WO2004108653A1 - Improvements in or related to organic compounds - Google Patents
Improvements in or related to organic compounds Download PDFInfo
- Publication number
- WO2004108653A1 WO2004108653A1 PCT/CH2004/000331 CH2004000331W WO2004108653A1 WO 2004108653 A1 WO2004108653 A1 WO 2004108653A1 CH 2004000331 W CH2004000331 W CH 2004000331W WO 2004108653 A1 WO2004108653 A1 WO 2004108653A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- ethyl
- methylbutyl
- methyl
- hydrogen
- ethylpropyl
- Prior art date
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
- C11B9/0019—Aliphatic compounds containing oxygen as the only heteroatom carbocylic acids; Salts or esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
Definitions
- This invention refers to new alkyl-2-enoic acid esters, their manufacture and their use in flavour and fragrance compositions.
- flavour and fragrance industry is always interested in new compounds that may enhance, improve, or modify the aroma or flavour in foodstuffs and consumable materials.
- alkyl-2-enoic acid ester compounds enhance, improve, or modify flavour notes, in particular fruity notes, e.g. blackberry and strawberry notes.
- the present invention refers in one of its aspects to a flavour or fragrance composition
- a flavour or fragrance composition comprising a compound of formula (I)
- R 1 is C , C 5 , or C 6 linear or branched alkyl, e.g. n-butyl, sec-butyl, terf-butyl, n- pentyl, 3-methyl-butyl, 2-methyl-butyl, 1 -methyl-butyl, 1-ethyl-propyl,1 ,2-dimethyl-propyl, 2-ethylbutyl; and R 2 and R 3 are independently hydrogen, methyl or ethyl, with the proviso that a maximum of one of R 2 and R 3 is hydrogen; with the proviso that if R 2 is hydrogen and R 3 is methyl, R 1 is not butyl or 1 ,3- dimethylbutyl.
- compositions according to the invention are butyl 3-ethylbutenoate, isobutyl 3-ethylbutenoate, pentyl 3-ethylbutenoate, 3- methylbutyl 3-methylpentenoate, 2-methylbutyl pentenoate, 2-methylbutyl 3- methylbuteonate, 2-methylbutyl 3-methylpentenoate, 2-methylbutyl 3-ethylpentenoate, 1 -methyl butyl butenoate, 1-methylbutyl 3-methylpentenoate, 1 -ethylpropyl 3- methyl butenoate and 1 -ethylpropyl 3-methylpentenoate.
- R 1 R 2 R 3 butyl 3-ethylbutenoate butyl ethyl methyl butyl 3-ethylpentenoate butyl ethyl ethyl isobutyl 3-ethylbutenoate isobutyl ethyl methyl isobutyl 3-ethylpentenoate isobutyl ethyl ethyl sec-butyl 3-ethylpentenoate sec-butyl ethyl ethyl pentyl pentenoate pentyl ethyl hydrogen pentyl 3-ethylbutenoate pentyl ethyl methyl pentyl 3-ethylpentenoate pentyl ethyl ethyl
- the compounds of formula (I) may comprise 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 methods known in the art, e.g. preparative HPLC and GC or by stereoselective syntheses.
- the compounds of formula (I) may be used in flavoured products and are useful in modifying, for example, fruity flavours. They may also be used in aromatic, herbal and spicy flavouring.
- Flavoured products for which the compounds of formula (I) are suitable are food and beverages such as breakfast cereals, alcoholic and non-alcoholic beverages, chewing gum, confections and frostings, fruit juices, frozen dairy desserts and mixes, fruit and water ices, gelatins, puddings, hard candy and cough drops, jams and jellies, commercial milk (whole and skim), milk products, processed fruits and fruit juices, soft candy, sweet sauces, toppings and syrups. This list of products is given by way of illustration and is not to be regarded as being in any way limiting.
- the compounds of the present invention may be used in flavoured products alone or in combination with other flavour ingredients known to the person skilled in the art.
