WO2004035017A1 - Cyclooct-(en-)yl derivatives for use as fragrances - Google Patents
Cyclooct-(en-)yl derivatives for use as fragrances Download PDFInfo
- Publication number
- WO2004035017A1 WO2004035017A1 PCT/CH2003/000660 CH0300660W WO2004035017A1 WO 2004035017 A1 WO2004035017 A1 WO 2004035017A1 CH 0300660 W CH0300660 W CH 0300660W WO 2004035017 A1 WO2004035017 A1 WO 2004035017A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- cyclooct
- compound
- formula
- bond
- dotted line
- Prior art date
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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
- C11B9/0038—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing more than six carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/13—Monohydroxylic alcohols containing saturated rings
- C07C31/133—Monohydroxylic alcohols containing saturated rings monocyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/05—Alcohols containing rings other than six-membered aromatic rings
- C07C33/16—Alcohols containing rings other than six-membered aromatic rings containing rings with more than six ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/30—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/512—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being a free hydroxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/29—Saturated compounds containing keto groups bound to rings
- C07C49/307—Saturated compounds containing keto groups bound to rings to a seven- to twelve-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/527—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings
- C07C49/547—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings to a seven- to twelve-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/527—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings
- C07C49/557—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings having unsaturation outside the rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
Definitions
- This invention relates to substituted cyclooctenes having agrestic, natural, and floral, green, woody odour notes, their manufacture, and to fragrance compositions containing them.
- odour notes imparted by cyclooct-4-en aldehyde (1 ) may be interesting in their own right, in the fragrance industry, there is always an ongoing demand for new compounds that enhance or improve on odour notes, or impart ' new odour notes.
- the invention refers to the use of a compound of formula I as fragrance,
- X is carbonyl, or -(CHOH)- ;
- R is methyl or ethyl, or linear or branched C 3 to C 5 alkyl, such as /-propyl, r/-propyl, n- butyl, sec-butyl, terf-butyl, /.-pentyl, sec-pentyl, and .ert-pentyl; or
- R is vinyl, or linear or branched C 3 to C 5 alkenyl, such as propen-1-yl, propen-2-yl, allyl, but-1-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, and pentenyl; and the dotted line represents one optional double bond.
- the compounds according to the present invention may contain one or more chiral centres and as such may exist as a mixture of stereoisomers, or they may be resolved as isomerically pure forms. Resolving stereoisomers adds to the complexity of manufacture and purification of these compounds and so it is preferred to use the compounds as mixtures of their stereoisomers simply for economic reasons. However, if it is desired to prepare individual stereoisomers, this may be achieved according to methodology known in the art, e.g. preparative HPLC and GC or by stereoselective syntheses.
- Preferred compounds of formula I are 1-cyclooct-3-enylethanone, 1-cyclooct-3- enylpropan-1 -one, 1 -cyclooct-3-enyl-2-methylpropan-1 -one, 1 -cyclooct-3-enylpropan-1 - ol, 1-cyclooct-4-enylethanone, 1 -cyclooct-2-enylethanone, 1-cyclooct-2-enylethanol, 1- cyclooct-1-enylethanone, 1-cyclooctylpropanone, 1-cyclooctyl-2-methylpropanone, and 1-cyclooctyl-2-methylpropanol.
- one optional double bond refers to compounds of formula I wherein the bond between C-1 and C-2 together with the dotted line represents a double bond, and the bonds between C-2 and C-3, C-3 and C- 4, and C-4 and C-5 represent each a single bond; or the bond between C-2 and C-3 together with the dotted line represents a double bond, and the bonds between C-1 and C-2, C-3 and C-4, and C-4 and C-5 represent each a single bond; or the bond between C-3 and C-4 together with the dotted line represents a double bond, and the bonds between C-1 and C-2, C-2 and C-3, and C-4 and C-5 represent each a single bond; or the bond between C-4 and C-5 together with the dotted line represents a double bond, and the bonds between C-1 and C-2, C-2 and C-3, and C-3 and C-4 represent each a single bond; or the bonds between C-1 and C-2, C-2 and C-3, and C-3 and C-4 represent each a single bond; or the bonds between C-1 and C-2, C-2 and
- the compounds according to the present invention may be used alone or in combination with known odourant molecules selected from the extensive range of natural products and synthetic molecules currently available, such as essential oils, alcohols, aldehydes and ketones, ethers and acetals, esters and lactones, macrocycles and heterocycles, and/or in admixture with one or more ingredients or excipients conventionally used in conjunction with odourants in fragrance compositions, for example, carrier materials, and other auxiliary agents commonly used in the art.
