CN101184744A

CN101184744A - Michael addition product and schiff's base aromachemicals

Info

Publication number: CN101184744A
Application number: CNA2006800072978A
Authority: CN
Inventors: 卢卡·图莱
Original assignee: Flexitral Inc
Current assignee: Flexitral Inc
Priority date: 2005-02-09
Filing date: 2006-01-20
Publication date: 2008-05-21
Also published as: ZA200707529B; ZA200707528B; CN101184743A

Abstract

A pro-odorant or pro-flavorant that is liquid at room temperature and has a relatively low viscosity and has the formula (I): wherein R<1> is H, an aliphatic group or an aromatic group, R<2> is an aliphatic group or an aromatic group, provided that the total number of carbon atoms in the groups R<1> and R<2> is 10 or more; R<5> is CN, COOH, COOR<7>, CHO or C(O)R<8>; R<3>, R<4> and R<6> are each independently hydrogen or organic moieties which together with R<5> render a compound of formula R<5>R<6>C=CR<3>R<4> a material having odorant or flavourant characteristics and R<7> and R<8> are each independently an organic moiety; or the formula (II): R<9>R<10>C=NR<11> wherein R<11> has at least 10 carbon atoms and is an aliphatic group or an aromatic group; R<9> and R<10> are each independently H or organic moieties which together with C=O render a compound of formula : R<9>R<10>C=O a material having odorant or flavourant characteristics, provided that only one of R<9> and R<10> is hydrogen; or the formula (III): wherein R<1> is H, an aliphatic group or an aromatic group, R<2> is an aliphatic group or an aromatic group, provided that the total number of carbon atoms in the groups R<1> and R<2> is 10 or more; Z is CH2 or O, n is 0 or 1, such that the ring is a 5 or 6 membered ring, R<12> is H, alkyl or alkenyl or alkoxy having up to 10 carbon atoms so as to render a compound of formula (V): a material having odorant or flavorant characteristics; or formula (IV): wherein R<11> has at least 10 carbon atoms and is an aliphatic group or an aromatic group; the or each R<13> is independently a straight or branched chain, saturated or unsaturated hydrocarbyl group or alkoxy group having from 1 to 8 carbon atoms or two groups R<13> together with the carbon atoms to which they are attached form a five or six membered ring which may be saturated or unsaturated (including aromatic) and which may be optionally substituted with from 1 to 3 alkyl groups having from 1 to 6 carbon atoms.

Description

Fragrance precursor and flavour precursors composition

Technical field

The present invention relates generally to the field of spices (fragrances) and condiment (flavorants).More specifically, the present invention relates to discharge enduringly the novel fragrance precursor (pro-fragrance) and the flavour precursors (pro-flavorant) of fragrance (fragrance) and local flavor (flavor) feature, and relate to their application in different matrix as spices (fragrance) and condiment (flavor) composition.

Background technology

Send out product, composition and the finished product of fragrant and seasoning and know in the art, and be widely used.Yet the human consumer depends mainly on this product keeps and discharge its fragrance (fragrance) and/or local flavor (flavor) in for some time ability to the acceptability of these products.The current problem of fabric nursing circle is that some essence (perfume) component is difficult to keep their fragrance characteristic in acceptable for some time.Essence additive generally comprises in fabric detergent, bleaching composition and fabric softening agent.Yet these essence promptly are lost in the environment of handling fabric usually, for example, and in the washing water of washing machine and the wash-down water circulation, and in the dry recycle of clothes-drying machine, and only have a little to give or remained on the fabric of accepting to handle.The transmission deficiency of expensive perfume ingredient causes high cost to the producers and consumers in fabric treating, and for the human consumer acceptability of these products is caused bad influence.

Prolongation spices and seasoning composition discharge the performance of fragrance and local flavor in for some time expectation also is present in other industry and the purposes.For example, if can increase the spices (fragrance) in the product and the persistence of condiment (flavor) component, can increase the acceptability of human consumer greatly, and reduce their cost significantly various products.These products comprise food, personal care product, household and industrial cleaning compositions, sterilizing agent, beverage, chewing gum, medical composition (pharmaceutical andmedicinal composition) and oral matrix (orally-deliverable matrices).

In order to improve especially " lastingly " property of fragrance in fabric nursing industry, various effort have been made.

U.S. Patent number 5,188,753 illustrative examples are as the carrier mechanism of sealing, and it is not proved to be success yet.

Other scheme comprises the preparation of the reaction product that relates to essence and reactant, when prepared product (fragrance precursor) ratio uses spices separately, delays to discharge fragrance in the longer time.See U.S. Patent Application Publication No. 20030211963,20030211960,20030134772,20030073607,20050043205,20050009727,20040147426,20040116320,20040097397,20040018955 and U.S. Patent number 6,858,575; 6,790,815; 6,764,986; 6,740,713; 6,699,823; 6,566,312; 6,511,948; 6,451,751 and 6,413,920.Although obtained having fragrance precursor combination of features thing, the reaction product that flavor compounds of mentioning in above-mentioned patent and the open file and reactant reaction obtain is a solid, or comprises the high fluid of viscosity.

Formerly technical field once proposed to form the Schiff alkali of aldehyde formula flavor compounds (or aromachemicals).Yet, in these situations, utilize the volatile amine of o-amino benzoyl acid alkyl ester for example etc., when the Schiff alkaline degradation, their add the smell (unpleasant sometimes) of itself in environment, and the fragrance characteristic to aromachemicals causes bad influence thus.

The enumerating or discussing of open file formerly in this specification sheets should be used as and be to recognize that this document is a part or the general common practise of this area situation.

Summary of the invention

The object of the present invention is to provide novel fragrance precursor and flavour precursors composition, its viscosity that has is starkly lower than prior art.

The invention provides the smell precursor and the flavour precursors of novel formula (I), it at room temperature is liquid and has than low viscosity:

R wherein ¹Be H, aliphatic group or aromatic group, R ²Be aliphatic group or aromatic group, condition is R ¹And R ²Carbon atom adds up to 10 or more in the group; R ⁵Be CN, COOH, COOR ⁷, CHO or C (O) R ⁸R ³, R ⁴And R ⁶Independent separately is hydrogen or organic group (organicmoieties), itself and R ⁵The formula that provides in the lump is R ⁵R ⁶C=CR ³R ⁴Compound, described compound is for having smell or flavour characteristic material, and R ⁷And R ⁸Independent separately is organic group.

R ³, R ⁴And R ⁶Group can be for example H, straight or branched or cyclic C _1-12Alkyl, thiazolinyl or alkoxyl group; The straight or branched that replaces or cyclic C _1-12Alkyl, thiazolinyl or alkoxyl group; Replace or unsubstituted aryl, halogen, hydroxyl, mercaptan, thioether, amine, carboxylic acid, ester, nitro, cyano group, isocyano-, sulfonic acid, urea and thiocarbamide.Suitable substituents on the alkyl, thiazolinyl, alkoxyl group or the aryl that replace comprises halogen, hydroxyl, mercaptan, thioether, amine, carboxylic acid, ester, nitro, cyano group, isocyano-, sulfonic acid, urea and thiocarbamide.

R ⁷And R ⁸Preferred is the C of straight or branched independently separately _1-12Alkyl or alkenyl; The C of the straight or branched that replaces _1-12Alkyl or alkenyl; Replace or unsubstituted aryl, halogen, hydroxyl, mercaptan, thioether, amine, carboxylic acid, ester, nitro, cyano group, isocyano-, sulfonic acid, urea and thiocarbamide.Suitable substituents on the alkyl, thiazolinyl, alkoxyl group or the aryl that replace comprises halogen, hydroxyl, mercaptan, thioether, amine, carboxylic acid, ester, nitro, cyano group, isocyano-, sulfonic acid, urea and thiocarbamide.

Preferred R ⁴And R ⁶In at least one be H, for example R ⁴And R ⁶The both is H.R ⁶Another preferred group be cyclohexyl.

In one aspect of the invention, R ¹Be H, alkyl, thiazolinyl or alkoxyl group, R ²Be alkyl, thiazolinyl or alkoxyl group, condition is R ¹And R ²In the group carbon atom add up to 10 or more, be preferably 12～25 carbon atoms, for example 15～20 carbon atoms, for example 18 carbon atoms.Alkyl, thiazolinyl or alkoxyl group can be straight chain or side chain or cyclic.Preferred R ¹Be H.Alternatively, R ¹And R ²In at least one be aryl.

