EP1111029A2 - Composition de parfum contenant de la 4,8-dimethyl-3,7-nonadien-2-one - Google Patents
Composition de parfum contenant de la 4,8-dimethyl-3,7-nonadien-2-one Download PDFInfo
- Publication number
- EP1111029A2 EP1111029A2 EP00126525A EP00126525A EP1111029A2 EP 1111029 A2 EP1111029 A2 EP 1111029A2 EP 00126525 A EP00126525 A EP 00126525A EP 00126525 A EP00126525 A EP 00126525A EP 1111029 A2 EP1111029 A2 EP 1111029A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- oil
- dimethyl
- methyl
- nonadien
- alpha
- 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.)
- Withdrawn
Links
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
- C11B9/0007—Aliphatic compounds
- C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
Definitions
- the invention relates to perfume compositions containing 4,8-dimethyl-3,7-nonadien-2-one included and their use.
- fragrances Despite a large number of existing fragrances, the perfume industry does further need for new fragrances, beyond their olfactory properties have additional positive secondary properties, e.g. higher stability, higher yield, better adhesion to textiles and higher stability.
- Perfume compositions were found that have E- and / or Z-4,8-dimethyl-3,7-nonadien-2-one of the formulas contained as a single isomer or as a mixture.
- the compound of the invention is generally a mixture of two isomers in front.
- E- and / or Z-4,8-dimethyl-3,7-nonadien-2-one is new in perfume compositions. It is surprising that E- and / or Z-4,8-dimethyl-3,7-nonadien-2-one not only the known ones in fragrance compositions has olfactory properties, but is strengthened in the composition and so can be perceived even in the smallest quantities.
- compositions are more stable in color than compositions with comparable odor properties.
- E and / or Z-4,8-Dimethyl-3,7-nonadien-2-one instead of other similar fragrances, such as Citronellal or Citral, there are no discolourations in the perfume composition. Color changes in the perfume composition lead to a smaller one Acceptance. It is therefore a goal of the perfume industry to maintain the color stability of perfume compositions to increase.
- 4,8-Dimethyl-3,7-nonadien-2-one also has the surprising property, the fragrance impression to be permanently fixed, visibly refreshed and rounded off.
- E- and / or Z-4,8-dimethyl-3,7-nonadien-2-one is suitable excellent for use in perfume compositions.
- E- and / or Z-4,8-dimethyl-3,7-nonadien-2-one according to the invention can usually be found in small doses in the resulting perfume compositions radiantly fresh, rounded scents achieve, the overall smell strikingly harmonizing, the cosmetic-floral effective radiation is perceptibly increased and the fixation, i.e. the Adhesion of the perfume oil is significantly strengthened.
- fragrances which can be combined according to the invention with E- and / or Z-4,8-dimethyl-3,7-nonadien-2-one to give perfume compositions can be found, for example, in S. Arctander, Perfume and Flavor Materials, Vol. I and II, Montclair , NJ, 1969, self-published or K. Bauer, D. Garbe and H. Surburg, Common Fragrance and Flavor Materials, 3 rd . Ed ., Wiley-VCH , Weinheim 1997.
- Extracts from natural raw materials such as essential oils, concretes, absolute, resins, resinoids, balms, tinctures such as B. Ambratincture; Amyris oil; Angelica seed oil; Angelica root oil; Anise oil; Valerian oil; Basil oil; Baummoos -Absolue; Bay oil; Mugwort oil; Benzoeresin; Bergamot oil; Beeswax absolute; Birch tar oil; Bitter almond oil; Savory oil; Bucco leaf oil; Cabreuva oil; Cade oil; Calmus oil; Camphor oil; Cananga oil; Cardamom oil; Cascarilla oil; Cassia oil; Cassie absolute; Castoreum-absolue; Cedar leaf oil; Cedarwood oil; Cistus oil; Citronell oil; Lemon oil; Copaiva balm; Copaiva balsam oil; Coriander oil; Costus root oil; Cumin oil; Cypress oil; Davana oil; Dill herb oil; Dill seed oil; Eau de brouts absolute;
- the perfume oils containing the compounds according to the invention can be found in liquid form, undiluted or diluted with a solvent for Perfumes are used.
- Suitable solvents for this are e.g. Ethanol, isopropanol, diethylene glycol monoethyl ether, glycerin, propylene glycol, 1,2-butylene glycol, dipropylene glycol, diethyl phthalate, triethyl citrate, Isopropyl myristate etc.
- the perfume oils containing the compounds according to the invention can be adsorbed on a carrier, which is both for a fine distribution of the Fragrances in the product as well as for a controlled release during use worries.
- a carrier which is both for a fine distribution of the Fragrances in the product as well as for a controlled release during use worries.
