WO2007060048A1 - 2-methyl-3-(5-methyl-2-furyl)-butanal - Google Patents

2-methyl-3-(5-methyl-2-furyl)-butanal Download PDF

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Publication number
WO2007060048A1
WO2007060048A1 PCT/EP2006/066808 EP2006066808W WO2007060048A1 WO 2007060048 A1 WO2007060048 A1 WO 2007060048A1 EP 2006066808 W EP2006066808 W EP 2006066808W WO 2007060048 A1 WO2007060048 A1 WO 2007060048A1
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Prior art keywords
methyl
butanal
furyl
odor
oil
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PCT/EP2006/066808
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German (de)
English (en)
Inventor
Bernd Wiedwald
Axel Schöning
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Symrise Gmbh & Co. Kg
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Publication of WO2007060048A1 publication Critical patent/WO2007060048A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom

Definitions

  • the present invention relates primarily to the novel compound 2-methyl-3- (5-methyl-2-furyl) butanal and, in addition, to articles such as fragrances and flavoring compounds (fragrance and flavoring compositions) comprising a (sensory-active) amount of this substance, their respective use as odoriferous or aromatic substance (mixture) as well as processes for the preparation of 2-methyl-3- (5-methyl-2-furyl) butanal.
  • fragrances already present, the perfumery industry continues to have a general need for new fragrances that have additional positive secondary properties beyond their primary, namely, odor properties, such as e.g. a higher stability under certain conditions of use, a higher yield, a better adhesion or even better dermatological and toxicological properties compared to similar fragrances.
  • odor properties such as e.g. a higher stability under certain conditions of use, a higher yield, a better adhesion or even better dermatological and toxicological properties compared to similar fragrances.
  • fragrances with spicy or culinary odor properties that are able to produce a spicy or culinary odor note in fragrance compositions.
  • the fragrances should in particular have no negative toxicological properties.
  • this object is achieved by the compound according to the invention and its use as a fragrance and / or flavoring. Further aspects of the invention emerge from the claims and relate to corresponding methods, articles (in particular compositions) as well as production methods.
  • the invention is based inter alia on the surprising finding that the compound 2-methyl-3- (5-methyl-2-furyl) -butanal is suitable as a fragrance and flavoring.
  • the 2-methyl-3- (5-methyl-2-furyl) butanal according to the invention may be syn- or anti-configured, as (R, R) -configured enantiomer, (R 1 S) -configured enantiomer, (S. , R) -configured enantiomer, (S, S) -configured or as any mixture of the enantiomers, in particular as a racemate, or as any desired mixture of the corresponding diastereomers.
  • the structural formula of 2-methyl-3- (5-methyl-2-furyl) butanal (IUPAC name) is given below:
  • 2-methyl-3- (5-methyl-2-furyl) -butanal gives a very complex and varied odor and taste impression, which usually only from mixtures of several components (such as essential oils, or spice mixtures such as curry (powder) ) can be achieved.
  • Particularly suitable is 2-methyl-3- (5-methyl-2-furyl) butanal for imparting, modifying and / or enhancing a spicy or culinary odor or flavor.
  • 2-methyl-3- (5-methyl-2-furyl) -butanal has an extremely low sensory threshold so that it is already noticeable in very low doses and, when incorporated into a fragrance or flavoring composition, this is significant can influence (see also the comments below).
  • Table 1 shows examples of selected compounds whose olfactory properties with spicy, celery, lovage or cumin are described (Source: K. Bauer, D. Garbe and H. Surburg, Common Fragrance and Flavor Materials, 4 rd Ed, Wiley.. -VCH, Weinheim 2001, and Compendium Perfumery Ingredients Firmenich 2004 and Perfumers Compendium Symrise 2004).
  • the substance according to the invention consists of an aliphatic aldehyde with a heteroaromatic ring (furan) in the side chain.
  • the aldehyde according to the invention has a spicy, curry, celery, cumin and lovage-like odor note with additional root and ozone aspects (for example, evaluated as 3% by weight solution in ethanol or diethyl phthalate).
  • the tasting properties of the 2-methyl-3- (5-methyl-2-furyl) butanal according to the invention were as follows (evaluated in 5% by weight aqueous sugar solution or 0.5% by weight). iger aqueous saline solution):
  • the 2-methyl-3- (5-methyl-2-furyl) -butanal according to the invention is able to intensify the intensity of a fragrance mixture even at low dosages and to round off the overall appearance of the fragrance mixture to an odor, and to give the mixture more aura and naturalness to lend.
  • Another aspect of the invention relates to the use of 2-methyl-3- (5-methyl-2-furyl) -butanal or a 2-methyl-3- (5-methyl-2-furyl) -butanal comprising fragrance or flavor composition (ie, blend) (as characterized above) for imparting, modifying and / or enhancing a spicy, curry, celery, cumin, lovage, root and / or ozone odor or flavor.
  • fragrance or flavor composition ie, blend
  • a (sensory effective) amount of 2-methyl-3- (5-methyl-2 -furyl) -butanal or a 2-methyl-3- (5-methyl-2-furyl) -butanal fragrance or flavor composition (as characterized above) contacted or mixed with a product.
  • the invention also relates to perfumed or flavored articles comprising 2-methyl-3- (5-methyl-2-furyl) -butanal, e.g. In the form of a 2-methyl-3- (5-methyl-2-furyl) -butanal smelling or flavoring mixture (as characterized above).
