US20190276386A1 - Homovanillic ester, more particularly for achieving an impression of heat and/or spiciness - Google Patents

Homovanillic ester, more particularly for achieving an impression of heat and/or spiciness Download PDF

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US20190276386A1
US20190276386A1 US16/345,921 US201516345921A US2019276386A1 US 20190276386 A1 US20190276386 A1 US 20190276386A1 US 201516345921 A US201516345921 A US 201516345921A US 2019276386 A1 US2019276386 A1 US 2019276386A1
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residue
hydroxy
acetate
methoxyphenyl
formula
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Michael Backes
Jakob Peter Ley
Andreas Degenhardt
Susanne Paetz
Katharina Reichelt
Thomas Riess
Bettina KLOSE
Fabia HENTSCHEL
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/734—Ethers
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
    • A23B4/00—Preservation of meat, sausages, fish or fish products
    • A23B4/06—Freezing; Subsequent thawing; Cooling
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/204—Aromatic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/205—Heterocyclic compounds
    • A23L27/2052—Heterocyclic compounds having oxygen or sulfur as the only hetero atoms
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/84—Flavour masking or reducing agents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/88—Taste or flavour enhancing agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
    • C07C69/708—Ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C69/757—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2200/00—Function of food ingredients
    • A23V2200/15—Flavour affecting agent
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2200/00—Function of food ingredients
    • A23V2200/16—Taste affecting agent
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Definitions

  • the present invention particularly relates to novel uses of compounds of formula (I) (as described herein), partly also of novel compounds of formula (I) as such, aroma compositions containing compounds of formula (I), new preparations as well as new methods using compounds of formula (I). Further aspects of the present invention arise from the patent claims and the following description including examples.
  • Capsaicin [N-(4-hydroxy-3-methoxybenzyl)-8-methyl-(6E)-nonenoic acid amide] and other capsaicinoids such as nonivamide ([N-(4-hydroxy-3-methoxybenzyl)-nonanoic acid amide) have been known for a long time as pungent and spicy flavours from different Capsicum species, in particular, chili pepper.
  • nonivamide [N-(4-hydroxy-3-methoxybenzyl)-nonanoic acid amide)
  • chili pepper At an appropriately low dosage of capsaicinoids, a neutral pungency and a warm sensation is perceived in the mouth, wherein the threshold for pain-inducing pungency and hot sensation is exceeded very quickly.
  • capsaicin in food is not allowed in the European Union (was deleted from the Community Flavouring List in 2004), since evaluation of the genotoxic potential of the compound yielded a negative result (European Food Safety Authority (EFSA), P., Italy, Opinion of the Scientific Committee on Food on Capsaicin. European Commission 2002, (SDF/CS/FLAV/FLAVOUR/8 ADD1 Final).
  • EFSA European Food Safety Authority
  • SDF/CS/FLAV/FLAVOUR/8 ADD1 Final European Commission 2002
  • use in foods is often difficult, since capsaicin has a very low taste threshold and a high potency as a pungent substance (16,000,000 Scoville units, cf. http://en.wikipedia.org/wiki/Capsaicin; version of the record as last amended on 11 Nov. 2011, 9:02 ⁇ m).
  • capsaicin is used almost exclusively in the form of Capsicum extract, which contains residues of other flavouring substances, which taste or smell like Capsicum , besides other pungent substances and is, therefore, only limitedly suitable for broad use.
  • Capsicum extract which contains residues of other flavouring substances, which taste or smell like Capsicum , besides other pungent substances and is, therefore, only limitedly suitable for broad use.
  • piperine (1-piperoyl piperidine) that occurs in white pepper also causes a strongly pungent sensation (Römpp Lexicon Chemistry of Natural Compounds, Thieme 1997, p. 500) it has a relative pungency of only about 1% as compared to capsaicin. Furthermore, piperine has an intense taste of its own, reminiscent of pepper, so that the use in many preparations can only occur to a limited extent.
  • pungent vanilloid substances Due to the lipophilic nature of these pungent vanilloid substances, the onset of the pungent sensation often is delayed by a few seconds and also persists for a particularly long time, especially in preparations containing weakly lipophilic components (e.g. triglycerides), wherein at the same time the solubility is only insufficient.
  • weakly lipophilic components e.g. triglycerides
  • pungent substances such as gingerol-[6] from ginger or paradol-[6] from grains of paradise, both of which have a pungent taste, but have a strong aftertaste.
