WO2004103962A2 - Alcoxy alkylsulfanyl phenols - Google Patents

Alcoxy alkylsulfanyl phenols Download PDF

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Publication number
WO2004103962A2
WO2004103962A2 PCT/US2004/015875 US2004015875W WO2004103962A2 WO 2004103962 A2 WO2004103962 A2 WO 2004103962A2 US 2004015875 W US2004015875 W US 2004015875W WO 2004103962 A2 WO2004103962 A2 WO 2004103962A2
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WO
WIPO (PCT)
Prior art keywords
product
article
preparation
composition
compound
Prior art date
Application number
PCT/US2004/015875
Other languages
English (en)
Other versions
WO2004103962A3 (fr
Inventor
Luca Turin
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.
Priority to AU2004241286A priority Critical patent/AU2004241286B2/en
Priority to GB0525822A priority patent/GB2417956B/en
Priority to MXPA05012669A priority patent/MXPA05012669A/es
Priority to EP04752818A priority patent/EP1631147A4/fr
Priority to CA002526243A priority patent/CA2526243A1/fr
Priority to JP2006533255A priority patent/JP2007506802A/ja
Publication of WO2004103962A2 publication Critical patent/WO2004103962A2/fr
Publication of WO2004103962A3 publication Critical patent/WO2004103962A3/fr
Priority to US11/283,053 priority patent/US20060189509A1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/20—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
    • A01N57/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing aromatic radicals
    • 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
    • C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring

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.
  • 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.
  • natural perfume chemicals such as essential oils, oil of rose and oil of cloves, and animal secretions, such as musk
  • Synthetic aroma chemicals have added a new dimension to the art of perfuming, since these synthetics are usually stable compounds and are relatively inexpensive, as compared with the natural perfume chemicals.
  • ethylene glycol monoaryl ethers are known fragrance compounds having a mild rose odor and are useful for food, cosmetic and pharmaceutical applications. See, for example, U.S. Pat. Nos. 1,881,200; 2,451,149 and 4,404,407.
  • synthetics lend themselves more easily to manipulation than natural perfume chemicals since natural perfume chemicals are usually a complex mixture of substances. Accordingly, for these and other reasons, there is a great desire in the art of fragrance chemistry for new compounds possessing specific characteristic aromas, in particular, floral (carnation).
  • Exemplary patents disclosing compounds exhibiting carnation odor notes are US 6,177,400 and 4,464,291.
  • Novel fragrance and flavor aromachemicals are disclosed herein as well as methods of making the derivatives, uses of the aromachemicals and articles of manufacture including the aromachemicals. These novel 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.
  • R is a straight or branched chain, saturated or unsaturated hydrocarbyl group; preferably, alkyl or alkenyl, having 1-8 carbon atoms;
  • Ri is a straight or branched chain, saturated or unsaturated hydrocarbyl group; preferably, alkyl or alkenyl, having 1-8 carbon atoms.
  • 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 relates 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.
  • a particularly preferred aromachemical is 2-methoxy-4-methylsulfanylphenol having the formula:
  • aromachemicals of the invention may be prepared according to the reaction scheme set forth in the examples which outlines the synthesis of 2-methoxy-4- methylsulfanylphenol.
  • the aromachemicals of the invention possess the odor profile: floral, carnation, spicy, and smoky.
  • 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.
  • 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.
  • perfuming ingredients solvents or adjuvants of current use in the art.
  • the nature and the variety of these co-ingredients do not require a more detailed description here, which, moreover, would not be exhaustive, and the person skilled in the art will be able to choose the latter through its general knowledge and as a function of the nature of the product to be perfumed and of the desired olfactive effect.
  • perfuming ingredients typically belong to chemical classes as varied as alcohols, aldehydes, ketones, esters, ethers, acetates, nitrites, terpene hydrocarbons, sulfur- and nitrogen containing heterocyclic compounds, as well as essential oils of natural or synthetic origin.
  • alcohols aldehydes, ketones, esters, ethers, acetates, nitrites, terpene hydrocarbons, sulfur- and nitrogen containing heterocyclic compounds, as well as essential oils of natural or synthetic origin.
  • the proportions in which the derivatives of the invention can be incorporated in the various products vary within a large range of values. These values depend on the nature of the article or product that one desires to perfume and the odor effect searched for, as well as on the nature of the co-ingredients in a given composition when the compounds are used in admixture with perfuming co-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.
  • body deodorants and antiperspirants for example, those containing aluminum salts.
  • the 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.).
  • LAS Cl-18 alkyl benzene sulfonates
  • AS primary, branch-chain and random CIO-20 alkyl sulfates
  • compositions incorporating only synthetic detergents have a detergent level of from about 0.5% to 50%.
  • Compositions containing soap preferably comprise from about 10% to about 90% soap.
  • 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).
  • 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
  • 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 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 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.