  • 2-methyl-3- (5-methyl-2-furyl) -butanal is excellently suited for modifying and / or enhancing an odor or taste, i. that 2-methyl-3- (5-methyl-2-furyl) -butanal can function in particular as a so-called booster or enhancer.
  • 2-Methyl-3- (5-methyl-2-furyl) -butanal can be used in particular to impart more freshness, (emission) radiation, roundness and / or harmony to a fragrance or aroma composition and / or existing odor and odor /or
  • To enhance taste notes in particular the directions woody, flowery, animalistic, amber (amber), masculine, tart, and / or musk.
  • the present invention relates to the use of 2-methyl-3- (5-methyl-2-furyl) butanal for modifying and / or enhancing an odor or flavor with one, several or all of the notes woody , flowery, animal, amber (amber), masculine, herbaceous, and / or musk.
  • the present invention also relates to a method for modifying and / or enhancing an odor or flavor with one, several or all of the notes woody, flowery, animal, amber, masculine, tart, and / or musk, comprising the following step:
  • fragrances or flavorings with one, several or all of the notes woody, flowery, animal, amber, masculine, tart, and / or musk, with an amount of 2-methyl-3- (5- methyl-2-furyl) -butanal, which suffices the odor and / or taste impression of the odoriferous or aromatic substances containing one or more of the notes woody, floral, animal, amber (amber), masculine, harsh , and / or cause musk to sensory intensify.
  • Perfumed or flavored articles according to the invention include 2-methyl-3- (5-methyl-2-furyl) -butanal, preferably in the form of a fragrance or flavoring composition according to the invention.
  • fragrance or flavor compositions or perfumed articles containing an amount of 2-methyl-3- (5-methyl-2-furyl) -butanal sufficient to flavor one or more of the odor notes, curry, celery to impart, modify and / or enhance cumin ( cuminig) and / or lovage-like with additional root and / or ozone aspects.
  • a fragrance or flavoring composition according to the invention is prepared according to the invention by mixing 2-methyl-3- (5-methyl-2-furyl) -butanal with customary further constituents of a fragrance or flavoring composition, the 2-methyl-3- (5-methyl-2-furyl) -butanal in an amount sufficient to impart, modify and / or enhance an odor or flavor in the fragrance or flavoring composition.
  • the preparation of the 2-methyl-3- (5-methyl-2-furyl) -butanal according to the invention can be carried out, for example, by reacting 2-methylfuran (Sylvan) with tiglinaldehyde (2,3-dimethylacrolein).
  • the reaction is carried out in the presence of an acidic catalyst.
  • Protic acids such as sulfuric acid, sulfurous acid, salts of hydrogen sulphate such as potassium and sodium hydrogensulfate; Sulfonic acids such as p-toluenesulfonic acid, benzenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid acid, hydrochloric acid, perchloric acid, hydrobromic acid, nitric acid, phosphoric acid, salts of dihydrogen phosphate such as potassium and sodium dihydrogen phosphate.
  • Preferred acidic catalysts are sulfuric acid and the sulfonic acids, with trifluoromethanesulfonic acid and p-toluenesulfonic acid being particularly preferred.
  • acid catalysts which can be used are the organic protic acids, in particular the protic acids derived from the alkanes or aromatics, such as formic acid, acetic acid, propionic acid, butyric acid, 2-ethylhexanoic acid, benzoic acid, oxalic acid, citric acid, tartaric acid, succinic acid, malic acid, maleic acid, fumaric acid and adipic acid ,
  • the organic protic acids in particular the protic acids derived from the alkanes or aromatics, such as formic acid, acetic acid, propionic acid, butyric acid, 2-ethylhexanoic acid, benzoic acid, oxalic acid, citric acid, tartaric acid, succinic acid, malic acid, maleic acid, fumaric acid and adipic acid ,
  • Lewis acids are, for example, ZnC ⁇ , TiCl 4, AlCl 3, or FeCl.
  • acidic catalysts which are present in the solid state of matter, with acidic fixed bed catalysts being particularly advantageous to this extent.
  • acidic cation exchangers as acidic fixed bed catalysts.
  • the group of acidic cation exchangers includes, in particular, cation exchangers based on polymerization resins with different crosslinking, macroporous structure and active groups of different acidity.
  • weak to strong acidic ion exchanger based on synthetic resin in particular Lewatite ® (Bayer) and amber lite ® (Rohm and Haas) may be mentioned.
  • montmorillonites such as.
  • the K catalysts name of the company Südchemie for specially acid-treated montmorillonite.
  • usable acidic fixed bed catalysts are, for. B. loaded with mineral acids support materials (such as silica gel).
  • 2-Methyl-3- (5-methyl-2-furyl) -butanal is excellently suitable for use in fragrance and flavor compositions because of its olfactory properties.
  • the compound can be used as (i) single substance or (ii) combined with a variety of other fragrances or flavorings in numerous products. Particularly advantageous is the connection with other fragrances or aroma Combine substances in different, different proportions to novel fragrance or flavor compositions.
  • Extracts from natural raw materials such as essential oils, concretes, absolues, resines, resinoids, balms, tinctures such.
