Classifications

• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
  • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
  • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
  • A23L2/52—Adding ingredients
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/34—Alcohols
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q13/00—Formulations or additives for perfume preparations
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C47/00—Compounds having —CHO groups
  • C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
  • C07C47/19—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing hydroxy groups
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C47/00—Compounds having —CHO groups
  • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
  • C07C47/26—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing hydroxy groups
  • C07C47/263—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing hydroxy groups acyclic
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C47/00—Compounds having —CHO groups
  • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
  • C07C47/26—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing hydroxy groups
  • C07C47/267—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing hydroxy groups containing rings other than six-membered aromatic rings
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
  • C11B9/00—Essential oils; Perfumes
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
  • C11D3/50—Perfumes

Definitions

• the present invention relates to a flavoring agent composed of a hydroxyaldehyde compound. Furthermore, the present invention relates to a fragrance composition containing the flavor-imparting agent, and a novel hydroxyaldehyde compound.
• fragrance compounds that can improve the flavor by blending, for example, to give or enhance the aroma and taste with a long-lasting, natural feeling, volume feeling, etc., and a new fragrance and flavor that can be improved.
• a search for fragrance compounds is underway.
• An object of the present invention is to provide a flavor-imparting agent that exhibits an excellent flavor-imparting effect that cannot be obtained with existing compounds.
• the present invention provides:
• a flavor-imparting agent consisting of at least one hydroxyaldehyde compound represented by the following formula 1.
• the dashed lines at positions C4 and C8 indicate that they are single or double bonds, respectively, and in the case of double bonds, cis or trans type, or cis type and trans type. Indicates that it is a mixture of any proportion
• the C8 position is a single bond, is R 1 an OH group and R 2 and R 3 are independent hydrogens, or linear or branched alkyl groups with 1-3 carbon atoms, respectively; with 2 and C9 position carbon atoms of the R 3 is attached either to form a three-membered ring; R 2 and R 3 form a methylidene group having a double bond with the carbon of the C9 position together; Is one of If the C8 position is a double bond, R 1 is absent, R 2 is hydrogen or a linear or branched alkyl group with 1-3 carbon atoms, and R 3 is an OH group or CH 2 OH group. be.
• the flavor-imparting agent according to [1] which comprises at least one of
• a fragrance composition containing the flavor-imparting agent according to any one of [1] to [5].
• a consumer good containing the flavor-imparting agent according to any one of [1] to [5] or the fragrance composition according to [6].
• a method for improving the flavor of a fragrance composition which comprises blending the flavor-imparting agent according to any one of [1] to [5] into the fragrance composition.
• a method for imparting flavor to consumer goods which comprises blending the flavoring agent according to any one of [1] to [5] or the flavoring composition according to [6] into consumer goods.
• a hydroxyaldehyde compound represented by the following formula 1'.
• the broken line indicates that it is a single bond or a double bond, and in the case of a double bond, it indicates that it is a cis type or a trans type, or a mixture of an arbitrary ratio of a cis type and a trans type.
• R 2 'and R 3' are each independently hydrogen, or a linear or branched alkyl group having 1 to 3 carbon atoms, with the carbon atoms C9 position of R 2 'and R 3' are attached Form a three-membered ring. (However, the broken line is a single bond, and except when R 2 'and R 3' is hydrogen.)] [11]
• the hydroxyaldehyde compound according to [10] which is represented by the following formulas 1-3 to 1-7.
• the wavy line represents a cis or trans type, or a mixture of cis and trans types in any proportion.
• X to Y indicating a range means a range including a lower limit value (X) and an upper limit value (Y), and means "X or more and Y or less”.
• concentration and% shall represent mass concentration and mass%, respectively, and the ratio shall be the mass ratio unless otherwise specified.
• operations and measurements of physical properties were performed under the conditions of room temperature (20 to 25 ° C.) / relative humidity of 40 to 50% RH, but the conditions are not limited to these conditions.
• hydroxyaldehyde compound represented by the formula 1 (sometimes referred to as the compound of the formula 1) has been confirmed to be useful as a flavor-imparting agent for the first time by the present inventors.
• isomers having slightly different structures do not give off a scent or give off an unpleasant scent.
• each analog exhibits a preferable scent and an effective amount. It is based on the unexpected finding that a favorable flavor can be imparted to an article by blending it with the article.
• one form of the present invention is a flavor-imparting agent consisting of at least one hydroxyaldehyde compound represented by the following formula 1. According to the present invention, it is possible to provide a new flavor-imparting agent capable of imparting flavor to various articles. In addition, another embodiment of the present invention provides an application in which the hydroxyaldehyde compound represented by the formula 1 is used as a flavor-imparting agent.
• the broken lines between the C4 and C5 positions and between the C8 and C9 positions indicate that they are independently single or double bonds, and in the case of double bonds, they are cis type. Alternatively, it indicates that it is a trans type, or a mixture of a cis type and a trans type in an arbitrary ratio.
• R 1 is an OH group
• R 2 and R 3 are independently hydrogen, or a linear or branched alkyl having 1 to 3 carbon atoms.
• R 1 is an OH group and forms a three-membered ring with a carbon atom at the C9 position to which R 2 and R 3 are bonded.
• R 1 is an OH group, and R 2 and R 3 together form a methylene group having a double bond with a carbon atom at the C9 position;
• the broken line between the C4 position and the C5 position indicates that it is a single bond or a double bond, and in the case of a double bond, it is a cis type, a trans type, or a cis.
• R 2 and R 3 are independently hydrogen or linear or branched alkyl groups with 1-3 carbon atoms.
