JP6576973B2 - Residual odor enhancer - Google Patents

Description

  The present invention relates to a residual fragrance improver containing rotandon and 4- (4-methyl-3-pentenyl) -2 (5H) -furanone as active ingredients, and further, a residual fragrance compounded with the residual fragrance improver. The present invention relates to a high fragrance composition, and a consumer product with high residual fragrance, containing the residual fragrance enhancer or the fragrance composition.

  Consumer demand for various consumer goods such as food and drink, cosmetics, pharmaceuticals, and hygiene products extends to the aroma of products. Up until now, consumers have been demanding aromas rich in natural and freshness due to the rise in natural orientation, but recently, in addition to these, there is a demand for products with high residual fragrance properties that last a long time. It is growing.

  Until now, in order to obtain a high residual fragrance property, fragrance compositions of various formulations have been proposed. For example, it has been proposed that a compound having an effect of suppressing volatilization of a fragrance compound, that is, a so-called fragrance retention agent, be added to the fragrance composition (Patent Documents 1 to 3). However, each fragrance retention agent has problems such as degradation of the fragrance characteristics of the fragrance composition due to the fragrance of the fragrance retention agent, and the applicable fragrance tone is limited. Moreover, the persistent perfume raw material of the prescription which employ | adopted the fragrance | flavor compound which has a specific LogP value as a highly residual fragrance | flavor composition for softening agents is proposed (patent document 4). In addition, a perfume composition having a prescription obtained by performing a washing test and an aroma sensory evaluation to identify a combination of perfume compounds having a high residual fragrance by specifying a combination of perfume compounds having a high residual scent by a LogP value alone It has been proposed (Patent Document 5). However, these fragrance compositions are limited to the fragrance preferred by softeners, and focus only on the residual fragrance when remaining in clothing, and are limited applications that meet the diverse demands of consumers. It is not wide and adequate.

  Therefore, development of a residual scent improvement agent having a high residual scent improvement effect and versatility is awaited.

  On the other hand, rotandon ((3S, 5R, 8S) -3,8-dimethyl-5- (prop-1-en-2-yl) -3,4, which is an active ingredient of the aftertaste improver of the present invention. , 5,6,7,8-hexahydroazuluen-1 (2H) -one) is a compound isolated and structure-determined from a tuber of the cyperaceae called Kobushi as a herbal medicine (non-patent literature) 1) It is also known as a Chinese herbal medicine in China and as an ingredient in agarwood used in incense in Japan (Non-patent Document 2). Moreover, since it has a repellent effect on insects, its use as a pest repellent (Patent Document 6) and a pest control agent (Patent Document 7) has also been reported. In recent years, rotandon has been the causative component of spicy and peppery aromas in Shiraz wine and grapes for its wines, which are characterized by spicy and peppery aromas. It has been reported that it is an important aroma component and is contained in a small amount in spices such as marjoram, oregano, rosemary, basil, and thyme (Non-patent Document 3). Further, in recent years, the citrus flavor enhancement effect of rotandon (Patent Document 8) and the fruit flavor enhancement effect (Patent Document 9) have been confirmed.

  Another active ingredient of the present invention, 4- (4-methyl-3-pentenyl) -2 (5H) -furanone (4- (4-methyl-3-pentenyl) -2 (5H) -furanone), It is known as acarid mite secretion (Non-patent Document 4).

Japanese Patent No. 5645389 Japanese Patent No. 5829438 Japanese Patent No. 5911480 Japanese Patent No. 3102893 Japanese Patent No. 4220233 Japanese Patent Laid-Open No. 4-321613 JP-A-6-16516 JP 2006-198025 A Japanese Patent Laid-Open No. 2006-198026

Tetrahedron Letters, 1967, Vol. 8, No. 47, p. 4661-4667 Phytochemistry, 1991, Vol. 30, No. 10, p. 3343-3347 Journal of Agricultural and Food Chemistry, 2008, 56, 10, p. 3738-3744 Biosci. Biotechnol. Biochem. 2002, Vol. 66, No. 1, p. 135-140

  The subject of this invention is providing the novel fragrance improvement agent which can improve these fragrance properties by mix | blending with consumer goods, such as a fragrance | flavor composition, food-drinks, and cosmetics.

  While the present inventors diligently researched to solve the above problems, rotandon and 4- (4-methyl-3-pentenyl) -2 (5H) -furanone were blended in a fragrance composition, resulting in high residual fragrance properties. In addition, there was a completely unexpected result that there was no suggestion or report so far that a significantly higher residual fragrance property was obtained than in the case of blending each singly. The inventors of the present invention have further researched, and various fragrances using a fragrance composition containing rotandon and 4- (4-methyl-3-pentenyl) -2 (5H) -furanone as active ingredients as a residual fragrance improver. By adding it to various consumer goods such as fragrance compositions, foods and drinks, and cosmetics, these residual fragrance properties can be dramatically improved, and aroma characteristics can also be improved by enhancing naturalness, freshness, volume, etc. I found.

Thus, the present invention provides the following.
[1] A residual fragrance improver containing rotandon and 4- (4-methyl-3-pentenyl) -2 (5H) -furanone as active ingredients.
[2] The aftertaste improver according to [1] is 0.1 ppt to 1000 ppm in terms of mass concentration as rotandon and 0 in terms of mass concentration as 4- (4-methyl-3-pentenyl) -2 (5H) -furanone. A perfume composition containing 1 ppm to 1000 ppm.
[3] The fragrance composition according to [2], wherein the fragrance is floral, citrus, or fruit.
[4] The aftertaste improver according to [1] is 0.001 ppt to 10 ppm in terms of mass concentration as rotandon and 0 in terms of mass concentration as 4- (4-methyl-3-pentenyl) -2 (5H) -furanone. A consumer good containing 0.001 ppm to 10 ppm.
[5] The consumer good according to [4], wherein the incense tone is a floral tone, a citrus tone, or a fruit tone.
[6] A method for improving the residual fragrance property of a fragrance composition or consumer goods, comprising adding the residual fragrance improver according to [1] to the fragrance composition or consumer goods.