The compound of particularly preferred formula (I) comprising:

With

The present invention also provides the smell precursor or the flavour precursors of formula (II), and it at room temperature is liquid and has than low viscosity:

R ⁹R ¹⁰C＝NR ¹¹

R wherein ¹¹Be aliphatic group or aromatic group with at least 10 carbon atoms; R ⁹And R ¹⁰Independent separately is hydrogen or organic group, and it is R that itself and C=O provide formula in the lump ⁹R ¹⁰The compound of C=O, it is for having smell or flavour characteristic material, and condition is R ⁹And R ¹⁰In have only one for hydrogen.

R ⁹And R ¹⁰Group can for example be H, straight or branched or cyclic C _1-12Alkyl, thiazolinyl or alkoxyl group; The straight or branched that replaces or cyclic C _1-12Alkyl, thiazolinyl or alkoxyl group; Replace or unsubstituted aryl, halogen, hydroxyl, mercaptan, thioether, amine, carboxylic acid, ester, nitro, cyano group, isocyano-, sulfonic acid, urea and thiocarbamide.Suitable substituents on the alkyl, thiazolinyl, alkoxyl group or the aryl that replace comprises aryl, halogen, hydroxyl, mercaptan, thioether, amine, carboxylic acid, ester, nitro, cyano group, isocyano-, sulfonic acid, urea and thiocarbamide.

R ⁹And R ¹⁰Preferred independent separately be hydrogen, straight or branched or cyclic C _1-12Alkyl, thiazolinyl or alkoxyl group; The C of the straight or branched that replaces _1-12Alkyl, thiazolinyl or alkoxyl group; Replace or unsubstituted aryl, the more preferably C of straight or branched _1-6Alkyl or alkenyl.R for example ⁹Can be the alkyl that comprises four carbon atom, for example-CH (CH ₃) CH ₂CH ₃, maybe can comprise aryl, for example be CH ₂CH (CH ₃) (C ₆H ₅).R for example ¹⁰Can be hydrogen or methyl.

In aspect this one, R ¹¹Have at least 10 carbon atoms, and be alkyl, thiazolinyl or alkoxyl group, preferred 12～25 carbon atoms, for example 15～20 carbon atoms, for example 18 carbon atoms.Alkyl, thiazolinyl or alkoxyl group can be straight chain or side chain.

The compound of preferred formula (II) is:

The present invention also provides the smell precursor or the flavour precursors of formula (III), and it at room temperature is liquid and has than low viscosity:

R wherein ¹Be H, aliphatic group or aromatic group, R ²Be aliphatic group or aromatic group, condition is R ¹And R ²Carbon atom adds up to 10 or more in the group; Z is CH ₂Or O, n is 0 or 1, therefore ring is 5 yuan of rings or 6 yuan of rings; R ¹²For having alkyl or alkenyl or the alkoxyl group that mostly is 10 carbon atoms most, obtain following formula: compound thus:

Described compound is for having smell or flavour characteristic material.

In aspect this one, R ¹Be H, alkyl, thiazolinyl or alkoxyl group, R ²Be alkyl, thiazolinyl or alkoxyl group, condition is R ¹And R ²Carbon atom adds up to 10 or more, preferred 12～25 carbon atoms, for example 15～20 carbon atoms, for example 18 carbon atoms in the group.Alkyl, thiazolinyl or alkoxyl group can be straight or brancheds.More preferably R ¹Be H.Alternatively, R ¹And R ²In at least one be aryl.

R ¹²Can be alkyl or alkenyl straight chain or side chain or alkoxyl group.Randomly, R ¹²Can replace.Suitable substituents comprises halogen, hydroxyl, mercaptan, thioether, amine, carboxylic acid, ester, nitro, cyano group, isocyano-, sulfonic acid, urea and thiocarbamide.

Preferred Z is that O and/or n are the compound of 0 formula (III).

Particularly preferred formula (III) compound comprises:

?

With with

?

With with

With

Particularly

The present invention also provides the smell precursor or the flavour precursors of formula (IV), and it at room temperature is liquid and has than low viscosity:

R wherein ¹¹Have at least 10 carbon atoms, and be aliphatic group or aromatic group; R ¹³Independent of separately having the straight or branched of 1～8 carbon atom, saturated or undersaturated alkyl or alkoxyl group or two R ¹³It can be saturated or undersaturated 5 yuan of rings or 6 yuan of rings (comprising aromatic ring) that group forms with the carbon atom with its connection, and described ring can be chosen wantonly by 1～3 alkyl replacement with 1～6 carbon atom; And x is 1～5, obtains following formula: compound thus:

Described compound is for having smell or flavour characteristic material.

Preferred R ¹³In at least one is alkyl, thiazolinyl or alkoxyl group, or two R ¹³Group forms 5 yuan of rings or 6 yuan of rings with the carbon atom with its connection.By two R ¹³The substituting group of group on the ring that the carbon atom with its connection forms preferably has 1～4 carbon atom.For example, at least one R ¹³Be alkyl, thiazolinyl or alkoxyl group, it is a straight or branched, and has 1～4 carbon atom.Particularly, at least one R ¹³Be the tertiary butyl and/or methoxyl group.One preferred aspect in, mostly be 3 R most ¹³Group can be the tertiary butyl and randomly one or more R ¹³Group can be a methoxyl group.

Preferred formula (IV) compound is:

As used herein, " smell precursor " or " flavour precursors " mean those itself does not have smell or local flavor but can be in time and/or degraded obtains the molecule of scent of or local flavor under certain conditions compound basically, this compound is based on this molecule, and therefore obtains the smell or the local flavor of these base molecule (basemolecule).

Formula of the present invention (I) compound can become 1 by having with the aldehydes or ketones group, and the aromachemicals of 4-conjugated carbon-carbon double bond (for example being alpha, beta-unsaturated ketone) makes with the Michael addition reaction of primary amine or secondary amine.The aromachemicals that is applicable to this reaction has following formula V:

R wherein ³, R ⁴, R ⁵And R ⁶Separately as above-mentioned definition.

Used amine has formula in this reaction:

NHR ¹R ²

R wherein ¹And R ²As above-mentioned definition.

General reaction scheme is as follows:

The compound of the prepared in reaction formula of the present invention (II) of the imines of the formula (II) that aromachemicals that can be by having at least one aldehydes or ketones group and primary amine form.

The aldehyde and the ketone that can use in this reaction have following formula (VI):

R ⁹R ¹⁰C＝O

R wherein ⁹And R ¹⁰As above-mentioned definition.

The amine that can use in this reaction has formula: NH ₂R ¹¹, R wherein ¹¹As above-mentioned definition.

Use the general reaction scheme of primary amine (product is called azomethine, Schiff alkali or more preferably is called imines) as follows:

Formula of the present invention (III) compound can make by primary amine or secondary amine and the Michael addition reaction of alpha, beta-unsaturated ketone with aromachemicals/condiment feature of following formula (VII):

Wherein Z is CH ₂Or O, n is 0 or 1, therefore ring is respectively 5 yuan of rings or 6 yuan of rings, and R ¹²As above-mentioned definition.

Used amine has formula in this reaction: NHR ¹R ², R wherein ¹And R ²As above-mentioned definition.

General reaction scheme is as follows:

The compound of the prepared in reaction formula of the present invention (IV) of the imines of the formula (IV) that aromachemicals that can be by having at least one aldehyde group and primary amine form.

The aldehyde that can use in this reaction has following formula (VIII):

R wherein ¹³With x as above-mentioned definition.

For example, the compound of following formula:

Can be by compound (2,4-di-t-butyl-5-methoxybenzaldehyde) and the H that makes following formula ₂N (CH ₂) ₈CH=CH (CH ₂) ₇CH ₃The reaction and make:

By these simple, known and conventional methods, can make the compound and the composition that comprise The compounds of this invention.The reaction conditions and the parameter of carrying out these operations are that formerly technology is known, although may depend on the reactant that uses in order to the requirement in the special reaction that obtains optimum in each situation.

Usually use with the equimolal perfume ingredient of amine compound (being the compound of formula V, formula (VI), formula (VII) or formula (VII)) reaction is taken place, to obtain final amine reaction product.Certainly, do not get rid of the higher amount of use, and when amine compound comprises more than an amine functional group, higher amount or even preferred.When amine compound has more than a free primary amine and/or secondary amine functional groups, many different essence starting material can be attached to this amine compound.

