JPS596056A - Production of deodorant - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention is a method for producing a deodorizing substance from plants of the family Sinaceae, such as sage and rosemary, especially a deodorizing substance that is effective against those whose odor source is a sulfur compound such as methyl mercaptan. Regarding.

Traditionally, bad odors emitted from sewage treatment plants, fish processing plants, fishmeal manufacturing plants, livestock or poultry manure drying plants, pulp factories, etc. have become a social problem, and in the living environment, food waste, filth, etc. There are many sources of bad odors, and it is desired to suppress their generation or eliminate odors. Furthermore, it is also desired to suppress and deodorize bad breath, which is one of the sources of bad odor.

Various substances are known to cause unpleasant odors, but sulfur compounds such as hydrogen sulfide and mercaptans are particularly problematic, and conventional methods for deodorizing them include activated carbon,
Adsorption to silica glue, zeolite, cyclodextrin, etc., direct combustion, oxidation using catalysts, ozone, hypochlorous acid, potassium permanganate, masking with aroma components,
Chemistry grades.

Although a method using a reaction reaction is adopted depending on the type of the source of the bad odor, etc., there is a demand for a deodorant component that is effective against sulfur compounds such as methyl mercaptan.

Traditionally, plants from the Labiata family, such as sage and rosemary, have been widely used as spices that have a pungent taste and nuttiness effect on foods, especially meat and fish. It has also been proposed to incorporate the leaves into chewing gum (JP-A-54-84070). However, when using sage, rosemary, etc. as a deodorizing agent, it takes time for the effect to appear, and it is good to use it in cooking simply for the taste and odor. , it is unsuitable as a deodorant that should be quick-acting, and when sage, rosemary, etc. are added to toothpaste to remove bad breath, the scent is too strong and is not practical. has.

The present inventors have conducted various studies on deodorizing substances that have an excellent deodorizing effect on sulfurized metals such as methyl mercaptan. As a result, the present inventors have found that sage, rosemary, etc. and/or a step of extracting with a solvent a raw material selected from extracts of plants of the Lamiaceae family, such as sage and rosemary, obtained by extraction with a non-polar solvent, and extracting residue thereof, and collecting the extract. After that, this extract is dissolved in a water-insoluble organic solvent, and an aqueous solution of an alkaline compound such as sodium hydroxide or sodium carbonate is added to the extract, and the effective deodorizing fraction is extracted. By collecting this alkaline compound aqueous solution layer, a substance with high deodorizing effect against methyl mercaptan can be obtained, and this substance can be used as an industrial deodorant, household deodorant, or toothpaste. It has been found that it can be suitably used as an active ingredient in oral deodorants such as mouthwash, chewing gum, and candy.Furthermore, in addition to the above steps, there is also a step of performing steam distillation treatment and collecting the residual liquid, and activated carbon. The inventors discovered that by performing a decolorization process using an adsorbent such as the above, an almost odorless or light-colored product can be obtained, and the present invention was developed based on this finding.

The present invention will be explained in more detail below.

When producing the deodorizing substance according to the present invention, raw materials include whole plants, aerial parts, roots, etc. of plants of the Labiata family, such as sage and rosemary, cut or powdered; Plants can be injected into water, polar solvents such as ethyl ether, ethylene chloride, dioxane, acetone, ethanol, methanol, ethyl acetate, propylene glycol, petroleum ether, ligroin, cyclohexane, carbon tetrachloride, chloroform, etc. , dichloromethane, 1,2-dichloroethane, toluene, benzene, etc., or an extract obtained by extraction with a mixed solvent thereof, and an extraction residue thereof.

In order to obtain a deodorizing substance from the above-mentioned raw materials, the above-mentioned raw materials are first subjected to an extraction treatment with a solvent and the extract is collected.

