• 专利附录
  • 专利说明
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    • 专利摘要:
    patent summary: "3-(4-isobutyl-2-methylphenyl)propanal as a perfume ingredient". The present invention relates to a compound according to formula (i) which is useful as a perfume ingredient.
    公开号:BR112015027432B1
    申请号:R112015027432-3
    申请日:2014-05-08
    公开日:2020-07-28
    发明作者:Andreas Goeke；Philip Kraft；Francis VOIROL；Yue Zou
    申请人:Givaudan Sa；
    IPC主号:
    专利说明:

    [001] This invention relates to a perfume ingredient and perfume preparations containing it. In particular, the invention relates to said perfume ingredient or perfume preparations which exhibit olfactory characteristics of mugué (lily-of-the-valleys). Even more particularly, the invention relates to said perfume preparations that do not contain, or substantially do not contain, Lilial ™. The invention further relates to methods for making said perfume ingredient and perfume preparations, as well as the use of said perfume ingredient and perfume preparations in fine fragrances and consumer products, such as personal care products. and home care products. The invention also relates to said fine fragrances and consumer products containing said perfume ingredient and perfume preparations.
    [002] Compounds having olfactory characteristics of mugué are highly sought after as perfume ingredients. These compounds are important ingredients in floral bases and can act as harmonizers in many types of fragrance creations. Compounds of this type are widely used in personal care and consumer products, as well as in fine perfumery, to generate pleasant odors or to hide unpleasant odors.
    [003] An excellent perfume ingredient widely valued for its mugué note is Lilial ™ or 3- (4-tert-butylphenyl) -2-methylpropanal (CAS 80-54-6). This compound is widely used in fine perfumery and also in products for personal care and home care. However, its use is controversial in view of the recent findings that it exhibits toxic effects on the reproductive organs of male rats and dogs. No effect was found in studies with mice, guinea pigs and primates, however, according to the Global Harmonized System (GHS) classification system ('Global Harmonized System') this compound is classified as a CMR2 material, for materials CMR category 2, it is necessary to establish that the quantities proposed for use are harmless to consumers. In view of the regulatory status of Lilial ™ it is being replaced by other perfume ingredients.
    [004] Document W02010105 873 addresses the problem of replacing Lilial ™, with the proposed solution residing in the use of mixtures of known ingredients commonly found in the perfumer's palette in order to recreate characteristics substantially similar to those of Lilial ™.
    [005] Likewise, document W02009027957 proposes a solution that resides in the formulation of combinations of known perfume ingredients that are found in the perfumer's palette.
    [006] Document W02013045301 also proposes a solution for the replacement of Lilial ™, which resides in the selection of mixtures of ingredients including the compound Lilyflo-re ™ and a certain compound based on propane indanil, in combination with other flavoring secondary ingredients. rivers.
    [007] The applicant has now discovered a new compound that can be used as a perfume ingredient in perfume compositions and fine fragrances and consumer products. More particularly, the present invention offers said new compound which has desirable olfactory characteristics of straw. More particularly, the applicant discovered the said new compound that has olfactory characteristics, which can be perceived and recognized by perfumers who are very reminiscent of the smell of Lilial ™ and can thus serve as a mere substitute for Lilial ™. In addition, the new compound has a similar or even better perfume performance compared to Lilial ™. Finally, the applicant discovered the new compound that does not have the regulatory concerns associated with Lilial ™.
    [008] Therefore, the invention offers in a first aspect a compound according to formula (I)

    [009] The compound of formula (I) has olfactory characteristics and performance characteristics substantially similar to Lilial ™. Therefore, and in opposition to the prior art proposals regarding the replacement of Lilial ™ based on mixtures of known ingredients, the present invention offers a substitute for Lilial ™ based on a single compound. This has the obvious advantage of representing an economical solution to the replacement problem, but it also makes the perfumer's creative process simpler.
    [0010] The regulatory problems involving Lilial ™ arose from the fact that it is enzymatically degraded in rats and dogs resulting in tert-butyl benzoic acid (t-BBA), which is known to inhibit glucose synthesis and the synthesis of fatty acids in vitro (McCune et al., Arch Bi-ochem Biophys (1982) 214 (1): 124-133).
    [0011] Tert-butyl benzoic acid is known to cause testicular effects in male rats (Hunter et al. Food Cosmet. Toxicol. 1965, 3: 289-298; Cagen et al. J. Am. Coll. Toxicol. 1989, 8 ( 5): 1027-1038).
    [0012] In contrast, the compound of the present invention is not susceptible to enzymatic degradation for its benzoic acid derivative. This was indeed a very surprising result considering the close structural similarity to Lilial ™. The applicant's surprising discovery that an aryl-substituted alkaline containing a methyl substituent on the ring in an ortho position in relation to the group bearing the aldehyde functionality is not susceptible to enzymatic degradation for its benzoic acid derivative offers an insight so far not known in the art, and allows perfumers to formulate formulas with a compound that although structurally similar to Lilial ™ (and therefore has olfactory properties markedly similar to those of these compounds), still does not create similar regulatory problems.
    [0013] To study the metabolism in vitro in rat hepatocytes, Lilial ™ and the compound of the present invention are incubated in the presence of suspended rat hepatocytes. The decrease in Lilial ™ and the compound of the present invention and the formation of the corresponding benzoic acid type derivative can be analyzed by GC-MS.
    Therefore, in another aspect of the present invention, a compound of formula (I) is offered which does not, or substantially does not, form any derivative of the corresponding benzoic acid type when incubated with hepatocytes isolated from rats. By "substantially no benzoic acid-type derivative" is meant that the concentration of said derivative is below the detection limit, i.e., <1% to 0%. Therefore, the compound of formula (I) provides perfumers with an eminently suitable substitute for the valuable and still problematic Lilial ™.
    [0015] Therefore, in another aspect, the invention offers the use of a compound of formula (I) as a perfume ingredient.
    [0016] The invention offers in another of its aspects the use of a compound of formula (I) in a perfume composition as a substitute for aryl-substituted alkanals, more particularly odorants based on propane substituted by aryl which are unsubstituted in the aryl ring in an ortho position in relation to the substituent with aldehyde functionality, in particular Lilial ™.
    [0017] In another aspect of the invention, a method is offered to impart an olfactory characteristic to a perfume composition, said method comprising the step of incorporating a compound of formula (I) in said perfume composition.
    [0018] In yet another aspect of the invention, a perfume composition comprising a compound according to formula (I) is offered.
    [0019] In yet another aspect of the invention there is offered a perfume composition having olfactory characteristics of mugué comprising a compound according to (I).
    [0020] In yet another aspect of the present invention there is offered a perfume composition comprising a compound according to formula (I) that is free of odorants of the alkaline type substituted by aryl, more particularly odorizers of the propanal type substituted by aryl which are unsubstituted in the aryl ring in an ortho position in relation to the substituent bearing the aldehyde functionality, in particular Lilial TM.