The general odor intensity index of amine compound that the present invention uses is lower than the dipropylene glycol solution of 1% methyl cinnamyl o-aminobenzoate, and does surperficial foul smell index greater than 5.

In order to measure odor intensity index, in dipropylene glycol (nothing of using is smelt solvent), pure compound is diluted to 1% in spices manufacturing field.This per-cent is more representative usage level.To hear fragrant bar or so-called " Wen Xiangzhi " dipping and show, to estimate to jury of experts.Jury of experts is the grading person who has accepted relevant smell grading training at least six months, and given rank and the object of reference under the current system are being tested aspect accuracy and the reproducibility.For each amine compound, will show two Wen Xiangzhi to jury: belong to object of reference methyl cinnamyl o-aminobenzoate and sample respectively.Require jury to hear fragrant bar to two and grade under 0～5 odor strength grade, 0 for not recording smell, and 5 for having very intensive smell.

Be applicable to this reaction with the amine for preparing compound of the present invention be preferably vapour pressure is low relatively and molecular weight is high relatively non-fragrance (non-fragrant), do not have smell, non-volatile amine, promptly comprise aromatic series or fatty amine more than about 10 carbon atoms.The molecular weight of amine is at least 150 dalton preferably.

Can be used for that the nothing that suitable amine of the present invention comprises the primary amine that contains at least a free unmodified and/or secondary amine group is smelt, the aliphatics or the aromatic amine of low-steam pressure.Any suitable alkyl, thiazolinyl or the alkoxyl group, amine side chain or straight chain that can be used for the present invention's practice have at least about 10 carbon atoms, and it does not relatively have smells, and form relatively undissolved derivative with aromachemicals, and it has than low viscosity.Suitable amine comprises, but be not limited to, the n-amino dodecane, the n-tetradecy lamine, the n-cetylamine, the n-stearylamine, oleyl amine, cocoa alkylamine (cocoalkylamines), soybean alkylamine (soyaalkylamines), tallow alkylamine (tallowalkylamines), hydrogenated tallow alkyl amine, two-n-hexylamine, two-n-octylame, two-n-decyl amine, two-n-amino dodecane, two-n-tetradecy lamine, two-n-cetylamine, two-n-stearylamine, two oleyl amines, two cocoa alkylamines, two soybean alkylamines, two tallow alkylamine, two (hydrogenated tallow alkyl) amine, mix secondary amine, such as n-dodecyl methylamine, n-tetradecyl methylamine, n-hexadecyl methylamine, n-octadecyl methylamine, the oleyl methylamine, cocoa alkyl methylamine, soybean alkyl methylamine, the tallow alkyl methylamine, the hydrogenated tallow alkyl methylamine, n-decyl ethamine, n-dodecyl ethamine, n-tetradecyl ethamine, n-hexadecyl ethamine, n-octadecyl ethamine, oleyl ethamine, cocoa alkyl ethamine, soybean alkyl ethamine, tallow alkyl ethamine, hydrogenated tallow alkyl ethamine, its branched chain isomer and/or its derivative with and composition thereof.

For " primary amine and/or secondary amine ", mean the component that has at least one primary amine and/or secondary amine and/or amide group.

" Perfume and Flavor Chemicals ", Vol.I﹠amp; II, S.Arctander, AlluredPublishing, 1994, ISBN0-931710-35-5 has put down in writing and generally has been applied in ketone and the aldehyde that spices is made the field and generally is used as food flavouring, and it is applicable to the ketone and the aldehyde of preparation compound of the present invention.

The suitable ketone and aldehyde aromachemicals, spices or the condiment that can be used for preparing the present composition mainly comprise ketone known in the art and aldehyde aromachemicals, spices or condiment.Can be used for preparing the suitable ketone and the aldehyde aromachemicals of The compounds of this invention; the example of spices or condiment comprises; but be not limited to; buccoxime; isojasmone; β-Nai Yitong; the Moschus indone; tonalide/Moschus (tonalid/musk plus); α-damascone; β-damascone; δ-damascone; different damascone; trans-Damascenone; big horse rose ketone (damarose); the dihydro methyl jasmonate; piperitone; Karvon; camphor; fenchone; α-Zi Luotong; β-ionone; γ-methyl ionone (gamma-methylso-called Ionone); 2-n-heptyl cyclopentanone (fleuramone); Dihydrojasmone; suitable-jasmone; ambrotone (iso-E-super); methyl cypress ketenes (methyl-cedrenyl-ketone or methyl-cedrylone); methyl phenyl ketone; methyl acetophenone; p-methoxy-acetophenone; β-Nai Yitong; benzyl acetone; benzophenone; p-hydroxyphenyl butanone; apione (celery ketone or livescone); 6-sec.-propyl decahydro-2-naphthalenone; the dimethyl-octa ketenes; bright piperitone (freskomenthe); 4-(1-vinyl ethyl ether base)-3; 3; 5; 5-tetramethyl-ring hexanone; Sulcatone; 2-(2-(4-methyl-3-tetrahydrobenzene-1-yl) propyl group) cyclopentanone; 1-(right-menthene-6 (2)-yl)-1-acetone; 4-(4-hydroxy 3-methoxybenzene base)-2-butanone; 2-ethanoyl-3; 3-dimethyl norcamphane; 6; 7-dihydro-1; 1; 2; 3; 3-pentamethyl--4 (5H)-indone; 4-Tujue alcohol (4-damascol); piperonylacetone (dulcinyl or cassione); 2-hexyl methyl aceto acetate (gelsone); allyl group ionone (hexalon); isocyclemone E; trimethylcyclohexyl ketone (methyl cyclocitrone); methyl lavender ketone (methyl-lavender-ketone); orivone (orivon); to tertiary butyl pimelinketone; 2-tertiary butyl pimelinketone (verdone); 2 n hexyl cyclopentanone (delphone); muskone; new methylene acetone; medicine ketone musk (plicatone); 2-tertiary butyl pimelinketone (verdone); 2; 4; 4; 7-tetramethyl-oct-6-ene-3-ketone; 3; 4; 5; the false ionone of 6-tetrahydrochysene (tetrameran); A Daoke aldehyde (adoxal); aubepine; 3-(4-isopropyl phenyl) butyraldehyde (cymal); vanirone; cyanine aldehyde; helional; piperonylaldehyde; laurine; koavone; lauryl aldehyde; LYRAL (lyral); methyl nonyl acetaldehyde; phenylpropyl aldehyde (P.T.bucinal); phenyl acetaldehyde; undecylene aldehyde; Vanillin; 2; 6; 10-trimethylammonium-9-undecylene aldehyde; 3-laurylene-1-aldehyde; α-n-pentyl phenylacrolein; the 4-methoxybenzaldehyde; phenyl aldehyde; 3-(4-trimethylphenylmethane base) propionic aldehyde; 2-methyl-3-(p-methoxyphenyl) propionic aldehyde; 2-methyl-4-(2; 6; 6-trimethylammonium-2 (1)-tetrahydrobenzene-1-yl) butyraldehyde; 3-phenyl-2-propenal; suitable/anti--3; 7-dimethyl-2; 6-octadiene-1-aldehyde; 3; 7-dimethyl-6-octene-1-aldehyde; [(3; 7-dimethyl-6-octenyl) oxygen base] acetaldehyde; 4-isopropyl benzene formaldehyde; 1; 2; 3; 4; 5; 6; 7; 8-octahydro-8,8-dimethyl-2-naphthaldehyde; 2,4-dimethyl-3-tetrahydrobenzene-1-formaldehyde; 2-methyl-3-(isopropyl phenyl) propionic aldehyde; 1-capraldehyde (1-decanal); capraldehyde (decyl aldehyde); 2; 6-dimethyl-5-heptenal; ([5.2.1.0 (2 for three rings for 4-; 6)]-and Ya decyl-8) butyraldehyde; octahydro-4,7-methylene radical-1H-indenes formaldehyde; vanirom; to ethyl-α, the alpha-alpha-dimethyl hydrocinnamic aldehyde; Alpha-Methyl-3; 4-(methylene radical dioxy base) hydrocinnamic aldehyde; 3; 4-methylenedioxyphenyl formaldehyde; α-n-hexyl phenylacrolein; m-isopropyl benzene-7-formaldehyde; Alpha-Methyl phenyl acetaldehyde; 7-hydroxyl-3,7-dimethyl octanal; undecylene aldehyde; 2,4; 6-trimethylammonium-3-tetrahydrobenzene-1-formaldehyde; 4-(3) (4-methyl-3-pentenyl)-3-tetrahydrobenzene formaldehyde; the 1-lauric aldehyde; 2; the 4-triplal; 4-(4-hydroxy-4-methyl phenyl)-3-tetrahydrobenzene-1-formaldehyde; 7-methoxyl group-3,7-dimethyl-octa-1-aldehyde; the 2-methyl undecyl aldehyde; 2-methyl capraldehyde; the 1-aldehyde C-9; the 1-octanal; 2,6; 10-trimethylammonium-5; 9-11 olefine aldehydrs; 2-methyl-3-(the 4-tertiary butyl) propionic aldehyde; the dihydro phenylacrolein; 1-methyl-4-(4-methyl-3-pentenyl)-3-tetrahydrobenzene-1-formaldehyde; 5 or 6 methoxyl group six hydrogen-4,7-methylene radical alkane indane-1 or 2-formaldehyde; 3,7-dimethyl-octa-1-aldehyde; the 1-undecyl aldehyde; 10-hendecene-1-aldehyde; 4-hydroxy 3-methoxybenzene formaldehyde; 1-methyl-3-(4-aminomethyl phenyl)-3-tetrahydrobenzene formaldehyde; 7-hydroxyl-3; 7-dimethyl octanal; instead-the 4-decenal; 2; the 6-nonadienal; p-tolyl acetaldehyde; 4-aminomethyl phenyl acetaldehyde; 2-methyl-4-(2,6,6-trimethylammonium-1-tetrahydrobenzene-1-yl)-crotonic aldehyde; o-methoxy cinnamic aldehyde; 3; 5; 6-trimethylammonium-3-tetrahydrobenzene formaldehyde; 3,7-dimethyl-2-methylene radical-6-octenal; phenoxy acetaldehyde; 5,9-dimethyl-4; the 8-decadienal; tree peony aldehyde (6; 10-dimethyl-3-oxa--5,9-11 diene-1-aldehyde); six hydrogen-4,7-methylene radical indane-1-formaldehyde; 2 methyl octylaldehyde; Alpha-Methyl-4-(1-methylethyl) phenylacetic aldehyde; 6; firpene-2-propionic aldehyde falls in 6-dimethyl-2-; to the methylenedioxy phenoxy ethylhexanal; 2-methyl-3-phenyl-2-propylene-1-aldehyde; 3; 5,5-trimethylammonium hexanal; six hydrogen-8,8-dimethyl-2-naphthaldehyde; 3-propyl group-dicyclo [2.2.1] heptan-5-alkene-2-formaldehyde; the 9-decenal; 3-methyl-5-phenyl-1-valeral; methyl nonyl acetaldehyde; hexanal; instead-the 2-hexenoic aldehyde; 1-is to methylene-q-formaldehyde; 2-methyl-2-(p-isopropyl phenyl) propionic aldehyde; 1-(2; 6,6-trimethylammonium-2-hexamethylene-1-yl)-2-butylene-1-ketone and/or p-methoxy-acetophenone; undecylene aldehyde; γ-Shi Yineizhi; piperonylaldehyde; γ-dodecalactone; right-aubepine; the p-hydroxybenzene butanone; 3-(4-isopropyl phenyl) butyraldehyde (cymal); α-Zi Luotong; trans-Damascenone; β-ionone; methyl nonyl ketone; compound with following formula:

