ES2550801T3 - Compuestos y composiciones de fragancia - Google Patents
Compuestos y composiciones de fragancia Download PDFInfo
- Publication number
- ES2550801T3 ES2550801T3 ES12762243.9T ES12762243T ES2550801T3 ES 2550801 T3 ES2550801 T3 ES 2550801T3 ES 12762243 T ES12762243 T ES 12762243T ES 2550801 T3 ES2550801 T3 ES 2550801T3
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- ES
- Spain
- Prior art keywords
- ethyl
- formula
- methyl
- compound
- products
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 34
- 239000000203 mixture Substances 0.000 title claims description 38
- 239000003205 fragrance Substances 0.000 title claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 7
- -1 methylcyclopentylidene Chemical group 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 239000004615 ingredient Substances 0.000 claims description 6
- 239000002386 air freshener Substances 0.000 claims description 3
- OKPKEJYSFLOJKZ-UHFFFAOYSA-N 4-(3,3-dimethylcyclopentylidene)butanal Chemical compound CC1(C)CCC(=CCCC=O)C1 OKPKEJYSFLOJKZ-UHFFFAOYSA-N 0.000 claims description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 2
- 230000002708 enhancing effect Effects 0.000 claims description 2
- 230000003796 beauty Effects 0.000 claims 1
- 239000012437 perfumed product Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 27
- CHCCBPDEADMNCI-UHFFFAOYSA-N 3-Methyl-2-cyclopenten-1-one Chemical compound CC1=CC(=O)CC1 CHCCBPDEADMNCI-UHFFFAOYSA-N 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 6
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- RQWVQZYEZIMEIX-UHFFFAOYSA-N 1-ethenyl-3-ethyl-3-methylcyclopentan-1-ol Chemical compound CCC1(C)CCC(O)(C=C)C1 RQWVQZYEZIMEIX-UHFFFAOYSA-N 0.000 description 4
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 4
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- ASCYPCBZHXTNAM-UHFFFAOYSA-N 1-ethenyl-3,3-dimethylcyclopentan-1-ol Chemical compound CC1(C)CCC(O)(C=C)C1 ASCYPCBZHXTNAM-UHFFFAOYSA-N 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- JSYAQLZSGHPSJD-UHFFFAOYSA-N 3,3-dimethylcyclopentan-1-one Chemical compound CC1(C)CCC(=O)C1 JSYAQLZSGHPSJD-UHFFFAOYSA-N 0.000 description 3
- IUZULRVGAITOOO-UHFFFAOYSA-N 3-ethyl-3-methylcyclopentan-1-one Chemical compound CCC1(C)CCC(=O)C1 IUZULRVGAITOOO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000002304 perfume Substances 0.000 description 3
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- 239000000243 solution Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 2
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 229940022663 acetate Drugs 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 2
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- 239000002979 fabric softener Substances 0.000 description 2
- IFYYFLINQYPWGJ-UHFFFAOYSA-N gamma-decalactone Chemical compound CCCCCCC1CCC(=O)O1 IFYYFLINQYPWGJ-UHFFFAOYSA-N 0.000 description 2
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- KVWWIYGFBYDJQC-UHFFFAOYSA-N methyl dihydrojasmonate Chemical compound CCCCCC1C(CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- VWMVAQHMFFZQGD-UHFFFAOYSA-N p-Hydroxybenzyl acetone Natural products CC(=O)CC1=CC=C(O)C=C1 VWMVAQHMFFZQGD-UHFFFAOYSA-N 0.000 description 2
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- 238000000746 purification Methods 0.000 description 2
- NJGBTKGETPDVIK-UHFFFAOYSA-N raspberry ketone Chemical compound CC(=O)CCC1=CC=C(O)C=C1 NJGBTKGETPDVIK-UHFFFAOYSA-N 0.000 description 2
- CZCBTSFUTPZVKJ-UHFFFAOYSA-N rose oxide Chemical compound CC1CCOC(C=C(C)C)C1 CZCBTSFUTPZVKJ-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000001069 triethyl citrate Substances 0.000 description 2
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 2
- 235000013769 triethyl citrate Nutrition 0.000 description 2
- 239000000341 volatile oil Substances 0.000 description 2
- PHXATPHONSXBIL-UHFFFAOYSA-N xi-gamma-Undecalactone Chemical compound CCCCCCCC1CCC(=O)O1 PHXATPHONSXBIL-UHFFFAOYSA-N 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- CRDAMVZIKSXKFV-FBXUGWQNSA-N (2-cis,6-cis)-farnesol Chemical compound CC(C)=CCC\C(C)=C/CC\C(C)=C/CO CRDAMVZIKSXKFV-FBXUGWQNSA-N 0.000 description 1
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- 239000000171 lavandula angustifolia l. flower oil Substances 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
- 229930007744 linalool Natural products 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 150000002678 macrocyclic compounds Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 1
- YCCXQARVHOPWFJ-UHFFFAOYSA-M magnesium;ethane;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C YCCXQARVHOPWFJ-UHFFFAOYSA-M 0.000 description 1
