JP4393824B2 - Fragrance composition - Google Patents
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- JP4393824B2 JP4393824B2 JP2003319168A JP2003319168A JP4393824B2 JP 4393824 B2 JP4393824 B2 JP 4393824B2 JP 2003319168 A JP2003319168 A JP 2003319168A JP 2003319168 A JP2003319168 A JP 2003319168A JP 4393824 B2 JP4393824 B2 JP 4393824B2
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- decenal
- fragrance
- fragrance composition
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- 239000003205 fragrance Substances 0.000 title claims description 39
- 239000000203 mixture Substances 0.000 title claims description 39
- 235000013305 food Nutrition 0.000 claims description 13
- 239000002537 cosmetic Substances 0.000 claims description 12
- 239000000796 flavoring agent Substances 0.000 claims description 11
- 235000019634 flavors Nutrition 0.000 claims description 11
- 235000013361 beverage Nutrition 0.000 claims description 9
- 239000000047 product Substances 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 235000015203 fruit juice Nutrition 0.000 description 8
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000013329 compounding Methods 0.000 description 7
- 239000002304 perfume Substances 0.000 description 7
- 239000002453 shampoo Substances 0.000 description 7
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 6
- 235000009508 confectionery Nutrition 0.000 description 6
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000001106 (2R,3S)-3-pentyloxirane-2-carbaldehyde Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 4
- WTARULDDTDQWMU-RKDXNWHRSA-N (+)-β-pinene Chemical compound C1[C@H]2C(C)(C)[C@@H]1CCC2=C WTARULDDTDQWMU-RKDXNWHRSA-N 0.000 description 3
- WTARULDDTDQWMU-IUCAKERBSA-N (-)-Nopinene Natural products C1[C@@H]2C(C)(C)[C@H]1CCC2=C WTARULDDTDQWMU-IUCAKERBSA-N 0.000 description 3
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 3
- -1 Octanal 5 Decanal Chemical compound 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- WTARULDDTDQWMU-UHFFFAOYSA-N Pseudopinene Natural products C1C2C(C)(C)C1CCC2=C WTARULDDTDQWMU-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 3
- MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 description 3
- 229930006722 beta-pinene Natural products 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229940043350 citral Drugs 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- LCWMKIHBLJLORW-UHFFFAOYSA-N gamma-carene Natural products C1CC(=C)CC2C(C)(C)C21 LCWMKIHBLJLORW-UHFFFAOYSA-N 0.000 description 3
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 3
- 238000005342 ion exchange Methods 0.000 description 3
- 235000001510 limonene Nutrition 0.000 description 3
- 229940087305 limonene Drugs 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- GRWFGVWFFZKLTI-UHFFFAOYSA-N rac-alpha-Pinene Natural products CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 235000014347 soups Nutrition 0.000 description 3
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 2
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 2
- AYQPVPFZWIQERS-SREVYHEPSA-N (Z)-oct-2-en-1-ol Chemical compound CCCCC\C=C/CO AYQPVPFZWIQERS-SREVYHEPSA-N 0.000 description 2
- 240000000560 Citrus x paradisi Species 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- 235000019482 Palm oil Nutrition 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 244000269722 Thea sinensis Species 0.000 description 2
- NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 description 2
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 2
- NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000006735 epoxidation reaction Methods 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- HIGQPQRQIQDZMP-UHFFFAOYSA-N geranil acetate Natural products CC(C)=CCCC(C)=CCOC(C)=O HIGQPQRQIQDZMP-UHFFFAOYSA-N 0.000 description 2
- HIGQPQRQIQDZMP-DHZHZOJOSA-N geranyl acetate Chemical compound CC(C)=CCC\C(C)=C\COC(C)=O HIGQPQRQIQDZMP-DHZHZOJOSA-N 0.000 description 2
- 229930007744 linalool Natural products 0.000 description 2
- KVWWIYGFBYDJQC-UHFFFAOYSA-N methyl dihydrojasmonate Chemical compound CCCCCC1C(CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-UHFFFAOYSA-N 0.000 description 2
- NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 description 2
- 239000002540 palm oil Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 235000013616 tea Nutrition 0.000 description 2
- CQCAYWAIRTVXIY-UHFFFAOYSA-N 2-(triphenyl-$l^{5}-phosphanylidene)acetaldehyde Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC=O)C1=CC=CC=C1 CQCAYWAIRTVXIY-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- 241000195940 Bryophyta Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 240000007154 Coffea arabica Species 0.000 description 1
- 239000004278 EU approved seasoning Substances 0.000 description 1
- FPVVYTCTZKCSOJ-UHFFFAOYSA-N Ethylene glycol distearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCOC(=O)CCCCCCCCCCCCCCCCC FPVVYTCTZKCSOJ-UHFFFAOYSA-N 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 240000002129 Malva sylvestris Species 0.000 description 1
- 235000006770 Malva sylvestris Nutrition 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000002386 air freshener Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 235000014171 carbonated beverage Nutrition 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- 229930003633 citronellal Natural products 0.000 description 1
- 235000000983 citronellal Nutrition 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 235000016213 coffee Nutrition 0.000 description 1
- 235000013353 coffee beverage Nutrition 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- KBCMEMOHSAQTJR-UHFFFAOYSA-N decanal octanal Chemical compound CCCCCCCC=O.CCCCCCCCCC=O KBCMEMOHSAQTJR-UHFFFAOYSA-N 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- YZPCWPMIVKWDOZ-UHFFFAOYSA-N dimethyl 2,2-dioxo-1,3,2-dioxathiolane-4,5-dicarboxylate Chemical compound COC(=O)C1OS(=O)(=O)OC1C(=O)OC YZPCWPMIVKWDOZ-UHFFFAOYSA-N 0.000 description 1
- SMVRDGHCVNAOIN-UHFFFAOYSA-L disodium;1-dodecoxydodecane;sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O.CCCCCCCCCCCCOCCCCCCCCCCCC SMVRDGHCVNAOIN-UHFFFAOYSA-L 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 235000011194 food seasoning agent Nutrition 0.000 description 1
- 235000021022 fresh fruits Nutrition 0.000 description 1
- 235000015201 grapefruit juice Nutrition 0.000 description 1
- 239000003676 hair preparation Substances 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 235000014058 juice drink Nutrition 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000020124 milk-based beverage Nutrition 0.000 description 1
- 235000011929 mousse Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 235000015205 orange juice Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 235000011962 puddings Nutrition 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000005870 sharpless asymmetric epoxidation reaction Methods 0.000 description 1
- 235000011888 snacks Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 235000013618 yogurt Nutrition 0.000 description 1
Description
本発明は、食品香料、香粧品香料等として使用可能な香料組成物に関し、詳しくは特定の香気成分を含有することにより天然感のある特有の香気香味を賦与することができる香料組成物に関する。 The present invention relates to a fragrance composition that can be used as a food fragrance, a cosmetic fragrance, and the like, and more particularly, to a fragrance composition that can impart a specific aromatic flavor with a natural feeling by containing a specific fragrance component.
トランス−４，５−エポキシ−２Ｅ−デセナールはこれまで、いくつかの方法によって合成され、その甘さのあるシトラス様の香りは、香気成分として重要であることが既に報告されている。しかし、シス−４，５−エポキシ−２Ｅ−デセナールを選択的に合成したという報告例は無く、トランス−４，５−エポキシ−２Ｅ−デセナール合成時の副生成物として構造推定されていたり(非特許文献１)、選択的エポキシ化に関する文献でトランス−エポキシ体とシス−エポキシ体の混合物として得られたという報告のみである（非特許文献２）。従って、シス−４，５−エポキシ−２Ｅ−デセナールの香調確認等がなされた事はなく、香料としての用途も知られていない。 Trans-4,5-epoxy-2E-decenal has been synthesized by several methods so far, and its sweet citrus-like fragrance has already been reported to be important as an aroma component. However, there has been no report on the selective synthesis of cis-4,5-epoxy-2E-decenal, and the structure has been estimated as a by-product during the synthesis of trans-4,5-epoxy-2E-decenal (non- Patent Document 1) is only a report regarding selective epoxidation and obtained as a mixture of trans-epoxy and cis-epoxy (Non-Patent Document 2). Therefore, the fragrance of cis-4,5-epoxy-2E-decenal has not been confirmed, and its use as a fragrance is not known.