  • pungent-tasting substances such as the drimane, polygodial (from Kenyan pepper, Tasmannia lanceolata ) or resiniferatoxin from Euphorbia resinifera are known (Szallasi, A.; Biro, T.; Modarres, S.; Garlaschelli, L.; Petersen, M.; Klush, A.; Vidari, G.; Jonassohn, M.; De Rosa, S.; Sterner, O.; Blumberg, P.
  • the methyl ester of homovanillic acid was determined in various woods, which are used for storing wine and spirits (e.g. Fernandez de Simon, B.; Esteruelas, E.; Munoz, A. M.; Cadahia, E.; Sanz, M., J. Agric. Food Chem. 2009, 57, 3217-3227.).
  • the ethyl ester of homovanillic acid was detected in wine and spirits themselves, mostly in connection with a storage in oak barrels (e. g. Cabaroglu, T.; Canbas, A.; Baumes, R.; Bayonove, C.; Lepoutre, J. P.; G ⁇ nata, Z., J. Food Sci.
  • US 2009/0170942 A1 discloses specific ester derivatives of homovanillinic acid and various (medical) applications thereof.
  • ethanol is a small hydrophilic molecule, which causes a fast and pleasant pungent sensation that does not last very long. Since this only works at relatively high concentrations of 0.5% or more, but the consumption of ethanol causes health disorders and may also result in addiction upon prolonged consumption, flavour formulations, which can simulate the pungency profile of ethanol, without posing the disadvantages mentioned are sought after.
  • EP 1,515,943 B1 describes specific longer-chain vanillylmandelic acid alkylamides or WO 2009 065,239 describes polygodial and warburganal as pungent substances to obtain an ethanol-like pungent sensation; long-lasting pungent sensation, which is not described by the testers as sensation typical of ethanol is again observed due to the lipophilicity.
  • FIG. 1 is a chromatogram graph of the compounds from the primary reaction mixture containing ethyl homovanillate by reaction of ascorbic acid with vanillyl alcohol after 6 h at 100° C. according to aspects of the invention
  • FIG. 2 is a chromatogram graph of the primary reaction mixture divided into 12 fractions based on the UV trace at 210 nm using LCTaste® in accordance with aspects of the invention.
  • FIG. 3 is a graph of the pungency profile of butyl-2-(4-hydroxy-3-methoxyphenyl) acetate compared with nonivamide according to aspects of the invention.
  • the compounds described herein are advantageously suitable for use (in particular, as described above) in a pharmaceutical preparation, a preparation serving nutrition, oral hygiene, or pleasure, preferably wherein the total quantity of compound(s) of formula (I) and/or salt(s) thereof in the preparation is sufficient to
  • the total amount of compound(s) of the formula (I) and/or salt(s) thereof in the preparation is not sufficient to create a warming or pungent effect on the tongue or in the oral cavity, but is sufficient to mask or reduce an unpleasant taste sensation of an unpleasant tasting substance or mixture of substances.
  • Another aspect of the present invention relates to new compounds of the formula (I), salts thereof, their mixtures, namely a compound of the formula (I) or a physiologically acceptable salt thereof, wherein the phenolic hydroxy group in formula (I) is deprotonated, or a mixture comprising one or several different compounds of formula (I) and/or one or several physiologically acceptable salts thereof, wherein the phenolic hydroxy group in formula (I) is deprotonated, respectively, or consisting of a plurality of different compounds of formula (I) and/or physiologically acceptable salts thereof, wherein the phenolic hydroxy group in formula (I) is deprotonated, respectively,
  • the present invention also relates, in particular, to novel flavour compositions, namely a flavour composition,
  • compounds of formula (I) or their salts or mixtures thereof advantageously often do not have any significant other or undesired flavour effects, and thus can be used particularly well in many different types of flavours.
  • Flavour compositions which contain combinations of compounds of the formula (I) or their salts with one or several other trigeminally (pungent, warming, stinging, biting, scratching, cooling, numbing, tingling, astringent) effective substances, are particularly advantageous, wherein their trigeminal (primary) effect can be advantageously modulated by compounds of the formula (I) or their salts. For example, a warming, pungent or cooling effect can thereby be amplified, while an astringent effect can be mitigated.
