CN1249014C - 作为具有麝香特性的芳香剂的环烷羧酸衍生物 - Google Patents
作为具有麝香特性的芳香剂的环烷羧酸衍生物 Download PDFInfo
- Publication number
- CN1249014C CN1249014C CNB028110048A CN02811004A CN1249014C CN 1249014 C CN1249014 C CN 1249014C CN B028110048 A CNB028110048 A CN B028110048A CN 02811004 A CN02811004 A CN 02811004A CN 1249014 C CN1249014 C CN 1249014C
- Authority
- CN
- China
- Prior art keywords
- compound
- methyl
- carboxylic acid
- dimethylcyclohexyl
- moschus
- 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
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- 239000002253 acid Substances 0.000 title abstract description 5
- 241000402754 Erythranthe moschata Species 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 84
- 239000000203 mixture Substances 0.000 claims abstract description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- -1 methyl-propyl Chemical group 0.000 claims description 37
- 239000002304 perfume Substances 0.000 claims description 15
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims description 10
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 claims description 4
- MMEAVAVRZYNYFB-UHFFFAOYSA-N 1,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1CC1(C)C(O)=O MMEAVAVRZYNYFB-UHFFFAOYSA-N 0.000 claims description 2
- DIZKLZKLNKQFGB-UHFFFAOYSA-N 1-methylcyclopropane-1-carboxylic acid Chemical compound OC(=O)C1(C)CC1 DIZKLZKLNKQFGB-UHFFFAOYSA-N 0.000 claims description 2
- AYEGPMGNMOIHDL-UHFFFAOYSA-N 2-methylcyclopropane-1-carboxylic acid Chemical compound CC1CC1C(O)=O AYEGPMGNMOIHDL-UHFFFAOYSA-N 0.000 claims description 2
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- 244000153234 Hibiscus abelmoschus Species 0.000 description 22
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- UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 3
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- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 2
- NGYMOTOXXHCHOC-UHFFFAOYSA-N 3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pentan-2-ol Chemical compound CC(O)C(C)CCC1CC=C(C)C1(C)C NGYMOTOXXHCHOC-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- AXISYYRBXTVTFY-UHFFFAOYSA-N Isopropyl tetradecanoate Chemical class CCCCCCCCCCCCCC(=O)OC(C)C AXISYYRBXTVTFY-UHFFFAOYSA-N 0.000 description 2
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
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- 238000005194 fractionation Methods 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- ONKNPOPIGWHAQC-UHFFFAOYSA-N galaxolide Chemical compound C1OCC(C)C2=C1C=C1C(C)(C)C(C)C(C)(C)C1=C2 ONKNPOPIGWHAQC-UHFFFAOYSA-N 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- HIGQPQRQIQDZMP-DHZHZOJOSA-N geranyl acetate Chemical compound CC(C)=CCC\C(C)=C\COC(C)=O HIGQPQRQIQDZMP-DHZHZOJOSA-N 0.000 description 1
- 239000001927 guaiacum sanctum l. gum oil Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229940087305 limonene Drugs 0.000 description 1