    [0021] A perfume composition according to the present invention can consist entirely of the compound of formula (I). However, a perfume composition may also contain, in addition to the compound of formula (I), one or more additional perfume ingredients.
    [0022] The compound of formula (I) can be present in a perfume composition in an amount depending on the particular olfactory effect that the perfumer wishes to obtain. In a particular embodiment of the present invention, a perfume composition of the present invention can contain a compound of formula (I) in an amount of 0.1 to 100% by weight of said composition.
    [0023] If one or more additional perfume ingredients are used, they can be selected from any known perfume ingredients.
    [0024] In particular, said perfume ingredients that can be used in a perfume composition according to the invention include 6-methoxy-2,6-dimethyl-heptan-1-al (methoxy-neural), 5,9-dimethyl -4,8-decadienal (ge-raldehyde), beta-methyl-3- (1-methylethyl) benzenepropanal (flori-dral), octahydro-8,8-dimethylnaphthalene-2-carbaldehyde (cyclomi-ral), alpha -methyl-1,3-benzodioxol-5-propionaldehyde (helional), 5-methyl-2- (1-methylbutyl) -5-propyl-1,3-dioxan (Troenan), 3- (o-ethylphenyl) -2 , 2-dimethylpropionaldehyde (floralozone), farnesol, 3,7,11-trimethyldodeca-1,6,10-trien-3-ol, optionally as an isomeric mixture (nerolidol), 2-methyl-4-phenylbutan-2-ol (dimethylphenylethylcarbinol), cis-4- (isopropyl) cyclohexanomethanol (maiol), 1- (1-methyl id) -4- (1-methylethyl) cyclohexane (optionally as a mixture of diastereoisomers) ) (mugethanol), (4-methyl-3-pentenyl) cyclohexenecarbaldehyde (citrusal), cyclohexyl salicylate, hexyl saliylate, benzyl salicylate, amyl salicylate, 3- (p- (2-methylpropyl) phenyl) -2-methylpropionaldehyde (silvial), 3-p-cumenyl-2-methylpropionaldehyde (cyclamen aldehyde), mixtures of: cis-tetrahydro-2-isobutyl-4-methylpyran -4-ol; trans-tetrahydro-2-isobutyl-4-methylpyran-4-ol; (florol), triethyl citrate and dipropylene glycol.
    [0025] Said perfume ingredients may additionally include Amyl Salicylate (2050-08-0); Aurantiol ® (89-43-0); Benzyl salicylate (118-58-1); Cis-3-hexenyl salicylate (65405-77-8); Citronoyl Oxyacetaldehyde (7492-67-3); Ciclemax (7775-00-0); Cyclohexyl salicylate (25485-88-5); Ciclomiral ® (68738-94-3); Citronelol (106-22-9); Geraniol (106-24-1); Cyclopentol Hc 937165 (84560-00-9); Cimal (103-95-7); Dupical (30168-23-1); Ethyl Linalool (10339-55-6); Super Floral (71077-31-1); Florhydral ® (125109-85-5); Florol ® (63500-71-0); Gyrane (24237-00-1); Hexyl Salicylate (6259-76-3); Helional (TM) (1205-17-0); Hi-droxicitronelal (107-75-5); Linalool (78-70-6); Lyral® (31906-04-4); Majantol ® (103694-68-4); Mayol ® (13828-37-0); Me-lafleur (68991-97-9); Melonal (106-72-9); Mugetanol (63767-86-2); Muguesia (56836-93-2); mugué alcohol (13351-61-6); Verdantiol (91-51-0); Peonile ® (10461-98-0); Phenoxanol ® (55066-48-3); Rossitol ® (215231-33-7); Silvial ® (6658-48-6); Suzural (6658-48-6); Muguol ® (18479-57-7); Tetrahydro Linalool (78-69-3); Acalea (84697-09-6); Dihydro Iso Jasmonato (37172-53-5); Hexyl Cinnamic Aldehyde (101-86-0); Hedione ® (24851-98-7); Acetoin (513-86-0); Adoxal (141-13-9); Aldolone ® (207228-93-1); AMBROCENIDE ® (211299-54-6); Ambroxan (3738-00-9); Azurone ® (362467-67-2); Bacdanol ® (28219-61-6); Calone 1951 ® (28940-11-6); Cetalox ® (3738-00-9); cinnamic alcohol (104-54-1); Citral (5392-40-5); Ciclabuto (67634-20-2); Cyclacet (TM) (5413-60-5); Cyclaprop ™ (17511-60-3); Cyclohexadecanol (109-29-5); Cyclohexadecenone (3100-36-5); Cyclopentade-canone (507-72-7); Delta Damascene (57378-68-4); Ebanol ® (67801-20-1); Elintaal Forte (40910-49-4); Ethyl Vanillin (121-32-4); Ethylene Brassylate (105-95-3); Exaltenone 942008 (14595-54-1); Total Exaltolide 935985 (106-02-5); Floralozone (67634-14-4); Fructalate (72903-27-6); Gamma Decalactone (706-14-9); Habanolide (111879-80-2); Helvetolide ® (141773-73-1); Hexamethylindanopyran (1222-05-5); Hydroxy-ambran ® (118562-73-5); Iso E Super ® (54464-57-2); Iso Hexenyl Cyclohexenyl Carboxaldehyde (37677-14-8); Jasmal (18871-14-2); Javanol ® (198404-98-7); Lauric Aldehyde (112-54-9); Mefranal (55066-49-4); Muscenone (63314-79-4); Tonalid ® (1506-02-1); Nectaryl ® (95962-14-4); Norlim Banol (70788-30-6); For Hydroxy Phenyl Butanone (5471-51-2); Pin Acetaldehyde (33885-51-7); Romandolide ® (236391-76-7); Sanjinol (28219-61-6); Silvanone ® Supra (109-29-5 / 507-72-7); Terpineol (8000-41-7); Vanillin (121-33-5); and Velvione ® (37609-25-9), the numbers in parentheses are CAS numbers.
    [0026] A perfume composition need not be limited to the perfume ingredients listed above. Other perfume ingredients commonly used in perfumery can be used, for example, any of those ingredients described in “Perfume and Flavor Chemicals”, S. Arctander, Allured Publishing Corporation, 1994, IL, USA, which is incorporated herein by reference , including essential oils, plant extracts, absolutes, resinoids, odorizers obtained from natural products and the like.
    [0027] The perfume ingredients contained in said perfume compositions are described above, but, of course, the perfume mixture may not be limited to the mentioned ingredients. In particular, perfume compositions can comprise adjuvants that are commonly used in perfume compositions. The term "adjuvants" refers to ingredients that can be used in a perfume composition for reasons not specifically related to the olfactory performance of that composition. For example, an adjuvant can be an ingredient that acts as an aid in the processing of an ingredient or perfume ingredients, or a composition containing said ingredients, or it can improve the handling or storage of a perfume ingredient or composition containing it, it can also be an ingredient that provides additional benefits such as imparting color or texture It can also be an ingredient that gives light resistance or chemical stability to one or more ingredients contained in a perfume ingredient or in a composition containing it. A detailed description of the nature and type of adjuvants commonly used in perfume compositions. containing them cannot be complete, but it must be said that those ingredients are well known to the person skilled in the art. Examples of adjuvants include solvents and cosolvents; surfactants and emulsifiers; viscosity and rheology modifiers; thickening and gelling agents; preservative materials; pigments, dyes and coloring substances; extenders, fillers and reinforcing agents; stabilizers against the damaging effects of heat and light, bulking agents, acidulants, buffering agents and anti-oxidants.
