JPH1028724A - Fragrant deodorizing composition for feces - Google Patents

Abstract

PROBLEM TO BE SOLVED: To effectively deodorize the smell of feces by incorporating a scent glycoside having a β bond of a scent compound and sugar as effective component. SOLUTION: Enterobacterium which produces ammonia, mercaptans, amines and the like regarded as causes of offensive smell of feces efficiently decomposes a scent glycoside having a β bond to generate fragrance by isolating scent components. In view of this, a compound which has scent glycoside in a bond of a scent compound is contained as effective component to prepare a fragrant deodorizing composition for feces. In this process, the blending concentration of the scent glycoside in the fragrant deodorizing composition for feces is not limited because it varies with the threshold of the scent components composing the scent glycoside. But the blending concentration is preferably in a range of about 0.01-30wt.% in terms of the concentration of the scent glycoside in light of preference and fragrant deodorizing action. The scent glycoside herein applicable has a β bond which is invulnerable to decomposition by a digestive enzyme and is decomposed by the enterobacterium to isolate the scent components.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a feces fragrance deodorant composition.

[0002]

2. Description of the Related Art In order to deodorize excrement odors of humans, pet animals, livestock, etc., they are installed or sprayed in toilets or indoors to emit fragrances, and to excrete by ingesting fragrances or odors by oral ingestion. A plurality of deodorants have been already provided to eliminate the odor. As a deodorant of the type to be taken orally, biscuits containing silica gel (Japanese Unexamined Patent Publication No. Hei 6-33
No. 9344), a mushroom extract for neutralizing or adding a malodorous substance (JP-A-5-38358), and dietary fiber alone which is considered to improve the intestinal flora and reduce the production of putrefactive metabolites having malodor ( JP-A-6-21776
No. 1) or a combination of dietary fiber and tannic acid (JP-A-6-256180).

[0003]

However, the odor of feces is mainly a complex odor of a plurality of components such as ammonia, mercaptans, amines, indole and skatole, which are metabolites by intestinal bacteria. With this type of deodorant, it is difficult to deal with the odor components of all feces, and the deodorization of feces was incomplete. In addition, even if a perfume is taken orally to give a scent to feces and try to mask a bad smell, when it reaches the digestive tract, it is absorbed and metabolized and loses the scent. It is not possible.

[0004]

Means for Solving the Problems The present inventors have studied diligently to solve such problems, and they are not decomposed by digestive enzymes, but are decomposed by intestinal bacteria to release fragrance components, and the fragrance components are released. Produces ammonia, mercaptans, amines, indole, skatole, etc., which are the causes of unpleasant odor in feces, based on the knowledge that the expected effect can be achieved by excreting with feces The present inventor has found that intestinal bacteria that efficiently decompose a fragrance glycoside having a β bond to release a fragrance component and generate an aroma, thereby completing the present invention. This was first clarified by the present inventors and has not been reported at all.

That is, the present invention relates to a feces fragrance deodorant composition containing, as an active ingredient, a compound obtained by converting a fragrance compound into a fragrance glycoside having a β bond. The concentration of the fragrance glycoside in the stool aroma deodorant composition varies depending on the threshold value of the fragrance component constituting the fragrance glycoside, and cannot be specified unconditionally. 0
The content in the range of 1 to about 30% by weight is preferable from the viewpoint of palatability and aroma deodorizing action. The fragrance compound is preferably one having a hydroxyl group, and as a fragrance glycoside, has a β bond that is difficult to be decomposed by digestive enzymes,
Any substance can be used as long as it is decomposed by intestinal bacteria and releases a fragrance component.

