JPS598242B2 - Biseibutsuyokuseizai - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel microbial inhibitors for foods or other materials.

In general, the adverse effects of microorganisms on foods or other materials, such as cosmetics and paints, are extremely significant, and for this reason, it is necessary to prevent the loss of large amounts of valuable resources from the standpoint of resource conservation.

Theoretically, maintaining sterile conditions is the correct way to prevent this, but this requires a huge amount of equipment and thorough management, and considering the materials and labor required, this method is extremely impractical. It is.

Therefore, preventing the harmful effects of microorganisms by simple methods using fungicides and fungicides is realistically the most preferable method.
It is the law. However, conventional bactericidal and fungicidal agents, that is, microbial inhibitors, have many drawbacks such as variability in effectiveness and toxicity.

For example, zorpic acid's effectiveness varies by 20% depending on pH fluctuations.
%, and therefore it is only practical to use it under optimal conditions. Furthermore, nitrofuran derivatives, particularly freelfuramide, which are most effective as food preservatives, are highly toxic and are useful only when added in extremely small amounts. Although pentachlorphenol and the like are effective as antifungal agents for paints and the like, they are not preferred because they are highly toxic and have a large residual accumulation potential, causing environmental pollution. The present invention is directed to providing useful compounds that overcome the drawbacks of the conventional products mentioned above.

That is, the present invention provides a microbial inhibitor containing a compound having a 2.7 octadienyl group represented by the following general formula as an active ingredient. -CH-CH2)n-Y > In the case of CH-0H, n-2 is shown.

Note that R: represents an ethylene group or a propylene group.

Incidentally, typical examples of compounds having the general formula structure related to the present invention are as follows.

The compound (1) is produced by reacting butadiene in the presence of ethylene glycol at a temperature ranging from room temperature to 120° C. using a palladium-based catalyst having a phosphine as a ligand.

Compound (2) can also be obtained by using glycerin instead of ethylene glycol under the same conditions. Therefore, other similar compounds can also be produced by changing the type of polyol. Compound (3) is produced by reacting with butadiene in the presence of carbon monoxide and a secondary or tertiary alcohol using a similar catalyst system containing a palladium-based catalyst and a phosphine as a ligand.
Nonadienoic acid ester is synthesized. It can be easily produced by hydrolyzing it with an alkali. Compound (4) uses a similar catalyst system and converts butadiene into carbon dioxide gas.
It is produced by reaction in the presence of water. Although these reaction systems can be carried out in either a solvent system or an emulsion/aqueous system, it is more advantageous to use an emulsion/aqueous system in order to separate the reactants. In the case of a mono-aqueous emulsion, the reaction proceeds advantageously by using a water-soluble phosphine (for example, sodium diphenylphosphoundecanoate) as a ligand. 2 according to the present invention obtained by each of the above methods.
The acute toxicity of compounds with a 7-octadienyl group is
It shows LD5O7y/Kg or higher when administered orally to mice, which is similar to that of zorpic acid, and in addition, there is little variation in effects due to pH.

Therefore, 1 is used for foods such as fruit juice and dairy products, cosmetics, and paints.
It was confirmed that adding 1/500 to 1/2000 gave excellent effects. Examples will be described below, but the present invention is not limited only to these examples.

Example 1 As a compound having a 2,7-octadienyl group according to the present invention, 2-(2,7-octadienoxy)ethanol,
50% glycerin aqueous solutions of 1,3-di(2,7-octadienoxy)-2-propanol, 3,8-nonadienoic acid, 2,7-octadienol, and zorpic acid were each prepared as a control.

Next, Escherichia coli (Escherichia coli) was used as a test bacterium.
ll), Staphylococcus aureus (StaphylOcOccu
sAureus), Bacillus subtilis
ilis), baker's yeast (Sacchar Omycesc
erevisiae), black mold (Aspergillus
sniger), blue mold (Penicilliumch)
rysOgenum) was selected as an ordinary agar medium PH7. O. As a medium for yeast mold, potato grape sugar agar medium PH7. O, and the sample concentration in the medium is 1000, 500) 250) 125, 62
．． An agar plate was prepared so that the concentration was 5.0 μV/ml. Next, each of the above-mentioned bacteria was inoculated into these, and the bacteria were cultured at 37°C for 2 days, and the yeast and molds were cultured at 25°C for 5 days, and the presence or absence of growth was observed. The results of this test are shown in Table 1.

As is clear from the above table, each compound according to the present invention was shown to have antibacterial properties equal to or greater than that of zorpic acid.

In particular, 2,7-octadienoxyethanol was found to have an antibacterial effect on Escherichia coli, Staphylococcus aureus, black mold, blue mold, etc., and its antibacterial spectrum was confirmed to be wide. Also 1.
3-G(2.7-octadienoxy)propanol exhibits specific inhibitory power against Gram-positive bacteria such as Staphylococcus aureus, and the fact that it shows less than 62.5 μy/ml is a surprising effect. I don't get it. 3,8-nonadienoic acid, 2,7-octadienol was found to be more effective against molds than the control zorpic acid.

Example 2 Vanishing cream (stearic acid 12.0) Bees wax 4.0, Liquid paraffin 6.0, Surfactant 4.0.
0.2% of each compound used in Example 1 was added to 0.0 parts of lanolin, 1.0 parts of lanolin, 5.0 parts of glycerin, 0.3 parts of triethanolamine, and 67.7 parts of water, and inoculated with blue mold.
It was left at 27°C for one month.

No mold growth was observed in the samples to which the compound of the present invention was added, but vigorous mold growth was observed in the samples without additives. Example 3 0.1% of each compound used in Example 1 was added to water-based paint (manufactured by Nippon Paint Co., Ltd., vinyl acetate resin emulsion), and this was applied to a waterproof veneer plywood of 20Cd and 0.9mm thick. The samples were then left in a constant temperature room at 27°C and 80% humidity to check for mold growth.

With the additive-free product, mold began to grow after about one month, and after three months, nearly 90% of the entire surface was covered with mold, but no mold was observed with the additive of the present invention. Example 4 A mandarin orange juice was prepared by diluting the juice of Satsuma mandarin oranges, adding 10% sugar to the diluted juice, and heat-treating the mixture at 80° C. for 10 minutes.

Claims (1)

[Scope of Claims] 1. A microbial inhibitor characterized by containing as an active ingredient a compound having a 2,7-octadienyl group represented by the following general formula. (CH_2=CH-(CH_2)_3CH=CH-CH
_2) _n-Y However, Y: -OH, -COOH, -ORO
In the case of H, n=1 Y: ▲ There are mathematical formulas, chemical formulas, tables, etc. In the case of ▼, n = 2 In addition, R: Indicates ethylene group, propylene group.