The extraction treatment is preferably carried out by adding a solvent to the raw materials and performing the extraction at room temperature or the reflux temperature of the solvent for 0.5 to 24 hours, particularly 1 to 10 hours. The solvent used in this extraction process may be an organic solvent or an inorganic solvent, or may be a mixed solvent of an organic solvent and an inorganic solvent. Specific examples of organic solvents include ethyl ether, ethylene chloride, dioxane, acetone, ethanol, methanol, acetic acid,
Chyl, propylene glycol, n-hexane, petroleum ether, ligroin, cyclohexane, carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane,
Examples include toluene and benzene. In addition, as an inorganic solvent, water and aqueous solutions of acids, alkalis, or their salts can be used, specifically hydrochloric acid, sulfuric acid, phosphoric acid, nitric acid, carbonic acid, hydroxide, potassium hydroxide, hydroxide, etc. Examples include ammonium, calcium hydroxide, sodium chloride, potassium chloride, ammonium chloride, sodium hydrogen carbonate, sodium carbonate, and sodium sulfate. In addition,
It is preferable to use these acids, alkalis, and salts at a concentration of 2 molar or less. The amount of the above-mentioned solvent to be used is preferably at least equal to the volume of the raw material or the steam distillation residue described below.

After the extraction process, the extract is separated into an extract and an extraction residue using a conventional method such as filtration, centrifugation, decantation, etc., preferably under heating, and the extract is collected. If necessary, the extraction residue may be subjected to the above-mentioned extraction process again to obtain an extract, which may be combined with the previous extract. In this case, it is also possible to use a different solvent from the previous solvent as the extraction solvent.

The extract obtained in this way is subjected to ion exchange, dialysis, etc. when the solvent is distilled off as necessary and inorganic solvent extraction treatment is performed, especially extraction treatment with acid, alkali, or salt. It is preferable to distill it off. ), proceed to the next process. Note that, if necessary, the product from which the solvent has been distilled off may be further subjected to extraction treatment using another solvent.

In the present invention, after performing the solvent extraction treatment step, the extract is dissolved in a water-insoluble organic solvent, and an aqueous solution of an alkaline compound is added to perform the extraction treatment, and the aqueous alkaline compound layer is collected. Perform the process of

In this case, water-insoluble organic solvents include ethyl ether, n-hexane, chlorinated hydrocarbons, ethyl acetate, n-butanol, isobutanol, benzene, cyclohexane, toluene, petroleum ether, gasoline, ligroin, etc. When the extract obtained in the solvent extraction step is used after all the solvent has been distilled off, it is dissolved in the water-insoluble organic solvent. Furthermore, in the solvent extraction step, when a water-insoluble organic solvent is used as the extraction solvent, the solvent may not be distilled off from the extract, and the extract may be used as it is as a solution in the water-insoluble organic solvent. In addition, when the extract obtained by distilling off the solvent is dissolved in a water-insoluble organic solvent, the amount of water-insoluble organic solvent used is preferably 0.5 times or more of the distillate.

In addition, examples of alkaline compounds include alkali metal hydroxides such as IJium hydroxide and potassium hydroxide, alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide, ammonia, charcoal, sodium hydroxide, potassium carbonate, etc. Alkali metal carbonates such as sodium hydrogen carbonate, alkali metal hydrogen carbonates such as sodium hydrogen carbonate, sodium phosphate, sodium hydrogen phosphate, sodium birophosphate, etc., sodium acetate,
Examples include alkali metal salts of organic acids such as sodium citrate. These alkaline compounds are used after being dissolved in water, and in this case, the concentration of the alkaline compound can be set to 0.1% to saturation in the water solution.

When the aqueous solution of the alkaline compound is added to the water-insoluble organic solvent solution of the extract for extraction treatment, the alkali compound aqueous solution may be immediately added to the water-insoluble organic solvent solution of the extract for the extraction treatment. First, an extraction process is performed in which an acid such as dilute sulfuric acid or dilute hydrochloric acid is added to a solution of the extract in a water-insoluble organic solvent and shaken.Then, this acid layer is separated and removed, and an aqueous alkali compound solution is added to the water-insoluble organic solvent layer. may be added to perform the extraction process, thereby reducing contamination of the final fraction with impurities.

