Combination of formate esters and pepper-like constituents as an orally-consumable chloroform substitute.

This invention relates to novel compositions comprising a combination of one or more pepper-like constituent(s) and one or more volatile formate ester(s) which are useful as a chloroform substitute in a wide variety of pharmaceutical, oral hygiene and confectionery products. The compositions specifically comprise from 0.01% to 1.0% by weight of pepper-like constituent(s) and from 5.0% to 99.5% by weight of volatile formate ester(s). The pepper-like constituents are preferably selected from piperine, iso-piperine, chavicine, iso-chavicine, capsaiacin, capsicum extract, capsicum oleoresin, zingerone, mustard oil, horseradish extract, hot pepper oil, hot pepper extract and mixtures thereof. The volatile formate esters are preferably C₁-C₄ alkyl formate esters, such as ethyl formate, methyl formate, propyl formate, and isopropyl formate, and they preferably have a boiling point of less than 80°C.

The compositions of this invention are useful in a variety of products such as cough medicines, cold medicines, mouthwashes, toothpastes, lozenges and chewing gums as a replacement for chloroform. The compositions of this invention have essentially all of the taste and mouthfeel characteristics of chloroform and they are relatively non-toxic, non-carcinogenic, non-anesthetic and safer to handle and process. Many pharmaceutical, oral hygiene and food products have incorporated chloroform as a flavoring aid because of its unique flavor characteristics. The flavor characteristics of chloroform can generally be described as a sweet, cooling, fizzy, tingly and slight burning effect. These flavor characteristics of chloroform are especially desirable in orally-administered cough/cold medicines, mouthwashes, mouth sprays, toothpastes, chewing gums and candy breath fresheners.

However, chloroform has been identified as a carcinogen, and it has been banned by the U.S. Food and Drug Administration from use in drug, cosmetic and food products since 1976. There have been considerable efforts over the past 10 years to find a substitute for chloroform for use in food and drug applications. Nevertheless, none of the chloroform substitutes that have been developed over the past decade completely mimics the sensory attributes and flavor characteristics of chloroform.

U.S.-A-4,131,687 describes compositions for enhancing the flavor of consumable materials using at least one C₁₀-terpene alkyl, alkenyl, haloalkenyl, and alkynyl ether and diether. The compositions of the '687 patent are described as being suitable for use with a large number of flavoring adjuvants, such as, inter alia, ethyl formate or piperine. The '687 patent does not disclose flavoring compositions which are useful as a substitute for chloroform.

U.S.-A-4,195,100 describes the use of 2-oxabicycloocatane derivatives to enhance or augment the flavor of food ad medicinal products. These oxabicyclooctane derivatives augment or enhance eucalyptus, herbaceous, blueberry-like, piney, lime-like, clove, banana-like, woody, oriental-like, spicy, black pepper and floral flavor characteristics with stringent, biting and bitter effects. These oxabicyclooctane derivatives are useful with a large variety of flavoring adjuvants, such as ethyl formate or piperine. The '100 patent does not disclose flavoring compositions which are useful as a substitute for chloroform.

U.S.-A-4,198,393 describes the use of cyclic acetals of 2-methyl-2-pentenal in foodstuffs, chewing gums, toothpastes or medicinal products to produce sweet, fruity, goose berry, green, spearmint-like, aniseed, licorice, floral and herbal flavor characteristics. These may also be used with a large variety of flavorants, such as ethyl formate, piperine and many others. The '393 patent does not teach or suggest flavoring compositions which are useful as a replacement for chloroform.

U.S.-A-4,282,205 discloses that certain 2,4,6-trimethylcyclohexenemethanol derivatives are capable of augmenting or enhancing a variety of flavors and fragrances of various consumable materials. A large variety of other flavorants may be included such as ethyl formate, piperine and many others. However, the '205 patent does not disclose or suggest flavoring compositions which are useful as a chloroform substitute.

U.S.-A-4,296,137 discloses that 1-ethoxy-1-ethanol acetate is capable of imparting, augmenting or enhancing a variety of flavors and fragrances to various consumable materials. Other flavorants useful therewith include ethyl formate, piperine and many others. Flavorings as a substitute for chloroform are not disclosed or suggested by the '137 patent.

U.S.-A-4,521,634 relates to ether carbinols which are capable of augmenting or enhancing the aroma and/or taste of consumable materials, including foodstuffs, chewing gums, toothpastes, medicinal products and tobaccos. These ether carbinols are described at col. 66, lines 25-48 as capable of extending the fresh after-taste without having an effect similar to that of chloroform and without the use of chloroform. Thus, the '634 patent does not disclose or teach flavoring compositions which are useful as chloroform substitutes and which has essentially all of the flavoring effects of chloroform.