近年、消費者の嗜好性が多様化してきていることに伴い、各種各様の商品の開発が望まれている。特に、飲食品・香粧品業界はこの傾向が強く、消費者の嗜好性に合うバラエティーに富んだ飲食品、香粧品の開発が強く要求されている。これらの要求に対して、飲食品、香粧品のひとつの原料素材である香料においても、従来から知られている香料物質だけでは充分に対応しきれていない。本発明の課題は、それぞれのニーズに対応できるようなバラエティーに富んだ香料物質を提供し、消費者の天然志向にマッチした、自然で天然感のある香気香味を賦与することができる香料組成物及びそれらを配合した飲食品、香粧品を提供することにある。 In recent years, with the diversification of consumer preferences, development of various products has been desired. In particular, this trend is strong in the food / beverage / cosmetics industry, and there is a strong demand for the development of food / beverage products and cosmetics that are rich in variety to suit consumer preferences. In response to these demands, even a perfume, which is one raw material for foods and beverages, and cosmetics, has not been able to meet the demands of conventional perfume substances alone. An object of the present invention is to provide a variety of fragrance materials that can meet each need, and to provide a natural and natural fragrance composition that matches the natural orientation of consumers. And providing foods and beverages and cosmetics containing them.
本発明者らはグレープフルーツ果汁やオレンジ果汁の香気成分の精査により、強いインパクトを与える微量成分が含まれていることを見出し、別途選択的有機合成法を用いて、その構造をシス−４，５−エポキシ−２Ｅ−デセナールと同定した。 The present inventors have found that trace components that give a strong impact are contained by scrutinizing the aroma components of grapefruit juice and orange juice, and the structure thereof is cis-4,5 using a separate selective organic synthesis method. -Identified as epoxy-2E-decenal.
さらに本発明者らは本発明化合物であるシス−４，５−エポキシ−２Ｅ−デセナールの香気香味特徴を調べた結果メタリック様、アルデヒド様、みずみずしい果汁感を想起させる等の特性を有しており、従来から知られている構造的に近い香料物質であるトランス−４，５−エポキシ−２Ｅ−デセナールと比較しても、本発明品の方がよりアルデヒド様でありかつ甘味への寄与度が高いことを見出し、シス−４，５−エポキシ−２Ｅ−デセナールを調合香料中に含有させることにより、自然で天然感のある香気香味を賦与することができる香料組成物を提供できるという新たな事実を見出し本発明を完成するに至った。 Furthermore, as a result of investigating the aroma and flavor characteristics of cis-4,5-epoxy-2E-decenal which is the compound of the present invention, the present inventors have characteristics such as reminiscent of metallic-like, aldehyde-like and fresh fruit juice. Compared with trans-4,5-epoxy-2E-decenal, which is a conventionally known structurally similar fragrance material, the product of the present invention is more aldehyde-like and contributes to sweetness. The new fact that it can provide the fragrance | flavor composition which can give a natural and natural fragrance flavor by discovering that it is high and containing cis-4,5-epoxy-2E-decenal in a preparation fragrance | flavor. And the present invention has been completed.
本発明は、シス−４，５−エポキシ−２Ｅ−デセナールを含有することを特徴とする香料組成物及びそれらを配合した飲食品、香粧品よりなる。 This invention consists of the fragrance composition characterized by containing cis-4,5-epoxy-2E-decenal, the food / beverage products which mix | blended them, and cosmetics.
本発明の香料組成物を飲食品、香粧品に配合することにより、フレッシュ感、天然感を製品に賦与することができる。 By blending the fragrance composition of the present invention into foods and drinks and cosmetics, a fresh feeling and a natural feeling can be imparted to the product.
以下、本発明について詳細に説明する。 Hereinafter, the present invention will be described in detail.
本発明は、シス−４，５−エポキシ−２Ｅ−デセナールを含有することを特徴とする香料組成物及びそれらを配合した飲食品、香粧品である。 This invention is the fragrance | flavor composition characterized by containing cis-4,5-epoxy-2E-decenal, the food / beverage products which mix | blended them, and cosmetics.
本発明で使用されるシス−４，５−エポキシ−２Ｅ−デセナールは、例えば下記反応式に示すように、２Ｚ−オクテン−１−オールをエポキシ化し、シス−２，３−エポキシオクタン−１−オールとした後、酸化することによりシス−２，３−エポキシオクタナールを得、最後にリン試薬を用いる事によりシス−４，５−エポキシ−２Ｅ−デセナールを得る事ができる。
また、エポキシ化の反応において香月−シャープレス不斉エポキシ化等を用いる事によりシス−４，５−エポキシ−２Ｅ−デセナールの両光学異性体を得ることも可能である。
但し、シス−４，５−エポキシ−２Ｅ−デセナールの合成法はこれらの方法に限定されるものではない。
It is also possible to obtain both optical isomers of cis-4,5-epoxy-2E-decenal by using Katsuki-Sharpless asymmetric epoxidation or the like in the epoxidation reaction.