  • ambergris tincture Amyrisöl; Angelica seed oil; Angelica root oil; anise oil; Valerian oil; Basil oil; Tree Moss -Absolue; Bay oil; Mugwort oil; Benzoeresin; Bergamot oil; Beeswax absolute; birch tar; Bitter almond oil; Savory oil; Bucco blotter oil; Cabreuvaöl; cade oil; calamus; camphor oil; Cananga oil; cardamom; Cascarillaöl; cassia; Cassie absolute; Beaver-absolue; Cedern diligentöl; cedarwood; cistus; citronella; lemon; copaiba balsam; Copaivabalsamöl; Coriander oil; costus root; Cuminöl; Cypress oil; Davanaöl; Dill herb oil; Dill seed oil; Eau de Brouts absolute; Oak moss absolute; elemi; Tarragon oil; Eucalyptus citriodora oil; eucalyp
  • sandalwood Celery seed oil; spike lavender oil; star anise; Styraxöl; tagetes;
  • vetiver Juniper berry oil
  • Wine yeast oil Wormwood oil
  • Wintergreen oil ylang oil
  • hyssop oil Civet absolute; cinnamon leaf; Cinnamon bark oil and fractions thereof, or ingredients isolated therefrom;
  • fragrances from the group of hydrocarbons such as 3-carene; ⁇ -pinene; beta-pinene; ⁇ -terpinene; ⁇ -terpinene; p-cymene; bisabolene; camphene; Caryophyllene; cedrene; farnesene; limonene; longifolene; myrcene; ocimene; valencene; (E 1 Z) -1, 3, 5-undecatriene; styrene; diphenylmethane;
  • the aliphatic alcohols such as e.g. hexanol; octanol; 3-octanol; 2,6-dimethylheptanol; 2-methyl-2-heptanol; 2-methyl-2-octanol; (E) -2-hexenol; (E) - and (Z) -3-hexenol; 1-octen-3-ol; Mixture of 3,4,5,6,6-pentamethyl-3/4-hepten-2-ol and 3,5,6,6-tetramethyl-4-methyleneheptan-2-ol; (E, Z) -2,6-nonadienol; 3,7-dimethyl-7-methoxyoctane-2-ol; 9-decenol; 10-undecenol; 4-methyl-3-decen-5-ol;
  • the aliphatic aldehydes and their acetals such as hexanal; heptanal; Octanal; nonanal; decanal; undecanal; dodecanal; tridecanal; 2-methyloctanal; 2-methylnonanal; (E) -2-hexenal; (Z) -4-heptenal; 2,6-dimethyl-5-heptenal; 10- undecenal; (E) -4-decenal; 2-dodecenal; 2,6,10-trimethyl-9-undecenal; 2,6,10-trimethyl-5,9-undecadienal; Heptanaldiethylacetal; 1,1-dimethoxy-2,2,5-trimethyl-4-hexene; citronellyloxyacetaldehyde; 1 - (1-methoxy-propoxy) - (E / Z) -3-hexene; the aliphatic ketones and their oximes such as 2-heptanone;
  • the aliphatic sulfur-containing compounds e.g. 3-methylthio-hexanol; 3-Methylthiohexylacetat; 3-mercaptohexanol; 3-mercaptohexyl acetate; 3-mercaptohexyl butyrate; 3-acetylthiohexyl acetate; 1-Menthene-8-thiol;
  • aliphatic nitriles e.g. 2-nonenoic acid nitrile; 2-Undecen Textrenitril; 2-tridecenoic acid nitrile; 3,12-Tridecadien Aciditril; 3,7-dimethyl-2,6-octadienitrile; 3,7-dimethyl-6-octen Aciditril;
  • ester of aliphatic carboxylic acids e.g. (E) - and (Z) -3-hexenylformate
  • ethylacetoacetate isoamyl; hexyl acetate; 3,5,5-trimethylhexyl acetate; 3-methyl-2-butenyl acetate; (E) -2-hexenyl acetate; (E) - and (Z) -3-hexenylacetate; Octyl acetate; 3-octyl acetate; 1-octen-3-yl acetate; ethyl butyrate; Butyl butyrate, Isoamylbutyrate; hexyl butyrate; (E) - and (Z) -3-hexenyl isobutyrate; hexyl crotonate; Ethyl isovalerate; Ethyl 2-methylpentanoate; ethylhexanoate; allyl hexanoate; ethyl heptanoate;
  • Citronellol Citronellol; geraniol; nerol; linalool; Lavadulol; nerolidol; farnesol; tetrahydrolinalool; tetrahydrogeraniol; 2,6-dimethyl-7-octene-2-ol; 2,6-dimethyl octane-2-ol; 2-methyl-6-methylene-7-octen-2-ol; 2,6-dimethyl-5,7-octadiene-2-ol; 2,6-dimethyl-3,5-octadiene-2-ol; 3,7-dimethyl-4,6-octadien-3-ol; 3,7-dimethyl-1, 5,7-octatrien-3-ol 2,6-dimethyl-2,5,7-octatrien-1-ol; as well as their formates, acetates, propionates, isobutyrates, butyrate
  • cyclic alcohols e.g. 4-tert-butylcyclohexanol; 3,3,5-trimethylcyclohexanol; 3-lsocamphylcyclohexanol; 2,6,9-trimethyl-Z2, Z5, E9-cyclododecatrien-1-ol; 2-isobutyl-4-methyl tetrahydro-2H-pyran-4-ol;
