JP4801070B2 - 香料成分としての不飽和エーテル - Google Patents
香料成分としての不飽和エーテル Download PDFInfo
- Publication number
- JP4801070B2 JP4801070B2 JP2007529018A JP2007529018A JP4801070B2 JP 4801070 B2 JP4801070 B2 JP 4801070B2 JP 2007529018 A JP2007529018 A JP 2007529018A JP 2007529018 A JP2007529018 A JP 2007529018A JP 4801070 B2 JP4801070 B2 JP 4801070B2
- Authority
- JP
- Japan
- Prior art keywords
- perfume
- compound
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- mixture
- 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 - Fee Related
Links
- 239000004615 ingredient Substances 0.000 title claims abstract description 18
- 239000002304 perfume Substances 0.000 title claims description 39
- 150000002170 ethers Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 45
- 239000000203 mixture Substances 0.000 claims abstract description 35
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 239000003205 fragrance Substances 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 239000002671 adjuvant Substances 0.000 claims description 5
- 239000003599 detergent Substances 0.000 claims description 5
- 239000002537 cosmetic Substances 0.000 claims description 4
- 239000004744 fabric Substances 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 239000002386 air freshener Substances 0.000 claims description 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 3
- 239000012437 perfumed product Substances 0.000 claims description 3
- 241000195940 Bryophyta Species 0.000 claims description 2
- 230000001166 anti-perspirative effect Effects 0.000 claims description 2
- 239000003213 antiperspirant Substances 0.000 claims description 2
- 239000007844 bleaching agent Substances 0.000 claims description 2
- 210000001072 colon Anatomy 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 239000002781 deodorant agent Substances 0.000 claims description 2
- 239000002979 fabric softener Substances 0.000 claims description 2
- 238000010409 ironing Methods 0.000 claims description 2
- 239000006210 lotion Substances 0.000 claims description 2
- 235000019341 magnesium sulphate Nutrition 0.000 claims description 2
- 235000011929 mousse Nutrition 0.000 claims description 2
- 235000019198 oils Nutrition 0.000 claims description 2
- 239000000123 paper Substances 0.000 claims description 2
- 239000002453 shampoo Substances 0.000 claims description 2
- 239000000344 soap Substances 0.000 claims description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims 1
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 abstract 1
- 244000172533 Viola sororia Species 0.000 abstract 1
- 239000000047 product Substances 0.000 description 22
- 239000002243 precursor Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000001345 alkine derivatives Chemical class 0.000 description 4
- 125000005336 allyloxy group Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 238000005538 encapsulation Methods 0.000 description 3
- 239000000796 flavoring agent Substances 0.000 description 3
- 235000019634 flavors Nutrition 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 230000002730 additional effect Effects 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000005354 coacervation Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 2
- NTLJTUMJJWVCTL-UHFFFAOYSA-N methyl non-2-ynoate Chemical group CCCCCCC#CC(=O)OC NTLJTUMJJWVCTL-UHFFFAOYSA-N 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 230000001953 sensory effect Effects 0.000 description 2