However, the synthesis method of cis-4,5-epoxy-2E-decenal is not limited to these methods.
本発明の有効成分であるシス−４，５−エポキシ−２Ｅ−デセナールは単独で用いる事もできる他、他の香料と任意の割合の混合物として用いる事もできる。
シス−４，５−エポキシ−２Ｅ−デセナールを香料組成物に用いる場合、その添加量は、その目的あるいは香料組成物の種類によって異なるものの、一般的には、香料組成物全体量の０．０００００００１〜１０重量％、好ましくは０．００００１〜０．０５重量％の範囲内を例示する事ができる。使用量が０．００００１重量％より少ない場合は、その添加効果が十分に得られないおそれがあり、また、０．０５重量％よりも多い場合は、この物質の持つ個性が強く出すぎて、香料組成物全体の香りのバランスを崩してしまうおそれがある。本発明の香料組成物に配合される他の成分としては、特に制限はなく、用途や目的に応じて従来より使用されていた種々の香料素材が使用可能であり、具体的にはアルデヒド類、アルコール類、エステル類等の従来公知の香料素材があげられる。
The cis-4,5-epoxy-2E-decenal which is an active ingredient of the present invention can be used alone, or can be used as a mixture with other fragrances in an arbitrary ratio.
When cis-4,5-epoxy-2E-decenal is used in a fragrance composition, the amount of the cis-4,5-epoxy-2E-decenal varies depending on the purpose or the type of the fragrance composition, but generally it is 0.00000001 of the total amount of the fragrance composition. It can be exemplified within the range of 10 to 10% by weight, preferably 0.00001 to 0.05% by weight. If the amount used is less than 0.00001% by weight, the effect of addition may not be sufficiently obtained, and if it is more than 0.05% by weight, the individuality of this substance is too strong, There is a risk of losing the balance of the fragrance of the entire fragrance composition. As other components to be blended in the fragrance composition of the present invention, there is no particular limitation, and various fragrance materials that have been conventionally used can be used depending on the application and purpose. Specifically, aldehydes, Conventionally known perfume materials such as alcohols and esters can be mentioned.
本発明の香料組成物は、果汁飲料類、果実酒類、乳飲料類、炭酸飲料類のごとき飲料類；アイスクリーム類、シャーベット類、アイスキャンディー類のごとき冷菓類；ヨーグルト類、チーズ類のごとき発酵乳製品；和洋菓子類、焼菓子類、ジャム類、チューインガム類、パン類、コーヒー、ココア、紅茶、お茶、タバコのごとき嗜好品類；プリン類、ゼリー類、ババロア類、ムース類のごときデザート類；和風スープ類、洋風スープ類のごときスープ類；風味調味料；各種インスタント飲料乃至食品類、各種スナック食品類などに添加することにより、そのユニークな香気香味が賦与された飲食品類を提供する事ができる。 The fragrance composition of the present invention comprises beverages such as fruit juices, fruit liquors, milk beverages, carbonated beverages; frozen confections such as ice creams, sherbets and ice candy; fermentations such as yogurts and cheeses. Dairy products; Japanese and Western confectionery, baked confectionery, jams, chewing gums, breads, coffee, cocoa, tea, tea, tobacco and other favorite products; puddings, jellys, bavarois, mousses It is possible to provide foods and drinks with unique flavors by adding them to soups such as Japanese-style soups and Western-style soups; flavor seasonings; various instant beverages and foods, various snack foods, etc. it can.
また、本発明の香料組成物は、シャンプー類、ヘアクリーム類、ポマード類、その他の毛髪用化粧料、白粉、口紅、その他の化粧料、洗濯用洗剤類、消毒用洗剤類、室内芳香剤その他各種の保健・衛生材料類、医薬品などの香粧品全般に広く使用することができる。 In addition, the fragrance composition of the present invention includes shampoos, hair creams, pomades, other hair cosmetics, white powder, lipstick, other cosmetics, laundry detergents, disinfectants, indoor air fresheners, etc. It can be widely used in various cosmetics such as various health and hygiene materials and pharmaceuticals.
