JP2005104856A - Dental plaque formation inhibitor composition, and food and drink or oral hygienic agent containing the composition - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a dental plaque formation inhibitor composition which can be compounded with a drink and food or an oral hygienic agent to inhibit the formation of dental plaques and prevent dental caries and periodontal diseases without deteriorating the original smell and taste of the drink and food or the oral hygienic agent. <P>SOLUTION: This dental plaque formation inhibitor composition is characterized by comprising one or more isothiocyanate compounds selected from the group consisting of an ω-alkenyl isothiocyanate compound represented by formula [1]: CH<SB>2</SB>=CH-(CH<SB>2</SB>)<SB>m</SB>-NCS [(m) is an integer of 2 to 10], an ω-alkylthioalkyl isothiocyanate compound represented by formula [2]: R-S-(CH<SB>2</SB>)<SB>n</SB>-NCS [(n) is an integer of 1 to 10; R is a 1 to 4C alkyl], and an ω-phenylalkyl isothiocyanate compound represented by formula [3]: Ph-(CH<SB>2</SB>)<SB>p</SB>-NCS [Ph is phenyl; (p) is an integer of 1 to 10], and a tea leaf extract extracted from tea leaves with water and/or a polar organic solvent. <P>COPYRIGHT: (C)2005,JPO&NCIPI

Description

The present invention relates to one or more isothiocyanate compounds selected from the group consisting of ω-alkenyl isothiocyanate compounds, ω-alkyl thioalkyl isothiocyanate compounds, and ω-phenyl alkyl isothiocyanate compounds, and tea leaves. It is related with the plaque formation inhibitor composition characterized by containing an extract.
Moreover, this invention relates to the food-drinks or oral hygiene agent containing the said plaque formation inhibitor composition.

  Caries (caries) are enamel that is a metabolite of lactic acid and other organic acids produced by mutans bacteria (Streptococcus mutans; hereinafter abbreviated as “S. mutans”) in the plaque. It is caused by eroding quality. Dental plaque is a mass formed by aggregation of polysaccharide glucan produced from sucrose by the action of glucosyltransferase, an extracellular enzyme of S. mutans, and S. mutans and other gram-negative bacteria. When plaque is produced not at the tooth surface but at the junction with the gums or at the root of the tooth, anaerobic gram-negative bacteria can lead to periodontal disease. Therefore, it is possible to prevent the occurrence of caries and periodontal disease by suppressing the generation of dental plaque.

In order to suppress dental caries, that is, to suppress plaque formation, conventionally, a method using polyphenols in tea leaf extracts of green tea, oolong tea, and black tea (for example, see Patent Document 1 and Patent Document 2) is known. ing. This plaque formation-inhibiting effect is based on the fact that polyphenols in tea leaf extract inhibit the action of glucosyltransferase, an extracellular enzyme of S. mutans, thereby suppressing the production of glucan from sucrose. (For example, see Non-Patent Document 1 and Non-Patent Document 2).
The plaque formation inhibitory effect depends on the amount of polyphenols in the tea leaf extract, and the plaque formation inhibitory effect increases as the amount added increases. However, since the polyphenols contained in tea leaves have a strong astringency, when used in a large amount in foods and drinks, the astringency adversely affects the original flavor of the final product. Therefore, if the amount of tea leaf extract is reduced to reduce astringency, the effect of inhibiting plaque formation will be reduced.

On the other hand, a method for suppressing plaque formation using an isothiocyanate compound (see, for example, Patent Document 3 and Patent Document 4) has also been proposed.
However, the isothiocyanate compound is a component characteristic of the wasabi flavor and has a wasabi-like stimulating flavor, and thus becomes an obstacle when used for food and drink. Therefore, in order to prevent the wasabi-like stimulating flavor from appearing in the final product, it is necessary to reduce the amount of isothiocyanate compound added, but the effect of inhibiting plaque formation is reduced.

