CN1976895A - Use of alkyloxyalcanic acid amides, in particular in the form of aromatic substances and a novel alkyloxyalcanic acid amide - Google Patents
Use of alkyloxyalcanic acid amides, in particular in the form of aromatic substances and a novel alkyloxyalcanic acid amide Download PDFInfo
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- CN1976895A CN1976895A CNA200580022147XA CN200580022147A CN1976895A CN 1976895 A CN1976895 A CN 1976895A CN A200580022147X A CNA200580022147X A CN A200580022147XA CN 200580022147 A CN200580022147 A CN 200580022147A CN 1976895 A CN1976895 A CN 1976895A
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
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- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/08—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
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Abstract
The invention relates to the use of defined alkyloxyalcanic acid amides in the form of (i) aromatic substances (1) and/or (ii) for producing a formication and/or (iii) for producing a feeling of sharpness and/or for exciting salivation in a mouth and/or (v) for intensifying the taste of ethanol and/or for imitating the taste of ethanol.
Description
The present invention relates to the purposes of special alkoxyalkanoic acids acid amides, as (i) seasonings and/or (ii) produce tingle and/or (iii) produce pungent sense and/or (iv) stimulate the oral cavity to salivation and/or (v) strengthen the alcoholic acid taste and/or (vi) simulate the alcoholic acid taste, be preferred for the nutrition consumer's goods, oral hygiene products or abstract the recreational consumption product or oral pharmaceutical goods.The invention still further relates to novel alkoxyalkanoic acids acid amides and the goods that contain the used alkoxyalkanoic acids acid amides of with good grounds the present invention.
As far back as 1871 with regard to known from multiple pepper, especially the capsaicine of capsicum [N-(4-hydroxyl-3-methoxybenzyl)-8-methyl-(6E)-pelargonamide, general formula (1)] and other capsaicine alkaloid are used as---sharp flavor and produce the seasonings of hotness.Produce the material of hotness or have the material that the material that produces the hotness effect is interpreted as producing hot organoleptic impression.Suitably (threshold value is about 1: 10 to the capsaicine alkaloid of low dosage
5Extent of dilution) in the oral cavity, only feel joyful, achromatic stimulus and hotness, but this is persistent.Yet capsaicine brings some problems, because its bigger acute toxicity (LD
50(mouse is oral) 47mg), make its goods application difficult, and frequent and excessive use causes chronic gastritis, kidney and hepar damnification (Rompp LexikonNaturstoffchemie, Thieme 1997, P109).Therefore, although it has good sensorial characteristics, but need the less pungent substance of problem.Though be present in piperine (1-piperonyl piperidines, general formula (2)) in the white pepper also produce pungent sensation (Rompp LexikonNaturstoffchemie, Thieme 1997, P500), its pungent relatively degree only has about 1% of capsaicine.And piperine has the association of the inherent pepper flavor of intensive, the use of therefore only limiting the quantity of in various products.The ethanol of higher concentration (from about 1%) (is commonly called as: alcohol) also produce pungent and scorching hot sense of taste.On the other hand, for example for ethics and religion reason, ethanol does not allow to be used for all food, and should reduce yet or avoid alcoholic acid consumption basically for healthy reason.
Above-mentioned substance can not cause the effect that salivation stream increases, and this is needed outside pungent sense, especially in mouth wash shua.Naturally occurring alkane acid amides spilanthol (general formula (3)) and pellitorine (general formula (4)) part are applicable to these purposes, they are except saliva stimulating and tingle effect, also in the oral cavity, display lasting quality and numb effect, this is not that all application are all needed (cf.H.C.F.Su and R.Horvat, J Agric.Food Chem.1981, vol.29, pages115-118).And, because its highly unsaturated structure, so they are difficult synthetic and very responsive to the effect of oxygen and light.
Main purpose of the present invention provides and is suitable for producing tingle and/or produces pungent sense/hotness and/or stimulate the salivation material of (saliva effect) of oral cavity.These materials also should be able to be simulated the impression of the pungent and warm sense of taste of alcoholic acid.In addition, these materials should preferably have relative neutral aroma and flavor feature, significantly numbness does not act on, is easy to synthetic and stable.The material that is provided also should be used safely in the nutrition consumer's goods, oral hygiene products or abstract the recreational consumption product or oral pharmaceutical goods.
Realize that above-mentioned purpose is according to the alkoxyalkanoic acids acid amides that the invention provides following general formula (5a)
Wherein
N represents numeral 1 or 2
With
R
1Represent alkyl (limiting as follows),
With
R
2The optional low carbon number alkyl (limiting as follows) that is substituted with one or more hydroxyls of representative,
Or
The alkoxyalkanoic acids acid amides of general formula (5b),
Wherein
N represents numeral 1 or 2
With
R
1Represent alkyl (limiting as follows),
With
M represents numeral 1 or 2
With
R ' and R " independently represent hydrogen atom or methyl or ethyl or represent methylene radical together respectively.
Or
The alkoxyalkanoic acids acid amides of general formula (5c)
Wherein
N represents numeral 1 or 2
With
R
1Represent alkyl (limiting as follows),
With
R
2And R
3The optional identical or different low carbon number alkyl (limiting as follows) that is substituted with one or more hydroxyls of independent respectively representative,
Or
R
2And R
3Form alkylidene group (limiting as follows) together,
Or
The mixture of general formula (5a), (5b) and/or two or more compounds (5c), as (i) seasonings and/or (ii) produce tingle and/or (iii) produce pungent (or heat) sense and/or (iv) stimulate the oral cavity to salivation and/or (v) strengthen the alcoholic acid taste and/or (vi) simulate the alcoholic acid taste, specifically be used for the nutrition consumer's goods, oral hygiene products or abstract the recreational consumption product or oral pharmaceutical goods.
When having unsymmetrical carbon, general formula (5a), (5b) and compound (5c) can adopt pure enantiomorph and/or diastereomer or the two might ratio the form of mixture.
Below explanation specifically is applied to general formula (5a), (5b) and compound (5c):
Alkyl in the meaning of the present invention is the alkyl that line style, side chain or cyclic have 1-8 carbon atom, and following radicals is preferred: methyl, ethyl, n-propyl (referring to following compound 10-13,15 and 17), normal-butyl (referring to following compound 6-9,14 and 16), n-pentyl, n-hexyl.
Below explanation is used for general formula (5a) and compound (5c):
Low carbon number alkyl in the meaning of the present invention is the line style with 1-5 carbon atom, side chain or cyclic alkyl, described alkyl is chosen wantonly and is substituted with one or more hydroxyls, especially a preferred hydroxyl, preferred following radicals: methyl, ethyl, the 2-hydroxyethyl, propyl group, the 3-hydroxypropyl, the 2-propyl group, cyclopropyl, butyl, the 2-butyl, 3-methyl-propyl (being isobutyl-), 2-hydroxyl--2--methyl-propyl, cyclobutyl, 1-or 2-methyl cyclopropyl, the 2-methyl-propyl, amyl group, the 2-amyl group, the 3-amyl group, the 2-methyl butyl, the 3-methyl butyl, cyclopentyl and 1-, 2-or 3-methyl cyclobutyl, but especially preferred 2-hydroxyethyl (referring to compound 16 and 17), isobutyl-(referring to compound 6 and 10), or 2-methyl butyl (referring to compound 7 and 11).
Below explanation is applied to general formula (5c) especially:
Alkylidene group in the meaning of the present invention is the alkylidene group with 2-6 carbon atom, the described alkylidene group of part can preferably be substituted with one or more low carbon number alkyl, preferred following radicals: ethylidene, propylidene, butylidene (referring to following formula 9 and 13), pentylidene (referring to following formula 8 and 12).
The invention still further relates to the alkoxyalkanoic acids acid amides of following general formula:
Wherein
N in each general formula, R
1, R
2, m, R ', R " have provide above for (5a) and implication (5b).These compounds are new.It is applicable to above-mentioned purpose, and pungent sense, possible hotness and/or tingle and/or stimulation stream saliva especially are provided, and this is surprising for prior art.
General formula (5a) and alkoxyalkanoic acids acid amides (5b) can be produced by known alkoxyalkanoic acids or its alkyl ester by known acid amides synthetic method (referring to for example practical organic chemistry textbook) itself.For example, alkoxyalkanoic acids can be transformed into corresponding sour chlorine and use corresponding alkylamine separately or by means of auxiliary alkali, use or do not use solvent that it simply is transformed into the alkoxyalkanoic acids acid amides, and by ordinary method (for example distillation, crystallization, chromatogram) purifying.Figure below illustrates this method.
