Composition and starting material composition of cosmetic

Abstract

Provided is a composition capable of appropriately exhibiting an virus proliferation inhibition effect. This composition is characterized by containing at least (2R,3R)-2,3-butanediol and / or (2S,3S)-2,3-butanediol and (meso)-2,3-butanediol, wherein the weight-based proportion of the content of the (meso)-2,3-butanediol is not more than twice the total content of the (2R,3R)-2,3-butanediol and the (2S,3S)-2,3-butanediol.

Description

Composition and cosmetic raw material composition

[0001] The present invention relates to a composition and a cosmetic raw material composition.

[0002] 2,3-Butanediol (hereinafter also referred to as "2,3-BDO") is used, for example, as an antifreeze, and as a raw material for methyl ethyl ketone and 1,3-butadiene, which are produced by dehydration. 2,3-BDO can also be used to produce methanol (22081 kJ kg －１ ) and ethanol (29055 kJ.kg －１ ) equivalent to a calorific value of 27,198 kJ. kg －１ It is a chemical with important potential industrial uses as a liquid fuel for pharmaceuticals. Other potential uses include the manufacture of printing inks, perfumes, cosmetic ingredients, fumigants, moisturizers and softeners, explosives and plasticizers, and as a carrier for pharmaceuticals.

[0003] Furthermore, in recent years, research has been conducted into the application of 2,3-BDO as an antibacterial and antiviral agent, and Patent Document 1 discloses an antiviral composition comprising 2,3-butanediol and an acid. This document discloses that 2,3-butanediol itself is an alcohol that cannot inactivate viruses. Furthermore, Patent Document 2 discloses an antibacterial agent comprising (meso)-2,3-butanediol, but does not mention its antiviral activity. Patent Documents 1 and 2 and Non-Patent Document 1 are all incorporated herein by reference.

[0004] Special table No. 2018-531991 Special table No. 2017-531671

[0005] Bulletin of the Central Customs Laboratory, No. 20, 1980, pp. 123-127

[0006] Thus, 2,3-BDO has not previously been recognized as having antiviral activity, and its use as a drug for inhibiting viral proliferation has not been considered at all. An object of the present invention is to provide a composition that can appropriately exert a viral proliferation inhibitory effect in applications where 2,3-BDO is required to have such an effect.

[0007] The present inventors have conducted extensive research into why 2,3-BDO does not exhibit the viral proliferation inhibitory effect mentioned in Patent Document 1, and as a result have newly discovered that there is a correlation between the abundance ratio of optical isomers of 2,3-BDO and the viral inhibitory effect.

[0008] Generally, chemically synthesized products of 2,3-BDO contain three optical isomers: (2R,3R)-2,3-butanediol, (2S,3S)-2,3-butanediol, and (meso)-2,3-butanediol. Figure 2 is a gas chromatography chart showing the proportions of the optical isomers of 2,3-BDO in Non-Patent Document 1. As shown in FIG. 2, a typical chemically synthesized product of 2,3-BDO contains the optical isomers in a weight ratio of (2R,3R)-2,3-butanediol: (2S,3S)-2,3-butanediol: (meso)-2,3-butanediol = 1:1:4.25 (the peak at around 14 minutes is a peak containing both (2R,3R)-2,3-butanediol and (2S,3S)-2,3-butanediol (indicated by the initial letter r for the racemate in FIG. 2), and the peak at around 16 minutes is the peak for (meso)-2,3-butanediol (indicated by m in FIG. 2)).

[0009] The inventors have discovered that, among these, (meso)-2,3-butanediol promotes viral growth, while (2R,3R)-2,3-butanediol and (2S,3S)-2,3-butanediol inhibit viral growth. The reason why typical chemically synthesized 2,3-BDO products are not recognized to have antiviral activity is thought to be because, in such chemically synthesized 2,3-BDO products, (meso)-2,3-butanediol, which promotes viral growth, and (2R,3R)-2,3-butanediol and (2S,3S)-2,3-butanediol, which inhibit viral growth, coexist, and as a result of these antagonistic interactions, the product is observed to have almost no antiviral activity.

[0010] In this specification, the "viral proliferation inhibitory effect" means that if administering the subject composition reduces the viral proliferation ability compared to administering water, the subject composition is determined to have a viral proliferation inhibitory effect.