Components derived from natural products are highly safe and have the advantage of being easily added to foods and drinks. However, each natural product component usually has a unique taste and smell, and when used in combination, there is a risk of adverse effects on the quality of the product due to discomfort due to the total effect of such unique taste and smell. There is. Therefore, there are cases where attempts are made to use natural product ingredients that have the same taste and smell, but natural product ingredients that have different types of taste and smell such as astringency and wasabi-like pungent odor are applied to food and drink. This is difficult to think for those skilled in the art who place importance on the original taste of the product from the standpoint of the consumer rather than the efficacy of the additive component, and it was natural to avoid it.
Japanese Patent Laid-Open No. 1-265010 JP-A-2-25413 Japanese Patent Laid-Open No. 11-139948 JP-A-11-139949 Fragrance Journal 18 42 (1990) Japan Food Science 1 28 (1993)

  The problem of the present invention is to solve the above-mentioned problems in the prior art, and the original flavor of foods and beverages and oral hygiene agents is not felt without the astringency and wasabi-like stimulating flavor brought about by the plaque formation inhibitor. On the other hand, a plaque formation inhibitor composition that has a high plaque formation inhibitory effect and can prevent the occurrence of caries and periodontal disease, and the composition applied thereto The object is to provide food and drink and oral hygiene.

  Among the many known plaque formation inhibitors, the present inventors are selected from the group consisting of ω-alkenyl isothiocyanate compounds, ω-alkyl thioalkyl isothiocyanates and ω-phenyl alkyl isothiocyanate compounds. When a seed or two or more isothiocyanate compounds are used in combination with a tea leaf extract, a surprisingly synergistic effect is exhibited, and plaque formation occurs even in much smaller amounts than when each is used alone. The present inventors have found that the inhibitory effect is increased, thereby finding that the amount applied to food and drink can be reduced to such an extent that no wasabi-like stimulating flavor or astringency is felt, and the present invention has been completed.

That is, the present invention is represented by an ω-alkenyl isothiocyanate compound represented by the following formula [1], an ω-alkylthioalkyl isothiocyanate compound represented by the following formula [2], and the following formula [3]. Contains one or more isothiocyanate compounds selected from the group consisting of ω-phenylalkyl isothiocyanate compounds, and tea leaf extract extracted from tea leaves using water and / or polar organic solvents It is a dental plaque formation inhibitor composition characterized by carrying out.
Equation _{(1): CH 2 = CH- (CH 2} ) m -NCS
(In the formula, m represents an integer of 2 to 10)
Formula [2]: RS— (CH ₂ ) _n —NCS
(In the formula, n represents an integer of 1 to 10, and R has 1 to 4 carbon atoms.
Represents an alkyl group)
Formula [3]: Ph- (CH ₂ ) _p -NCS
(In the formula, Ph represents a phenyl group, and p represents an integer of 1 to 10).

The plaque formation inhibitor composition of the present invention is characterized by containing 0.01 to 1% by weight of an isothiocyanate compound and 0.1 to 10% by weight of a tea leaf extract.
The tea leaf is one or more tea leaves selected from the group consisting of green tea, black tea and oolong tea, and the isothiocyanate compound is 4-pentenyl isothiocyanate, 6-methylthiohexyl isothiocyan. It is one or two or more compounds selected from the group consisting of nato, 5-methylthiopentyl isothiocyanate and benzyl isothiocyanate.

  Furthermore, the present invention is a food or drink or oral hygiene agent containing the above-mentioned plaque formation inhibitor composition, and further contains 0.01 to 5% by weight of the plaque formation inhibitor composition. Is a food or drink or oral hygiene agent.

The plaque formation inhibitor composition of the present invention is effective as a preventive agent for caries and periodontal disease because it suppresses plaque formation by S. mutans.
Ingredients of the plaque formation inhibitor composition of the present invention are a natural isothiocyanate compound that is contained in trace amounts in the wasabi flavor component that has been used in food since ancient times, and is enjoyed by many people every day. Because it is a tea leaf extract (the main component is polyphenols), it is highly safe.
Because of the synergistic effect of the isothiocyanate compound and tea leaf extract, the plaque formation inhibitory effect is greatly exhibited at a much lower addition amount than when used alone, so that the flavor of the final product is impaired. Absent.
Therefore, it is suitable for use in foods and beverages such as confectionery and juice, or in oral hygiene agents such as toothpastes and mouth washes.