The alkoxyalkanoic acids acid amides of some general formulas (5c) had been described in the past.For example, US 5,744, and 631 have described N, and N-diethyl-3-oxygen in last of the ten Heavenly stems base propionic acid acid amides (CA 187885-89-8) is as antiviral and/or antifungus active substance.US 3,228, and 832 have described N, and N-diethyl-2-oxygen in last of the ten Heavenly stems base propionic acid acid amides (CA88591-89-3) and other N, N-dialkyl derivatives are together as the medicament for the treatment of helminth in the animal body.
Yet the purposes of the above-mentioned application of general formula (5a), (5b) and alkoxyalkanoic acids acid amides (5c) is unknown and be surprising before being.
Making those skilled in the art surprised especially and unforeseen is that alkoxyalkanoic acids acid amides used according to the invention produces fiber crops thorn taste impression and/or the pungent sense of describing and/or promotes salivation in feeling evaluation.Also surprisingly, when using with suitable high density, the sense organ impression is relatively strong with relative more lasting, and therefore (5a), (5b) and compound (5c) (with its mixture) significantly are suitable for aforementioned purpose.
Particularly advantageous is that the alkoxyalkanoic acids acid amides of general formula (5a) produces the sense of taste impression that is described to tingle and urgees salivation and not significant pungent and/or hot and/or numb sensation strongly.
Also particularly advantageously be, the alkoxyalkanoic acids acid amides of general formula (5b) produces joyful pungent and warmth sensation impression and does not show as for example bitter taste and the calcination of the lasting impression of Dihydrocapsaicin of capsaicin derivates, therefore, the alkoxyalkanoic acids acid amides of general formula (5b) is specially adapted to strengthen alcoholic acid sense organ impression and/or simulation alcoholic acid sense organ impression.
Preferably have m=1, R '=H and R "=compound of the general formula (5b) of H, methyl or ethyl, this is because it has special pungent sense.
In addition, with respect to oxidation, light or radiation effect or other decomposition reaction, for example spilanthol (3) or pellitorine (4) are more stable than height unsaturated alkyl amine for alkoxyalkanoic acids acid amides used according to the invention, because they do not have two keys.
Following alkoxyalkanoic acids acid amides used according to the invention is particularly preferred:
2-ethoxyacetic acid in heptan N-isobutyl-acid amides (compound 6)
2-ethoxyacetic acid in heptan N-2-(methyl butyl) acid amides (compound 7)
2-ethoxyacetic acid in heptan N-piperidines acid amides (compound 8)
2-ethoxyacetic acid in heptan N-tetramethyleneimine acid amides (compound 9)
3-hexyloxy propionic acid N-isobutyl-acid amides (compound 10)
3-hexyloxy propionic acid N-2-(methyl butyl) acid amides (compound 11)
3-hexyloxy propionic acid N-piperidines acid amides (compound 12)
3-hexyloxy propionic acid N-tetramethyleneimine acid amides (compound 13)
2-ethoxyacetic acid in heptan N-(4-hydroxyl-3-methoxy-benzyl) acid amides (compound 14)
3-hexyloxy propionic acid N-(4-hydroxyl-3-methoxy-benzyl) acid amides (compound 15)
2-ethoxyacetic acid in heptan N-(2 hydroxyethyl) acid amides (compound 16)
3-hexyloxy propionic acid N-(2 hydroxyethyl) acid amides (compound 17)
With the mixture that contains 2 kinds, 3 kinds or more compounds 6-17.
Because its special saliva effect, special preferred compound 6 and 7 and the compound of other general formula (5a).
The present invention also provides finished product, work in-process and smell, local flavor and taste composition, and described composition contains one or more alkoxyalkanoic acids acid amides used according to the invention.In this regard, more following explanation and claims.
Alkoxyalkanoic acids acid amides used according to the invention (perhaps its mixture) can also be applied to makeup or dermatological formulation to produce hotness on skin.
In a preferred embodiment of the invention, have pungent taste according to alkoxyalkanoic acids acid amides of the present invention (perhaps its mixture) and one or more and/or produce other material of hotness or the plant milk extract of (especially) pungent taste is used in combination.Like this, can in corresponding articles, reach plentiful especially organoleptic characteristics.Particularly, the plant milk extract of alkoxyalkanoic acids acid amides used according to the invention and pungent taste is with ratio 0.01: 1-100: 1, preferred 0.1: 1-10: the organoleptic characteristics that 1 combination results is joyful.
The material that is applicable to the pungent taste of having of combination or produces hotness is specifically: capsaicine, Dihydrocapsaicin, zingiberol, Shogaol, salad oil, piperine, paraffinic acid N-vanilla acid amides, especially n-nonanoic acid N-vanilla acid amides, pellitorine or spilanthol, 2-nonenoic acid N-4-hydroxy 3-methoxybenzene acid amides, the alkyl oxide of N-4-hydroxyl-3-methoxy-benzyl alcohol, especially 4-hydroxyl-3-methoxy-benzyl-n-butyl ether, the alkyl oxide of 4-acyloxy-3-methoxy-benzyl alcohol, especially 4-second acyloxy-3-methoxy-benzyl alcohol-n-butyl ether and 4-second acyloxy-3-methoxy-benzyl alcohol-n-hexyl ether, the alkyl oxide of 3-hydroxyl-4-methoxy-benzyl alcohol, 3, the alkyl oxide of 4-dimethoxy-benzyl alcohol, the alkyl oxide of 3-oxyethyl group-4-hydroxybenzylalcohol, 3, the alkyl oxide of 4-methylenedioxy benzyl alcohol, (4-hydroxy 3-methoxybenzene base) ethanamide, especially (4-hydroxy 3-methoxybenzene base) positive decoylamide of acetate N-, vanilmandelic acid alkylamide according to WO2003/106404, according to EP2003/1,323,356 forulic acid phenelyl acid amides, alkenoic acid N-alkylamide, nicotinoyl aldehyde, nicotinic acid methyl ester, the nicotinic acid propyl ester, 2-fourth oxygen ethyl nicotinate, benzyl nicotinate, 1-acetoxyl p-allylphenol, polygodial and isodrimeninol.
The combination (referring to for example DE103 51 422) of also preferred sharp flavor and saliva stimulating excretory olefinic carboxylic acid (alkenecarboxylic acid) N-alkylamide.
The plant milk extract that is applicable to the sharp flavor of combination is all plant milk extracts that are suitable for the pungent and/or hotness impression of causing of nutrition.For this reason, the example of preferred plant milk extract is Fructus Piperis extract (Piperssp, especially Piper nigrum), Fructus Piperis extract (polygonum ssp, especially polygonumhysropiper), allium (Allium ssp) extract (especially onion and Bulbus Allii extract), radish extract (raphanus ssp), horseradish extract (cochlearia armoracia), black mustard end extract (Brassica nigra), wild or yellow mustard extract (Sinapis ssp, especially Sinapisarvensis and Sinapis alba) expelling parasite chrysanthemum root extract (Ancyclus ssp, especially coneflower extract (Echinaceae ssp) Ancycluspyrethrum L), Sichuan Fructus Piperis extract (Zanthoxylumssp, especially Spilanthes acmella), Fructus Capsici extract (Capsicum ssp, especially Capsicumfrutescens), Amomum melegueta extract (Aframomum ssp, especially Aframomummelegueta[rose] K.Schum), Rhizoma Zingiberis Recens extract (Kaempferia galanga or Alpiniagalanga) and Pilocarpus jaborandi extract (Pilocarpus species, especially Pilocarpusjaborabdi).
The plant milk extract of sharp flavor can obtain from corresponding fresh or dried plant or plant part usually, but especially from white, green or piper nigrum seed, white pepper seed, onion and garlic, radish root, horseradish, mustard seed, coneflower root, expelling parasite chrysanthemum root, plant part, red pepper pod, Amomum melegueta or the ginger or the Rhizoma Alpiniae Officinarum root that belong to from the plant part of Zanthoxylum, from Herba Cancriniae lasiocarpae.For this purpose, usually extracting preferably the dried plant part of pulverizing in advance with the solvent that is applicable to food and abstract the recreational consumption product under the temperature range of the boiling point of solvent separately at 0 ℃, filter and concentrate all or part of filtrate then, preferred distillation, lyophilize or spraying drying.The crude extract that this method obtains can further be processed, and for example utilizes the steam of pressure from 0.01 millibar to standard atmosphere pressure, and/or with the solvent that is applicable to food and abstract the recreational consumption product.The solvent that is applicable to food and abstract the recreational consumption product is the mixture of water, ethanol, methyl alcohol, propylene glycol, glycerine, acetone, methylene dichloride, diethyl ether, normal hexane, heptane, glycerol acetate, vegetables oil or fat, supercritical co or above-mentioned solvent for example.
