Food or edible material: processes – compositions – and products – Products per se – or processes of preparing or treating... – Flavor per se – or containing flavor or flavor improver of...
Reexamination Certificate
2000-04-25
2001-11-27
Reamer, James H. (Department: 1614)
Food or edible material: processes, compositions, and products
Products per se, or processes of preparing or treating...
Flavor per se, or containing flavor or flavor improver of...
C426S003000, C424S049000, C424S054000, C560S205000, C560S261000
Reexamination Certificate
active
06322838
ABSTRACT:
FIELD OF THE INVENTION
The invention relates to mint and/or fruit flavor compositions which comprise 8-ocimenyl esters and to their use in foods, tobacco products or for oral hygiene.
BACKGROUND OF THE INVENTION
In the fragrance and flavor industry, there is a great need for substances, which can be used in fragrance and flavor compositions to partially or completely replace natural substances, which, because of the laborious nature of their manufacture, are expensive. Additionally, such natural substances are available only in limited amounts and, moreover, their properties are subject to considerable quality fluctuations, which arise because they are natural substances.
Of particular interest, then, are substances, which not only have excellent organoleptic properties (i.e., properties perceptible only by the senses), but, because of their strength and richness, can be used to achieve notable effects even at extremely low concentrations.
However, in the flavorings and food industry, substances which, apart from the property of imparting a certain odor or taste, have additional properties which are increasingly important. These can, for example, be certain stimuli, which are transmitted over the trigeminal nerve and thus perceived. They can, however, also be effects, which reduce or enhance olfactory and gustatory sensations.
SUMMARY OF THE INVENTION
We have found mint and/or fruit flavor compositions, which comprise 8-ocimenyl esters of the formula
wherein
one of the two radicals R
1
and R
2
is methyl and the other is vinyl and
one of the two radicals R
3
and R
4
is methyl and the other is
wherein
R
5
is hydrogen, alkyl or alkenyl, in particular C
1
-C
6
-alkyl or C
2
-C
6
-alkenyl.
DETAILED DESCRIPTION OF THE INVENTION
Preference is given to mint and/or fruit flavor compositions, which comprise 8-ocimenyl esters of the formula
wherein
one of the two radicals R
1
and R
2
is methyl and the other is vinyl and
one of the radicals R
3
and R
4
is methyl and the other is
wherein
R
5
is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl or 2-butenyl.
Particular preference is given to mint and/or fruit flavor compositions, which comprise 8-ocimenyl esters of the formula:
in which
R
5
is hydrogen, methyl or ethyl.
Surprisingly, the 8-ocimenyl esters enhance the olfactory and gustatory sensation in mint and/or fruit flavor compositions.
8-Ocimenyl esters for the mint and/or fruit flavor compositions according to the present invention can be prepared by reacting 6-ocimenyl chloride of the formula
wherein
R
1
and R
2
are as defined above,
with a salt, in particular an alkaline salt, such as Na or K salt, of an aliphatic carboxylic acid, in particular a C
2
-C
7
-carboxylic acid.
The process is preferably carried out in an organic solvent, in particular in a dipolaraprotic solvent. Examples of such solvents are dimethylformamide, dimethyl sulphoxide, N-methylpyrrolidone, diethylene glycol dimethyl ether and mixtures thereof. The reaction is preferably carried out at a temperature from 50 to 150° C., more preferably from 90 to 120° C., optionally under pressure.
The process, starting from the compounds of the formula (II), is preferably carried out in the presence of an alkali metal iodide or elemental iodine, more preferably in the presence of NaI, this addition preferably being used in catalytic amounts, preferably in an amount of from 0.01 to 10% by weight, based on II.
In the process, the compound of the formula (II) can be used as the E- or Z-isomer or as any E/Z mixture.
If the E/Z mixture of the formula (II) is used, i.e. a mixture of a compound (II) in which R
1
is methyl and R
2
is vinyl, and a compound (II) in which R
1
is vinyl and R
2
is methyl, then a mixture containing the compounds of the formulae (Ia)-(Id) is obtained.
Particular preference is given to the process using sodium acetate as salt of an aliphatic carboxylic acid.
6-Ocimenyl chlorides can, for example, be prepared by reacting ocimene of the formula
wherein
R
1
and R
2
are as defined above,
with hypochlorous acid or sulfuryl chloride (SO
2
Cl
2
).