Hereinafter, the present invention will be described in detail.
The present invention is a plaque formation inhibitor composition that exhibits a synergistic effect by using an isothiocyanate compound, which will be described in detail below, and a tea leaf extract in combination, and has an extremely excellent plaque formation inhibitory effect even when added in a small amount. is there.

(1) Isothiocyanate compound The isothiocyanate compound used in the present invention is selected from the group consisting of ω-alkenyl isothiocyanate compounds, ω-alkyl thioalkyl isothiocyanate compounds, and ω-phenylalkyl isothiocyanate compounds. Or one or more isothiocyanate compounds.

1) The ω-alkenyl isothiocyanate compound is represented by the following formula [1].
Equation _{(1): CH 2 = CH- (CH 2} ) m -NCS
In the above formula, m represents an integer of 2 to 10, preferably 3 to 8, and particularly preferably an integer of 3 to 5.
Specific examples of the compound having the structure of the formula [1] include 3-butenyl isothiocyanate, 4-pentenyl isothiocyanate, 5-hexenyl isothiocyanate, 6-heptenyl isothiocyanate, and 7-octenyl isothiocyanate. Oceanate. Among these, 4-pentenyl isothiocyanate is preferable from the viewpoint that the irritating odor is relatively weak and the residual fragrance property is relatively low.

In the formula [1], the compound having m of 5 or less is known to be contained in aroma components such as wasabi and horseradish, but since the amount thereof is extremely small, it is industrially It is appropriate to obtain by synthesis.
The method for synthesizing the compound is disclosed in, for example, JP-A-2-221255, and the outline thereof is CH ₂ ═CH— (CH ₂ ) _m —X in the inert solvent. And ω-alkenyl thiocyanate obtained by reacting ω-alkenyl halide having a structure of the following formula with the thiocyanate: Is obtained by isomerization in a polar aprotic solvent.

2) The ω-alkylthioalkyl isothiocyanate compound is represented by the following formula [2].
Formula [2]: RS— (CH ₂ ) _n —NCS
In said formula, although n represents the integer of 1-10, 3-8 are preferable and the integer of 4-7 is especially preferable. R represents an alkyl group having 1 to 4 carbon atoms. Preferred examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, etc. A methyl group is preferred from the viewpoint of relatively low residual fragrance.

Examples of the compound having the structure of the formula [2] include methylthiomethyl isothiocyanate, ethyl thiomethyl isothiocyanate, n-propyl thiomethyl isothiocyanate, isopropyl thiomethyl isothiocyanate, n-butyl thiomethyl isothiocyanate. Narate, isobutylthiomethyl isothiocyanate, sec-butylthiomethyl isothiocyanate, 2-methylthioethyl isothiocyanate, 2-ethylthioethyl isothiocyanate, 2-n-propylthioethyl isothiocyanate, 3-methylthiopropyl Isothiocyanate, 4-methylthiobutyl isothiocyanate, 5-methylthiopentyl isothiocyanate, 6-methylthiohexyl isothiocyanate, 7-methylthioheptyl isothiocyanate, 8-methylthiooate Examples include octyl isothiocyanate and 9-methylthiononyl isothiocyanate.
Among these, 6-methylthiohexyl isothiocyanate and 5-methylthiopentyl isothiocyanate are preferable because they have no flavor and have relatively low residual fragrance.

In the formula [2], it is known that a compound in which n is 8 or less is contained in aroma components such as wasabi and horseradish, but since the amount thereof is extremely small, it is obtained industrially. It is appropriate to use synthesis.
A method for synthesizing the compound is disclosed in, for example, Japanese Patent Application Laid-Open No. 7-215931. The outline of the compound is CH ₂ ═CH— (CH ₂ ) _n−2− X [wherein n Represents an integer of 3 to 10, preferably 3 to 8, and particularly preferably an integer of 4 to 7. The ω-alkenyl isothiocyanate having the structure is obtained by reacting with an alkyl mercaptan having R—SH [wherein R has the same meaning as described above].