  • flavour composition which additionally contains one or several substances which do not correspond to the formula (I) and have an unpleasant, in particular, bitter taste, or an astringent, bitter, dry, dusty, floury, chalky and/or metallic touch, preferably selected from the group consisting of:
  • the present invention further relates to a pharmaceutical preparation, a preparation serving nutrition, oral hygiene or pleasure, comprising
  • a preparation according to the invention preferably also comprises
  • Preferred according to the invention also is a preparation as described above, wherein the total quantity of compound(s) of the formula (I) and/or salt (s) thereof in the preparation is sufficient to
  • Preparations serving nutrition or pleasure are, e.g. bakery products (e.g. bread, dry biscuits, cakes, other pastries), sweets (e.g. chocolates, chocolate bars, other sweet bars, fruit gum, hard and soft caramels, chewing gum), alcoholic or non-alcoholic beverages (e.g. cocoa, coffee, green tea, black tea, extracts enriched with (green, black) tea, tea drinks, rooibos tea, other herbal tea, wine, wine cocktails, beer, beer cocktails, liqueurs, schnapps, brandy, fruit juices, isotonic drinks, refreshment drinks, nectars, fruit and vegetable juices, fruit or vegetable juice preparations), instant beverages (e.g.
  • bakery products e.g. bread, dry biscuits, cakes, other pastries
  • sweets e.g. chocolates, chocolate bars, other sweet bars, fruit gum, hard and soft caramels, chewing gum
  • alcoholic or non-alcoholic beverages e.g. cocoa, coffee, green tea, black tea, extracts
  • instant cocoa drinks, instant tea drinks, instant coffee drinks meat products (e.g. ham, fresh sausage or raw sausage preparations, spiced or marinated fresh or salted meat products), eggs or egg products (dry egg, egg white, egg yolk), cereal products (e.g. breakfast cereals, cereal bars, pre-cooked readymade rice products), dairy products (e.g. full-fat or fat-reduced milk or fat-free milk drinks, rice pudding, yoghurt, kefir, fresh cheese, soft cheese, hard cheese, dried milk powder, whey, butter, buttermilk, partially or completely hydrolysed lactoprotein-containing products), products from soy protein or other soybean fractions (e.g.
  • soy milk and products made from it isolated or enzymatically treated beverages, drinks containing soy protein, drinks containing soybean flour, soya-lecithin-containing preparations, fermented products such as tofu or tempe or products made from them and mixtures with fruit preparations and optional flavours), fruit preparations (e.g. jams, fruit ice-cream, fruit sauces, fruit fillings), vegetable preparations (e.g. ketchup, sauces, dried vegetables, frozen vegetables, pre-cooked vegetables, boiled vegetables), snacks (e.g. baked or fried potato crisps or potato dough products, corn or peanut-based pastes), fat and oil-based products or emulsions thereof (e.g.
  • full-fat or fat-reduced mayonnaise, remoulade, dressings mayonnaise, remoulade, dressings
  • other ready-to-serve meals and soups e.g. dry soups, instant soups, pre-cooked soups
  • spices e.g., pepperener preparations, tablets or sachets, other preparations for sweetening or whitening beverages or other foodstuffs.
  • the preparations according to the invention can also serve as semi-finished products for the preparation of further preparations serving nutrition or pleasure.
  • compositions comprise a pharmaceutical active ingredient.
  • pharmaceutical active ingredients are, for example, steroidal anti-inflammatory substances of the corticosteroid type, such as for example hydrocortisone, hydrocortisone derivatives, such as hydrocortisone 17-butyrate, dexamethasone, dexamethasone phosphate, methylprednisolone or cortisone.
  • non-steroidal pharmaceutical active ingredients are, for example, inflammatory inhibitors such as oxicams such as piroxicam or tenoxicam; salicylates such as Aspirin® (acetylsalicylic acid), disalcid, solprin or fendosal; acetic acid derivatives such as diclofenac, fenclofenac, indomethacin, sulindac, tolmetin, or clindanac; fenamates such as mefenamic, meclofenamic, flufenamic or niflumic; propionic acid derivatives such as ibuprofen, naproxen, flurbiprofen, benoxaprofen or pyrazoles, such as phenyl butazone, oxyphenyl butazone, febrazone or azapropazone.