- known odourant molecules selected from the extensive range of natural products and synthetic molecules currently available, such as essential oils, alcohols, aldehydes and ketones, ethers and acetals, esters and lactones, macrocycles and heterocycles, and/or in admixture with one or more ingredients or excipients conventionally used in conjunction with odourants in fragrance compositions, for example, carrier materials, and other auxiliary agents commonly used in the art.
- alcohols farnesol, geraniol, linalool, nerol, phenylethyl alcohol, rhodinol, cinnamic alcohol, (Z)-hex-3-en-1-ol, menthol, ⁇ -terpineol.
- aldehydes citral, -hexyl cinnamaldehyde, Lilial, methylionone, verbenone, nootkatone, geranylacetone.
- esters allyl phenoxyacetate, benzyl salicylate, cinnamyl propionate, citronellyl acetate, decyl acetate, dimethylbenzylcarbinyl acetate, dimethylbenzylcarbinyl butyrate, ethyl acetoacetate, cis-3-hexenyl isobutyrate, cis-3-hexenyl salicylate, linalyl acetate, methyl dihydrojasmonate, styralyl propionate, vetiveryl acetate, benzyl acetate, geranyl acetate.
- lactones ⁇ -undecalactone, ⁇ -decalactone, pentadecanolide, 12-oxahexadecanolide.
- acetals Viridine (phenylacetaldehyde dimethylacetal). other components often used in perfumery: indole, p-mentha-8-thiol-3-one, methyleugenol, eugenol, anethol.
- the present invention refers in a further aspect to a fragrance composition
- a fragrance composition comprising a mixture of A) a compound of formula Ic; and B) at least one compound selected from a compound of formula la, a compound of formula lb, and a compound of formula Id
- mixtures comprising a compound of formula la, a compound of formula Ic, and a compound of formula Id.
- the compounds of the present invention may be used in a broad range of fragrance applications, e.g. in any field of fine and functional perfumery.
- the compounds can be employed in wide ranging amounts depending upon the specific application and on the nature and quantity of other odourant ingredients, that may be for example, from about 0.001 to about 20 weight percent of the application.
- compounds may be employed in a fabric softener in an amount of about 0.001 to 0.05 weight percent.
- compounds of the present invention may be used in an alcoholic solution in amounts of about 0.1 to 20 weight percent, more preferably between about 0.1 and 5 weight percent.
- these values should not be regarded as limiting the present invention, since the experienced perfumer may also achieve effects or may create novel accords with lower or higher concentrations.
- the compounds of the present invention may be employed into the fragrance application simply by direct mixing the compound of the present invention or the fragrance composition comprising the compound with the fragrance application. Alternatively, they may be added in an entrapped form, by being in a previous step entrapped with an entrapment material, for example polymers, capsules, microcapsules and nanocapsules, liposomes, precursors, film formers, absorbents, for example by using carbon or zeolites, cyclic oligosaccharides and mixtures thereof, and then mixed with the application.
- an entrapment material for example polymers, capsules, microcapsules and nanocapsules, liposomes, precursors, film formers, absorbents, for example by using carbon or zeolites, cyclic oligosaccharides and mixtures thereof, and then mixed with the application.
- the invention additionally provides a method of manufacturing a fragrance application, comprising the incorporation of a compound of formula I as a fragrance ingredient, either by directly admixing the compound of formula I into the application or by admixing a fragrance composition comprising a compound of formula I, which may then be mixed to a fragrance application, using conventional techniques and methods.