In concrete preferred embodiment of the present invention, the plant milk extract that causes tingle and/or saliva stimulating secretion or contain these materials according to alkoxyalkanoic acids acid amides of the present invention (perhaps its mixture) and other is used in combination.
As causing tingle and/or saliva stimulating excretory material, operable is for example some unsaturated alkyl acid amides (for example pellitorine, spilanthol, salad oil), alkaloid (for example pilocarpine), saliva stimulating excretory peptide class (for example P material, tachykinin, physalaemin), and simple fruit acid (for example citric acid, tartrate).
In another concrete preferred embodiment of the present invention, use according to alkoxyalkanoic acids acid amides of the present invention (perhaps its mixture) and one or more combinations of substances that causes the nice and cool effect of physiology.
As the material that causes the nice and cool effect of physiology, operable is menthol and menthol derivative (L-menthol for example, racemic menthol), _ basic ether ((L-_ oxygen base)-1 for example, the 2-propylene glycol, (L-_ oxygen base)-2-methyl isophthalic acid, the 2-propylene glycol, _ ylmethyl ester), _ basic ester (acetate _ ester for example, isopropylformic acid _ ester, lactic acid _ ester, (2-methoxyl group) acetate _ ester, (2-methoxy ethoxy) acetate _ ester, Pyrrolidonecarboxylic acid _ ester), carbonic acid _ ester (carbonate propanediol _ ester for example, ethylene carbonate _ ester, carbonic acid glycerine _ ester), the half ester of peppermint alcohol and carboxylic acid (succsinic acid _ ester for example, pentanedioic acid _ ester), _ alkane methane amide (for example _ yl carboxylic acid N-ethanamide) _ ketone and _ ketone derivatives (for example _ ketone glycerol ketals), 2,3-dimethyl-2-(2-propyl group) butanoic acid derivative (for example 2,3-dimethyl-2-(2-propyl group) butyric acid N-methane amide), isopulegol or its ester (1-(-)-isopulegol, acetate 1-(-)-isopulegol ester), _ alkane derivatives (for example right-_ alkane-3, the 8-glycol), cubebol, pyrrolidinone derivatives, cycloalkyl derovatives (for example 3-methyl-2-(1-pyrrolidyl)-2-cyclopentenes-1-ketone) or icilin.
The invention still further relates to the nutrition consumer's goods, oral hygiene products or abstract the recreational consumption product, described goods comprise generation tingle and/or pungent and/or hot and/or generation salivation stream and/or the reinforcement or the simulation alcoholic acid taste of significant quantity, general formula (5a), (5b) or alkoxyalkanoic acids acid amides (5c) or two or more general formulas (5a), (5b) and/or the compound (5c) of the generation tingle of preferred significant quantity or pungent sense or generation salivation stream or reinforcement or simulation ethanol taste.
Wherein, in each general formula, n, m, R
1, R
2, R
3, R ' and R " have an implication that provides above.
These goods according to the present invention randomly comprise the basis of other routine that is used for food or abstract the recreational consumption product or oral hygiene products, auxiliary and additive materials.Described goods comprise one or more general formulas (5a) based on the goods gross weight, (5b) and/or the alkoxyalkanoic acids acid amides (5c) of 0.0000001wt%-10wt%, preferred 0.00001-1wt%, concrete preferred 0.00001wt%-0.1wt% usually.Can contain 0.0000001-99.9999999wt%, preferred 10-80wt% the basis based on other routine that is used for food or abstract the recreational consumption product or oral hygiene products of goods gross weight, assist and additive materials.And described goods can comprise the water based on the goods gross weight up to 99.9999999wt%, preferred 5-80wt%.
The nutrition consumer's goods or abstract the recreational consumption product are for example to bake thing (bread for example, biscuit, cake, other grilled product), candy is (for example chocolate, the chocolate bar product, other rod-shaped objects, pectin, hard and soft candy, chewing gum), contain ethanol or do not contain alcoholic acid beverage (coffee for example, tea, grape wine, contain beverage vinous, beer, the beverage that contains beer, sweet wine, liquor, brandy, the fruit beverage of foaming, Deng oozing beverage, soft drink, nectar, fruits and vegetables juice, fruit syrup or vegetables juice goods), instant drinks (instant cocoa drink for example, the instant tea beverage, the soluble coffee beverage), meat product (ham for example, new fresh sausage or dry sausage goods, spiced or marinade fresh or bacon goods), egg or egg-products (dried egg, albumen, yolk), cereal product (breakfast cereal for example, muesli bar (muesli bars), the rice made products that boils in advance), milk preparation (dairy beverage for example, milk ice cream, yogourt, kephir, fresh cheese, soft cheese, rat cheese, dried milk, whey, butter, buttermilk, fruit product (ketchup for example, food flavouring, dried vegetables, frozen vegetables, the vegetables of cooking in advance, vegetable-pickling food), snack (potato slices that for example bake or deep-fried or potato group goods, extrudate based on corn or peanut), product or its emulsion (mayonnaise for example based on fat and oil, remoulade, seasonings), meat that other is instant and soup (for example dried soup, instant soups, the soup of cooking in advance), spice, condiment mixture and in particular for the condiment of snack part.Goods in the meaning of the present invention can also be as the work in-process of producing other nutrition consumer's goods or abstract the recreational consumption product.Goods in the meaning of the present invention can also be taked dispersion, emulsion, pulvis, solution, the paste in capsule, tablet (non-dressing and coating tablet, for example enteric coating), drageeing, granule, pill, solid mixture, the liquid phase or be used as other goods that are suitable for swallowing or chewing of dietary supplement.
Confirm that also particularly advantageous is alkoxyalkanoic acids acid amides used according to the invention, especially in the goods of alcohol drink or alcoholic beverages, simulating alcoholic acid sharp flavor with the preferably combination of the plant milk extract of sharp flavor, therefore, it can reduce in the alcohol drink or the ethanol content in the goods of alcoholic beverages or replace ethanol fully and keep same sensory evaluation.
The taste that resembles the ethanol flavor is preferably determined by the amount of alkoxyalkanoic acids acid amides basically.If purpose is to compare reduction ethanol with the compared products with roughly the same taste, be 0.5wt% then according to the alcoholic acid maximum that exists in these goods of the present invention.Such goods preferably comprise the ethanol that is less than 0.1wt%.
Article according to the invention is preferably taked the form of smell, local flavor or taste composition or condiment mixture.
Can be preferred for seasonings according to general formula of the present invention (5a), (5b) or alkoxyalkanoic acids acid amides (5c) does with the mouth of avoiding producing when corn, potato or rice flour crisp and snack in consumption and strengthens overall organoleptic impression.
Except alkoxyalkanoic acids acid amides used according to the invention, preferred seasonings comprises for example synthetic, natural or is equal to natural seasonings and carrier maltodextrin, salt ordinary salt, spice red chilly powder and pepper, seasonings for example monosodium glutamate and/or hypoxanthylic acid of asccharin and flavour enhancer for example for example for example for example.
Oral hygiene products specifically is for example toothpaste, gutta-percha, tooth powder, mouth wash shua, chewing gum and other oral health-care product of oral health-care product.
The oral health-care product that contains alkoxyalkanoic acids acid amides used according to the invention comprises for example silicon-dioxide, lime carbonate, calcium phosphate, aluminum oxide and/or hydroxyapatite, tensio-active agent sodium lauryl sulphate, sarcosyl and/or alkyl amido betaine, wetting agent for example Xylo-Mucine, polyoxyethylene glycol, carrageenin and/or Laponites of glycerine and/or sorbyl alcohol, thickening material for example for example of grinding system (abrasive or rumbling compound) usually
_Sweeting agent is asccharin for example, seasonings is Saccharum lactis for example, sequestering agent is the hydroxyl flavanone for example, ice-cold material is menthol or menthol derivative for example, stablizer and active substance be Sodium Fluoride for example, sodium monoflurophosphate, tin difluoride, the tetrafluoride ammonium, zinc citrate, zinc sulfate, stannous pyrophosphate, tindichloride, the mixture of different tetra-sodiums, triclosan (triclosan), cetylpyridinium chloride (Cetylpyridinium Chloride), Aluctyl, Tripotassium Citrate, saltpetre, Repone K, strontium chloride, hydrogen peroxide, seasonings and/or sodium bicarbonate.
