JP2013531098A - 有機化合物 - Google Patents
有機化合物 Download PDFInfo
- Publication number
- JP2013531098A JP2013531098A JP2013515885A JP2013515885A JP2013531098A JP 2013531098 A JP2013531098 A JP 2013531098A JP 2013515885 A JP2013515885 A JP 2013515885A JP 2013515885 A JP2013515885 A JP 2013515885A JP 2013531098 A JP2013531098 A JP 2013531098A
- Authority
- JP
- Japan
- Prior art keywords
- flavor
- tetrahydroquinoline
- cyclopenta
- dihydro
- pyridine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
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- 150000001875 compounds Chemical class 0.000 claims abstract description 40
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- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
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- 239000000203 mixture Substances 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 8
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- 125000003118 aryl group Chemical group 0.000 claims description 4
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
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- 150000002825 nitriles Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 1
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- NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000008601 oleoresin Substances 0.000 description 1
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- 239000012074 organic phase Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 235000021017 pears Nutrition 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
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- 150000003216 pyrazines Chemical class 0.000 description 1
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
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- 235000021147 sweet food Nutrition 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 150000003530 tetrahydroquinolines Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000010678 thyme oil Substances 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- 239000008371 vanilla flavor Substances 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 235000015041 whisky Nutrition 0.000 description 1
- 235000013618 yogurt Nutrition 0.000 description 1
Classifications
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- 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/205—Heterocyclic compounds
- A23L27/2054—Heterocyclic compounds having nitrogen as the only hetero atom
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q15/00—Anti-perspirants or body deodorants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
-
- 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
- C11B9/0069—Heterocyclic compounds
- C11B9/0092—Heterocyclic compounds containing only N as heteroatom
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Food Science & Technology (AREA)
- Nutrition Science (AREA)
- Polymers & Plastics (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Seasonings (AREA)
Abstract
式中
n=0、1、2、3および
R=C2〜C6の直鎖状および分岐状アルキル、アルケニルおよびシクロアルキル置換基
で表される化合物は、ハーバルグリーンの面を有する興味深いフレーバーまたはフレグランス成分である。
Description
5,6,7,8−テトラヒドロキノリン誘導体は、文献に開示されている。ある5,6,7,8−テトラヒドロキノリン誘導体は、Monatshefte fuer Chemie 1984, 115, 1219; J. Chem Soc. Perkin Tr. 1, 1980, 1933に開示されているが、それらの香りの説明は、描写されていない。