[0011] The present inventors discovered that viral proliferation can be sufficiently inhibited by adjusting the weight ratios of (meso)-2,3-butanediol, (2R,3R)-2,3-butanediol, and (2S,3S)-2,3-butanediol, and arrived at the present invention. That is, the composition of the present invention is characterized by comprising at least (2R,3R)-2,3-butanediol and / or (2S,3S)-2,3-butanediol, and (meso)-2,3-butanediol, and the content of the (meso)-2,3-butanediol is not more than twice the total content of the (2R,3R)-2,3-butanediol and the (2S,3S)-2,3-butanediol, by weight. In terms of weight ratio, the content of the (meso)-2,3-butanediol is more preferably 1.5 times or less, even more preferably 0.5 times or less, still more preferably 0.13 times or less, and particularly preferably 0.05 times or less, the total content of the (2R,3R)-2,3-butanediol and the (2S,3S)-2,3-butanediol.

[0012] When the optical isomers of 2,3-BDO in the composition are in the above ratio, the viral proliferation inhibitory effect is suitably exhibited.

[0013] The composition of the present invention preferably contains the (2S,3S)-2,3-butanediol, and the content of the (2S,3S)-2,3-butanediol is greater than the content of the (meso)-2,3-butanediol. The composition of the present invention preferably contains the (2R,3R)-2,3-butanediol, and the content of the (2R,3R)-2,3-butanediol is greater than the content of the (meso)-2,3-butanediol. When the optical isomers of 2,3-BDO in the composition are in the above-mentioned ratio, the viral proliferation inhibitory effect is more suitably exhibited.

[0014] The composition of the present invention preferably contains both the (2S,3S)-2,3-butanediol and the (2R,3R)-2,3-butanediol, and the content of the (2S,3S)-2,3-butanediol is greater than the content of the (2R,3R)-2,3-butanediol and is also greater than the content of the (meso)-2,3-butanediol. Comparing (2S,3S)-2,3-butanediol and (2R,3R)-2,3-butanediol, (2S,3S)-2,3-butanediol exhibits a stronger viral growth inhibitory effect. Therefore, when the content of (2S,3S)-2,3-butanediol is within the above range, the viral growth inhibitory effect is more suitably exhibited.

[0015] The composition of the present invention contains both the (2S,3S)-2,3-butanediol and the (2R,3R)-2,3-butanediol, and the content of the (2R,3R)-2,3-butanediol may be greater than the content of the (2S,3S)-2,3-butanediol and greater than the content of the (meso)-2,3-butanediol. Comparing (2S,3S)-2,3-butanediol and (2R,3R)-2,3-butanediol, (2R,3R)-2,3-butanediol is colorless and transparent, while (2S,3S)-2,3-butanediol is slightly yellow. Therefore, from the viewpoint of the degree of freedom in adjusting color, it is preferable that the content of (2R,3R)-2,3-butanediol in the composition of the present invention is higher than the content of (2S,3S)-2,3-butanediol.

[0016] The composition of the present invention may not contain (2S,3S)-2,3-butanediol. As described above, (2R,3R)-2,3-butanediol is colorless and transparent, while (2S,3S)-2,3-butanediol is slightly yellow. Therefore, from the viewpoint of the degree of freedom in color adjustment, it is preferable that the composition of the present invention does not contain (2S,3S)-2,3-butanediol. Note that the composition of the present invention can inhibit viral proliferation even if it does not contain (2S,3S)-2,3-butanediol. Furthermore, as used herein, "the composition does not contain (2S,3S)-2,3-butanediol" means that when the composition is subjected to GC-MS analysis under the above conditions, no peak with an S / N ratio of 3 or greater is present at the position where (2S,3S)-2,3-butanediol is detected (around 12.8 minutes in each Example and Comparative Example). The position where (2S,3S)-2,3-butanediol is detected can be determined using a standard sample.

[0017] The composition of the present invention preferably does not contain racemates of (2R,3R)-2,3-butanediol and (2S,3S)-2,3-butanediol, because the antiviral functions of (2R,3R)-2,3-butanediol and (2S,3S)-2,3-butanediol tend to be reduced.

[0018] The composition of the present invention is preferably used as a virus growth inhibitor. As described above, the composition of the present invention exhibits a virus growth inhibitory effect. Therefore, the composition of the present invention is suitable as a virus growth inhibitor.

[0019] The cosmetic raw material composition of the present invention is characterized by containing the above-mentioned composition of the present invention. As described above, the composition of the present invention exhibits a virus proliferation inhibitory effect. Therefore, when a cosmetic is produced from the cosmetic raw material composition containing the composition of the present invention, the cosmetic exhibits a virus inhibitory effect.

[0020] According to the present invention, a composition capable of appropriately exhibiting the effect of inhibiting viral proliferation can be provided.