- the compounds of formula (I) may be used in fragrance applications, e.g. in any field of fine and functionary perfumery, such as perfumes, household products, laundry products, body care products and cosmetics.
- the compounds of the formula (I) may be present in consumables, e.g. a food, a beverage or a consumer healthcare product, in amounts ranging from 0.5 to 100ppm, more preferably from 1 to 50ppm.
- compounds of the formula (I) can be employed in wide-ranging amounts depending upon the specific application, for example, from about 0.001 to about 10 weight percent.
- One application may be a fabric softener comprising about 0.001 to 0.05 weight percent of the compound.
- Another application may be a perfume, i.e. an alcoholic solution, comprising about 0.1 to 10 weight percent of the compound.
- the preferred concentrations vary between about 0.1 and 5 weight percent. However, these values should not be regarded as limiting on the present invention, since the experienced perfumer may also achieve effects with even lower concentrations or may create novel accords with even higher amounts.
- a further aspect of the present invention refers to a method of improving, enhancing or modifying a flavoured or fragranced product comprising the step of adding thereto an olfactory acceptable amount of a compound of formula (I).
- the compounds of formula (I) may be synthesised from commonly-available starting materials by acidic catalyst esterification of carboxylic acids or acid chlorides according to synthetic protocols known in the art.
- acidic catalyst are para-toluene sulfonic acid monohydrate, tartaric acid and H 2 SO 4 .
- Optically pure compounds of formula (I) and stereoisomer mixtures of a compound of formula (I) enriched in one stereoisomer may be synthesised by starting from optically pure alcohol, e.g. S-(-)-2- methylbutanol, or an stereoisomer mixture enriched in one stereoisomer alcohol respectively.
- Example 2 8ppm 2-Methylbutyl 3-methylbutenoate was added to a beverage base (a) of Example 2 containing 0.20% by weight of the fruit flavour (c). Comparing the resulting composition with the aroma note of the starting beverage, seediness, fattiness and red fruit character was increased, and almost gave a raspberry note to the strawberry profile.
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)
- Seasonings (AREA)
- General Preparation And Processing Of Foods (AREA)
- Cosmetics (AREA)
Abstract
Alkyl-2-enoic acid esters of formula (I) wherein R1, R2 and R3 have the same meaning as described in the specification, their manufacture and their use in flavour and fragrance compositions.
Description
Improvements in or related to organic compounds
This invention refers to new alkyl-2-enoic acid esters, their manufacture and their use in flavour and fragrance compositions.
The flavour and fragrance industry is always interested in new compounds that may enhance, improve, or modify the aroma or flavour in foodstuffs and consumable materials.
Surprisingly, we found certain alkyl-2-enoic acid ester compounds enhance, improve, or modify flavour notes, in particular fruity notes, e.g. blackberry and strawberry notes.
Accordingly, the present invention refers in one of its aspects to a flavour or fragrance composition comprising a compound of formula (I)
wherein R1 is C , C5, or C6 linear or branched alkyl, e.g. n-butyl, sec-butyl, terf-butyl, n- pentyl, 3-methyl-butyl, 2-methyl-butyl, 1 -methyl-butyl, 1-ethyl-propyl,1 ,2-dimethyl-propyl, 2-ethylbutyl; and R2 and R3 are independently hydrogen, methyl or ethyl, with the proviso that a maximum of one of R2 and R3 is hydrogen; with the proviso that if R2 is hydrogen and R3 is methyl, R1 is not butyl or 1 ,3- dimethylbutyl.
Particularly preferred compounds for use in compositions according to the invention are butyl 3-ethylbutenoate, isobutyl 3-ethylbutenoate, pentyl 3-ethylbutenoate, 3- methylbutyl 3-methylpentenoate, 2-methylbutyl pentenoate, 2-methylbutyl 3- methylbuteonate, 2-methylbutyl 3-methylpentenoate, 2-methylbutyl 3-ethylpentenoate, 1 -methyl butyl butenoate, 1-methylbutyl 3-methylpentenoate, 1 -ethylpropyl 3- methyl butenoate and 1 -ethylpropyl 3-methylpentenoate.
