JP4745948B2 - Food preservatives and food and drink - Google Patents

Description

  The present invention relates to a food preservative, and more particularly to a preservative having excellent antiseptic properties, characterized by containing a tyrosol derivative.

  A preservative is usually added to foods for the purpose of preventing deterioration of quality due to microorganisms. As such preservatives, synthetic preservatives such as benzoic acid (sodium salt), sorbic acid, parahydroxybenzoic acid ester, sodium propionate, and calcium propionate are known. Such synthetic preservatives generally tend not to be used, and safer preservatives are required, and various preservatives have been reported (see, for example, Patent Documents 1 to 6). However, preservatives derived from natural products are not always satisfactory in terms of antiseptic power, stability, production cost, stable supply, and the like. In some cases, the preservative composition itself has a unique fragrance, and particularly when applied to foods and the like, there are difficulties such as impairing the palatability of foods.

  Tyrosol is a kind of phenylethanoid and is produced from tyrosine by the action of yeast during alcoholic fermentation. For example, it is contained as one of bitter components in sake and olive fruits. Furthermore, it is reported that the tyrosol derivative is contained in olive fruit although it is in a trace amount (Non-patent Document 7). Although a specific tyrosol derivative has already been found to have a lipolytic effect (Patent Document 1), no investigation or report has been made on the antiseptic effect of food.

JP 2006-169192 A Taisho Technos Research Report on Food Safety Improvement Microorganisms, Food Allergies, Toxins, Other Food Safety Improvement Technology Development Project 1999 (Ministry of Health and Welfare) Page 9,11-15,1999 Rie Katsumata, Ikue Yoshida, Noriko Tsujikawa, Yoshiko Muramatsu, Miki Kiuchi (Kyoritsu Women's Univ.) Yutaka Tsumugi (Aohata Fruit Processing), Kenji Tanaka (National Food Research Institute) 2003 Keiji Sugawara (Nichiro Central Research Institute), Erika Nemoto (Asama Kasei) Monthly Food Chemical Vol.22, No.4, Pages 24-32, 2006 INATSU Yasuhiro, KAWASAKI Susumu, KAWAMOTO Shinichi (Natl. Food Res. Inst., Tsukuba, JPN) J. Food Sci, Vol. 70, No. 9, Page M393-M397, 2005 Fukushi Hideaki Food Industry Vol.45, No.4, Page27-34,2002 Shoji Yamamoto (Maruzen Pharmaceutical) Food Industry Vol.45, No.4, Page35-41,2002 F. Gutierrez-Rosales et al. J. Agric. Food Chem., 2003, 51, 6021-6025

Under such circumstances, the present invention has been made to solve the above-mentioned problems, has high storage stability, does not adversely affect the physical properties, color, fragrance, etc. of food and does not impair the palatability of food, etc. An object is to provide a preservative composition.

  As a result of intensive studies in view of the above circumstances, the present inventors have completed the present invention because the tyrosol derivative has a strong antiseptic property, and even if the composition is used in food, the flavor and taste are not impaired. It came to.

That is, this invention exists in the food-drinks containing the preservative for foods containing the tyrosol derivative shown by following General formula (1), and the said food preservative.
(In the formula, R is an acyl group having 2 to 10 carbon atoms.)

  The preservative characterized by containing the tyrosol derivative of the present invention has an antibacterial activity against bacteria, yeast, and sputum, and thus has excellent antiseptic power. When blended in foods and drinks, pharmaceuticals, cosmetics, etc., it can effectively prevent corruption. In addition, the preservative does not have a flavor and does not impair the palatability even when used for food and drink.

  Hereinafter, embodiments of the present invention will be described in detail. The tyrosol derivative used in the present invention is a compound represented by the above general formula (1), where R is an acyl group having 2 to 10 carbon atoms, and has an unsaturated bond inside the acyl group, there is no problem. You may have a ring. Moreover, you may have functional groups, such as an amino group. Specific examples include acetyl, propionyl, butyryl, isobutyryl, valeryl, hexanoyl, lauroyl, palmitoyl, oleoyl and the like. From the viewpoint of maintaining the effect, acetyl is desirable.

  Tyrosol derivatives are components contained in the fruit of Olea europaea, which can be prepared from natural products, but can be obtained using a known method for acylation of phenolic compounds. You can also. For example, it can be easily obtained by reacting 2- (4-hydroxyphenyl) ethyl alcohol and acid chloride in pyridine.

In addition to the tyrosol derivative, the preservative composition of the present invention includes shirako protein extract, ε-polylysine, pectin degradation product, honoki extract, tsuyaprisin, udo, as long as the excellent effects of the present invention are not impaired. Preservatives derived from natural products such as extracts, peony extracts, citrus extracts, enzymatically decomposed pearl extract, forsythia extract, benzoic acid (sodium salt), sorbic acid, parahydroxybenzoic acid ester, sodium propionate, calcium propionate It is also possible to contain known preservatives such as synthetic preservatives.

  The preservative composition containing the tyrosol derivative of the present invention can be used by adding it to ordinary foods such as pharmaceuticals, quasi drugs, and health foods. The dosage form of the food is not particularly limited and can be various. Specifically, tablets, pills, dragees, powders, granules, teas, tea bags, hard capsules, soft capsules, candy It is possible to make various things such as ice, baked confectionery, and beverages.