R wherein ¹⁴And R ¹⁵Independent is H or straight or branched alkyl or alkenyl or the alkoxyl group with 1～6 carbon atom, or their mixture.

According to the present invention, be applicable to that the deutero-aldehydic musks comprises fragrant Moschus (benzene formula Moschus (benzenic)) and polycyclic musk.The benzene formula Moschus that the present invention is suitable for comprises 2,4-di-t-butyl-5-methoxybenzaldehyde.As 2 of the example of benzene formula Moschus, 4-di-t-butyl-5-methoxybenzaldehyde, it has following structure:

Suitable polycyclic musk has following structure:

Wherein, R ¹⁶And R ¹⁷Can be identical or different, and it is straight or branched, saturated or unsaturated alkyl; Be preferably alkyl or alkenyl, and m is 1～4 and n is 1～6 with 1～8 carbon atom.

This polycyclic musk generally has following structure:

The example that can be used for preparing unsaturated aromachemicals, spices and the condiment of The compounds of this invention comprises 4-methylpent-2-alcohol crotonate, 1-cyclohexyl ethyl crotonate (Datilat) and hexyl crotonate; The pentenoic acid butyl ester; The pentenoic acid ethyl ester; Return sour own ester; The own ester of pentenoic acid; Return isoamyl valerate; Return sour isobutyl ester; The pentenoic acid isopentyl ester; The different byutul ester of pentenoic acid; Methacrylic pentenoate (methylallyl pentenoate); Methyl spiceleaf acid esters; Suitable-3-hexenyl salicylate; Methyl-2-nonenoate; 3,7-dimethyl-6-octenyl-2-methyl butene acid esters; The styracin phenyl chlorocarbonate; 3,7-dimethyl-2,6-octadienyl-2-methyl butene acid esters; Methyl-2-nonenoate; 4-methylpent-2-alcohol crotonate (Frutinat); 2-cyclopentyl-cyclopentyl crotonate (Pyproprunat); 3,7-dimethyl-2 (3), 6-nonadiene nitrile (lemonile), three decene-2-nitrile, 3,12-three decadiene nitriles, 3-methyl-5-phenyl-2-pentenenitrile, 3,7-dimethyl-2,6-nonadiene nitrile and cinnamyl nitrile, filbertone (filbertone), 2-amyl group-2-cyclopentenes-1-ketone; 2-cyclohexyl-1,6-heptadiene-3-ketone, δ-2-decene lactone, 2-amyl group-2-cyclopentenes-1-ketone, 2-hexyl-2-cyclopentenes-1-ketone, 2-hexene-1,4-lactone, but-2-ene-1,4-lactone, 2-decylene-1,4-lactone, 2-methyl-2-pentenoic acid (2-me-2-pentenoic acid), or their mixture.

The ketone that is used to produce The compounds of this invention preferably includes α-damascone, δ-damascone, the big horse of different dihydro, Karvon, γ-methyl ionone, ambrotone, 2,4,4,7-tetramethyl-oct-6-ene-3-ketone, benzyl acetone, β-damascone, trans-Damascenone, methyl dihydrojasmonate, methyl cypress ketenes, and their mixture.

The aldehyde that is used to produce The compounds of this invention preferably includes 1-capraldehyde, phenyl aldehyde, cyanine aldehyde, 2,4-dimethyl-3-tetrahydrobenzene-1-formaldehyde, suitable/anti--3,7-dimethyl-2,6-octadiene-1-aldehyde, piperonylaldehyde, 2,4,6-trimethylammonium-3-tetrahydrobenzene-1-formaldehyde, 2,6-nonadienal, α-n-pentyl phenylacrolein, α-n-hexyl phenylacrolein, phenylpropyl aldehyde (P.T.Bucinal), LYRAL, cymal, methyl nonyl acetaldehyde, hexanal, anti--2-hexanal and their mixture.

Usually, composition of the present invention at room temperature (15 ℃～25 ℃) is a liquid, and measured viscosity is lower than about 250cP under about 20 ℃, preferably is lower than 200cP.Generally, preferred compound of the present invention is lower than 100cP in about 20 ℃ of down measured viscosity, for example is 20cP～100cP or 50cP～80cP.

Can use oneself any suitable method known of this area to measure viscosity.

The invention provides the application of compound of the present invention and composition thereof as condiment and/or spices.

The present invention also provides composition, product, preparation or the finished product that comprise above-mentioned The compounds of this invention or its mixture, and it has fragrance, fragrance or the odor characteristics of improvement.

The present invention also provides and gives, improves, enhancing or the taste of modifying composition, product, preparation or finished product or the method for flavour properties, and it comprises above-mentioned The compounds of this invention or its mixture that adds the local flavor significant quantity to described composition, product, preparation or finished product.