3) The ω-phenylalkyl isothiocyanate compound is represented by the following formula [3].
Formula [3]: Ph— (CH ₂ ) _p —NCS (Ph is a phenyl group)
In said formula, although p represents the integer of 1-10, Preferably it is 3-8, The integer of 4-7 is especially preferable.
Examples of the compound having the structure of the formula [3] include benzyl isothiocyanate, phenethyl isothiocyanate and the like, but benzyl isothiocyanate is relatively weak because of its irritating odor and relatively low fragrance. preferable.
In the formula [3], it is known that a compound having p of 2 or less is contained in aroma components such as wasabi and horseradish. It is appropriate to use synthesis.

A method for synthesizing the compound is disclosed, for example, in JP-A-2-221255, and the outline thereof is Ph— (CH ₂ ) _p —X (wherein p is as defined above) in an inert solvent. The ω-phenylalkyl thiocyanate having the same meaning and X having a halogen atom such as bromine, chlorine or iodine is reacted with thiocyanate, and the obtained ω-phenylalkyl thiocyanate is polar aprotic Obtained by isomerization in a solvent.

(2) Tea leaf extract Examples of tea leaves targeted for tea leaf extraction include green tea, oolong tea, black tea, and other Chinese teas such as yellow tea, blue tea, and black tea. Can be used as is. Also, two or more different types of tea leaves can be used in combination.
The tea leaf extract is obtained by immersing and extracting tea leaves in water and / or a polar organic solvent, filtering, concentrating under reduced pressure, and lyophilizing. The polar organic solvent for extraction is, for example, at least one organic solvent selected from the group consisting of methanol, ethanol, isopropanol, butanol, diethyl ether, ethyl acetate, and acetone, and may be a mixture of the solvent and water. Good. Among these, 50% ethanol is preferable from the viewpoint of price and safety. Moreover, although 2-24 hours are possible at room temperature-78 degreeC, 24 hours are preferable at room temperature.

(3) Plaque formation inhibitor composition The plaque formation inhibitor composition of the present invention contains the above-mentioned various isothiocyanate compounds and tea leaf extract, and preferably the isothiocyanate compound. Is dissolved in water and / or a polar organic solvent such as ethanol so that the concentration of the tea leaf extract is 0.01 to 1% by weight and the tea leaf extract is 0.1 to 10% by weight, and homogeneously mixed by stirring. Prepared. When using ethanol, 60 to 70% is preferable. In addition, even when using together 2 or more types of isothiocyanate compounds, or when using 2 or more types of tea leaves together, a density | concentration is in said each range.

(4) Application of plaque formation inhibitor composition The plaque formation inhibitor composition of the present invention can be applied by adding it to food or drink or oral hygiene.
The dosage form of the oral hygiene agent to be added may be any of a liquid agent, a solid agent and a semi-solid agent, and is applicable to a dentifrice, a troche, a liquid or powdered mouthwash, a coating liquid, a chewing gum and the like.
Moreover, soft drinks such as juice, and confectionery such as candy and chewing gum are suitable as foods and drinks to which the plaque formation inhibitor composition of the present invention is blended.
The plaque formation inhibitor composition of the present invention is preferably at a concentration of 0.01 to 5% by weight with respect to the final product (that is, the composition is diluted 20 to 10,000 times), particularly preferably at a concentration of 0.005. It is used by adding to a concentration of about 1 to 2% (ie diluted 50 to 1000 times). If the added amount is less than the lower limit amount, the plaque formation inhibitory effect is not exerted.On the other hand, if the added amount exceeds the upper limit amount, an astringent taste, wasabi-like irritating odor is felt. Not suitable for blending with sanitary agents.

  EXAMPLES Next, the present invention will be described more specifically with reference to examples. However, the present invention is not limited to these examples.