• the linear or branched alkyl group having 1 to 3 carbon atoms as R 2 and R 3 includes a methyl group, an ethyl group, an n-propyl group and an isopropyl group.
• the OH group is a so-called hydroxyl group, which is also called a hydroxy group or a hydroxyl group.
• the broken lines between the C4 and C5 positions and between the C8 and C9 positions may be independently single bonds or double bonds, but any one of them. Is preferably a double bond. That is, preferably, in Equation 1, the carbon-carbon double bond represented by the broken line is one or two places, and more preferably, the broken line between at least the C4 position and the C5 position is the double bond. Is. In the present specification, the form in which the broken line between the C4 position and the C5 position is a double bond is simply "the C4 position is a double bond", and the broken line between the C8 position and the C9 position is two. The form of a double bond may be abbreviated as simply "the C8 position is a double bond".
• the hydroxyaldehyde compound represented by the formula 1 has a C4 position and a C5 when the broken line between the C4 position and the C5 position is a double bond. It is preferable to take the E form in the double bond between the positions. That is, the hydroxyaldehyde compound represented by the formula 1 is preferably a 4E compound. As described in detail in the section of Examples, the present inventors have found through diligent studies that the 4E form has a stronger scent than the 4Z form and has a scent closer to that of fresh lily of the valley flowers. Therefore, the 4E form is particularly useful as a flavoring agent.
• the configuration of the hydroxyaldehyde compound represented by the formula 1 (whether it is E-form or Z-form) is mainly determined by high performance liquid chromatography (HPLC) or nuclear magnetic resonance spectrum ( 1 H-NMR, 13 C-). It can be determined by NMR).
• the imparting agent is preferably in the form of the above (i) and (iii) (that is, the hydroxyaldehyde compound represented by the above formulas (i) and (iii)).
• the flavor-imparting agent is represented by the above-mentioned form (iiii) (that is, the above-mentioned formula (iii) in that it is possible to impart a high-quality aroma pronounced of fresh flowers, particularly for lily of the valley-like aroma.
• R 2 and R 3 are preferably hydrogen, methyl group, or ethyl group, respectively, and more preferably hydrogen or methyl group.
• the compound of formula 1 itself exhibits aromas such as lily of the valley (also called muguet, lily of the valley), floral, green, woody, citrus (citrus), rose, ozone-like, and as a flavoring agent like a fragrance compound. It can be used.
• a specific example of a preferable structure of the hydroxyaldehyde compound represented by the formula 1 is represented by any of the following formulas 1-1 to 1-7. That is, the flavor-imparting agent according to the present invention preferably comprises at least one of the hydroxyaldehyde compounds represented by the following formulas 1-1 to 1-7.
• Equation 1-1 the broken line between the C8 and C9 positions is a single bond in Equation 1, R 1 is an OH group, and R 2 and R 3 are combined to form a carbon at the C 9 position.
• the broken line between the C8 position and the C9 position in the formula 1 is a single bond. This is the case where R 1 is an OH group and R 2 and R 3 form a three-membered ring together with the carbon atom at the C9 position to which they are bonded (that is, the form of (ii) above).
• the hydroxyaldehyde compound represented by the formula 1 may be represented by the following formula 1-1-1 (4E) or formula 1-2-1 (4E, 8E).
• These hydroxyaldehyde compounds are particularly useful as flavor-imparting agents because they give off a scent close to that of fresh lily of the valley flowers and have a strong scent. That is, as a preferred embodiment of the present invention, a flavor-imparting agent consisting of at least one hydroxyaldehyde compound represented by the following formula 1-1-1 (4E) or formula 1-2-1 (4E, 8E) is provided.
• NS a flavor-imparting agent consisting of at least one hydroxyaldehyde compound represented by the following formula 1-1-1 (4E) or formula 1-2-1 (4E, 8E) is provided.
• the flavor means one or more kinds of sensations that can be stimulated by the scent, typically a sensation including the sense of smell and the sense of taste.
• the term "adding flavor” includes adding or enhancing the flavor, and for example, the flavor may be improved as a result of the addition.
• sensations other than the sense of smell and taste such as coldness, warmth, texture (also called texture such as throat, hardness, viscosity, etc.), irritation such as carbonic acid and spiciness, etc. May be enhanced, suppressed, or ameliorated.
• the hydroxyaldehyde compound represented by the formula 1' is included in the hydroxyaldehyde compound represented by the above formula 1, and is a novel compound which has not been described in the conventional literature.
• the hydroxyaldehyde compound represented by the formula 1' has a lily of the valley-like, floral, green, woody, citrus-like, rose-like, ozone-like aroma, and can be used as a flavoring agent such as a fragrance compound. Is.
• R 2 'and R 3' are each independently hydrogen or a linear or branched alkyl group having a carbon number of 1 ⁇ 3, R 2 'and R 3' carbon atoms of the C9 position to which they are attached, Together they form a three-membered ring.
• R 2' above formula 1 Specific examples and preferred embodiments of the linear or branched alkyl group having 1 to 3 carbon atoms as a and R 3 ', in the above formula 1, the number of carbon atoms as R 2 and R 3 This is the same as that of 1 to 3 linear or branched alkyl groups.
• the hydroxyaldehyde compound represented by the formula 1' is preferably a compound represented by any of the following formulas 1-3 to 1-7.
• the wavy line represents a cis or trans type, or a mixture of cis and trans types in any proportion.
• hydroxyaldehyde compound represented by formula 1 The means for obtaining the hydroxyaldehyde compound represented by the formula 1 is not particularly limited.
• the compound can be obtained, for example, by the following methods, but is not limited thereto.