- Such supports can be porous inorganic materials such as light sulfate, Silica gels, zeolites, gypsum, clays, clay granules, gas concrete etc. or organic Materials like woods and cellulose-based fabrics.
- perfume oils containing the compounds according to the invention can also microencapsulated, spray dried, as inclusion complexes or as extrusion products are available and added in this form to the product to be perfumed become.
- the properties of the perfume oils modified in this way can be changed So-called "coating" with suitable materials with a view to a more targeted fragrance release be further optimized, which is why wax-like plastics such as e.g. Polyvinyl alcohol can be used.
- the microencapsulation of the perfume oils can, for example, by the so-called coacervation process with the help of capsule materials e.g. made of polyurethane-like Fabrics or soft gelatin.
- the spray-dried perfume oils can for example by spray drying an emulsion containing the perfume oil, or dispersion are prepared, modified starches as carriers, Proteins, dextrin and vegetable gums can be used.
- Inclusion complexes can e.g. by adding dispersions of the perfume oil and Cyclodextrins or urea derivatives in a suitable solvent, e.g. Water.
- Extrusion products can be made by fusing the Perfume oils with a suitable waxy substance and by extrusion with subsequent solidification, if necessary in a suitable solvent, e.g. Isopropanol, be preserved.
- the amount used is that of the invention Compounds 0.05 to 50 wt .-%, preferably 0.5 to 20%, based on the entire composition.
- the perfume compositions according to the invention can be in concentrated form, in Solutions or in modified form described above can be used for the Manufacture of fine perfumery products and industrial products.
- Fine perfumery products and industrial products are e.g. Perfume Extraits, Eau de Perfumes, eau de toilettes, aftershaves, eau de colognes, pre-shave products, Splash colognes and scented refreshing towels as well as scented acidic, alkaline or neutral cleaning agents, e.g.
- Skin creams and lotions face creams and lotions, sunscreen creams and lotions, after-sun creams and lotions, hand creams and lotions, foot creams and lotions, depilatory creams and lotions, After-shave creams and lotions, tanning creams and lotions, hair care products such as.
- hair styling agents such as Cold waves and hair straighteners, hair lotions, hair creams and lotions, deodorants and antiperspirants such as Armpit sprays, roll-ons, deosticks, deocremes
- Decorative cosmetics products such as Eye shadows, nail polishes, Make-ups, lipsticks, mascara and candles, lamp oils, incense sticks, Insecticides, repellents, fuels.
- the amount of perfume composition 0.1 to 40 wt .-%, preferably 0.5 to 20 wt .-%, based on the Final product.
- 4,8-Dimethyl-3,7-nonadien-2-one can advantageously be obtained from 4,8-dimethyl-3,7-nonadien-2-ol be manufactured, e.g. by a Grignard reaction of citral and methyl magnesium chloride was synthesized (Indian Perfum., 1983, 27, 112-18).
- the Oxidation to 4,8-dimethyl-3,7-nonadien-2-one is known (e.g. C. Aguilar et al. Bol.
- An advantageous process for the preparation of 4,8-dimethyl-3,7-nonadien-2-one is characterized in that 4,8-dimethyl-3,7-nonadien-2-ol in the presence of a
- Catalyst and a hydrogen acceptor is implemented.
- This reaction dispenses with critical reagents and is also problem-free larger scale feasible.
- Aluminum alkoxides such as aluminum tri-tertiary butylate and Aluminum triisopropylate, preferably aluminum triisopropylate can be used.
- the reaction temperature is between 40 ° C and reflux temperature, preferably between 60-120 ° C.
- the known compounds can be used as the hydrogen acceptor (Org. Reactions, Vol. 6, pp.207-272).