  • inflammatory inhibitors such as oxicams such as piroxicam or tenoxicam
  • salicylates such as Aspirin® (acety
  • Particularly preferred pharmaceutical preparations are non-prescription products and OTC (over-the-counter) preparations containing active pharmaceutical ingredients such as paracetamol, acetylsalicylic acid or ibuprofen, vitamins (for example vitamin H, vitamins from the B series such as vitamin B1, B2, B6, B12, niacin, panthotenic acid, preferably in the form of (effervescent) tablets or capsules), minerals (preferably in the form of (effervescent) tablets or capsules) such as iron salts, zinc salts, selenium salts, products containing active pharmaceutical ingredients or extracts of ribwort (e.g. in cough syrup) or St. John's Wort.
  • active pharmaceutical ingredients such as paracetamol, acetylsalicylic acid or ibuprofen
  • vitamins for example vitamin H, vitamins from the B series such as vitamin B1, B2, B6, B12, niacin, panthotenic acid, preferably in the form of (effervescent) tablets or capsule
  • the preparations according to the invention which may also contain unpleasantly tasting substances or mixtures of substances (cf. hereto above), can also be in the form of capsules, tablets (uncoated as well as coated tablets, e.g. gastric juice-resistant coatings), dragees, granules, pellets, solid mixtures, dispersions in liquid phases, as emulsions, as powders, as solutions, as pastes or as other swallowable or chewable preparations as well as as a preparation with functional ingredients, as a food supplement or as balanced diets.
  • Mouth-care 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 care agents.
  • Dental care products (as the basis for mouth-care preparations) generally comprise an abrasive system (abrasive or polishing agent), such as e.g. crystalline silicas, calcium carbonates, calcium phosphates, aluminium oxides and/or hydroxylapatites, surfactants, e.g. sodium lauryl sulphate, sodium lauryl sarcosinate and/or cocamidopropyl betaine, humectants such as e.g. glycerin and/or sorbitol, thickeners such as e.g. carboxymethyl cellulose, polyethylene glycols, carrageenan and/or Laponite®, sweeteners such as e.g.
  • an abrasive system abrasive or polishing agent
  • abrasive or polishing agent such as e.g. crystalline silicas, calcium carbonates, calcium phosphates, aluminium oxides and/or hydroxylapatites
  • surfactants e.
  • taste modifiers e.g. inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate or other substances such as sodium glutamate or 2-phenoxy propionic acid
  • cooling active ingredients such as e.g. menthol, menthol derivatives (e.g. L-menthol, L-menthyl lactate, L-menthylalkyl carbonate, menthone ketals, menthane carboxamides), 2,2,2-trialkyl aceteamides (e.g.
  • 2,2-diisopropyl propionic acid methylamide 2,2-diisopropyl propionic acid methylamide
  • methylene dioxy cinnamic acid-N, N-diphenylamide methylene dioxy cinnamic acid-N-ethyl-N-phenylamide
  • methylene dioxy cinnamic acid-N-pyridyl-N-phenylamide icilin derivatives
  • stabilisers and active ingredients such as sodium fluoride, sodium monofluorophosphate, tin difluoride, quaternary ammonium fluorides, zinc citrate, zinc sulphate, tin pyrophosphate, tin dichloride, mixtures of various pyrophosphates, triclosan, cetyl pyridinium chloride, aluminium lactate, potassium citrate, potassium nitrate, potassium chloride, strontium chloride, hydrogen peroxide, flavours and/or sodium bicarbonate or o
  • Chewing gums (as a further example of mouth-care preparations) generally comprise a chewing gum base, i.e. a chewing mass that plasticises during chewing, sugars of various types, sugar substitutes, sweeteners, sugar alcohols, other taste modifiers for unpleasant tastes, taste modifiers for other, generally not unpleasant tastes, taste modifiers (e.g. inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate, or other substances such as sodium glutamate or 2-phenoxy propionic acid), the cooling active ingredients, humectants, thickeners, emulsifiers, flavours and stabilisers or odour modifiers mentioned in the previous section.
  • a chewing gum base i.e. a chewing mass that plasticises during chewing
  • taste modifiers
  • Examples of usual base materials, auxiliaries and additives for preparations according to the invention are water, mixtures of fresh or processed, plant or animal base or raw materials (e.g. raw, fried, dried, fermented, smoked and/or cooked meat, bone, cartilage, fish, vegetables, fruits, herbs, nuts, vegetable or fruit juices or pastes or mixtures thereof), digestible or indigestible carbohydrates (e.g. sucrose, maltose, fructose, glucose, dextrins, amylose, amylopectin, inulin, xylans, cellulose), sugar alcohols (e.g. sorbitol), natural or hardened fats (e.g.