Most preferred is 2-methylbutyl 3-methylbutenoate.
Whereas some compounds of the formula (I) have been described in the literature, others have not, and are novel. Thus, the invention provides in another aspect of the invention a compound of formula (I) selected from the group of:
chemical name R1 R2 R3 butyl 3-ethylbutenoate butyl ethyl methyl butyl 3-ethylpentenoate butyl ethyl ethyl isobutyl 3-ethylbutenoate isobutyl ethyl methyl isobutyl 3-ethylpentenoate isobutyl ethyl ethyl sec-butyl 3-ethylpentenoate sec-butyl ethyl ethyl pentyl pentenoate pentyl ethyl hydrogen pentyl 3-ethylbutenoate pentyl ethyl methyl pentyl 3-ethylpentenoate pentyl ethyl ethyl
3-methylbutyl pentenoate 3-methylbutyl ethyl hydrogen
3-methylbutyl 3-methylpentenoate 3-methylbutyl ethyl methyl
3-methylbutyl 3-ethylpentenoate 3-methylbutyl ethyl ethyl
2-methylbutyl pentenoate 2-methylbutyl ethyl hydrogen
2-methylbutyl 3-methylbuteonate 2-methylbutyl methyl methyl
2-methylbutyl 3-methylpentenoate 2-methylbutyl ethyl methyl
2-methylbutyl 3-ethylpentenoate 2-methylbutyl ethyl ethyl
1-methylbutyl butenoate 1-methylbutyl methyl hydrogen
1-methylbutyl pentenoate 1-methylbutyl ethyl hydrogen
1-methylbutyl 3-methylpentenoate 1-methylbutyl ethyl methyl
1-methylbutyl 3-ethylpentenoate 1-methylbutyl ethyl ethyl
1 -ethylpropyl butenoate 1 -ethylpropyl methyl hydrogen
1 -ethylpropyl pentenoate 1 -ethylpropyl ethyl hydrogen
1 -ethylpropyl 3-methylbutenoate 1 -ethylpropyl methyl methyl
1 -ethylpropyl 3-methylpentenoate 1 -ethylpropyl ethyl methyl
1 -ethylpropyl 3-ethylpentenoate 1 -ethylpropyl ethyl ethyl
The compounds of formula (I) may comprise 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 methods known in the art, e.g. preparative HPLC and GC or by stereoselective syntheses.
In one embodiment, the compounds of formula (I) may be used in flavoured products and are useful in modifying, for example, fruity flavours. They may also be used in aromatic, herbal and spicy flavouring. Flavoured products for which the compounds of formula (I) are suitable are food and beverages such as breakfast cereals, alcoholic and non-alcoholic beverages, chewing gum, confections and frostings, fruit juices, frozen dairy desserts and mixes, fruit and water ices, gelatins, puddings, hard candy and cough drops, jams and jellies, commercial milk (whole and skim), milk products, processed fruits and fruit juices, soft candy, sweet sauces, toppings and syrups. This list of products is given by way of illustration and is not to be regarded as being in any way limiting.
The compounds of the present invention may be used in flavoured products alone or in combination with other flavour ingredients known to the person skilled in the art.
In another embodiment, the compounds of formula (I) may be used in fragrance applications, e.g. in any field of fine and functionary perfumery, such as perfumes, household products, laundry products, body care products and cosmetics.
In flavour applications, the compounds of the formula (I) may be present in consumables, e.g. a food, a beverage or a consumer healthcare product, in amounts ranging from 0.5 to 100ppm, more preferably from 1 to 50ppm.
When used in fragrance applications, compounds of the formula (I) can be employed in wide-ranging amounts depending upon the specific application, for example, from about 0.001 to about 10 weight percent. One application may be a fabric softener comprising about 0.001 to 0.05 weight percent of the compound. Another application may be a perfume, i.e. an alcoholic solution, comprising about 0.1 to 10 weight percent of the compound. The preferred concentrations vary between about 0.1 and 5 weight percent. However, these values should not be regarded as limiting on the present invention, since the experienced perfumer may also achieve effects with even lower concentrations or may create novel accords with even higher amounts.