  • cycloaliphatic alcohols e.g. alpha, 3,3-trimethylcyclohexylmethanol; 1- (4-isopropylcyclohexyl) ethanol; 2-methyl-4- (2,2,3-trimethyl-3-cyclopent-1-yl) butanol; 2-methyl-4- (2,2,3-trimethyl-3-cyclopent-1-yl) -2-butene-1-ol; 2-ethyl-4- (2,2,3-trimethyl-3-cyclopent-1-yl) -2-butene-1-ol; 3-methyl-5-
  • Trimethylcyclohexyl) hexan-3-ol Trimethylcyclohexyl) hexan-3-ol; the cyclic and cycloaliphatic ethers such as cineole; cedryl methyl ether; Cyclododecyl methyl ether; 1, 1-dimethoxycyclododecane; (Ethoxymethoxy) cyclododecane; alpha-Cedrenepoxid; 3a, 6, 6, 9a
  • cyclic and macrocyclic ketones such as e.g. 4-tert.-butylcyclohexanone; 2,2,5-trimethyl-5-pentylcyclopentanone; 2-heptylcyclopentanone; 2
  • pentylcyclopentanone 2-hydroxy-3-methyl-2-cyclopenten-1-one; 3-methyl-cis-2-penten-1-yl-2-cyclopenten-1-one; 3-methyl-2-pentyl-2-cyclopenten-1-one; 3-methyl-4-cyclopentadecenone; 3-methyl-5-cyclopentadecenone; 3
  • methylcyclopentadecanone 4- (1-ethoxyvinyl) -3,3,5,5-tetramethylcyclohexanone; 4-tert-pentylcyclohexanone; 5-cyclohexadecen-1-one; 6,7-dihydro-1,1,3,3,3-pentamethyl-4 (5H) -indanone; 8-cyclohexadecen-1-one; 9-cycloheptadecen-1-one; cyclopentadecanone; cyclohexadecanone;
  • cycloaliphatic aldehydes e.g. 2,4-dimethyl-3-cyclohexene carbaldehyde; 2-methyl-4- (2,2,6-trimethyl-cyclohexene-1-yl) -2-butenal; 4- (4-hydroxy-4-methylpentyl) -3-cyclohexene carbaldehyde; 4- (4-methyl-3-penten-1-yl) -3-cyclohexene carbaldehyde;
  • cycloaliphatic ketones such as B. 1 - (3,3-dimethylcyclohexyl) -4-penten-1-one; 2,2-dimethyl-1- (2,4-dimethyl-3-cyclohexen-1-yl) -1-propanone; 1 - (5,5-dimethyl-1-cyclohexen-1-yl) -4-penten-1-one; 2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydro-2-naphthalenyl methyl ketone; Methyl ⁇ . ⁇ .iO-trimethyl ⁇ . ⁇ . ⁇ -cyclododecatrienylketon; tert-butyl (2,4-dimethyl-3-cyclohexen-1-yl) ketone;
  • ester of cyclic alcohols e.g. 2-tert-butylcyclohexyl acetate; 4-tert-butylcyclohexyl acetate; 2-tert-pentylcyclohexyl acetate; 4-tert-
  • ester of cycloaliphatic alcohols such as I-cyclohexylethyl crotonate
  • esters of cycloaliphatic carboxylic acids such as.
  • allyl-3-cyclohexylpropionate Allylcyclohexyloxyacetat; cis and trans methyldihydrojasmonate; egg and trans methyl jasmonate;
  • Methyl ⁇ -hexyl-S-oxocyclopentanecarboxylate Ethyl 2-ethyl-6,6-dimethyl-2-cyclohexene carboxylate; Ethyl 2,3,6,6-tetramethyl-2-cyclohexene carboxylate; Ethyl 2-methyl-1,3-dioxolane-2-acetate;
  • the araliphatic alcohols such as e.g. benzyl alcohol; 1-phenylethyl; 2-phenylethyl alcohol; 3-phenylpropanol; 2-phenylpropanol; 2-phenoxyethanol; 2,2-dimethyl-3-phenylpropanol; 2,2-dimethyl-3- (3-methylphenyl) propanol; 1, 1 - dimethyl-2-phenylethyl alcohol; 1, 1-dimethyl-3-phenylpropanol; 1-ethyl-1-methyl-3-phenylpropanol; 2-methyl-5-phenylpentanol; 3-methyl-5-phenylpentanol; 3-phenyl-2-propene-1-ol; 4-methoxybenzyl; 1 - (4-isopropylphenyl) ethanol;
  • ester of araliphatic alcohols and aliphatic carboxylic acids e.g. benzyl acetate; benzylpropionate; benzyl isobutyrate; Benzylisovalerianat; 2-phenylethyl acetate; 2-phenylethyl propionate; 2-Phenylethylisobutyrat; 2-phenylethyl isovalerate; 1-phenylethyl acetate; alpha-Trichlormethylbenzylacetat; alpha, alpha-dimethylphenylethyl acetate; alpha, alpha-dimethylphenylethyl butyrate; cinnamyl; 2-phenoxyethyl isobutyrate; 4-methoxybenzyl acetate;
  • the araliphatic ethers such as 2-phenylethyl methyl ether; 2-phenylethyl isoamyl ether; 2-phenylethyl-1-ethoxyethyl ether; Phenylacetaldehyde dimethylacetal; phenylacetaldehyde; Hydratropaldehyde dimethylacetal; Phenylacetaldehydglycerinacetal; 2,4,6-trimethyl-4-phenyl-1,3-dioxane; 4,4a, 5,9b-tetrahydroindeno [1,2-d] -m-dioxin; 4,4a, 5,9b-tetrahydro-2,4-dimethyl-indeno [1,2-d] -m-dioxin; the aromatic and araliphatic aldehydes such.