- -1 terpene hydrocarbons Chemical class 0.000 description 2
- 235000007586 terpenes Nutrition 0.000 description 2
- FINOAUDUYKVGDS-UHFFFAOYSA-N (2-tert-butylcyclohexyl) acetate Chemical compound CC(=O)OC1CCCCC1C(C)(C)C FINOAUDUYKVGDS-UHFFFAOYSA-N 0.000 description 1
- NQQMOJGXMKJFPG-XBXARRHUSA-N (e)-7-pentoxyhept-2-en-5-yn-4-ol Chemical compound CCCCCOCC#CC(O)\C=C\C NQQMOJGXMKJFPG-XBXARRHUSA-N 0.000 description 1
- DAJPRYASLFUGOV-ZZXKWVIFSA-N (e)-7-propoxyhept-2-en-5-yn-4-ol Chemical compound CCCOCC#CC(O)\C=C\C DAJPRYASLFUGOV-ZZXKWVIFSA-N 0.000 description 1
- GAQOILKTBJWUQM-UHFFFAOYSA-N 3-prop-2-ynoxyprop-1-ene Chemical compound C=CCOCC#C GAQOILKTBJWUQM-UHFFFAOYSA-N 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- UEWCJKODSTYONH-UHFFFAOYSA-N 7-pentoxyhepta-1,3-dien-5-yne Chemical compound CCCCCOCC#CC=CC=C UEWCJKODSTYONH-UHFFFAOYSA-N 0.000 description 1
- DSZPIMRDLYFPBG-UHFFFAOYSA-N 7-propoxyhepta-1,3-dien-5-yne Chemical compound CCCOCC#CC=CC=C DSZPIMRDLYFPBG-UHFFFAOYSA-N 0.000 description 1
- OMPIYDSYGYKWSG-UHFFFAOYSA-N Citronensaeure-alpha-aethylester Natural products CCOC(=O)CC(O)(C(O)=O)CC(O)=O OMPIYDSYGYKWSG-UHFFFAOYSA-N 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229960002903 benzyl benzoate Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical class OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229940057975 ethyl citrate Drugs 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000000416 hydrocolloid Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- SDQFDHOLCGWZPU-UHFFFAOYSA-N lilial Chemical compound O=CC(C)CC1=CC=C(C(C)(C)C)C=C1 SDQFDHOLCGWZPU-UHFFFAOYSA-N 0.000 description 1
- 235000001510 limonene Nutrition 0.000 description 1
- 229940087305 limonene Drugs 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- 150000004043 trisaccharides Chemical class 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
-
- 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
- C11B9/0007—Aliphatic compounds
- C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
Description
我々の知る限りにおいては、本発明の化合物は新規である。もっとも近い公知の類似体は7−メトキシ−1,3−へプタジエン−5−インであり、この場合、これらは、化合物中間体として、 Tetrahedron Letters, 1979, 1, pg 7-10で報告されている。前記文献には、本発明の化合物の任意の香気特性については挙げられておらずまた示唆もない。
驚くべきことに、式(I)
i)香料成分として、前記に示された少なくとも1種の化合物、
ii)香料キャリアおよび香料ベースから成る群から選択された少なくとも1種の化合物、および
iii)場合によっては少なくとも1種の香料アジュバント、
を含有する、香料組成物である。
i)香料成分として、少なくとも1種の式(1)の化合物、および
ii)消費製品ベース、
を含有する賦香製品は、さらに本発明の対象である。
例1:式Iの化合物の合成
A)前駆体の製造:一般的方法
500mlの三首フラスコを、2MのEt2O(由来:Fluka)中100mmolの塩化イソプロピルマグネシウム溶液で装填した。その後に、100mmolの出発アルキンを30分に亘って、30℃前後の温度に維持しながら添加した。反応を、室温で1時間に亘っておこない、かつ100mmolのクロトンアルデヒド、この場合、100mlの乾燥Et2O中で希釈したもの、を20分に亘って添加した。さらに30分後に、反応混合物を、10mlの酢酸を含有する冷水(200ml)中に注ぎ入れた。有機相を、水で洗浄し、かつ溶剤を真空下で除去した。粗生成物を急速に減圧下で蒸留し(クーゲルロール蒸留)、好ましい前駆体を得た。
500mlの三首フラスコを、300mlのトルエンおよび0.5gのp−トルエンスルホン酸一水和物中の前駆体溶液50mmolで装填した。反応を、ディーンスターク装置を用いて還流で加熱し、形成された水を除去した。30分後に、反応を室温に冷却し、かつ3回に亘って水で洗浄した。溶剤を、真空下で除去し、かつ本発明の粗生成物を、バルブ−トウ−バルブ(bulb-to-bulb)蒸留によって精製した。
香料組成物の製造
「フルーティー−グリーン−ムスク」型の香料組成物を、以下の成分を混合することにより得た。
1)由来:Firmemch SA,Geneva, Switzerland
2)ペンタデゼノリド;由来:Firmemch SA,Geneva, Switzerland
3)3−(4−tert−ブチルフェニル)−2−メチルプロパナル;由来:Givaudan-Roure SA, Vernier, Switzerland
4)2−tert−ブチル−1−シクロヘキシルアセテート;由来:International Flavors & Fragrances, USA
Claims (7)
- Rが、C2〜C4アルキル基を示す、請求項1に記載の化合物。
- 立体配置(3E)または(3Z)の異性体の混合物の形であって、かつその際、立体配置(3E)の異性体が、混合物の質量に対して少なくとも60質量%を示す、請求項1に記載の化合物。
- i)少なくとも1種の請求項1に記載の本発明による化合物、