<A> Preparation of raw material of composition The raw material of the plaque formation inhibitor composition of the present invention was prepared as in Reference Examples 1 to 6 below.
[Reference Example 1] Synthesis of 4-pentenylisothiocyanate:
32 g of 4-pentenyl iodide was dissolved in 40 g of 1,3-dimethyl-2-imidazolidinone, 16 g of potassium thiocyanate and 5.5 g of calcium carbonate were added, and the mixture was heated and stirred at 75 ° C. for 1 hour.
Next, the temperature was raised to an internal temperature of 155 ° C., and the mixture was heated and stirred for 6 hours. After removing insolubles, extraction with methylene chloride yielded a crude oil. The crude oil was distilled under reduced pressure to obtain 4.2 g of 4-pentenyl isothiocyanate. The yield was 20% and the boiling point was 83 ° C./96 mmHg.

Reference Example 2 Synthesis of 5-methylthiopentyl isothiocyanate:
To a mixture of 38 g of 4-pentenyl isothiocyanate and 144 g of methyl mercaptan in methanol (30%), 0.9 g of azobisisobutyronitrile was added and stirred at room temperature for 9 hours. Ethyl acetate was added, washed with water, and distilled to obtain 33 g of 5-methylthiopentyl isothiocyanate. The yield was 63% and the boiling point was 101 to 103 ° C./1 mmHg.

Reference Example 3 Synthesis of 6-methylthiohexyl isothiocyanate:
To a mixture of 28 g of 5-hexenyl isothiocyanate and 50 g of a methyl mercaptan in methanol (30%), 0.4 g of t-butyl hydroperoxide (TBHP) was added and stirred at room temperature for 2 hours. Ethyl acetate was added, washed with water, and distilled to obtain 32 g of 6-methylthiohexyl isothiocyanate. The yield was 82% and the boiling point was 119 ° C./0.5 mmHg.

[Reference Example 4] Synthesis of benzylisothiocyanate:
17 g of bromobenzyl was dissolved in 40 g of 1,3-dimethyl-2-imidazolidinone, 10 g of potassium thiocyanate and 3.5 g of calcium carbonate were added, and the mixture was heated and stirred at 75 ° C. for 1 hour. Subsequently, the temperature was raised to an internal temperature of 155 ° C. and stirred for 6 hours. After removing insolubles, extraction with methylene chloride yielded a crude oil. The crude oil was distilled under reduced pressure to obtain 9.6 g of benzyl isothiocyanate. Yield 65%, boiling point 110 ° C./10 mmHg.

[Reference Example 5] Preparation of green tea extract:
A commercially available mixture of 40 g of dried green tea leaves and 0.8 kg of 50% aqueous ethanol was allowed to stand at room temperature for 24 hours. After filtration, it was concentrated under reduced pressure and freeze-dried to obtain 7 g of a green tea extract solid.

[Reference Example 6] Preparation of oolong tea extract:
A commercially available mixture of 70 g of dried oolong tea leaves and 1.5 kg of 50% aqueous ethanol was allowed to stand at room temperature for 24 hours. After filtration, the filtrate was concentrated under reduced pressure and freeze-dried to obtain 15 g of oolong tea extract solids.

[Reference Example 7] Preparation of black tea extract:
A commercially available mixture of 50 g of dried tea leaves and 1.0 kg of 50% aqueous ethanol was allowed to stand at room temperature for 24 hours. After filtration, it was concentrated under reduced pressure and freeze-dried to obtain 10 g of a black tea extract solid.

<B> Preparation of Plaque Formation Inhibitor Composition Using the raw materials prepared in each of the above reference examples, the plaque formation inhibitor compositions (Composition No. 1-4) were prepared.

[Test Example 1]
Next, using the plaque formation inhibitor compositions No. 1 to No. 4 of Reference Examples 1 to 7 and Examples 1 to 4, the plaque formation inhibitor composition of the present invention is an isothiocyanate compound alone. In addition, the following method (inhibition of glass smooth surface adhesion) is compared with how much the smooth surface adhesion exhibited by S. mutans is suppressed in a sucrose-containing cultured brain heart infusion (BHI) liquid medium as compared with the case of the tea leaf extract alone. Test).