[0006] Specifically, aglycones corresponding to flavor compounds include cis-3-hexenol, linalool,
Geraniol, nerol, citronellol, rosinol, dimethyloctanol, hydroxycitronellol, tetrahydrolinalool, lavandulol, myrcenol, α-terpineol, l-menthol, borneol, dimethylphenylcarbinol, β-phenylethyldimethylcarbinol, β-phenylethyl Methyl ethyl carbinol, phenoxyethyl alcohol, phenyl glycol, tertiary butyl cyclohexanol, hydroxycitronellal, methyl salicylate,
Ethyl salicylate, isobutyl salicylate, isoamyl salicylate, benzyl salicylate, phenylethyl salicylate, linalool oxide, vanillin, ethyl vanillin, linal, maltol, thymol, carvacrol, eugenol, isoeugenol, isopulegol, nopol, farnesol, nerolidol, santachlor, Examples include cedrol, vetiverol, benzyl alcohol, 2-phenylethyl alcohol, γ-phenylpropyl alcohol, cinnamic alcohol, anis alcohol, dimethylbenzylcarbinol, and methylphenylcarbinol.

Examples of the sugar moiety include monosaccharides (glucose, galactose, mannose, glucosamine, galactosamine, rhamnose, xylose, ribose, arabinose, etc.) and disaccharides (sucrose, lactose, maltose, gentibiose, cellobiose, isomaltose,
Primeverose, Vicianose, Rutinose, etc.).

[0008] The bond between the fragrance compound and the sugar is a β bond which is not easily decomposed by digestive enzymes and is easily decomposed by intestinal bacteria. The flavor glycosides are commercially available and are easily available, but can also be synthesized by a known method. In addition, an extract containing a fragrance glycoside can also be obtained from natural raw materials.

The stool deodorant composition of the present invention can be produced by blending at least one of the above-mentioned fragrance glycosides.
Includes various compositions that emit an aroma based on the perfume compound corresponding to the aglycone moiety. Specific examples include soft drinks, confectionery, frozen desserts, dairy products, alcoholic beverages, meats, foods such as deodorant foods, probiotic agents, various forms of pharmaceuticals such as gastrointestinal drugs, pet foods, livestock feeds, and the like. .

Next, an example of synthesis of a fragrance glycoside and the results of a decomposition test with an enzyme will be described.

Synthesis of Geranyl-β-D-glucoside 2.39 g of geraniol and 4.11 g of tetraacetyl-α-D-glucose bromide according to the method disclosed in Oil Chemistry, Vol. 43, 31-38 (1994). Was dissolved in ether, 7.1 g of silver carbonate supported on silica gel, and 5 g of molecular sieve 4A were added and reacted at 40 ° C. After distilling off ether, the mixture was hydrolyzed with sodium methoxide and further neutralized with a cation exchange resin, and then the reaction product was purified by silica gel column chromatography to obtain 1.49 g of geranyl-β-D-glucoside. (Yield 47%)

Nuclear magnetic resonance spectrum (CD ₃ OD) δ (ppm) of geranyl-β-D-glucoside: 1.60
(3H, s), 1.68 (6H, s), 2.08 (4
H, m), 3.17 (4H, m), 3.63-3.89
(2H, dd), 4.20 to 4.37 (2H, m),
4.28 (1H, d, J = 7.7 Hz), 5.10 (1
H, t), 5.36 (1H, t)

Synthesis of 2-phenylethyl-β-D-glucoside A method for synthesizing sugar derivatives of maltol in the method disclosed in Oil Chemistry, Vol. 44, pp. 23-29 (1995) was partially modified to give 2-phenylethyl-β-D-glucoside. 20.0 g of phenylethyl alcohol and 14.0 g of cellobiose were added to 1 liter of McIlvaine buffer (pH 4.0).
5) and 10.0 g of Cellulase Amano-T was added and reacted. The reaction solution was purified by chromatography on XAD-2 gel by elution with methanol,
1.21 g of -phenylethyl-β-D-glucoside was obtained. (Yield 7%)

Synthesis of cis-3-hexenyl-β-D-glucoside According to the method disclosed in Oil Chemistry, Vol. 43, pp. 31-38 (1994), cis-3-hexenol 1.58 was prepared.
g of tetraacetyl-α-D-glucose bromide was dissolved in ether, and 7.1 g of silver carbonate supported on silica gel and 5 g of molecular sieve 4A were added.
Was reacted. After distilling off the ether, hydrolyzing with sodium methoxide and neutralizing with a cation exchange resin, the reaction product was purified by silica gel column chromatography to obtain cis-3-hexenyl-β-D-glucoside. 05 g were obtained. (40% yield)