- fragment application means any product, such as fine perfumery, e.g. perfume and Eau de Toilette; household products, e.g. detergents for dishwasher, surface cleaner; laundry products, e.g. softener, bleach, detergent; body care products, e.g. shampoo, shower gel; and cosmetics, e.g. deodorant, vanishing creme, comprising an odourant.
- fine perfumery e.g. perfume and Eau de Toilette
- household products e.g. detergents for dishwasher, surface cleaner
- laundry products e.g. softener, bleach, detergent
- body care products e.g. shampoo, shower gel
- cosmetics e.g. deodorant, vanishing creme
- X is carbonyl, or -(CHOH)- ; and R is methyl or ethyl, or linear or branched C 3 to C 5 alkyl, such as /-propyl, n-propyl, n- butyl, sec-butyl, terf-butyl, n-pentyl, sec-pentyl, and terf-pentyl; or R is vinyl or linear or branched C 3 to C s alkenyl, such as propen-1-yl, propen-2-yl, allyl, but-1-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, and pentenyl; and the dotted line represents one optional double bond; provided that when X is carbonyl and one of the bonds between C-1 and C-2, C-2 and C-3, and C-3 and C-4 together with the dotted line is a double bond, R is not methyl or ethyl; when X is carbony
- a double bond isomeric mixture of compounds of formula I i.e. a mixture of substituted cyclooct-1-enes, -3-enes and -4-enes, may be prepared by addition of an alkanoic acid chloride to cyclooctene followed by dehydrochlorination of the resulting chloro-cyclootyl alkanone under conditions known to the person skilled in the art.
- Example 1 1-cvclooct-3-enylethanone
- Odour description agrestic, armoise, wormwood, thujone, natural.
- Example 2 Obtained according to the experimental procedure of Example 1 from cyclooctene (150 g, 1.36 mol), propionic anhydride (354 g, 2.72 mol) and zinc bromide (30.6 g, 0.14 mol) in 27% yield. Boiling point 60°C/80 mbar.
- Odour description fruity, banana, tagete.
- Example 2 Obtained according to the synthetic procedure of Example 1 from cyclooctene (150 g, 1.36 mol), isobutyric anhydride (430.3 g, 2.72 mol) and zinc bromide (30.6 g, 0.14 mol) in 33% yield. Boiling point 85°C/80 mbar).
- 1-cyclooct-3-enylpropan-1-one (84.0 g, 0.5 mol) was slowly added to a solution of sodium borohydride (11.9 g, 0.3 mol) in ethanol (330 ml) at 0°C (ice bath), and stirring was continued at room temperature for 4 h.
- the reaction mixture was poured into ice- cold 2N HCI (500 ml) and extracted with MTBE (2 x 200ml).
- Odour description cassie, mimosa, green, moss, natural, forest, fatty
- Odour description green leaves, thuja oil, armoise, fruity.
- Odour description green, thuja oil, wormwood, fruity.
- Odour description fruity, sweet, anisic, minty, terpineol, camphoraceous.
- Odour description agrestic, camphoraceous, armoise, thujone-like, earthy, woody.
- Odour description floral, woody, rosy, fruity.