  The present invention provides a novel aftertaste improver comprising rotandon and 4- (4-methyl-3-pentenyl) -2 (5H) -furanone as active ingredients. The residual scent improver of the present invention can be significantly improved in the fragrance composition and various consumer goods by blending it with various fragrance compositions and various consumer goods, The aroma characteristics of the fragrance composition and various consumer goods can be improved by enhancing natural feeling, fresh feeling, volume feeling and the like.

(Active ingredient of the aftertaste improver of the present invention)
The aftertaste improver of the present invention includes rotandon, 4- (4-methyl-3-pentenyl) -2 (5H) -furanone (4- (4-methyl-3-pentenyl) -2 (5H) -furanone, The following two compounds are used as active ingredients. Rotandon is a compound represented by the following formula (1), and MPF is a compound represented by the following formula (2).

  The two active ingredients of the present invention can be obtained by various methods. Rotandon can be synthesized, for example, by the method described in Non-Patent Document 3 above, or can be obtained from commercially available pepper essential oil by a fractionation method alone or in combination with a distillation method and a column chromatogram method. MPF can be obtained, for example, by a synthesis method described in Non-Patent Document 4 in five steps using α-bromo-γ-butyrolactone as a raw material.

  The mass ratio of rotandon and MPF in the aftertaste improver of the present invention is not particularly limited, and the effect of the present invention depends on the fragrance to be blended with the aftertaste improver of the present invention, the degree of desired aftertaste, and the like. Can be arbitrarily determined within the range in which For example, examples of suitable mass ratios of rotandon to MPF include 500: 1, 300: 1, 100: 1, 80: 1, 60: 1, 50: 1, 40: 1, 30: 1, 20: 1, 10: 1, 5: 1, 3: 1, 2: 1, 1: 1, 1: 2, 1: 3, 1: 5, 1:10, 1:20, 1:30, 1:40, 1: 50, 1:60, 1:80, 1: 100, 1: 300, and 1: 500 are included in the range of any two. Specific examples of suitable mass ratios are 1:50 to 50: Examples include, but are not limited to, 1, 1: 5 to 30: 1, 20: 1 to 1:20, 15: 1 to 1:15, and 10: 1 to 1:10. In the present specification, “to” means a numerical range including a lower limit value and an upper limit value.

  Here, in the present invention, the effect of improving the residual fragrance is compared with the case where the residual fragrance improving agent of the present invention is added to various consumer goods such as a fragrance composition, food and drink, and cosmetics, as compared with the case where it is not added. It means the effect of maintaining the fragrance characteristics and the intensity of fragrance of a fragrance composition or consumer goods for a longer time. The method for confirming the aroma characteristic and the intensity of the aroma is not particularly limited. For example, the determination may be based on a sensory evaluation based on human olfaction, or the fragrance may be determined by any odorous compound determination means such as a gas chromatograph-mass spectrometer. The amount of the aromatic compound released from the composition may be measured and determined based on the measured value.

(Perfume composition containing the remaining fragrance improving agent of the present invention)
The residual fragrance improver of the present invention can remarkably enhance the residual fragrance of the fragrance composition by blending in the fragrance composition, and further, the fragrance characteristics of the fragrance composition, for example, natural feeling, fresh feeling, The volume feeling can be improved. That is, the fragrance composition blended with the residual fragrance improving agent of the present invention becomes a highly fragrant fragrance composition, and has excellent aroma characteristics rich in natural feeling, fresh feeling, volume feeling, and the like.

  The concentration in the fragrance composition of the residual fragrance improver of the present invention is not particularly limited, and is arbitrary as long as the effect of the present invention is obtained depending on the fragrance of the fragrance composition to be blended, the desired degree of residual fragrance, and the like. For example, 0.05 ppt, 0.1 ppt, 1 ppt, 5 ppt, 10 ppt, 50 ppt, 75 ppt, 100 ppt, 250 ppt, 500 ppt, 750 ppt, 1 ppb, 5 ppb, 10 ppb, as the lower limit of the mass concentration range in the fragrance composition 50 ppb, 100 ppb, 250 ppb, 500 ppb, 750 ppb, 1 ppm, 5 ppm, 10 ppm, 50 ppm, 100 ppm, 500 ppm, and upper limit 3000 ppm, 2000 ppm, 1000 ppm, 500 ppm, 100 ppm, 80 ppm, 70 ppm, 50 ppm 30 ppm, 10 ppm, 5 ppm, 1 ppm, 750 ppb, 500 ppb, 250 ppb, 100 ppb, 80 ppb, 50 ppb, 30 ppb, 10 ppb, 5 ppb, 1 ppb, 750 ppt, 500 ppt, 250 ppt, 100 ppt, 80 ppt, 70 ppt, 50 ppt, 10 ppt, 50 ppt, 10 ppt The residual fragrance improver of the present invention can be blended in the fragrance composition so as to be contained at a concentration within the range consisting of any combination of 5 ppt. In addition, although depending on the fragrance tone and fragrance characteristics of the fragrance composition to be blended, both rotandon and MPF may be insignificant at 0.05 ppt or less, so that the effects of blending may not be obtained. And MPF has a strong fragrance, which may alter the fragrance characteristics of the fragrance composition to be blended and give a sense of discomfort. Examples of suitable concentrations include, but are not limited to, within the range of 100 ppt to 1000 ppm, 1 ppb to 500 ppm, and 10 ppb to 100 ppm for both rotandon and MPF.