  The addition ratio of the preservative composition of the present invention to foods varies widely depending on the purpose and target and cannot be defined unconditionally, but generally, it is 0.00001-1 based on the total amount of food. It is added so that it may become 0.00 mass%, Preferably it is 0.001-0.5 mass%.

  EXAMPLES Hereinafter, although this invention is explained in full detail with an Example, this invention is not limited by these. Hereinafter, unless otherwise specified,% means mass%.

Test example 1
The antimicrobial activity test results of monoacetyltyrosol against various microorganisms are shown.
Test species Aspergillus niger ATCC 16404
Bacillus subtilis ATCC6633
Staphylococcus aureus ATCC 6538
Escherichia coli ATCC 8739

The test bacteria cultured by the method shown in the Japanese Pharmacopoeia was dispersed in 0.1% peptone saline to prepare a bacterial solution containing about 10 ⁶ cells / mL viable bacteria or spores. Next, monoacetyltyrosol was dissolved in dimethyl sulfoxide (hereinafter referred to as DMSO) to prepare a sample. The prepared bacterial solution is streaked on a plate agar medium in which 5% sample and 1.5% agar are added to the medium used for culturing the test bacteria, and stored at the optimum temperature for each bacterial species. It was measured.

Species growth inhibition concentration (%)
Aspergillus niger 0.125
Bacillus subtilis 0.5
Staphylococcus aureus 0.5
Escherichia coli 0.25

  As is clear from Test Example 1, the tyrosol derivative according to the present invention has antibacterial activity against bacteria, yeast, and sputum, and thus has excellent antiseptic power and is useful for foods, pharmaceuticals, quasi drugs, and the like. When the derivative is added in an amount of 0.01 to 1%, desirably 0.05% or more, it is possible to effectively prevent spoilage. Moreover, even if this derivative does not have flavor and is used for food-drinks, it does not impair the palatability.

Production Example 1 (Production of monoacetyltyrosol)
Tyrosol (5.0 g) was placed in a 200 mL eggplant-shaped flask, 100 mL of anhydrous ether was added, and the mixture was stirred under ice cooling. Further, 1.0 mL of pyridine and 4.0 g of acetyl chloride were sequentially added, and after 4 hours, post-treatment was performed according to a conventional method to obtain 4.3 g of a crude product.
The obtained product was fractionated by silica gel chromatography (mobile phase: ethyl acetate / n-hexane (1: 4)) using silica gel 60N (100-210 μm) manufactured by Kanto Chemical Co., Ltd., and 4.2 g of monoacetyltyrosol was obtained. Got.

Example 1 (preserving power against boiled noodles)
In accordance with the following method, the preservative power of monoacetyltyrosol was measured.
Add the chemicals shown in Table 1 to the basic composition of 100 g of weak flour and 30 g of 9% saline, mix well, then use a small noodle making machine to make fine noodles as usual, boil in boiling water for 10 minutes, Water cooled. After draining water, it put into the plastic bag with a chuck | zipper, and preserve | saved at 15 degreeC, The external appearance change and the viable count of noodles were measured. Boiled noodles are considered to be ineligible for 105 ⁵ g / g or more according to food norm instruction standards, so the number of storage days that reached the ineligibility criteria was compared with boiled noodles with no chemicals.

  As shown below, the tyrosol derivative of the present invention improved storage stability and extended the edible period. In the taste and color, the test group of the present invention showed no difference from the control.

Samples that meet the ineligibility criteria Storage period test area 0.1% monoacetyltyrosol added noodles> 6
Noodles with 0.05% monoacetyltyrosol 6
Noodles with 0.01% monoacetyltyrosol 4
Control group No additive noodles 3

Example 2 (Anti-preservative power against consomme soap)
To 5 mL of consomme soup, 5 mL of an aqueous solution of monoacetyltyrosol was added and mixed, and 0.1 mL of the bacterial solution was inoculated, cultured at 25 ° C., and the number of viable bacteria was measured over time. Inoculum may disperse the test strain cultured in the method shown in the Japanese Pharmacopoeia 0.1% peptone saline to prepare a bacterial solution containing viable cell count of approximately ¹⁰⁴ cells / mL.
Staphylococcus aureus ATCC 6538 and Escherichia coli ATCC 8739 were used as the inoculated bacterial species.

As shown in FIG. 1, a control and a consomme soup drug additive-free inoculated with Eschrichia coli or Staphylococcus aureus whereas reach more than 10 ⁶ cells / mL in 24 hours, the addition of 0.5% monoacetyl Ciro sole, Each inoculum was not detected, and a preservation effect was observed.

The preservative composition containing the tyrosol derivative according to the present invention has an excellent antiseptic ability, does not have a specific aroma and flavor, and can be blended in various foods without affecting the flavor and color. It is. In general, the number of viable bacteria at the edible limit of a food is said to be 10 ⁷ / g. However, the storability increases, so that the edible period becomes longer and the shelf life of the food can be extended.

It is a figure which shows the growth inhibitory effect of monoacetyltyrosol with respect to Escherichia coli or Staphylococcus aureus in a consomme soup.

Claims (1)

A food preservative comprising a tyrosol derivative represented by the following general formula (1):

(In the formula, R is an acetyl group or a propionyl group)