- 235000001510 limonene Nutrition 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 150000002678 macrocyclic compounds Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 235000019645 odor Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000001738 pogostemon cablin oil Substances 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229930194459 prunolide Natural products 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000010666 rose oil Substances 0.000 description 1
- 235000019719 rose oil Nutrition 0.000 description 1
- 229930007790 rose oxide Natural products 0.000 description 1
- 239000001290 saussurea lappa clarke root oil Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 1
- 229940071536 silver acetate Drugs 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- LFSYLMRHJKGLDV-UHFFFAOYSA-N tetradecanolide Natural products O=C1CCCCCCCCCCCCCO1 LFSYLMRHJKGLDV-UHFFFAOYSA-N 0.000 description 1
- CZCBTSFUTPZVKJ-UHFFFAOYSA-N trans-Rosenoxid Natural products CC1CCOC(C=C(C)C)C1 CZCBTSFUTPZVKJ-UHFFFAOYSA-N 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- PHXATPHONSXBIL-UHFFFAOYSA-N xi-gamma-Undecalactone Chemical compound CCCCCCCC1CCC(=O)O1 PHXATPHONSXBIL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- 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
- C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
- C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Medicines Containing Plant Substances (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Description
化合物/成分 | 重量份1/1000 | |
1 | 琥珀缩酮(amberketal)@10%,在IPM(肉豆蔻酸异丙基酯)中 | 20 |
2 | 黄葵内酯 | 6 |
3 | 水杨酸戊酯 | 7 |
4 | BHT(丁基羟基甲苯)@10%,在DPG(二丙二醇)中 | 5 |
5 | Calone 1951(7-甲基-3,4-二氢-2H-1,5-苯并dioxepin-3-酮)@10%,在DPG中 | 3 |
6 | 小豆蔻油纯 | 2 |
7 | Cashmeran(1,2,3,5,6,7-六氢-1,1,2,3,3-五甲基-4H-茚-4-酮) | 1 |
8 | 柑橘精油,无色,无柠檬油精 | 35 |
9 | 香茅醇,左旋@10%,在DPG中 | 3 |
10 | 环六l(4-4-羟基-4-甲基戊基)环己-3-烯-1-甲醛) | 50 |
11 | 二甲基苯基乙基甲醇(2-甲基-4-苯基丁烷-2-醇)@10%,在DPG中 | 2 |
12 | 乙基里哪醇(3,7-二甲基壬-1,6-二烯-3-醇) | 70 |
13 | 十三烷二酸亚乙基酯 | 200 |
14 | ″Fruit Vert GR3″香料基(Givaudan) | 8 |
15 | Galaxolide 50 PHT | 150 |
16 | ″Galbex 183 E″香料基(Firmenich) | 5 |
17 | 愈创木油 | 8 |
18 | Habanolide(氧杂环十六-12/13-烯2-酮) | 20 |
19 | Hedione HC(顺式-甲基(3-氧代-2-戊基环戊基)乙酸酯 | 7 |
20 | 羟基香茅醛,合成 | 7 |
21 | IPM(肉豆蔻酸异丙基酯) | 100 |
22 | Iso E Super(1-(1,2,3,4,5,6,7,8-八氢-2,3,8,8-四甲基-2-萘基)乙酮) | 95 |
23 | 异丁子香酸@1%,在DPG中 | 5 |
24 | 熏衣草油,法国,″orpur″ | 7 |
25 | 里哪醇,合成 | 10 |
26 | 乙酸里哪酯 | 20 |
27 | 柑橘油,意大利,″orpur″ | 5 |
28 | Muscenone(3-甲基环十五-4/5-烯酮)(3-methylcyclopentadec-4/5-enone) | 10 |
29 | 肉豆蔻油 | 7 |
30 | pyralone@10%,在DPG中 | 2 |
31 | Thibetolide(环十五内酯) | 80 |
32 | 托品醛(α-甲基-1,3-苯并-间二氧杂环戊烯-5-丙醛) | 10 |
33 | 化合物(5) | 40 |
1000 |
化合物/成分 | 重量份1/800 | |
1 | α-己基肉桂醛 | 210 |
2 | 苯甲醛@10%,在DPG中 | 1 |
3 | 乙酸苄酯,特级 | 35 |
4 | 苄基醇,特级 | 5 |
5 | β-紫罗酮 | 9 |
6 | 肉桂醛 | 2 |
7 | 顺式-3-十二烯醛(柑橘醛)@10%,在DPG中 | 5 |
8 | 香豆素,纯,结晶 | 10 |
9 | 二丙二醇(DPG) | 123 |
10 | 8-乙基-1-氧杂螺[4.5]癸-2-酮(乙基laitone)@1%,在TEC中 | 5 |
11 | 乙基麦芽酚@1%,在DPG中 | 8 |
12 | 乙基香草醛 | 5 |
13 | 丁子香酚,纯 | 2 |
14 | 香叶醇 | 50 |
15 | Geranitril T(3,7-二甲基-2,6-辛二烯-腈) | 2 |
16 | 乙酸香叶酯,合成 | 5 |
17 | 羟基香茅醛,合成 | 10 |
18 | 月桂醛@10%,在DPG中 | 5 |
19 | Lemarome N | 3 |
20 | 里哪醇,合成 | 50 |
21 | 乙酸里哪酯,合成 | 60 |
22 | Prunolide(γ-壬内酯) | 20 |
23 | Sandalore(5-(2,2,3-三甲基环戊-3-烯-1-基)-3-甲基戊-2-醇) | 60 |
24 | 萜品醇,纯 | 5 |
25 | 三环萜醛(2,4-二甲基环己-3-烯-1-甲醛) | 3 |