  The form of the fragrance composition in which the residual fragrance improving agent of the present invention is blended is not particularly limited, and examples thereof include a water-soluble fragrance composition, an emulsified fragrance composition, and a powder fragrance composition, which may be liquid or solid.

  Such a fragrance composition is not particularly limited, and may be a fragrance composition prepared by arbitrarily combining the following synthetic fragrance compounds and / or natural fragrances.

  Synthetic fragrance compounds include, for example, α-pinene, β-pinene, myrcene, camphene, oximene, limonene, α-ferrandrene, terpinene, 3-carene, bisabolen, valencene, cedrene, caryophyllene, longifolene, 1,3,5 Hydrocarbons such as undecatriene; butanol, pentanol, hexanol, 3-heptanol, 1-undecanol, 2-undecanol, 1-dodecanol, (Z) -3-hexen-1-ol, 2,6-nonadienol , Prenol, dihydrolinalool, 10-undecen-1-ol, linalool, nerol, geraniol, citronellol, myrsenol, dihydromyrcenol, tetrahydromyrcenol, farnesol, nerolidol, cedrol, osmenol, terpineo , Alcohol, such as benzyl alcohol, 3-tanol, β-phenylethyl alcohol, α-phenylethyl alcohol, cinnamic alcohol, eugenol, isoeugenol, dimethylbenzylcarbinol; acetaldehyde, hexanal, heptanal, octanal, nonanal, 2 -Methyloctanal, 3,5,5-trimethylhexanal, decanal, undecanal, 2-methyldecanal, dodecanal, tridecanal, tetradecanal, trans-2-hexenal, trans-4-decenal, cis-4- Desenal, trans-2-decenal, 10-undecenal, trans-2-undecenal, trans-2-dodecenal, 3-dodecenal, trans-2-tridecenal, 2 4-hexadienal, 2,4-decadienal, 2,4-octadienal, 2,4-dodecadienal, 5,9-dimethyl-4,8-decadienal, citral, citronellal, lyial, dimethyloctanal, α- Aldehydes such as methylene citronellal, citronellyloxyacetaldehyde, myrtenal, neral, mylacaldehyde, α- or β-sinensal, phenylacetaldehyde, amylcinnamic aldehyde, benzaldehyde, cinnamylaldehyde, vanillin, ethyl vanillin, heliotropin Octanal dimethyl acetal, nonanal dimethyl acetal, decanal dimethyl acetal, decanal diethyl acetal, 2-methylundecanal dimethyl acetal, Acetals such as ral dimethyl acetal, citral diethyl acetal, citral propylene glycol acetal; 2-heptanone, 3-heptanone, 3-octanone, 1-octen-3-one, 2-nonanone, 2-undecanone, 2-tridecanone, methylheptenone , Dimethyloctenone, geranylacetone, 2,3,5-trimethyl-4-cyclohexenyl-1-methyl ketone, neron, nootkatone, dihydronootkatone, acetophenone, 4,7-dihydro-2-isopentyl-2-methyl-1 , 3-dioxepin, α or β-ionone, α-isomethylionone, acetoin, diacetyl, 2,3-pentanedione, maltol, ethylmaltol, 2,5-dimethyl-4-hydroxy-3 (2H) -furanone , Hydroxyketones, carvone, menthone, β-damasenone, ketones; propyl formate, octyl formate, linalyl formate, citronellyl formate, geranyl formate, neryl formate, terpinyl formate, ethyl acetate, isopropyl acetate, amyl acetate, isoamyl acetate Cis-3-hexenyl, trans-2-hexenyl acetate, octyl acetate, nonyl acetate, decyl acetate, dodecyl acetate, dimethylundecadienyl acetate, osmenyl acetate, myrcenyl acetate, dihydromyrcenyl acetate, linalyl acetate, citronellyl acetate, acetic acid Geranyl, neryl acetate, tetrahydromugol acetate, lavandulyl acetate, nerolidol acetate, dihydrocuminyl acetate, terpinyl acetate, citryl acetate, nopyr acetate, dihydroterpinyl acetate, 2,4-dimethyl-3-cycloacetate Xenyl methyl, miraldyl acetate, beticol acetate, benzyl acetate, decenyl propionate, linalyl propionate, linalyl propionate, geranyl propionate, neryl propionate, terpinyl propionate, tricyclodecenyl propionate, styryl propionate, amyl butyrate, Octyl butyrate, neryl butyrate, cinnamyl butyrate, amyl valerate, isopropyl isobutyrate, octyl isobutyrate, linalyl isobutyrate, neryl isobutyrate, linalyl isovalerate, terpinyl isovalerate, phenylethyl isovalerate, 2-methylvalerate 2-methylpentyl, ethyl caproate, methyl 3-hydroxyhexanoate, ethyl 3-hydroxyhexanoate, ethyl heptanoate, methyl octoate, octyl octoate, linalyl octoate, nonanoic acid Esters such as chill, methyl undecylenate, linalyl benzoate, methyl cinnamate, isoprenyl angelate, methyl gellanate, triethyl citrate, methyl salicylate; phenols such as thymol, carvacrol, β-naphthol isobutyl ether; γ Lactones such as -decalactone, γ-dodecalactone, δ-decalactone, γ-undecalactone, δ-dodecalactone, 7-decen-4-olide, 2-decen-5-olide; acetic acid, propionic acid, butyric acid, Acids such as valeric acid, hexanoic acid, octanoic acid, decanoic acid, dodecanoic acid, 2-decenoic acid, and gellanic acid; skatole, pyridine, methyl anthranilate, ethyl anthranilate, methyl N-methylanthranilate, N-2'- Methylpentylidene methyl anthranilate, Ligantra , Dodecanenitrile, 2-tridecenenitrile, geranylnitrile, citronellilnitrile, 3,7-dimethyl-2,6-nonadienonitrile, indole, 5-methyl-3-heptanone oxime, thiogeraniol, limonenethiol , P-menthyl-8-thiol, methanethiol, dimethyl sulfide, dimethyl disulfide, allyl isothiocyanate and other nitrogen-containing / sulfur-containing compounds; furfuryl alcohol, furfural, rose oxide, linalool oxide, mentfuran, theaspirane, etc. -Ether compounds; However, it is not limited to these.