For the reactions with hypochlorous acid, the latter is usually generated in situ from salts of hypochlorous acid by acidification. For the preparation of 6-ocimenyl chloride(II), it has proven advantageous to liberate hypochlorous acid from sodium hypochlorite solution by acidification with acetic acid. The reaction with ocimene then proceeds in a two-phase system; the presence of a solvent is not necessary. The reaction temperature can be between 0 and 50° C.; a temperature range from 10 to 20° C. is preferable.
The chlorination is carried out using sulfuryl chloride, preferably in the presence of a base, more preferably in the presence of an alkali metal carbonate, such as sodium or potassium carbonate, which is used, in particular, in excess, based on sulfuryl chloride. Possible solvents are compounds, which are inert towards sulfuryl chloride, such as hydrocarbons, preferably n-hexane or n-heptane, such as halogenated hydrocarbons, preferably dichloromethane or tetrachloromethane, or such as ethers, preferably methyl tert-butyl ether. The reaction temperature is, in particular, from 0 to 50° C., a range from 20 to 30° C. being preferable.
The ocimene can be used here as cis-ocimene, as trans-ocimene or as a cis/trans mixture.
Preference is given to using a cis/trans ocimene mixture, a content of from 50 to 90% by weight of trans-isomer and from 50 to 10% by weight of cis-isomer being preferable, from which a E/Z mixture of the compound of the 6-ocimenyl chlorides (II) can be prepared and therefrom, in turn, a mixture of isomeric 8-ocimenyl esters of the formulae (Ia)-(Id).
Mint Compositions According to the Present Invention Comprise Mint Flavor Components and 8-ocimenyl Esters
Mint flavor components can, for example, be:
essential oils, such as, for example, peppermint oil, spearmint oil, mentha-arvensis oil, clove oil, citrus oils, cinnamon bark oil, wintergreen oil, cassia oil, davana oil, spruce needle oil, eucalyptus oil, fennel oil, galbanum oil, ginger oil, camomile oils, caraway oil, rose oil, geranium oil, sage oils, yarrow oil, anise seed oil, thyme oil, juniper berry oil, angelica root oil, and the fractions of these oils.
Individual flavor substances (in the case of chiral compounds as racemate or as individual enantiomer or as enantiomer-enriched mixture) such as, for example, menthol, menthone, isomenthone, menthyl acetate, menthofuran, mint lactone, eucalyptol, limonene, eugenol, pinene, sabinene hydrate, 3-octanol, carvone, gamma-octalactone, gamma-nonalactone, germacren-D, viridiflorol, 1,3E,5Z-undecatriene, isopulegol, piperitone, 3-octyl acetate, isoamyl isovalerate, hexanol, hexanal, cis-3-hexenol, linalool, alpha-terpineol, cis and trans carvyl acetate, p-cymene, damascenone, damascone, dimethyl sulfide, fenchol, cis-4-heptenal, isobutyraldehyde, isovaleraldehyde, cis-jasmone, anisaldehyde, methyl salicylate, myrtenyl acetate, 2-phenyl ethyl alcohol, 2-phenylethyl isobutyrate, 2-phenylethyl isovalerate, cinnamaldehyde, geraniol, nerol.
Compounds having a physiological cooling effect such as for example menthol, menthoneglycerol acetal, menthyl lactate, substituted menthyl-3-carboxamides (e.g. menthyl-3-carboxylic acid N-ethylamide), 2-isopropyl-N,2,3-trimethylbutanamide, substituted cyclohexanecarboxylic acid amides, 3-menthoxypropane-1,2-diol, 2-hydroxyethylmenthyl carbonate, 2-hydroxypropylmenthyl carbonate, N-acetylglycine menthyl ester, menthylhydroxycarboxylic acid ester (e.g. menthyl-3-hydroxybutyrate), menthylsuccinic acid ester, 2-mercaptocyclodecanone and 2-isopropyl-5-methylcyclohexyl-5-oxo-2-pyrrolidinecarboxylic acid.
Sweeteners, such as for example aspartame, saccharin, Acesulfam-K®, sorbite; xylite, cyclamates (such as for example sodium cyclamate), Sucralose®, Alitam®, Neotam ®, Thaumatin®, Neohesperidine DC®, maltitol and lactitol.
Preferred mint flavor components are:
essential oils such as, for example, peppermint oil, spearmint oil, mentha-arvensis oil
Guntert Matthias
Kindel Gunter
Koppe Volkmar
Lambrecht Stefan
Surburg Horst
Cheung Noland J.
Gil Joseph C.
Haarmann & Reimer GmbH
Reamer James H.
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