- 229940043353 maltol Drugs 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002088 nanocapsule Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000001738 pogostemon cablin oil Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 235000019719 rose oil Nutrition 0.000 description 1
- 239000010666 rose oil Substances 0.000 description 1
- 229930007790 rose oxide Natural products 0.000 description 1
- 239000010671 sandalwood oil Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- LFSYLMRHJKGLDV-UHFFFAOYSA-N tetradecanolide Natural products O=C1CCCCCCCCCCCCCO1 LFSYLMRHJKGLDV-UHFFFAOYSA-N 0.000 description 1
- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 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
- DCSCXTJOXBUFGB-UHFFFAOYSA-N verbenone Natural products CC1=CC(=O)C2C(C)(C)C1C2 DCSCXTJOXBUFGB-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000010457 zeolite Substances 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
- C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
- C11B9/003—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing less than six carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/225—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring 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)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB201115409A GB201115409D0 (en) | 2011-09-07 | 2011-09-07 | Organic compounds |
| GB201115409 | 2011-09-07 | ||
| PCT/EP2012/067449 WO2013034657A1 (en) | 2011-09-07 | 2012-09-06 | Fragrance compounds and compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2550801T3 true ES2550801T3 (es) | 2015-11-12 |
Family
ID=44882305
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES12762243.9T Active ES2550801T3 (es) | 2011-09-07 | 2012-09-06 | Compuestos y composiciones de fragancia |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US9109186B2 (enExample) |
| EP (1) | EP2753296B1 (enExample) |
| JP (1) | JP6072797B2 (enExample) |
| CN (1) | CN103764105B (enExample) |
| BR (1) | BR112014005034A2 (enExample) |
| ES (1) | ES2550801T3 (enExample) |
| GB (1) | GB201115409D0 (enExample) |
| MX (1) | MX2014001748A (enExample) |
| SG (1) | SG2014005045A (enExample) |
| WO (1) | WO2013034657A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2981070B1 (fr) * | 2011-10-11 | 2014-01-10 | V Mane Fils | Nouveaux aldehydes cycloalcaniques, leur procede de preparation ainsi que leur utilisation en parfumerie |
| WO2017191331A2 (en) * | 2016-08-15 | 2017-11-09 | Givaudan Sa | Organic compounds |
| EP4103537A1 (en) * | 2020-04-14 | 2022-12-21 | Firmenich SA | Lily of the valley odorant |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3453317A (en) * | 1962-07-11 | 1969-07-01 | Hoffmann La Roche | Unsaturated carbonyl compounds and processes |
| US4477683A (en) * | 1982-05-03 | 1984-10-16 | Givaudan Corporation | 3-Methyl-1-(2,3,4-and 2,4,4-trimethyl-1-cyclopentylidene) pent-2-en-4-one and isomers, and perfume compositions thereof |
| DE3928242A1 (de) * | 1989-08-26 | 1991-02-28 | Basf Ag | Cycloalkylidenderivate |
| ATE263143T1 (de) * | 1999-07-05 | 2004-04-15 | Givaudan Sa | Cyclopentylalkylnitrile und die verwendung von cyclopentylalkyl-derivaten als duftstoffe |
| MX2009006094A (es) * | 2006-12-08 | 2009-08-25 | Mane Fils V | Uso de derivados canfolenicos como ingredientes fragantes en perfumeria y saborizacion. |
| EP1930317A1 (en) * | 2006-12-08 | 2008-06-11 | V. Mane Fils | Use of campholenic derivatives as fragrant ingredients in perfumery and flavouring |
-
2011
- 2011-09-07 GB GB201115409A patent/GB201115409D0/en not_active Ceased
-
2012
- 2012-09-06 WO PCT/EP2012/067449 patent/WO2013034657A1/en not_active Ceased
- 2012-09-06 MX MX2014001748A patent/MX2014001748A/es unknown
- 2012-09-06 CN CN201280042894.XA patent/CN103764105B/zh not_active Expired - Fee Related
- 2012-09-06 ES ES12762243.9T patent/ES2550801T3/es active Active
- 2012-09-06 BR BR112014005034A patent/BR112014005034A2/pt not_active Application Discontinuation
- 2012-09-06 SG SG2014005045A patent/SG2014005045A/en unknown
- 2012-09-06 EP EP12762243.9A patent/EP2753296B1/en active Active
- 2012-09-06 US US14/240,141 patent/US9109186B2/en active Active
- 2012-09-06 JP JP2014528979A patent/JP6072797B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN103764105B (zh) | 2016-03-30 |
| MX2014001748A (es) | 2014-03-31 |
| EP2753296A1 (en) | 2014-07-16 |
| WO2013034657A1 (en) | 2013-03-14 |
| US20140221263A1 (en) | 2014-08-07 |
| CN103764105A (zh) | 2014-04-30 |
| GB201115409D0 (en) | 2011-10-19 |
| US9109186B2 (en) | 2015-08-18 |
| JP2014526571A (ja) | 2014-10-06 |
| SG2014005045A (en) | 2014-04-28 |
| EP2753296B1 (en) | 2015-08-12 |
| JP6072797B2 (ja) | 2017-02-01 |
| BR112014005034A2 (pt) | 2017-03-21 |
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