  Examples of synthetic fragrance compounds that can be suitably used in floral tones include phenyl ethyl alcohol, β-damasenone, rose oxide, rose furan, β-ionone, α-isomethylionone, carvone, Roll oxide, β-damascone, δ-damascone, 3- (4,8-dimethyl-3,7-nonadienyl) thiophene, 4- (4-methyl-3-pentenyl) -1,2 dithiacyclohex-4- Ene, 1,2-epithiooffmulene, 4,5-epithiooffmulene, 4,5-epithiocaryophyllene, eugenol, geraniol, linalool, nerol, lyrial, neryl acetate, citronellyl acetate, α-terpineol, farnesol, benzaldehyde, citronellol, citronellal Geranyl acetate, Methyl acetate, benzyl acetate, isoamyl acetate, hydroxycitronellal, etc .; if jasmine, phenylethyl alcohol, methyl jasmonate, cis-jasmon, jasmine lactone, benzyl acetate, geranyl linalool, hydroxycitronellal, cinnamic acid Benzyl, cinnamic alcohol, methyl anthranilate, linalyl acetate, benzyl butyrate, benzyl salicylate, terpineol; if Lily, p-cresol, phenylethyl acetate, phenylethyl cinnamate, linalyl cinnamate, amyl benzoate, salicylic acid Benzyl, isobutyl phenylacetate, isobutyl salicylate, isoeugenol, phenylpropyl alcohol, phenylpropylaldehyde; lilac Synthetic alcohol, phenylethyl alcohol, anisic aldehyde, linalool, heliotropin, terpineol, hydroxycitronellal, cyclamenaldehyde; if lavender, linalool, linalyl acetate, camphor, caryophyllene, terpineol, γ-terpinene ; If it is ylang-ylang, linalool, benzyl benzoate, farnesol, methyl benzoate, benzyl acetate, geranyl acetate, p-cresyl methyl ether, caryophyllene, etc. may be mentioned, but not limited thereto.

  Examples of natural fragrances include natural fragrances obtained by pressing, solvent extraction, steam distillation, etc., and more specifically sweet orange, bitter orange, petit glen, lemon, bergamot, mandarin, neroli, Peppermint, spearmint, lavender, chamomile, rosemary, eucalyptus, sage, basil, rose, geranium, jasmine, lily, lilac, hyacinth, ylang ylang, anise, clove, ginger, nutmeg, cardamom, cedar, cypress, sandalwood, cedarwood Natural essential oils such as, but not limited to, galvanum, vetiver, patchouli, labdanum, citronella, geranium, lavandin and the like.

  In addition, in the fragrance composition containing the aftertaste improver of the present invention, a solvent suitable for dissolving the above various materials, for example, ethyl alcohol, glycerin, propylene glycol, dipropylene glycol, triacetin, citric acid Triethyl, isopropyl myristate, diethyl phthalate, diisobutyl adipate, diethylene glycol monobutyl ether, diethylene glycol monoethyl ether, dipropylene glycol monomethyl ether, hexylene glycol, medium chain fatty acid glycerin ester, edible oils such as edible vegetable oil, or animal fats Etc. can be blended.

(Various consumer goods blended with the residual fragrance improver of the present invention)
The aftertaste improver of the present invention can be blended with any consumer goods such as cosmetics, foods and drinks, pharmaceuticals, and hygiene products to improve their aroma properties and further improve their aroma characteristics. it can. The improvement of the aroma characteristic is, for example, imparting an aroma or flavor overflowing with a natural feeling, a fresh feeling, a body feeling and the like. The residual fragrance improving agent of the present invention may be blended in an effective amount directly into a consumer good, but preferably, an effective amount of a highly residual fragrance composition blended with the residual fragrance improving agent of the present invention is blended in a consumer good. To do.