26 | 香草醛 | 2 |
27 | Yara Yara(2-甲氧基萘)@10%,在DPG中 | 5 |
28 | 化合物(5) | 100 |
800 |
Claims (6)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP01113377.4 | 2001-06-01 | ||
EP01113377A EP1262474A1 (en) | 2001-06-01 | 2001-06-01 | Cycloalkanecarboxylic acid derivatives as fragrants with musk characteristics |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1512980A CN1512980A (zh) | 2004-07-14 |
CN1249014C true CN1249014C (zh) | 2006-04-05 |
Family
ID=8177615
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB028110048A Expired - Lifetime CN1249014C (zh) | 2001-06-01 | 2002-05-30 | 作为具有麝香特性的芳香剂的环烷羧酸衍生物 |
Country Status (10)
Country | Link |
---|---|
US (1) | US7390779B2 (zh) |
EP (2) | EP1262474A1 (zh) |
JP (1) | JP4200094B2 (zh) |
CN (1) | CN1249014C (zh) |
AT (1) | ATE381530T1 (zh) |
BR (1) | BR0210098B1 (zh) |
DE (1) | DE60224180T2 (zh) |
ES (1) | ES2298366T3 (zh) |
MX (1) | MXPA03010828A (zh) |
WO (1) | WO2002096852A1 (zh) |
Families Citing this family (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB0204919D0 (en) * | 2002-03-01 | 2002-04-17 | Cst Medical Ltd | Treatment of female sexual dysfunction |
GB0227807D0 (en) * | 2002-11-29 | 2003-01-08 | Givaudan Sa | Improvements in or relating ot organic compounds |
ES2274282T3 (es) * | 2002-11-29 | 2007-05-16 | Givaudan Sa | Compuestos alifaticos utilizables como fragancias, con caracteristicas de almizcle. |
EP1459735B1 (en) * | 2003-03-19 | 2006-06-07 | Firmenich Sa | Odorant compounds |
DE10335053A1 (de) * | 2003-07-31 | 2005-02-24 | Symrise Gmbh & Co. Kg | Alicyclische Ester mit Moschusgeruch |
GB0410134D0 (en) * | 2004-05-07 | 2004-06-09 | Givaudan Sa | Organic compounds |
US20060133415A1 (en) * | 2004-12-21 | 2006-06-22 | Mueller Peter D | Wireless internetwork transfer apparatus, systems, and methods |
EP2079487A1 (en) * | 2006-10-24 | 2009-07-22 | Givaudan SA | Malodor counteracting compositions |
ATE499973T1 (de) * | 2007-09-07 | 2011-03-15 | Givaudan Sa | Dimethylcyclohexyl-derivate als mittel zur neutralisation unangenehmer gerüche |
JP5442356B2 (ja) * | 2009-08-11 | 2014-03-12 | 長谷川香料株式会社 | 脂肪族エステル類、該化合物を含有する香料組成物および該化合物の製造法 |
US9157048B2 (en) * | 2010-10-25 | 2015-10-13 | Symrise Ag | Perfume |
EP3135663B1 (en) * | 2014-04-21 | 2019-02-27 | Takasago International Corporation | Novel compound, and flavor composition containing said compound |
EP3446676B1 (en) * | 2016-04-20 | 2020-09-16 | LG Household & Health Care Ltd. | Aroma composition |
JP7391017B2 (ja) | 2017-10-06 | 2023-12-04 | カーギル インコーポレイテッド | ステビオール配糖体溶解度エンハンサー |
CN107759445A (zh) * | 2017-11-23 | 2018-03-06 | 帕潘纳(北京)科技有限公司 | 一种制备1‑(3,3,‑二甲基环己基)乙醇的方法 |
WO2020125993A1 (en) | 2018-12-20 | 2020-06-25 | Symrise Ag | Alicyclic musk fragrance compounds |
EP3952667A1 (en) | 2019-04-06 | 2022-02-16 | Cargill, Incorporated | Sensory modifiers |
WO2021204380A1 (en) | 2020-04-08 | 2021-10-14 | Symrise Ag | Esters as fragrance compounds |
CN111333509B (zh) * | 2020-04-14 | 2022-06-10 | 东莞波顿香料有限公司 | 苹果风味化合物及其制备方法和食品添加剂 |
EP4402230A1 (en) | 2021-09-13 | 2024-07-24 | Symrise AG | Cyclopropanated fragrance compounds |