The present invention also provides and gives, improves, the method for fragrance, fragrance or the odor characteristics of enhancing or modifying composition, product, preparation or finished product, and it comprises above-mentioned The compounds of this invention or its mixture that adds fragrance, fragrance or smell significant quantity to described composition, product, preparation or finished product.

Compound of the present invention can make perfume ingredient delay to discharge.Be not limited to theory, think that discharging is to take place by following mechanism: perfume ingredient is released when imines or amine bond rupture, and perfume ingredient and amine compound are released.This can realize by for example hydrolysis, photochemical division, oxidation cleavage or enzyme division.Can successfully discharge perfume ingredient and amine compound with air moisture and/or water treatment.Yet, do not get rid of other method for releasing, for example hydrolysis, photochemical division, oxidation cleavage or enzyme division yet.Can consider that also other discharges the method for perfume ingredient, for example the steam ironing step that treated fabric is carried out, cylinder are dried and/or are worn.Composition of the present invention comprises the composition that need delay to discharge active essence.The composition that uses when this comprises flushing, for example softener composition; The composition of personal cleansing, for example bath gels, reodorant, soap, shampoo; Leave standstill composition, for example deodorant compositions, agrochemical.Those compositions that compound of the present invention is contacted with fabric.Composition of the present invention is applicable to any step in the household processing, and described composition is pre-treatment and/or post-treatment composition, and it is as detergent additive, as the composition that is applicable to rinse step.Obviously, can carry out integrated application, for example handle fabric, then with the composition that is applicable to cleaning procedure and/or drying program with pretreatment compositions of the present invention.

For the composition that is applicable to cleaning procedure, should understand the fabric softening agent composition that adds in the time of to comprise flushing; The composition that adds during with drying (for example flap (sheets)), it can provide kindliness and/or static resistance; And comprise the additive that flushing is used the time.Those compositions that compound of the present invention is contacted with fabric.Should understand the composition (for example flap) that can comprise fabric softening agent composition that when flushing adds and add when dry, it can provide flexibility and/or static resistance.

In fact compound of the present invention can be included in any finished product that comprise the natural or synthetic flavour of non-derivatized perfumes or condiment compound or other.Example comprises SYNTHETIC OPTICAL WHITNER, washing composition, food flavouring and spices, comprises the beverage of alcoholic beverage etc.Compound of the present invention can be applicable to be used to clean in the solid of for example soap, shampoo, body and function deodovization agent and antiperspirant, processing textiles or liquid washing agent, fabric softener, detergent composition and/or household and the industry global function sanitising agent of plate or different surfaces.Certainly, use of a compound is not limited to the said products, can be used for spices other current application in making as them, just make soap and bath gels, health and hair products and body and function deodovization agent, air freshener and makeup send out perfume (or spice), even in for example application in essence and the Gulong perfume of fine perfumery.

Compound of the present invention also is applied to seasoning orally administrable prods such as the beverage, tooth cleaning agent (tablet), for example lozenge, candy, chewing gum, matrix, medicine of food, food flavouring, for example beer and soda.To illustrate in greater detail these purposes below.

Compound of the present invention can be used as fragrant composition, and it uses as simplification compound or its mixture, preferred amounts be essence combination at least about 30wt%, more preferably amount for composition at least about 60wt%.This compound can pure state or form of mixtures use, and do not add component.The olfactory characteristic of these compound individualities also occurs with their form of mixtures, and the mixture of these compounds also can be used as fragrant composition.This may be particularly advantageous, separates and/or purification step because use the mixture of compound to remove from.

In all above-mentioned application, compound of the present invention can use separately, and intermingling uses, or with this area in other fragrant composition, solvent or the auxiliary material of current use mix use.Do not need to describe in more detail the character and the kind of these associating compositions at this, and it can be not detailed, those skilled in the art can rely on their general knowledge and wait that character and the needed aroma effect of sending out incense products select up-to-date associating composition.

These fragrant compositions belong to different chemical classes usually, for example alcohol, aldehyde, ketone, ester, ether, acetic ester, nitrous acid ester, terpene hydrocarbon, sulfur heterocyclic compound and nitrogen-containing heterocycle compound, and natural or synthetic essential oil.A large amount of these compositions have been described, the book of S.Arctander for example, Perfume and Flavor Chemicals in making reference to the text-book, 1969, Montclair, N.J., USA upgrades version with its full content or its or the similarity works are incorporated this paper in this mode by reference.

The content ratio value scope of the compound of incorporating in variant production of the present invention is very big.These values depend on article or the character of product and the odor effect of being pursued of required perfume (or spice), and when this compound is used for mixing with the fragrant associating composition of sending out of the current use in this area, solvent or auxiliary material, depend on the character of the associating composition in given composition.

For instance, with respect to the weight of sending out composition fragrant of having incorporated these compounds into, the concentration of The compounds of this invention is generally about 0.1wt%～10wt%, perhaps even more.When these compounds are directly used in when making above-mentioned different consuming product send out perfume (or spice), its working concentration also can be far below above-mentioned concentration.

These compounds can be used to comprise for example tetraacetyl ethylene diamine (TAED), hypohalite (particularly hypochlorite), the SYNTHETIC OPTICAL WHITNER of peroxide bleaching agent (for example perborate etc.) and the washing composition of activator.These compounds also can be used for for example containing the body and function deodovization agent and the antiperspirant of aluminium salt.To illustrate in greater detail these aspects below.

Except compound of the present invention, these compositions of this paper can comprise detersive surfactant, and optionally comprise one or more extra detergent ingredients, described extra detergent ingredients includes and helps or strengthen clean-up performance, be used to handle matrix to be cleaned, or be used to modify the material of detergent composition (as essence, tinting material, dyestuff etc.) aesthetic.General herein used level comprises conventional C for the limiting examples of the synthesis clean tensio-active agent of about 0.5wt%～90wt% _1-18Alkylbenzene sulfonate/ester (" LAS ") and one-level, side chain and random C _10-20Alkyl-sulphate/ester (" AS ") etc.The composition that only comprises synthetic detergent preferably has about 0.5%～50% washing composition level.The composition that comprises the soap class preferably comprises about soap class of 10%～about 90%.

Composition as herein described can comprise other composition, for example enzyme, SYNTHETIC OPTICAL WHITNER, fabric softener, dye transfer inhibitor, froth suppressor and sequestrant, and they are well known in the art all.

Compound of the present invention can add in the beverage and bring beverage different tastes.Drink composition can be a cola beverage composition, also can be coffee, tea, dairy beverage, juice drinks, tangerine drink, lemon lime drink, beer, malt beverage or other flavouring beverages.These beverages can be liquid or powder type.These drink composition also can comprise one or more seasoningss; The artificial coloring; Vitamin addn; Sanitas; The caffeine additive; Water; Souring agent; Thickening material; Buffer reagent; Emulsifying agent; And/or fruit juice concentrate.

The available artificial coloring comprises caramel colour, yellow 6 (yellow6) and yellow 5 (yellow5).Effectively vitamin addn comprises Wei ShengsuB2, vitamin B6, vitamin B12, vitamins C (xitix), nicotinic acid, pantothenic acid, vitamin H and folic acid.Suitable sanitas comprises Sodium Benzoate or potassium benzoate.Available salt comprises sodium-chlor, Repone K and magnesium chloride.Typical emulsifying agent is Sudan Gum-arabic and pure glue, and effectively thickening material is a pectin.Suitable souring agent comprises citric acid, phosphoric acid and oxysuccinic acid, and possible buffer reagent comprises Trisodium Citrate and Tripotassium Citrate.

For instance, beverage can be a carbonated cola beverage.PH is about 2.8 usually, can use following ingredients to make the syrup of these compositions: the concentrated food flavouring (22.22ml) that contains one or more compounds of the present invention, 80% phosphoric acid (5.55g), citric acid (0.267g), caffeine (1.24g), artificial sweetner, sugar, maize treacle (will taste, depend on actual sweetener) and Tripotassium Citrate (4.07g).For example, can be by aforementioned syrup and soda water be prepared drink composition with the 50ml syrup to the mixed of 250ml soda water.

