JP4088250B2 - 化粧品香料（ｆｒａｇｒａｎｃｅ）および食品香料（ｆｌａｖｏｕｒ）組成物 - Google Patents
化粧品香料（ｆｒａｇｒａｎｃｅ）および食品香料（ｆｌａｖｏｕｒ）組成物 Download PDFInfo
- Publication number
- JP4088250B2 JP4088250B2 JP2003508324A JP2003508324A JP4088250B2 JP 4088250 B2 JP4088250 B2 JP 4088250B2 JP 2003508324 A JP2003508324 A JP 2003508324A JP 2003508324 A JP2003508324 A JP 2003508324A JP 4088250 B2 JP4088250 B2 JP 4088250B2
- Authority
- JP
- Japan
- Prior art keywords
- hydrogen
- formula
- methoxy
- carbon atoms
- benzene
- 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.)
- Expired - Lifetime
Links
- 239000003205 fragrance Substances 0.000 title claims description 21
- 239000000203 mixture Substances 0.000 title claims description 21
- 235000013305 food Nutrition 0.000 title claims description 17
- 239000002537 cosmetic Substances 0.000 title claims description 14
- 239000000796 flavoring agent Substances 0.000 title description 3
- 235000019634 flavors Nutrition 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 34
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- SHLSJFDJYSSUIP-UHFFFAOYSA-N 1-(cyclopropylmethyl)-4-methoxybenzene Chemical compound C1=CC(OC)=CC=C1CC1CC1 SHLSJFDJYSSUIP-UHFFFAOYSA-N 0.000 claims description 7
- 239000002304 perfume Substances 0.000 claims description 6
- LTUOAKZAEVRZQA-UHFFFAOYSA-N 1-(cyclobutylmethyl)-4-methoxybenzene Chemical compound C1=CC(OC)=CC=C1CC1CCC1 LTUOAKZAEVRZQA-UHFFFAOYSA-N 0.000 claims description 4
- SEZUWRUZEFZESF-UHFFFAOYSA-N 4-(cyclopropylmethyl)-1,2-dimethoxybenzene Chemical compound C1=C(OC)C(OC)=CC=C1CC1CC1 SEZUWRUZEFZESF-UHFFFAOYSA-N 0.000 claims description 4
- BAZICCZPOUAYSK-UHFFFAOYSA-N 4-(cyclopropylmethyl)-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC(CC2CC2)=C1 BAZICCZPOUAYSK-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- FISHRKITHXAYSJ-UHFFFAOYSA-N 1-(cyclopentylmethyl)-4-methoxybenzene Chemical compound C1=CC(OC)=CC=C1CC1CCCC1 FISHRKITHXAYSJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- DJBJAVLWJMSSRE-UHFFFAOYSA-N 2-methoxy-4-(2-methylcyclopropyl)phenol Chemical compound C1=C(O)C(OC)=CC(C2C(C2)C)=C1 DJBJAVLWJMSSRE-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 150000001924 cycloalkanes Chemical class 0.000 claims 1
- 235000019645 odor Nutrition 0.000 description 30
- 235000007265 Myrrhis odorata Nutrition 0.000 description 12
- 240000004760 Pimpinella anisum Species 0.000 description 12
- 235000012550 Pimpinella anisum Nutrition 0.000 description 12
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 12
- 235000013599 spices Nutrition 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- ZFMSMUAANRJZFM-UHFFFAOYSA-N Estragole Chemical compound COC1=CC=C(CC=C)C=C1 ZFMSMUAANRJZFM-UHFFFAOYSA-N 0.000 description 8
- 230000009286 beneficial effect Effects 0.000 description 8
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 8
- RUVINXPYWBROJD-ONEGZZNKSA-N trans-anethole Chemical compound COC1=CC=C(\C=C\C)C=C1 RUVINXPYWBROJD-ONEGZZNKSA-N 0.000 description 7
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 6
- 239000005770 Eugenol Substances 0.000 description 6
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 6
- 229960002217 eugenol Drugs 0.000 description 6