[0021] Fig. 1 is a chart showing the results of GC-MS analysis of the composition of Example 5. Fig. 2 is a gas chromatography chart showing the proportions of optical isomers of 2,3-BDO in Non-Patent Document 1.

[0022] (Detailed Description of the Invention) The present invention relates to a composition comprising at least (2R,3R)-2,3-butanediol and / or (2S,3S)-2,3-butanediol and (meso)-2,3-butanediol, wherein the content of the (meso)-2,3-butanediol is not more than twice the total content of the (2R,3R)-2,3-butanediol and the (2S,3S)-2,3-butanediol by weight.

[0023] (2R,3R)-2,3-butanediol and (2S,3S)-2,3-butanediol have excellent viral growth inhibitory effects. Conversely, (meso)-2,3-butanediol promotes viral growth. Commercially available 2,3-BDO contains these three optical isomers, and therefore exhibits almost no viral growth inhibitory effect. However, in the present invention, the (meso)-2,3-butanediol content is less than twice the combined content of (2R,3R)-2,3-butanediol and (2S,3S)-2,3-butanediol by weight, thereby demonstrating a viral growth inhibitory effect.

[0024] The composition of the present invention exhibits a viral proliferation inhibitory effect against enveloped and non-enveloped viruses.

[0025] Furthermore, since the composition of the present invention contains (meso)-2,3-butanediol, it can exhibit high moisturizing and moisture-absorbing effects, and can simultaneously exhibit both a viral growth inhibitory effect and a moisturizing and moisture-absorbing effect (see Chemical Abstracts Service, CAS: 5341-95-7).

[0026] When the composition of the present invention does not contain either (2R,3R)-2,3-butanediol or (2S,3S)-2,3-butanediol, the term "total content of (2R,3R)-2,3-butanediol and (2S,3S)-2,3-butanediol" means the content of either (2R,3R)-2,3-butanediol or (2S,3S)-2,3-butanediol contained in the composition.

[0027] Comparing (2S,3S)-2,3-butanediol with (2R,3R)-2,3-butanediol, (2S,3S)-2,3-butanediol exhibits a higher viral proliferation inhibitory effect. Therefore, from the viewpoint of the viral proliferation inhibitory effect, it is preferable that the content of (2S,3S)-2,3-butanediol in the composition of the present invention is higher than the content of (2R,3R)-2,3-butanediol.

[0028] Furthermore, when (2S,3S)-2,3-butanediol and (2R,3R)-2,3-butanediol are compared, (2R,3R)-2,3-butanediol is colorless and transparent, while (2S,3S)-2,3-butanediol is slightly yellow. Therefore, from the viewpoint of the degree of freedom in color adjustment, it is preferable that the content of (2R,3R)-2,3-butanediol in the composition of the present invention is higher than the content of (2S,3S)-2,3-butanediol.

[0029] In the composition of the present invention, the weight ratio of the (meso)-2,3-butanediol content is preferably 1.5 times or less, more preferably 0.5 times or less, even more preferably 0.13 times or less, and particularly preferably 0.05 times or less, the total weight ratio of the (2R,3R)-2,3-butanediol and (2S,3S)-2,3-butanediol content, because this has a significant effect of inhibiting viral proliferation.

[0030] The composition of the present invention may contain both (2R,3R)-2,3-butanediol and (2S,3S)-2,3-butanediol, and the weight ratio of the (2R,3R)-2,3-butanediol content to the (2S,3S)-2,3-butanediol content may be 1 / 1000 to 1000 / 1. The weight ratio of the (2R,3R)-2,3-butanediol content to the (2S,3S)-2,3-butanediol content may be 1 / 100 to 100 / 1, or even 1 / 10 to 10 / 1. It is preferable that the composition of the present invention containing (meso)-2,3-butanediol does not contain a racemate containing equal amounts of (2R,3R)-2,3-butanediol and (2S,3S)-2,3-butanediol, because the antiviral functions of (2R,3R)-2,3-butanediol and (2S,3S)-2,3-butanediol tend to be reduced.

[0031] The composition of the present invention preferably contains (2S,3S)-2,3-butanediol, and the content of (2S,3S)-2,3-butanediol is greater than the content of (meso)-2,3-butanediol. Furthermore, the composition of the present invention more preferably contains both (2S,3S)-2,3-butanediol and (2R,3R)-2,3-butanediol, and the content of (2S,3S)-2,3-butanediol is greater than the content of (2R,3R)-2,3-butanediol and is also greater than the content of (meso)-2,3-butanediol. As described above, (2S,3S)-2,3-butanediol exhibits a stronger viral proliferation inhibitory effect than (2R,3R)-2,3-butanediol. Therefore, when the content of (2S,3S)-2,3-butanediol is within the above range, the virus proliferation inhibitory effect is more suitably exhibited.