Also can prepare the seasoning food and the pharmaceutical composition that contain one or more The compounds of this invention.The compounds of this invention can join in the conventional food with the technology of well known to a person skilled in the art.Alternatively, these compounds can join in the aggregated particles, and it can be spread in the oral body material then and/or on its surface, it is solid or semisolid matrix normally.When being used for chewing composition, when chewing said composition and remaining in it in oral cavity, compound of the present invention can be discharged in the oral polymer matrix material, thereby prolongs the fragrance of composition.Dry powder not with the example of mixture in, local flavor can be provided when edible product, perhaps when further treatment compositions, release flavour in the body material.When two kinds of condiment and aggregated particles combination, can select the relative quantity of additive, discharge and consumption in the time of with the realization compound.

Seasoning composition of the present invention can comprise oral body material; The a large amount of water-fast aggregated particles that in oral body material, spreads, wherein aggregated particles constitutes interior pore network respectively, and its non-degradable in digestive tube; And one or more compounds of the present invention in the pore network in being trapped in.The compounds of this invention discharges when chewing matrix, and orally-dissolvable, or The compounds of this invention is released when further handling, and described processing is selected from the group of being made up of following: it is selected from liquid interpolation, dry blending, stirring, mixing, heating, baking and the cooking.Can the optional free glue of oral polymer matrix material, the group formed of latex material, crystallized sugar, amorphous sugar, soft sweets, nougat, jam, fruit jelly, paste, powder, dry mixture, dehydrated food mixes, bake, cream batter, dough/pasta, tablet and lozenge.

Tasteless matrix can make up to obtain required flavour intensity with a kind of compound of the present invention or its mixture.In a kind of method that produces this matrix product, blade mixer is heated to about 110 , the preheating matrix makes it softening, then matrix is added in the mixing tank, and it was mixed about 30 seconds.Then one or more compounds of the present invention are joined in the mixing tank, and make it mix an amount of time.From mixing tank, take out colloid then, and on paraffin paper, roll up while hot to desired thickness.

Compound of the present invention can be incorporated into can discharge in a controlled manner in the system of spices.They comprise the matrix such as air freshener, scouring agent, fabric softener, reodorant, lotion and other household supplies etc.Spices is the derivatives of essential oils of one or more described in the literary composition normally, and every kind has different amounts.U.S.Pat.No.4,587,129 have described preparation contains method up to the gel product of the spices of 90wt% or volatile oil, in this mode by reference its full content is incorporated into.Gel is prepared by polymkeric substance and the unsaturated linking agent of polyvinylization with poly-(lower alkoxy) low alkyl group 2-olefin(e) acid ester of hydroxyl (lower alkoxy) 2-olefin(e) acid ester, hydroxyl (lower alkoxy) low alkyl group 2-olefin(e) acid ester or hydroxyl.These materials have lasting slow release properties, that is to say, they continue to discharge perfume composition in long-time.Advantageously, these all or part of can modifications that comprise the derivative of aldehyde radical make it comprise acetal group, and it can make preparation form aldehyde cpd and discharge fragrance along with the acetal hydrolysis in for some time.

Embodiment illustrates the present invention by detail description.

Embodiment

Embodiment 1

Equimolal amine (267 gram oleyl amine) and odorant agent (odorant) (152 gram 2-amyl group-2-cyclopentenes-1-ketone) are mixed by abundant stirring, and, react this moment and finish basically 50 ℃ of insulated and stirred 3 to 5 hours.

Can monitor the progress of reaction by any suitable method known in the art, for example NMR or chromatography (for example gas-chromatography or thin-layer chromatography) etc.

Embodiment 2

The amine (35 gram oleyl amine) and the filbertone (10 gram) of stoichiometry is admixed together by stir 3 to 5 hours under about 50 ℃, finish basically until reaction.After the reaction mixture cooling (30 minutes), product can be to be separated.

The viscosity of separated product is 50～100cP.

Embodiment 3

In suitable solvent (for example ethanol, dipropylene glycol, myristic acid diisopropyl ester), stir amine (oleyl amine) and have the mixture of the Moschus aldehyde of following formula, until finishing basically by the formation of tlc or NMR judgement imines.Can use additive to add fast response such as acid (for example tosic acid) and dewatering agent (for example molecular sieve/sodium sulfate/sal epsom) etc.Also temperature can be raise to improve condensation.When reaction finishes, (for example filter) by rights and, concentrate then its processing to remove undissolved additive/wash to remove additive, obtain product.

Embodiment 4

The product of the embodiment 2 general concentration with spices in the fabric care agent is dissolved in the fabric care agent.The control fabric nursing agent that has also prepared the filbertone that contains same concentrations.

Make clothing with handling in the clean cycle of two kinds of fabric care agents in the family expenses washing machine, and be dried.

Discovery is compared with the clothing of handling with the fabric care agent that only contains the filbertone of same concentrations, comprises the clothing that the fabric care agent of the product of embodiment 2 handled and shows the smell that comes from filbertone significantly for more time.Comprise clothing that the fabric care agent of filbertone handled and show the smell that comes from filbertone and reach about 1 hour, show the smell that comes from filbertone and reach fortnight approximately and comprise clothing that the fabric care agent of the product of embodiment 2 handled.

So far disclosed purport of the present invention, clearly, the many modifications of the present invention under it inspires, to substitute and change be possible.Should be understood that can with specifically describe different realization the present invention.This modification, to substitute and change be to determine within the scope of this specification sheets.

Claims

1. smell precursor or flavour precursors, it is at room temperature for liquid and have than low viscosity, and has formula (I) structure:

R wherein ¹Be H, aliphatic group or aromatic group, R ²Be aliphatic group or aromatic group, condition is R ¹And R ²Carbon atom adds up to 10 or more in the group;

R ⁵Be CN, COOH, COOR ⁷, CHO or C (O) R ⁸

R ³, R ⁴And R ⁶Independent separately is hydrogen or organic group, itself and R ⁵The formula that provides in the lump is R ⁵R ⁶C=CR ³R ⁴Compound, described compound is for having smell or flavour characteristic material, and R ⁷And R ⁸Independent separately is organic group; Or

Have formula (II) structure:

R ⁹R ¹⁰C＝NR ¹¹

R wherein ¹¹Be aliphatic group or aromatic group with at least 10 carbon atoms; R ⁹And R ¹⁰Independent separately is hydrogen or organic group, and it is R that itself and C=O provide formula in the lump ⁹R ¹⁰The compound of C=O, described compound is for having smell or flavour characteristic material, and condition is R ⁹And R ¹⁰In have only one for hydrogen;

Or have formula (III) structure:

R wherein ¹Be H, aliphatic group or aromatic group, R ²Be aliphatic group or aromatic group, condition is R ¹And R ²Carbon atom adds up to 10 or more in the group; Z is CH ₂Or O, n is 0 or 1, therefore ring is 5 yuan of rings or 6 yuan of rings; R ¹²For H, have the alkyl or alkenyl or the alkoxyl group that mostly are 10 carbon atoms most, obtain following formula: compound thus:

Described compound is for having smell or flavour characteristic material; Or

Or have formula (IV) structure:

R wherein ¹¹Have at least 10 carbon atoms, and be aliphatic group or aromatic group; R ¹³Independent of separately to have the straight or branched of 1～8 carbon atom, saturated or undersaturated alkyl or alkoxyl group, or two R ¹³Group forms saturated or undersaturated 5 yuan of rings or 6 yuan of rings (comprising aromatic ring) with the carbon atom with its connection, and described ring can be chosen wantonly by 1～3 alkyl replacement with 1～6 carbon atom; And x is 1～5, obtains following formula: compound thus:

Described compound is for having smell or flavour characteristic material.

2. the compound with formula (I) according to claim 1, it has chemical formula:

Or

3. the compound with formula (IV) according to claim 1, it has chemical formula:

Or

4. according to the described compound of aforementioned arbitrary claim, its measured viscosity under about 20 ℃ is lower than about 250cP.

5. compound according to claim 4, its measured viscosity under about 20 ℃ is lower than about 100cP.

6. the method for preparing the defined formula of claim 1 (I) compound, it comprises the compound and the formula of formula V are NHR down ¹R ²Amine reaction:

R wherein ¹, R ², R ³, R ⁴, R ⁵And R ⁶Respectively claim 1 defines freely; Or

The method for preparing the defined formula of claim 1 (II) compound, it comprises that with the compound of following formula (VI) and formula be NH ₂R ¹¹Amine reaction:

R ⁹R ¹⁰C＝O，

R wherein ⁹, R ¹⁰And R ¹¹Such as claim 1 definition; Or

The method for preparing the defined formula of claim 1 (III) compound, it comprises that with the compound of following formula (VII) and formula be NHR ¹R ²Amine reaction:

Wherein Z is CH ₂Or O, n is 0 or 1, therefore ring is respectively 5 yuan of rings or 6 yuan of rings; And R ¹, R ²And R ¹²Such as claim 1 definition; Or

The method for preparing the defined formula of claim 1 (IV) compound, it comprises that with the compound of following formula (VIII) and formula be NH ₂R ¹¹Amine reaction:

R wherein ¹¹, R ¹³With x such as claim 1 definition.