- RUVINXPYWBROJD-UHFFFAOYSA-N para-methoxyphenyl Natural products COC1=CC=C(C=CC)C=C1 RUVINXPYWBROJD-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229940011037 anethole Drugs 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 244000304337 Cuminum cyminum Species 0.000 description 2
- 235000007129 Cuminum cyminum Nutrition 0.000 description 2
- PXIKRTCSSLJURC-UHFFFAOYSA-N Dihydroeugenol Chemical compound CCCC1=CC=C(O)C(OC)=C1 PXIKRTCSSLJURC-UHFFFAOYSA-N 0.000 description 2
- 239000004278 EU approved seasoning Substances 0.000 description 2
- ZYEMGPIYFIJGTP-UHFFFAOYSA-N O-methyleugenol Chemical compound COC1=CC=C(CC=C)C=C1OC ZYEMGPIYFIJGTP-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 235000011194 food seasoning agent Nutrition 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 1
- KBHWKXNXTURZCD-UHFFFAOYSA-N 1-Methoxy-4-propylbenzene Chemical compound CCCC1=CC=C(OC)C=C1 KBHWKXNXTURZCD-UHFFFAOYSA-N 0.000 description 1
- FLNSLKJOWVMPEE-UHFFFAOYSA-N 2-methoxy-4-propylcyclohexan-1-ol Chemical compound CCCC1CCC(O)C(OC)C1 FLNSLKJOWVMPEE-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- DHAFEXLUSJAKOG-UHFFFAOYSA-N 5-(2-methylcyclopropyl)-1,3-benzodioxole Chemical compound CC1CC1C1=CC=C(OCO2)C2=C1 DHAFEXLUSJAKOG-UHFFFAOYSA-N 0.000 description 1
- GGBXNQPSKPVLPB-UHFFFAOYSA-N 5-(cyclopropylmethyl)-1,3-benzodioxole Chemical compound C=1C=C2OCOC2=CC=1CC1CC1 GGBXNQPSKPVLPB-UHFFFAOYSA-N 0.000 description 1
- 240000001851 Artemisia dracunculus Species 0.000 description 1
- 235000002566 Capsicum Nutrition 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 244000018436 Coriandrum sativum Species 0.000 description 1
- 235000002787 Coriandrum sativum Nutrition 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- BJIOGJUNALELMI-ONEGZZNKSA-N Isoeugenol Natural products COC1=CC(\C=C\C)=CC=C1O BJIOGJUNALELMI-ONEGZZNKSA-N 0.000 description 1
- 235000006679 Mentha X verticillata Nutrition 0.000 description 1
- 235000002899 Mentha suaveolens Nutrition 0.000 description 1
- 235000001636 Mentha x rotundifolia Nutrition 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000006002 Pepper Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 235000016761 Piper aduncum Nutrition 0.000 description 1
- 235000017804 Piper guineense Nutrition 0.000 description 1
- 244000203593 Piper nigrum Species 0.000 description 1
- 235000008184 Piper nigrum Nutrition 0.000 description 1
- 244000141353 Prunus domestica Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 235000016639 Syzygium aromaticum Nutrition 0.000 description 1
- 244000223014 Syzygium aromaticum Species 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- QROGIFZRVHSFLM-QHHAFSJGSA-N [(e)-prop-1-enyl]benzene Chemical compound C\C=C\C1=CC=CC=C1 QROGIFZRVHSFLM-QHHAFSJGSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- BJIOGJUNALELMI-ARJAWSKDSA-N cis-isoeugenol Chemical compound COC1=CC(\C=C/C)=CC=C1O BJIOGJUNALELMI-ARJAWSKDSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 description 1
- ZFYOOJLCJQTVHL-UHFFFAOYSA-N cyclobutyl-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCC1 ZFYOOJLCJQTVHL-UHFFFAOYSA-N 0.000 description 1
- WEIXVVOVSXWQLQ-UHFFFAOYSA-N cyclopentyl(1,3-dioxol-4-yl)methanone Chemical compound O1COC=C1C(=O)C1CCCC1 WEIXVVOVSXWQLQ-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000002979 fabric softener Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000015143 herbs and spices Nutrition 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 229940116837 methyleugenol Drugs 0.000 description 1