  • plant or animal base or raw materials e.g. raw, fried, dried, fermented, smoked and/or cooked meat, bone, cartilage, fish, vegetables, fruits, herbs, nuts, vegetable or fruit juices or pastes or mixtures thereof
  • digestible or indigestible carbohydrates e.g. sucrose, maltose,
  • oils e.g. sunflower oil, peanut oil, corn oil, olive oil, fish oil, soybean oil, sesame oil
  • fatty acids or salts thereof e.g. potassium stearate
  • proteinogenic or non-proteinogenic amino acids and related compounds e.g. taurins
  • peptides native or processed proteins (e.g. gelatin), enzymes (e.g. peptidases), nucleic acids, nucleotides, taste modifiers other than those used according to the invention for unpleasant taste sensations (e.g.
  • taste modifiers for other, generally not unpleasant taste sensations
  • taste modifiers e.g. inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate or other substances such as sodium glutamate or 2-phenoxy propionic acid
  • emulsifiers e.g. lecithins, diacylglycerols
  • stabilisers e.g. carrageenan, alginate
  • preservatives e.g.
  • saccharin cyclamate, aspartame, neotame, stevioside, rebaudioside, acesulfame K, neohesperidine dihydrochalcone, thaumatin, superaspartame
  • mineral salts e.g. sodium chloride, potassium chloride, magnesium chloride, sodium phosphates
  • anti-enzymatic-browning agents e.g. sulphites, ascorbic acid
  • essential oils e.g. carotenoids, flavonoids, anthocyanins, chlorophyll and derivatives thereof
  • spices synthetic, natural or nature-identical flavours or fragrances as well as odour modifiers.
  • the present invention also relates to a method for producing a pharmaceutical preparation, a preparation serving nutrition, oral hygiene or pleasure, preferably a preparation according to the invention, in particular, one as described herein as being preferred, comprising the following steps:
  • preparations according to the invention are preferably prepared by incorporating an ester of homovanillic acid to be used according to the invention, as a substance, as a solution or in the form of a flavour composition into a pharmaceutical base preparation serving nutrition, oral care or pleasure.
  • preparations according to the invention being present as liquids can also be converted into a solid preparation, e.g. by spray drying.
  • flavour compositions according to the invention here: containing ethyl homovanillate (17) is described by way of example by reacting
  • This flavour preparation (primary reaction mixture) preferably contains 1,000-200,000 ppm, preferably 10,000-100,000 ppm ethyl homovanillate (17) and can be used as such or, if appropriate, further purified in admixture with other flavourings and carriers as a flavour composition.
  • flavour compositions preferably contain 100-100,000 mg/kg, preferably 250-40,000 mg/kg, particularly preferably 250-15,000 mg/kg ethyl homovanillate (17) or physiologically acceptable salts, in particular, its sodium, potassium, ammonium, calcium, magnesium or zinc salts, wherein the concentration of ethyl homovanillate (17) or mixtures of ethyl homovanillate (17) with the corresponding salts in the final food products preferably corresponds to 0.1-1,000 mg/kg, preferably 1-750 mg/kg, particularly preferably 5-500 mg/kg.
  • Ascorbic acid and vanillyl alcohol are each found in nature in foodstuffs and are permitted as food additives or flavourings; therefore, the use of isolated or naturally obtained ascorbic acid, as well as of isolated or naturally obtained vanillyl alcohol, which can also be used in the form of incompletely purified extracts or fractions is particularly advantageous.
  • Vanillyl alcohol is present, e.g. in beer (Flavor-Base, 9th Edition, Leffingwell & Associates, 2013) or the Sitka spruce ( Picea sitchensis , P. J. Kohlbrenner, C. Schuerch, Benzene-Alcohol-Soluble Extractives of Sitka Spruce, J. Org. Chem. 1961, 24(2), 166-172).
  • flavour preparations according to the invention are characterised by the fact that they can contain, in addition to ethyl homovanillate (17), at least one further substance from the following Table 1 (The same applies accordingly to the flavour preparations according to the invention described herein):
  • the primary reaction mixture can be purified by one or several of the following methods:
  • compounds of formula (I) or their salts or an aroma composition according to the invention in particular, the primary reaction mixture (as described above by way of example) or the purified flavour composition (as described above by way of example) and other components of the preparation according to the invention in the form of emulsions, in liposomes, e.g. starting from phosphatidyl choline, in microspheres, in nanospheres, or also in capsules, granules or extrudates from a matrix suitable for standard and luxury food, e.g. from starch, starch derivatives, cellulose or cellulose derivatives (e.g. hydroxypropyl cellulose), other polysaccharides (e.g.