U.S.-A-4,454,111 discloses that prenyl methyl carbonates are useful in flavoring foodstuffs, chewing gums, toothpastes and medicinal products. Cooling and "chloroform-like" nuances may be provided by the utilization of these prenyl methyl carbonates. Other flavorants may also be used with these prenyl methyl carbonates.

Methyl formate and iso-propyl formate are described by Steffen Arctander, <u style="single">Perfume and Flavor Chemicals</u>, 1969 as being occasionally used in place of chloroform to produce a flavor-burst or warm bite. However, Arctander does not teach the formate esters in combination with pepper-like constituents to obtain essentially all of the taste and sensory characteristics of chloroform.

None of the flavoring compositions known in the prior art provides substitutes for chloroform which exhibit essentially all of the flavor and taste characteristics of chloroform. It is the object of the present invention to provide a flavoring substitute for chloroform which has comparable flavor and taste characteristics as chloroform in essentially every respect. It is a further object of the present invention to provide a flavoring composition which is useful as a substitute for chloroform and which is relatively non-toxic and non-carcinogenic. It is an even further object of this invention to provide novel, orally-consumable compositions comprising a combination of pepper-like constituents and one or more volatile formate ester(s) which exhibit a sweet, cooling, tingly and slightly burning and biting taste.

The present invention involves novel flavoring compositions which are useful as a direct substitute for chloroform in a variety of pharmaceutical, medicinal, oral hygiene and confectionery products. These flavoring compositions exhibit essentially all of the taste, flavor and mouthfeel characteristics of chloroform, and they are relatively non-toxic, non-carcinogenic and non-anesthetic.

The compositions of this invention comprise a combination of one or more pepper-like constituents and one or more volatile formate esters. Specifically the present invention refers to a flavoring composition comprising in combination from 0.01% to 1.0% by weight of one or more pepper-like constituent(s) and from 5.0% to 99.5% by weight of one or more volatile formate ester(s); said composition being suitable as an orally-consumable chloroform substitute. The compositions preferably comprise by weight from 0.01% to 1.0% of pepper-like constituents; more preferably from 0.05% to 0.7%; and most preferably from 0.1% to 0.65%. Further, the compositions preferably comprise by weight from 5% to 99.5% of volatile formate ester(s); more preferably from 10% to 70%; and most preferably from 20% to 50%.

The components in the composition of the present invention always add up to 100% whereby the balance between the pepper-like constituent(s) and the volatile formate ester(s) if required is made up by an excipient. Such an excipient may consist of (a) useful solvent(s), sweetener(s) ,thickeners and/or other ingredients as further defined herein below.

The pepper-like constituents useful according to the present invention are those orally-consumable materials which have pungent and biting taste characteristics similar to that of pepper. The pepper-like constituents are selected from piperine, iso-piperine, chavicine, iso-chavicine, capsaiacin, capsicum extract, capsicum oleoresin, zingerone, mustard oil, horseradish extract, hot pepper oil, hot pepper extract, and mixtures thereof. The most preferred pepper-like constituent for use in this invention is piperine.

Piperine is a known flavorant which has the chemical name 1-[5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl] piperidine. It can be represented by the following chemical formula: <chemistry id="chem0001" num="0001"><img file="EP0452273B1_D0001.tif" /></chemistry> Piperine is generally isolated from black pepper through an extraction process.

The volatile formate esters useful in this invention include those formate esters which are orally-consumable and which have a boiling point of less than 80°C. The volatile formate esters are preferably C₁-C₄ alkyl formate esters. More preferably the volatile formate esters are selected from the group consisting of ethyl formate, methyl formate, propyl formate, isoproply formate and mixtures thereof. Ethyl formate is the most preferred of the volatile formate esters.

In preparing the flavoring compositions of this invention, the pepper-like constituents and formate esters are simply blended or mixed together using conventional techniques. The pepper-like constituents and formate esters can be blended into an acceptable excipients such as (a) solvent(s), such as ethyl alcohol, and can include other optional ingredients as defined hereinbelow, such as sweeteners. A preferred composition of this invention comprises by weight from 0.1% to 0.7% of the pepper-like constituent(s), preferably piperine, from 20% to 99.4% of the volatile formate ester(s), preferably ethyl formate, as well as solvents, for example from 0% to 42% glycerine and from 0% to 65% ethyl alcohol. A more preferred embodiment comprises by weight 0.62% piperine and 99.38% ethyl formate. Another more preferred embodiment comprises by weight 0.22% piperine, 35.6% ethyl formate and 64.18% ethyl alcohol. The most preferred embodiment comprises by weight 0.13% piperine, 20.77% ethyl formate, 41.65% glycerin and 37.45% ethyl alcohol.