  The blending amount of the aftertaste improver of the present invention or a perfume composition containing the same into consumer goods such as cosmetics and foods and drinks depends on the perfume tone of the perfume composition to be blended and the desired residual perfume level. Thus, it can be arbitrarily determined within a range where the effects of the present invention can be obtained. For example, as the mass concentration of rotandon and MPF, for example, 0.0005 ppt, 0.001 ppt, 0.01 ppt, 0.05 ppt, 1 ppt, 5 ppt, 10ppt, 25ppt, 50ppt, 75ppt, 100ppt, 1ppb, 5ppb, 10ppb, 50ppb, 100ppb, 250ppb, 500ppb, 750ppb, 1ppm, 5ppm, and upper limit of 10ppm, 5ppm, 1ppm, 750ppb, 500ppb, 250ppb, ppp, 250ppb, 80ppb, 50ppb, 30ppb, 10ppb, 5ppb, 1ppb, 750ppt, 500ppt, 250ppt, 100ppt, 80ppt, 70ppt, 50ppt, 10pp 5 ppt, 1 ppt, 0.5 ppt, 0.1 ppt, 0.05 ppt, 0.01 ppt so that it is contained at a concentration within the range of any combination, or a fragrance blended with the same The composition can be incorporated into consumer goods. Although depending on the scent of consumer goods such as cosmetics or foods and drinks, both rotandon and MPF may be insignificant at 0.0005 ppt or less, and there is a risk that the effect of the blending cannot be obtained. Has a strong aroma, and may change the aroma characteristics of the fragrance composition to be blended to give a sense of incongruity. As an example of a suitable concentration, the mass concentration of rotandon and MPF is 0.001ppt to 1ppm, 0.01ppt to 100ppb, and 0.1ppt to 100ppb with respect to the total mass of consumer goods such as cosmetics and foods and drinks. Within the range, it is not limited to these.

  Such cosmetics and food / beverage products are not particularly limited, and the residual fragrance improving agent of the present invention can be used in various cosmetics or food / beverage products in a wide field. Cosmetics include, for example, fragrance products such as perfume, eau de parfum, eau de toilette, eau de cologne; hair care products such as shampoos, rinses, hair creams, pomades, hair sprays, hair nourishing agents; Foundation, makeup, lipstick, lip balm and other basic or makeup cosmetics; soaps, laundry detergents, disinfecting detergents, deodorant detergents, etc .; toothpaste, tissue, toilet paper and other hygiene products; indoor air fresheners, Aromatic products such as car colons; Examples of the food and drink include fruit drinks such as fruit juice drinks and vegetable drinks; carbonated drinks such as cola drinks, carbonated drinks containing fruit juices, and carbonated drinks containing milk; sports drinks, honey drinks, soy milk, vitamin supplement drinks , Mineral drinks, nutrition drinks, nutrition drinks, and other food drinks; lactic acid bacteria drinks and other milk drinks; green tea, black tea, oolong tea, herbal tea, coffee drinks, non-alcoholic chu-hi, non-alcoholic cocktails, non-alcoholic wines, non Taste beverages such as alcohol beer; alcoholic beverages such as Chuhai, cocktail drinks, sparkling liquor, fruit liquor, condiment liquor; desserts such as ice cream, ice milk, lact ice, ice confectionery, yogurt, pudding, jelly, daily dessert; Caramel, candy, tablet confectionery, crackers, beer It can be given food and drink and the like; packets, cookies, pies, chocolate, confectionery, such as a snack; bread, cake mixes, dessert mixes, various instant foods such as soup.

  The fragrance of the fragrance composition or the consumer goods that can improve the fragrance property with the fragrance property improving agent of the present invention is not particularly limited. For example, “Patent Gazette Known and Conventional Techniques (Fragrance) Part II Food Fragrances (issued in 12.1.2014)” and “Patent Office Gazette Known and Conventional Techniques (Fragrance) Part III For Cosmetics” Fragrances described in “Perfume (issued in Heisei 13.6.15)” can be mentioned. More specifically, the fragrance of cosmetics, pharmaceuticals, health and hygiene products or fragrance compositions to be incorporated therein includes lemon, orange, grapefruit, lime, yuzu, sudachi, bergamot, tangerine, mandarin, etc .; apple , Banana, Pineapple, Strawberry, Grape, Peach, Pear, Tropical Fruit, etc .; Green, Galvanam, Violet Leaf, etc .; Floral, Rose, Jasmine, Ylang Ylang, Hyacinth, Muguet, Lilac, Lavender, Lily, etc .; Aldehyde tone; Spice tone such as clove, pepper, cassia and nutmeg; Woody tone such as sandalwood and cedarwood; Sweet tone such as ethyl vanillin and maltol; Moss tone such as oak moss; Pow such as coumarin and vanillin Lee tone; balsam tone such as Peruvian balsam, trouser balsam; musk tone such as muskons and nitromusks; amber tone such as ambroxan; animal tone such as civet; anise tone such as star anise; marine tone; peppermint, spearmint etc. Examples include mint tone, leather tone, honey tone, earthy tone, and the like. Among them, floral tone, citrus tone, and fruit tone are preferable examples, but not limited thereto.

  The scent of lemon and orange, grapefruit, lime, yuzu, sudachi, mandarin orange, apple, grape, strawberry, pineapple, banana, peach, melon, apricot, ume , Raspberry, blueberry, cranberry, blackberry, pear, plum, tropical fruit, etc .; milk, butter, cheese, cream, yogurt, etc .; milk, vanilla; green tea, tea, oolong tea, etc .; coffee Cocoa, chocolate and other cocoa; peppermint, spearmint, mint, mint; cinnamon, chamomile, cardamom, caraway, cumin, cloves, pepper, coriander, salamander, perilla, ginger, star anise, thyme Spices or herbals such as pepper, nutmeg, basil, marjoram, rosemary, laurel, wasabi; nuts such as almond, cashew, walnut; meats such as beef, pork, chicken; Seafood like scallops; shellfish like shrimp and crab; seasonal like bonito and bonito; seaweed like kombu, wakame and seaweed; wine, brandy, whiskey, lamb, gin, liqueur, sake Alcohol, shochu, beer, etc .; Vegetables such as onion, garlic, leek, tomato, carrot, cabbage, burdock, shiitake, matsutake, celery, honey bee; flower tone such as rose, jasmine, lavender; Among them, citrus tone and fruit tone are preferable as examples of incense tone. That, but is not limited to these.