- Example 12 A fragrance composition for a soap :
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/531,809 US7605118B2 (en) | 2002-10-21 | 2003-10-08 | Cyclooct-(en-)yl derivatives for use as fragrances |
JP2005501260A JP4676880B2 (en) | 2002-10-21 | 2003-10-08 | Use of cyclooct- (en-) yl derivatives as perfumes |
DE60328621T DE60328621D1 (en) | 2002-10-21 | 2003-10-08 | CYCLOOCT (EN) YL DERIVATIVES FOR USE AS PERFUMES |
AU2003266093A AU2003266093A1 (en) | 2002-10-21 | 2003-10-08 | Cyclooct-(en-)yl derivatives for use as fragrances |
EP03808655A EP1555998B1 (en) | 2002-10-21 | 2003-10-08 | Cyclooct-(en-)yl derivatives for use as fragrances |
MXPA05002770A MXPA05002770A (en) | 2002-10-21 | 2003-10-08 | Cyclooct-(en-)yl derivatives for use as fragrances. |
AT03808655T ATE437846T1 (en) | 2002-10-21 | 2003-10-08 | CYCLOOCT (EN-)YL DERIVATIVES FOR USE AS FRAGRANCES |
US12/551,889 US7888309B2 (en) | 2002-10-21 | 2009-09-01 | Cyclooct-(en-)yl derivatives for use as fragrances |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB0224379A GB0224379D0 (en) | 2002-10-21 | 2002-10-21 | Improvements in or related to organic compounds |
GB0224379.8 | 2002-10-21 | ||
GB0319350.5 | 2003-08-19 | ||
GB0319350A GB0319350D0 (en) | 2003-08-19 | 2003-08-19 | Improvements in or related to organic compounds |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10531809 A-371-Of-International | 2003-10-08 | ||
US12/551,889 Division US7888309B2 (en) | 2002-10-21 | 2009-09-01 | Cyclooct-(en-)yl derivatives for use as fragrances |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2004035017A1 true WO2004035017A1 (en) | 2004-04-29 |
Family
ID=32109254
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/CH2003/000660 WO2004035017A1 (en) | 2002-10-21 | 2003-10-08 | Cyclooct-(en-)yl derivatives for use as fragrances |
Country Status (10)
Country | Link |
---|---|
US (2) | US7605118B2 (en) |
EP (1) | EP1555998B1 (en) |
JP (1) | JP4676880B2 (en) |
CN (1) | CN1309694C (en) |
AT (1) | ATE437846T1 (en) |
AU (1) | AU2003266093A1 (en) |
DE (1) | DE60328621D1 (en) |
ES (1) | ES2329894T3 (en) |
MX (1) | MXPA05002770A (en) |
WO (1) | WO2004035017A1 (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008071025A1 (en) * | 2006-12-13 | 2008-06-19 | Givaudan Sa | Cycloalkenyl butenones and fragrance compositions comprising them |
WO2019219227A1 (en) * | 2018-05-15 | 2019-11-21 | Givaudan Sa | Organic compounds |
WO2021125255A1 (en) | 2019-12-18 | 2021-06-24 | 持田製薬株式会社 | Novel crosslinked alginic acid |
WO2022145419A1 (en) | 2020-12-28 | 2022-07-07 | 持田製薬株式会社 | Multilayer structure using chemically crosslinked alginic acid |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2024037712A1 (en) | 2022-08-17 | 2024-02-22 | Symrise Ag | 1-cyclooctylpropan-2-one as a fragrance |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4214098A (en) * | 1976-11-01 | 1980-07-22 | Shell Oil Company | Unsaturated alcohols and esters |
DE3610049A1 (en) * | 1985-03-25 | 1986-10-09 | Grau Aromatics GmbH & Co KG, 7070 Schwäbisch Gmünd | Cycloocten-4-yl and bicyclo[3.3.0]octyl ether, their preparation and odoriferous compositions |
WO1999051713A1 (en) * | 1998-04-03 | 1999-10-14 | Cognis Deutschland Gmbh | Use of aldehydes as odorous materials |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2039125C3 (en) * | 1970-08-06 | 1973-08-30 | Studiengesellschaft Kohle Mbh | Process for the production of optically active hydrocarbons from optically inactive hydrocarbons with C-C linkage with the aid of catalysts containing optically active centers |