  • the compounds of formula (I) or their salts are complexed with one or several suitable complexing agents, for example with cycloglycans, e.g. cyclofructans, cyclodextrins or cyclodextrin derivatives, preferably alpha, beta and gamma cyclodextrin, and are used in this complexed form.
  • suitable complexing agents for example with cycloglycans, e.g. cyclofructans, cyclodextrins or cyclodextrin derivatives, preferably alpha, beta and gamma cyclodextrin, and are used in this complexed form.
  • Example 1 Production of a Flavour Preparation (Primary Reaction Mixture) Containing Ethyl Homovanillate (17) by Reaction of Ascorbic Acid with Vanillyl Alcohol
  • FIG. 1 LC-MS/QTOF chromatogram of the primary reaction mixture after 6 h at 100° C.; upper chromatogram mass trace ESI positive, lower chromatogram UV-VIS totalled; the numbers represent the compounds according to Table 1 and EHV stands for ethyl homovanillate (17)).
  • the primary reaction mixture is pre-fractionated using medium-pressure liquid chromatography (MPLC) (column material: Lewatit VP OC 1064; water/ethanol 3/1; v/v). Subsequently, further separation is carried out via preparative high-pressure liquid chromatography (pHPLC) (column: Phenomenex Luna C18 5 ⁇ 150 ⁇ 21.2 mm, flow rate 30 ml/min, detection 210 nm) in the isocratic mode (63% H 2 O, 37% MeOH).
  • MPLC medium-pressure liquid chromatography
  • pHPLC preparative high-pressure liquid chromatography
  • ethyl homovanillate (17) is carried out via semi-preparative high-pressure liquid chromatography (sPHPLC) in the gradient mode (column: YMC Triart 018 5 ⁇ 250 ⁇ 10 mm; A: H 2 O; B: MeOH; 0 min 65% A, 35% B; 25 min 40% A, 60% B; 30 min 100% B; flow rate 3 ml/min; detection: 250 nm).
  • sPHPLC semi-preparative high-pressure liquid chromatography
  • the primary reaction mixture is divided into 12 fractions using LC-Taste® (according to WO 2006 111,476) in the gradient mode (Hamilton PRP-1 10 ⁇ 250 ⁇ 21.5 mm; A: H 2 O, B: EtOH; 0 min 100% A; 25 min 75% A, 25% B; 40 min 100% B; flow rate: 10 ml/min, oven temperature: 80° C.), wherein the fractions were divided based on the UV trace at 210 nm. Following the narrowing of the fractions to 0.5 ml on the B ⁇ chi Syncore at 40° C., the residue was dissolved in 10 ml water.
  • Homovanillic acid (1.5-3 g) was provided with the respective alcohol (equimolar) in toluene (100 ml), conc. sulphuric acid was added to it and heated to the boiling point at the water separator for 5 h. It was washed once with saturated aqueous NaHCO 3 solution, twice with water or alternately with saturated aqueous NaCl solution and the solvent was removed under vacuum. The product was obtained by column chromatography on silica gel with a yield of about 70%.
  • Homovanillinic acid (1.5-3 g) was stirred with the respective alcohol (100 ml) and 0.2-0.5 equivalent of sulphuric acid for 7 h at 90° C. (heating block temperature). Majority of the alcohol was removed under vacuum, saturated aqueous NaHCO 3 solution and EtOAc were added, the organic phase separated and the aqueous phase extracted once with EtOAc. The combined organic phases were washed once with saturated aqueous NaHCO 3 solution and with water or alternately with saturated aqueous NaCl solution, dried over NaSO 4 and the solvent was removed under vacuum. The product was obtained by column chromatography on silica gel with a 90% to quantitative yield.
  • esters of homovanillic acid can also be obtained by transesterification, as shown by way of example on substance 2:
  • Ethyl homovanillate (5 g) was mixed with cinnamyl alcohol (7.5 g) and 25% sodium methylate solution (0.52 g) and heated to 150-170° C., vacuum applied above approximately 130° C. and MeOH/EtOH distilled from the reaction mixture for 1-3 h. It was diluted with MTBE, the organic phase was washed once with saturated aqueous NH 4 Cl solution and once with water and the solvent was removed under vacuum. Excess cinnamyl alcohol was then removed by distillation and the product was obtained by column chromatographic purification on silica gel or fractionated distillation with a yield of 40-50%.