Abstract

L'invention concerne des composés alcoxy alkylsulfanyl chimiques aromatiques ou des mélanges de ces derniers, représentés par la formule générale : R1O-C6H5OH-SR. Dans cette formule, R désigne un groupe hydrocarbyle saturé ou insaturé, à chaîne droite ou ramifiée ; de préférence, un alkyle ou un alcényle comportant 1-8 atomes de carbone ; et R1 désigne un groupe hydrocarbyle saturé ou insaturé, à chaîne droite ou ramifiée ; de préférence, un alkyle ou un alcényle comportant 1-8 atomes de carbone. L'invention concerne également l'utilisation de ces composés dans des produits chimiques aromatiques et des articles de fabrication.
PCT/US2004/015875 2003-05-20 2004-05-20 Alcoxy alkylsulfanyl phenols WO2004103962A2 (fr)

Priority Applications (7)

Application Number Priority Date Filing Date Title
AU2004241286A AU2004241286B2 (en) 2003-05-20 2004-05-20 Alkoxy alkylsulfanyl phenols
GB0525822A GB2417956B (en) 2003-05-20 2004-05-20 Alkoxy alkylsulfanyl phenols
MXPA05012669A MXPA05012669A (es) 2003-05-20 2004-05-20 Alcoxi alquilosulfanil feniles.
EP04752818A EP1631147A4 (fr) 2003-05-20 2004-05-20 Alcoxy alkylsulfanyl phenols
CA002526243A CA2526243A1 (fr) 2003-05-20 2004-05-20 Alcoxy alkylsulfanyl phenols
JP2006533255A JP2007506802A (ja) 2003-05-20 2004-05-20 アルコキシアルキルスルファニルフェノール
US11/283,053 US20060189509A1 (en) 2004-05-20 2005-11-21 Alkoxy alkylsulfanyl phenols

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US47172303P 2003-05-20 2003-05-20
US60/471,723 2003-05-20

Publications (2)

Publication Number Publication Date
WO2004103962A2 true WO2004103962A2 (fr) 2004-12-02
WO2004103962A3 WO2004103962A3 (fr) 2005-03-10

Family

ID=33476880

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2004/015875 WO2004103962A2 (fr) 2003-05-20 2004-05-20 Alcoxy alkylsulfanyl phenols

Country Status (10)

Country Link
EP (1) EP1631147A4 (fr)
JP (1) JP2007506802A (fr)
KR (1) KR20060021856A (fr)
CN (1) CN1798504A (fr)
AU (1) AU2004241286B2 (fr)
CA (1) CA2526243A1 (fr)
GB (1) GB2417956B (fr)
MX (1) MXPA05012669A (fr)
WO (1) WO2004103962A2 (fr)
ZA (1) ZA200509293B (fr)

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3246039A (en) * 1962-06-27 1966-04-12 Dow Chemical Co Alkenyl phenyl thioethers
BE795355A (fr) * 1972-02-14 1973-05-29 Nippon Kayaku Kk Procedes de preparation d'ethers diphenyliques et acaricides les renfermant
IL47519A (en) * 1974-07-09 1979-03-12 Roussel Uclaf 7-sulphinimidoyl(sulphimidoyl)-xanthone-2-carboxylic acid derivatives, their preparation and pharmaceutical compositions containing them
DE2644591A1 (de) * 1976-10-02 1978-04-06 Bayer Ag Verfahren zur herstellung von arylsulfoniumsalzen
JPS55133389A (en) * 1979-04-03 1980-10-17 Takeda Chem Ind Ltd Organic phosphoric ester and insecticide comprising it
US4410548A (en) * 1980-07-09 1983-10-18 Reckitt & Colman Products Limited Propanolamine derivatives
JPH01161092A (ja) * 1987-12-18 1989-06-23 Lion Corp 香料
EP1264547A1 (fr) * 2001-06-06 2002-12-11 Givaudan SA Compositions parfumantes et arômatisantes

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of EP1631147A4 *

Also Published As

Publication number Publication date
EP1631147A2 (fr) 2006-03-08
AU2004241286B2 (en) 2007-12-06
GB2417956A (en) 2006-03-15
WO2004103962A3 (fr) 2005-03-10
MXPA05012669A (es) 2007-06-14
GB2417956B (en) 2007-10-24
JP2007506802A (ja) 2007-03-22
CN1798504A (zh) 2006-07-05
EP1631147A4 (fr) 2008-04-16
KR20060021856A (ko) 2006-03-08
AU2004241286A1 (en) 2004-12-02
CA2526243A1 (fr) 2004-12-02
GB0525822D0 (en) 2006-01-25
ZA200509293B (en) 2006-09-27

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