• A As a starting material, it has a hydroxy group and is doubled at the second position (between the C2 and C3 positions) and the sixth position (between the C6 and C7 positions) from the end of the carbon chain.
• a compound having a bond is prepared, and the double bond at the second position is oxidized to an aldehyde group via epoxidation;
• B As a starting material, it has a carbonyl group and is doubled at the second position (between the C2 and C3 positions) and the sixth position (between the C6 and C7 positions) from the end of the carbon chain.
• a compound having a bond is prepared, and the carbonyl group is made into an alkyl group such as a methyl group, an ethyl group, an isopropyl group, and a hydroxy group (that is, a tertiary alcohol) by a Grignard reagent, and a double bond at the second position is provided. Is oxidized to an aldehyde group via epoxidation;
• C Any combination of the reactions according to (A) to (B).
• the non-droxyaldehyde compound is appropriately subjected to a hydrogenation reaction using a catalyst.
• a hydroxyaldehyde compound having a single bond at the C4 position (for example, a compound represented by the above formula 1-4) can be obtained.
• the reagents, solvents, reaction conditions, etc. used for each of the above reactions may be appropriately selected as long as the desired product can be obtained.
• the conversion of a double bond to an aldehyde group can be carried out using metachloroperbenzoic acid, periodic acid or a salt thereof.
• it can be carried out using N-bromosuccinimide, potassium carbonate, periodic acid dihydrate and the like.
• the Grignard reagent used in (B) can be obtained, for example, by reacting a halogenated hydrocarbon with metallic magnesium.
• the fragrance composition according to still another form of the present invention contains a flavor-imparting agent composed of a hydroxyaldehyde compound represented by the formula 1. Furthermore, yet another embodiment of the present invention also provides an application in which the hydroxyaldehyde compound represented by the formula 1 is used as a fragrance composition.
• a fragrance composition can be blended with various articles for the purpose of imparting flavor. Specific examples include a perfume composition for cosmetics (also referred to as a fragrance composition) and a perfume composition for food and drink (also referred to as a flavor composition).
• examples of the articles to be blended include various consumer goods such as cosmetics, foods and drinks, and other miscellaneous goods.
• the form of the fragrance composition of the present invention is not particularly limited, and examples thereof include water-soluble fragrance compositions, oil-soluble fragrance compositions, emulsified fragrance compositions, and powder fragrance compositions.
• still another form of the present invention provides a method for improving the flavor of a perfume composition, which comprises blending the above-mentioned flavor-imparting agent into the perfume composition.
• the method for blending the flavor-imparting agent is not particularly limited, and the flavor-imparting agent can be blended using a method known to those skilled in the art.
• the concentration of the flavor-imparting agent composed of the hydroxyaldehyde compound represented by the formula 1 in the fragrance composition of the present invention can be arbitrarily determined according to the blending target of the fragrance composition.
• the concentration in the case of a fragrance composition for cosmetics, for example, 0.0005% to 60%, preferably 0.001% to 50%, more preferably 0.
• the range is 01% to 20%, more preferably 0.05 to 15%, and particularly preferably 0.1% to 10%.
• the lower limit is 0.0005%, 0.001%, 0.01%, 0.05%, 0.1%, 1%, 10%, 20%, 30%, or 40%.
• the upper limit is set to 60%, 50%, 40%, 30%, 20%, 15%, 10%, 1%, 0.1%, or 0.01%, and these lower and upper limits are set. It can be within the range of any combination of, but is not limited to these.
• the concentration of the flavor-imparting agent composed of the hydroxyaldehyde compound represented by the formula 1 in the fragrance composition for cosmetics is 0.0005% or more, and further 0.
• the concentration may be lower than the lower limit or higher than the upper limit.
• a flavor composition for food and drink for example, it is in the range of 10 ppb to 10%, preferably 100 ppb to 1%, and more preferably 1 ppm to 0.1% with respect to the total mass of the flavor composition. More specifically, the lower limit is 10 ppb, 100 ppb, 1 ppm, 10 ppm, 100 ppm, 0.1%, or 1%, and the upper limit is 10%, 1%, 0.1%, 100 ppm, 10 ppm, 1 ppm. , 100 ppb, and may be within the range of any combination of these lower limit values and upper limit values, but is not limited thereto.
• the concentration of the flavor-imparting agent composed of the hydroxyaldehyde compound represented by the formula 1 in the fragrance composition for cosmetics is 10 ppb or more. It is felt, and when it is 10% or less, the aroma derived from the hydroxyaldehyde compound represented by the formula 1 does not become too strong, and it is possible to suppress giving unfavorable alteration to the flavor characteristics of the food and drink flavor composition to be blended. can do.
• the concentration may be lower than the lower limit or higher than the upper limit.
• the fragrance composition of the present invention contains a flavor-imparting agent composed of a hydroxyaldehyde compound represented by the formula 1, but "containing” includes an embodiment in which a desired fragrance is contained in an amount capable of exhibiting. Therefore, the fragrance composition of the present invention may contain only the hydroxyaldehyde compound represented by the formula 1, but other fragrance components and other additives such as a solvent as long as the desired fragrance is not impaired. Etc. may be included. Such other fragrance components and other additives are such that the fragrance composition (and the hydroxyaldehyde compound represented by the formula 1 contained in the composition) is contained in the additive at an appropriate concentration. And can be added for the purpose of being uniformly dispersed.
• fragrance compounds or compositions examples include various fragrance compounds or compositions, oil-soluble pigments, vitamins, functional substances, fish extracts, livestock extracts, plant extracts, yeast extracts, animal and plant proteins.
• Classes, animal and plant proteolytic compounds, starch, dextrin, sugars, amino acids, nucleic acids, organic acids, solvents and the like can be exemplified.