US4067900A (en) * | 1975-08-25 | 1978-01-10 | Monsanto Company | Hydrogenolysis of alcohols, ketones, aldehydes, esters and ethers |
EP0531715B1 (en) * | 1991-08-08 | 1997-11-05 | Sumitomo Chemical Company Limited | Process for producing alcohols and ketones |
US6252118B1 (en) * | 2000-05-26 | 2001-06-26 | Chul Ho Jun | Method for the preparation of ketones |
US6869598B2 (en) * | 2002-03-22 | 2005-03-22 | Unilever Home & Personal Care Usa Division Of Conopco, Inc. | Stabilization of sunscreens in cosmetic compositions |
-
2003
- 2003-10-08 ES ES03808655T patent/ES2329894T3/en not_active Expired - Lifetime
- 2003-10-08 AU AU2003266093A patent/AU2003266093A1/en not_active Abandoned
- 2003-10-08 WO PCT/CH2003/000660 patent/WO2004035017A1/en active Application Filing
- 2003-10-08 US US10/531,809 patent/US7605118B2/en active Active
- 2003-10-08 JP JP2005501260A patent/JP4676880B2/en not_active Expired - Lifetime
- 2003-10-08 EP EP03808655A patent/EP1555998B1/en not_active Expired - Lifetime
- 2003-10-08 CN CNB2003801007474A patent/CN1309694C/en not_active Expired - Lifetime
- 2003-10-08 AT AT03808655T patent/ATE437846T1/en not_active IP Right Cessation
- 2003-10-08 DE DE60328621T patent/DE60328621D1/en not_active Expired - Lifetime
- 2003-10-08 MX MXPA05002770A patent/MXPA05002770A/en active IP Right Grant
-
2009
- 2009-09-01 US US12/551,889 patent/US7888309B2/en not_active Expired - Lifetime
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4214098A (en) * | 1976-11-01 | 1980-07-22 | Shell Oil Company | Unsaturated alcohols and esters |
DE3610049A1 (en) * | 1985-03-25 | 1986-10-09 | Grau Aromatics GmbH & Co KG, 7070 Schwäbisch Gmünd | Cycloocten-4-yl and bicyclo[3.3.0]octyl ether, their preparation and odoriferous compositions |
WO1999051713A1 (en) * | 1998-04-03 | 1999-10-14 | Cognis Deutschland Gmbh | Use of aldehydes as odorous materials |
Non-Patent Citations (1)
Title |
---|
DIXON J.R., ET AL.: "Mass Spectral Data of Cyclooctyl Derivatives", JOURNAL OF CHEMICAL AND ENGINEERING DATA, vol. 20, no. 1, pages 123 - 124, XP001157123 * |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008071025A1 (en) * | 2006-12-13 | 2008-06-19 | Givaudan Sa | Cycloalkenyl butenones and fragrance compositions comprising them |
WO2019219227A1 (en) * | 2018-05-15 | 2019-11-21 | Givaudan Sa | Organic compounds |
WO2019219743A1 (en) * | 2018-05-15 | 2019-11-21 | Givaudan Sa | Organic compounds |
US11426339B2 (en) | 2018-05-15 | 2022-08-30 | Givaudan Sa | Organic compounds |
WO2021125255A1 (en) | 2019-12-18 | 2021-06-24 | 持田製薬株式会社 | Novel crosslinked alginic acid |
WO2022145419A1 (en) | 2020-12-28 | 2022-07-07 | 持田製薬株式会社 | Multilayer structure using chemically crosslinked alginic acid |
Also Published As
Publication number | Publication date |
---|---|
AU2003266093A1 (en) | 2004-05-04 |
EP1555998A1 (en) | 2005-07-27 |
ES2329894T3 (en) | 2009-12-02 |
US7605118B2 (en) | 2009-10-20 |
ATE437846T1 (en) | 2009-08-15 |
US20090325836A1 (en) | 2009-12-31 |
CN1309694C (en) | 2007-04-11 |
MXPA05002770A (en) | 2005-06-06 |
JP4676880B2 (en) | 2011-04-27 |
US7888309B2 (en) | 2011-02-15 |
JP2006512470A (en) | 2006-04-13 |
CN1694683A (en) | 2005-11-09 |
US20060014663A1 (en) | 2006-01-19 |
EP1555998B1 (en) | 2009-07-29 |
DE60328621D1 (en) | 2009-09-10 |
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