Extraction treatment using an aqueous alkali compound solution can be carried out according to a conventional method, for example, by shaking at room temperature for 1 to 10 minutes. In addition, during this treatment, it is preferable that the water-insoluble organic solvent and the aqueous alkali compound solution be treated at a volume ratio of 1:5 to 5:1.

Further, this extraction treatment is preferably carried out under a non-oxidizing atmosphere, for example a nitrogen atmosphere.

After this extraction process, the mixture is allowed to stand, and the water-insoluble organic solvent layer and the alkaline compound aqueous solution layer are separated, and the alkali compound aqueous solution layer is collected. According to the present invention, the effective deodorizing fraction in the raw material is effectively transferred to this alkaline compound aqueous solution layer by the above-mentioned operation, and therefore, by collecting this alkaline compound aqueous solution layer, it can be used as a deodorizing substance. Obtainable.

The alkaline compound aqueous solution to which the effective deodorizing fraction has been transferred can be used as a deodorizing substance as it is or by concentrating or converting it, depending on the case. It is also possible to use neutralized products, concentrates, and dried products thereof. Furthermore 1. After adding acid to the alkaline compound aqueous solution and neutralizing it,
A water-insoluble organic solvent is added to this for extraction treatment, the effective deodorizing fraction in the alkaline compound aqueous solution is transferred to the water-insoluble organic solvent again, and this water-insoluble organic solvent is collected. It is also possible to use water-insoluble organic solvents as deodorizing substances.

In this case, most preferably, the water-insoluble organic solvent layer is washed with water if necessary, and then the solvent is distilled off, and the resulting product is used as a deodorizing substance.

In the present invention, in addition to the above-mentioned operations, it is possible to perform a step of steam distillation and collect the residual liquid, thereby producing an almost odorless and highly effective deodorizing substance. Obtainable.

This steam distillation treatment is performed before the solvent extraction treatment.
That is, the raw material may be subjected to steam distillation treatment, the residue thereof may be collected, and the residue may be subjected to solvent extraction treatment, or after the solvent extraction treatment and before treatment with an aqueous alkaline compound solution, especially For the solvent extraction process,
The extract obtained by distilling off the solvent may be subjected to a steam distillation treatment, and the residue may be collected, and the residue may be dissolved in a water-insoluble organic solvent and treated with an aqueous alkaline compound solution. After treatment with an alkali compound aqueous solution, for example, a concentrate or dry product of this alkali compound aqueous solution, a concentrate or dry product of a neutralized alkali compound aqueous solution, or a re-extraction with a water-insoluble organic solvent. The solvent may be distilled off and the residue may be collected by steam distillation.

In the steam distillation treatment, the material to be treated is poured into water, preferably at least 10 times the weight in terms of solid matter, stirred, dispersed in water, heated under normal pressure or reduced pressure, and brought to a boil.
Let's do it. This removes the essential oil components along with the steam, but the deodorizing components remain in the steam distillation residue. Note that in this steam distillation step, steam can also be blown into the dispersion to promote volatilization of the essential oil components.

After continuing steam distillation until almost no essential oil components are recognized in the steam distillate, the steam distillation residue is recovered. This steam distillation residue is 1. Extraction treatment after steam distillation treatment,
If treatment with an aqueous alkali compound solution is performed, these treatments are performed, and if steam distillation is performed as the final step, the steam distillation residue is collected as a deodorizing substance.