次に実施例を示して本発明をさらに具体的に説明するが、本発明は、これらの実施例に限定されるものではない。 EXAMPLES Next, although an Example is shown and this invention is demonstrated further more concretely, this invention is not limited to these Examples.
〔参考例１〕
シス−２，３−エポキシオクタン−１−オールの合成
m-クロロ過安息香酸３１．９ｇ（純度＞６５％）を５００ｍｌの塩化メチレンに溶解させ、これを氷冷した２Ｚ−オクテン−１−オール１２．８ｇ（０．１ｍｏｌ）の塩化メチレン溶液（１０００ｍｌ）に０〜５℃で滴下した。滴下終了後室温で２時間撹拌し反応終了を確認した後、反応液に飽和チオ硫酸ナトリウム水溶液と飽和炭酸水素ナトリウム溶液を加え、エーテルにて抽出した。有機層を飽和食塩水にて洗浄し、硫酸ナトリウムにて乾燥後減圧濃縮した。これをシリカゲルカラムクロマトグラフィーにて精製後、減圧蒸留しシス−２，３−エポキシオクタン−１−オール１４ｇを得た。
[Reference Example 1]
Synthesis of cis-2,3-epoxyoctane-1-ol
31.9 g (purity> 65%) of m-chloroperbenzoic acid was dissolved in 500 ml of methylene chloride, and this was cooled with ice in 12.8 g of 2Z-octen-1-ol (0.1 mol) in methylene chloride solution (1000 ml). ) At 0-5 ° C. After completion of the dropwise addition, the mixture was stirred at room temperature for 2 hours to confirm the completion of the reaction. A saturated aqueous sodium thiosulfate solution and a saturated sodium hydrogen carbonate solution were added to the reaction solution, and the mixture was extracted with ether. The organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. This was purified by silica gel column chromatography and then distilled under reduced pressure to obtain 14 g of cis-2,3-epoxyoctane-1-ol.
沸点１２０℃／１５ｍｍＨｇ
13Ｃ ＮＭＲ （１００ＭＨｚ，ＣＤＣｌ３，δｐｐｍ） ６０．９, ５７．４, ５７．２, ３１．６, ２８．０, ２６．３, ２２．６, １４．０
Boiling point 120 ° C / 15mmHg
13 C NMR (100 MHz, CDCl 3 , δ ppm) 60.9, 57.4, 57.2, 31.6, 28.0, 26.3, 22.6, 14.0
〔参考例２〕
シス−２，３−エポキシオクタナールの合成
シス−２，３−エポキシオクタン−１−オール２．９ｇを塩化メチレン３００ｍｌに溶解し、ここにデス−マーチン ペルヨージナンの１５％塩化メチレン溶液８５ｇを加え室温で２時間撹拌した。反応液に飽和チオ硫酸ナトリウム溶液と飽和炭酸水素ナトリウム溶液を加えた後、エーテル抽出を行い飽和食塩水にて洗浄後、硫酸ナトリウムにて乾燥し溶剤留去した。得られた粗生成物をシリカゲルカラムクロマトグラフィーにて精製後、減圧蒸留しシス−２，３−エポキシオクタナール２．４ｇを得た。
[Reference Example 2]
Synthesis of cis-2,3-epoxyoctanal 2.9 g of cis-2,3-epoxyoctane-1-ol was dissolved in 300 ml of methylene chloride, and 85 g of a 15% methylene chloride solution of Dess-Martin periodinane was added thereto at room temperature. For 2 hours. A saturated sodium thiosulfate solution and a saturated sodium hydrogen carbonate solution were added to the reaction solution, followed by ether extraction, washing with saturated brine, drying over sodium sulfate, and evaporation of the solvent. The obtained crude product was purified by silica gel column chromatography and then distilled under reduced pressure to obtain 2.4 g of cis-2,3-epoxyoctanal.
