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WO2004016105A1 - Composes organiques ameliores - Google Patents

Composes organiques ameliores Download PDF

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Publication number
WO2004016105A1
WO2004016105A1 PCT/CH2003/000554 CH0300554W WO2004016105A1 WO 2004016105 A1 WO2004016105 A1 WO 2004016105A1 CH 0300554 W CH0300554 W CH 0300554W WO 2004016105 A1 WO2004016105 A1 WO 2004016105A1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
compound
food product
flavour
citral
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.)
Ceased
Application number
PCT/CH2003/000554
Other languages
English (en)
Inventor
Andrew Daniher
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Givaudan SA
Original Assignee
Givaudan SA
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Givaudan SA filed Critical Givaudan SA
Priority to AU2003250713A priority Critical patent/AU2003250713A1/en
Publication of WO2004016105A1 publication Critical patent/WO2004016105A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
    • C07C47/14—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing halogen
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
    • A23L2/52—Adding ingredients
    • A23L2/56—Flavouring or bittering agents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/202—Aliphatic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/29—Fruit flavours

Definitions

  • the invention relates to flavour or fragrance compositions containing 6-fluoro-alkenes, in particular substituted 6-fluoro-2,6-heptadienals and to methods of flavouring or of adding fragrance to a food, beverage or a consumer product or household product using these compounds.
  • flavour and fragrance industry is continuously interested in new ingredients that may impart to . a product a green, lemony and citral-like character.
  • citral a mixture of neral and geranial
  • citral a mixture of neral and geranial
  • citral is an important ingredient in the flavour industry and has found use in flavour compositions to impart citrus notes.
  • the use of citral in the flavour industry is limited to products that do not have a low pH value, because of its instability under such conditions whereupon it degrades into aromatic ring systems, e.g. p-cresol, p-cymene and p-methylaceto-phenone, described for example by Schieberle et al. (Lebensm.- Wiss. u- Technol., 21 , 158-162, 1988).
  • These degradation products are responsible for undesirable off-notes in food products that lead to the reduction of the flavour quality.
  • substituted 6-fluoro-2,6-heptadienals are very stable under acidic conditions, e.g. under conditions wherein the pH value is below 7, in particular below 4, particularly below 3.
  • these compounds show similar organoleptic properties as citral.
  • flavour or fragrance composition comprising a compound of formula I
  • R , R and R are independently hydrogen, methyl, or ethyl.
  • compounds of formula I may find use in particular in acidic flavour and fragrance applications to achieve a constant flavour quality over a long period of time, e.g. up to 10 days, more preferably up to 100 days, without degrading into undesirable off-notes.
  • the compounds of formula I may contain one or more prochiral centres and as such may exist as a mixture of cis-trans-isomers, 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 desired to prepare individual stereoisomers, this may be achieved according to methodology known in the art, e.g. column chromatography.
  • the present invention refers to food products comprising a compound of formula I.
  • food products comprising a compound of formula I.
  • acidic food products such as beverages, e.g. carbonated soft drinks and juice drinks, such as lemon juice, orange juice or lime juice.
  • a compound of formula I may be present in amounts ranging from 0.001 to 100 ppm, more preferably from 0.01 to 10 ppm, most preferred 0.1 to 7 ppm.
  • a compound of formula I or a mixture thereof may be added to a food product alone or by adding a flavour or fragrance composition comprising a compound of formula I to a food product.
  • the compounds of formula I are particularly well suited in flavour or fragrance compositions where enhancement of citrus notes are required, such as lemon, orange and lime compositions.
  • the present invention refers to fragrance applications, e.g. any field of fine and functional perfumery, such as perfumes, household products, laundry products, body care products and cosmetics, comprising a compound of formula I or in combination with other known odourant molecules selected from the extensive range of natural and synthetic molecules currently available, such as essential oil, alcohols, aldehydes and ketones, ether and acetals, ester and lacatones, macrocycles and heterocycles, and/or admixtures 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.
  • odourant molecules selected from the extensive range of natural and synthetic molecules currently available, such as essential oil, alcohols, aldehydes and ketones, ether and acetals, ester and lacatones, macrocycles and heterocycles, and/or admixtures with one or more ingredients or excipients conventionally used in conjunction with odourants
  • fragrance applications compounds of the present invention may be present in amounts ranging from 0.001 to 20 weight percent depending upon the specific application and on the nature and quantity of other odourant ingredients.
  • 6-fluoro-2,6-heptadienals may be synthesised starting from an appropriate fluorinated ester by Claisen rearrangement followed by Cope rearrangement, as described for example by F. Camps et al., Tetrahedron Vol. 44, No. 16, pp. 5161 - 5167, 1988.
  • the resulting fluorinated acid may then be reduced to the corresponding fluorinated alcohol in the presence of LiAIH 4 , which may further converted to the corresponding fluorinated aldehyde in the presence of Mn0 2l as described for example by C. Arbones et al., Heterocycles, Vol. 31 , No. 1 , pp 67 - 78, 1990.
  • 6-fluoro-3,7-dimethyl-2,6-octadienal (6-F-citral) is tested in direct comparison to citral.
  • 200 ppm solutions of 6-F-citral and citral in an acid (pH 2.8) beverage base is made.
  • the solutions is stored at room temperature in the dark for 111 days.
  • Time points are analyzed by Fast-GC using an internal standard to quantify the amounts of each compound.
  • all of the citral is degraded.
  • no degradation of 6-F-citral is detected.
  • 6-F-citral is just about 100 % intact, accordingly no degradation of 6-F-citral occurs.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Fats And Perfumes (AREA)