ii)香料キャリアおよび香料ベースから成る群から選択された少なくとも1種の成分;および
iii)場合によっては、少なくとも1種の香料アジュバント、
を含有する、組成物の形の香料成分。 - 請求項1に記載の式(I)の化合物または請求項4に記載の組成物の香料成分としての使用。
- i)少なくとも1種の請求項1に記載の式(I)の化合物、
および
ii)消費製品ベース、
を含有する、賦香製品。 - 非嗜好性消費製品ベースが、固体または液体洗剤、繊維柔軟剤、香水、コロンまたはアフターシェイブローション、化粧石鹸、シャワーまたはバスソルト、ムース、オイルまたはジェル、衛生製品、ヘアケア製品、シャンプー、ボディケア製品、デオドラントまたは制汗剤、エアフレッシュナー、化粧品、ファブリックリフレッシュナー、アイロン水、紙、布または漂白剤である、請求項6に記載の賦香製品。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IBPCT/IB2004/002778 | 2004-08-27 | ||
IB2004002778 | 2004-08-27 | ||
PCT/IB2005/002465 WO2006021857A2 (en) | 2004-08-27 | 2005-08-22 | Unsaturated ethers as perfuming ingredients |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2008510787A JP2008510787A (ja) | 2008-04-10 |
JP4801070B2 true JP4801070B2 (ja) | 2011-10-26 |
Family
ID=35699945
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2007529018A Expired - Fee Related JP4801070B2 (ja) | 2004-08-27 | 2005-08-22 | 香料成分としての不飽和エーテル |
Country Status (7)
Country | Link |
---|---|
US (1) | US7767639B2 (ja) |
EP (1) | EP1784374B1 (ja) |
JP (1) | JP4801070B2 (ja) |
CN (1) | CN1989094B (ja) |
AT (1) | ATE388131T1 (ja) |
DE (1) | DE602005005206T2 (ja) |
WO (1) | WO2006021857A2 (ja) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9115329B2 (en) | 2011-08-11 | 2015-08-25 | Firmenich Sa | Violet leaves odorants |
EP2928995B1 (en) | 2012-12-05 | 2016-08-24 | Firmenich SA | Odorants of the violet type |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3248430A (en) * | 1962-03-22 | 1966-04-26 | Hoffmann La Roche | Novel ethers and process for producing same |
US3786075A (en) * | 1970-04-06 | 1974-01-15 | Roure Bertrand Dupont Sa | Hydroxy ethers having odorant properties |
JPS5214711A (en) * | 1975-07-23 | 1977-02-03 | Basf Ag | Novel 122alkoxyy3*7*111 trimethyldodecatetraen |
JPH0860178A (ja) * | 1994-07-28 | 1996-03-05 | Firmenich Sa | 香料組成物及び香料添加製品ならびに匂いの性質の付与、改善、増強もしくは改質の方法 |
-
2005
- 2005-08-22 JP JP2007529018A patent/JP4801070B2/ja not_active Expired - Fee Related
- 2005-08-22 DE DE602005005206T patent/DE602005005206T2/de active Active
- 2005-08-22 CN CN2005800242781A patent/CN1989094B/zh not_active Expired - Fee Related
- 2005-08-22 AT AT05774460T patent/ATE388131T1/de not_active IP Right Cessation
- 2005-08-22 EP EP05774460A patent/EP1784374B1/en not_active Not-in-force
- 2005-08-22 WO PCT/IB2005/002465 patent/WO2006021857A2/en active IP Right Grant
-
2006
- 2006-12-14 US US11/611,076 patent/US7767639B2/en active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3248430A (en) * | 1962-03-22 | 1966-04-26 | Hoffmann La Roche | Novel ethers and process for producing same |
US3786075A (en) * | 1970-04-06 | 1974-01-15 | Roure Bertrand Dupont Sa | Hydroxy ethers having odorant properties |
JPS5214711A (en) * | 1975-07-23 | 1977-02-03 | Basf Ag | Novel 122alkoxyy3*7*111 trimethyldodecatetraen |
JPH0860178A (ja) * | 1994-07-28 | 1996-03-05 | Firmenich Sa | 香料組成物及び香料添加製品ならびに匂いの性質の付与、改善、増強もしくは改質の方法 |
Also Published As
Publication number | Publication date |
---|---|
EP1784374B1 (en) | 2008-03-05 |
CN1989094B (zh) | 2010-06-09 |
WO2006021857A3 (en) | 2006-05-04 |
DE602005005206D1 (de) | 2008-04-17 |
JP2008510787A (ja) | 2008-04-10 |
US20070087956A1 (en) | 2007-04-19 |
US7767639B2 (en) | 2010-08-03 |
CN1989094A (zh) | 2007-06-27 |
WO2006021857A2 (en) | 2006-03-02 |
EP1784374A2 (en) | 2007-05-16 |
DE602005005206T2 (de) | 2009-03-26 |
ATE388131T1 (de) | 2008-03-15 |
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