EP1687261A1 - Neue oxynitrile - Google Patents

Neue oxynitrile

Info

Publication number
EP1687261A1
EP1687261A1 EP04818703A EP04818703A EP1687261A1 EP 1687261 A1 EP1687261 A1 EP 1687261A1 EP 04818703 A EP04818703 A EP 04818703A EP 04818703 A EP04818703 A EP 04818703A EP 1687261 A1 EP1687261 A1 EP 1687261A1
Authority
EP
European Patent Office
Prior art keywords
product
article
preparation
composition
compound
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.)
Withdrawn
Application number
EP04818703A
Other languages
English (en)
French (fr)
Other versions
EP1687261A4 (de
Inventor
Luca Turin
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.)
Flexitral Inc
Original Assignee
Flexitral 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 Flexitral Inc filed Critical Flexitral Inc
Publication of EP1687261A1 publication Critical patent/EP1687261A1/de
Publication of EP1687261A4 publication Critical patent/EP1687261A4/de
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/11—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound oxygen atoms bound to the same saturated acyclic carbon skeleton
    • C07C255/13—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound oxygen atoms bound to the same saturated acyclic carbon skeleton containing cyano groups and etherified hydroxy groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/16—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound oxygen atoms bound to the same carbon atom of an acyclic carbon skeleton
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G4/00—Chewing gum
    • A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/202—Aliphatic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/202—Aliphatic compounds
    • A23L27/2022—Aliphatic compounds containing sulfur
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
    • 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
    • C11B9/0007—Aliphatic compounds
    • C11B9/0023—Aliphatic compounds containing nitrogen as the only heteroatom
    • 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
    • C11B9/0069—Heterocyclic compounds
    • C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
    • C11B9/0076—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing less than six atoms

