JPH0360802B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention exhibits an excellent inhibiting effect on the growth of oral microorganisms, represented by Streptococcus mutans, which are significantly involved in the formation of dental caries. The present invention relates to an anti-caries agent that can prevent the formation of dental plaque associated with dental caries and is useful for preventing dental caries. The anti-caries agent can be used in toothpastes, lozenges, mouthwashes,
The present invention relates to an anti-caries agent which can be incorporated into oral compositions such as chewing gums and mouth fresheners. More specifically, the present invention relates to 4-tert-butylcyclohexanol, ethyl-n-amylketone, pulegone, ethylvinylketone, methylheptenone, cyclotene, anisylacetone, p-methyl-acetophenone, diasmone, acetylmethylcarbinol, acetylacetic acid. Ethyl, ethyl lactate, diethyl malonate, cis-3-hexenol acetate, ethyl levulinate, terpinyl acetate, ethyl β-methylphenylglycidate, styralyl acetate, benzyl isothiocyanate, β-
Methylthiopropionate, isovaleric acid, pyruvic acid, 2-methylbutyric acid, cinnamic acid, phenylacetic acid, linalool oxide, phenylacetaldehyde dimethyl acetal, propylene glycol acetal of ethyl acetylacetate, 4-ethylguaiacol, isoeugenol, catechol and The present invention relates to an anti-caries agent containing as an active ingredient at least one compound selected from the group consisting of 5-hydroxymethylfurfural. It is said that tooth decay (caries) occurs only when three conditions are present: oral microorganisms, dental plaque, food ingredients, especially sugar, and tooth structure. The incidence of cavities in teeth is high from the age of 3 years, and the incidence of caries in baby teeth in 3-year-old children is already 90%.
It is said that it can reach up to %. Dental plaque is formed on the tooth surface by oral bacteria, food residue, and salivary organic matter. One type of oral bacteria, Streptococcus miutans, synthesizes dextran-like polysaccharides from sucrose.
It promotes the formation of dental plaque, and also contains sugar, sugar, etc.
It is known that cavities occur by producing acids from other sugars and retaining them in dental plaque, causing demineralization of the teeth. Therefore, suppressing the growth of oral bacteria such as Streptococcus miutans and inhibiting the formation of dental plaque is an effective means of preventing the occurrence of dental caries. Methods for inhibiting the formation of such dental plaque include a method of inhibiting the growth of oral bacteria by incorporating a bactericide such as chlorhexidine into an oral preparation, or a method of inhibiting the growth of oral bacteria by adding a polysaccharide-degrading enzyme such as dextrase to the oral cavity. There is a known method for preventing the formation of dental plaque by incorporating it into dental preparations. The present inventors investigated various methods for inhibiting the proliferation of Streptococcus miutans, an oral bacterium that is largely involved in the formation of dental plaque that causes dental caries. The following 4-ter-butylcyclohexanol, which was not known to have an inhibitory effect on typical oral microorganisms involved in caries formation,
Ethyl-n-amyl ketone, pulegone, ethyl vinyl ketone, methylheptenone, cyclotene, anisylacetone, p-methyl-acetophenone,
Diasmone, acetylmethyl carbinol, ethyl acetate, ethyl lactate, diethyl malonate, cis-3-hexenol acetate, ethyl levulinate, terpinyl acetate, ethyl β-methylphenylglycidate, styralyl acetate, benzyl isothiocyanate , methyl β-methylthiopropionate, isovaleric acid, pyruvic acid, 2-methylbutyric acid, cinnamic acid, phenylacetic acid, linalool oxide, phenylacetaldehyde dimethyl acetal, propylene glycol acetal of ethyl acetate, 4-ethylguaiacol, isoeugenol discovered that a compound selected from the group consisting of catechol and 5-hydroxymethylfurfural is highly effective in suppressing the proliferation of Streptococcus miutans, inhibiting plaque formation, and preventing dental caries. , we have completed the present invention. Furthermore, at least one selected from the above compound group
It was learned that the seeds are useful as an anti-caries agent that effectively prevents tooth decay and leaves a pleasant scent in the oral cavity. Therefore, an object of the present invention is to provide an excellent anti-caries agent. The above objects and many other objects and advantages of the present invention will become more apparent from the following description. Oral compositions suitable for incorporating the anti-caries agent of the present invention include, for example, toothpastes such as toothpaste, powdered toothpaste, and liquid toothpaste, troches, mouthwashes,
Examples include solid mouth fresheners, liquid mouth fresheners, chewing gum, and liniments. The active ingredient used in the anti-caries agent of the present invention can be incorporated in an amount of, for example, about 0.001 to about 5% by weight, particularly preferably about 0.1 to about 2%, based on the oral composition. Other compounding materials of the oral composition can be selected as appropriate depending on the type of preparation, but for example, in the case of toothpaste, the second
Abrasives such as calcium phosphate, calcium carbonate, calcium pyrophosphate, insoluble sodium metaphosphate, anhydrous silicic acid, magnesium carbonate and aluminum hydroxide; sodium lauryl sulfate, sodium lauroyl sarcosinate, sodium coconut monoglyceride sulfate, sodium coconut monoglyceride Foaming agents such as sulfonates and sucrose fatty acid esters; glycerin, sorbitol,
Wetting agents such as propylene glycol; binders such as tragacanth gum, karaya gum, iris moss, methyl cellulose, carboxymethyl cellulose; peppermint oil, spearmint oil, menthol, anethole, wintergreen, cinnamon, clove, vanilla, katsushi and other spices and fruit flavors, etc. flavoring agents; sweeteners such as saccharin, glycyrrhizin, stevioside, neohesperidin dihydrochalcone; and preservatives. In the present invention, a toothpaste can be produced by mixing the above-mentioned active ingredients with water together with these materials and using a conventional method. In the case of troches, mouthwashes, chewing gum, mouth fresheners, etc., the compounding materials can be appropriately selected depending on the properties required for each product. In the present invention, in addition to at least one compound selected from the above group, active ingredients of the oral composition include, for example, dentine sodium monofluorophosphate, stannous fluoride, and sodium fluoride. Fortifying agents; bactericidal agents such as chlorhexidine; dihydrocholesterin, epidihydrocholesterin,
Anti-inflammatory agents such as allantoin and its derivatives, epsilon aminocaproic acid and tranexam;
Tissue activators such as hinokitiol and sodium copper chlorophyllin; lysozyme and salt can also be blended. According to one aspect of the invention, the oral composition contains 4-
ter-butylcyclohexanol, ethyl-n-
amyl ketone, pulegone, ethyl vinyl ketone,
Methylheptenone, cyclotene, anisylacetone, p-methyl-acetophenone, diasmone,
Acetyl methyl carbinol, ethyl acetate, ethyl lactate, diethyl malonate, cis-3-
Hexenol acetate, ethyl levulinate, terpinyl acetate, ethyl β-methylphenylglycidate, styralyl acetate, benzyl isothiocyanate, methyl β-methylthiopropionate,
Isovaleric acid, pyruvic acid, 2-methylbutyric acid, cinnamic acid, phenylacetic acid, linalool oxide, phenylacetaldehyde dimethyl acetal, propylene glycol acetal of ethyl acetate, 4-ethylguaiacol, isoeugenol, catechol and 5-hydroxymethylfurfural By adding at least one compound selected from the group consisting of the following, it is possible to provide a composition that suppresses the growth of Streptococcus miutans, which is a type of oral bacteria, and can effectively prevent dental caries. Some embodiments of the present invention will be explained in more detail below with reference to Examples. Example 1 Peptone 1%, yeast extract 0.5%, sucrose 2%
Prepare an agar medium with a pH of 7.0, sterilize it, cool it, and add it to it.
0.5% of the culture solution of Streptococcus mutans IID973 (E49) strain cultured for 24 hours was added and immediately dispensed into sterile 80 mm diameter petals in 12 ml portions. Next, a paper disk with a diameter of 8 mm was impregnated with the sample compound, placed on the center of the above-mentioned Schare's agar medium, and cultured at 30°C for 3 days. When Streptococcus miutans grows, the agar medium becomes cloudy, but the area around the vapor disk where bacterial growth is inhibited still remains transparent, so this clear zone (hereinafter referred to as the inhibition circle diameter) was measured to evaluate antibacterial properties. Table 1 shows compounds that had an inhibition circle diameter of 40 mm or more and had a significant growth inhibiting effect on Streptococcus miutans and their results.