Examples for solvents which are useful in the chloroform substitute compositions according to this invention are glycerine, ethyl alcohol, n-propyl alcohol, iso-propyl alcohol, propylene glycol, polyoxyethylene derivatives of fatty acid partial esters of sorbitol anhydrides known under the trade name of "Tween". Preferred are glycerine and/or ethyl alcohol.

The flavoring compositions of the present invention can be uniformly incorporated into a variety of orally-consumable materials as a chloroform substitute to improve the taste thereof. The term "orally-consumable" as used herein means foodstuff, pharmaceutical and medicinal products which are swallowed, consumed or ingested, as well as those which are simply placed in the mouth and subsequently discarded. These products include pharmaceuticals such as cough syrups, cough drops, cold and allergy medicines and chewable medicinal tablets. The medicinal products can be oral hygiene compositions such as mouthwashes, mouth sprays, toothpastes and chewing gums. The foodstuffs include beverages and confectionery materials such as candies and gums.

Pharmaceutical compositions prepared according to this invention preferably comprise from 0.05% to 6% by weight of the novel flavoring composition of this invention as a substitute for chloroform. The flavoring compositions of this invention are preferably used in cough or cold medicines as a chloroform substitute. A particularly preferred cough medicine comprises by weight 11.4 parts sodium citrate, 3 parts sodium saccharin, 2 parts sodium benzoate, 700 part glucose, 39.3 parts glycerin, 2.2 parts citric acid, 27 parts ammonium chloride, 201 parts sucrose, 2.8 parts diphenhydramine hydrochloride, 0.22 parts menthol, 52.4 parts ethyl alcohol, 8.1 parts flavoring and 25 parts of said chloroform substitute flavoring composition.

Oral hygiene compositions prepared according to the present invention preferably comprise from 0.01% to 5% of this invention as a substitute for chloroform. Particularly preferred oral hygiene compositions are mouthwashes, toothpastes, chewing gums and candy breath fresheners. Confectionery products, such as candy lozenges, prepared according to this invention comprise from 0.05% to 2% by weight of the flavoring composition of the present invention as a substitute for chloroform.

The compositions of this invention can include other optional ingredients such as stabilizers, thickeners, surface active agents, conditioners and flavorants, provided that these optional ingredients are orally-consumable, non-toxic and acceptable as to taste characteristics. Stabilizer compounds include preservatives, e.g. sodium chloride, antioxidants, e.g. calcium and sodium ascorbate, ascorbic acid, butylated hydroxy-anisole (mixture of 2- and 3-tertiary-butyl-4-hydroxy-anisole), butylated hydroxy toluene (2,6-di-tertiary-butyl-4-methyl phenol), propyl gallate and the like and sequestrants, e.g. citric acid.

Thickener compounds include carriers, binders, protective colloids, suspending agents, emulsifiers and the like, e.g., agar, carrageenan; cellulose and cellulose derivatives such as carboxymethyl cellulose and methyl cellulose; natural and synthetic gums such as gum arabic, gum tragacanth; gelatin, proteinaceous materials; lipids; carbohydrates; starches, pectins, and emulsifiers, e.g., mono- and diglycerides of fatty acid, skim milk powder, hexoses, pentoses, disaccharides, e.g., sucrose corn syrup.

Surface active agents include emulsifying agents, e.g., fatty acids such as capric acid, caprylic acid, palmitic acid and myristic acid, mono- and diglycerides of fatty acids, lecithin, defoaming and flavor-dispersing agents such as sorbitan monostearate, potassium stearate and hydrogenated tallow alcohol.

Conditioners include compounds such as bleaching and maturing agents, e.g., benzoyl peroxide, calcium peroxide or hydrogen peroxide, starch modifiers such as peracetic acid, sodium chlorite, sodium hypochlorite, propylene oxide or succinic anhydride, buffers and neutralizing agents, e.g. sodium acetate, ammonium bicarbonate, ammonium phosphate, citric acid, lactic acid or vinegar; colorants, e.g., carminic acid, cochineal, tumeric and curcuma; firming agents such as aluminum sodium sulfate, calcium chloride and calcium gluconate; texturizers, anti-caking agents, e.g., aluminum calcium sulfate and tribasic calcium phosphate; enzymes; yeast foods, e.g., calcium lactate and calcium sulfate; nutrient supplements, e.g., iron salts such as ferric phosphate and ferrous gluconate, riboflavin, vitamins, zinc sources such as zinc chloride and zinc sulfate.