The chewing gum that contains alkoxyalkanoic acids acid amides used according to the invention comprise usually chew that matrix promptly becomes plasticity in the process of chewing chew material, various types of sugar, sugar replacement, sweeting agent, sugar alcohol, wetting agent, thickening material, emulsifying agent, seasonings and stablizer.
The invention still further relates to the oral pharmaceutical goods, described pharmaceutical preparation contains realization tingle realization trigeminal nerve effect (stimulation), preferred significant quantity or general formula (5a) or alkoxyalkanoic acids acid amides (5b) or two or more general formulas (5a) or the compound (5b) pungent or generation salivation stream of significant quantity.
Oral pharmaceutical goods in the meaning of the present invention be take in for example capsule, tablet (non-dressing and coating tablet, for example enteric coating), drageeing, granule, pill, solid mixture, the liquid phase dispersion, emulsion, pulvis, solution, paste or as the form that is suitable for other goods of swallowing or chewing of dietary supplement.Wherein, except alkoxyalkanoic acids acid amides used according to the invention, also comprise the other medicines active substance or be applicable to the active substance of food supplement, and as prescription only, only pharmacy or other medicines or food supplement.
Other medicines active substance or the active substance that is applicable to food supplement can be VITAMIN for example, mineral substance, microbiotic, bactericide, mycocide, antiviral agent, insect repellent, anti-mycotic agent or other anti-microbial active matter, treatment aged medicament, the for example imbalance of heart and the recycle system of lacking of proper care in the treatment, treat medicament optimum or malignant tumour (for example cytostat), preventing cancer, the medicament of prevention or treatment dementia, improve the medicament of cognitive behavior, reduce blood agglutinative active substance, the medicament of treatment illness in eye, alleviate the active substance of heating and the active substance of alleviation inflammatory diseases.
Goods in the meaning of the present invention can also take in capsule, tablet (non-dressing and coating tablet, for example enteric coating), drageeing, granule, pill, solid mixture, the liquid phase dispersion, emulsion, pulvis, solution, paste or as the form that is suitable for other preparation of swallowing or chewing of dietary supplement.
Comprise one or more general formulas (5a), (5b) or alkoxyalkanoic acids acid amides (5c) article according to the invention can by with the alkoxyalkanoic acids acid amides as material, solution or and the form of mixtures of solid or liquid vehicle be incorporated in the nutrition consumer's goods, oral hygiene products or the abstract the recreational consumption product and produce.The article according to the invention of solution form advantageously is transformed into solid articles by spraying drying.
According to the alternate preferred embodiment, in order to produce according to preparation of the present invention, can be at first be incorporated into emulsion with the alkoxyalkanoic acids acid amides with according to other optional components of preparation of the present invention, liposome for example derives from phosphatidylcholine, microballoon, nanometer ball or introducing capsule, the extrudate of granule or matrix, it for example is applicable to for example starch of food and abstract the recreational consumption product, starch derivative, Mierocrystalline cellulose or derivatived cellulose (for example hydroxypropylcellulose), other polysaccharide (for example alginate), natural fat, natural wax (beeswax for example, carnauba wax) or protein gelatin for example.
In another alternative preferred production process, the alkoxyalkanoic acids acid amides at first with one or more suitable complexing agents for example cyclodextrin or cyclodextrin derivative, preferred beta-cyclodextrin complexing, and use with this form complexed.
The special matrix of preferably selecting in article according to the invention obtains persistent seasoning effect thus to postpone the release of alkoxyalkanoic acids acid amides from matrix.
Article according to the invention preferably also comprises at least aly having pungent taste, produce hotness or cause tingle or the material or at least a plant milk extract that contains this (these) material of saliva stimulating secretion or the ice-cold effect of physiology.
The basis that is used for other routine of food or abstract the recreational consumption product; auxiliary and additive materials can be as other component according to nutrition of the present invention or abstract the recreational consumption goods; water for example; fresh or finished plant or animal base mateiral or starting material (are for example given birth to; roasting; exsiccant; fermentation; smoke cured and/or boil meat; egg; bone; cartilage; fish; Crustacean and shellfish fish; vegetables; fruit; grass; nut; vegetables or fruit syrup or paste or its mixture); digestible or indigestible carbohydrate (sucrose for example; maltose; fructose; glucose; dextrin; amylose starch; amylopectin; inulin; xylan; Mierocrystalline cellulose); sugar alcohol (sorbyl alcohol for example; N.F,USP MANNITOL; Xylitol); natural or hydrogenated fatty acid (tallow for example; lard; palm kernel fat; cupraol; hydrogenated vegetable oil); fatty oil (sunflower oil for example; peanut oil; Semen Maydis oil; Ji oil; sweet oil; Walnut oil.; fish oil; soybean oil; sesame seed oil); lipid acid and its salt (potassium stearate for example; potassium palmitate); protein source or non-protein source acidic amino acid and relevant compound (taurine for example; creatine; creatinine); the peptide class; natural or finished protein (for example gelatin); enzyme (peptase for example; Polyglucosidase; lipase); nucleic acid; Nucleotide (phosphoinositide); local flavor enhancing substance (monosodium glutamate for example; the 2-phenoxy propionic acid; according to EP1; 258,200 hydroxyl flavanone); emulsifying agent (Yelkin TTS for example; DG); stablizer (carrageenan for example; alginate; Viscogum BE; guar gum); sanitas (phenylformic acid for example; xitix); antioxidant (for example tocopherol or its derivative; xitix or its derivative); sequestrant (for example citric acid); organic or inorganic souring agent (oxysuccinic acid for example; acetate; citric acid; tartrate; phosphoric acid); bitters (quinine for example; trimethyl-xanthine; obacalactone); sweeting agent (asccharin for example; asccharin; Sodium Cyclamate; aspartame; knob is sweet; neohesperidin; dihydrochalcone; tagatose; Sucralose); mineral salt (sodium-chlor for example; Repone K; magnesium chloride; sodium phosphate); the material of inhibitory enzyme brown stain (sulphite for example; xitix); essential oil; plant milk extract; natural or synthetic coloring matter or pigment (carotenoid for example; flavonoid; cyanidin(e); chlorophyll and its derivative); seasonings and odor compound and synthetic; natural or be equal to natural seasonings and taste compound.
The activity of all other routines that is used for oral drug preparation, basis, auxiliary and additive materials can be as the components according to other oral pharmaceutical goods of the present invention.This activity, basis, auxiliary and additive materials can be transformed into oral dosage form by known way own.This by use be suitable for the inertia of pharmaceutical use, nontoxic auxiliary material is finished.Wherein these auxiliary materials comprise carrier (for example Microcrystalline Cellulose), solvent (for example liquid macrogol), emulsifying agent (for example sodium lauryl sulphate), disintegrating agent (for example polyvinylpyrrolidone), synthetic and natural biological polymer (for example albumin), stablizer (for example antioxidant for example xitix), tinting material (for example mineral dye for example ferric oxide) or smell correction agent and taste correction agent.
Article according to the invention preferably comprises flavour compositions to improve and to make with extra care the taste and/or the smell of these goods.Suitable flavour compositions comprises, and is for example synthetic, natural or be equal to natural flavour cpds and odor compound, but especially also comprises the material or the plant milk extract of other pungent taste and/or generation hotness.
Another aspect of the present invention relates to article according to the invention as half-finished purposes, is especially made the purpose of local flavor finished product by work in-process.
As half-finished article according to the invention comprise usually 0.0001wt%-95wt% based on the total formulation weight amount, preferred 0.001-80wt%, particularly 0.01wt%-50wt% according to alkoxyalkanoic acids acid amides of the present invention and choose any one kind of them or multiple other taste and flavour cpds, and comprise optional variety carrier and auxiliary substance or multiple solvent.
The finished product that specifically is preferably used as seasoning be contain the work in-process of alkoxyalkanoic acids acid amides used according to the invention (perhaps its mixture) and one or more have pungent taste and/or produce hotness and/or contain these materials plant milk extract combination or with the combination that causes tingle and/or other material of saliva stimulating excretory or contain the plant milk extract of these materials, also optional variety carrier and auxiliary substance and/or the multiple solvent of comprising of work in-process.