  • aromatic and araliphatic ketones such as e.g. acetophenone; 4-methylacetophenone; 4-methoxyacetophenone; 4-tert-butyl-2,6-dimethylacetophenone; 4-phenyl-2-butanone; 4- (4-hydroxyphenyl) -2-butanone; 1 - (2-naphthalenyl) ethanone; 2-benzofuranylethanone; (3-methyl-2-benzofuranyl) ethanone; benzophenone; 1, 1, 2,3,3,6-hexamethyl-5-indanyl methyl ketone; 6-tert-butyl-1, 1-dimethyl-4-indanyl methyl ketone; 1- [2,3-dihydro-1, 1, 2,6-tetramethyl-3- (1-methylethyl) -1H-5-indenyl] ethanone; 5 ', 6', 7 ', 8'-tetrahydro-3', 5 ', 5', 6 ',
  • aromatic and araliphatic carboxylic acids and their esters e.g. benzoic acid; phenylacetic acid; methylbenzoate; ethyl benzoate; hexyl benzoate; Benzyl benzoate; methyl phenylacetate; ethyl phenylacetate; geranyl phenylacetate; Phenylethyl phenylacetate; Methylcinnmat; ethylcinnamate; Benzyl; Phenylethyl cinnamate; cinnamyl cinnamate; allyl phenoxyacetate; methyl salicylate; Isoamylsalicylate; hexyl salicylate; cyclohexyl; Cis-3-hexenyl salicylate; Benzyl salicylate; phenylethyl; Methyl-2,4-dihydroxy-3,6-dimethylbenzoate; Ethyl
  • the nitrogen-containing aromatic compounds such as 2,4,6-trinitro-1,3-dimethyl-5-tert-butylbenzene; 3,5-dinitro-2,6-dimethyl-4-tert.-butylacetophenone; cinnamic acid; 3-methyl-5-phenyl-2-penten Aciditril; 3-methyl-5- phenylpentanklarenitril; methyl anthranilate; Methyl N-methylanthranilate;
  • the phenols, phenyl ethers and phenyl esters e.g. estragole; anethole; eugenol; Eugenylmethylether; isoeugenol; Isoeugenylmethylether; thymol; carvacrol; diphenyl ether; beta-naphthyl methyl ether; beta-Naphthylethylether; beta-naphthyl isobutyl ether; 1, 4-dimethoxybenzene; Eugenylacetat; 2-methoxy-4-methylphenol; 2-ethoxy-5- (1-propenyl) phenol; p-Kresylphenylacetat;
  • heterocyclic compounds such as e.g. 2,5-dimethyl-4-hydroxy-2H-furan-3-one; 2-ethyl-4-hydroxy-5-methyl-2H-furan-3-one; 3-hydroxy-2-methyl-4H-pyran-4-one; 2-ethyl-3-hydroxy-4H-pyran-4-one;
  • the lactones e.g. 1,4-octanolide; 3-methyl-1,4-octanolide; 1,4-nonanolide; 1, 4-decanolide; 8-decene-1,4-olide; 1,4-undecanolide; 1,4-dodecanolide; 1, 5-decanolide; 1, 5-dodecanolide; 4-methyl-1,4-decanolide; 1,15-pentadecanolide; cis and trans-11-pentadecene-1, 15-olide; cis- and trans-12-pentadecene-1, 15-olide; 1, 16-hexadecanolide; 9-hexadecene-1, 16-olide; 10-oxa-1, 16-hexadecanolide; 1 1 -Oxa-1, 16-hexadecanolide; 12-oxa-1,16-hexadecanolide; Ethylene-1,12-dodecanedi
  • the amount of the aldehyde of the present invention is preferably 0.00001 to 90% by weight, preferably 0.001 to 70% by weight, and more preferably 0.01 to 50% by weight, based on the total amount of the olfactory fragrance or flavoring composition.
  • 2-methyl-3- (5-methyl-2-furyl) -butanal is mainly used to impart more freshness, (off) radiation, roundness and / or harmony to a fragrance or flavoring composition, and / or to enhance certain notes, especially notes of the directions woody, flowery, animal, amber (amber), masculine, tart, and / or musk
  • the proportion of the aldehyde according to the invention is preferably quite low and preferably in the range of 0.001 to 1 wt .-%, preferably in the range of 0.01 to 0.5 wt .-%, based on the total amount of the fragrance or flavor composition. If a comparatively low concentration is selected within the preferred concentration ranges, depending on the other components of the particular composition, in some cases the mediation of the abovementioned odor or taste notes does not yet occur.
  • Fragrance or flavor compositions containing 2-methyl-3- (5-methyl-2-furyl) -butanal can be used in liquid form, neat or diluted with a solvent for perfuming or flavoring.