S. mutans1 colonies were inoculated into 5 ml of BHI liquid medium and pre-cultured at 37 ° C. for 20 hours. Next, this was planted in a sucrose-containing BHI medium and adjusted so that the final viable cell count was 1.0 × 10 ⁶ CFU / ml.
An ethanol solution of the isothiocyanate compound and an ethanol solution of the tea leaf extract were added to each 1% of the bacterial culture medium, and the total amount was 5 ml and cultured in a test tube. The culture was performed at an elevation angle of about 30 degrees with respect to a horizontal plane at 37 ° C. for 24 hours.
After completion of the culture, the medium was removed, washed with distilled water, and infiltrated with 50% ethanol. Ethanol was removed and dried. Glucan adhering to the test tube was dissolved in 1N NaOH, neutralized, and colorimetrically determined by measuring the absorbance at 490 nm by the phenol sulfuric acid method.
The relative adhesion rate (%) was calculated according to the following formula when the glucan adhesion weight of the control to which no sample was added was 100%.

Relative adhesion rate (%) = S / C × 100
S: Glucan adhesion when the sample is added (absorbance at 490 nm)
C: Glucan adhesion amount of control (absorbance at 490 nm)

FIG. 1 shows the 50% inhibitory concentration of glucan when the green tea leaf extract (Reference Example 5), the oolong tea leaf extract (Reference Example 6) and the black tea leaf extract (Reference Example 7) are used alone. As a result, it was observed that the glucan adhesion 50% inhibitory concentration decreased in the order of green tea leaf extract, oolong tea leaf extract, and black tea leaf extract.
However, the astringency by the polyphenol contained in any of these extracts was strongly felt at this concentration.

  As shown in FIG. 2, the concentration of 4-pentenylisothiocyanate (Reference Example 1) when the plaque formation inhibitor composition No. 1 obtained in Example 1 showed 50% inhibition of glucan adhesion was 14 ppm. The concentration of the tea leaf extract (Reference Example 7) was 300 ppm, which was a case where the plaque formation inhibitor composition No. 1 was diluted 100 times.

  As shown in FIG. 3, the concentration of 5-methylthiopentyl isothiocyanate (Reference Example 2) when the plaque formation inhibitor composition No. 2 obtained in Example 2 showed 50% inhibition of glucan adhesion was 7 ppm, the concentration of the tea leaf extract (Reference Example 7) was 300 ppm, and this was the case when the plaque formation inhibitor composition No. 2 was diluted 100 times.

  As shown in FIG. 4, the concentration of 6-methylthiohexyl isothiocyanate (Reference Example 3) when the plaque formation inhibitor composition No. 3 obtained in Example 3 showed 50% inhibition of glucan adhesion was The concentration of the tea leaf extract (Reference Example 7) was 6 ppm, which was 300 ppm. This was the case where the plaque formation inhibitor composition No. 3 was diluted 100 times.

  As shown in FIG. 5, the concentration of benzyl isothiocyanate (Reference Example 4) when the plaque formation inhibitor composition No. 4 obtained in Example 4 showed 50% inhibition of glucan adhesion was 13 ppm, black tea The concentration of the leaf extract (Reference Example 7) was 300 ppm, which was a case where the plaque formation inhibitor composition No. 4 was diluted 100 times.

<C> Application of plaque formation inhibitor composition [Examples 5 to 8, Comparative Examples 1 to 5]
Candy Nos. 1 to 4 containing the plaque formation inhibitor compositions No. 1 to No. 4 of the present invention according to the formulation shown in Table 2, 4-pentenyl isothiocyanate (Reference Example 1), 5-methylthiopentyl Candy No. 5 containing isothiocyanate (Reference Example 2), 6-methylthiohexyl isothiocyanate (Reference Example 3), benzyl isothiocyanate (Reference Example 4), and tea leaf extract (Reference Example 7). 9 was obtained. These candy has sugar, starch syrup, organic acid, fragrance and water as common components, and is different only in the type of plaque formation inhibitor.