    [0028] In addition, any one or more of the perfume or adjuvant ingredients employed in the present invention can be formulated in a delivery vehicle if desired to give a desired effect. Distribution vehicles can include encapsulated. Alternatively, a delivery vehicle can be in the form of a solid support, for example, a polymeric support material to which one or more perfume or adjuvant ingredients can be chemically or physically attached. In addition, one or more perfume or adjuvant ingredients can be dissolved or dispersed in a matrix material, which serves to control the rate at which said ingredient or ingredients detach from it. In yet an alternative embodiment, one or more ingredients or adjuvants can be supported on a porous substrate, such as a cyclo-dextrin or a zeolite or other organic material. In yet another embodiment, one or more perfume ingredients can be offered in the form of a pro-perfume, which will react in a suitable environment to release the perfume ingredient in a controlled manner.
    [0029] In view of the above, it will be appreciated that a perfume composition can be at least partially in solid form, in gel form, in foam form and / or in liquid form. If it is present in solid form, it can then take the form of granules, powders or tablets.
    [0030] The compound of formula (I), or the perfume compositions described in this invention, can be used to add a characteristic odor, in particular a mugué smell, to all types of compositions for personal care and care domestic.
    [0031] In accordance with another aspect of the present invention, a method is offered to impart olfactory characteristics of muugué to a composition comprising the step of adding to said composition a compound according to formula (I) or a perfume composition containing the said compound.
    [0032] A compound of formula (I) as a perfume ingredient, or when used in perfume compositions, can generate particularly substantive and long-lasting olfactory characteristics.
    [0033] The compound of formula (I) is a particularly impacting perfume ingredient. The impact that a perfume ingredient has is related to its odor index. odor index is the ratio of vapor pressure to the borderline detection concentration.
    [0034] The compound of formula (I) has an extremely high odor index, specifically 559,071. Comparative perfume ingredients are not impactful. For example, Lilial ™ has an odor index of only 32’978 and cyclamen aldehyde has an odor index of only 21’986.
    [0035] The remarkably high odor index of the compound of formula (I) is significant in the sense that there is a need for sustainability and the presentation of impacting perfume ingredients allows perfumers to create desirable fragrance accords with lower concentrations perfume ingredients.
    [0036] Consumer products such as compositions for personal care and home care include, but are not limited to, a textile treatment product, an ironing aid, a cleaning cloth, a laundry detergent, a product cleaning agents, in particular, for hard and / or soft surfaces, a household cleaning product, a care product, a washing care product, a laundry care product, an environment odorizer, an air purifier , a conditioner, a colorant, a fabric conditioner, a conditional substrate, a pharmaceutical product, a crop protection product, a polisher, a foodstuff, a cosmetic product, a fertilizer, a building material, an adhesive, a bleach, a descaler, a car care product, a floor care product, a kitchenware care product, a leather care product or a care product of furniture, a polisher, a disinfectant, an odorizer, a mode remover and / or a precursor to the products mentioned above.
    [0037] Those skilled in the art are fully aware of the applicability of perfume ingredients, and compositions for compositions for personal care and home care, and a very detailed description of such compositions is not offered in this report. However, specific compositions that can be mentioned include cleaning compositions; car care compositions; cosmetic compositions, compositions for the treatment of textiles; and air purifiers and compositions for the care of environments.
    [0038] Cleaning products include: - Toilet cleaners or sanitary cleaners, in other words, products for cleaning toilets and urinals, these products being preferably presented in the form of powders, tablets, tablets or liquids, preferably gels. In addition to other typical ingredients such as surfactants, they generally include organic acids, for example, citric acid and / or lactic acid) or sodium hydrogen sulfate, amidosulfuric acid or phosphoric acid to remove sludge or urine residue; Pipe cleaning products or drain cleaners. These are typically strongly alkaline products that generally serve to remove pipe clogging comprising such organic materials as hair, fat, food residues, soap deposits, and the like. Additions of Al powder or Zn powder can serve to form H2 gas with an effervescence effect. Possible ingredients are commonly alkalis, alkaline salts, oxidizing agents, and neutral salts. Presentation forms in powder form also include sodium nitrate and sodium chloride. Liquid cleaning products for pipes can also preferably include hypochlorite. There are also enzyme-based drain cleaners. Acidic products are also possible; Universal or multipurpose or general purpose cleaners. These are cleaners that can be used universally on all hard surfaces for domestic and commercial use that can be removed wet or damp. In general, they are neutral, slightly alkaline or slightly acidic products, especially liquid products. Multipurpose or general purpose cleaners generally contain surfactants, reinforcers, solvents and hydrotropes, dyes, preservatives, and the like; Multipurpose cleaners with special disinfectant properties. They additionally include active antimicrobial ingredients (for example, aldehydes, alcohols, quaternary ammonium compounds, amphoteric surfactants, tri-closan); Sanitary cleaners. These are products for cleaning bathtubs and toilets. Alkaline sanitary cleaners are preferably used to remove greasy dirt, while acidic sanitary cleaners are used, in particular, to remove slime. Sanitary cleaners also advantageously have considerable disinfectant action, particularly strongly alkaline sanitary cleaners that contain chlorine; Oven cleaners or grid cleaners that can be offered in the form of foam gels or sprays. They are usually used to remove burnt or charred food residues. Oven cleaners are preferably presented in the form of a strongly alkaline formulation using, for example, sodium hydroxide, sodium metasilicate, 2-aminoethanol. In addition, they generally contain anionic and / or non-ionic surfactants, water-soluble solvents, and, in some cases, thickeners such as polycarboxylates and carboxymethylcellulose; Metal polishers. These are cleaners for particular types of metal such as stainless steel or silver. Stainless steel cleaners preferably contain, in addition to acids (preferably up to 3% by weight, for example, citric acid, lactic acid), surfactants (in particular, up to 5% by weight, preferably non-ionic and / or anionic surfactants) , and water, and also solvents (preferably up to 15% by weight) to remove greasy dirt, and also other compounds such as thickeners and preservatives. Very fine polishing structures are also included in products for stainless steel surfaces, preferably glossy. Silver polishers, in turn, can be presented in an acid formulation. In particular, to remove black deposits of silver sulfide, they preferably contain complexing agents (for example, thiourea, sodium thiosulfate). Typical forms of presentation are polishing cloths, immersion baths, pastes, and liquids. Dark discolorations (oxide layers) are removed using copper cleaners and non-ferrous metal cleaners (for example, for brass and bronze). They generally have a weakly alkaline formulation (preferably with ammonia) and generally contain polishing agents and also, preferably, ammonium soaps and / or complexing agents; Glass cleaners and window cleaners. These products are preferably used to remove dust, especially greasy dust, from glass surfaces. Preferably they contain compounds such as anionic and / or non-ionic surfactants (in particular, up to 5% by weight), ammonia and / or ethanolamine (in particular, up to 1% by weight), ethanol and / or 2-propanol, glycol ethers (in particular, 10-30% by weight), water, preservatives, dyes, anti-fog agents and the like; and Cleaning products for special purposes, examples of which are for glass ceramic plates, as well as stain-removing carpet cleaners.