  • Suitable solvents for this are e.g. Ethanol, isopropanol, diethylene glycol monoethyl ether, glycerol, propylene glycol, 1,2-butylene glycol, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate, triacetin, etc.
  • odoriferous or flavoring compositions according to the invention which contain 2-methyl-3- (5-methyl-2-furyl) -butanal may be adsorbed on a carrier which promotes both a fine distribution of the odoriferous or aromatic substances in the product as well as providing a controlled release during use.
  • a carrier which promotes both a fine distribution of the odoriferous or aromatic substances in the product as well as providing a controlled release during use.
  • Such carriers can porous inorganic materials such as light sulfate, silica gels, zeolites, gypsum, clays, clay granules, gas concrete, etc. or organic materials such as woods, cellulose-based substances, sugars, dextrins (eg, matodextrin) or plastics such as PVC, polyvinyl acetates or polyurethanes be.
  • the combination of composition according to the invention and carrier represents an exemplary article according to the invention.
  • Fragrance or flavor compositions containing 2-methyl-3- (5-methyl-2-furyl) butanal may also be microencapsulated, spray dried, as inclusion complexes, or as extrusion products (ie, inventive articles) and in this form z. B. to be perfumed or flavored product.
  • the properties of the compositions modified in this way can be further optimized by so-called “coating" with suitable materials with a view to a more targeted release of fragrance, for which purpose waxy plastics such as polyvinyl alcohol are preferably used.
  • the microencapsulation of the odoriferous or flavoring compositions according to the invention to give articles according to the invention can be carried out, for example, by the so-called coacervation method with the aid of capsule materials, e.g. made of polyurethane-like substances or soft gelatin.
  • the spray-dried fragrance or flavoring compositions can be prepared, for example, by spray-drying an emulsion or dispersion containing the fragrance or aroma composition, it being possible to use modified starches, proteins, dextrin and vegetable gums as carriers.
  • Inclusion complexes can e.g. by incorporating dispersions of the fragrance or flavoring composition and cyclodextrins or urea derivatives into a suitable solvent, e.g. Water, to be produced.
  • Extrusion products may be made by fusing the fragrance or flavor compositions together with a suitable waxy substance and by extrusion followed by solidification, optionally in a suitable solvent, e.g. Isopropanol.
  • 2-Methyl-3- (5-methyl-2-furyl) -butanal and fragrance compositions containing 2-methyl-3- (5-methyl-2-furyl) butanal can be used in concentrated form, in solutions or modified form described above are used for the production of perfumed articles according to the invention such as perfume extracts, Eau de perfumes, Eau de Toilettes, shaving waters, Eau de Colognes, pre-shave products, splash colognes and perfumed Tissue towels and the perfuming of acidic, alkaline and neutral detergents, such as floor cleaners, window glass cleaners, dishwashing detergents, bathroom and sanitary cleaners, scouring cream, solid and liquid toilet cleaners, powder and foam carpet cleaners, textile fresheners, ironing aids, liquid detergents, powdered detergents, laundry pretreatment agents such Bleaching agents, soaking and stain removers, fabric softeners, laundry soaps, washing tablets, disinfectants, surface disinfectants and air fresheners in liquid, gel or solid support, aerosol sprays, waxes and
  • the 2-methyl-3- (5-methyl-2-furyl) -butanal according to the invention can be incorporated into flavored or flavored articles, in particular for nutrition, oral care or pleasure-use preparations.
  • the diet or pleasure-serving preparations are, for example, baked goods (eg bread, dry biscuits, cakes, other pastry), confectionery (eg chocolates, chocolate bar products, other bar products, fruit gums, hard and soft caramels, chewing gum), alcoholic or non-alcoholic beverages (eg Coffee, tea, wine, wine-based beverages, beer, beer-based beverages, liqueurs, brandies, brandies, fruit-based sodas, isotonic drinks, soft drinks, nectars, fruit and vegetable juices, fruit or vegetable juice preparations), instant drinks (eg instant cocoa drinks, Instant tea drinks, instant coffee drinks), meat products (eg ham, fresh sausage or raw sausage preparations, seasoned or marinated fresh or salted meat products), eggs or egg products (dry egg, egg white, egg yolks), cereal products (eg breakfast cereals, muesli bars, pre-cooked finished rice products), dairy products (eg milk drinks, milk ice cream, yoghurt, kefir, cream cheese, soft cheese - hard cheese, dried milk powder, whey,
  • Formulations according to the invention can be applied, for example, to B. present as a semi-finished product or as seasoning mixture.
  • compositions according to the invention can serve, in particular, as semi-finished goods for the production of further preparations for nutrition or enjoyment, in particular in spray-dried form.
  • Compositions according to the invention may also be in the form of capsules, tablets (non-coated and coated tablets, eg enteric coatings), dragees, granules, pellets, solid mixtures, dispersions in liquid phases, as emulsions, as powders, as solutions, as pastes or as other swallowing agents. or chewable preparations as a dietary supplement.
  • Oral preparations according to the invention are, in particular, oral and / or dental care products such as toothpastes, tooth gels, tooth powders, mouthwashes, chewing gums and other oral hygiene products.