Abstract

Compositions aromatiques comprenant un composé représenté par la formule (1) et procédé d'aromatisation d'un produit alimentaire, d'une boisson, d'un produit de consommation ou de ménage au moyen de ce composé. R1, R2 et R3 représentent indépendamment hydrogène, méthyle ou éthyle.
PCT/CH2003/000554 2002-08-19 2003-08-15 Composes organiques ameliores Ceased WO2004016105A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2003250713A AU2003250713A1 (en) 2002-08-19 2003-08-15 Improvements in or related to organic compounds

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0219212.8 2002-08-19
GBGB0219212.8A GB0219212D0 (en) 2002-08-19 2002-08-19 Improvements in or relating to organic compounds

Publications (1)

Publication Number Publication Date
WO2004016105A1 true WO2004016105A1 (fr) 2004-02-26

Family

ID=9942514

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CH2003/000554 Ceased WO2004016105A1 (fr) 2002-08-19 2003-08-15 Composes organiques ameliores

Country Status (3)

Country Link
AU (1) AU2003250713A1 (fr)
GB (1) GB0219212D0 (fr)
WO (1) WO2004016105A1 (fr)

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3654309A (en) * 1967-05-26 1972-04-04 Firmenich & Cie Process for the preparation of unsaturated aldehydes
DE2143991A1 (de) * 1971-09-02 1973-03-08 Basf Ag 2,6-dimethyl-2,6-undecadien-10-on-1al und seine acetale
US3928402A (en) * 1970-12-22 1975-12-23 Firmenich & Cie Ethyl 2-trans,4-cis-undecadienoate
US3997577A (en) * 1974-07-05 1976-12-14 Basf Aktiengesellschaft Manufacture of lavandulol and its esters
GB1469135A (en) * 1973-07-30 1977-03-30 Int Flavors & Fragrances Inc Alkenals and process for producing alkenals
US4073811A (en) * 1973-03-12 1978-02-14 Hoffmann-La Roche Inc. Process for the preparation of aldehydes
US6034268A (en) * 1997-11-05 2000-03-07 Haarmann & Reimer Gmbh 8-Ocimenyl esters and fragrances and flavors containing the same

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3654309A (en) * 1967-05-26 1972-04-04 Firmenich & Cie Process for the preparation of unsaturated aldehydes
US3928402A (en) * 1970-12-22 1975-12-23 Firmenich & Cie Ethyl 2-trans,4-cis-undecadienoate
DE2143991A1 (de) * 1971-09-02 1973-03-08 Basf Ag 2,6-dimethyl-2,6-undecadien-10-on-1al und seine acetale
US4073811A (en) * 1973-03-12 1978-02-14 Hoffmann-La Roche Inc. Process for the preparation of aldehydes
GB1469135A (en) * 1973-07-30 1977-03-30 Int Flavors & Fragrances Inc Alkenals and process for producing alkenals
US3997577A (en) * 1974-07-05 1976-12-14 Basf Aktiengesellschaft Manufacture of lavandulol and its esters
US6034268A (en) * 1997-11-05 2000-03-07 Haarmann & Reimer Gmbh 8-Ocimenyl esters and fragrances and flavors containing the same

Also Published As

Publication number Publication date
AU2003250713A1 (en) 2004-03-03
GB0219212D0 (en) 2002-09-25

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