    [0039] Automotive products include: -Paint preservatives, paint polishers, paint cleaners, washing preservatives, car wash shampoos, car wash products and car waxes, metallic finish polishers, protective films for metallic finishes, plastic cleaners, tar removers, filter cleaners, engine cleaners, and the like.
    [0040] Cosmetic products include :-( a) cosmetic products for skin care, especially bath products, skin washing and cleaning products, skin care products, eye makeup, lip care products , nail care products, intimate care products, foot care products; (b) cosmetic products with specific effects, especially sunscreens, tanning products, depigmentation products, deodorants, antiperspirants, hair removal products, shaving products, perfumes; (c) cosmetic products for the care of teeth, especially dental products and for oral care, products for the care of teeth, dental cleaner, denture adhesives; and (d) cosmetic hair care products, especially hair shampoos, hair care products, hair fixers, hair styling products, and hair dyes.
    [0041] Products for the treatment of textiles include: - Fabric detergents or conditioners, for example, whether in liquid or solid form.
    [0042] Air purifiers and air fresheners include: -Products that preferably contain volatile and usually pleasant-smelling compounds that advantageously can even in very small quantities to hide unpleasant odors. Air fresheners for living areas contain, in particular, natural and synthetic essential oils such as pine oils, citrus oil, eucalyptus oil, lavender oil, and the like, in quantities, for example, up to 50% by weight . As aerosols they tend to contain lesser amounts of such essential oils, for example less than 5% or less than 2% by weight, but additionally include compounds such as acetaldehyde (in particular, <0.5% by weight) , isopropyl alcohol (in particular, <5% by weight), mineral oil (in particular, <5% by weight), and propellants. Other forms of presentation include sticks and tablets. They are produced using typically a concentrated gel comprising essential oils. It is also possible to add formaldehyde (for preservation) and chlorophyll (preferably <5% by weight), as well as other ingredients. Air purifiers, however, are not limited to living areas, but are also intended for automobiles, cabinets, dishwashers, refrigerators or shoes, and their use even in vacuum cleaners is a possibility. For domestic use (eg in cabinets), for example, in addition to olfactory enhancers, disinfectants containing preferably compounds such as calcium phosphate, talc, stearin, and essential oils are also used, these products being presented, for example, in the form of sachets.
    [0043] The consumer product compositions mentioned above, particularly those for use in washing or cleaning applications may contain one or more of the following substances:
    [0044] Reinforcing substances, surfactants, enzymes, bleaching agents, such as organic and / or inorganic peroxygen compounds, peroxygen activators, water-miscible organic solvents, sequestering agents, electrolytes, pH regulators, thickeners, and other adjuvants such as active anti-stain substances, optical brighteners, grime inhibitors, color transfer inhibitors, foam regulators, and dyes.
    [0045] Surfactants include anionic surfactants, non-ionic surfactants, and mixtures thereof, but cationic surfactants are also appropriate. Suitable non-ionic surfactants are, in particular, ethoxylation and / or propoxylation products of alkyl glycosides and / or linear or branched alcohols, each having 12 to 18 carbon atoms in the alkyl portion and 3 to 20, preferably 4 to 10, alkyl ether groups. Corresponding ethoxylation and / or propoxylation products of N-alkylamines, vicinal diols, fatty acid esters and fatty acid amides are also useful, corresponding, in terms of the alkyl portion, to the long-chain alcohol derivatives mentioned above, and alkylphenols having 5 to 12 carbon atoms in the alkyl residue.
    [0046] Suitable anionic surfactants include soaps, and those containing sulfate or sulfonate groups preferably having alkaline ions such as cations. Soaps include alkaline salts of saturated or unsaturated fatty acids having 12 to 18 carbon atoms. Such fatty acids can also be used in a form that is not completely neutralized. Included among the useful sulphate-type surfactants are the salts of the fatty alcohol sulfuric acid ester esters having 12 to 18 carbon atoms, and the sulfated products of the nonionic surfactants mentioned above having a low degree of ethoxylation. Included among useful sulfonate-type surfactants are linear alkylbenzenesulfonates having 9 to 14 carbon atoms in the alkyl portion, alkanesulfonates having 12 to 18 carbon atoms, and olefin sulfonates having 12 to 18 carbon atoms that are produced by mono reaction -corresponding sulfur trioxide olefins, as well as esters of alpha-sulfograxic acids which are produced by sulfonation of methyl or ethyl esters of fatty acids.
    [0047] Cationic surfactants include esterquats and / or quaternary ammonium compounds (QACs). QACs can be produced by reacting tertiary amines with alkylating agents such as methyl chloride, benzyl chloride, dimethyl sulfate, dodecyl bromide, but also ethylene oxide. The alkylation of tertiary amines having a long alkyl residue and two methyl groups occurs particularly easily, and quaternization of tertiary amines having two long alkyl residues and a methyl group can also be carried out using methyl chloride under mild conditions. Amines having three long alkyl residues or hydroxy-substituted alkyl residues have low reactivity, and are quaternized, for example, using dimethyl sulfate. Suitable QACs are, for example, benzalkonium chloride (N-alkyl-N, N-dimethylbenzylammonium chloride), benzalcon B (m, p-dichlorobenzyldimethyl-C12-alkylammonium chloride), benzoxonium chloride (benzylodeodyl-chloride chloride) bis (2-hydroxyethyl) ammonium), cetrimony bromide (N-hexadecyl-N, N-trimethylammonium bromide), benzethonium chloride (N, N-dimethyl-N- [2- [2- [- ( 1,1,3,3-tetramethylbutyl) phenoxy] ethoxy] ethyl] benzylammonium), di-alkyldimethylammonium chlorides such as di-n-decyldimethylammonium chloride, didecyldimethylammonium bromide, dioctyldimethylammonium chloride, 1-cetylpyridinium chloride, and thiazoline, as well as mixtures thereof. Preferred QACs are benzalkonium chlorides having C8 to C22 alkyl residues, in particular C12 to C14 chloride alkyl benzyl methylammonium.
    [0048] Esterquats include commercially available methylhydroxyalkyloxyoxyalkylammonium methosulfates marketed by Stepan company under the trade name Stepantex ™, or Cognis Deutschland GmbH products known by the trade name Dehyquat ™, or Rewoquat ™ products from Goldschmidt-Witco.