• synthetic fragrance compounds include hydrocarbon compounds such as ⁇ -pinene, ⁇ -pinene, ⁇ -terpinene, myrcene, camphene, limonene and other monoterpenes, valencene, sedrene, cariophyllene and longifolene and other sesquiterpenes. Examples include 3,5-Undecatorien.
• the alcohol compound examples include saturated alkanols such as butanol, pentanol, 3-octanol and hexanol, unsaturated alcohols such as (Z) -3-hexen-1-ol and pranol, and 2,6-nonazienol, linalool, geraniol and citronellol. , Tetrahydromilsenol, farnesol, nerolidol, cedrol, ⁇ -terpineol, terpinen-4-ol, terpenal alcohols such as borneol, benzyl alcohol, phenylethyl alcohol, cinnamyl alcohol and other aromatic alcohols.
• saturated alkanols such as butanol, pentanol, 3-octanol and hexanol
• unsaturated alcohols such as (Z) -3-hexen-1-ol and pranol
• aldehyde compound examples include saturated aldehydes such as acetaldehyde, hexanal, octanal, decanal, and hydroxycitroneral, unsaturated aldehydes such as (E) -2-hexenal, and 2,4-octadienal, citronellal, citral, miltenal, and peryl.
• saturated aldehydes such as acetaldehyde, hexanal, octanal, decanal, and hydroxycitroneral
• unsaturated aldehydes such as (E) -2-hexenal, and 2,4-octadienal
• citronellal citral, miltenal, and peryl
• terpenaldehyde such as aldehyde, benzaldehyde, cinnamylaldehyde, vanillin, ethyl vanillin, heliotropin, and aromatic alde
• Ketone compounds include saturated and unsaturated ketones such as 2-heptanone, 2-undecanone, 1-octen-3-one, acetoin, 6-methyl-5-hepten-2-one (methylheptenone), diacetyl, 2,3. -Pentandione, sulcatone, ethylmaltor, cycloten, 2,5-dimethyl-4-hydroxy-3 (2H) -diketones such as furanone and terpenketones such as hydroxyketone, carboxylic, menton, nutcatone, ⁇ -ionone, ⁇ - Examples thereof include ketones derived from terpenic decomposition products such as ionone and ⁇ -damasenone, and aromatic ketones such as raspberry ketone.
• ketones derived from terpenic decomposition products such as ionone and ⁇ -damasenone
• aromatic ketones such as raspberry ketone.
• furan or ether compounds examples include furfuryl alcohol, furfural, rose oxide, linalool oxide, mentofran, theaspirane, estragole, eugenol, 1,8-cineole and the like.
• Ester compounds include ethyl acetate, isoamyl acetate, octyl acetate, ethyl butyrate, ethyl isobutyrate, isoamyl butyrate, ethyl 2-methylbutyrate, ethyl isovalerate, 2-methylbutyl isobutyrate, ethyl hexanoate, allyl hexanate, heptane.
• Adipose esters such as ethyl acid, ethyl caprylate, isoamyl isoamyl acetate, ethyl nonanoate, terpenal esters such as linaryl acetate, geranyl acetate, lavandryl acetate, terpinyl acetate, neryl acetate, benzyl acetate, methyl salicylate, silicic acid Examples include aromatic esters such as methyl, cinnamyl propionate, ethyl benzoate, cinnamyl isoamyl acetate, and ethyl 3-methyl-2-phenylglycidate.
• lactone compound examples include saturated lactones such as ⁇ -decalactone, ⁇ -dodecalactone, ⁇ -decalactone and ⁇ -dodecalactone, and unsaturated lactones such as 7-decene-4-olid and 2-decene-5-olid. ..
• acid compounds include saturated and unsaturated fatty acids such as acetic acid, butyric acid, isovaleric acid, caproic acid, octanoic acid, stearic acid, oleic acid, linoleic acid, and linolenic acid.
• nitrogen-containing compound examples include indole, skatole, pyridine, alkyl-substituted pyrazine, methyl anthranilate, and trimethylpyrazine.
• sulfur-containing compound examples include methanethiol, dimethyl sulfide, dimethyl disulfide, allyl isothiocyanate, 3-methyl-2-butane-1-thiol, 3-methyl-2-butanethiol, 3-methyl-1-butanethiol, and 2 Examples thereof include -methyl-1-butanethiol, 3-mercaptohexanol, 4-mercapto-4-methyl-2-pentanone, 3-mercaptohexyl acetate, p-mentor-8-thiol-3-one and furfuryl mercaptan. ..
• Natural essential oils include sweet orange, bitter orange, petit grain, lemon, bergamot, mandarin, neroli, peppermint, spearmint, lavender, chamomile, rosemary, eucalyptus, sage, basil, rose, hyacinth, lilac, geranium, jasminum, Iran Iran. , Anis, cloves, ginger, nutmeg, cardamon, sage, hinoki, vetiver, mint, lovedanum, etc.
• fragrances examples include jasmine absolute, hyacinth absolute, rose absolute, tuberose absolute, vanilla absolute, and galvanum resinoid.
• Examples of various animal and plant extracts include extracts of herbs or spices, extracts of coffee, green tea, black tea, or oolong tea, milk or processed dairy products, and various enzymatic decomposition products such as lipases and / or proteases thereof.
• the fragrance composition of the present invention can be prepared by blending the hydroxyaldehyde compound represented by the formula 1 with an appropriate solvent or dispersion medium by a known method.
• the form of the fragrance composition of the present invention includes a solution in which the hydroxyaldehyde compound represented by the formula 1 and other components are dissolved in a water-soluble or oil-soluble solvent, an emulsified preparation, a powder preparation, and other solid preparation (solid fat, etc.). Etc. are preferable.