Embodiment
The preparation of alkoxyalkanoic acids acid amides
The preparation of embodiment 1 2-ethoxyacetic acid in heptan N-isobutyramide (6)
At first, isobutylamine (80.9g, 1.1mol) is joined in acetone (180ml) and the sodium hydroxide solution (45g/450ml water), and under nitrogen, measure the solution of 2-oxygen in heptan base Acetyl Chloride 98Min. (193.2g, 1mol) in acetone (180ml).Mixture stirs and spends the night, and adds 200g water, separating oil.Organic phase joins in the ethyl acetate and with normal hexane and precipitates.After-20 ℃ of crystallizations, with cooling Nutsch suction filter separated product (receive 62g, 25%, GC98.8 area %); Can from mother liquor, obtain other fraction of GC＞99%.
1H-NMR(CDCl
3，400MHz)：δ＝6.61(1H，bs，N-H)，3.93(2H，s，H-2)，3.50(2H，t，J＝6.6Hz，H-1′)，3.13(2H，dd，J＝6.5Hz，J＝6.4Hz，H-1″)，1.80(1H，m，J＝6.7Hz，H-2″)，1.61(2H，m，J?approx.6.5Hz，H-2′)，1.40-1.26(8H，m，H-3′-H-6′)，0.93(6H，d，J＝6.7Hz，H-3″)，0.89(3H，t，J＝7.0Hz，H-7′)ppm.
13C-NMR(CDCl
3，100MHz)：δ＝169.91(C，C-1)，71.90(CH
2，C-1′)，70.23(CH
2，C-2)，46.05(CH
2，C-1″)，31.77(CH
2，C-2″)，29.53(CH
2，C-2′)，29.06(CH
2)，28.54(CH，C-2″)，26.05(CH
2)，22.59(CH
2，C-6′)，20.08(2×CH
3，C-3″)，14.07(CH
3，C-6′)ppm.
MS(EI)：m/z＝28(23％)，29(28％)，41(44％)，43(40％)，44(27％)，57(100％)，60(76％)，72(22％)，115(92％)，229(＜1％，M
+).
The preparation of embodiment 2 2-ethoxyacetic acid in heptan N-(2-first butyl) acid amides (7)
At first, 2-methylbutylamine (2.11g, 24mmol) is joined in acetone (4ml) and the sodium hydroxide solution (1g/10ml water), and under nitrogen, measure the solution of 2-oxygen in heptan base Acetyl Chloride 98Min. (4.0g, 20mmol) in acetone (4ml).Mixture stirs and spends the night, and adds 20g water, the mixture ethyl acetate extraction.Concentrated fully by evaporation, obtain light yellow oily product (2.13g, 44% yield, GC96.1 area %).
1H-NMR(CDCl
3，400MHz)：δ＝6.61(1H，bs，N-H)，3.93(2H，s，H-2)，3.50(2H，t，J＝6.6Hz，H-1′)，3.24(1H，dt，J＝13.2Hz，J＝6.1Hz，H-1″)，3.12(1H，dtd，J＝13.2Hz，J＝7.0Hz，J＝6.3Hz，H-1″)，1.65-1.53(2H，m)，1.46-1.25(8H，m)，1.18(1H，m)，0.92(3H，t，J＝7.5Hz，H-4″)，0.91(3H，d，J＝6.7Hz，H-5″)，0.89(3H，t，J＝6.8Hz，H-7′)ppm.
13C-NMR(CDCl
3，100MHz)：δ＝169.90(C，C-1)，71.89(CH
2，C-1′)，70.26(CH
2，C-2)，44.32(CH
2，C-1″)，34.94(CH
2，C-2″)，31.79(CH
2，C-5′)，29.55(CH
2，C-2′)，29.09(CH
2，C-4′)，27.02(CH，C-3″)，26.08(CH
2，C-3′)，22.60(CH
2，C-6′)，17.15(CH
3，C-5″)，14.08(CH
3，C-6′)，11.28(CH
3，C-4″)ppm.
MS(EI)：m/z＝41(28％)，43(59％)，44(26％)，57(88％)，60(48％)，71(35％)，73(28％)，76(23％)，129(100％)，243(＜1％，M
+).
HRMS:C
14H
29O
2The theoretical value 243.2198 of N, experimental value 243.2185.
The preparation of embodiment 3 2-ethoxyacetic acid in heptan N-piperidines acid amides (8)
At first, piperidines (2.14g, 24mmol) is joined in acetone (4ml) and the sodium hydroxide solution (1g/10ml water), and under nitrogen, measure the solution of 2-oxygen in heptan base Acetyl Chloride 98Min. (4.0g, 20mmol) in acetone (4ml).Mixture stirs and spends the night, and adds 20g water, the mixture ethyl acetate extraction.Concentrated fully by evaporation, obtain light yellow oily product (2.03g, 42% yield, GC＞95 area %).
1H-NMR(CDCl
3，400MHz)：δ＝4.12(2H，s，H-2)，3.54(2H，t，J?approx.5.5Hz，H-2″，H-6″)，3.49(2H，t，J＝6.7Hz，H-1′)，3.44(2H，t，J?approx.5.5Hz，H-2″，H-6″)，1.69-1.52(8H，m)，1.38-1.26(6H，m)，0.88(3H，t，J＝6.9Hz，H-7′)ppm.
13C-NMR(CDCl
3，100MHz)：δ＝167.73(C，C-1)，71.50(CH
2，C-1′)，70.71(CH
2，C-2)，46.21(CH
2，C-2″/C-6″)，42.90(CH
2，C-2″/C-6″)，31.81(CH
2，C-5′)，29.65(CH
2，C-2′)，29.11(CH
2，C-4′)，26.53(CH
2，C-3″/C-5″)，26.06(CH
2，C-3′)，25.63(CH
2，C-3″/C-5″)，24.54(CH
2C-4″)，22.62(CH
2，C-6′)，14.09(CH
3，C-7′)ppm.
MS(EI)：m/z＝41(23％)，43(12％)，55(11％)，57(19％)，69(14％)，70(10％)，84(14％)，112(72％)，127(100％)，241(＜1％).
HRMS:C
14H
27O
2The theoretical value 241.2042 of N, experimental value 241.2021.
The preparation of embodiment 4 2-ethoxyacetic acid in heptan N-tetramethyleneimine acid amides (9)
At first, Pyrrolidine (2.03g, 28mmol) is joined in acetone (4ml) and the sodium hydroxide solution (1g/10ml water), and under nitrogen, measure the solution of 2-oxygen in heptan base Acetyl Chloride 98Min. (4.5g, 23mmol) in acetone (4ml).Mixture stirs and spends the night, and adds 20g water, the mixture ethyl acetate extraction.Concentrated fully by evaporation, obtain light yellow oily product (2.8g, 54% yield, GC＞95 area %).
The preparation of embodiment 5 3-heptane base propionic acid N-isobutyramides (10)
At first, isobutylamine (2.14g, 30mmol) is joined in acetone (4ml) and the sodium hydroxide solution (1g/10ml water), and under nitrogen, measure the solution of 2-oxygen in heptan base Acetyl Chloride 98Min. (4.0g, 20mmol) in acetone (4ml).Mixture stirs and spends the night, and adds 20g water, the mixture ethyl acetate extraction.Concentrated fully by evaporation, obtain light yellow oily product (1.83g, 40% yield, GC＞95 area %).
1H-NMR(CDCl
3，400MHz)：δ＝6.48(1H，bs，N-H)，3.66(2H，dd，J＝6.0Hz，J＝5.5Hz，H-3)，3.46(2H，t，J＝6.6Hz，H-1′)，3.08(2H，dd，J＝6.8Hz，J＝6.0Hz，H-1″)，2.47(2H，dd，J＝6.0Hz，J＝5.5Hz，H-2)，1.77(1H，m，J＝6.7Hz，H-2″)，1.58(2H，m，H-2′)，1.38-1.26(8H，m)，0.92(6H，d，6.7Hz)，0.89(3H，t，J＝7.0Hz，H-7′)ppm.
13C-NMR(CDCl
3，100MHz)：δ＝171.77(C，C-1)，71.38(CH
2，C-1′)，66.99(CH
2，C-3)，46.69(CH
2，C-1″)，37.14(CH
2，C-2)，31.67(CH
2，C-4′)，29.65(CH
2，C-2′)，28.47(CH，C-2″)，25.92(CH
2，C-3′)，22.61(CH
2，C-5′)，20.10(2×CH
3，C-3″)，14.09(CH
3，C-6′)ppm.
MS(EI)：m/z＝30(100％)，41(46％)，43(97％)，55(56％)，57(87％)，73(60％)，85(85％)，86(61％)，144(93％)，229(24％).