    [0049] Surfactants can be used in amounts of 5% by weight to 50% by weight in a consumer product of the present invention.
    [0050] Reinforcers include water-soluble and / or water-insoluble organic and / or inorganic reinforcers. In particular, they include the water-soluble organic reinforcing substances are polycarboxylic acids, more particularly citric acid and sugar acids, monomeric and polymeric amino-polycarboxylic acids, in particular methylglycinadiacetic acid, nitrilotriacetic acid, and ethylenediaminetetra-acetic acid, as well as polyaspartic, polyphosphonic acids in particular aminotris (methylene-phosphonic acid), ethylene diaminetetracis (methylenephosphonic acid), and 1-hydroxyethane-1,1-diphosphonic acid, hydroxy polymeric compounds such as dextrin, as well as polymeric (po-li) carboxylic acids, polymeric acrylic acids, methacrylic acids, maleic acids, and mixed polymers thereof, which may also contain small proportions of polymerizable substances without carboxylic acid functionality. The relative molecular weight of unsaturated carboxylic acid homopolymers generally ranges between 5000 and 200,000, and that of copolymers between 2000 and 200,000, in each case based on free acid. Suitable compounds of this class are copolymers of acrylic acid or methacrylic acid with vinyl ethers, such as vinyl methyl ethers, vinyl esters, ethylene, propylene, and styrene, in which the acid ratio is at least 50% by weight. It is also possible to use, as water-soluble organic reinforcing substances, terpolymers that contain two unsaturated acids and / or salts thereof as monomers and, as a third monomer, vinyl alcohol and / or a vinyl alcohol derivative or a carbohydrate. The first acid monomer or salt thereof can be derived from an ethylenically unsaturated C3 to C8 carboxylic acid. The second acid monomer or salt thereof can be a derivative of a C4 to C8 dicarboxylic acid, for example, maleic acid. The third monomeric unit consists of alcohol vinyl and / or an esterified alcohol vinyl. Polymers can contain 60% by weight to 95% by weight, in particular 70% by weight to 90% by weight, of (meth) acrylic acid or (meth) acrylate, as well as 5% by weight to 40% by weight of vinyl. alcohol and / or vinyl acetate. Particular polymers are those in which the weight ratio of (meth) acrylic acid respectively (meth) acrylate to maleic acid or maleate varies between 1: 1 and 4: 1. Both amounts and weight ratios are given based on acids. The second acid monomer or salt thereof may also have a regulatory sequence, a derivative of an allylsulfonic acid that is substituted in position 2 with an alkyl radical, for example a C1 to C4 alkyl radical, or with an aromatic radical that can be derived from benzene or benzene derivatives. Terpolymers can contain 40% by weight to 60% by weight, in particular 45 to 55% by weight, of (meth) acrylic acid or (meth) acrylate, particularly preferably acrylic acid or acrylate, 10% by weight to 30% in weight, preferably 15% by weight to 25% by weight of metallo-sulfonic acid or methylsulfonate, and as a third monomer 15% by weight to 40% by weight, preferably 20% by weight to 40% by weight of a carbohydrate. This carbohydrate can be, for example, a mono-, di-, oligo-, or poly-saccharide, for example, sucrose. Terpolymers generally have a relative molecular weight between 1000 and 200,000. Other copolymers comprise, such as monomers, acrolein and acrylic acid / acrylic acid salts, or vinyl acetate. Especially for the manufacture of liquid detergents, organic reinforcing substances can be used in the form of aqueous solutions, for example, a 30 to 50 weight percent aqueous solution. All the acids mentioned above can be used in the form of their water-soluble salts, in particular their alkaline salts.
    [0051] Organic reinforcing substances can be used in amounts up to 40% by weight.
    [0052] Water-soluble inorganic reinforcing materials include silicates and alkaline polyphosphates, for example, sodium triphosphate. Crystalline or amorphous alkaline aluminosilicates, for example, crystalline sodium aluminosilicates, can also be used as water-insoluble and water-dispersible materials, in amounts up to 50% by weight, for example. Aluminosilicates typically comprise particles having a particle size of less than 30 [mu] m.
    [0053] Alkaline crystalline silicates can also be used, either alone or used with amorphous silicates. Alkaline silicates usable in the consumer products of the present invention as detention enhancers may have an alkali oxide to SiO2 molar ratio of less than 0.95, in particular from 1: 1.1 to 1:12, and may be present in amorphous or crystalline form. Alkaline silicates can be sodium silicates, in particular amorphous sodium silicates, having a Na2O: SiO2 molar ratio of 1: 2 to 1: 2.8.
    [0054] Reinforcing substances can be present in consumer product compositions according to the present invention at levels of up to 60% by weight.
    [0055] Peroxygen compounds include organic peracids or peracid salts of organic acids such as phthalimid percapronic acid, perbenzoic acid, or diperdodecanedioic acid salts, hydrogen peroxide, and inorganic salts that release hydrogen peroxide under application conditions, such as perborate , percarbonate, and / or persi-licate. If solid peroxygen compounds are used, they can be used in the form of powders or granules, which in principle can also be encapsulated in a known manner.
    [0056] Peroxygen compounds can be used in amounts up to 50% by weight. The addition of small amounts of known bleaching agent stabilizers, for example, phosphonates, borates respectively metaborates, and metasilicates, as well as magnesium salts such as magnesium sulfate, may be useful.
    [0057] Compounds which, under perhydrolysis conditions, give aliphatic peroxocarboxylic acids preferably having 1 to 10 carbon atoms, in particular 2 to 4 carbon atoms, and / or perbenzoic acid (optionally substituted), can be used as activators bleaching. Substances that carry O-and / or N-acyl groups having the number of carbon atoms mentioned above, and / or optionally substituted benzoyl groups, are suitable. Multiple acylated alkylenediamines, in particular tetraacetylethylenediamine (TAED), acylated triazine derivatives, in particular 1,5-diacetyl-2,4-dioxo-hexahydro-1,3,5-triazine (DADHT), acylated glycolurils, in particular tetraacetyl glycoluryl (TAGU), N-acylimides, in particular N-nonanoyl succinimide (NOSI), acylated phenolsulfonates, in particular n-nonanoyl or isononanoyl oxybenzenesulfonate (n- or iso-NOBS), anhydrides carboxylic acid, in particular phthalic acid anhydride, acylated polyvalent alcohols, in particular triacetin, ethylene glycol diacetate, 2,5-diacetoxy-2,5-dihydrofuran, and enol esters, as well as acetylated sorbitol and mannitol respectively mixtures of the (SORMAN), derivatives of acylated sugars, in particular pentaacetylglucose (PAG), pentaacetylfructose, tetraacetylxylose and octaacetyl lactose, as well as acetylated glutamine and gluconolactone, optionally N-alkylated, and / or N- lactams acylated compounds, for example N-benzoylcaprolactam, can m be employed. Acyl acetates and hydrophilically substituted acyl lactams can also be used. Combinations of conventional bleach activators can also be used. Such bleach activators can be contained in the usual amount range, preferably in amounts of 1% by weight to 10% by weight, in particular 2% by weight to 8% by weight, based on the total agent.