Accordingly, a further aspect of the present invention refers to a method of improving, enhancing or modifying a flavoured or fragranced product comprising the step of adding thereto an olfactory acceptable amount of a compound of formula (I).
The compounds of formula (I) may be synthesised from commonly-available starting materials by acidic catalyst esterification of carboxylic acids or acid chlorides according to synthetic protocols known in the art. Examples of acidic catalyst are para-toluene sulfonic acid monohydrate, tartaric acid and H2SO4. Optically pure compounds of formula (I) and stereoisomer mixtures of a compound of formula (I) enriched in one stereoisomer may be synthesised by starting from optically pure alcohol, e.g. S-(-)-2- methylbutanol, or an stereoisomer mixture enriched in one stereoisomer alcohol respectively.
There now follows a series of non-limiting examples that illustrate the invention.
Example 1 : 2-Methylbutyl 3-methylbutenoate
At room temperature under nitrogen in a 500ml flask, a mixture of 87.3g of 3,3- dimethylacrylic acid (0.85mol) and 134.7g of DL-2-methyl-1-butanol (1.50 mol, 1.75 eq.) and 4.25g of para-toluene suflonic acid monohydrate (0.024mol, 0.026 eq.) was treated with 100ml heptane and then heated at reflux at 90°C for 14 hours while 15.4ml (0.85mol) of H2O was collected in a Dean-Stark trap. The result was an orange solution. The solution was extracted with MTBE / brine (2 x 350 ml / 200 ml brine). The organic layers were washed with NaHCO3 (200 ml saturated solution), brine (200 ml), dried over MgSO4 and concentrated. 205 g of a orange liquid was recovered, which was purified by distillation over a 30cm plate-column. 131.1g of a colorless liquid was recovered (bp 58°C 13.5 torr (4.7bar) 90.5% yield).
1H NMR: 5.69 (s, 1H), 3.93 (dq, 2H), 2.17 (s, 3H), 1.89 (s, 3H), 1.74 (m, 1 H), 1.44 (m, 1 H), 1.20 (m, 1 H), 0.91 (m, 6H). 13C NMR: 116, 68, 34, 27, 26, 20, 16, 11. MS:170 (M+), 100, 83, 70, 55, 43.
Taste description (4ppm in water): fleshy, metallic, skinny, floral, complex, powdery, fatty.
Odour description: blackberry, peely, light tobacco with metallic aspects
Example 2: Beverage with blackberry flavour
4ppm 2-Methylbutyl 3-methyl butenoate was added to a beverage base (a) containing 0.15% by weight of the fruit flavour (b). Comparing the resulting composition with the aroma note of the starting beverage, the green, seedy and ionone notes were enhanced. The overall impression showed a nice complexing effect. By "complexing effect" is meant that the flavour profile is less simplistic, it rounds up the flavour profile.
(a) Beverage base weight % sugar 10.00 citric acid 0.15 water 89.85
(b) Composition of a blackberry flavour parts by weight 1/1000 water (deionized), 533.2000 propylene glycol 225.0000 ethyl alcohol 190 PR grain 225.0000 blackberry essence 10Ox 10.0000 ethyl butyrate 2.2000 ethyl pyruvate 1.1502 maltol 1.0000 raspberry ketone 0.5000
2-heptanol 0.4000 hexanol 0.2160
2-methyl butyric acid 0.2133 cis-3-hexenyl acetate 0.1944 acetaldehyde diethyl acetal 0.1485 methyl amyl ketone 0.1350
4-terpinenol 0.1134 alpha-terpineol crude 0.1080 ethyl isovalerate 0.0999
ethyl caproate 0.0999 furaneol 0.0918 menthol 0.0405 hexyl acetate 0.0378 trans-2-hexenal 0.0216 ionone 0.0108 dimethyl sulfide 0.0081 menthyl acetate 0.0054 benzyl acetate 0.0027 ambrette seed absolute 0.0027 total 1000.0000
Example 3: Beverage with strawberry flavour
8ppm 2-Methylbutyl 3-methylbutenoate was added to a beverage base (a) of Example 2 containing 0.20% by weight of the fruit flavour (c). Comparing the resulting composition with the aroma note of the starting beverage, seediness, fattiness and red fruit character was increased, and almost gave a raspberry note to the strawberry profile.