HRMS:C
13H
27O
2The theoretical value 229.2042 of N, experimental value 229.2029.
The preparation of embodiment 6 3-heptane base propionic acid N-(2-first butyl) acid amides (11)
At first, 2-methylbutylamine (2.18g, 30mmol) is joined in acetone (4ml) and the sodium hydroxide solution (1g/10ml water), and under nitrogen, measure the solution of 2-oxygen in heptan base Acetyl Chloride 98Min. (4.0g, 20mmol) in acetone (4ml).Mixture stirs and spends the night, and adds 20g water, the mixture ethyl acetate extraction.Concentrated fully by evaporation, obtain light yellow oily product (1.58g, 33% yield, GC＞95 area %).
1H-NMR(CDCl
3，400MHz)：δ＝6.45(1H，bs，N-H)，3.66(2H，dd，J＝6.0Hz，J＝5.5Hz，H-3)，3.46(2H，t，J＝6.6Hz，H-1′)，3.20(1H，dt，J＝13.3Hz，J＝6.0Hz，H-1″)，3.07(2H，ddd，J＝13.2Hz，J＝7.2Hz，J＝5.9Hz，H-1″)，2.47(2H，dd，J＝6.0Hz，J＝5.5Hz，H-2)，1.62-1.50(4H，m)，1.46-1.26(6H，m)，0.90(3H，t，7.5Hz，H-4″)，0.90(3H，d，J＝7.0Hz，H-5″)，0.89(3H，t，J＝6.8Hz，H-7′)ppm.
13C-NMR(CDCl
3，100MHz)：δ＝171.81(C，C-1)，71.39(CH
2，C-1′)，66.99(CH
2，C-3)，44.89(CH
2，C-1″)，37.14(CH
2，C-2)，34.85(CH，C-2″)，31.68(CH
2，C-4′)，29.65(CH
2，C-2′)，27.00(CH
2，C-3″)，25.91(CH
2，C-3′)，22.61(CH
2，C-5′)，17.17(CH
3，-5″)，14.03(CH
3，C-6′)，11.27(CH
3，C-4″)ppm.
MS(EI)：m/z＝30(82％)，43(100％)，55(43％)，71(40％)，73(46％)，84(31％)，85(64％)，86(46％)，158(59％)，243(14％，M
+).
HRMS:C
14H
29O
2The theoretical value 243.2198 of N, experimental value 243.2163.
The preparation of embodiment 7 3-heptane base propionic acid N-piperidines acid amides (12)
At first, piperidines (2.14g, 24mmol) is joined in acetone (4ml) and the sodium hydroxide solution (1g/10ml water), and under nitrogen, measure the solution of 2-oxygen in heptan base Acetyl Chloride 98Min. (4.0g, 20mmol) in acetone (4ml).Mixture stirs and spends the night, and adds 20g water, the mixture ethyl acetate extraction.Concentrated fully by evaporation, obtain light yellow oily product (1.72g, 36% yield, GC＞95 area %).
1H-NMR(CDCl
3，400MHz)：δ＝3.75(2H，t，J＝7.0Hz，H-3)，3.55(2H，dd，J＝6.0Hz，J＝5.5Hz，H-2″，H-6″)，3.44(2H，t，J＝6.7Hz，H-1′)，3.44(2H，dd，J＝6.0Hz，J＝5.5Hz，H-2″，H-6″)，1.69-1.52(8H，m)，1.38-1.26(6H，m)，0.88(3H，t，J＝6.9Hz，H-6′)ppm.
13C-NMR(CDCl
3，100MHz)：δ＝169.27(C，C-1)，71.35(CH
2，C-1′)，67.17(CH
2，C-3)，46.81(CH
2，C-2″/C-6″)，42.61(CH
2，C-2″/C-6″)，33.74(CH
2，C-2)，31.71(CH
2，C-4′)，29.69(CH
2，C-2′)，26.48(CH
2，C-3″/C-5″)，25.84(CH
2，C-3′)，25.57(CH
2，C-3″/C-5″)，24.58(CH
2C-4″)，22.63(CH
2，C-5′)，14.05(CH
3，C-6′)ppm.
MS(EI)：m/z＝41(28％)，43(33％)，55(23％)，56(21％)，69(28％)，84(61％)，112(73％)，141(52％)，156(100％)，241(3％，M
+).
HRMS:C
14H
27O
2The theoretical value 241.2042 of N, experimental value 241.2045.
The preparation of embodiment 8 3-heptane base propionic acid N-tetramethyleneimine acid amides (13)
At first, Pyrrolidine (2.03g, 24mmol) is joined in acetone (4ml) and the sodium hydroxide solution (1g/10ml water), and under nitrogen, measure the solution of 2-oxygen in heptan base Acetyl Chloride 98Min. (4.5g, 23mmol) in acetone (4ml).Mixture stirs and spends the night, and adds 20g water, the mixture ethyl acetate extraction.Concentrated fully by evaporation, obtain light yellow oily product (3.01g, 58% yield, GC＞91 area %).
1H-NMR(CDCl
3，400MHz)：δ＝3.77(2H，t，J＝6.8Hz，H-3?or?H-1′)，3.48-3.44(4H，m，H-1″，H-5″)，3.44(2H，t，J＝6.7Hz，H-3?or?H-1′)，2.56(2H，tt，J＝6.8Hz，J＝0.6Hz，H-2)，1.98-1.81(4H，m，H-2″，H-3″)，1.55(2H，m，H-2′)，1.36-1.24(6H，m，H-3′，H-4′，H-5′)，0.88(3H，t，J＝7.0Hz，H-6′)ppm.
MS(EI)：m/z＝41(18％)，43(48％)，55(41％)，56(23％)，70(60％)，71(20％)，98(78％)，127(50％)，142(100％)，227(3％，M
+).
The preparation of embodiment 9 2-heptane guanidine-acetic acid N-(4-hydroxyl-3-methoxybenzyl) acid amides (14)
At first, 4-hydroxyl-3-methoxybenzyl amine salt acid (1g, 5.3mmol) is joined in acetone (4ml) and the sodium hydroxide solution (1g/10ml water), and under nitrogen, measure the solution of 2-oxygen in heptan base Acetyl Chloride 98Min. (1g, 5.2mmol) in acetone (4ml).Mixture stirs and spends the night, and adds 20g water, the mixture ethyl acetate extraction.Concentrated fully by evaporation, obtain light yellow oily product (0.5g, about 30% yield, GC＞95 area %).
MS(HPLC-APCI+)：m/z＝310.15(20％[M+H]
+)，618.81(100％)，619.74(22％，[2M+H]
+).
The preparation of embodiment 10 3-heptane base propionic acid N-(4-hydroxyl-3-methoxybenzyl) acid amides (15)
At first, 4-hydroxyl-3-methoxybenzyl amine salt acid (1g, 5.3mmol) is joined in acetone (4ml) and the sodium hydroxide solution (1g/10ml water), and under nitrogen, measure the solution of 2-oxygen in heptan base Acetyl Chloride 98Min. (1g, 5.2mmol) in acetone (4ml).Mixture stirs and spends the night, and adds 20g water, the mixture ethyl acetate extraction.Concentrated fully by evaporation, obtain light yellow oily product (0.5g, about 30% yield, HPLC＞95 area %).
1H-NMR(CDCl
3，400MHz)：δ＝6.88(1H，d，J＝8.0Hz，H-5″)，6.82(1H，d，J＝2.0Hz，H-2″)，6.79(1H，ddd，J＝8.0Hz，1.9Hz，0.5Hz，H-6″)，5.67(1H，b，N-H？)，4.41(2H，d，J＝6.0Hz，H-7″)，3.97(2H，s，H-2)，3.88(3H，s，O-CH
3)，3.48(2H，t，J＝6.7Hz，H-1′)，1.56(2H，m，H-2′)，1.38-1.20(8H，m，H3′，H-4′，H-5′，H-6′)，0.87(3H，t，J＝7.1Hz，H-7′)ppm.
13C-NMR(CDCl
3，100MHz)：δ＝169.80(C，C-1)，146.69(C，C3″)，145.17(C，C-4″)，130.01(C，C-1″)，120.81(CH，C-6″)，114.41(C-5″)，110.64(C-2″)，71.93(CH
2，C-1′)，70.18(CH
2，C-2)，55.96(CH
3，O-CH
3)，42.78(CH
2，C-7″)，31.74(CH
2，C-5′)，29.44(CH
2，C-2′)，29.03(CH
2，C-4)，25.99(CH
2，C-3)，22.57(CH
2，C-6′)，14.06(CH
3，C-7′)ppm.