  • customary active substances, basic substances, auxiliaries and additives for nutrition, oral care or pleasure-use preparations according to the invention can be used in amounts of 5 to 99.999999% by weight, preferably 10 to 80% by weight, based on the Total weight of the preparation to be included.
  • the preparations may comprise water in an amount of up to 99.999999% by weight, preferably 5 to 80% by weight, based on the total weight of the preparation.
  • preparations according to the invention (as examples of articles according to the invention) containing 2-methyl-3- (5-methyl-2-furyl) -butanal are prepared according to a preferred embodiment in which the 2-methyl-3- (5-methyl-2-furyl) - butanal as a substance, as a solution (eg in ethanol, water or 1, 2-propylene glycol) or in the form of a mixture with a solid or liquid carrier (eg maltodextrin, starch, silica gel), other flavors or flavorings and optionally other Auxiliaries and / or stabilizers (eg natural or artificial polysaccharides and / or vegetable gums such as modified starches or gum arabic) are incorporated into a dietary, oral care or pleasure serving base preparation.
  • preparations according to the invention present as solution and / or suspension or emulsion can also be converted by spray-drying into a solid preparation according to the invention (semi-finished product).
  • the spray-dried solid preparations according to the invention are particularly suitable as semi-finished goods for the production of further preparations according to the invention.
  • the spray-dried solid preparations according to the invention preferably contain 50 to 95% by weight of excipients, in particular maltodextrin and / or starch, 5 to 40% adjuvants, preferably natural or artificial polysaccharides and / or vegetable gums such as modified starches or gum arabic.
  • the inventive 2-methyl-3- (5-methyl-2-furyl) butanal and optionally other constituents of the preparation according to the invention are initially prepared in emulsions, in liposomes, for example starting from phosphatidylcholine, in microspheres for the preparation of preparations according to the invention , in nanospheres or else in capsules, granules or extrudates of a matrix suitable for foods and semi-luxuries, for example starch, starch derivatives (eg modified starch), cellulose or cellulose derivatives (eg hydroxypropylcellulose), other polysaccharides (eg dextrin, alginate, curdlan, Carafeenan, chitin, chitosan, pullulan), natural fats, natural waxes (eg beeswax, carnauba wax), from proteins, eg gelatin or other natural products (eg shellac) incorporated.
  • starch starch derivatives (eg modified starch)
  • the products can be obtained by spray drying, spray granulation, melt granulation, coacervation, coagulation, extrusion, melt extrusion, emulsion methods, coating or other suitable encapsulation methods and optionally a suitable combination of the abovementioned methods.
  • the 2-methyl-3- (5-methyl-2-furyl) -butanal is initially mixed with one or more suitable complexing agents, for example with cyclodextrins or cyclodextrin derivatives, preferably ⁇ - or ⁇ - Cyclodextrin, complexed and used in this complexed form.
  • a preparation according to the invention wherein the matrix is selected so that 2-methyl-3- (5-methyl-2-furyl) -butanal delayed released from the matrix, so that a long-lasting effect is achieved.
  • the matrix is selected so that 2-methyl-3- (5-methyl-2-furyl) -butanal delayed released from the matrix, so that a long-lasting effect is achieved.
  • a fat, wax, polysaccharide or protein matrix is particularly preferred.
  • auxiliaries and additives for food or beverages for example water, mixtures of fresh or processed, vegetable or animal raw materials or raw materials (eg crude , roasted, dried, fermented, smoked and / or cooked Meat, bone, cartilage, fish, vegetables, fruits, herbs, nuts, vegetables or fruit juices or pastes or mixtures thereof), digestible or non-digestible carbohydrates (eg sucrose, maltose, fructose, glucose, dextrins, amylose, amylopectin, inulin, xylans , Cellulose, tagatose), sugar alcohols (eg sorbitol, erythritol), natural or hydrogenated fats (eg tallow, lard, palm fat, coconut fat, hardened vegetable fat), oils (eg sunflower oil, peanut oil, corn oil, olive oil, fish oil, soybean oil, sesame oil ), Fatty acids or
  • Dental care preparations preparations based on oral care
  • 2-methyl-3- (5-methyl-2-furyl) butanal generally comprise an abrasive system (grinding or polishing agent), such as, for example, silica gel.
  • ren calcium carbonates, calcium phosphates, aluminum oxides and / or hydroxy lapatites, surface-active substances such as sodium lauryl sulfate, sodium lauryl sarcosinate and / or cocamidopropyl betaine, humectants such as glycerol and / or sorbitol, thickeners such as carboxymethyl cellulose, polyethylene glycols, carrageenan and / or Laponite ®, sweeteners such as saccharin, flavor for unpleasant taste impressions, flavor for more, not unpleasant usually taste impressions, flavor-modulating substances (eg inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate or other substances such as sodium glutamate or 2-phenoxypropionic) Cooling agents such as menthol, menthane derivatives (eg L-menthol, L-menthyl lactate, L-Menthylalkylcarbonate, menthone
  • Chewing gums (as another example of oral care preparations) containing the 2-methyl-3- (5-methyl-2-furyl) butanal according to the invention generally comprise a chewing gum base, ie chewing gum that becomes plastic upon chewing, sugars of various types Types, sugar substitutes, other sweet-tasting substances, sugar alcohols, flavoring agents for unpleasant taste impressions, other flavor modulators for further, generally not unpleasant taste impressions, taste modulating substances (eg inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate or other substances such as sodium glutamate or 2-phenoxypropionic acid), Humectants, thickeners, emulsifiers, aromatics and stabilizers or odorants.