(c) Composition of a strawberry flavour parts by weight 1 /1000
2-methylbutyl isovalerate 5.00 ethyl butyrate 19.00 ethyl isovalerate 2.00 cis-3-hexenol 15.00 furaneol 20% in propylene glycol 100.00 ethyl caproate 0.23 methyl-2-methyl butyrate 0.22 benzaldehyde 0.40 delta-dodecalactone 0.30 gamma-decalactone 0.70 diacetyl, 10% in triacetin 0.17 acetic acid 0.03 butyric acid 0.08 propylene glycol 856.87 total 1000.00
Claims
1. A flavour or fragrance composition comprising a compound of formula (I)
wherein R1 is C4 to C6 linear or branched alkyl; and
R2 and R3 are independently hydrogen, methyl or ethyl, with the proviso that a maximum of one of R2 and R3 is hydrogen; with the proviso that if R2 is hydrogen and R3 is methyl, R1 is not butyl or 1 ,3- dimethylbutyl.
2. A flavour of fragrance composition according to claim 1 comprising a compound of formula (I) selected from butyl 3-ethylbutenoate, isobutyl 3-ethylbutenoate, pentyl 3- ethylbutenoate, 3-methylbutyl 3-methylpentenoate, 2-methylbutyl pentenoate, 2- methylbutyl 3-methylbuteonate, 2-methylbutyl 3-methylpentenoate, 2-methylbutyl 3- ethylpentenoate, 1-methylbutyl butenoate, 1-methylbutyl 3-methylpentenoate, 1 - ethylpropyl 3-methylbutenoate and 1 -ethylpropyl 3-methylpentenoate.
3. A flavoured product comprising a compound of formula (I) as defined in claim 1 or claim 2.
4. A flavoured product according to claim 3 comprising a compound of formula (I) in an amount ranging from O.δppm to 100ppm.
5. A flavoured product according to claim 3 or claim 4 selected from a food, a beverage, pharmaceutical, oral hygiene product or healthcare product.
6. A fragranced product comprising a compound of formula (I) as defined in claim 1 or claim 2.
7. A fragranced product according to claim 6 wherein the fragranced product is a fine fragrance or perfumed product selected from a cosmetic, or a consumer healthcare or household product.
8. A method of improving, enhancing or modifying a flavoured or fragranced product comprising the step of adding thereto an olfactory acceptable amount of a compound of formula (I) as defined in claim 1 or claim 2.