Other flavorants and flavor intensifiers include organic acids, e.g., acetic acid, formic acid, 2-hexenoic acid, benzoic acid, n-butyric acid, caproic acid, caprylic acid, cinnamic acid, isobutyric acid, isovaleric acid, alpha-methyl-butyric acid, propionic acid, valeric acid, 2-methyl-2-pentenoic acid, and 2-methyl-3-pentenoic acid; ketones and aldehydes, e.g., acetaldehyde, acetophenone, acetone, acetyl methyl carbinol, acrolein, n-butanal, crotonal, diacetyl, 2-methyl butanal, beta-dimethylacrolein, methyl-n-amyl ketone, n-hexenal, 2-hexenal, isopentanal, hydrocinnamic aldehyde, cis-3-hexenal, 2-heptenal, nonyl aldehyde, 4-(p-hydroxyphenyl)-2-butanone, alpha-ionone, beta-ionone, methyl-3-butanone, benzaldehyde, damascone, damascenone, acetophenone, 2-heptanone, o-hydroxyacetophenone, 2-methyl-2-hepten-6-one, 2-octanone, 2-undecanone, 3-phenyl-4-pentenal, 2-phenyl-2-hexenal, cinnamaldehyde, beta-cyclohomocitral, 2-pentanone, 2-pentenal and propanal; alcohols such as 1-butanol, benzyl alcohol, 1-borneol, trans-2-buten-1-ol, ethanol, geraniol, 1-hexanal, 2-heptanol, trans-2-hexenol-1, cis-3-hexen-1-ol, 3-methyl-3-buten-1-ol, 1-pentanol, 1-penten-3-ol, p-hydroxyphenyl-2-ethanol, isoamyl alcohol, isofenchyl alcohol, phenyl-2-ethanol, alpha-terpineol, cis-terpineol hydrate, eugenol, linalool, 2-heptanol, acetoin; esters, such as butyl acetate, ethyl acetate, ethyl acetoacetate, ethyl benzoate, ethyl butyrate, ethyl caprate, ethyl caproate, ethyl caprylate, ethyl cinnamate, ethyl crotonate, ethyl isobutyrate, ethyl isovalerate, ethyl laurate, ethyl myristate, ethyl alpha-methylbuytrate, ethyl propionate, ethyl salicylate, trans-2-hexenyl acetate, hexyl acetate, 2-hexenyl butyrate, hexyl butyrate, isoamyl acetate, isopropyl butyrate, methyl acetate, methyl butyrate, methyl caproate, methyl isobutyrate, alpha-methylphenylglycidate, ethyl succinate, isobutyl cinnamate, cinnamyl formate, methyl cinnamate and terpenyl acetate; terpene hydrocarbons such as myrcene, caryophyllene, 1-phellandrene, p-cymene, 1-alpha-pinene, beta-pinene, dihydrocarveol; pyrazines such as 2,3-dimethylpyrazine, 2,5-dimethylpyrazine, 2,6-dimethyl-pryrazine, 3-ethyl-2,5-dimethylpyrazine, 2-ethyl-3,5,6-trimethylpyrazine, 3-isoamyl-2,5-dimethyl-pyrazine, 5-isoamyl-2,3-dimethylpyrazine, 2-isoamyl-3,5,6-trimethylpyrazine, isopropyl dimethylpyrazine, methyl ethylpyrazine, tetramethylpyrazine, trimethylpyrazine; essential oils and extracts such as jasmine absolute, cassia oil, cinnamon bark oil, rose absolute, orris absolute, oil of cubeb, oil of coriander, oil of pimento leaf, oil of patchouli, oil of nutmeg, lemon oil, safron oil, Bulgarian rose, yara yara and vanilla; lactones such as gamma-nonalactone; sulfides, e.g., methyl sulfide and other materials such as maltol, acetoin and acetals (e.g., 1,1-diethoxyethane, 1,1-dimethoxyethane and dimethoxymethane), and piperidine.

The following examples are presented to further demonstrate this invention. All parts and percentages are on a weight basis unless otherwise indicated.