• water-soluble solvent examples include ethanol, methanol, acetone, tetrahydrofuran, acetonitrile, 2-propanol, methyl ethyl ketone, glycerin, propylene glycol, dipropylene glycol and the like. Of these, ethanol or glycerin is particularly preferable from the viewpoint of use in foods and drinks.
• Oil-soluble solvents include vegetable fats and oils, animal fats and oils, refined fats and oils (for example, processed fats and oils such as medium-chain fatty acid triglycerides, short-chain fatty acid triglycerides such as triacetin and tripropionin), various essential oils, and triethylcitrate. Etc. can be exemplified.
• an emulsified preparation it can be obtained by emulsifying the hydroxyaldehyde compound represented by the formula 1 together with a water-soluble solvent and an emulsifier.
• the method for emulsifying the hydroxyaldehyde compound represented by the formula 1 is not particularly limited, and various types of emulsifiers conventionally used in foods and drinks, such as fatty acid monoglyceride, fatty acid diglyceride, fatty acid triglyceride, and propylene glycol.
• Fatty acid ester sucrose fatty acid ester, polyglycerin fatty acid ester, lecithin, processed starch, sorbitan fatty acid ester, Kiraya extract, Arabic gum, tragant gum, guar gum, karaya gum, xanthan gum, pectin, alginic acid and its salts, carrageenan, gelatin, casein emulsion
• An emulsified solution having excellent stability can be obtained by emulsification treatment using an emulsifier such as saponin or sodium caseinate using a homomixer, a colloid mill, a rotary disk type homogenizer, a high-pressure homogenizer or the like.
• emulsifiers used is not strictly limited and can be changed over a wide range depending on the type of emulsifier used, etc., but usually, with respect to 1 part by mass of the hydroxyaldehyde compound represented by the formula 1, A range of about 0.01 to about 100 parts by mass, preferably about 0.1 to about 50 parts by mass is suitable.
• water-soluble solvent solutions include polyhydric alcohols such as glycerin, propylene glycol, sorbitol, martitol, sucrose, glucose, trehalose, sugar solutions, and reduced water candy in order to stabilize emulsification.
• polyhydric alcohols such as glycerin, propylene glycol, sorbitol, martitol, sucrose, glucose, trehalose, sugar solutions, and reduced water candy in order to stabilize emulsification.
• One type or a mixture of two or more types can be blended.
• the emulsion thus obtained can be made into a powder formulation by drying if desired.
• sugars such as gum arabic, trehalose, dextrin, sugar, lactose, glucose, starch syrup, and reduced starch syrup can be appropriately added as needed.
• the amount of these to be used can be appropriately selected according to the characteristics desired for the powder formulation and the like.
• the fragrance composition of the present invention may further contain components usually used in the fragrance composition, if necessary.
• solvents such as water and ethanol
• fragrance reserves such as ethylene glycol, propylene glycol, dipropylene glycol, glycerin, hexyl glycol, benzylbenzoate, triethylcitrate, diethylphthalate, harcholine, medium-chain fatty acid triglyceride, and medium-chain fatty acid diglyceride.
• the agent can be contained.
• the flavoring agent composed of the hydroxyaldehyde compound represented by the formula 1 or the fragrance composition containing the flavoring agent may be blended with any article such as various consumer goods. That is, still another form of the present invention provides a consumer good comprising the flavoring agent or the flavoring composition.
• the flavor-imparting agent and the flavor composition are preferably used in cosmetics, foods and drinks as consumer goods, and are particularly preferably used in cosmetics.
• Still another form of the present invention provides a method for imparting flavor to consumer goods, which comprises blending the flavoring agent or the flavoring composition into consumer goods.
• the method for blending the flavor-imparting agent and / or the flavor composition is not particularly limited, and the flavor-imparting agent and / or the flavor composition can be blended using a method known to those skilled in the art.
• cosmetics as consumer goods include, but are not limited to, perfume products such as eau deodorant, eau de deodorant, eau de perfume, perfume; hair care products such as shampoo, rinse, hair conditioner (hair cream, pomade, etc.); Cosmetics such as foundations, lipsticks, lip creams, lip glosses, lotions, cosmetic emulsions, cosmetic creams, cosmetic gels, beauty liquids, packs; deodorants such as antiperspirant sprays, deodorant sheets, deodorant creams, and deodorant sticks.
• perfume products such as eau deodorant, eau de deodorant, eau de perfume, perfume
• hair care products such as shampoo, rinse, hair conditioner (hair cream, pomade, etc.)
• Cosmetics such as foundations, lipsticks, lip creams, lip glosses, lotions, cosmetic emulsions, cosmetic creams, cosmetic gels, beauty liquids, packs
• deodorants such as antiperspirant sprays, deodorant sheets, deodorant creams, and deodorant sticks.
• Products Inorganic salts, refreshing, carbon dioxide, skin care, enzyme, biopharmaceutical bathing agents; suntan products, sunscreen products and other tanning cosmetics; face soaps, face creams and other washing pigments, for bodies Soaps and body soaps, laundry soaps, laundry detergents, disinfectants, deodorants, softeners, kitchen detergents, cleaning detergents, disinfectants, bleaching agents, toothpaste, mouthwash and other cleaning agents; dry or wet Health and hygiene products such as tissue paper, toilet paper, masks, bandages, soaps, and wet cloths or non-pharmaceutical products; aromatic deodorants for indoors and cars; etc. may be mentioned.
• the form (dosage form) of the cosmetic product is not particularly limited.