Definitions

  • the present invention relates generally to the field of fragrances. More particularly, the present invention relates to novel aromachemicals that provide perfumes and other articles with unique properties and advantages not shared by other aromachemicals. These derivatives find utility in any and all applications requiring certain aroma themes. The invention also relates to mixtures of these derivatives, methods for their preparation and their use as perfume materials for application to a variety of substrates.
  • fragrances used as ingredients in perfumes and in a varied range of other products.
  • perfumes for application in laundry detergents, fabric softeners, rinse conditioners and other products intended for use on textile fibers primarily contain fragrances.
  • a large number of compounds belonging to the nitrile chemical family are known in the perfume industry.
  • Nitriles have been known for use in augmenting or enhancing the aroma of perfume compositions, perfumed articles and colognes for a number of years.
  • Geranyl nitrile (3,7-dimethyl-2,6-octadienenitrile) possesses a strong green, chemical odor resembling that of citral (Z-3,7-dimethyl-2,6-octadienal), the latter being itself a compound of widespread use in perfumery applications and of natural occurrence.
  • Citronellyl nitrile (3,7-dimethyl-6-octenenitrile) shows an olfactive note reminiscent of the odor of lemon, with an undernote characteristic of the nitriles. The citrus note is likewise quite pronounced in Ozonil.RTM.
  • TABACENE® a mixture of such compounds is marketed as TABACENE® by Firmenich et cie, S.A. of Geneva, Switzerland (as referred to in the Fragrance Materials Association of The United States, Inc. "Trademark And Coined Names Catalogue” on page TI).
  • Detergents, deodorants or antiperspirants and soaps are examples of products which are aggressive media, in which citral, for example, which can be considered as the typical compound representing the citrus-type odor, with its powerful citrus-green note, is unstable, preventing it from being used in functional perfumery, and this in spite of its odor which is very prized by perfumers.
  • R is straight or branched chain alkyl, alkenyl having 1-16 carbon atoms, aryl, aralkyl, alkaryl, or substituted derivatives thereof.
  • a second embodiment of the invention concerns compositions, products, preparations or articles having improved aroma, fragrance or odor characteristics containing as active ingredient a compound described above or a mixture thereof.
  • compositions, products, preparations or articles having improved flavor or taste characteristics containing as active ingredient a compound described above or a mixture thereof relate to compositions, products, preparations or articles having improved flavor or taste characteristics containing as active ingredient a compound described above or a mixture thereof.
  • a further embodiment of the invention concerns methods to confer, improve, enhance or modify the taste or flavor property of a composition, product, preparation or article which comprises adding thereto a flavor effective amount of a compound described above or a mixture thereof.
  • a still further embodiment of the invention relates to a method to confer, improve, enhance or modify the aroma, fragrance or odor characteristics of compositions, products, preparations or articles which comprises adding thereto an aroma, fragrance or odor effective amount of a compound described above or a mixture thereof.
  • An additional embodiment of the invention concerns articles of manufacture comprising a compound described above or a mixture thereof.
  • the aromachemicals of the invention may be prepared according to the method set forth below which is directed to the synthesis of the above-noted preferred compound.
  • the aromachemicals of the invention possess the odor profile of the corresponding nitriles but with a greatly lessened unpleasant oily-metallic note typical of the nitriles.
  • suitable articles of manufacture in which the derivatives of the invention may be incorporated include perfumes and colognes, candles, air fresheners, detergent compositions and disinfectants.
  • suitable articles of manufacture in which the derivatives of the invention may be incorporated include perfumes and colognes, candles, air fresheners, detergent compositions and disinfectants.
  • the compositions, products, preparations and articles in which the compounds and derivatives of the invention may be incorporated include candles, air fresheners, perfumes, fragrances, colognes, soaps, bath or shower gels, shampoos or other hair care products, cosmetic preparations, body odorants, deodorants or antiperspirants, liquid or solid fabric detergents or softeners, bleach products (hypochlorites), disinfectants, all-purpose household or industrial cleaners, foods, flavorings, beverages such as beer and soda, denture cleansers (tablets), flavored orally-delivered products such as lozenges, candies, chewing gums, matrices, pharmaceuticals and the like.
  • the compounds can be used as perfuming ingredients, as single compounds or as mixture thereof, preferably at a range of at least about 30% by weight of the perfume composition, more preferably at a range of at least about 60% by weight of the composition.
  • the compounds can even be used in their pure state or as mixtures, without added components.
  • the olfactive characteristics of the individual compounds are also present in mixtures thereof, and mixtures of these compounds can be used as perfuming ingredients. This may be particularly advantageous where separation and/or purification steps can be avoided by using compound mixtures.
  • the derivatives of the invention can be included in virtually any article of manufacture that can include conventional aromachemicals, or for that matter, other fragrances, whether natural or artificial.
  • Examples include bleach, detergents, flavorings and fragrances, beverages, including alcoholic beverages, and the like.
  • the derivatives of the invention can be used in applications like soaps, shampoos, body deodorants and antiperspirants, solid or liquid detergents for treating textiles, fabric softeners, detergent compositions and/or all-purpose cleaners for cleaning dishes or various surfaces, for both household and industrial use.
  • the use of the compounds is not limited to the above-mentioned products, as they be used in other current uses in perfumery, namely the perfuming of soaps and shower gels, hygiene or hair-care products, as well as of body deodorants, air fresheners and cosmetic preparations, and even in fine perfumery, namely in perfumes and colognes.
  • the products of the invention also find utility in foods, flavorings, beverages such as beer and soda, denture cleansers (tablets), flavored orally-delivered products such as lozenges, candies, chewing gums, matrices, pharmaceuticals and the like. These uses are described in more detail below.
  • the derivatives of the invention can be used alone, in admixture with each other, or in admixture with other perfuming ingredients, solvents or adjuvants of current use in the art.
  • the derivatives of the invention are typically present at concentrations between about 0.1 and about 10%, or even more, by weight of these compounds relative to the weight of the perfuming composition in which they are incorporated. Far lower concentrations than those mentioned above can be used when the compounds are directly applied for perfuming the various consumer products cited beforehand.
  • the compounds may be used in detergents containing bleaching agents and activators such as, for example, tetraacetylethylenediamine (TAED), hypohalites, in particular hypochlorite, peroxygenated bleaching agents such as, for example, perborates, etc.