n=0、1、2、3および
R=C2〜C6の直鎖状および分岐状アルキル、アルケニルおよびシクロアルキル置換基
で表される化合物と一致するある8−置換5,6,7,8−テトラヒドロキノリン化合物が、望ましいハーバルグリーンの香りを示すことから、それらがフレグランスまたはフレーバー利用品における使用に好適であり、フレッシュ、緑のトマトの葉、朝鮮人参およびプチグレンの香りの方向の非常に望ましい香りのプロファイルを提供することから、これらの材料が香水およびフレーバー産業における利用に著しく好適であることを見出した。
上に論じたように、式(I)に属するある化合物は、既知であるが、それらの香りは、記載されたことがない。
n=0、1、2、3および
R=C2〜C6の直鎖状および分岐状アルキル、アルケニルおよびシクロアルキル置換基
で表される化合物を提供するが、化合物
8−sec−ブチル−5,6,7,8−テトラヒドロキノリン
8−(ペンタン−2−イル)−5,6,7,8−テトラヒドロキノリン
8−(ペンタン−3−イル)−5,6,7,8−テトラヒドロキノリン
7−sec−ブチル−6,7−ジヒドロ−5H−シクロペンタ[b]ピリジン
7−(ペンタン−2−イル)−6,7−ジヒドロ−5H−シクロペンタ[b]ピリジン
7−(ペンタン−3−イル)−6,7−ジヒドロ−5H−シクロペンタ[b]ピリジン
7−(3−メチルブタ−2−エニル)−6,7−ジヒドロ−5H−シクロペンタ[b]ピリジン
である。
それらの望ましい香りのプロファイルのために、式(I)で表される化合物は、あらゆる種類の香水利用品においてフレグランス成分としての使用に好適である。同様に、それらの香りはまた、食品、飲料およびオーラルケア製品にアロマを添加し得ることから、フレーバー剤の成分として好適である。
前記フレグランスまたはフレーバー組成物はまた、式(I)で表される化合物のための担体材料、香水またはフレーバーベース、ならびにフレグランスおよびフレーバー配合物に有用な他の助剤を含んでもよい。
ここで、以下に本発明を例示する一連の例が続く。
8−sec−ブチル−5,6,7,8−テトラヒドロキノリン(GR-50-0572)
香り:グリーン、ハーブ調、アメリカ人参、ショウガ、トマトの葉、エンドウ。
4:6の比率の2種類の異性体(isomer)。
8−(ブタ−3−エン−2−イル)−5,6,7,8−テトラヒドロキノリン
8:2の比率の2種類の異性体。
8−(ブタ−2−エニル)−5,6,7,8−テトラヒドロキノリン
9:1の比率の(E,Z)異性体の混合物。
8−(2,3−ジメチルブタ−2−エニル)−5,6,7,8−テトラヒドロキノリン
8−イソブチル−5,6,7,8−テトラヒドロキノリン
8−イソプロピル−5,6,7,8−テトラヒドロキノリン
8−(ペンタン−2−イル)−5,6,7,8−テトラヒドロキノリン
(1:1)の比率の2種類の異性体。
8−(ペンタン−3−イル)−5,6,7,8−テトラヒドロキノリン
8−シクロヘキシル−5,6,7,8−テトラヒドロキノリン
8−(2−メタリル)−5,6,7,8−テトラヒドロキノリン
8−ヘキシル−5,6,7,8−テトラヒドロキノリン
7−sec−ブチル−6,7−ジヒドロ−5H−シクロペンタ[b]ピリジン
(1:1)の比率の2種類の異性体。
7−(ペンタン−2−イル)−6,7−ジヒドロ−5H−シクロペンタ[b]ピリジン
(1:1)の比率の2種類の異性体の混合物。
7−(ペンタン−3−イル)−6,7−ジヒドロ−5H−シクロペンタ[b]ピリジン
7−(2−メタリル)−6,7−ジヒドロ−5H−シクロペンタ[b]ピリジン
7−イソブチル−6,7−ジヒドロ−5H−シクロペンタ[b]ピリジン
7−(3−メチルブタ−2−エニル)−6,7−ジヒドロ−5H−シクロペンタ[b]ピリジン
7−(ブタ−3−エン−2−イル)−6,7−ジヒドロ−5H−シクロペンタ[b]ピリジン
2:8の比率の2種類の異性体。
7−ペンチル−6,7−ジヒドロ−5H−シクロペンタ[b]ピリジン
7−シクロヘキシル−6,7−ジヒドロ−5H−シクロペンタ[b]ピリジン
8−sec−ブチル−5,6,7,8−テトラヒドロキノリンがシトラスの特徴を増大させる有機的でスパイシーな、ショウガ香水利用品は、フレッシュさを与え、自然なグリーンの面を創造する。
Claims (6)
- 式(I)
n=0、1、2、3および
R=C2〜C6の直鎖状および分岐状アルキル、アルケニルおよびシクロアルキル置換基
で表される化合物の、フレーバーまたはフレグランス成分としての使用。 - 式(I)で表される化合物が、
8−sec−ブチル−5,6,7,8−テトラヒドロキノリン、
8−(ペンタン−2−イル)−5,6,7,8−テトラヒドロキノリン、
8−(ペンタン−3−イル)−5,6,7,8−テトラヒドロキノリン、
7−sec−ブチル−6,7−ジヒドロ−5H−シクロペンタ[b]ピリジン、
7−(ペンタン−2−イル)−6,7−ジヒドロ−5H−シクロペンタ[b]ピリジン、
7−(ペンタン−3−イル)−6,7−ジヒドロ−5H−シクロペンタ[b]ピリジン、
7−(3−メチルブタ−2−エニル)−6,7−ジヒドロ−5H−シクロペンタ[b]ピリジン
からなる群から選択される、請求項1に記載の使用。 - 式(I)で表される化合物を含む、フレグランスまたはフレーバー組成物あるいはフレーバー付または芳香品物。
- 着香組成物のまたは芳香品物の、あるいはフレーバー組成物またはフレーバー付品物の快楽特性を与える、増大させる、改善するまたは改変する方法であって、前記組成物または品物に式(I)で表される化合物を添加する、前記方法。
- 式(I)で表される化合物であって、
- 8−sec−ブチル−5,6,7,8−テトラヒドロキノリン、
8−(ペンタン−2−イル)−5,6,7,8−テトラヒドロキノリン、
8−(ペンタン−3−イル)−5,6,7,8−テトラヒドロキノリン、
7−sec−ブチル−6,7−ジヒドロ−5H−シクロペンタ[b]ピリジン、
7−(ペンタン−2−イル)−6,7−ジヒドロ−5H−シクロペンタ[b]ピリジン、
7−(ペンタン−3−イル)−6,7−ジヒドロ−5H−シクロペンタ[b]ピリジン、
7−(3−メチルブタ−2−エニル)−6,7−ジヒドロ−5H−シクロペンタ[b]ピリジン
からなる群から選択される、請求項5に記載の化合物。
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DE102015217867A1 (de) * | 2015-09-17 | 2017-03-23 | Henkel Ag & Co. Kgaa | Parfümzusammensetzung mit Geruchsmodulatorverbindungen zur Steigerung der Duftintensität |
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JP2017533745A (ja) * | 2014-10-14 | 2017-11-16 | ジボダン エス エー | 悪臭低減組成物 |
KR102342562B1 (ko) * | 2014-10-14 | 2021-12-23 | 지보당 에스아 | 악취-감소 조성물 |
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