EXAMPLE I

Flavoring compositions falling within the scope of this invention were prepared by uniformly mixing the ingredients in the amounts shown in Table I below: <tables id="tabl0001" num="0001"><table frame="all"><title>TABLE I</title><tgroup cols="4" colsep="1" rowsep="0"><colspec colnum="1" colname="col1" colwidth="39.37mm" /><colspec colnum="2" colname="col2" colwidth="39.37mm" /><colspec colnum="3" colname="col3" colwidth="39.37mm" /><colspec colnum="4" colname="col4" colwidth="39.37mm" /><thead valign="top"><row><entry namest="col1" nameend="col1" align="center">Sample:</entry><entry namest="col2" nameend="col2" align="center">A</entry><entry namest="col3" nameend="col3" align="center">B</entry><entry namest="col4" nameend="col4" align="center">C</entry></row><row><entry namest="col1" nameend="col1" align="center">Ingredient:</entry><entry namest="col2" nameend="col2" /><entry namest="col3" nameend="col3" /><entry namest="col4" nameend="col4" /></row></thead><tbody valign="top"><row><entry namest="col1" nameend="col1" align="left">Ethyl Formate</entry><entry namest="col2" nameend="col2" align="char" char=".">20.77%</entry><entry namest="col3" nameend="col3" align="char" char=".">99.38%</entry><entry namest="col4" nameend="col4" align="char" char=".">35.6%</entry></row><row><entry namest="col1" nameend="col1" align="left">Piperine</entry><entry namest="col2" nameend="col2" align="char" char=".">0.13%</entry><entry namest="col3" nameend="col3" align="char" char=".">0.62%</entry><entry namest="col4" nameend="col4" align="char" char=".">0.22%</entry></row><row><entry namest="col1" nameend="col1" align="left">Ethyl Alcohol</entry><entry namest="col2" nameend="col2" align="char" char=".">37.45%</entry><entry namest="col3" nameend="col3" align="char" char=".">0.0%</entry><entry namest="col4" nameend="col4" align="char" char=".">64.18%</entry></row><row rowsep="1"><entry namest="col1" nameend="col1" align="left">Glycerin</entry><entry namest="col2" nameend="col2" align="char" char=".">41.65%</entry><entry namest="col3" nameend="col3" align="char" char=".">0.0%</entry><entry namest="col4" nameend="col4" align="char" char=".">0.0%</entry></row></tbody></tgroup></table></tables>

EXAMPLE II

The flavoring compositions prepared in Example I were each admixed with toothpaste as a substitute for chloroform and evaluated for taste characteristics. The toothpastes containing the flavoring compositions of this invention were compared to toothpaste containing chloroform. The specific formulations for these toothpaste samples are presented in Table II below: <tables id="tabl0002" num="0002"><table frame="all"><title>TABLE II</title><tgroup cols="5" colsep="1" rowsep="0"><colspec colnum="1" colname="col1" colwidth="31.50mm" /><colspec colnum="2" colname="col2" colwidth="31.50mm" /><colspec colnum="3" colname="col3" colwidth="31.50mm" /><colspec colnum="4" colname="col4" colwidth="31.50mm" /><colspec colnum="5" colname="col5" colwidth="31.50mm" /><thead valign="top"><row><entry namest="col1" nameend="col1" align="center">Sample:</entry><entry namest="col2" nameend="col2" align="left">D</entry><entry namest="col3" nameend="col3" align="center">E</entry><entry namest="col4" nameend="col4" align="center">F</entry><entry namest="col5" nameend="col5" align="center">G(Control)</entry></row><row><entry namest="col1" nameend="col1" align="center">Ingredient:</entry><entry namest="col2" nameend="col2" /><entry namest="col3" nameend="col3" /><entry namest="col4" nameend="col4" /><entry namest="col5" nameend="col5" /></row></thead><tbody valign="top"><row><entry namest="col1" nameend="col1" align="left">Mint Flavored Toothpaste</entry><entry namest="col2" nameend="col2" align="char" char=".">99.25%</entry><entry namest="col3" nameend="col3" align="char" char=".">99.89%</entry><entry namest="col4" nameend="col4" align="char" char=".">99.55%</entry><entry namest="col5" nameend="col5" align="char" char=".">99.33%</entry></row><row><entry namest="col1" nameend="col1" align="left">Flavoring Composition Sample A</entry><entry namest="col2" nameend="col2" align="char" char=".">0.75%</entry><entry namest="col3" nameend="col3" align="char" char=".">-</entry><entry namest="col4" nameend="col4" align="char" char=".">-</entry><entry namest="col5" nameend="col5" align="char" char=".">-</entry></row><row><entry namest="col1" nameend="col1" align="left">Flavoring Composition Sample B</entry><entry namest="col2" nameend="col2" align="char" char=".">-</entry><entry namest="col3" nameend="col3" align="char" char=".">0.11%</entry><entry namest="col4" nameend="col4" align="char" char=".">0.045%</entry><entry namest="col5" nameend="col5" align="char" char=".">-</entry></row><row rowsep="1"><entry namest="col1" nameend="col1" align="left">Flavoring Composition Sample C</entry><entry namest="col2" nameend="col2" align="char" char=".">-</entry><entry namest="col3" nameend="col3" align="char" char=".">-</entry><entry namest="col4" nameend="col4" align="char" char=".">-</entry><entry namest="col5" nameend="col5" align="char" char=".">0.67%</entry></row></tbody></tgroup></table></tables>