[0032] The composition of the present invention preferably contains (2R,3R)-2,3-butanediol, with the content of (2R,3R)-2,3-butanediol being greater than the content of (meso)-2,3-butanediol. Furthermore, the composition of the present invention preferably contains both (2S,3S)-2,3-butanediol and (2R,3R)-2,3-butanediol, with the content of (2R,3R)-2,3-butanediol being greater than the content of (2S,3S)-2,3-butanediol and more preferably greater than the content of (meso)-2,3-butanediol. While (2R,3R)-2,3-butanediol is colorless and transparent, (2S,3S)-2,3-butanediol is slightly yellow. Therefore, it is preferable that the amount of (2R,3R)-2,3-butanediol is greater than that of (2S,3S)-2,3-butanediol, since this increases the degree of freedom in adjusting the color of the composition. In particular, when the composition of the present invention is used as a cosmetic raw material, this is advantageous because it ensures the degree of freedom in adjusting the color of the cosmetic. From the perspective of the degree of freedom in adjusting the color of the cosmetic, the composition of the present invention does not need to contain (2S,3S)-2,3-butanediol. Note that the composition of the present invention can inhibit viral proliferation even if it does not contain (2S,3S)-2,3-butanediol.

[0033] In the composition of the present invention, the total content of (2R,3R)-2,3-butanediol and / or (2S,3S)-2,3-butanediol and (meso)-2,3-butanediol is preferably 5% by weight to 100% by weight based on the weight of the entire composition.

[0034] The composition of the present invention can be used without any particular limitation as long as it is used as a virus growth inhibitor that can exhibit a virus growth inhibitory effect. Specifically, the composition of the present invention can be used as a skin care topical composition, cosmetic composition, pharmaceutical composition, food additive, etc. Furthermore, the composition of the present invention can be formulated, for example, in the form of makeup cosmetics, toner, cream, lotion, essence, pack, etc., more specifically, in the form of softening toner, astringent toner, nutritious toner, eye cream, nutritious cream, massage cream, cleansing cream, cleansing foam, cleansing water, powder, foundation, makeup base, essence, pack, etc., and the formulation is not particularly limited. Furthermore, in each formulation, other ingredients can be appropriately selected and blended by those skilled in the art without difficulty depending on the type of other composition or the intended use. Furthermore, the composition of the present invention can be preferably formulated as a cleanser composition, and the formulation is not particularly limited, but specifically, it can be formulated in the form of a hand disinfectant, hand wash, body wash, cleansing cream, cleansing gel, cleansing foam, cleansing water, soap, wet tissue, etc. Furthermore, the composition of the present invention can be sprayed onto an area where a virus proliferation inhibitory effect is required, or can be impregnated into wet tissue, etc.

[0035] The cosmetic raw material composition of the present invention is characterized by containing the above-mentioned composition of the present invention. As described above, the composition of the present invention exhibits a virus proliferation inhibitory effect. Therefore, when a cosmetic is produced from the cosmetic raw material composition containing the composition of the present invention, the cosmetic exhibits a virus inhibitory effect.

[0036] The composition of the present invention is preferably stored or transported in a sealed container containing an inert gas or air with a humidity of 10% or less (including 0%). This is because moisture absorption can be prevented, thereby preventing denaturation such as oxidation of the composition. Examples of inert gases include nitrogen, argon, helium, and carbon dioxide.

[0037] Next, a method for producing the composition of the present invention will be described. The composition of the present invention can be prepared by mixing industrially produced (meso)-2,3-butanediol, (2R,3R)-2,3-butanediol, and (2S,3S)-2,3-butanediol in a predetermined ratio. Furthermore, optical isomers of 2,3-BDO can also be produced using microorganisms, as described, for example, in JP-A-10-234390 (Bacillus bacteria), JP-A-2015-518736 (genetically modified Escherichia coli), and JP-A-2004-357639 (genetically modified Escherichia coli). (meso)-2,3-butanediol, (2R,3R)-2,3-butanediol, and (2S,3S)-2,3-butanediol are commercially available, specifically, (meso)-2,3-butanediol (manufactured by Sigma-Aldrich, product number 361461), (2R,3R)-2,3-butanediol (manufactured by Tokyo Chemical Industry Co., Ltd. (TCI), product number B1161), and (2S,3S)-2,3-butanediol (manufactured by Tokyo Chemical Industry Co., Ltd. (TCI), product number B1343), respectively. JP-A Nos. 10-234390, 2015-518736, and 2004-357639 are incorporated herein by reference.