  Hereinafter, the present invention will be described more specifically with reference to examples. The present invention is not limited to these. In addition, the density | concentration as described in the following Example shall be mass concentration unless there is particular notice.

[Example 1] Effect of the residual fragrance improver of the present invention Floral tone fragrance composition (1)
The effect of improving the residual fragrance properties in various mass ratios and concentration ranges of rotandon and MPF was confirmed.

(1) Residual and aroma characteristics at various mass ratios Rotandon and MPF were blended with commercially available rose essential oil so as to have the concentrations shown in Table 1 below to prepare perfume compositions. Each fragrance composition was evaluated for residual fragrance and aroma characteristics by 10 well-trained panelists. In the evaluation, scoring was performed according to the following criteria.
(Evaluation criteria for residual fragrance)
Each fragrance composition immediately after blending is impregnated in odor paper, and the odor paper is left at room temperature for one day, and then commercially available rose essential oil (that is, not containing rotandon and MPF, hereinafter such as About the intensity of the fragrance of each fragrance composition compared to the additive-free product)
-: Unchanged +: Slightly strong ++: Strong +++: Very strong was selected.
(Evaluation criteria for aroma characteristics)
About the fragrance of each fragrance composition as compared with a commercially available rose essential oil (additive-free product) one day after impregnating each fragrance composition immediately after preparation into odor paper and leaving the odor paper at room temperature,
5 points: The natural feeling is remarkably enhanced compared to the rose essential oil, and the rose flower is clearly recalled. 4 points: The natural feeling is enhanced compared to the rose essential oil, and the scent resembles that of the rose flower. 3 points: Natural feeling is slightly enhanced compared to rose essential oil, somewhat similar to rose flower 2 points: not much different from rose essential oil 1 point: any of the rose-like fragrance balance is uncomfortable The score was selected.
In other words, the higher the number of “+” for the residual fragrance, the higher the value, and the higher the score for the fragrance characteristic, the better the fragrance characteristic that can clearly feel the natural feeling of a rose flower. . The average evaluation results for 10 well trained panelists are shown in Table 1 below.

As shown in Table 1 above, in 1: 100 to 100: 1, it was evaluated that both the remaining aroma and the natural feeling were improved compared to the additive-free rose essential oil, and further within the range of 1:50 to 50: 1. It was evaluated that the range of 1: 5 to 30: 1 was more preferable.

(2) Residual and aroma characteristics at various concentrations Next, in the mass ratio of rotandon: MPF = 1: 1 evaluated that the aftertaste and natural feeling were improved in (1) above, the concentrations of rotandon and MPF were as follows: As shown in Table 2, it was variously changed and blended with the above-mentioned commercially available rose essential oil to prepare a fragrance composition. And evaluation similar to said (1) was performed about the fragrance property and fragrance characteristic of each fragrance | flavor composition. The results are shown in Table 2 below.

As shown in Table 2 above, it was evaluated that the residual fragrance was improved and the natural feeling was felt even at a concentration of 1 ppt, and on the other hand, at 5000 ppm, the influence of the aromas of rotandon and MPF was great and there was a sense of incongruity.

[Example 2] Effect of the residual fragrance improver of the present invention Floral tone fragrance composition (2)
A basic blended fragrance composition having a rose-like fragrance was prepared according to the general formulation shown in Table 3 below.

  In this basic blended fragrance composition (Comparative Product 1), rotandon and MPF were blended in the amounts of the rotandon mass concentration and the MPF mass concentration as shown in Table 4 below as the remaining fragrance improver of the present invention. Thus, a highly residual fragrance composition (present products 1 and 2) according to the present invention was prepared. Moreover, the fragrance | flavor composition (Comparative products 2-5) which added rotandon or MPF independently so that it might become the mass concentration shown in following Table 4 as a comparative product was also prepared.

  Subsequently, the remaining fragrance properties and the fragrance characteristics of the obtained fragrance compositions were evaluated. Specifically, for each fragrance composition immediately after the impregnation impregnated at the tip of the odor paper, an evaluation of the intensity of the fragrance and a sensory evaluation of the odor characteristics are performed by 10 well-trained panelists. These odor papers were allowed to stand at room temperature for 1 day, and then the odor intensity and sensory evaluation were performed again by the 10 panelists. As for the fragrance strength, the fragrance strength of the product 1 of the present invention 1 immediately after impregnation with odor paper is rated as a maximum of 10 points, and when the fragrance is not felt, it is 1 point (minimum score). Was calculated. The larger the score after standing at room temperature for one day and the smaller the difference from immediately after impregnation with odor paper, the higher the residual fragrance. Table 4 shows the average evaluation results of the 10 panelists.

  As shown in Table 4 above, all of the products of the present invention have a remarkably high aroma after 1 day of standing on the odor paper at room temperature. It was confirmed that the improvement was remarkable. That is, one day after leaving the odor paper, the fragrance strength of the comparative product 1 (additive-free product) is 5.0, whereas the fragrance strength of the product 1 of the present invention is 8.0 (that is, the remaining fragrance is improved). The difference in score as an effect is 3.0), which is significantly higher than the total effect of improving the residual scent of a comparative product using rotandon or MPF alone, and it was confirmed that there is a synergistic effect by the combined use of rotandon and MPF. . The same applies to the product 2 of the present invention. The products 1 and 2 of the present invention also maintained good aroma characteristics immediately after impregnation with odor paper after 1 day at room temperature. In addition, both of the products 1 and 2 of the present invention have a natural feeling reminiscent of petals of rose flowers with a gorgeous and sweet floral fragrance, either immediately after impregnation into odor paper or after standing at room temperature for 1 day. In addition, it was confirmed that it has excellent aroma characteristics as compared with any comparative product.