9. A compound of formula (I)
wherein the groups R )1 , D R2 a „,n-,d J D R3 are selected according to the following table:
R1 R2 R3 butyl ethyl methyl butyl ethyl ethyl isobutyl ethyl methyl isobutyl ethyl ethyl sec-butyl ethyl ethyl pentyl ethyl hydrogen pentyl ethyl methyl pentyl ethyl ethyl
3-methylbutyl ethyl hydrogen
3-methylbutyl ethyl methyl
3-methylbutyl ethyl ethyl
2-methylbutyl ethyl hydrogen
2-methylbutyl methyl methyl
2-methylbutyl ethyl methyl
2-methylbutyl ethyl ethyl
1-methylbutyl methyl hydrogen
1-methylbutyl ethyl hydrogen
1-methylbutyl ethyl methyl
1-methylbutyl ethyl ethyl
1 -ethylpropyl methyl hydrogen
1 -ethylpropyl ethyl hydrogen
1 -ethylpropyl methyl methyl
1 -ethylpropyl ethyl methyl
1 -ethylpropyl ethyl ethyl
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/559,194 US7632964B2 (en) | 2003-06-07 | 2004-06-02 | Organic compounds |
| CN2004800158768A CN1802342B (en) | 2003-06-07 | 2004-06-02 | Improvements in or related to organic compounds |
| EP04735715A EP1633693A1 (en) | 2003-06-07 | 2004-06-02 | Improvements in or related to organic compounds |
| BRPI0411087-0A BRPI0411087A (en) | 2003-06-07 | 2004-06-02 | improvements in or related to organic compounds |
| JP2006515618A JP2006527285A (en) | 2003-06-07 | 2004-06-02 | Improvements in or related to organic compounds |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0313173.7 | 2003-06-07 | ||
| GBGB0313173.7A GB0313173D0 (en) | 2003-06-07 | 2003-06-07 | Improvements in or related to organic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2004108653A1 true WO2004108653A1 (en) | 2004-12-16 |
Family
ID=27589667
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/CH2004/000331 WO2004108653A1 (en) | 2003-06-07 | 2004-06-02 | Improvements in or related to organic compounds |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7632964B2 (en) |
| EP (1) | EP1633693A1 (en) |
| JP (1) | JP2006527285A (en) |
| CN (1) | CN1802342B (en) |
| BR (1) | BRPI0411087A (en) |
| GB (1) | GB0313173D0 (en) |
| WO (1) | WO2004108653A1 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010037244A2 (en) * | 2008-10-01 | 2010-04-08 | Givaudan Sa | Organic compounds |
| EP2769972A1 (en) * | 2013-02-25 | 2014-08-27 | International Flavors & Fragrances Inc. | Novel organoleptic compound |
| EP2769971A1 (en) * | 2013-02-25 | 2014-08-27 | International Flavors & Fragrances Inc. | Novel Organoleptic Compound |
| WO2024100254A1 (en) * | 2022-11-11 | 2024-05-16 | Basf Se | Dimethyl acrylic acid-based compounds as aroma ingredients |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010513657A (en) * | 2006-12-20 | 2010-04-30 | ジボダン ネーデルランド サービシーズ ビー．ヴイ． | N-substituted-p-menthane-3-carboxamides and uses thereof |
| WO2008141469A2 (en) * | 2007-05-23 | 2008-11-27 | Givaudan Sa | Butone derivatives useful as cooling agents |
| WO2009076792A1 (en) * | 2007-12-19 | 2009-06-25 | Givaudan Sa | Cooling compounds |
| US20100297038A1 (en) * | 2008-01-17 | 2010-11-25 | Givaudan S.A. | Benzimidazole Derivatives And Their Use As Cooling Agents |
| JP5642976B2 (en) * | 2010-02-08 | 2014-12-17 | サントリー食品インターナショナル株式会社 | Coffee aroma-containing composition |
| CN104293530B (en) * | 2014-10-14 | 2019-08-13 | 周慧燕 | A kind of plant cleaning combination |
| GB201707639D0 (en) * | 2017-05-12 | 2017-06-28 | Givaudan Sa | Improvements in or relating to organic compounds |
| CN112410121A (en) * | 2020-11-17 | 2021-02-26 | 广东馨杰生化科技有限公司 | Blackberry essence and preparation method and application thereof |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2164188A (en) | 1934-05-16 | 1939-06-27 | Shell Dev | Esterification of allyl type alcohols and products resulting therefrom |
| US2500005A (en) | 1946-08-17 | 1950-03-07 | Sinclair Refining Co | Production of esters of unsaturated lower fatty acids |