[0038] (Method for measuring the proportions of optical isomers of 2,3-BDO in a composition) In the composition of the present invention, the proportions of (meso)-2,3-butanediol, (2R,3R)-2,3-butanediol, and (2S,3S)-2,3-butanediol can be quantitatively and qualitatively analyzed using gas chromatography mass spectrometry (GC-MS) analysis and a chiral column. Agilent Technologies, Inc. possesses technology for separating the three optical isomers of 2,3-BDO, and the three optical isomers of 2,3-BDO can be separated, for example, under the following analytical conditions. Quantitation is also possible by creating a calibration curve using standard samples of each optical isomer.

[0039] Apparatus: GC / MS: Agilent Technologies 7890A / 5975C Measurement conditions Column: CP-Chirasil, 25 m x 0.25 mm id x 0.25 μm film thickness (Agilent Technologies, Inc.) Column temperature: 80°C (5 min) → +2°C / min → 150°C Column pressure: 51.5 kPa (constant linear flow rate mode) Carrier gas: He (1.0 mL / min) Injection port: 200°C, split 10:1 Injection volume: 1 μL Detector: MS Ionization method: EI method Electron energy: 70 eV EM voltage: 1294 V Ion source temperature: 230°C Interface temperature: 200°C Mass range: m / z=10-800

[0040] The present specification describes the following:

[0041] The present disclosure (1) is a composition comprising at least (2R,3R)-2,3-butanediol and / or (2S,3S)-2,3-butanediol and (meso)-2,3-butanediol, wherein the content of the (meso)-2,3-butanediol is not more than twice the total content of the (2R,3R)-2,3-butanediol and the (2S,3S)-2,3-butanediol by weight.

[0042] The present disclosure (2) is the composition according to the present disclosure (1), wherein the content of the (meso)-2,3-butanediol is 1.5 times or less by weight the total content of the (2R,3R)-2,3-butanediol and the (2S,3S)-2,3-butanediol.

[0043] The present disclosure (3) is the composition according to the present disclosure (1), wherein the content of the (meso)-2,3-butanediol is 0.5 times or less the total content of the (2R,3R)-2,3-butanediol and the (2S,3S)-2,3-butanediol by weight.

[0044] The present disclosure (4) is the composition according to the present disclosure (1), wherein the content of the (meso)-2,3-butanediol is 0.13 times or less the total content of the (2R,3R)-2,3-butanediol and the (2S,3S)-2,3-butanediol by weight.

[0045] The present disclosure (5) is the composition according to the present disclosure (1), wherein the content of the (meso)-2,3-butanediol is 0.05 times or less the total content of the (2R,3R)-2,3-butanediol and the (2S,3S)-2,3-butanediol by weight.

[0046] The present disclosure (6) is the composition according to any one of the present disclosures (1) to (5), wherein the composition contains the (2S,3S)-2,3-butanediol, and the content of the (2S,3S)-2,3-butanediol is greater than the content of the (meso)-2,3-butanediol.

[0047] The present disclosure (7) is the composition according to any one of the present disclosures (1) to (5), wherein the composition contains the (2R,3R)-2,3-butanediol, and the content of the (2R,3R)-2,3-butanediol is greater than the content of the (meso)-2,3-butanediol.

[0048] The present disclosure (8) is the composition according to any one of the present disclosures (1) to (7), wherein the composition contains both the (2S,3S)-2,3-butanediol and the (2R,3R)-2,3-butanediol, and the content of the (2S,3S)-2,3-butanediol is greater than the content of the (2R,3R)-2,3-butanediol and greater than the content of the (meso)-2,3-butanediol.

[0049] The present disclosure (9) is the composition according to any one of the present disclosures (1) to (7), which contains both the (2S,3S)-2,3-butanediol and the (2R,3R)-2,3-butanediol, and the content of the (2R,3R)-2,3-butanediol is greater than the content of the (2S,3S)-2,3-butanediol and greater than the content of the (meso)-2,3-butanediol.

[0050] The present disclosure (10) is the composition according to any one of the present disclosures (1) to (5) and (7), wherein the composition does not contain (2S,3S)-2,3-butanediol.

[0051] The present disclosure (11) is the composition according to any one of the present disclosures (1) to (7), wherein the composition does not contain racemates of (2R,3R)-2,3-butanediol and (2S,3S)-2,3-butanediol.

[0052] The present disclosure (12) is a composition according to any one of the present disclosures (1) to (11), which is used as a virus proliferation inhibitor.