[Example 3] Effect of the residual fragrance improver of the present invention Floral tone fragrance composition (3)
Rotandon and MPF are blended in commercially available rose essential oil so as to have the concentrations shown in the following Table 5 as the residual fragrance improver of the present invention, and the highly residual fragrance composition according to the present invention (the present invention products 3, 4). In addition, rotandon or MPF alone was added to the rose essential oil so as to have a concentration shown in Table 5 below, to prepare a fragrance composition as a comparative product (Comparative products 7 to 10).

Subsequently, with respect to commercially available rose essential oil (additive-free product, comparative product 6) and each of the obtained fragrance compositions, evaluation of residual fragrance and sensory evaluation of fragrance were performed by 10 well-trained panelists. Evaluation of the residual fragrance property was performed in the same manner as in Example 2 (however, the fragrance intensity immediately after impregnation of the odor paper of the product 3 of the present invention was set to 10). As in Example 2, sensory evaluation of fragrance was carried out by 10 panelists for odor characteristics immediately after impregnation with odor paper and after standing for 1 day at room temperature. Each fragrance was scored according to the following criteria: I did. The higher the score, the clearer the natural feeling of roses and the better the aroma characteristics.
(Aroma evaluation criteria)
5 points: Reminiscent of fresh rose flowers, feels fresh and natural 4 points: Feels a natural scent similar to fresh rose flowers 3 points: Somewhat similar to fresh rose flowers 2 points: Rose tone Although it is fragrant, it cannot be said that it is like a flower arrangement of roses. One point: it does not feel a rose-like fragrance. The evaluation results are shown in Table 5 below.

  As shown in Table 5 above, the products 3 and 4 of the present invention in which rotandon and MPF are used in combination have remarkably higher residual fragrance than the comparative product 6 (additive-free product). It was confirmed that the residual fragrance was remarkably high even when compared with comparative products 7 to 10 used alone, and the natural feeling was also excellent.

[Example 4] Effect of the residual fragrance improver of the present invention Floral tone fragrance composition (4)
A basic blend fragrance composition having a jasmine-like fragrance was prepared according to the general formulation shown in Table 6 below.

  In this basic blended fragrance composition (Comparative Product 11), rotandon and MPF are blended so as to have the concentrations shown in Table 7 below as the remaining fragrance improver of the present invention, and the high remaining fragrance composition according to the present invention. (Invention products 5, 6) were prepared. Further, as a comparative product, rotandon or MPF was blended so as to have a concentration shown in Table 7 below to prepare a fragrance composition (Comparative products 12, 13).

  Then, the sensory evaluation by ten well-trained panelists was performed on the residual fragrance and fragrance characteristics of the product of the present invention and the comparative product in the same manner as in Example 2 (however, immediately after impregnation of the odor paper of the product 5 of the present invention) The intensity of the fragrance was 10). The results are shown in Table 7 below.

  As shown in Table 7 above, the products 5 and 6 of the present invention using rotandon and MPF in combination have remarkably higher residual fragrance than the comparative product 11 (additive-free product). It was confirmed that the residual fragrance was remarkably high even when compared with the comparative products 12 and 13 used alone, and the aroma characteristics were also excellent.

[Example 5] Effect of the residual fragrance improving agent of the present invention Citrus tone fragrance composition A basic blend fragrance composition having a lime-like fragrance was prepared according to the general formulation shown in Table 8 below, and a comparative product and (Comparative product 14).

  Moreover, the basic preparation fragrance | flavor composition which has an orange-like fragrance was prepared with the general prescription shown in following Table 9, and it was set as the comparative product (comparative product 17).

  Subsequently, rotandon and MPF were blended in these comparative products as the residual fragrance improver of the present invention so as to have the concentrations shown in Table 10 below to prepare a highly residual fragrance composition according to the present invention (this book) Inventions 7 to 10). Further, as a comparative product, rotandon or MPF alone was blended so as to have a concentration shown in the following Table 10 to prepare a fragrance composition (Comparative products 15, 16, 18, 19).

  About the residual fragrance | flavor property and fragrance characteristic of each fragrance | flavor composition, it evaluated by 10 panelists who were well trained similarly to Example 2 (however, when the fragrance is lime, this product 7 and the fragrance are In the case of orange, the intensity of fragrance immediately after impregnation of the product 9 of the present invention was 10). Table 10 shows the average evaluation results of 10 panelists.

  As shown in Table 10 above, in the lime-like fragrance composition, both of the products 7 and 8 of the present invention using rotandon and MPF are remarkably higher in residual fragrance than the comparative product 14 (additive-free product). Due to the synergistic effect of the combined use, it was confirmed that the residual fragrance was remarkably higher than those of Comparative Products 15 and 16 using rotandon or MPF alone, and the aroma characteristics were also excellent. Similarly, in the orange-like fragrance composition, the products 9 and 10 of the present invention in which rotandon and MPF are used in combination have remarkably high residual fragrance properties and excellent aroma characteristics as compared with any of the comparative products 17 to 19. It was.

[Example 6] Effect of the residual fragrance improver of the present invention Fruit-like fragrance composition A basic blended fragrance composition having a pineapple-like fragrance was prepared according to the general formulation shown in Table 11 below. (Comparative product 20).

  Moreover, the basic preparation fragrance | flavor composition which has a peach-like aroma was prepared with the general prescription shown in following Table 12, and it was set as the comparative product (comparative product 23).