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)
- Cosmetics (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19961598A DE19961598A1 (de) | 1999-12-21 | 1999-12-21 | Parfümkomposition enthaltend 4,8-Dimethyl-3,7-nonadien-2-on |
DE19961598 | 1999-12-21 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP1111029A2 true EP1111029A2 (fr) | 2001-06-27 |
EP1111029A3 EP1111029A3 (fr) | 2003-10-22 |
Family
ID=7933515
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP00126525A Withdrawn EP1111029A3 (fr) | 1999-12-21 | 2000-12-08 | Composition de parfum contenant de la 4,8-dimethyl-3,7-nonadien-2-one |
Country Status (4)
Country | Link |
---|---|
US (1) | US20010005711A1 (fr) |
EP (1) | EP1111029A3 (fr) |
JP (1) | JP2001181670A (fr) |
DE (1) | DE19961598A1 (fr) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003022979A1 (fr) * | 2001-09-06 | 2003-03-20 | The Procter & Gamble Company | Chandelles parfumees |
CN104837798A (zh) * | 2012-12-20 | 2015-08-12 | 弗门尼舍有限公司 | 鼠尾草添味剂 |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2376245C (en) * | 2001-04-09 | 2005-10-31 | Simon John Murray | Fruit Flavoured/Fragranced Wipes |
EP1536762B1 (fr) * | 2002-09-10 | 2007-01-17 | Takasago International Corporation | Compositions comportant des emulsions aqueuses de silicone et produits parfumes et de soins capillaires comprenant de telles compositions |
US7097872B2 (en) * | 2002-11-08 | 2006-08-29 | International Flavors & Fragrances Inc. | Fruit, berry, cranberry and hedonically-stable citrus flavored compositions and process for preparing same |
DE10330865A1 (de) * | 2003-07-09 | 2005-01-27 | Symrise Gmbh & Co. Kg | 4,8-Dimethyl-7-nonen-2-on und 4,8-Dimethylnonan-2-on als Riechstoffe |
WO2005046632A2 (fr) * | 2003-11-17 | 2005-05-26 | Patus Ltd. | Composition efficace pour modifier la perception d'une mauvaise odeur |
EP1882027B1 (fr) * | 2005-05-13 | 2010-07-21 | Firmenich Sa | Thiols en tant qu'ingredient aromatique |
GB0518558D0 (en) * | 2005-09-12 | 2005-10-19 | Givaudan Sa | Improvements in or related to organic compounds |
JP2008101129A (ja) * | 2006-10-19 | 2008-05-01 | Shiono Koryo Kk | 香料組成物およびそれが配合された化粧料 |
US20090088519A1 (en) * | 2007-10-01 | 2009-04-02 | O'brien Stickney Janese Christine | Furniture polish compositions substantially free of organic solvents |
JP5027937B2 (ja) * | 2011-01-31 | 2012-09-19 | 小川香料株式会社 | 香料組成物 |
US9217121B2 (en) | 2013-01-25 | 2015-12-22 | Basf Se | Use of 4,8 dimethyl-3,7 nonadien-2-ol as fragrance |
JP6289505B2 (ja) * | 2013-01-25 | 2018-03-07 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 香料としての4,8−ジメチル−3,7−ノナジエン−2−オールの使用 |
EP3183231B1 (fr) * | 2014-08-20 | 2019-10-09 | Bedoukian Research, Inc. | Compositions de parfum contenant des alcadiènenitriles isomères |
JP7258449B2 (ja) * | 2021-03-19 | 2023-04-17 | 長谷川香料株式会社 | 化合物およびこれを用いた香味付与組成物 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3932462A (en) * | 1972-11-17 | 1976-01-13 | Basf Aktiengesellschaft | Manufacture of unsaturated ketones |
US3954804A (en) * | 1972-04-08 | 1976-05-04 | Basf Aktiengesellschaft | Production of high molecular weight unsaturated ketones |
WO2001043567A1 (fr) * | 1999-12-16 | 2001-06-21 | Haarmann & Reimer Gmbh | Aromes et compositions d'aromes contenant du 4,8-dimethyl-3,7-nonadiene-2-one et procede permettant de les produire |
-
1999
- 1999-12-21 DE DE19961598A patent/DE19961598A1/de not_active Withdrawn
-
2000
- 2000-12-08 EP EP00126525A patent/EP1111029A3/fr not_active Withdrawn
- 2000-12-11 JP JP2000375778A patent/JP2001181670A/ja active Pending
- 2000-12-13 US US09/736,599 patent/US20010005711A1/en not_active Abandoned
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3954804A (en) * | 1972-04-08 | 1976-05-04 | Basf Aktiengesellschaft | Production of high molecular weight unsaturated ketones |
US3932462A (en) * | 1972-11-17 | 1976-01-13 | Basf Aktiengesellschaft | Manufacture of unsaturated ketones |
WO2001043567A1 (fr) * | 1999-12-16 | 2001-06-21 | Haarmann & Reimer Gmbh | Aromes et compositions d'aromes contenant du 4,8-dimethyl-3,7-nonadiene-2-one et procede permettant de les produire |