Synthesis of linalool oxide-β-D-glucoside 2.64 g of linalool oxide and tetraacetyl-α-D-glucose bromide according to the method disclosed in Oil Chemistry, Vol. 43, pp. 31-38 (1994). 1
1 g was dissolved in ether, and 7.1 g of silver carbonate supported on silica gel was obtained.
g and molecular sieve 4A5g were added and reacted at 40 ° C. After distilling off the ether, hydrolyzing with sodium methoxide and further neutralizing with a cation exchange resin, the reaction product was purified by silica gel column chromatography, and linalool oxide-β-D-glucoside 0.51 was purified.
g was obtained. (Yield 15%)

Degradation test by amyloglucosidase In order to examine whether or not the flavor glycoside serves as a substrate for the digestive enzyme amyloglucosidase, a degradation test of the flavor glycoside by amyloglucosidase was performed, and the product was evaluated by TLC.
Geranyl-β-D-glucoside, 2-phenylethyl-
β-D-glucoside and cis-3-hexenyl-β-
For D-glucoside, 10 mg / ml of McIlvaine
200 µl of a buffer solution (pH 4.5) was prepared, 200 µl of a McIlvaine buffer solution (pH 4.5) containing 0.56 mg / ml of amyloglucosidase was added, and the mixture was allowed to stand at 55 ° C. After 6 hours, the product was confirmed by TLC. Table 1 shows the test results.

Decomposition test with lipase In order to examine whether the fragrance glycoside serves as a substrate for lipase, which is a digestive enzyme, a lipase decomposition test of the fragrance glycoside was performed.
The product was evaluated by TLC. For geranyl-β-D-glucoside, 2-phenylethyl-β-D-glucoside and cis-3-hexenyl-β-D-glucoside,
10 mg / ml sodium phosphate buffer solution (pH
7.7) Prepare 200 μl and add 21.4 μg /
20 ml of sodium phosphate buffer solution (pH 7.7)
0 μl was added and left at 37 ° C. After 6 hours, TLC
The product was evaluated by Table 1 shows the test results.

Degradation Test with β-Glucosidase In order to examine whether the fragrance glycoside serves as a substrate for β-glucosidase which is an intestinal bacterium, a decomposition test of the fragrance glycoside with β-glucosidase is performed, and the product is evaluated by TLC. At the same time, the production of flavor components from the flavor glycoside was evaluated using gas chromatography. Geranyl-β-D-
For glucoside, 2-phenylethyl-β-D-glucoside and cis-3-hexenyl-β-D-glucoside, a 10 mg / ml citrate buffer solution (pH 5.
0) 5 ml was prepared, 50 mg of β-glucosidase was added, and the mixture was allowed to stand at 37 ° C. One hour later, TLC analysis was performed, and aroma components were extracted with ether and analyzed by gas chromatography. The test results are shown in Tables 1 and 2.

[0019]

[Table 1]

[0020]

[Table 2]

As shown in Table 1, the fragrance glycoside was not degraded by the digestive enzymes amyloglucosidase and lipase, but was rapidly degraded by β-glucosidase of the intestinal bacteria. In addition, as shown in Table 2, a flavor component was produced from the flavor glycoside by β-glucosidase.

Metabolism test of fragrance glycoside by intestinal bacteria Metabolism test of fragrance glycoside by intestinal bacteria was performed, and the production of fragrance components from the fragrance glycoside was evaluated using gas chromatography. 5 ml of PYF (Peptone Ye)
ast extract Fields soluti
on) 10 mM 2-phenylethyl-β-D-glucoside was added to the medium. EGF (Egger)
the Gagnon Fields solution
n) 0.4% of bacterial liquid of various intestinal bacteria cultured in a medium was inoculated and anaerobically cultured at 37 ° C. Two days after the culture, the mixture was extracted with ether and analyzed by gas chromatography. Table 3 shows the results.