• it can be applied to various forms such as liquid, milky, creamy, pastey, solid, and multi-layered.
• it can also be applied as a sheet agent, a spray agent, and a mousse agent.
• Such a cosmetic product containing a flavor-imparting agent composed of a hydroxyaldehyde compound represented by the formula 1 or a fragrance composition containing the same can be produced by a method known to those skilled in the art.
• the flavor-imparting agent composed of the hydroxyaldehyde compound represented by the formula 1 or the fragrance composition of the present invention containing the flavor-imparting agent is contained at an appropriate concentration as long as the desired aroma is not impaired. And may contain other additives so that they are evenly dispersed.
• the other additives are not particularly limited and known ones can be used, and examples thereof include hydrocarbons such as squalane, vaseline, and microcrystalin wax; jojoba oil, carnauba wax, octyldodecyl oleate, and phenylethyl acetate.
• Phenylethyl butyrate Phenylethyl formate, phenylethyl phenylacetate, phenylethyl isobutyrate, benzyl benzoate, phenylethyl propionate, phenylpropyl acetate and other esters; Aldehydes; Triglycerides such as olive oil, beef fat, and coconut oil; Fatty acids such as stearic acid, oleic acid, and lithinoreic acid; Alcohols such as Santalex, terpineol, tetrahydrolinalol, benzyl alcohol, phenylethyl alcohol, phenylethyldimethylcarbinol, hydroxycitronellal; higher alcohols such as oleyl alcohol, stearyl alcohol, octyldodecanol; ethylene glycol, propylene glycol , Glycerin, polyhydric alcohols such as 1,3-butane
• fragrance composition / method for improving flavor of fragrance composition
• fragrance composition can also be used as other additives in cosmetics.
• the other additives may be used alone or in combination of two or more.
• the fragrance tone of the cosmetic product is not particularly limited, and may be any fragrance tone that can be imparted by a flavor-imparting agent composed of a hydroxyaldehyde compound represented by the formula 1 or a fragrance composition containing the same.
• Citrus tone, floral tone, fuzea tone, fruity tone, green tone, woody tone, moss tone, tropical flower tone, tin orchid tone, oriental tone, cypre tone, etc. can be suitably used. More specifically, examples include, but are not limited to, lemon, orange, grapefruit, lime, yuzu, kabosu, rose, geranium, jasmine, tin orchid, hyacinth, lilac, plumeria, pineapple, mango, and peach.
• it can be preferably used for cosmetics having floral, lily of the valley, citrus, fougère, and woody scents, and particularly preferably for cosmetics having floral and lily of the valley scents.
• the concentration in cosmetics can be arbitrarily determined according to the aroma of these products, the degree of desired effect, and the like.
• the concentration of the flavor-imparting agent composed of the hydroxyaldehyde compound represented by the formula 1 is, for example, 10 ppb to 10%, preferably 1 ppm to 5%, and more preferably 100 ppm (0.01%) with respect to the total mass of the cosmetic product. ) To 3%, particularly preferably in the range of 0.05% to 2%.
• the lower limit is 10 ppb, 100 ppb, 1 ppm, 5 ppm, 10 ppm, 100 ppm, 0.05%, 0.1%, 1%, 5%
• the upper limit is 10%, 5%, 4 %, 3%, 2%, 1%, 0.1%, 100 ppm, 10 ppm, 5 ppm, 1 ppm, and 100 ppb, which are within the range of any combination of these lower and upper limits.
• preferable concentrations include, for example, 5 ppm to 4% or 5 ppm to 2% as the concentration of the flavor-imparting agent composed of the hydroxyaldehyde compound represented by the formula 1 with respect to the total mass of the cosmetic product.
• the concentration of the flavor-imparting agent composed of the hydroxyaldehyde compound represented by the formula 1 in the cosmetic product is 10 ppb or more, a high compounding effect is felt and 10%.
• the concentration may be lower than the lower limit or higher than the upper limit.
• a flavoring agent composed of a hydroxyaldehyde compound represented by the formula 1 or a fragrance composition containing the same with the cosmetics as described above, for example, the residual fragrance, the persistence and / or the fragrance of the cosmetics Improved diffusivity, imparting tin orchid, floral, and / or citrus-like fragrances, imparting fresh freshness, greenness, naturalness, transparency, volume, etc., masking offensive odors of cosmetic materials themselves, etc.
• a perfume effect including at least one of the above effects can be obtained.
• Examples of food and drink as consumer goods are not limited to these, but examples include various citrus flavors such as lemon, orange, grapefruit, lime, mandarin, mandarin orange, kabos, sudachi, hassaku, iyokan, yuzu, shikuwasa, and golden citrus.
• Various fruit flavors such as strawberry, blueberry, raspberry, apple, cherry, plum, apricot, peach, pineapple, banana, melon, mango, papaya, kiwi, pear, grape, muscat, giant peak; milk such as milk, yogurt, butter Flavor; Vanilla flavor; Various tea flavors such as green tea, tea, oolong tea, herb tea; Coffee flavor; Cola flavor; Cacao flavor; Cocoa flavor; Various mint flavors such as spearmint and peppermint; Cinnamon, chamomile, cardamon, caraway, cumin , Cloves, peppers, corianders, sunshades, perilla, ginger, staranis, thyme, peppermint, nutmeg, basil, majorum, rosemary, laurel, garlic, wasabi and other spices or herbal flavors; almonds, cashew nuts, walnuts, etc.
• Various shellfish such as, various seaweeds such as wakame, kelp, various seafood and seaweed flavors; various grain flavors such as wheat such as rice, barley, wheat, malt;
• foods and drinks having one or more flavors such as various fat flavors such as fats and oils and various fish oils.