[0053] The present disclosure (13) is a cosmetic raw material composition characterized by including the composition according to any one of the present disclosures (1) to (12).

[0054] Examples 1 to 8 and Comparative Examples 1 to 3 (meso)-2,3-butanediol (Sigma-Aldrich, product number 361461), (2R,3R)-2,3-butanediol (Tokyo Chemical Industry, product number B1161), (2S,3S)-2,3-butanediol (Tokyo Chemical Industry, product number B1343), and water (ion-exchanged water) were mixed in the weight ratios shown in Table 1 to prepare compositions according to Examples 1 to 8.

[0055] The composition of Comparative Example 1 is a composition consisting of water only, and Comparative Example 2 is a composition containing a mixture of (meso)-2,3-butanediol and water. Furthermore, Comparative Example 3 is a composition containing (2R,3R)-2,3-butanediol, (2S,3S)-2,3-butanediol, (meso)-2,3-butanediol, and water in a weight ratio of (2R,3R)-2,3-butanediol:(2S,3S)-2,3-butanediol:(meso)-2,3-butanediol=1:1:4.25.

[0056] The composition of Example 5 was subjected to GC-MS analysis as described above in "(Method for measuring the proportion of optical isomers of 2,3-BDO in a composition)." FIG. 1 is a chart showing the results of GC-MS analysis of the composition of Example 5. As shown in FIG. 1, it was demonstrated that even if (meso)-2,3-butanediol, (2R,3R)-2,3-butanediol, and (2S,3S)-2,3-butanediol were present in the composition, they could be separated. Furthermore, it was demonstrated that the weight percentages of the contents of (meso)-2,3-butanediol, (2R,3R)-2,3-butanediol, and (2S,3S)-2,3-butanediol could also be calculated based on this chart.

[0057] (Measurement of Residual Phage Virus Count) Using the compositions according to each Example and Comparative Example, the virus proliferation inhibitory effect was measured by counting the residual phage virus count in accordance with JIS R 1756. (1) 10 g of tryptophan, 5 g of yeast extract, 10 g of sodium chloride, and 15 g of agar were mixed in 1 L of water and autoclaved at 120°C for 10 minutes. The solution was placed in a Petri dish (90 mmφ×15 mm) and cooled and solidified to prepare a 1.5% LB agar medium. (2) 300 μL of the composition according to each Example and Comparative Example and bacteriophage Qβ (10 ８The mixture was mixed with 300 μL of (100 μL cpu / mL) and stirred three times by inversion, then allowed to stand at room temperature for 4 hours. (3) 200 μL of the solution (2) above was mixed with 9.8 mL of SCDLP solution. SCDLP solution was prepared by dissolving "Nutrient Broth" (manufactured by Wako Pure Chemical Industries, Ltd.) in water to a concentration of 41.8 g / L and autoclaving at 121°C, 2 atmospheres, and 20 minutes. (4) 1 mL of the solution (3) above was mixed into a test tube containing Escherichia coli (100 μL) in advance. (5) 4 mL of 0.5% LB agar solution (prepared by mixing 10 g tryptophan, 5 g yeast extract, 10 g sodium chloride, and 15 g agar with 1 L of water and maintaining at 45°C) was added to 1 mL of the solution (4) above, and the mixture was stirred once by inversion. (6) The solution from (5) above was placed in the LB agar medium dish from (1) above, and the solution from (5) above was spread over the surface of the agar medium while slowly rotating the dish. (7) Thereafter, the dish was left at 37°C for 16 hours. (8) The number of plaques that appeared in the dish was counted visually. The results are shown in Table 1.

[0058]

[0059] The plaques that appeared in the petri dish in step (8) above will now be described. By carrying out step (7) above, E. coli proliferates, forming a colony of E. coli over the entire surface of the LB agar medium in the petri dish. If active bacteriophage (virus) remains in the solution in step (5) above, the bacteriophage (virus) dissolves the E. coli cell membrane, causing the E. coli to disappear. In that area, no colony of E. coli forms, leaving only the LB agar medium. The area of ​​only the LB agar medium formed by the disappearance of E. coli is called a plaque, and the number of remaining bacteriophage (virus) can be counted by counting the number of plaques. A large number of such plaques indicates a large number of active bacteriophage (virus), while a small number of plaques indicates a small number of active bacteriophage (virus). In this experiment, a small number of plaques means that bacteriophage (virus) activity was inhibited by the compositions of the Examples and Comparative Examples in step (2). In other words, a small number of plaques observed means that the compositions used in step (2) have a high bacteriophage (virus) proliferation inhibitory effect.