- PRHTXAOWJQTLBO-UHFFFAOYSA-N methyleugenol Natural products COC1=CC=C(C(C)=C)C=C1OC PRHTXAOWJQTLBO-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- QROGIFZRVHSFLM-UHFFFAOYSA-N prop-1-enylbenzene Chemical class CC=CC1=CC=CC=C1 QROGIFZRVHSFLM-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 235000021572 root beer Nutrition 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 235000021259 spicy food Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BJIOGJUNALELMI-UHFFFAOYSA-N trans-isoeugenol Natural products COC1=CC(C=CC)=CC=C1O BJIOGJUNALELMI-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Seasonings (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01115991A EP1269982A1 (en) | 2001-06-30 | 2001-06-30 | Fragrance and flavour compositions |
| PCT/CH2002/000352 WO2003002084A2 (en) | 2001-06-30 | 2002-06-28 | Fragrance and flavour compositions |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005505511A JP2005505511A (ja) | 2005-02-24 |
| JP2005505511A5 JP2005505511A5 (enExample) | 2006-01-05 |
| JP4088250B2 true JP4088250B2 (ja) | 2008-05-21 |
Family
ID=8177911
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003508324A Expired - Lifetime JP4088250B2 (ja) | 2001-06-30 | 2002-06-28 | 化粧品香料（ｆｒａｇｒａｎｃｅ）および食品香料（ｆｌａｖｏｕｒ）組成物 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7704942B2 (enExample) |
| EP (2) | EP1269982A1 (enExample) |
| JP (1) | JP4088250B2 (enExample) |
| CN (1) | CN1245934C (enExample) |
| AT (1) | ATE471142T1 (enExample) |
| AU (1) | AU2002315612A1 (enExample) |
| BR (1) | BR0210749B1 (enExample) |
| DE (1) | DE60236729D1 (enExample) |
| ES (1) | ES2346741T3 (enExample) |
| MX (1) | MXPA03010821A (enExample) |
| WO (1) | WO2003002084A2 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1269982A1 (en) | 2001-06-30 | 2003-01-02 | Givaudan SA | Fragrance and flavour compositions |
| MX2011004320A (es) * | 2008-11-07 | 2011-05-30 | Firmenich & Cie | Ingredientes aromatizantes de tipo floral y/o anis. |
| IN2014CN00736A (enExample) * | 2011-08-29 | 2015-04-03 | Firmenich & Cie | |
| GB201516396D0 (en) | 2015-09-16 | 2015-10-28 | Givaudan Sa | Improvements in or relating to organic compounds |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2507778C3 (de) | 1975-02-22 | 1980-06-26 | Haarmann & Reimer Gmbh, 3450 Holzminden | Verwendung von Dichlorcyclopropanderivaten als Riechstoffe |
| US4190591A (en) | 1977-01-21 | 1980-02-26 | Givaudan Corporation | Odorant and flavorant |
| CH633550A5 (en) * | 1977-01-21 | 1982-12-15 | Givaudan & Cie Sa | Process for the preparation of a new aroma substance and/or flavouring |
| US4306096A (en) | 1980-09-30 | 1981-12-15 | International Flavors & Fragrances Inc. | Cyclohexyl phenethylether |
| DE3128987A1 (de) | 1981-07-22 | 1983-02-10 | Dragoco Gerberding & Co Gmbh, 3450 Holzminden | Verwendung von 1-ethoxi-4-ethyl-benzol als riech- und aromastoff |
| JPS5821634A (ja) * | 1981-07-31 | 1983-02-08 | Ogawa Koryo Kk | シクロプロピルベンゼン誘導体およびそれを含有する香料組成物 |
| US4657700A (en) | 1983-10-07 | 1987-04-14 | Givaudan Corporation | Fragrance compositions containing benzyl ethers |
| JPH0694417B2 (ja) | 1984-08-03 | 1994-11-24 | 株式会社資生堂 | 現代ローズ香料組成物及びその製造方法 |