WO2023209139A1 (en) * | 2022-04-29 | 2023-11-02 | Firmenich Sa | Musky odorant |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5166412A (en) | 1990-08-28 | 1992-11-24 | Firmenich S.A. | Esters and their use in perfumery |
US5767305A (en) * | 1997-04-03 | 1998-06-16 | International Flavors & Fragrances Inc. | Cyclopropyl carboxylic acid esters and uses thereof in imparting, augmenting and enhancing aromas |
DE69905136T2 (de) * | 1998-09-09 | 2003-10-09 | Firmenich S.A., Genf/Geneve | Ester mit moschusgeruch und ihre anwendung in der parfümerie |
-
2001
- 2001-06-01 EP EP01113377A patent/EP1262474A1/en not_active Withdrawn
-
2002
- 2002-05-30 WO PCT/CH2002/000282 patent/WO2002096852A1/en active IP Right Grant
- 2002-05-30 ES ES02727147T patent/ES2298366T3/es not_active Expired - Lifetime
- 2002-05-30 US US10/478,626 patent/US7390779B2/en not_active Expired - Lifetime
- 2002-05-30 BR BRPI0210098-3B1A patent/BR0210098B1/pt active IP Right Grant
- 2002-05-30 EP EP02727147A patent/EP1392640B1/en not_active Expired - Lifetime
- 2002-05-30 MX MXPA03010828A patent/MXPA03010828A/es active IP Right Grant
- 2002-05-30 AT AT02727147T patent/ATE381530T1/de not_active IP Right Cessation
- 2002-05-30 JP JP2003500032A patent/JP4200094B2/ja not_active Expired - Lifetime
- 2002-05-30 CN CNB028110048A patent/CN1249014C/zh not_active Expired - Lifetime
- 2002-05-30 DE DE60224180T patent/DE60224180T2/de not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
US20040234568A1 (en) | 2004-11-25 |
JP4200094B2 (ja) | 2008-12-24 |
EP1392640B1 (en) | 2007-12-19 |
JP2004535412A (ja) | 2004-11-25 |
BR0210098B1 (pt) | 2013-07-16 |
DE60224180D1 (de) | 2008-01-31 |
US7390779B2 (en) | 2008-06-24 |
CN1512980A (zh) | 2004-07-14 |
ATE381530T1 (de) | 2008-01-15 |
DE60224180T2 (de) | 2008-12-11 |
EP1392640A1 (en) | 2004-03-03 |
BR0210098A (pt) | 2004-04-13 |
ES2298366T3 (es) | 2008-05-16 |
WO2002096852A1 (en) | 2002-12-05 |
EP1262474A1 (en) | 2002-12-04 |
MXPA03010828A (es) | 2004-02-17 |
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GR01 | Patent grant | ||
EE01 | Entry into force of recordation of patent licensing contract |
Assignee: Shanghai qihuadun Co. Ltd. Assignor: Givaudan S. A. Contract fulfillment period: 2007.1.1 to 2012.12.31 Contract record no.: 2009990001148 Denomination of invention: Cycloalkanecarboxylic acid derivatives as fragrants with musk characteristics Granted publication date: 20060405 License type: Exclusive license Record date: 20091014 |
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Assignee: Shanghai qihuadun Co. Ltd. Assignor: Givaudan S. A. Contract record no.: 2009990001148 Date of cancellation: 20100805 |
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Assignee: Chiverton daily Flavors & fragrances (Shanghai) Co., Ltd. Assignor: Givaudan SA Contract record no.: 2010990000597 Denomination of invention: Cycloalkanecarboxylic acid derivatives as fragrants with musk characteristics Granted publication date: 20060405 License type: Exclusive License Open date: 20040714 Record date: 20100805 |
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