MS(HPLC-APCI+)：m/z＝310.02(50％，[M+H]
+)，618.62(100％)，619.68(23％，[2M+H]
+).
Application Example 1 sensory evaluation
Material to be tasted (as follows) is dissolved in the ethanol, then with ethanolic soln with 11% sugar soln (final concentration: c) dilution.In order to taste, swallow about 5ml sugar soln at every turn.If known above-mentioned substance threshold value, the value of then selecting just to surpass threshold value is used for tasting.One group of 6-8 name testee tastes solution.A) feature of 2-ethoxyacetic acid in heptan N-isobutyramide (embodiment 1, compound 6)
C=10ppm: salivary flow slowly increases, only at the tip of the tongue slight tingle arranged, than trans-pellitorine milder and not stronger;
B) feature of 3-oxygen in heptan base propionic acid N-isobutyramide (embodiment 5, compound 10)
C=10ppm: slobber, tingle, slight coolness
C) feature of 3-oxygen in heptan base propionic acid N-(4-hydroxyl-3-methoxybenzyl) acid amides (embodiment 10, compound 15)
C=10ppm: pungent, calcination, heat effect, be not very lasting, minimal irritation salivation.
The comparative example
D) feature of Dihydrocapsaicin
C=10ppb: effect slight delay generation in the pharyngeal cavity, intensive, the pungent sense of calcination (sending out cool, the slight heat that produces), lasting
E) 2E, the feature of 4E-decadienoic acid N-isobutyramide (trans-pellitorine)
C=10ppm: pungent, calcination, heat effect, be not very lasting, minimal irritation salivation.
Application Example 2 is as the seasonings in the toothpaste
| Part | Composition | Consumption wt% |
| A | Deionized water | 22.00 |
| Sorbyl alcohol (70%) | 45.00 | |
| Solbrol _M, sodium salt (Bayer AG, alkyl paraben) | 0.15 | |
| Tertiary sodium phosphate | 0.10 | |
| Asccharin, 450 times | 0.20 | |
| Sodium monoflurophosphate | 1.12 | |
| Polyethylene glycol 1500 | 5.00 | |
| B | Sident 9 (abrasive silica) | 10.00 |
| Sident 22S (thickening silica) | 8.00 | |
| Xylo-Mucine | 0.90 | |
| Titanium dioxide | 0.50 | |
| C | Deionized water | 4.53 |
| Sodium lauryl sulphate | 1.50 | |
| D | Seasonings contains 2-ethoxyacetic acid in heptan N-isobutyramide (embodiment 1) of 0.1% | 1 |
With the composition of part A and B premix and under vacuum, 25-30 ℃, fully stir 30min together separately separately.The pre-mixing portion C and join A and B in.Add D and the 30min that under vacuum, 25-30 ℃, fully stirs the mixture subsequently.After discharging vacuum, finish toothpaste and also can pack.
Sensation is described: clear feel the effect of saliva stimulating excretory but on the tongue without any tingle, but at the pharyngeal cavity rear portion slight tingle is arranged; Happy, do not have a persistent effect.
Application Example 3 is as the seasonings in the sugar-free chewing gum
| Part | Composition | Consumption wt.% |
| A | Chewing gum base, company " Jagum T " | 30.00 |
| B | Sorbyl alcohol, Powdered | 39.00 |
| Isomalt _(Palatinit?GmbH) | 9.50 | |
| Xylitol | 2.00 | |
| N.F,USP MANNITOL | 3.00 | |
| Aspartam _ | 0.10 | |
| Acesulfam _K | 0.10 | |
| Emulgum _(Colloides?Naturels.Inc.) | 0.30 | |
| C | Sorbyl alcohol, 70% | 14.00 |
| Glycerine | 1.00 | |
| D | Seasonings contains 2-ethoxyacetic acid in heptan N-isobutyramide (embodiment 1) of 0.1% | 1 |
Part A-D mixing is also thoroughly kneaded.Crude mixture can be processed into the chewing gum of promptly using form, for example thin bar shaped.
Application Example 4 is as the seasonings in the mouth wash shua
| Part | Composition | Content (%) |
| A | Ethanol | 10.00 |
| Cremophor _CO40 (BASF, sanitising agent) | 1.00 | |
| Phenylformic acid | 0.12 | |
| Seasonings contains 2-ethoxyacetic acid in heptan N-isobutyramide (embodiment 1) of 0.4% | 0.25 | |
| B | Deionized water | 83.46 |
| Sorbyl alcohol, 70% | 5.00 | |
| Soluble saccharin 450 | 0.07 | |
| L-Blue5000e.c., 1% (tinting material) in the water | 0.10 |
The composition of part A and B is mixed separately separately.Slowly part B is stirred and join in the part A up to mixing.
Application Example 5 is as the seasonings in the sugar-free hard candy fruit
| Composition | Content (%) |
| Palatinit, the M type | 75.10％ |
| Water | 24.82％ |
| The peppermint seasonings | 0.1％ |
| The ethanolic soln that contains 1% 3-hexyloxy propionic acid N-isobutyramide (embodiment 5) | 0.08％ |
Under 165 ℃, Palatinit is dissolved in the water, mixture is cooled to 115 ℃.Add seasonings and ethanolic soln, after thoroughly mixing, be filled in the mould mixture and indwelling.
Application Example 6 is as seasonings in the boiled sweet
| Composition | Content (%) |
| Sucrose | 57.00％ |
| Dextrose syrup | 29.00％ |
| Water | 13.82％ |
| The lemon seasonings | 0.1％ |
| The ethanolic soln that contains 1% 3-hexyloxy propionic acid N-isobutyramide (embodiment 5) | 0.08％ |
Under 115 ℃, sucrose dissolved in water, is added dextrose syrup and mixture temperature is brought up to 140 ℃.Add seasonings and ethanolic soln, after thoroughly mixing, under 130-135 ℃, be filled in the mould mixture and indwelling.
Application Example 7 is as the condiment in the crisp fritter snack of degree of depth frying
The mixture that 7g is used for 3-oxygen in the heptan base propionic acid N-isobutyramide (embodiment 5) of the cheese of snack seasoning and 0.07g is sprayed at the unforseen corn bar (tortilla chip) of 100g.
The purposes of Application Example 8 in the biscuit filling cream
3-oxygen in the heptan base propionic acid N-isobutyramide (embodiment 5) of the standard whipped filling of thorough mixing 100g and agent of 0.4g strawberry-flavoured and 0.1g.
Application Example 9 is as the flavor of the ethanol in calvados toughener
| Composition | Content |
| Ethanol 96 volume % | 14.90l |
| Seasonings (natural Sucus Mali pumilae Liquor seasonings, 15 volume %, contain 3-hexyloxy propionic acid N-(4-hydroxyl-3-methoxyphenyl) acid amides of 0.01wt.%, embodiment 10) | 5.2l |
| Syrup | 27kg |
| The citric acid monohydrate compound | 1kg |
| Add to 1001 with deionized water | Amount to 100l |
In order to prepare described toughener, mix all the components and in the end measure seasonings.
Application Example 10 is used as the ethanol simulant in no ethanol goods
| Composition | Content |
| 3-hexyloxy propionic acid N-(4-hydroxyl-3-methoxyphenyl) acid amides, embodiment 10 | 0.002g |
| Invert syrup 66.5% dry-matter | 20g |
| Tap water | 75.94g |
In order to prepare described simulant, mix all the components and in the end measure seasonings.
Claims (11)
1. the purposes of the alkoxyalkanoic acids acid amides of general formula (5a),
Wherein
N represents numeral 1 or 2
With
R
1Represent alkyl,
With
R
2The optional low carbon number alkyl that is substituted with one or more hydroxyls of representative,
Or
The purposes of the alkoxyalkanoic acids acid amides of general formula (5b),
Wherein
N represents numeral 1 or 2
With
R
1Represent alkyl,
With
M represents numeral 1 or 2
With
R ' and R " independently represent hydrogen atom or methyl or ethyl or represent methylene radical together respectively,
Or
The purposes of the alkoxyalkanoic acids acid amides of general formula (5c),
Wherein
N represents numeral 1 or 2
With
R
1Represent alkyl,
With
R
2And R
3The optional identical or different low carbon number alkyl that is substituted with one or more hydroxyls of independent respectively representative,
Or
R
2And R
3Form alkylidene group together,
Or the purposes of the mixture of general formula (5a), (5b) and/or two or more compounds (5c), as (i) seasonings and/or (ii) produce tingle and/or (iii) produce pungent sense and/or (iv) stimulate the oral cavity to salivation and/or (v) strengthen the alcoholic acid taste and/or (vi) simulate the alcoholic acid taste.