• the flavor of the food or drink may be a food or drink that makes one feel only one of the above flavors, or may be a food or drink that makes two or more kinds of flavors feel, and even if the plurality of kinds of flavors are similar, they are different.
• the former example includes a plurality of fruit flavors such as banana, peach and apple flavors (so-called mixed fruit flavors) among the fruit flavors
• the latter example includes citrus flavors such as lemon and milk flavors.
• citrus flavors such as lemon and milk flavors. Examples include those that make you feel (such as citrus-flavored lactic acid bacteria beverages) and those that make you feel mint-flavored, citrus-flavored, and cola-flavored (such as mint- or lemon-flavored cola-flavored beverages).
• More specific food and drink examples include senbei, hail, soup stock, rice cakes, buns, sardines, bean paste, mirin, mirin, broth, jelly, castella, candy balls, biscuits, crackers, potato chips, cookies, etc.
• Confectionery such as pie, pudding, butter cream, custard cream, cream puff, waffle, sponge cake, donut, chocolate, chewing gum, caramel, candy, peanut paste and other pastes; bread, udon, ramen, Chinese noodles, sushi, Breads, noodles, rice such as Gomoku rice, fried rice, pilaf, dumpling skin, shumai skin, okonomiyaki, takoyaki, etc .
• Pickles such as those pickles; fish such as mackerel, sardines, saury, salmon, tuna, bonito, whale, curry, squid, ayu, squid such as surumeika, spear squid, crested squid, firefly squid, madako
• Livestock meat ; curry, stew, beef stew, hayashi rice sauce, meat sauce, marbo tofu, hamburger, dumplings, pot rice base, soup stock (corn soup, tomato soup, consomme soup, etc.), meat dumplings, simmered sardines, canned meat, etc.
• the concentration of the flavor-imparting agent composed of the hydroxyaldehyde compound represented by the formula 1 in the food and drink can be arbitrarily determined according to the flavor of the food and drink, the degree of the desired effect, and the like.
• the concentration of the flavor-imparting agent composed of the hydroxyaldehyde compound represented by the formula 1 may be, for example, in the range of 10 ppt to 10 ppm, more preferably 100 ppt to 10 ppm, based on the total mass of the food or drink. More specifically, the lower limit is 1 pt, 10 pp, 100 pp, 1 ppb, 10 ppb, 100 ppb, 1 ppm, and the upper limit is 10 ppm, 1 ppm, 100 ppb, 10 ppb, 1 ppb, 100 ppt. Within, but not limited to, any combination of values.
• a preferable concentration for example, 100 pt to 1 ppm or 1 ppb to 100 ppb can be mentioned as the concentration of the flavor-imparting agent composed of the hydroxyaldehyde compound represented by the formula 1 with respect to the total mass of the food or drink, and the flavor characteristics of the food or drink can be improved. It can be selected according to, but is not limited to these. Although it depends on the type and flavor of the food and drink, when the concentration of the flavor-imparting agent composed of the hydroxyaldehyde compound represented by the formula 1 in the food and drink is 10 ppt or more, a high compounding effect is felt and 10 ppm or less.
• the concentration may be lower than the lower limit or higher than the upper limit.
• a flavor-imparting agent composed of a hydroxyaldehyde compound represented by the formula 1 or a flavor composition containing the flavor-imparting agent represented by the formula 1 in foods and drinks as described above, for example, flavor enhancement of foods and drinks and bitterness such as fruit skin feeling can be imparted. It is possible to obtain a perfume effect including at least one such as giving a feeling of oil and fat like fruit skin wax, giving a feeling of volume, and giving a feeling of citrus.
• Example 1 Synthesis of hydroxyaldehyde compound represented by formula 1
• the hydroxyaldehyde compounds represented by formulas 1-1 to 1-7 are described below (1) to 1-7. It was synthesized according to the procedure of (7). Among them, the hydroxyaldehyde compounds represented by the formulas 1-3 to 1-7 synthesized by the formulas (3) to (7) are also the hydroxyaldehyde compounds represented by the formula 1'.
• the ether layer is washed successively with water, saturated aqueous sodium hydrogen carbonate solution, 5% aqueous sodium thiosulfate solution and saturated brine, dried over anhydrous magnesium sulfate, and the solvent is distilled off with an evaporator to remove 10.64 of a slightly yellow oily substance. Obtained.
• This was purified by a silica gel column (48 mm id x 36 cm L, n-hexane: ethyl acetate 15: 1 to 10: 1) to obtain 10.28 g (48.9 mmol) of the colorless oily compound 5b.
• the ether layer was washed successively with water, saturated aqueous sodium hydrogen carbonate solution, 5% aqueous sodium thiosulfate solution and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was distilled off with an evaporator to add 10.81 g of a slightly yellow oily substance. Obtained.
• the ether layer was washed successively with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was distilled off with an evaporator to obtain 11.66 g of a yellow oily substance.
• Example 2 Separation of E-form and Z-form and each aroma
• HPLC high performance liquid chromatography
• the 4E body and the 4Z body had a scent containing lily of the valley, rose, green, fruity, etc., similar to the mixture of the 4E body and the 4Z body obtained in Example 1 (1). Therefore, the 4E form and the 4Z form can be used alone as a flavoring agent.
• the 4E form alone has a scent that makes you feel the fresh flowers of lily of the valley, and has a stronger scent than the 4Z form, and is considered to be particularly useful as a flavor-imparting agent.
• the 4E body and the 4Z body have a scent containing lily of the valley, floral, green, fruity, sweetness, powder, etc., similar to the mixture of the 4E body and the 4Z body obtained in Example 1 (3). there were. Therefore, the 4E form and the 4Z form can be used alone as a flavoring agent.