| DE2017208A1 (en) | 1970-04-10 | 1971-10-21 | Haarmann & Reimer GmbH, 3450 Holz minden | 4-methyl pentanoI-2-crotonate |
| US4657862A (en) * | 1984-07-31 | 1987-04-14 | International Flavors & Fragrances Inc. | Preparation of naturally-occurring C2-C5 alkyl esters of C4-C5 carboxylic acids by means of fermentation of C5-C6 amino acids in the presence of C2-C5 alcohols |
| AU1707497A (en) * | 1996-01-23 | 1997-08-20 | Rigel Pharmaceuticals, Inc. | Methods for screening for transdominant intracellular effector peptides and rna molecules |
| SG93823A1 (en) * | 1998-02-13 | 2003-01-21 | Givaudan Roure Int | Aryl-acrylic acid esters |
| EP1072673A3 (en) * | 1999-07-20 | 2001-03-21 | The Procter & Gamble Company | Perfume compositions |
| DE10212687A1 (en) * | 2001-03-23 | 2002-09-26 | Haarmann & Reimer Gmbh | Composition for thermal release of perfumes, useful for personalized perfuming of e.g. films, comprises mixture of compounds that retain original odor after release |
-
2003
- 2003-06-07 GB GBGB0313173.7A patent/GB0313173D0/en not_active Ceased
-
2004
- 2004-06-02 JP JP2006515618A patent/JP2006527285A/en active Pending
- 2004-06-02 BR BRPI0411087-0A patent/BRPI0411087A/en not_active IP Right Cessation
- 2004-06-02 WO PCT/CH2004/000331 patent/WO2004108653A1/en active Application Filing
- 2004-06-02 CN CN2004800158768A patent/CN1802342B/en not_active Expired - Fee Related
- 2004-06-02 EP EP04735715A patent/EP1633693A1/en not_active Withdrawn
- 2004-06-02 US US10/559,194 patent/US7632964B2/en not_active Expired - Fee Related
Non-Patent Citations (10)
| Title |
|---|
| DATABASE BEILSTEIN BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; XP001183870, Database accession no. BRN3536185 * |
| DATABASE BEILSTEIN BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; XP002302164, Database accession no. BRN1703650 * |
| DATABASE BEILSTEIN BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; XP002302707, Database accession no. BRN3081010 * |
| DATABASE BEILSTEIN BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; XP002302720, Database accession no. BRN3081011 * |
| DECAUX ET AL, C.R.SEANCES ACAD.SCI.SER. D,267, 1968, pages 738 * |
| DECAUX ET AL, C.R.SEANCES ACAD.SCI.SER.D,267, 1968, pages 738 * |
| ENDERS,D. ET AL., SYNTHESIS, 1991, pages 649 - 654 * |
| ROGOFF W M ET AL: "SYNTHETIC ATTRACTANTS SCREENED IN THE FIELD AS LURES FOR CHLOROPIDAE", ANNALS OF THE ENTOMOLOGICAL SOCIETY OF AMERICA, ENTOMOLOGICAL SOCIETY OF AMERICA, COLLEGE PARK, MD, US, vol. 66, no. 2, 1973, pages 262 - 265, XP009037749, ISSN: 0013-8746 * |
| SCHJAENBERG ET AL, CHEM.BER. 70, 1937, pages 2387 * |
| STURM WOLFGANG: "Die gezielte Riechstoffsynthese- Geruchliche Verwandtschaft der Isobtutenyl- und Phenylgruppe", PARÜMERIE UND KOSMETIK, vol. 55, no. 12, 1974, pages 351 - 355, XP009037748 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010037244A2 (en) * | 2008-10-01 | 2010-04-08 | Givaudan Sa | Organic compounds |
| WO2010037244A3 (en) * | 2008-10-01 | 2010-07-15 | Givaudan Sa | Organic compounds suitable for modulating fragrance compositions |
| EP2769972A1 (en) * | 2013-02-25 | 2014-08-27 | International Flavors & Fragrances Inc. | Novel organoleptic compound |
| EP2769971A1 (en) * | 2013-02-25 | 2014-08-27 | International Flavors & Fragrances Inc. | Novel Organoleptic Compound |
| WO2024100254A1 (en) * | 2022-11-11 | 2024-05-16 | Basf Se | Dimethyl acrylic acid-based compounds as aroma ingredients |
Also Published As
| Publication number | Publication date |
|---|---|
| GB0313173D0 (en) | 2003-07-16 |
| CN1802342B (en) | 2010-05-26 |
| JP2006527285A (en) | 2006-11-30 |
| BRPI0411087A (en) | 2006-07-25 |
| EP1633693A1 (en) | 2006-03-15 |
| US7632964B2 (en) | 2009-12-15 |
| CN1802342A (en) | 2006-07-12 |