  In these comparative products, rotandon and MPF were blended so as to have the concentrations shown in Table 13 below as the aftertaste improver of the present invention to prepare a highly aftertaste fragrance composition according to the present invention (the present invention). Articles 11-14). Further, as a comparative product, rotandon or MPF was blended alone so as to have a concentration shown in Table 13 below to prepare a fragrance composition (Comparative products 21, 22, 24, 25). And about the residual fragrance | flavor property and aroma characteristic of each preparation fragrance | flavor composition, it evaluated by 10 panelists who were well trained similarly to Example 2 (however, this invention product 11, when an incense tone is a pineapple, In the case where the fragrance was peach, the intensity of the fragrance immediately after impregnation of the odor paper of the product 13 was set to 10). Table 13 below shows the average evaluation results of 10 panelists.

  As shown in Table 13 above, in the pineapple-like fragrance composition, the products 11 and 12 of the present invention in which rotandon and MPF are used in combination have remarkably higher residual fragrance than the comparative product 20 (additive-free product). Due to the synergistic effect of the combined use, it was confirmed that the residual fragrance was remarkably higher than those of Comparative Products 21 and 22 using rotandon or MPF alone, and the fragrance characteristics were also excellent. Similarly, in the peach-like fragrance composition, the products 13 and 14 of the present invention using both rotandon and MPF have remarkably high residual fragrance properties and excellent aroma characteristics as compared with any of the comparative products 23 to 25. It was.

[Example 7] Effect of improving fragrance properties of the present invention Fragrance composition for cleaning agents A washing experiment was conducted using a garment cleaning agent flavored with a fragrance composition blended with the residual fragrance improving properties of the present invention. The sex was confirmed.

(Laundry simulation experiment using laundry detergent)
As shown in Table 14 below, commercially available liquid detergents for clothes, floral-like products 1 and 5 of the present invention prepared in Examples 2 and 4 (Rose-like highly residual fragrance composition and jasmine-like product, respectively) High residual fragrance composition), or comparative products 1 and 11 having no additive of the residual fragrance improver of the present invention (Rose-like basic preparation fragrance composition and jasmine-like basic preparation fragrance composition, respectively) Were blended so as to be 1% by mass with respect to the total amount of the liquid detergent for clothing, and the detergent was perfumed to prepare four types of test detergents.

  On the other hand, the flat cloth was cut into 35 cm × 70 cm (24.85 to 25.05 g), and then washed with alcohol, acetone, water and dried, and further washed with ether and dried. Next, a thermometer and a rotor were placed in a 2 liter beaker, 2 L of water was added and the temperature was adjusted to 29 ° C., 2.8 g of each test cleaning agent was added, dissolved by stirring, and a cleaning solution was obtained. Weigh the above-mentioned smooth cloth into this solution, stir by hand for 5 minutes, then rinse with running water for 2 minutes, squeeze the cloth, measure the weight, adjust the water content to 50 g, then hanger And dried in a room at a constant temperature and humidity for 6 hours.

Sensory evaluation was performed by 10 well-trained panelists on the aroma of the dried fabric. The sensory evaluation was performed on the residual fragrance and the aroma characteristics as described below.
(Confirmation of remaining fragrance)
The intensity of the scent of the cleaning agent at the time of fragrance of the clothing cleaning agent was given a maximum of 5 points, and the scent strength of the dried cloth was scored according to the following criteria in comparison with the strength of the scent. .
5 points: equivalent 4 points: slightly weakened 3 points: weakened 2 points: considerably weakened 1 point: no fragrance felt (confirmation of aroma characteristics)
The scent of the dried cloth was smelled and scored based on the following criteria as to whether a natural flower-like feeling could be felt.
5 points: Reminiscent of fresh flowers of roses or jasmine, and feels fresh, natural 4 points: Feels a natural scent similar to fresh flowers of roses or jasmine, 3 points: fresh flowers of roses or jasmine Somewhat similar, rose or jasmine-like scents: rose or jasmine-like scents but not rose or jasmine fresh flowers 1-point: no rose or jasmine-like scents It means that the higher the score, the better the quality and aroma characteristics. The average evaluation results of 10 panelists are shown in Table 15 below.

  As shown in Table 15 above, it was confirmed that all of the products of the present invention can impart a high residual fragrance property and an excellent natural feeling when compared with a comparative product even when blended with a detergent for clothing.

  As confirmed in Examples 1 to 7 above, the residual fragrance improver of the present invention has various residual fragrance compositions as a fragrance composition that can significantly improve the residual fragrance and impart an excellent natural feeling. It has excellent characteristics that can be applied to goods and consumer goods.

Claims (6)

  A residual fragrance improver containing rotandon and 4- (4-methyl-3-pentenyl) -2 (5H) -furanone as active ingredients.   The aftertaste improver according to claim 1 is 0.1 ppt to 1000 ppm in terms of mass concentration as rotandon and 0.1 ppt in terms of mass concentration as 4- (4-methyl-3-pentenyl) -2 (5H) -furanone. A perfume composition containing 1000 ppm.   The fragrance composition according to claim 2, wherein the fragrance is floral, citrus or fruit.   The aftertaste improving agent according to claim 1 is 0.001 ppt to 10 ppm in terms of mass concentration as rotandon and 0.001 ppt to mass concentration as 4- (4-methyl-3-pentenyl) -2 (5H) -furanone. Consumer goods containing 10ppm.   The consumer goods according to claim 4 whose incense tone is floral, citrus, or fruit.   A method for improving the fragrance composition of a fragrance composition or consumer goods, comprising adding the fragrance enhancer according to claim 1 to the fragrance composition or consumer goods.