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.

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• 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)
• Seasonings (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• General Preparation And Processing Of Foods (AREA)
• Cosmetics (AREA)

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• 2003
  • 2003-06-07 GB GBGB0313173.7A patent/GB0313173D0/en not_active Ceased
• 2004
  • 2004-06-02 EP EP04735715A patent/EP1633693A1/en not_active Withdrawn
  • 2004-06-02 JP JP2006515618A patent/JP2006527285A/ja active Pending
  • 2004-06-02 CN CN2004800158768A patent/CN1802342B/zh not_active Expired - Fee Related
  • 2004-06-02 BR BRPI0411087-0A patent/BRPI0411087A/pt not_active IP Right Cessation
  • 2004-06-02 WO PCT/CH2004/000331 patent/WO2004108653A1/en not_active Ceased
  • 2004-06-02 US US10/559,194 patent/US7632964B2/en not_active Expired - Fee Related

Non-Patent Citations (10)

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