沸点８０℃／１５ｍｍＨｇ
13Ｃ ＮＭＲ （１００ＭＨｚ，ＣＤＣｌ３，δｐｐｍ） １９９．２, ５９．２, ５８．０, ３１．４, ２８．１, ２６．３, ２２．５, １３．９
Boiling point 80 ° C / 15mmHg
13 C NMR (100 MHz, CDCl 3 , δ ppm) 199.2, 59.2, 58.0, 31.4, 28.1, 26.3, 22.5, 13.9
〔参考例３〕
シス−４，５−エポキシ−２Ｅ−デセナールの合成
シス−２，３−エポキシオクタナール２．４ｇとトリフェニルホスファニリデンアセトアルデヒド５．２ｇをトルエン１１０ｍｌに加え８時間加熱還流を行った後、減圧下溶剤を留去した。残渣をヘキサンにより抽出した後、シリカゲルカラムクロマトグラフィーにて精製し、次いで減圧蒸留を行いシス−４，５−エポキシ−２Ｅ−デセナールを１．７ｇ得た。
[Reference Example 3]
Synthesis of cis-4,5-epoxy-2E-decenal 2.4 g of cis-2,3-epoxyoctanal and 5.2 g of triphenylphosphanylideneacetaldehyde were added to 110 ml of toluene and heated under reflux for 8 hours. The lower solvent was distilled off. The residue was extracted with hexane, purified by silica gel column chromatography, and then distilled under reduced pressure to obtain 1.7 g of cis-4,5-epoxy-2E-decenal.
沸点８５℃／２００Ｐａ
1Ｈ ＮＭＲ （４００ＭＨｚ，ＣＤＣｌ３，δｐｐｍ） ９．６０ (ｄ，Ｊ＝７．８Ｈｚ，１Ｈ)，６．６９ (ｄｄ，Ｊ＝１５．７，６．５Ｈｚ，１Ｈ)，６．４０ (ｄｄｄ，Ｊ＝１５．７,７．８，０．９Ｈｚ，１Ｈ)，３．６３
(ｄｄｄ，Ｊ＝６．５，４．４，０．９Ｈｚ，１Ｈ)，３．２８ (ｍ，１Ｈ)，１．６５−１．２３ (ｍ，８Ｈ)，０．９０ (ｔ，Ｊ＝７．１Ｈｚ，３Ｈ)
13Ｃ ＮＭＲ （１００ＭＨｚ，ＣＤＣｌ３，δｐｐｍ） １９２．４, １５０．６, １３５．２, ６０．２, ５５．１, ３１．５, ２７．６, ２６．０, ２２．５, １３．９
Boiling point 85 ° C / 200Pa
1 H NMR (400 MHz, CDCl 3 , δ ppm) 9.60 (d, J = 7.8 Hz, 1H), 6.69 (dd, J = 15.7, 6.5 Hz, 1H), 6.40 (ddd , J = 15.7, 7.8, 0.9 Hz, 1H), 3.63
(ddd, J = 6.5, 4.4, 0.9 Hz, 1H), 3.28 (m, 1H), 1.65-1.23 (m, 8H), 0.90 (t, J = (7.1Hz, 3H)
13 C NMR (100 MHz, CDCl 3 , δ ppm) 192.4, 150.6, 135.2, 60.2, 55.1, 31.5, 27.6, 26.0, 22.5, 13.9
〔実施例１〕
下記処方により本発明の香料組成物１を得た。
品名 配合量（重量部）
α−ピネン １
β−ピネン ５
リモネン ９３３．６
γ−タピネン ５０
オクタナール １
デカナール １
シトラール ５
リナロール １
ヌートカトン ２
シス−４，５−エポキシ−２Ｅ−デセナール ０．４
トータル １０００
[Example 1]
The perfume composition 1 of this invention was obtained by the following prescription.
Product name Compounding amount (parts by weight)
α-Pinene 1
β-pinene 5
Limonene 933.6
γ-Tapinene 50
Octanal 1
Decanal 1
Citral 5
Linalool 1
Noot Katong 2
Cis-4,5-epoxy-2E-decenal 0.4
Total 1000
〔実施例２〕
下記処方により本発明の香料組成物２を得た。
品名 配合量（重量部）
α−ピネン １０
β−ピネン ２０
リモネン ９５５
オクタナール ０．５
デカナール ３
シトラール ５
リナロール １
ゲラニルアセテート ５
シス−４，５−エポキシ−２Ｅ−デセナール ０．５
トータル １０００
[Example 2]
A perfume composition 2 of the present invention was obtained by the following formulation.
Product name Compounding amount (parts by weight)
α-Pinene 10
β-pinene 20
Limonene 955
Octanal 0.5
Decanal 3
Citral 5
Linalool 1
Geranyl acetate 5
Cis-4,5-epoxy-2E-decenal 0.5
Total 1000
〔比較例１〕
実施例１のシス−４，５−エポキシ−２Ｅ−デセナールの代わりにエチルアルコールを配合して香料組成物３を得た。
[Comparative Example 1]
Instead of cis-4,5-epoxy-2E-decenal in Example 1, ethyl alcohol was blended to obtain a fragrance composition 3.