• the 4E form has a stronger scent than the 4Z form and gives a scent closer to that of fresh lily of the valley flowers, and the 4E form is considered to be particularly useful as a flavor-imparting agent.
• the 4E-form and the 4Z-form had a scent containing lily of the valley, floral, acid odor, creamy, watery, etc., similar to the mixture of the 4E-form and the 4Z-form obtained in Example 1 (5). .. Therefore, the 4E form and the 4Z form can be used alone as a flavoring agent. Compared with the 4Z body, the 4E body had a scent closer to that of fresh lily of the valley flowers and had a stronger scent. The 4E form was considered to be particularly useful as a flavoring agent.
• the 4E and 4Z bodies were lily of the valley-like, powder-like, acid odor, floral, cucumber-like, alcohol-like, woody, green, and ozone-like, as in the mixture of the 4E body and the 4Z body obtained in Example 1 (6). It made me feel the scent including. Therefore, the 4E form and the 4Z form can be used alone as a flavoring agent. Compared with the 4Z body, the 4E body had a scent closer to that of fresh lily of the valley flowers and had a stronger scent. The 4E form was considered to be particularly useful as a flavoring agent.
• the 4E-form and the 4Z-form have a scent containing lily of the valley-like, floral, acid odor, green, Lozareena-like, woody, aldehyde-like, etc., similar to the mixture of the 4E form and the 4Z form obtained in Example 1 (7). It was something to make. Therefore, the 4E form and the 4Z form can be used alone as a flavoring agent. Compared with the 4Z body, the 4E body had a scent closer to that of fresh lily of the valley flowers and had a stronger scent. The 4E form was considered to be particularly useful as a flavoring agent.
• Example 3 Evaluation of aroma of hydroxyaldehyde compound represented by Formula 1 As shown in Table 1 below, a lily of the valley-like basic compounded fragrance composition was prepared.
• the hydroxyaldehyde compounds of the formulas 1-1 to 1-7 obtained in Examples 1 (1) to (7) were added to the above-mentioned tinlan-like basic blended fragrance composition as the flavor-imparting agent of the present invention in Table 2 below.
• the fragrance composition of the present invention was prepared by blending as per, and its effect was confirmed by sensory evaluation. In the sensory evaluation, the fragrance composition of the present invention was impregnated into the scent paper, and 14 well-trained perfumers with more than 10 years of experience evaluated the scent. We asked them to score based on the following evaluation criteria and comment on the quality of the aroma.
• all of the hydroxyaldehyde compounds of the formulas 1-1 to 1-7 can impart a characteristic scent excellent in lily of the valley-like fragrance as a flavor-imparting agent, and can create a high-quality fragrance reminiscent of fresh flowers. It was confirmed that it was effective.
• Example 4 Evaluation of aroma of geometric isomers
• the tinlan-like basic blended fragrance composition prepared in Example 3 was prepared by blending so as to be the total amount of the fragrance composition, and sensory evaluation was performed.
• the fragrance composition of the present invention was impregnated into odor paper, and seven well-trained perfumers with more than 10 years of experience were given a score for the quality of lily of the valley-like fragrance in the same manner as in Example 3. I let you.
• the average results of the sensory evaluation are shown in Table 3 below.
• the compound of the formula 1-1 and the compound of the formula 1-2 have an effect of imparting an excellent aroma even in a mixture of the E-form and the Z-form (see also Example 3), but the formula 1 It was confirmed that the 4E compounds of -1 and the 4E and 8E compounds of formula 1-2 exert particularly excellent effects.
• Example 5 Formulation example 1 in cosmetics
• the hand soap of the present invention was prepared by blending so as to have a concentration of 1% and 1% (total amount of hand soap), and packed in a commercially available empty push-type hand soap bottle. Then, five well-trained perfumers with more than 10 years of experience wash their hands in lukewarm water (about 35 ° C) using one push of a hand soap bottle (about 1 mL) in a closed laboratory.
• each of the hydroxyaldehyde compounds of the formulas 1-1 to 1-7 as a flavor-imparting agent, not only the scent quality of natural feeling but also the diffusibility and residual fragrance can be improved. It was confirmed that it would play.
• Example 6 Example 2 of compounding in cosmetics
• Each of the hydroxyaldehyde compounds of the formulas 1-1 to 1-7 obtained in Examples 1 (1) to (7) can be used as a flavor-imparting agent of the present invention in a commercially available lemon-like perfume, mango-like perfume, or ozone.
• the cosmetic product of the present invention was obtained by blending a perfume for men with a concentration of 300 ppm with respect to the total amount of the perfume. Then, the cosmetic product of the present invention was subjected to a sensory evaluation by seven well-trained perfumers with more than 10 years of experience.
• hydroxyaldehyde compounds of the formulas 1-1 to 1-7 can remarkably improve various aromas as a flavor-imparting agent.
• Example 7 Example of blending into food and drink Each hydroxyaldehyde compound of the formulas 1-1 to 1-7 obtained in Examples 1 (1) to (7) is commercially available as a flavor-imparting agent of the present invention.
• the beverage of the present invention was prepared by blending 50% of the fruit juice of lemonade with a concentration of 1 ppb (to the total amount of lemonade). Then, five panelists with more than 10 years of experience were asked to comment on the flavor of the beverage of the present invention as compared with the above-mentioned commercially available lemonade to which the flavor-imparting agent of the present invention was not added.
• the flavor-imparting agent of the present invention can impart a characteristic flavor to foods and drinks and is also useful as a flavoring compound for foods and drinks.

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