【table】

[Table] All of the compounds listed in Table 1 above had an excellent antiproliferative effect on Streptococcus miutans, but in particular, isovaleric acid, 2-methylbutyric acid, and salicylaldehyde completely inhibited the growth of Streptococcus miutans. suppresses the proliferation of Streptococcus miutans,
It showed extremely remarkable effects. Example 2 0.02% of the sample compound was added to a heart infusion broth liquid medium supplemented with 2% sucrose, and 0.5% of the precultured culture of Streptococcus miutans IID973 (E49) was added to the liquid medium.
% and cultured anaerobically at 37°C for 24 hours. Next, the culture solution was treated with a mixer to disperse the precipitate, and the absorbance (turbidity) at 550 nm was measured.
The amount of plaque formed by Streptococcus miutans was measured. The results are shown in Table 2. The amount of plaque formed is expressed as a percentage when the control (no sample compound added) is taken as 100%.
At the same time, the pH of the culture solution was measured and used as a measure of acid production.

[Table] As is clear from the results in Table 2, the compound according to the present invention inhibited the growth of Streptococcus miutans, and no acid production was observed. By incorporating these compounds into oral compositions, the occurrence of tooth decay (caries) can be effectively prevented.

Claims (1)

[Claims] 1 4-ter-butylcyclohexanol, ethyl-n-amylketone, pulegone, ethylvinylketone, methylheptenone, cyclotene, anisylacetone, p-methyl-acetophenone, diasmone, acetylmethylcarbinol, ethyl acetate, ethyl lactate, malon diethyl acid, cis-3-hexenol acetate, ethyl levulinate, terpinyl acetate, ethyl β-methylphenylglycidate, styralyl acetate, benzyl isothiocyanate, methyl β-methylthiopropionate, isovaleric acid, pyruvic acid, Compounds selected from the group consisting of 2-methylbutyric acid, cinnamic acid, phenylacetic acid, linalool oxide, phenylacetaldehyde dimethyl acetal, propylene glycol acetal of ethyl acetate, 4-ethylguaiacol, isoeugenol, catechol and 5-hydroxymethylfurfural An anti-caries agent characterized by containing at least one of the following as an active ingredient.