2. the purposes of claim 1 is used for the nutrition consumer's goods or abstract the recreational consumption product or oral hygiene products.
3. the purposes of claim 1 is used for the oral pharmaceutical goods.
4. nutrition consumer's goods, oral hygiene products or abstract the recreational consumption product comprise causing tingle and/or pungent sense and/or hotness and/or producing saliva stream and/or the alkoxyalkanoic acids acid amides of the general formula (5a) of reinforcement or simulation ethanol taste of significant quantity
Wherein
N represents numeral 1 or 2
With
R
1Represent alkyl,
With
R
2The optional low carbon number alkyl that is substituted with one or more hydroxyls of representative,
Or
The alkoxyalkanoic acids acid amides of general formula (5b),
Wherein
N represents numeral 1 or 2
With
R
1Represent alkyl,
With
M represents numeral 1 or 2
With
R ' and R " independently represent hydrogen atom or methyl or ethyl or represent methylene radical together respectively,
Or
The alkoxyalkanoic acids acid amides of general formula (5c)
Wherein
N represents numeral 1 or 2
With
R
1Represent alkyl,
With
R
2And R
3The optional identical or different low carbon number alkyl that is substituted with one or more hydroxyls of independent respectively representative,
Or
R
2And R
3Form alkylidene group together,
Or the mixture of general formula (5a), (5b) and/or two or more compounds (5c).
5. oral pharmaceutical goods comprise causing tingle and/or pungent sense and/or hotness and/or producing saliva stream and/or the alkoxyalkanoic acids acid amides of the general formula (5a) of reinforcement or simulation ethanol taste of significant quantity
Wherein
N represents numeral 1 or 2
With
R
1Represent alkyl,
With
R
2The optional low carbon number alkyl that is substituted with one or more hydroxyls of representative,
Or
The alkoxyalkanoic acids acid amides of general formula (5b),
Wherein
N represents numeral 1 or 2
With
R
1Represent alkyl,
With
M represents numeral 1 or 2
With
R ' and R " independently represent hydrogen atom or methyl or ethyl or represent methylene radical together respectively, or the mixture of general formula (5a) and/or two or more compounds (5b).
6. the goods in the claim 4 or 5 comprise the additional substances that one or more have pungent taste and/or produce hotness.
7. one goods among the claim 4-6 comprise one or more and cause tingle or saliva stimulating excretory additional substances.
8. one goods among the claim 4-7 comprise at least a material that causes the ice-cold effect of physiological.
9. one goods among the claim 4-8, it is the work in-process form.
10. at least one goods among the claim 4-9, it is smell, local flavor or taste composition or seasonings mixture.
11. the alkoxyalkanoic acids acid amides of a general formula (5a)
Wherein
N represents numeral 1 or 2
With
R
1Represent alkyl,
With
R
2The optional low carbon number alkyl that is substituted with one or more hydroxyls of representative,
Or
The alkoxyalkanoic acids acid amides of general formula (5b),
Wherein
N represents numeral 1 or 2
With
R
1Represent alkyl,
With
M represents numeral 1 or 2
With
R ' and R " independently represent hydrogen atom or methyl or ethyl or represent methylene radical together respectively.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004032878.1 | 2004-07-07 | ||
| DE102004032878A DE102004032878A1 (en) | 2004-07-07 | 2004-07-07 | Use of alkyloxyalkanoic acid amides, in particular as flavoring agents, and new alkyloxyalkanoic acid amides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1976895A true CN1976895A (en) | 2007-06-06 |
Family
ID=35134253
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA200580022147XA Pending CN1976895A (en) | 2004-07-07 | 2005-07-06 | Use of alkyloxyalcanic acid amides, in particular in the form of aromatic substances and a novel alkyloxyalcanic acid amide |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP1765772A1 (en) |
| JP (1) | JP2008505868A (en) |
| CN (1) | CN1976895A (en) |
| DE (1) | DE102004032878A1 (en) |
| WO (1) | WO2006003210A1 (en) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1886662B1 (en) | 2006-06-14 | 2014-04-09 | Symrise AG | Anti-microbial compounds for treating bad breath |
| EP2075320A1 (en) | 2007-12-17 | 2009-07-01 | Symrise GmbH & Co. KG | Method for manufacturing an aroma concentrate and aroma concentrate |
| JP5215839B2 (en) * | 2008-01-15 | 2013-06-19 | サッポロビール株式会社 | Sparkling alcoholic beverage and method for producing the same |
| CN102036571B (en) | 2008-05-20 | 2013-07-31 | 雀巢产品技术援助有限公司 | Acylamino acid compounds and food preparations containing same |
| FR2951447B1 (en) | 2009-10-19 | 2012-10-19 | Rhodia Operations | ETHER AMIDE COMPOUNDS AND USES THEREOF |
| US20110104080A1 (en) | 2009-11-03 | 2011-05-05 | David Salloum Salloum | Oral Compositions for Treatment of Dry Mouth |
| US20110104081A1 (en) | 2009-11-03 | 2011-05-05 | Douglas Craig Scott | Oral Compositions for Treatment of Dry Mouth |
| GB201001796D0 (en) * | 2010-02-04 | 2010-03-24 | Givaudan Sa | Compounds |
| JP2013195289A (en) | 2012-03-21 | 2013-09-30 | Takasago Internatl Corp | Method for evaluating sense stimulating component |
| ES2869275T3 (en) | 2015-04-24 | 2021-10-25 | Int Flavors & Fragrances Inc | Supply systems and preparation procedures |
| ES2950434T3 (en) | 2016-09-16 | 2023-10-10 | Int Flavors & Fragrances Inc | Microcapsule compositions stabilized with viscosity control agents |
| CN110168038B (en) | 2017-01-10 | 2022-05-27 | 高砂香料工业株式会社 | Methyl menthol derivative and cold sensate composition containing same |
| EP3699250A4 (en) | 2017-10-16 | 2021-08-25 | Takasago International Corporation | Cool-sensation imparter composition containing 2,2,6-trimethylcyclohexanecarboxylic acid derivative |
| CN112566507A (en) | 2018-08-17 | 2021-03-26 | 西姆莱斯有限公司 | Obtaining volatile fraction from fruit and vegetable juice or alcoholic beverage |
| CN117202986A (en) | 2021-04-16 | 2023-12-08 | 国际香精香料公司 | Hydrogel encapsulation and method for producing same |
| WO2024026225A1 (en) | 2022-07-26 | 2024-02-01 | International Flavors & Fragrances Inc. | Robust flavor emulsions |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2704280A (en) * | 1951-05-29 | 1955-03-15 | Colgate Palmolive Co | Long-chain aliphatic ether-amides in detergent compositions |
| GB723946A (en) * | 1951-09-21 | 1955-02-16 | Geigy Ag J R | Improvements in and relating to derivatives of 3-(4-hydroxyphenyl)-3-(4-hydroxy-methyl-phenyl)-oxindole |
| DE1027460B (en) * | 1955-05-05 | 1958-04-03 | Geigy Ag J R | Fight against fungi and bacteria |
| CH411221A (en) * | 1960-12-23 | 1966-04-15 | Geigy Ag J R | Process for the production of spun-dyed, regenerated cellulose fibers |
| DE10226942A1 (en) * | 2002-06-17 | 2003-12-24 | Symrise Gmbh & Co Kg | Use of mandelic acid alkyl amides as flavorings |
| DE10253331A1 (en) * | 2002-11-14 | 2004-06-03 | Symrise Gmbh & Co. Kg | Use of trans-pellitori as a flavoring |
-
2004
- 2004-07-07 DE DE102004032878A patent/DE102004032878A1/en not_active Withdrawn
-
2005
- 2005-07-06 WO PCT/EP2005/053228 patent/WO2006003210A1/en not_active Application Discontinuation
- 2005-07-06 EP EP05774185A patent/EP1765772A1/en not_active Withdrawn
- 2005-07-06 CN CNA200580022147XA patent/CN1976895A/en active Pending
- 2005-07-06 JP JP2007519797A patent/JP2008505868A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JP2008505868A (en) | 2008-02-28 |
| DE102004032878A1 (en) | 2006-02-16 |
| WO2006003210A1 (en) | 2006-01-12 |
| EP1765772A1 (en) | 2007-03-28 |
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