〔実施例３〕
下記処方により本発明の香料組成物４を得た。
品名 配合量（重量部）
α−ピネン ２０
β−ピネン ８０
リモネン ５９４．５
γ−タピネン ７０
オクタナール ５
デカナール １０
シトロネラール ５
シトラール ２５
リナロール ３０
ゲラニルアセテート １０
メチルジヒドロジャスモネート １００
ガラクソライド ５０
シス−４，５−エポキシ−２Ｅ−デセナール ０．５
トータル １０００
Example 3
A perfume composition 4 of the present invention was obtained by the following formulation.
Product name Compounding amount (parts by weight)
α-Pinene 20
β-pinene 80
Limonene 594.5
γ-Tapinene 70
Octanal 5
Decanal 10
Citronellal 5
Citral 25
Rinaroll 30
Geranyl acetate 10
Methyl dihydrojasmonate 100
Garaxoride 50
Cis-4,5-epoxy-2E-decenal 0.5
Total 1000
〔比較例２〕
実施例３のシス−４，５−エポキシ−２Ｅ−デセナールの代わりにエチルアルコールを配合して香料組成物５を得た。
[Comparative Example 2]
Perfume composition 5 was obtained by blending ethyl alcohol in place of cis-4,5-epoxy-2E-decenal of Example 3.
〔実施例４〕
下記処方により本発明の果汁飲料１を得た。
品名 配合量（重量部）
１／６グレープフルーツ混濁果汁 ２００
香料組成物１ ０．００５
イオン交換水 ７９９．９９５
トータル １０００
Example 4
The fruit juice drink 1 of this invention was obtained by the following prescription.
Product name Compounding amount (parts by weight)
1/6 grapefruit turbid juice 200
Fragrance composition 1 0.005
Ion exchange water 799.995
Total 1000
〔実施例５〕
下記処方により本発明の果汁飲料２を得た。
品名 配合量（重量部）
１／６オレンジ混濁果汁 ２００
香料組成物２ ０．００５
イオン交換水 ７９９．９９５
トータル １０００
Example 5
The fruit juice drink 2 of this invention was obtained by the following prescription.
Product name Compounding amount (parts by weight)
1/6 orange turbid juice 200
Fragrance composition 2 0.005
Ion exchange water 799.995
Total 1000
〔比較例３〕
下記処方により果汁飲料３を得た。
品名 配合量（重量部）
１／６グレープフルーツ混濁果汁 ２００
香料組成物３ ０．００５
イオン交換水 ７９９．９９５
トータル １０００
[Comparative Example 3]
A juice drink 3 was obtained according to the following formulation.
Product name Compounding amount (parts by weight)
1/6 grapefruit turbid juice 200
Fragrance composition 3 0.005
Ion exchange water 799.995
Total 1000
〔実施例６〕
下記処方に従い本発明のシャンプー１を得た。
品名 配合量（重量部）
ポリオキシエチレン（２）ラウリルエーテル
硫酸ナトリウム ９.０
ラウリル硫酸ナトリウム ４.０
ヤシ油脂肪酸アミドプロピルベタイン ３.０
高重合メチルポリシロキサン ２.０
メチルポリシロキサン １.０
ヤシ油脂肪酸モノエタノールアミド １.０
プロピレングリコール ２.０
塩化Ｏ−[２−ヒドロキシ−３−トリメチルアン
モニオプロピル]ヒドロキシエチルセルロース ０.５
ジステアリン酸エチレングリコール ２.０
防腐剤 ０.１
香料組成物４ ０.１
精製水 ７５.３
トータル １００.０
Example 6
The shampoo 1 of this invention was obtained according to the following prescription.
Product name Compounding amount (parts by weight)
Polyoxyethylene (2) lauryl ether
Sodium sulfate 9.0
Sodium lauryl sulfate 4.0
Palm oil fatty acid amidopropyl betaine 3.0
Highly polymerized methylpolysiloxane 2.0
Methyl polysiloxane 1.0
Palm oil fatty acid monoethanolamide 1.0
Propylene glycol 2.0
O- [2-hydroxy-3-trimethylan chloride
Moniopropyl] hydroxyethyl cellulose 0.5
Ethylene glycol distearate 2.0
Preservative 0.1
Fragrance composition 4 0.1
Purified water 75.3
Total 100.0
〔比較例４〕
実施例６の香料組成物４の代わりに香料組成物５を配合してシャンプー２を得た。
[Comparative Example 4]
A shampoo 2 was obtained by blending the fragrance composition 5 instead of the fragrance composition 4 of Example 6.