[0023]

[Table 3]

As shown in Table 3, the flavor glycoside was converted to 2-
Intestinal bacterial strains producing phenylethyl alcohol were 5 of the 6 tested strains.

[0025]

DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described in more detail with reference to the following examples, but the scope of the present invention is not limited to these examples.

Examples 1 to 3 and Comparative Example Candies were prepared according to the formulations shown in Table 4. Each candy was made according to the conventional method commonly used for its production.

[0027]

[Table 4]

Sensory Evaluation Test In order to evaluate the aroma deodorizing effect and flavor of the stool aroma deodorizing composition of the present invention, a total of 20 adult males and females were evaluated.
A sensory test was conducted using the name (25-56 years old) as a panelist. 3 days a week to panelists (6g per day)
In the eating period, the compositions of Examples 1 to 3 and Comparative Example were each eaten (for a total of 4 weeks), and the flavor and the smell of defecation were judged according to the evaluation criteria shown in Table 5, and the flavor and The aroma deodorizing effect on fecal odor was scored. Table 6 shows the results.

[0029]

[Table 5]

[0030]

[Table 6]

As shown in Table 6, the evaluations of Examples 1 to 3 were almost the same as those of the Comparative Example in terms of flavor, but it was confirmed that Examples 1 to 3 developed scent in stool, It was found to have an odor effect.

Example 4 A candy was prepared according to the following recipe. Granulated sugar 45 parts Water syrup (DE.42) 50 parts Water 20 parts Green tea extract (deodorant) 3 parts Linalool oxide-β-D-glucoside 3 parts Flavor 1 part

Example 5 A chewing gum was prepared according to the following formulation according to a commonly used conventional method. Gum base 20 parts sugar 56 parts starch syrup 13 parts glucose 10 parts cis-3-hexenyl-β-D-glucoside 5 parts softener 1 part flavor 0.5 part

Example 6 A chewing gum was prepared according to the following formulation. Gum base 20 parts sugar 56 parts starch syrup 13 parts glucose 10 parts 2-phenylethyl-β-D-glucoside 5 parts green tea extract (deodorant) 1 part softener 1 part flavor 0.5 part

Example 7 Chocolate was prepared according to the following recipe according to a commonly used conventional method. Cocoa bitter 20 parts Cocoa butter 17 parts Sugar 43 parts Whole milk powder 20 parts Geranyl-β-D-glucoside 1 part Fragrance 0.2 part

Example 8 Tablets were prepared according to the following formulation according to a commonly used conventional method. Lactose 100 parts Potato starch 100 parts 2-phenylethyl-β-D-glucoside 60 parts

Example 9 A biscuit was prepared according to the following recipe according to a commonly used conventional method. Soft flour 100 parts Shortening 30 parts Powdered sugar 32 parts Ginger syrup (DE.42) 5 parts Skim milk powder 1.8 parts Salt 1.1 parts Commercial 2-phenylethyl-β-D-galactoside 1 part (manufactured by SIGMA) 0.45 parts leavening agent

[0038]

The perfume glycoside of the present invention, when ingested orally, is difficult to be decomposed by digestive enzymes including saliva, but is decomposed by intestinal bacteria to separate and produce perfume components. Sometimes discharged with stool. It is recognized that the fragrance component imparts a preferable fragrance to humans, such as a floral scent or green notes, and masks and neutralizes the odor of feces.

According to the composition of the present invention, since the fragrance component exists as a fragrance glycoside, even when used in combination with a conventional deodorant, the fragrance does not disappear due to the conventional deodorant.
On the contrary, it was also recognized that the deodorizing effect increased additively or synergistically.

Claims (3)

[Claims] 1. A fecal aroma deodorant composition comprising, as an active ingredient, a perfume glycoside in which the bond between a perfume compound and sugar is a β bond. 2. A fecal aroma deodorant composition comprising, as an active ingredient, a perfume glycoside in which the bond between a fragrance compound having a hydroxyl group and sugar is a β bond. 3. The stool deodorant composition according to claim 1, wherein the concentration of the fragrance glycoside in the composition is in the range of about 0.01 to about 30% by weight.