  • TAED tetraacetylethylenediamine
  • hypohalites in particular hypochlorite
  • peroxygenated bleaching agents such as, for example, perborates, etc.
  • the compounds can also be used in body deodorants and antiperspirants, for example, those containing aluminum salts.
  • compositions herein include a detersive surfactant and optionally, one or more additional detergent ingredients, including materials for assisting or enhancing cleaning performance, treatment of the substrate to be cleaned, or to modify the aesthetics of the detergent composition (e.g., perfumes, colorants, dyes, etc.).
  • additional detergent ingredients including materials for assisting or enhancing cleaning performance, treatment of the substrate to be cleaned, or to modify the aesthetics of the detergent composition (e.g., perfumes, colorants, dyes, etc.).
  • Non-limiting examples of synthetic detersive surfactants useful herein typically at levels from about 0.5% to about 90%, by weight, include the conventional Cl-18 alkyl benzene sulfonates ("LAS") and primary, branch-chain and random CIO-20 alkyl sulfates ("AS”), and the like.
  • Preferred compositions incorporating only synthetic detergents have a detergent level of from about 0.5% to 50%.
  • Compositions containing soap preferably comprise from about i
  • compositions herein can contain other ingredients such as enzymes, bleaches, fabric softening agents, dye transfer inhibitors, suds suppressors, and chelating agents, all well known within the art.
  • the derivatives described herein can be incorporated into beverages and impart various flavorings to the beverages.
  • the beverage composition can be a cola beverage composition, and can also be coffee, tea, dairy beverage, fruit juice drink, orange drink, lemon-lime drink, beer, malt beverages, or other flavored beverage.
  • the beverages can be in liquid or powdered form.
  • the beverage compositions can also include one or more flavoring agents; artificial colorants; vitamin additives; preservatives; caffeine additives; water; acidulants; thickeners; buffering agents; emulsifiers; and or fruit juice concentrates.
  • Artificial colorants which may be used include caramel color, yellow 6 and yellow 5.
  • Useful vitamin additives include vitamin B2, vitamin B6, vitamin B12, vitamin C (ascorbic acid), niacin, pantothenic acid, biotin and folic acid.
  • Suitable preservatives include sodium or potassium benzoate. Salts which may be used include sodium, potassium and magnesium chloride.
  • Exemplary emulsifiers are gum arabic and purity gum, and a useful thickener is pectin.
  • Suitable acidulants include citric, phosphoric and malic acid, and potential buffering agents include sodium and potassium citrate.
  • the beverage is a carbonated cola beverage.
  • the pH is generally about 2.8 and the following ingredients can be used to make the syrup for these compositions: Flavor Concentrate, including one or more of the derivatives described herein (22.22 ml), 80% Phosphoric Acid (5.55 g), Citric Acid (0.267 g), Caffeine (1.24 g), artificial sweetener, sugar or com syrup (to taste, depending on the actual sweetener) and Potassium Citrate (4.07 g).
  • the beverage composition can be prepared, for example, by mixing the foregoing syrup with carbonated water in a proportion of 50 ml syrup to 250 ml of carbonated water.
  • Flavored food and pharmaceutical compositions including one or more of the derivatives described herein can also be prepared.
  • the derivatives can be incorporated into conventional foodstuffs using techniques well known to those of skill in the art.
  • the derivatives can be incorporated within polymeric particles, which can, in turn, be dispersed within and/or over a surface of an orally-deliverable matrix material, which is usually a solid or semi-solid substrate.
  • the derivatives When used in chewable compositions, the derivatives can be released into the orally-deliverable polymeric matrix material as the composition is chewed and held in the mouth, thus prolonging the flavor of the composition.
  • the flavor In the case of dried powders and mixes, the flavor can be made available as the product is consumed or be released into the matrix material as the composition is further processed.
  • the relative amounts of the additives can be selected to provide simultaneous release and exhaustion of the compounds.
  • the flavored composition includes an orally-deliverable matrix material; a plurality of water insoluble polymeric particles dispersed in the orally-deliverable matrix material, where the polymeric particles individually define networks of internal pores and are non-degradable in the digestive tract; and one or more derivatives as described herein entrapped within the internal pore networks.
  • the derivatives are released as the matrix is chewed, dissolved in the mouth, or undergoes further processing selected from the group consisting of liquid addition, dry blending, stirring, mixing, heating, baking, and cooking.
  • the orally-deliverable matrix material can be selected from the group consisting of gums, latex materials, crystallized sugars, amorphous sugars, fondants, nougats, jams, jellies, pastes, powders, dry blends, dehydrated food mixes, baked goods, batters, doughs, tablets, and lozenges.
  • a flavorless gum base can be combined with a derivative of the invention or other suitable derivative as described herein to a desired flavor concentration.
  • a blade mixer is heated to about 11 OF, the gum base is preheated so that it is softened, and the gum base is then added to the mixer and allowed to mix for approximately 30 seconds.
  • the flavored derivative is then added to the mixer and mixed for a suitable amount of time.
  • the gum can be then removed from the mixer and rolled to stick thickness on waxed paper while warm.
  • the derivatives described herein are incorporated into a system which can release a fragrance in a controlled manner. These include substrates such as air fresheners, laundry detergents, fabric softeners, deodorants, lotions, and other household items.
  • the fragrances are generally one or more derivatives of essential oils as described herein, each present in different quantities.
  • U.S. Pat. No. 4,587,129 the contents of which are hereby incorporated by reference in their entirety, describes a method for preparing gel articles which contain up to 90% by weight of fragrance or perfume oils.
  • the gels are prepared from a polymer having a hydroxy (lower alkoxy) 2-alkeneoate, a hydroxy (lower alkoxy) lower alkyl 2-alkeneoate, or a hydroxy poly (lower alkoxy)lower alkyl 2-alkeneoate and a polyethylenically unsaturated crosslinking agent.
  • These materials have continuous slow release properties, i.e., they release the fragrance component continuously over a long period of time.
  • all or a portion of those derivatives that include an aldehyde group can be modified to include an acetal group, which can cause the formulations to release fragrance over a period of time as the acetal hydrolyzes to form the aldehyde compound.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Nutrition Science (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Fats And Perfumes (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Seasonings (AREA)
  • Confectionery (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Cosmetics (AREA)
EP04818703A 2003-11-12 2004-11-12 Neue oxynitrile Withdrawn EP1687261A4 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US51865503P 2003-11-12 2003-11-12
PCT/US2004/037771 WO2005047232A1 (en) 2003-11-12 2004-11-12 Novel oxy-nitriles