  • the substance to be tasted was dissolved in ethanol and the ethanolic solution was then diluted with 5% sugar solution (final concentration: 25 ppm).
  • sugar solution final concentration: 25 ppm
  • the oral cavity was rinsed and spat out by 4 tasters with approx. 5 ml of the sugar solution.
  • the pungency was assessed on a scale of 1 (very weak)-9 (very strong) and the profile was assessed.
  • Example 6 Isointensity of Esters of Homovanillinic Acid when Compared to Nonivamide and a Capsicum Extract
  • the substance to be tasted was dissolved in ethanol and the ethanolic solution was then diluted with 5% sugar solution (final concentration: 10 ppm).
  • 5% sugar solution final concentration: 10 ppm.
  • Capsicum extract with 1,000,000 SHU (0.3-10 ppm) and nonivamide (0.1-1 ppm) were prepared in 5% sugar solution in increasing concentration.
  • the oral cavity was rinsed and spat out by 4 tasters with approx. 5 ml of the solution to be tasted and assessed against the reference series.
  • the pungency of 10 ppm of hexyl-2-(4-hydroxy-3-methoxyphenyl) acetate (21) is comparable to the one of 8.5 ppm Capsicum extract with 1,000,000 SHU.
  • the thresholds were determined according to ASTM E 679-91 (“Standard Practice for Determination of Odor and Taste Thresholds By a Forced-Choice Ascending Concentration Series Method of Limits1”). It is the respective flavour stimulus threshold to Vittel® water.
  • the threshold of hexyl-2-(4-hydroxy-3-methoxyphenyl) acetate (21) in water is at 1.7 ppm (1700 ppb).
  • the threshold of ethyl-2-(4-hydroxy-3-methoxyphenyl) acetate (17) in water is at 29.5 ppm (29460 ppb).
  • the threshold of butyl-2-(4-hydroxy-3-methoxyphenyl) acetate (19) in water is at 3.5 ppm (3540 ppb).
  • Example 9 Combination of Esters of Homovanillic Acid with Grains of Paradise Extract, Nonivamide and a Capsicum Extract
  • Capsicum 2 2 2 2 2 5 5 5 5 5 5 5 2 2 extract HVE 17 — 50 100 — — — 50 100 — — — — 50 100 — — — — 50 100 — — — — 50 HVE 19 — — 10 25 — — — 10 25 — 10 — — *not according to the invention
  • Esters of homovanillic acid have an intensifying effect on the used compounds.
  • a faster onset of the pungency was detected for the combination of grains of paradise extract (PN 300953, Symrise) with ethyl-2-(4-hydroxy-3-methoxyphenyl) acetate (17, examples 2 and 3).
  • ethyl-2-(4-hydroxy-3-methoxyphenyl) acetate (17) with nonivamide examples 7 and 8 as well as 12 and 13
  • the pungency of nonivamide was intensified at both of the tested concentrations, wherein this intensification corresponded to more than just the additive effect. Furthermore, a faster onset of the pungency was detected.
  • Example 10 Increase in the Alcohol Pungency of an Ethanolic Solution by ethyl-2-(4-hydroxy-3-methoxyphenyl) acetate (17)
  • the base solution (5% sugar solution with 20% ethanol, example 1) was described as alcoholic, burning.
  • Further increase to 20 ppm and 50 ppm (examples 2-5) resulted in an additional pungency effect.
  • Polymethoxylated flavone PMF 60 on its own (example 6) resulted in an increase of the alcoholic taste in the tasting solution, but not a burning sensation in the mouth compared to example 1.
  • Test solutions with 4-10 ppm ester of homovanillic acid were sensorially evaluated in a 5% sugar solution and were compared to a test solution of 10 ppm vanillyl butyl ether.
  • Ethyl-2-(4-hydroxy-3-methoxyphenyl) acetate (17) had a milder warming effect compared to vanillyl butyl ether.
  • Butyl-2-(4-hydroxy-3-methoxyphenyl) acetate (19) had a more marked warming effect than vanillyl butyl ether.
  • Isobutyl-2-(4-hydroxy-3-methoxyphenyl) acetate (9) showed a warming effect similar to vanillyl butyl ether, but which lasted for a longer period.