    [0058] In addition to the conventional bleach activators mentioned above or in place of them, sulfinimines and / or transition metal salts or bleach enhancing transition metal complexes may also be contained as bleach catalysts. Included among the appropriate transition metal compounds are, in particular, salen complexes of manganese, iron, cobalt, ruenium, or molybdenum and nitrogen analog compounds thereof, carbonyl complexes of manganese, iron, cobalt, ruthenium, or molybdenum , manganese, iron, cobalt, ruthenium, molybdenum, titanium, vanadium, and copper complexes having nitrogen-containing tripod binders, cobalt, iron, copper, and ruthenium amine complexes. Combinations of bleach activators and bleach catalysts based on transition metal can also be used. Bleaching-enhancing transition metal complexes, in particular having the central atoms Mn, Fe, Co, Cu, Mo, V, Ti, and / or Ru, can be used in conventional amounts, such as up to 1% by weight based weight of the consumer product composition.
    [0059] Suitable enzymes that can be used in consumer product compositions are those in the class of proteases, cutinases, amylases, pullulanases, hemicellulose, cellulases, lipases, oxidases, and peroxidases, as well as mixtures thereof. Enzymatically active substances recovered from fungi or bacteria, such as Bacillus subtilis, Bacillus licheniformis, Streptomyces gri-seu, Humicola lanuginosa, Humicola insolens, Pseudomonas pseudoalcaligenes, or Pseudomonas cepacia, are also suitable. Enzymes that are used as applicable can be adsorbed on carrier substances and / or embedded in wrapping substances to protect them from premature inactivation. They can be contained in washing products according to the present invention in amounts typically less than 5% by weight.
    [0060] Optical brighteners include derivatives of diamino-stilbenedisulfonic acid or alkali metal salts thereof. Suitable are, for example, 4,4'-bis (2-anilino-4-morpholino-1,3,5-triazinyl-6-amino) stilbene-2,2'-disulfonic acid, or compounds of similar structure that carry, in place of the morpholino group, a diethanolamino group, a methylamino group, an anilino group, or a 2-methoxyethylamino group. Substituted diphenylstyrene type brighteners may also be present, for example, the alkaline salts of 4,4'-bis (2-sulfostyryl) diphenyl, 4,4'-bis (4-chloro-3-sulfostyryl) diphenyl, or 4- (4-chlorostyr I) -4 '- (2-sulfo-styrene) diphenyl. Mixtures of the optical brighteners mentioned above can also be used.
    [0061] Foam inhibitors include organopolysiloxanes and mixtures thereof with optionally silicated microfine acid, as well as paraffin waxes and mixtures thereof with silanic acid or bis-alkylenediamides of fatty acids. Mixtures of different foam inhibitors, for example, those made of silicones, paraffins, or waxes, can also be used. Foam inhibitors, in particular foam inhibitors containing silicone and / or paraffin, are preferably attached to a granular carrier substance that is soluble or dispersible in water. Mixtures of paraffins and bistearylethylenediamide, in particular, can be used.
    [0062] Anti-stain active substances are those compounds that positively influence the ability of oils and fats to be removed from textiles. This effect is particularly evident when the dirty textile is a textile that has previously been washed several times with a cleaning agent according to the present invention that contains this oil and fat releasing component. Preferred oil and fat releasing components include, for example, non-ionic cellulose ethers such as methyl cellulose and methyl hydroxypropyl cellulose having a proportion of 15 to 30% by weight of methoxy groups and a ratio of 1 and 15% by weight of hydroxypropoxy groups, in each case based on non-ionic cellulose ethers, as well as polymers, known from the existing technique, of phthalic acid and / or terephthalic acid, respectively, of their derivatives with monomeric and / or polymeric diols , in particular polymers of ethylene terephthalates and / or polyethylene glycol terephthalates or anionically and / or non-ionically modified derivatives thereof.
    [0063] Color transfer inhibitors include polymers of vinylpyrrolidone, vinylimidazole, vinylpyridine-N-oxide, or copolymers thereof. Also suitable are polyvinylpyrrolidones having molecular weights from 15,000 to 50,000 and polyvinylpyrrolidones having molecular weights greater than 1,000,000, in particular from 1,500,000 to 4,000,000, N-vi ni I imid a l / N-vi copolymers ni I pyridine, polyvinyloxazolidones, copolymers based on vinylic monomers and carboxylic acid amides, polyesters and polyamides containing pyrrolidone groups, polyamidoamines and grafted polyethylenimines, polymers having amide group consisting of secondary amines , polyamine-N-oxide polymers, polyvinyl alcohols, and copolymers based on acrylamidoalkenyl sulfonic acids. It is also possible, however, to use enzyme systems comprising a peroxidase and hydrogen peroxide or a substance that produces hydrogen peroxide in water.
    [0064] Grime inhibitors are those materials that retain the dirt that has come off the textile fibers suspended in a washing medium. Water-soluble colloids, usually of an organic nature, are suitable for this purpose, for example, starch, glue, gelatin, salts of carboxylic ether acids or sulphonic ether of starch or cellulose, or salts of esters of sulfuric acid acids of cellulose or starch. Water-soluble polyamides containing acidic groups are also suitable for this purpose. Starch derivatives other than those mentioned above can also be used, for example, aldehyde starches. Cellulose ethers such as carboxymethyl cellulose (sodium salt), methyl cellulose, hydroxyalkyl cellulose, and mixed ethers such as methyl hydroxyethyl cellulose, methyl hydroxypropyl cellulose, methyl carboxymethyl cellulose, and mixtures of the same can also be used, for example, in amounts 0.1 to 5% by weight based on the weight of the consumer product.
    [0065] Organic solvents include alcohols having 1 to 4 carbon atoms, in particular methanol, ethanol, isopropa-nol, and tert-butanol, diols having 2 to 4 carbon atoms, in particular ethylene glycol and propylene glycol, as well as mixtures of them, and ethers derivable from the classes of compounds mentioned above. Water miscible solvents of this type are present in washing products according to the present invention in amounts typically not exceeding 30% by weight.
    [0066] pH regulators include citric acid, acetic acid, tartaric acid, malic acid, lactic acid, glycolic acid, succinic acid, glutaric acid, and / or adipic acid, but also mineral acids, in particular sulfuric acid , or bases, in particular ammonium hydroxides or alkali hydroxides. PH regulators of this type are contained in the agents according to the present invention in quantities preferably not exceeding 20% by weight, in particular from 1.2% by weight to 17% by weight.
    [0067] The compound of the present invention can be used particularly for perfumed household products containing enzymes, such as those described above, and in particular products for the treatment of textiles, such as detergents, containing enzymes.