| NL8403220A (nl) | 1984-10-23 | 1986-05-16 | Naarden International Nv | Parfumcomposities en geparfumeerde produkten, die een of meer o-alkoxyfenolen als grondstof bevatten. |
| US4696766A (en) * | 1986-03-19 | 1987-09-29 | Givaudan Corporation | (2R*,3S*)-(E)-3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pent-4-en-2-ol |
| ES2074448T3 (es) | 1988-02-25 | 1995-09-16 | Firmenich & Cie | Utilizacion de 2-metoxi-4-propil-1-ciclohexanol como agente perfumante. |
| DE4115184A1 (de) * | 1991-05-09 | 1992-11-12 | Bayer Ag | Benzothiophen-2-carboxamid-s,s-dioxide |
| US5169669A (en) * | 1991-09-25 | 1992-12-08 | The Procter & Gamble Company | Cooking oils |
| US5222141A (en) | 1992-03-25 | 1993-06-22 | Motorola, Inc. | Apparatus and method for encoding data |
| JPH06287591A (ja) | 1993-04-06 | 1994-10-11 | Lion Corp | 香料組成物 |
| JP3676394B2 (ja) | 1994-04-25 | 2005-07-27 | 曽田香料株式会社 | 香料組成物 |
| US5707961A (en) * | 1995-05-16 | 1998-01-13 | Givaudan-Roure (International) Sa | Odorant compounds and compositions |
| JP3802068B2 (ja) * | 1995-11-01 | 2006-07-26 | ジボーダン ソシエテ アノニム | ニトリル |
| WO1997034988A1 (en) * | 1996-03-19 | 1997-09-25 | The Procter & Gamble Company | Glass cleaning compositions containing blooming perfume |
| JP2894445B2 (ja) * | 1997-02-12 | 1999-05-24 | 日本たばこ産業株式会社 | Ｃｅｔｐ活性阻害剤として有効な化合物 |
| ES2174390T3 (es) | 1998-07-27 | 2002-11-01 | Pfw Aroma Chem | Eteres cicloalquilicos y composiciones perfumantes que los contienen. |
| JP4643775B2 (ja) * | 1999-01-13 | 2011-03-02 | 日本食品化工株式会社 | 香気成分生成阻害剤 |
| AU2001227375A1 (en) * | 2000-02-08 | 2001-08-20 | Herbert T. Nagasawa | N-terminal d(-)-penicillamine peptides as aldehyde sequestration agents |
| EP1269982A1 (en) | 2001-06-30 | 2003-01-02 | Givaudan SA | Fragrance and flavour compositions |
| US20050049146A1 (en) * | 2001-11-05 | 2005-03-03 | Chiarello John F. | Use of substituted dibenzothiepine derivatives as insecticidal, acaricidal and nematicidal agents |
-
2001
- 2001-06-30 EP EP01115991A patent/EP1269982A1/en not_active Withdrawn
-
2002
- 2002-06-28 AT AT02740179T patent/ATE471142T1/de not_active IP Right Cessation
- 2002-06-28 DE DE60236729T patent/DE60236729D1/de not_active Expired - Lifetime
- 2002-06-28 US US10/481,733 patent/US7704942B2/en not_active Expired - Lifetime
- 2002-06-28 BR BRPI0210749-0B1A patent/BR0210749B1/pt active IP Right Grant
- 2002-06-28 MX MXPA03010821A patent/MXPA03010821A/es active IP Right Grant
- 2002-06-28 WO PCT/CH2002/000352 patent/WO2003002084A2/en not_active Ceased
- 2002-06-28 ES ES02740179T patent/ES2346741T3/es not_active Expired - Lifetime
- 2002-06-28 AU AU2002315612A patent/AU2002315612A1/en not_active Abandoned
- 2002-06-28 JP JP2003508324A patent/JP4088250B2/ja not_active Expired - Lifetime
- 2002-06-28 EP EP02740179A patent/EP1401388B1/en not_active Expired - Lifetime
- 2002-06-28 CN CNB028117107A patent/CN1245934C/zh not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| WO2003002084A3 (en) | 2003-08-28 |
| EP1269982A1 (en) | 2003-01-02 |
| US20050042255A1 (en) | 2005-02-24 |
| EP1401388A2 (en) | 2004-03-31 |
| DE60236729D1 (de) | 2010-07-29 |
| ATE471142T1 (de) | 2010-07-15 |
| CN1514718A (zh) | 2004-07-21 |
| MXPA03010821A (es) | 2004-02-17 |
| US7704942B2 (en) | 2010-04-27 |