[0060] (Antiviral Activity Evaluation Using Bacteriophage) To evaluate the viral proliferation inhibitory effect (hereinafter referred to as "antiviral activity") of the compositions according to Examples 1 to 8 and Comparative Examples 1 to 3, viral inactivation was measured using a modified method of JIS R1756, the antiviral activity test method for visible-light-responsive photocatalytic materials. Specifically, the compositions according to Examples 1 to 8, water (Comparative Example 1), an aqueous (meso)-2,3-butanediol solution (Comparative Example 2), and the composition according to Comparative Example 3 were mixed with bacteriophage Qβ in a sample tube, stirred by inversion, and then left for four hours to inactivate the bacteriophage (virus). The bacteriophage was then infected with Escherichia coli and left overnight, and the number of bacteriophages (viruses) that retained their infectious capacity was measured. The measurement results, expressed as the concentration of bacteriophages (viruses) inactivated against Escherichia coli, were expressed as bacteriophage (virus) inactivation. Here, the concentration of bacteriophage (virus) inactivated against E. coli (bacteriophage (virus) inactivation degree) was used as an index of bacteriophage (virus) concentration, and the bacteriophage (virus) inactivation degree was calculated based on this bacteriophage (virus) inactivation degree.

[0061] The bacteriophage (virus) inactivation rate is the result of calculating the concentration of bacteriophage (virus) inactivated against E. coli by measuring the concentration of bacteriophage (virus) capable of infecting E. coli in an antiviral test using bacteriophage, using a bacteriophage Qβ concentration of 8.3 million / mL. In other words, the bacteriophage (virus) inactivation rate is the degree of concentration at which E. coli cannot be infected, relative to the bacteriophage Qβ concentration, and can be calculated by (bacteriophage Qβ concentration - concentration of bacteriophage (virus) capable of infecting E. coli) / (bacteriophage Qβ concentration) × 100.

[0062] The bacteriophage (virus) inactivation degree is calculated from this bacteriophage (virus) inactivation degree. The bacteriophage (virus) inactivation degree is a numerical value (represented as a negative value) expressed as common logarithm log(1-X), where the amount of the original bacteriophage (virus) is 1 and the relative amount of the bacteriophage (virus) inactivated after the bacteriophage (virus) inactivation treatment is X. The larger the absolute value, the higher the ability to inactivate the bacteriophage (virus). For example, if 99.9% of the original bacteriophage (virus) is inactivated, the bacteriophage (virus) inactivation degree is expressed as log(1-0.999) = -3.00. The bacteriophage (virus) inactivation rate is the ratio of the amount of bacteriophage (virus) inactivated after bacteriophage (virus) inactivation treatment to the total amount of bacteriophage (virus) before the bacteriophage (virus) inactivation treatment, expressed as a percentage (99.9% in the above case). As described above, the bacteriophage (virus) inactivation rate was calculated from the bacteriophage (virus) inactivation rate. The results are shown in Table 1.

[0063] The viral inactivation degree in this specification is evaluated in accordance with JIS Z 2801 and JIS L 1922. Note that the viral inactivation degree has an opposite sign to the antiviral activity value described below. According to JIS L 1922, an antiviral activity value of 2.0 or higher is considered to be antiviral, and an antiviral activity value of 3.0 or higher is considered to be sufficient (see JP 2018-177747 A, incorporated herein by reference).

[0064] The results in Table 1 show that, in terms of weight ratio, when the content of (meso)-2,3-butanediol is 1.5 times or less, particularly 0.5 times or less, the combined content of (2R,3R)-2,3-butanediol and (2S,3S)-2,3-butanediol, the number of plaques that appeared was almost zero, demonstrating a high viral proliferation inhibitory effect. Furthermore, the number of plaques in Comparative Example 2, which is a mixed composition of (meso)-2,3-butanediol and water, was greater than that in Comparative Example 1, which was water, demonstrating the viral proliferation effect of (meso)-2,3-butanediol. Therefore, these test results also explain why 2,3-butanediol ((2R,3R)-2,3-butanediol: (2S,3S)-2,3-butanediol: (meso)-2,3-butanediol = 1:1:4.25), which is industrially produced and sold as a reagent, has no effect of inhibiting viral proliferation.

[0065] The reason why viral proliferation is promoted or inhibited depending on the type of optical isomer of 2,3-BDO is predicted as follows. First, by comparing Comparative Example 1 and Comparative Example 2, it is predicted that (meso)-2,3-butanediol is a substance useful for viral proliferation and promotes the production of some substance biosynthesized during viral proliferation. On the other hand, (2R,3R)-2,3-butanediol and (2S,3S)-2,3-butanediol function as antagonists of (meso)-2,3-butanediol and inhibit the production of some substance biosynthesized during viral proliferation. In other words, it is predicted that the presence of (2R,3R)-2,3-butanediol and (2S,3S)-2,3-butanediol prevents the production of some substance biosynthesized during viral proliferation, preventing the virus from proliferating, and as a result, the virus can be inactivated.