7. method according to claim 6, wherein said amine is selected from the n-amino dodecane, the n-tetradecy lamine, the n-cetylamine, the n-stearylamine, oleyl amine, the cocoa alkylamine, the soybean alkylamine, tallow alkylamine, hydrogenated tallow alkyl amine, two-n-hexylamine, two-n-octylame, two-n-decyl amine, two-n-amino dodecane, two-n-tetradecy lamine, two-n-cetylamine, two-n-stearylamine, two-oleyl amine, two-cocoa alkylamine, two-soybean alkylamine, two-tallow alkylamine, two-(hydrogenated tallow alkyl) amine, mix secondary amine, such as n-dodecyl methylamine, n-tetradecyl methylamine, n-hexadecyl methylamine, n-octadecyl methylamine, the oleyl methylamine, cocoa alkyl methylamine, soybean alkyl methylamine, the tallow alkyl methylamine, the hydrogenated tallow alkyl methylamine, n-decyl ethamine, n-dodecyl ethamine, n-tetradecyl ethamine, n-hexadecyl ethamine, n-octadecyl ethamine, oleyl ethamine, cocoa alkyl ethamine, soybean alkyl ethamine, tallow alkyl ethamine, hydrogenated tallow alkyl ethamine, its branched chain isomer and its derivative and their mixture.

8. method according to claim 6, wherein said formula are NHR ¹R ²Or NH ₂R ¹¹Amine comprise at least one and have branched-chain or straight-chain alkyl or thiazolinyl at least about 10 carbon atoms, and described amine is not have relatively to smell flavor.

9. method according to claim 7, wherein said amine is oleyl amine.

10. according to arbitrary described method in the claim 5～8; wherein said formula V; (VI); (VII) or compound (VIII) be selected from buccoxime; isojasmone; β-Nai Yitong; the Moschus indone; tonalide/Moschus; α-damascone; β-damascone; δ-damascone; different damascone; trans-Damascenone; big horse rose ketone; the dihydro methyl jasmonate; piperitone; Karvon; camphor; fenchone; α-Zi Luotong; β-ionone; γ-methyl ionone; 2-n-heptyl cyclopentanone; Dihydrojasmone; suitable-jasmone; ambrotone; methyl cypress ketenes; methyl phenyl ketone; methyl acetophenone; p-methoxy-acetophenone; β-Nai Yitong; benzyl acetone; benzophenone; p-hydroxyphenyl butanone; apione; 6-sec.-propyl decahydro-2-naphthalenone; the dimethyl-octa ketenes; bright piperitone; 4-(1-vinyl ethyl ether base)-3; 3; 5; 5-tetramethyl-ring hexanone; Sulcatone; 2-(2-(4-methyl-3-tetrahydrobenzene-1-yl) propyl group)-cyclopentanone; 1-is (to menthene-6 (2)-yl)-1-acetone; 4-(4-hydroxy 3-methoxybenzene base)-2-butanone; 2-ethanoyl-3; 3-dimethyl norcamphane; 6; 7-dihydro-1; 1; 2; 3; 3-pentamethyl--4 (5H)-indone; 4-Tujue alcohol; piperonylacetone; 2-hexyl methyl aceto acetate; the allyl group ionone; isocyclemone E; the trimethylcyclohexyl ketone; methyl lavender ketone; orivone; to tertiary butyl pimelinketone; 2-tertiary butyl pimelinketone; 2 n hexyl cyclopentanone; muskone; new methylene acetone; the medicine ketone musk; the di-t-butyl pimelinketone; 2; 4; 4; 7-tetramethyl--oct-6-ene-3-ketone; 3; 4; 5; the 6-tetrahydropseudoionone; A Daoke aldehyde; aubepine; 3-(4-isopropyl phenyl) butyraldehyde; vanirone; cyanine aldehyde; helional; piperonylaldehyde; laurine; koavone; lauryl aldehyde; LYRAL; methyl nonyl acetaldehyde; phenylpropyl aldehyde; phenylacetic aldehyde; undecylene aldehyde; Vanillin; 2; 6; 10-trimethylammonium-9-undecylene aldehyde; 3-laurylene-1-aldehyde; α-n-pentyl phenylacrolein; the 4-methoxybenzaldehyde; phenyl aldehyde; 3-(uncle's 4-phenyl) propionic aldehyde; 2-methyl-3-(p-methoxyphenyl) propionic aldehyde; 2-methyl-4-(2; 6; 6-trimethylammonium-2 (1)-tetrahydrobenzene-1-yl) butyraldehyde; 3-phenyl-2-propenal; suitable/anti--3; 7-dimethyl-2; 6-octadiene-1-aldehyde; 3; 7-dimethyl-6-octene-1-aldehyde; [(3; 7-dimethyl-6-octenyl) oxygen base] acetaldehyde; 4-isopropyl benzene formaldehyde; 1; 2; 3; 4; 5; 6; 7; 8-octahydro-8; 8-dimethyl-2-naphthaldehyde; 2; 4-dimethyl-3-tetrahydrobenzene-1-formaldehyde; 2-methyl-3-(isopropyl phenyl) propionic aldehyde; the 1-capraldehyde; capraldehyde; 2,6-dimethyl-5-heptenal; 4-(three ring [5.2.1.0 (2,6)]-Ya decyls-8)-butyraldehyde; octahydro-4; 7-methylene radical-1H-indenes formaldehyde; vanirom; to ethyl-α; the alpha-alpha-dimethyl hydrocinnamic aldehyde; Alpha-Methyl-3,4-(methylene radical dioxy base) hydrocinnamic aldehyde; 3,4-methylenedioxyphenyl formaldehyde; α-n-hexyl phenylacrolein; m-isopropyl benzene-7-formaldehyde; the Alpha-Methyl phenylacetic aldehyde; 7-hydroxyl-3; 7-dimethyl octanal; undecylene aldehyde; 2; 4,6-trimethylammonium-3-tetrahydrobenzene-1-formaldehyde; 4-(3) (4-methyl-3-pentenyl)-3-tetrahydrobenzene formaldehyde; the 1-lauric aldehyde; 2, the 4-triplal; 4-(4-hydroxy-4-methyl phenyl)-3-tetrahydrobenzene-1-formaldehyde; 7-methoxyl group-3; 7-dimethyl-octa-1-aldehyde; the 2-methyl undecyl aldehyde; 2-methyl capraldehyde; the 1-aldehyde C-9; the 1-octanal; 2; 6,10-trimethylammonium-5,9-11 olefine aldehydrs; 2-methyl-3-(the 4-tertiary butyl) propionic aldehyde; the dihydro phenylacrolein; 1-methyl-4-(4-methyl-3-pentenyl)-3-tetrahydrobenzene-1-formaldehyde; 5 or 6 methoxyl group six hydrogen-4; 7-methylene radical indane-1 or 2-formaldehyde; 3; 7-dimethyl-Xin-1-aldehyde; the 1-undecyl aldehyde; 10-hendecene-1-aldehyde; 4-hydroxy 3-methoxybenzene formaldehyde; 1-methyl-3-(4-aminomethyl phenyl)-3-tetrahydrobenzene formaldehyde; 7-hydroxyl-3,7-dimethyl octanal; instead-the 4-decenal; 2, the 6-nonadienal; p-tolyl acetaldehyde; the 4-methyl phenylacetaldehyde; 2-methyl-4-(2; 6; 6-trimethylammonium-1-tetrahydrobenzene-1-yl)-crotonic aldehyde; o-methoxy cinnamic aldehyde; 3,5,6-trimethylammonium-3-tetrahydrobenzene formaldehyde; 3; 7-dimethyl-2-methylene radical-6-octenal; phenoxy acetaldehyde; 5; 9-dimethyl-4, the 8-decadienal; tree peony aldehyde (6,10-dimethyl-3-oxa--5; 9-11 diene-1-aldehyde); six hydrogen-4; 7-methylene radical indane 1-formaldehyde; 2 methyl octylaldehyde; Alpha-Methyl-4-(1-methylethyl) phenylacetic aldehyde; 6, firpene-2-propionic aldehyde falls in 6-dimethyl-2-; to the methylenedioxy phenoxy ethylhexanal; 2-methyl-3-phenyl-2-propylene-1-aldehyde; 3,5; 5-trimethylammonium hexanal; six hydrogen-8; 8-dimethyl-2-naphthaldehyde; 3-propyl group-dicyclo [2.2.1] heptan-5-alkene-2-formaldehyde; the 9-decenal; 3-methyl-5-phenyl-1-valeral; methyl nonyl acetaldehyde; hexanal; instead-the 2-hexenoic aldehyde; 1-is to methylene-q-formaldehyde; 2-methyl-2-(p-isopropyl phenyl) propionic aldehyde; 1-(2,6,6-trimethylammonium-2-hexamethylene-1-yl)-2-butylene-1-ketone and/or p-methoxy-acetophenone; undecylene aldehyde; γ-Shi Yineizhi; piperonylaldehyde; γ-dodecalactone; p-anisaldehyde; the p-hydroxybenzene butanone; cymal; α-Zi Luotong; trans-Damascenone; β-ionone; methyl nonyl ketone; compound with following formula:

R wherein ¹⁴And R ¹⁵Independent is H or the alkyl or alkenyl with straight or branched of 1～6 carbon atom; 2,4-di-t-butyl-5-methoxybenzaldehyde; Polycyclic musk with following structure:

Or

Wherein, R ¹⁶And R ¹⁷Can be identical or different, and it is straight or branched, saturated or undersaturated alkyl; Be preferably alkyl or alkenyl, and m is 1～4 and n is 1～6 with 1～8 carbon atom; 4-methylpent-2-alcohol-crotonate, 1-cyclohexyl ethyl crotonate (Datilat) and the own ester of butenoic acid; The pentenoic acid butyl ester; The pentenoic acid ethyl ester; Return sour own ester; The own ester of pentenoic acid; Return isoamyl valerate; Return sour isobutyl ester; The pentenoic acid isopentyl ester; The different byutul ester of pentenoic acid; The methacrylic pentenoate; Methyl spiceleaf acid esters; Suitable-3-hexenyl salicylate; Methyl-2-nonenoate; 3,7-dimethyl-6-octenyl-2-methyl butene acid esters; The styracin phenyl chlorocarbonate; 3,7-dimethyl-2,6-octadienyl-2-methyl butene acid esters; Methyl-2-nonenoate; 4-methylpent-2-alcohol-crotonate (Frutinat); 2-cyclopentyl-cyclopentyl crotonate (Pyproprunat); 3,7-dimethyl-2 (3), 6-nonadiene nitrile (lemonile), three decene-2-nitrile, 3,12-three decadiene nitriles, 3-methyl-5-phenyl-2-pentenenitrile, 3,7-dimethyl-2,6-octadiene nitrile and cinnamyl nitrile, filbertone, 2-amyl group-2-cyclopentenes-1-ketone, 2-cyclohexyl-1,6-heptadiene-3-ketone, δ-2-decene lactone, 2-amyl group-2-cyclopentenes-1-ketone, 2-hexyl-2-cyclopentenes-1-ketone, 2-hexene-1,4-lactone; But-2-ene-1,4-lactone, 2-decylene-1,4-lactone, 2-methyl-2-pentenoic acid, or their mixture.

11. the method for preparing the described compound of claim 3 according to claim 6, it comprises that with the compound of following structure and formula be H ₂N (CH ₂) ₈CH=CH (CH ₂) ₇CH ₃Amine reaction:

Or be H with the compound and the formula of following structure ₂N (CH ₂) ₈CH=CH (CH ₂) ₇CH ₃Amine reaction:

12. any one defined compound is as the application of condiment or spices in the claim 1 to 5.

13. the matrix of crossing with any one defined compound treatment in the claim 1 to 5.

14. handle matrix to give the method for its flavour/aroma release characteristic, described method comprises with any one defined compound treatment matrix in the claim 1 to 5.

15. have composition, product, preparation or the finished product of fragrance, fragrance or smell release characteristic, it comprises the mixture of any one defined compound in the auxiliary material blended claim 1 to 5 of optional and other fragrant composition, the current use of solvent or this area or compound.

16. composition according to claim 15, product, preparation or finished product, the content of the mixture of any one defined compound or compound is 30wt% at least in the wherein said claim 1 to 5.

17. composition according to claim 16, product, preparation or finished product, the content of the mixture of any one defined compound or compound is 60wt% at least in the wherein said claim 1 to 4.

18. according to any one described composition, product, preparation or finished product in the claim 15 to 17, it is following form: essence, spices or Gulong perfume, soap, shower or shower gels, shampoo or other hair products, makeup, fragrant body agent, reodorant or antiperspirant, air freshener, liquid or solid fabric detergent or softener, bleach product, sterilizing agent or global function household or industrial cleaners.

19. detergent composition according to claim 18, product, preparation or finished product, wherein the mixture of any one defined compound or compound mixes with other detergent ingredients, solvent or auxiliary material in the claim 1 to 5.

20. whitener composition according to claim 18, product, preparation or finished product, wherein the mixture of defined compound of any one in the claim 1 to 5 or compound mixes with other bleach additive composition, solvent or auxiliary material.

21. antiseptic composition according to claim 18, product, preparation or finished product, wherein the mixture of defined compound of any one in the claim 1 to 5 or compound mixes with other sterilizing agent composition, solvent or auxiliary material.

22. composition according to claim 18, product, preparation or finished product, it is following form: fragrant body agent, reodorant or antiperspirant, wherein the mixture of compound or compound mixes with other fragrant body agent, reodorant or antiperspirant composition, solvent or auxiliary material.

23. comprise composition, product, preparation or the finished product of the mixture of any one defined compound in the claim 1 to 5 or compound, it has the feature of the local flavor or the taste of improvement.

24. composition according to claim 23, product, preparation or finished product, it is a drink form, its optional other drink component, solvent or auxiliary material of comprising.

25. composition according to claim 23, product, preparation or finished product, it is the food flavouring form, its optional other food flavouring composition, solvent or auxiliary material of comprising.

26. composition according to claim 23, product, preparation or finished product, it is a food forms, its optional other food ingredient, solvent or auxiliary material of comprising.

27. composition according to claim 23, product, preparation or finished product, it is a gum formats, its optional other chewing gum component, solvent or auxiliary material of comprising.

28. composition according to claim 23, product, preparation or finished product, it is a medicament forms, its optional other medicines composition, solvent or auxiliary material of comprising.

29. composition according to claim 23, product, preparation or finished product, it is oral body material form, its optional other body material composition, solvent or auxiliary material of comprising.

30. give, improve, enhancing or the taste of modifying composition, product, preparation or finished product or the method for fragrance, it comprises to described composition, product, preparation or finished product and adds the mixture that its content can effectively produce any one defined compound in the claim 1 to 5 of local flavor or compound.

31. method according to claim 30, wherein said composition, product, preparation or finished product are following form: beverage, food flavouring, food, chewing gum, medicine or oral matrix.

32. give, improve, the method for fragrance, fragrance or the odor characteristics of enhancing or modifying composition, product, preparation or finished product, it comprises to described composition, product, preparation or finished product and adds the mixture that its content can effectively produce any one defined compound in the claim 1 to 5 of fragrance, fragrance or smell or compound.

33. method according to claim 32, wherein said composition, product, preparation or finished product are following form: essence, fragrant body agent, reodorant or antiperspirant, washing composition, bleach product or sterilizing agent.

34. finished product, it comprises wrapping material and the fragrance, smell, fragrance, taste or the fragrance toughener that are contained in the wrapping material, wherein said toughener effectively strengthens fragrance, smell, fragrance, taste or the fragrance of the composition, product, preparation or the finished product that have added toughener, and wherein said wrapping material comprise label, described label illustrated that described toughener can be used in and improved fragrance, smell, fragrance, taste or fragrance, and wherein said toughener is the mixture of any one defined compound or compound in the claim 1 to 5.

35. aforesaid smell precursor of this paper or flavour precursors.

36. aforesaid operation of this paper or method.

37. this paper aforementioned compositions or finished product.