Publications (2)

Publication Number Publication Date
EP1687261A1 true EP1687261A1 (de) 2006-08-09
EP1687261A4 EP1687261A4 (de) 2007-09-05

Family

ID=34590289

Family Applications (1)

Application Number Title Priority Date Filing Date
EP04818703A Withdrawn EP1687261A4 (de) 2003-11-12 2004-11-12 Neue oxynitrile

Country Status (9)

Country Link
EP (1) EP1687261A4 (de)
JP (1) JP2007510754A (de)
KR (1) KR20060093123A (de)
CN (1) CN1902161A (de)
AU (1) AU2004288828A1 (de)
CA (1) CA2545617A1 (de)
GB (1) GB2423303A (de)
WO (1) WO2005047232A1 (de)
ZA (1) ZA200603778B (de)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5399376B2 (ja) * 2007-04-16 2014-01-29 フイルメニツヒ ソシエテ アノニム 付香成分としての４−ドデセン誘導体
US9186642B2 (en) 2010-04-28 2015-11-17 The Procter & Gamble Company Delivery particle
US9993793B2 (en) 2010-04-28 2018-06-12 The Procter & Gamble Company Delivery particles
MX2013010980A (es) 2011-04-07 2013-10-30 Procter & Gamble Composiciones de limpieza personal con deposito mejorado de microcapsulas de poliacrilato.
JP5869663B2 (ja) 2011-04-07 2016-02-24 ザ プロクター アンド ギャンブルカンパニー ポリアクリレートマイクロカプセルの付着が増大したシャンプー組成物
EP2694031B1 (de) 2011-04-07 2015-07-08 The Procter and Gamble Company Haarspülungszusammensetzungen mit erhöhter abscheidung von polyacrylat-mikrokapseln
US20120322709A1 (en) 2011-05-26 2012-12-20 Jianjun Justin Li Compositions comprising an efficient perfume bloom
WO2015048163A1 (en) 2013-09-25 2015-04-02 Takasago International Corp. (Usa) (6z)-non-6-enenitrile as a fragrance and flavor material

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2601825A1 (de) * 1976-01-20 1977-07-21 Basf Ag Als riechstoffe geeignete aethernitrile

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2169578A (en) * 1938-10-01 1939-08-15 Resinous Prod & Chemical Co Higher alkoxyacetonitriles
US4077916A (en) * 1976-06-08 1978-03-07 Fritzsche Dodge & Olcott Inc. Hexyloxyacetonitrile perfume compositions
JP2978342B2 (ja) * 1992-10-26 1999-11-15 花王株式会社 漂白剤組成物
ZA994918B (en) * 1998-09-04 2000-02-07 Givaudan Roure Int New ketones.

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2601825A1 (de) * 1976-01-20 1977-07-21 Basf Ag Als riechstoffe geeignete aethernitrile

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DATABASE CA [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; KULKA, K. ET AL: "Syntheses and odor properties of aliphatic, aromatic, and cyclic oxyacetonitriles" XP002443681 retrieved from STN Database accession no. 1980:116249 & INT. CONGR. ESSENT. OILS, [PAP.], 7TH , MEETING DATE 1977, VOLUME 7, 259-62 PUBLISHER: JAPAN FLAVOR FRAGRANCE MANUFACTURES' ASSOC., TOKYO, JAPAN. CODEN: 41XWA4, 1979, *
See also references of WO2005047232A1 *

Also Published As

Publication number Publication date
CN1902161A (zh) 2007-01-24
AU2004288828A1 (en) 2005-05-26
CA2545617A1 (en) 2005-05-26
EP1687261A4 (de) 2007-09-05
JP2007510754A (ja) 2007-04-26
KR20060093123A (ko) 2006-08-23
WO2005047232A1 (en) 2005-05-26
GB2423303A (en) 2006-08-23
GB0611515D0 (en) 2006-07-19
ZA200603778B (en) 2009-07-29

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