[0066] This can also be understood from the results of Comparative Example 3. In Comparative Example 3, the content of (meso)-2,3-butanediol was 2.1 times the combined content of the (2R,3R)-2,3-butanediol and the (2S,3S)-2,3-butanediol, and the viral proliferation inhibitory effect was 55 plaques and -1.15 viral inactivation, which are lower than those of water in Comparative Example 2. Furthermore, as can be understood from Examples 7 and 8, in the present invention, even if (2S,3S)-2,3-butanediol is not contained, it is understood that the viral proliferation inhibitory effect can be obtained as long as the amount of (meso)-2,3-butanediol is 0.13 times or less, particularly 0.05 times or less, that of (2R,3R)-2,3-butanediol by weight. In addition, when a comparative moisturizing test was carried out on (meso)-2,3-butanediol, (2R,3R)-2,3-butanediol, and (2S,3S)-2,3-butanediol in accordance with the moisturizing test described in Japanese Patent Application Laid-Open No. 2002-212021, which is incorporated herein by reference, it was found that the moisturizing property of (meso)-2,3-butanediol is higher than that of (2R,3R)-2,3-butanediol and (2S,3S)-2,3-butanediol.

[0067] As described above, the composition of the present invention has an excellent effect of inhibiting viral proliferation, and can be used in applications where inhibition of such viral proliferation is required, such as as a raw material for cosmetics.

Claims

1. containing at least (2R,3R)-2,3-butanediol and / or (2S,3S)-2,3-butanediol and (meso)-2,3-butanediol, A composition characterized in that the content of the (meso)-2,3-butanediol is not more than twice the total content of the (2R,3R)-2,3-butanediol and the (2S,3S)-2,3-butanediol in terms of weight ratio.

2. 2. The composition according to claim 1, wherein the content of the (meso)-2,3-butanediol is 1.5 times or less the total content of the (2R,3R)-2,3-butanediol and the (2S,3S)-2,3-butanediol in terms of weight ratio.

3. 2. The composition according to claim 1, wherein the content of the (meso)-2,3-butanediol is 0.5 times or less the total content of the (2R,3R)-2,3-butanediol and the (2S,3S)-2,3-butanediol in terms of weight ratio.

4. 2. The composition according to claim 1, wherein the content of the (meso)-2,3-butanediol is 0.13 times or less the total content of the (2R,3R)-2,3-butanediol and the (2S,3S)-2,3-butanediol in terms of weight ratio.

5. 2. The composition according to claim 1, wherein the content of the (meso)-2,3-butanediol is 0.05 times or less the total content of the (2R,3R)-2,3-butanediol and the (2S,3S)-2,3-butanediol in terms of weight ratio.

6. the composition comprises the (2S,3S)-2,3-butanediol; 2. The composition according to claim 1, wherein the content of the (2S,3S)-2,3-butanediol is greater than the content of the (meso)-2,3-butanediol.

7. the composition comprises the (2R,3R)-2,3-butanediol, 2. The composition according to claim 1, wherein the content of the (2R,3R)-2,3-butanediol is greater than the content of the (meso)-2,3-butanediol.

8. the composition contains both the (2S,3S)-2,3-butanediol and the (2R,3R)-2,3-butanediol; The composition according to claim 1, wherein the content of the (2S,3S)-2,3-butanediol is greater than the content of the (2R,3R)-2,3-butanediol and greater than the content of the (meso)-2,3-butanediol.

9. the composition contains both the (2S,3S)-2,3-butanediol and the (2R,3R)-2,3-butanediol; The composition according to claim 1, wherein the content of the (2R,3R)-2,3-butanediol is greater than the content of the (2S,3S)-2,3-butanediol and greater than the content of the (meso)-2,3-butanediol.

10. The composition according to any one of claims 1 to 5 and 7, wherein the composition does not contain (2S,3S)-2,3-butanediol.

11. The composition according to any one of claims 1 to 7, wherein the composition does not contain a racemate of (2R,3R)-2,3-butanediol and (2S,3S)-2,3-butanediol.

12. The composition according to any one of claims 1 to 9, which is used as a virus proliferation inhibitor.

13. A cosmetic raw material composition comprising the composition according to any one of claims 1 to 9.