〔試験例１〕
果汁飲料１、果汁飲料３の２種のジュースについて１０名の専門パネラーにより香気香味を比較評価した。
その結果、専門パネラーの全員が本発明品の果汁飲料１の方が果汁感が強調され、より天然感が強く感じられると評価した。
[Test Example 1]
About two kinds of juices of the fruit juice drink 1 and the fruit juice drink 3, the aroma flavor was comparatively evaluated by 10 expert panelists.
As a result, all the expert panelists evaluated that the juice juice 1 of the present invention emphasizes the fruit juice feeling and feels more natural.
〔試験例２〕
シャンプー１、シャンプー２の２種のシャンプーについて６名の専門パネラーによりビン香及び湯立ち時の香りの評価を行った。
その結果、ビン香、湯立ち時共に専門パネラー全員が本発明品シャンプー１の方が、さわやかな柑橘の天然感が強く感じられると評価した。
[Test Example 2]
Two types of shampoos, Shampoo 1 and Shampoo 2, were evaluated by bottled scents and scents at the time of standing in a hot water bath by six specialist panelists.
As a result, all the expert panelists evaluated that the shampoo 1 of the present invention felt a refreshing natural feeling of citrus, both at the time of incense and hot water.
本発明のグリーン様、アルデヒド様、メタリック様、みずみずしい果汁感を想起させる等の香気香味特性を有するシス−４，５−エポキシ−２Ｅ−デセナールを含有する香料組成物は菓子類、ジュースのような飲食物あるいは香粧品に使用すると、果汁感が強調されたよりナチュラル感が感じられる。 The fragrance composition containing cis-4,5-epoxy-2E-decenal having aroma and flavor characteristics such as green-like, aldehyde-like, metallic-like, and refreshing fruit juice according to the present invention is used for confectionery and juice. When used in foods and drinks or cosmetics, a natural feeling is felt more than the fruit juice feeling is emphasized.
Claims (3)
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| JP2003319168A JP4393824B2 (en) | 2003-09-11 | 2003-09-11 | Fragrance composition |
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|---|---|---|---|
| JP2003319168A JP4393824B2 (en) | 2003-09-11 | 2003-09-11 | Fragrance composition |
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| JP4393824B2 true JP4393824B2 (en) | 2010-01-06 |
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| JP2012075354A (en) * | 2010-09-30 | 2012-04-19 | Ogawa & Co Ltd | Flavor improving agent of soy milk or food and drink containing soy milk |
| JP6247443B2 (en) * | 2012-08-10 | 2017-12-13 | 小川香料株式会社 | Flavor improver for miso or miso-containing foods and drinks |
| JP6860487B2 (en) * | 2015-08-26 | 2021-04-14 | 小川香料株式会社 | Matcha flavor improver |
| CN106442778B (en) * | 2016-09-14 | 2019-01-29 | 广西大学 | A method of Guangxi Rong County shatian pomelo is identified using chromatography |
| JP6931289B2 (en) * | 2017-02-17 | 2021-09-01 | 小川香料株式会社 | Sweetness enhancer and sweetness enhancer flavor composition |
| WO2018155720A1 (en) | 2017-02-27 | 2018-08-30 | 高砂香料工業株式会社 | Novel spirosesquiterpene compound, flavoring composition and food/drink containing said compound, and method for producing said food/drink |
| JP6742294B2 (en) * | 2017-12-27 | 2020-08-19 | 株式会社 伊藤園 | Method for enhancing the juice feeling of a juice-containing beverage |
| SG11202010884TA (en) | 2018-05-11 | 2020-12-30 | Takasago Perfumery Co Ltd | Dienal compound and flavor composition |
| JP6724268B1 (en) * | 2018-10-10 | 2020-07-15 | 高砂香料工業株式会社 | Fragrance composition |
| JP7133813B2 (en) * | 2019-09-30 | 2022-09-09 | トモヱ乳業株式会社 | Flavor deterioration corrector |
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2003
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