[Test Example 2]
The candy No. 1 to No. 9 were evaluated for flavor and taste by 10 professional panels. The evaluation results are shown in Table 3.

  From the above results, the plaque formation inhibitor compositions No. 1 to No. 4 of the present invention exhibit a synergistic effect when using the isothiocyanate compound and the tea leaf extract alone, respectively, and exhibit a plaque inhibiting effect. It was clarified that there was a sufficient effect when the amount added to the candy was below the lower limit where the flavor of each of the isothiocyanate compound and tea leaf extract was felt, and the original candy flavor and flavor were not impaired.

[Example 9] Tooth brushing:
The toothpaste which mix | blended dental plaque formation inhibitor composition No. 2 with the prescription of Table 4 was obtained.

[Example 10] Chewing gum:
The chewing gum which mix | blended dental plaque formation inhibitor composition No. 3 with the prescription of Table 5 was obtained.

[Example 11] Mouth cleaning agent:
By the formulation shown in Table 6, a mouth rinse containing the plaque formation inhibitor composition No. 4 of the present invention was obtained.

It is a graph which shows the glucan adhesion 50% inhibition density | concentration of each of the green tea leaf extract, oolong tea leaf extract, and black tea leaf extract obtained in Reference Examples 5-7. Plaque formation inhibitor composition No. 1, 4-pentenylisothiocyanate (Reference Example 1) and black tea leaf extract (Reference Example 7), which are components of the composition, each exhibit a 50% inhibitory concentration of glucan adhesion. It is a graph. Dental plaque formation inhibitor composition No. 2, 5-methylthiopentyl isothiocyanate (Reference Example 2) and tea leaf extract (Reference Example 7), which are components of the composition, each having 50% inhibitory concentration of glucan adhesion It is a graph to show. Dental plaque formation inhibitor composition No. 3, 6-methylthiohexyl isothiocyanate (reference example 3) and tea leaf extract (reference example 7), which are components of the composition, each having a 50% inhibitory concentration of glucan adhesion It is a graph to show. Plaque formation inhibitor composition No. 4, benzyl isothiocyanate (Reference Example 4) and black tea leaf extract (Reference Example 7), which are components of the composition, and graphs showing 50% inhibitory concentrations of glucan adhesion, respectively. is there.

Claims (6)

Ω-alkenyl isothiocyanate compound represented by the following formula [1], ω-alkylthioalkyl isothiocyanate compound represented by the following formula [2], and ω-phenylalkyl isothiocyanate represented by the following formula [3]. It contains one or two or more isothiocyanate compounds selected from the group consisting of an isocyanate compound and a tea leaf extract extracted from tea leaves using water and / or a polar organic solvent. Plaque formation inhibitor composition.
Equation _{(1): CH 2 = CH- (CH 2} ) m -NCS
(In the formula, m represents an integer of 2 to 10)
Formula [2]: RS— (CH ₂ ) _n —NCS
(In the formula, n represents an integer of 1 to 10, and R has 1 to 4 carbon atoms.
Represents an alkyl group)
Formula [3]: Ph- (CH ₂ ) _p -NCS
(In the formula, Ph represents a phenyl group, and p represents an integer of 1 to 10).   The plaque formation inhibitor composition according to claim 1, comprising 0.01 to 1% by weight of an isothiocyanate compound and 0.1 to 10% by weight of a tea leaf extract.   The plaque formation inhibitor composition according to claim 1, wherein the tea leaves are one or more tea leaves selected from the group consisting of green tea, black tea and oolong tea.   The isothiocyanate compound is one or more compounds selected from the group consisting of 4-pentenyl isothiocyanate, 6-methylthiohexyl isothiocyanate, 5-methylthiopentyl isothiocyanate, and benzyl isothiocyanate. The plaque formation inhibitor composition according to claim 1.   A food or drink or oral hygiene agent comprising the plaque formation inhibitor composition according to any one of claims 1 to 4.   A food or drink or oral hygiene agent comprising the plaque formation inhibitor composition according to any one of claims 1 to 4 at a concentration of 0.01 to 5% by weight.

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