  • the preparations according to the invention may preferably also contain an aroma composition in addition to the compound according to the invention in order to round off and refine the taste and / or smell of the preparation.
  • Suitable (additional) aroma compositions contain, for example, synthetic, natural or nature-identical flavorings, fragrances and flavorings as well as suitable excipients and carriers.
  • this perfume composition becomes fresher, brighter, more rounded by the addition of 0.4% by weight of a 10% strength by weight ethanolic solution of 2-methyl-3- (5-methyl-2-furyl) -butanal , and more harmonious, adding a spicy note and enhancing woody and floral aspects, making the perfume composition more masculine overall.
  • 2-Methyl-3- (5-methyl-2-furyl) -butanal fits well into the composition. It gives the composition its own character through its own odor as well as through its modifying and intensifying effect (booster effect) and combines flowery, woody and spicy elements.
  • Example 2 The perfume oil composition from Example 2 (after addition of the aldehyde according to the invention) was incorporated in a dosage of 0.5% by weight into a shampoo base of the following composition:
  • Citric acid 1 3%
  • the pH of the shampoo base was about 6. From this, 100 ml of a 20% by weight aqueous shampoo solution were prepared. In this shampoo solution, 2 hair slides were washed together for 2 minutes and then rinsed for 20 seconds under running lukewarm water. One strand of hair was wet wrapped in aluminum foil and dried the second strand of hair with a hair dryer. Both strands of hair were judged by a panel odor. Both strands of hair showed a fresh, woody and spicy, overall masculine, scent with floral aspects, whereby the overall impression was radiant, rounded and harmonious.
  • Example 2 The perfume oil composition from Example 2 (after addition of the aldehyde according to the invention) was incorporated in a dosage of 0.5% by weight into a fabric softener base of the following composition:
  • the pH of the fabric softener base was in the range 2 - 3.
  • Two pieces of fabric were rinsed with 370 g of a 1% aqueous fabric softener solution in a Linetest machine in the softening program for 30 minutes at 20 ° C. The cloths were wrung out and then thrown for 20 seconds. A rag was wet-sealed, and one hung up to dry. Subsequently, both flaps were assessed by a panel odor. Both lobes showed a fresh, woody and spicy, overall masculine, scent with floral aspects, the overall impression was radiant, rounded and harmonious.
  • Example 2 The perfume oil composition from Example 2 (after addition of the aldehyde according to the invention) was incorporated in a dosage of 0.4% by weight into a washing powder base of the following formulation:
  • Example 6a Allium Curry Aroma Composition
  • the aroma composition (mixture A1) thus obtained had more complex notes, in particular interesting spicy curry, celery and lovage notes.
  • the leek curry flavor composition (Blend A1) was added to the creamy leek soup base formulation at a level of 1 to 15 weight percent, preferably at a dosage of 3 to 10 weight percent, based on the mass of the creamy soup soup base formulation.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Fats And Perfumes (AREA)

Abstract

L’invention concerne l’utilisation d’un nouveau composé, le 2-méthyl-3-(5-méthyl-2-furyl)-butanal, en tant que substance aromatique et/ou olfactive.
PCT/EP2006/066808 2005-11-26 2006-09-27 2-methyl-3-(5-methyl-2-furyl)-butanal WO2007060048A1 (fr)

Applications Claiming Priority (2)

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DE102005056453.4 2005-11-26
DE102005056453A DE102005056453A1 (de) 2005-11-26 2005-11-26 2-Methyl-3-(5-methyl-2-furyl)-butanal

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WO2007060048A1 true WO2007060048A1 (fr) 2007-05-31

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Publication number Priority date Publication date Assignee Title
US9717815B2 (en) 2014-07-30 2017-08-01 Georgia-Pacific Consumer Products Lp Air freshener dispensers, cartridges therefor, systems, and methods
US11332693B2 (en) 2015-12-11 2022-05-17 Givaudan Sa Organic compounds

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
NOWICKI J ET AL: "SYNTHESIS OF NEW FRAGRANCES FROM 2-METHYLFURAN. PART II", JOURNAL OF COSMETIC SCIENCE, SOCIETY OF COSMETIC CHEMISTS, NEW YORK, NY,, US, vol. 50, no. 2, March 1999 (1999-03-01), pages 99 - 104, XP009055348, ISSN: 1525-7886 *
NOWICKI J, GORA J: "SYNTHESIS OF NEW FRAGRANCES FROM 2-METHYLFURAN. PART I", JOURNAL OF COSMETIC SCIENCE, SOCIETY OF COSMETIC CHEMISTS, NEW YORK, NY, US, vol. 50, no. 2, March 1999 (1999-03-01), pages 91 - 98, XP009075747 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9717815B2 (en) 2014-07-30 2017-08-01 Georgia-Pacific Consumer Products Lp Air freshener dispensers, cartridges therefor, systems, and methods
US10391193B2 (en) 2014-07-30 2019-08-27 Gpcp Ip Holdings Llc Air freshener dispensers, cartridges therefor, systems, and methods
US11332693B2 (en) 2015-12-11 2022-05-17 Givaudan Sa Organic compounds

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