Non-Patent Citations (4)
Title |
---|
AGARWAL V K ET AL: "A SEARCH FOR NEW AROMA CHEMICALS. PART IV. CHEMICAL TRANSFORMATIONSOF CITRAL INTO PERFUMERY PRODUCTS" INDIAN PERFUMER, ESSENTIAL OIL ASSOCIATION OF INDIA, KANPUR, IN, Bd. 27, Nr. 2, 1983, Seiten 112-118, XP000994819 ISSN: 0019-607X * |
KURUSU Y ET AL: "CATALYSIS BY TETRABROMOOXOMOLYBDATE(V) COMPLEX: OXIDATION OF OLEFINS AND ALCOHOLS WITH T-BUTYL HYDROPEROXIDE" POLYHEDRON, PERGAMON PRESS, OXFORD, GB, Bd. 5, Nr. 1/2, 1986, Seiten 289-296, XP000994833 ISSN: 0277-5387 * |
MASUYAMA Y ET AL: "CHEMOSELECTIVE OXIDATION WITH MOLYBDENUM CATALYST-T-BUTYL HYDROPEROXIDE" TETRAHEDRON LETTERS, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, Bd. 25, Nr. 39, 1984, Seiten 4417-4420, XP000985898 ISSN: 0040-4039 * |
WEYERSTAHL P ET AL: "CONSTITUENTS OF BRAZILIAN VASSOURA OIL" FLAVOUR AND FLAGRANCE JOURNAL, WILEY, NEW YORK, NY, GB, Bd. 11, Nr. 1, 1996, Seiten 15-23, XP000994831 ISSN: 0882-5734 * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003022979A1 (fr) * | 2001-09-06 | 2003-03-20 | The Procter & Gamble Company | Chandelles parfumees |
EP1992680A3 (fr) * | 2001-09-06 | 2008-11-26 | The Procter and Gamble Company | Bougies parfumées |
CN104837798A (zh) * | 2012-12-20 | 2015-08-12 | 弗门尼舍有限公司 | 鼠尾草添味剂 |
CN104837798B (zh) * | 2012-12-20 | 2017-05-17 | 弗门尼舍有限公司 | 鼠尾草添味剂 |
Also Published As
Publication number | Publication date |
---|---|
DE19961598A1 (de) | 2001-07-05 |
EP1111029A3 (fr) | 2003-10-22 |
US20010005711A1 (en) | 2001-06-28 |
JP2001181670A (ja) | 2001-07-03 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP3206756A1 (fr) | Utilisation d'hexadéca-8,15-diénal en tant que produit chimique aromatique | |
US7638479B2 (en) | 3-methylbenzyl-isobutyrate | |
US20060166857A1 (en) | 4,8-Dimethyl-7-nonen-2-one and 4,8-dimethylnonan-2-one used as perfumes | |
EP1111029A2 (fr) | Composition de parfum contenant de la 4,8-dimethyl-3,7-nonadien-2-one | |
US20170211014A1 (en) | Isomer mixtures of unsaturated macrocyclic musk compounds | |
EP1654246B1 (fr) | Acetals, leur utilisation comme matieres odorantes et leur procede de production | |
EP1599434B1 (fr) | 4-cyclohexyl-2-butanol servant de parfum | |
EP1067126B1 (fr) | Acétales tétracycliques | |
EP1761618B1 (fr) | Utilisation d'un melange de cis- et de trans-3-methyl-g-decalactone, compositions de substances odorantes et articles parfumes contenant ledit melange | |
EP1648526B1 (fr) | Esters cis-3,3,5-trimethylcyclohexyliques | |
EP3112448A1 (fr) | Derives d'ethanols 1-(4-methylcyclohexyl) | |
US20240141254A1 (en) | 2,6,6-trimethyl-norpinan-2-ol as an odoriferous substance | |
KR20240004630A (ko) | 향료로서의 2,4-디메틸옥타-2,7-디엔-4-올 | |
US20070072789A1 (en) | 2-Methyl-5-phenylpentanal used as a rose odoriferous substance | |
DE10229474A1 (de) | Neue Riechstoffe und Verfahren zu ihrer Herstellung | |
DE10222025A1 (de) | Neue ungesättigte makrocyclische Oxalactone | |
DE10325628A1 (de) | 2-Methyl-5-phenylpentanal als Rosenriechstoff | |
DE10324018A1 (de) | 2-Methyl-5-phenylpentanal als Rosenriechstoff |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
AK | Designated contracting states |
Kind code of ref document: A2 Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE TR |
|
AX | Request for extension of the european patent |
Free format text: AL;LT;LV;MK;RO;SI |
|
PUAL | Search report despatched |
Free format text: ORIGINAL CODE: 0009013 |
|
RAP1 | Party data changed (applicant data changed or rights of an application transferred) |
Owner name: SYMRISE GMBH & CO. KG |
|
AK | Designated contracting states |
Kind code of ref document: A3 Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE TR |
|
AX | Request for extension of the european patent |
Extension state: AL LT LV MK RO SI |
|
AKX | Designation fees paid | ||
REG | Reference to a national code |
Ref country code: DE Ref legal event code: 8566 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
|
18D | Application deemed to be withdrawn |
Effective date: 20040423 |