Samples D, E, and F, falling within the scope of this invention, were each judged to simulate the odor, diffusivity and taste of Sample G, which contained chloroform. Sample D was judged to be equivalent to Sample G in the above characteristic, while Sample E and Sample F were judged to be better.

EXAMPLE III

A cough syrup base formulation was prepared as follows: <tables id="tabl0003" num="0003"><table frame="all"><tgroup cols="2" colsep="1" rowsep="0"><colspec colnum="1" colname="col1" colwidth="78.75mm" /><colspec colnum="2" colname="col2" colwidth="78.75mm" /><thead valign="top"><row><entry namest="col1" nameend="col1" align="left">Ingredient</entry><entry namest="col2" nameend="col2" align="center">Amount/Liter</entry></row></thead><tbody valign="top"><row><entry namest="col1" nameend="col1" align="left">Sodium Citrate</entry><entry namest="col2" nameend="col2" align="char" char=".">11.40 grams</entry></row><row><entry namest="col1" nameend="col1" align="left">Sodium Saccharin</entry><entry namest="col2" nameend="col2" align="char" char=".">3.00 grams</entry></row><row><entry namest="col1" nameend="col1" align="left">Sodium Benzoate</entry><entry namest="col2" nameend="col2" align="char" char=".">2.00 grams</entry></row><row><entry namest="col1" nameend="col1" align="left">Liquid Glucose</entry><entry namest="col2" nameend="col2" align="char" char=".">700.00 grams</entry></row><row><entry namest="col1" nameend="col1" align="left">Glycerin</entry><entry namest="col2" nameend="col2" align="char" char=".">39.30 grams</entry></row><row><entry namest="col1" nameend="col1" align="left">Citric Acid</entry><entry namest="col2" nameend="col2" align="char" char=".">2.20 grams</entry></row><row><entry namest="col1" nameend="col1" align="left">Ammonium Chloride</entry><entry namest="col2" nameend="col2" align="char" char=".">27.00 grams</entry></row><row><entry namest="col1" nameend="col1" align="left">Sucrose</entry><entry namest="col2" nameend="col2" align="char" char=".">201.00 grams</entry></row><row><entry namest="col1" nameend="col1" align="left">Diphenhydramine Hydrochloride</entry><entry namest="col2" nameend="col2" align="char" char=".">2.80 grams</entry></row><row><entry namest="col1" nameend="col1" align="left">Menthol</entry><entry namest="col2" nameend="col2" align="char" char=".">0.22 grams</entry></row><row><entry namest="col1" nameend="col1" align="left">Ethyl Alcohol (USP 95%)</entry><entry namest="col2" nameend="col2" align="char" char=".">52.40 ml.</entry></row><row><entry namest="col1" nameend="col1" align="left">Flavorants (Caramel/Ponceau 4R/Raspberry)</entry><entry namest="col2" nameend="col2" align="char" char=".">8.10 grams</entry></row><row rowsep="1"><entry namest="col1" nameend="col2" align="justify">Diluted with deionized water to 1 liter.</entry></row></tbody></tgroup></table></tables>

A cough syrup composition (Sample H) within the scope of this invention was prepared comprising 97.5% of the cough syrup base formulation above and 2.5% of the flavoring composition Sample A prepared in Example I. Sample H was compared to a control cough syrup composition comprising a similar cough syrup base and 0.67% chloroform. Sample H was evaluated by an experienced taste panel to have similar taste, mouthfeel and diffusive aroma as the control cough syrup composition containing chloroform.