    [0068] Below is a series of examples that serve to better illustrate the invention. Example 1 Synthesis of 3- (4-isobutyl-2-methylphenyl) propanal
    A) l-lsobutyl-4- (3- (methoxymethoxy) propyl) benzene:
    [0069] To a solution of 3- (4-isobutylphenyl) propan-1-ol (641.0 g, 3.33 mol) in 1.5 L of dimethoxyethane was added lithium bromide (14.5 g) and p-toluenesulfonic acid (10.0 g). The mixture was stirred for 20 hours at room temperature and then poured with stirring in aqueous sodium hydroxide (200 ml, 2M). The organic phase was washed neutral with a diluted NaCI solution, dried (MgSCU) and evaporated in vacuo to give 1-isobutyl 4- (3- (methoxymethoxy) propyl) benzene (721.0 g, 91.5%) like a colorless oil. 1H-NMR (400 MHz, CDCl3): 8 = 7.17-7.08 (m, 4H), 4.68 (s, 2H), 3.59 (t, J = 6.4 Hz, 2H), 3.42 (s, 3H), 2.74 (t, J = 7.8 Hz, 2H), 2.49 (d, J = 7.1 Hz, 2H), 2.0-1.84 (m , 3H), 0.95 (d, J = 6.6 Hz, 6H) ppm. 13C-NMR (400 MHz, CDCI3): 8 = 139.5 (s), 139.4 (s), 129.5 (d, 2C), 128.5 (d, 2C), 96.9 (t) , 67.6 (t), 55.6 (q), 45.5 (t), 32.5 (t), 31.9 (t), 30.7 (d), 22.8 (q, 2C ) ppm. GC / MS (El): 236 (M +), 204 (29), 161 (65), 147 (59), 131 (100), 117 (49), 105 (37), 104 (26), 91 (46 ), 57 (29), 45 (64). B) 8-1sobutiI-1,3,4,5-tetrahydrobenzo [c] oxepine
    [0070] To a cold solution (0 ° C) of AICI3 (10.33 g) in dichloromethane (80 ml) was added in drops a solution of 1-isobutyl-4- (3- (methoxymethoxy) propyl) benzene (13.9 g, 55.36 mmols) in dichloromethane (40 ml). After the addition was complete, the mixture was stirred for 1.5 hours at 5 ° C and poured into an aqueous sodium hydroxide solution (80 ml, 2M). The mixture was extracted with MTBE and the organic layers were washed with water and brine, dried (MgSO4) and evaporated in vacuo to give a clear yellowish oil (11.91 g) which was first distilled in Kugelrohr (125 ° C, 0, 12 mbar) and then purified by chromatography to give 8-isobutyl-1,3,4,5-tetrahydrobenzo [c] oxepine (6.95, 61%) as a colorless oil. Odor: 1H NMR (400 MHz, CDCl3): 8 = 7.11 (d, J = 7.33 Hz, 1H), 7.01-6.97 (m, 2H), 4.66 (s, 2H) , 4.09-4.06 (m, 2H), 3.02-2.98 (m, 2H), 2.46 (d, J = 7.33 Hz, 2H), 1.93-1.82 (m, 1H), 0.94 (d, J = 6.8 Hz, 6H) ppm. 13C-NMR (400 MHz, CDCI3): 8 = 140.3 (s), 140.05 (s), 139.9 (s), 129.8 (d), 129.3 (d), 128.8 (d), 76.1 (t), 75.6 (t), 45.3 (t), 35.5 (t), 30.9 (t), 30.6 (d), 22.8 ( q, 2C) ppm. GC / MS (El): 204 (M +, 33), 161 (100), 147 (44), 143 (58), 131 (31), 129 (28), 119 (61), 115 (34), 105 (43), 91 (34). C) 3- (4-lsobutyl-2-methylphenyl) propan-1-ol
    [0071] A catalytic amount of boron trifluoride ether complex (0.3 g) was added to a suspension of Pd / C (10%, 0.5 g) and 8-isobutyl-1,3,4,5 -tetrahydrobenzo [c] oxepin (50.0 g, 244.5 mmols). The mixture was hydrogenated in an autoclave for 2 hours at 9 bar and 50 ° C for 2 hours. The suspension was filtered and distilled on thin film (160 ° C, 0.11 mbar) to give 3- (4-isobutyl-2-methylphenyl) propan-1-ol (45.39 g, 89.9%) as a colorless viscous oil. Odor: 1H-NMR (400 MHz, CDCl3): 8 = 7.10 (d, J = 7.6 Hz, 1H), 6.99-6.94 (m, 2H), 3.75 (t, J = 6.6 Hz, 2H), 2.74-2.68 (m, 2H), 2.47 (d, J = 7.3 Hz, 2H), 2.34 (s, 3H), 2.19 (s, 1H, -OH), 1.95-1.84 (m, 1H), 0.96 (d, J = 6.6 Hz, 6H) ppm. 13C-NMR (400 MHz, CDCI3): 8 = 139.7 (s), 137.6 (s), 135.9 (s), 131.5 (d), 128.9 (d), 127.1 (d), 63.0 (t), 45.4 (t), 33.5 (t), 30.6 (d), 29.5 (t), 22.9 (q), 19.7 ( q) ppm. GC / MS (El): 206 (M +, 25), 163 (100), 161 (27), 145 (84), 119 (53), 117 (33), 115 (32), 105 (41), 91 (40), 41 (23). D) 3- (4-lsobutyl-2-methylphenyl) propanal
    [0072] Pyridinium chlorochromate (PCC, 37.6 g, 174.49 mmols) was added gradually to a solution of 3- (4-isobutyl-2-methylphenyl) propan-1-ol (30.0 g, 145, 41 mmols) in dichloromethane (300 ml); the temperature rose to 35 ° C. The mixture was stirred for 1 hour and an additional amount of PCC (10 g, 46.4 mmols) was added and stirring continued for another 15 minutes. The reaction mixture was filtered through Florisil and silica gel. The filtrate was evaporated in vacuo (23.2g) and distilled in kugelrohr (143 ° C, 0.08 mbar) to give 3- (4-isobutyl-2-methylphenyl) propanal (19.01 g, 64%) as a colorless oil. Flavor: floral, aldehydic, green, elastic, lilac, water. 1H-NMR (400 MHz, CDCl3): S = 9.88 (t, J = 1.5 Hz, 1H), 7.07 (d, J = 7.6 Hz, 1H), 7.0-6, 95 (m, 2H), 2.98-2.93 (m, 2H), 2.79-2.74 (m, 2H), 2.46 (d, J = 7.1 Hz, 2H), 2 , 33 (s, 3H), 1.95-1.82 (m, 1H), 0.95 (d, J = 6.6 Hz, 6H) ppm. 13C-NMR (400 MHz, CDCI3): 5 = 202.2 (d), 140.2 (s), 136 (s), 135.9 (s), 131.6 (d), 128.6 (d ), 127.3 (d), 45.4 (t), 44.6 (t), 30.6 (d), 25.5 (t), 22.9 (q), 19.7 (q) ppm. GC / MS (El): 204 (M +, 23), 161 (100), 147 (26), 143 (49), 119 (84), 118 (34), 117 (33), 115 (33), 105 (59), 91 (36). Example 2
    [0073] In this floral perfume formulation the 3- (4-isobutyl-2-methylphenyl) propanal increases the floral character and leaves this sandalwood composition fresher with a pleasant floral hue, emphasizing the softness of the wood while maintaining a character spicy and fruity.