| CN1245934C (zh) | 2006-03-22 |
| JP2005505511A (ja) | 2005-02-24 |
| EP1401388B1 (en) | 2010-06-16 |
| AU2002315612A1 (en) | 2003-03-03 |
| BR0210749A (pt) | 2004-07-20 |
| ES2346741T3 (es) | 2010-10-20 |
| WO2003002084A2 (en) | 2003-01-09 |
| BR0210749B1 (pt) | 2013-12-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2798476B2 (ja) | 芳香族アルデヒドおよびその誘導体、香料成分、香料組成物、香料添加製品、新規化合物の製造法、窒素複素環式化合物、ならびに殺菌作用および除草作用を有する薬剤 | |
| WO1995016660A1 (en) | Cis-3-hexenal cis-3-hexenyl acetal compound, process for producing the same, and flavor/taste imparting agent, flavor/taste retaining agent and perfume composition each containing the same | |
| JP4088250B2 (ja) | 化粧品香料（ｆｒａｇｒａｎｃｅ）および食品香料（ｆｌａｖｏｕｒ）組成物 | |
| JP4012461B2 (ja) | 不飽和エステル化合物、その使用及びこれを含有する付香組成物及び付香された製品 | |
| CA2545617A1 (en) | Novel oxy-nitriles | |
| EP0016650A2 (en) | 2-Cyclopentyl-cyclopentanone, fragrance or flavouring compositions containing it and their use | |
| US5874398A (en) | Ethylvanillin isobutyrate | |
| US3862340A (en) | Flavoring with 5-phenyl pentenals | |
| US4173584A (en) | Novel cyclopentanone derivatives as flavor- and odor-modifying ingredients | |
| JPS60224650A (ja) | ケトン異性体混合物、その製造方法およびその組成物 | |
| US4031140A (en) | 4- AND 5-Phenyl pentenal acetals | |
| US4179448A (en) | Spirane derivatives useful as perfuming and flavor-modifying ingredients | |
| KR101516837B1 (ko) | 6,8,10-운데카트리엔-3 또는 4-올 및 향료 조성물 | |
| JPH0261520B2 (enExample) | ||
| US4261867A (en) | Using 1-ethynyl-2,2,6-trimethyl-cyclohexanol to enhance woody fragrance of perfume compositions | |
| CN103747774A (zh) | 6-环亚戊基己烷衍生物的感觉用途 | |
| CN103562167B (zh) | 用于香料组合物和香味产品的萜烯醇 | |
| JP2013519646A (ja) | ７−（アルカ−１’−エニル）−２Ｈ−ベンゾ［ｂ］［１，４］ジオキセピン−３（４Ｈ）−オン類およびフレグランス利用品におけるそれらの使用 | |
| US4036886A (en) | Processes for producing 4- and 5-phenyl pentenals | |
| BR0103014B1 (pt) | Composição de fragrância compreendendo uma mistura de nitrilas, seu uso, bem como produtos de consumo e seu método de preparação | |
| US4206089A (en) | 5-Alkylbicyclo[4.3.0]non-1-en-3-one and 5-alkylbicyclo[4.3.0]nonane-3-one perfume compositions | |
| JP2001055599A (ja) | 香り特性を付与、改善、強化または改変する方法、香料組成物、付香製品、および新規脂肪族エステル | |
| US4483786A (en) | Nitrile musk composition | |
| US4252693A (en) | Perfume compositions containing spirane derivatives | |
| EP0231896B1 (en) | Alpha, beta-unsaturated ketones and their use as aroma chemicals |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20050627 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20050627 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20061122 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20061212 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20070312 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20080219 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20080222 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20110228 Year of fee payment: 3 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 4088250 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120229 Year of fee payment: 4 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130228 Year of fee payment: 5 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20140228 Year of fee payment: 6 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| EXPY | Cancellation because of completion of term |