| US20060142177A1 (en) | 2006-06-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU667556B2 (en) | Agents having a physiological cooling effect and active compounds which are suitable for these agents | |
| US7632964B2 (en) | Organic compounds | |
| EP1927593A1 (en) | Pyran derivates, process of preparation and use thereof in perfumery and flavouring | |
| JP3001944B2 (en) | Acyclic terpene compound containing oxygen or sulfur, fragrance composition and flavor composition containing the same | |
| WO2019216412A1 (en) | Dienal compound and perfume composition | |
| EP2125767B1 (en) | Pyran derivatives, process of preparation and use thereof in perfumery and flavouring | |
| EP0482385B1 (en) | (2E,4Z,7Z)-ethyl decatrienoate and its use as a perfuming and flavouring ingredient | |
| JP4393824B2 (en) | Fragrance composition | |
| US7105194B2 (en) | Organoleptic compositions: use of 3-mercapto alkanoic acid esters as flavor ingredients | |
| US7008919B2 (en) | Use of thio derivatives as perfuming and flavoring ingredients | |
| US6034268A (en) | 8-Ocimenyl esters and fragrances and flavors containing the same | |
| US3988487A (en) | Foodstuff flavoring compositions comprising alkylidene alkenals and processes for preparing same as well as flavoring compositions for use in such foodstuff | |
| EP1153547B1 (en) | Organoleptic compositions | |
| EP1263299B1 (en) | Use of 2,4,7-decatrienal as perfuming or flavouring ingredient | |
| JP6639436B2 (en) | 3-Methyl-4-dodesenic acid and method for producing the same | |
| US3970701A (en) | Lower alkenals | |
| US20070264340A1 (en) | Aromachemicals | |
| US4547315A (en) | Alkyl alpha-campholenates and dihydro derivatives thereof as odorants and flavorants | |
| JP6374547B2 (en) | Refreshing agent with reduced miscellaneous taste | |
| US6720302B2 (en) | Method for preparing a γ-unsaturated β-lactone and use thereof as an aromatic and flavouring ingredient | |
| US7141686B2 (en) | E2, E4, Z8-undecatrienoic acid and ester and carboxamide derivatives thereof, organoleptic uses thereof and processes for preparing same | |
| CA1058442A (en) | Flavoring and fragrance compositions and products | |
| JP2020514424A (en) | Fragrance and flavor ingredients | |
| US7875737B2 (en) | Pyran derivatives, process of preparation and use thereof in perfumery and flavouring | |
| US4590953A (en) | Alkyl α-campholenates and dihydro derivatives thereof as tobacco flavorants |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AK | Designated states |
Kind code of ref document: A1 Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NA NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW |
|
| AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): GM KE LS MW MZ NA SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LU MC NL PL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG |
|
| 121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
| WWE | Wipo information: entry into national phase |
Ref document number: 2004735715 Country of ref document: EP |
|
| ENP | Entry into the national phase |
Ref document number: 2006142177 Country of ref document: US Kind code of ref document: A1 |
|
| WWE | Wipo information: entry into national phase |
Ref document number: 10559194 Country of ref document: US |
|
| WWE | Wipo information: entry into national phase |
Ref document number: 3303/CHENP/2005 Country of ref document: IN Ref document number: 20048158768 Country of ref document: CN Ref document number: 2006515618 Country of ref document: JP |
|
| WWP | Wipo information: published in national office |
Ref document number: 2004735715 Country of ref document: EP |
|
| WWP | Wipo information: published in national office |
Ref document number: 10559194 Country of ref document: US |
|
| ENP | Entry into the national phase |
Ref document number: PI0411087 Country of ref document: BR |