    Example 3 Study of metabolism in vitro. A comparison of a compound of formula (I) and Lilial ™.
    [0074] Cryopreserved hepatocytes from male rats (Sprague Dawley; Lifetechnologies) were thawed, washed in cryopreserved hepatocyte recovery medium (CHRM; Lifetechnologies) and suspended in Williams E medium (WEM; Lifetechnologies). Lilial ™, or the compound of formula (I) (final concentration: 100 pM) was added to the cells (1 x 10 6 viable cells / ml) and the suspensions were incubated for up to 4 hours at 37 ° C on a duplicate shaker. Testosterone metabolism was monitored as a positive control. The decrease in test compounds and the formation of the corresponding benzoic acid type derivative were determined by GC-MS analysis of the methyl esters formed after derivatization with tri-methylsilyl-diazomethane (Sigma-Aldrich) in methanol. The test compounds reacted with diazomethane giving a methyl ketone which was used for the quantification of Lilial ™ and the compound of formula (I). Metabolism was stopped with ice-cold 1 M HCI, and samples were extracted with tert-butyl methyl ether (MTBE) and analyzed by GC-MS. Incubations containing testosterone as a control were also stopped with ice-cold 1 M HCI, centrifuged to separate cells, filtered and the decrease in testosterone was analyzed by LC-MS. To quantify the decrease in test substances and the formation of benzoic acid metabolites, calibration curves of reference materials (Lilial ™ and the compound of formula (I), tert-butyl benzoic acid (Fluka) were prepared in incubation medium hepatocytes and analyzed in the same way as the hepatocyte samples.
    [0075] A rapid decrease in testosterone as a positive control was observed indicating that hepatocytes were metabolically active. The compound of formula (I) and Lilial ™ were rapidly metabolized to rat hepatocytes and no residual compound was measured after 4 hours. Although tert-butyl benzoic acid was detected as a metabolite of Lilial ™ (3.4-3.9 pM), no derivative of the benzoic acid type was formed from the compound of formula I (Table 1). The detection limit was <1 pM. Table 1. Concentrations of Lilial ™ and a compound of formula and corresponding benzoic acid metabolites in rat hepatocytes after 4 hours of incubation. The initial 0 hour test concentration was 100 µM.


    Therefore, the substitution of methyl in the benzene ring of the compound of formula (I) prevents the formation of the corresponding benzoic acid derivative in vitro. As benzoic acid derivatives such as tert-butyl benzoic acid from Lilial ™ cause reproductive toxicity in male rats, these toxic effects in male rats are prevented by the ortho-substituent of the compound of formula (I)
    权利要求:
    Claims (9)
    [0001]
    1. Compound characterized by being according to formula (I)
    [0002]
    2. Use of a compound according to formula (I), characterized as being a perfume ingredient.
    [0003]
    Use of a compound according to claim 2, characterized by the fact that the perfume ingredient has olfactory characteristics of mugué.
    [0004]
    4. Perfume composition characterized by comprising a compound according to formula (I).
    [0005]
    5. Perfume composition according to king-vindication 4, characterized by the fact that it is free of alkali-substituted aryl-based odors, more particularly aryl-substituted propanals, which are not substituted in the aryl ring in a position ortho in relation to the substituent with aldehyde functionality, in particular Lilial ™.
    [0006]
    6. Perfume composition according to king-vindication 4 or 5, characterized by the fact that it comprises one or more additional fragrance ingredients.
    [0007]
    Perfume composition according to any one of claims 4 to 6, characterized by the fact that it exhibits olfactory characteristics of mugué.
    [0008]
    Composition for personal care or home care, characterized in that it comprises a compound of formula (I) as defined in claim 1, or a perfume composition as defined in any one of claims 3 to 7.
    [0009]
    9. A method for producing an olfactory characteristic of muugué for a perfume composition characterized in that it comprises the step of adding to said composition a compound as defined in claim 1.
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    同族专利:
    公开号 | 公开日
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    US20170204038A1|2017-07-20|
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    MX370901B|2020-01-09|
    PL2994093T3|2017-12-29|
    MX2015014967A|2016-02-05|
    JP2016523827A|2016-08-12|
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    KR102353588B1|2022-01-19|
    RU2662835C2|2018-07-31|
    AU2014264609A1|2015-11-05|
    US20160108342A1|2016-04-21|
    GB201308248D0|2013-06-12|
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    ZA201507876B|2017-09-27|
    RU2015145323A|2017-06-14|
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    CN107849488B|2015-07-14|2021-04-13|弗门尼舍有限公司|Compound with muguet odor|
    GB2546519A|2016-01-21|2017-07-26|Givaudan Sa|Improvements in or relating to organic compounds|
    WO2018087147A1|2016-11-10|2018-05-17|Givaudan Sa|Deodorizing agent comprising zinc neodecanoate|
    ES2832753T3|2017-01-18|2021-06-11|Firmenich & Cie|Composition that has the smell of thrush|
    JP2020505501A|2017-01-18|2020-02-20|フイルメニツヒ ソシエテ アノニムＦｉｒｍｅｎｉｃｈ Ｓａ|Composition having a Mugue aroma|
    WO2017174827A1|2017-08-09|2017-10-12|Symrise Ag|Use of ambrocenide ® for intensifying a lily of the valley scent|
    KR101988012B1|2017-12-12|2019-06-11|한국콜마주식회사|Composition for masking raw-material smell of cosmetic composition|
    EP3658236A1|2017-12-21|2020-06-03|Firmenich SA|Method for identifying positive allosteric modulators for odorant receptors|
    EP3533786A1|2018-03-02|2019-09-04|Givaudan SA|Thioether precursors for fragrant ketones and aldehydes|
    WO2020098923A1|2018-11-13|2020-05-22|Symrise Ag|Perfuming ingredients with lily of the valley note|
    WO2020127325A2|2018-12-19|2020-06-25|Firmenich Sa|Use of volatile compounds to modulate the perception of floral muguet|
    法律状态:
    2019-07-30| B06U| Preliminary requirement: requests with searches performed by other patent offices: procedure suspended [chapter 6.21 patent gazette]|
    2020-05-19| B09A| Decision: intention to grant [chapter 9.1 patent gazette]|
    2020-07-28| B16A| Patent or certificate of addition of invention granted [chapter 16.1 patent gazette]|Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 08/05/2014, OBSERVADAS AS CONDICOES LEGAIS. |
    优先权:
    申请号 | 申请日 | 专利标题
    GB1308248.2|2013-05-08|
    GBGB1308248.2A|GB201308248D0|2013-05-08|2013-05-08|Improvements in or relating to organic compounds|
    PCT/EP2014/059427|WO2014180945A1|2013-05-08|2014-05-08|3- propanal as perfume ingredient|
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