the essential oils of the present invention may be added as flavors or fragrances would include food, confectionary, including chewing gum and pressed mints, perfumes, cosmetic and body hygiene products and medicinals.
  • a 100 ml sample of freshly distilled peppermint oil is shaken, in a 250 ml separatory funnel, with 0.02 grams each of 30% by weight aqueous H 2 0 2 and 12 N HC1 for 1 to 2 minutes.
  • the aqueous (bottom) layer is discarded after complete separation of the layers.
  • the peppermint oil layer is washed by extraction with 2 x 50 ml 5% sodium carbonate solution and 2 x 50 ml distilled water, and the completely separated aqueous layer is then discarded.
  • the oil is dried with 4 g anhydrous sodium sulfate and by centrifugation at 2000 to 3000 rpm.
  • the resulting oil is crystal clear and possesses a clean characteristic mellow aroma of a good quality aged peppermint oil.
  • the harsh objectionable aroma of the starting oil is eliminated.
  • the taste of the treated oil, when evaluated in a sugar fondant at 0.2 weight percent level and in a chewing gum at about a 0.5 to 1.5 weight percent level, is similarly improved from that of the starting oil.
  • a sample of freshly distilled spearmint oil is also treated according to the procedure of Example 1. A similar improvement of the treated oil is noted.
  • the magnitude of improvement in a treated oil depends on the quality of the starting oil; the more objectionable and the harsher the starting oil is, the more dramatic is the improvement obtained by the treatment thereof according to the present invention.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Fats And Perfumes (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Preparation Of Fruits And Vegetables (AREA)
EP86105661A 1985-04-26 1986-04-24 Huiles essentielles traitées pour en éliminer les notes âpres Expired EP0199354B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US72764685A 1985-04-26 1985-04-26
US727646 1985-04-26

Publications (3)

Publication Number Publication Date
EP0199354A2 true EP0199354A2 (fr) 1986-10-29
EP0199354A3 EP0199354A3 (en) 1987-05-06
EP0199354B1 EP0199354B1 (fr) 1989-07-19

Family

ID=24923444

Family Applications (1)

Application Number Title Priority Date Filing Date
EP86105661A Expired EP0199354B1 (fr) 1985-04-26 1986-04-24 Huiles essentielles traitées pour en éliminer les notes âpres

Country Status (9)

Country Link
EP (1) EP0199354B1 (fr)
JP (1) JPS61258899A (fr)
CN (1) CN1006553B (fr)
AU (1) AU583915B2 (fr)
CA (1) CA1285175C (fr)
DE (1) DE3664478D1 (fr)
ES (1) ES8802367A1 (fr)
NZ (1) NZ215941A (fr)
ZA (1) ZA863080B (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113403147A (zh) * 2021-07-21 2021-09-17 广州丽悦香精香料有限公司 一种雪层杜鹃精油及其提取方法和应用
CN114854495A (zh) * 2022-06-16 2022-08-05 银谷芳香科技有限公司 一种分段式蒸馏提取大马士革玫瑰精油的工艺方法

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4613513A (en) * 1985-03-20 1986-09-23 Nabisco Brands, Inc. Essential oils treatment to remove harsh notes therefrom
US8865192B2 (en) * 2006-07-07 2014-10-21 The Procter & Gamble Co Flavor oils with reduced sulfur content and use in oral care compositions
CN107699352A (zh) * 2017-09-27 2018-02-16 湖北中烟工业有限责任公司 一种提高罗马春黄菊油香气品质的方法及其应用
CN107653064A (zh) * 2017-09-27 2018-02-02 湖北中烟工业有限责任公司 一种抗氧化性强、高香气罗马春黄菊发酵净油的制备方法及其应用
CN109601821A (zh) * 2018-12-29 2019-04-12 珠海市自然之旅生物技术有限公司 一种具有抗菌性能精油气味去除方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE334274C (de) * 1917-10-18 1921-03-10 Hugo Bruen Verfahren zur Verbesserung des Geschmackes und Geruches von Gemuese- und Futterpflanzen aus der Familie der Kruziferen sowie aus verwandten Familien
DE334374C (de) * 1918-06-18 1921-03-12 Rudolf Schmidtmann Bombenvisier fuer Luftfahrzeuge
FR1131573A (fr) * 1954-07-16 1957-02-25 Dragoco Gerberding Co Gmbh Procédé de préparation de produits oxygénés à odeur musquée et produits conformes à ceux obtenus
GB1130230A (en) * 1966-09-29 1968-10-09 Farmo Chimica Dott E Corvi Far A method for preparing an essential oil of turpentine
EP0113988A2 (fr) * 1982-12-20 1984-07-25 Warner-Lambert Company Procédé de préparation d'une huile de menthe poivrée à teneur réduite en menthofurane

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE334274C (de) * 1917-10-18 1921-03-10 Hugo Bruen Verfahren zur Verbesserung des Geschmackes und Geruches von Gemuese- und Futterpflanzen aus der Familie der Kruziferen sowie aus verwandten Familien
DE334374C (de) * 1918-06-18 1921-03-12 Rudolf Schmidtmann Bombenvisier fuer Luftfahrzeuge
FR1131573A (fr) * 1954-07-16 1957-02-25 Dragoco Gerberding Co Gmbh Procédé de préparation de produits oxygénés à odeur musquée et produits conformes à ceux obtenus
GB1130230A (en) * 1966-09-29 1968-10-09 Farmo Chimica Dott E Corvi Far A method for preparing an essential oil of turpentine
EP0113988A2 (fr) * 1982-12-20 1984-07-25 Warner-Lambert Company Procédé de préparation d'une huile de menthe poivrée à teneur réduite en menthofurane

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
AGRICULTURAL & BIOLOGICAL CHEMISTRY, vol. 44, no. 7, July 1980, pages 1535-1543, Tokyo, JP; K.TAKAHASHI et al.: "A new keto-alcohol, (-)-mintlactone, (+)-isomintlactone and minor components in peppermint oil" *
BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, no. 9, 1967, pages 3152-3154; YVES-RENE NAVES: "No 561. - Etudes sur les matières végétales volatiles CCIII (1). Présence de n-undécatriènes-1,3,5 dans l'huile essentielle de la gomme-résine de galbanum" *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113403147A (zh) * 2021-07-21 2021-09-17 广州丽悦香精香料有限公司 一种雪层杜鹃精油及其提取方法和应用
CN114854495A (zh) * 2022-06-16 2022-08-05 银谷芳香科技有限公司 一种分段式蒸馏提取大马士革玫瑰精油的工艺方法
CN114854495B (zh) * 2022-06-16 2023-11-03 银谷芳香科技有限公司 一种分段式蒸馏提取大马士革玫瑰精油的工艺方法

Also Published As

Publication number Publication date
DE3664478D1 (en) 1989-08-24
CA1285175C (fr) 1991-06-25
CN1006553B (zh) 1990-01-24
ES8802367A1 (es) 1988-06-01
JPS61258899A (ja) 1986-11-17
ES554260A0 (es) 1988-06-01
EP0199354A3 (en) 1987-05-06
EP0199354B1 (fr) 1989-07-19
CN86102952A (zh) 1987-11-04
NZ215941A (en) 1988-08-30
AU5681186A (en) 1986-10-30
AU583915B2 (en) 1989-05-11
ZA863080B (en) 1986-12-30

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