  • Propyl-2-(4-hydroxy-3-methoxyphenyl) acetate (18) also showed a long-lasting warming effect, but which occurred at a comparatively later time.
  • ingredients are mixed in the above-specified quantity ratios and then taken up in propylene glycol and dissolved completely by slight warming.
  • the two components are dissolved in a mixture of ethanol and demineralised water and are spray-dried afterwards.
  • flavour compositions were used in the below-described application examples.
  • Parts A to D are mixed and kneaded intensively.
  • the obtained raw mass can then be processed to ready-to-eat chewing gums, e.g. in the form of thin strips.
  • Version A liqueur base 5.5% v/v+0.3% of a 10% solution of an extract of grains of paradise in ethanol
  • Version B liqueur base 5.5% v/v+0.075% of a 10% solution of an extract of grains of paradise in ethanol+0.2% of a solution of 1% ethyl-2-(4-hydroxy-3-methoxyphenyl) acetate (17) in ethanol (corresponds to 20 ppm).
  • Version C liqueur base 5.5% v/v+0.075% of a 10% solution of an extract of grains of paradise in ethanol+0.01% of a solution of 1% ethyl-2-(4-hydroxy-3-methoxyphenyl) acetate (17) in ethanol (corresponds to 1 ppm).
  • the alcohol pungency of the reference sample is sensorially imitated better than in version A.
  • Version A and the reference sample are sensorially evaluated as being very similar.
  • Preparation Heat the components of phases A and B separately to about 80° C. Stir phase B intro phase A while homogenising. Cool to about 40° C. while stirring, add the phases C and D and shortly homogenise again. Cool to room temperature while stirring.
  • palatinite was mixed with water. The mixture was then melted at 165° C. and subsequently cooled to 115° C. The peppermint flavour and the flavour preparation (example 1) were then added. The mixtures were poured into moulds after mixing, removed from the moulds after solidifying, and then packaged individually.
  • the green tea concentrate is mixed with the 1% solution of ethyl-2-(4-hydroxy-3-methoxy-phenyl)acetate (17) in propylene glycol in the case of drink A, and with the 1% solution 3-phenylpropyl-2-(4-hydroxy-3-methoxyphenyl) acetate (22) in propylene glycol in the case of drink B. Subsequently, it is filled with demineralised water and mixed again thoroughly. The product is filtered afterwards, packaged ready-to-use, and sterilised at 118° C.
  • the taste of the drinks A and B is evaluated by a panel of educated testers as clearly preferred to the non-flavoured green tea concentrate.
  • the bitterness and the astringency is reduced by the addition of the compounds according to the invention.
  • the esters of homovanillic acid were pre-dissolved in 10% or 1% ethanol, respectively.
  • Black tea extract was dissolved in water and stirred together with sugar, a flavour preparation (peach taste), as well as the ethanol solutions of the esters of homovanillic acid in a beaker.

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US20190169111A1 (en) * 2016-08-04 2019-06-06 Takasago International Corporation Warming sensation compounds
US20230059747A1 (en) * 2019-06-13 2023-02-23 Symrise Ag A cooling preparation

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JP6794758B2 (ja) * 2015-10-21 2020-12-02 大正製薬株式会社 経口液体医薬組成物
CN105779217A (zh) * 2016-02-01 2016-07-20 李滋星 生姜酚生物饮品及其制备方法
EP3432878A1 (de) * 2016-03-23 2019-01-30 Symrise AG Homovanillinsäure-ester zum reduzieren oder inhibieren der fettsäureaufnahme im dünndarm
WO2019063069A1 (de) * 2017-09-27 2019-04-04 Symrise Ag Amide zur erzeugung eines trigeminalen effekts
WO2020015816A1 (de) 2018-07-16 2020-01-23 Symrise Ag Zusammensetzung zur substitution von zucker in backwaren
EP3911172A1 (de) 2019-01-18 2021-11-24 Symrise AG Kombinationsmittel
US20230167045A1 (en) 2020-04-27 2023-06-01 Symrise Ag Method for producing esters of homovanillic acid
CN114601743B (zh) * 2022-03-22 2022-09-13 宝萃生物科技有限公司 一种二氢杨梅素脂质体及其制备和应用

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US20230059747A1 (en) * 2019-06-13 2023-02-23 Symrise Ag A cooling preparation

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