In addition, when performing solvent extraction treatment after steam distillation treatment,
When using an inorganic solvent such as an organic solvent, an acid, or an alkali as a solvent, the dispersion after steam distillation is heated or cooled, and then separated into an aqueous layer and a solid by a method such as filtration, centrifugation, or decantation. Generally, this solid content is subjected to an extraction process, but in some cases, an aqueous layer separated from the dispersion may also be subjected to an extraction process. In this case, an organic solvent or an inorganic solvent is directly added to the dispersion liquid for extraction, and the extract is collected as a steam distillation residue, and at the same time the extract is collected as a steam distillation residue, and the extract is collected as a steam distillation residue. It can be collected as an extract from an extraction process. In this case, the extract (steam distillation residue) of the dispersion using an organic or inorganic solvent may be subjected to the above extraction treatment again. Furthermore, in the case where the solvent extraction step is performed after the steam distillation treatment, if water is used for this solvent extraction, the solid content is separated from the dispersion after the steam distillation treatment, water J4 is collected, and this aqueous layer or This can be concentrated and collected as an extract. In addition, when performing extraction treatment with acid, alkali, or salt, add acid, alkali, or salt to this aqueous layer or concentrated liquid.
Alternatively, a method of adding salt to a predetermined concentration can also be adopted.Also, when processing with an aqueous alkaline compound solution after steam distillation, the concentrate, dry matter, and solid content separated from the dispersion can be used. Alternatively, the concentrated or dried aqueous layer may be dissolved in a water-insoluble organic solvent and treated, but the alkali compound is dissolved in the dispersion, a water-insoluble organic solvent is added, and the mixture is shaken. Extraction treatment can also be carried out〇 When performing the decolorization treatment described below after the steam distillation treatment, when performing the decolorization treatment on the solid content, the solid content is dissolved in an appropriate solvent before the treatment, and When decolorizing the aqueous layer, the adsorbent can be directly introduced into the aqueous layer. Furthermore,
The treatment can also be carried out by adding an adsorbent to the solvent extract of the dispersion after steam distillation.

In addition, when a steam distillation process is performed at the end, the steam distillation residue is collected as a deodorizing substance. It can be recovered as a liquid or its concentrate. It is also possible to perform an extraction treatment on the dispersion using an organic solvent or an inorganic substance such as an acid or an alkali, and recover the extract (preferably from which the solvent has been distilled off) as a deodorizing substance.

Furthermore, in the present invention, decolorization treatment using an adsorbent can be carried out, thereby making it possible to obtain a light-colored and highly effective deodorizing substance. This decolorization treatment may be performed before or after the treatment with the alkaline compound aqueous solution as long as it is after the solvent extraction treatment, and if steam distillation treatment is performed, it may be performed before or after the operation. Good too.

In this method of decolorization using an adsorbent, if the object to be treated is solid, it is dissolved in an appropriate solvent to make it liquid, then an adsorbent such as activated carbon, diatomaceous earth, or acid clay is added, and the material is left at room temperature for about 10 to 60 minutes. Alternatively, it is preferable to carry out the reaction by stirring while heating. In addition, if it is in liquid form, it can be treated by adding an adsorbent as it is. In this case, the amount of adsorbent used is 0.5 to 8% by weight for the raw materials, 2 to 6% by weight for cut or powdered materials and extraction residues, and 0.5% for extracted extracts. It is preferable to set it as 2 weight%.

After the decolorization treatment, the adsorbent is separated in a furnace and the lachrymal fluid is collected.The adsorption agent is preferably added to this F solution, and the decolorization treatment is performed two to three times. When the tear fluid thus obtained is finally subjected to this decolorization treatment, the solvent is preferably distilled off under reduced pressure to concentrate and dry it, and then the tear fluid is collected as a deodorizing substance.

The deodorizing substance obtained by the above method has a fast-acting and excellent deodorizing effect, especially against methyl mercazotan, and can effectively suppress, deodorize, and prevent the bad odor of methyl mercaptan, and is therefore suitable for food processing. It is used as an active ingredient in industrial deodorizers for the sources of bad odors generated in factories, pulp mills, etc., household deodorizers for the sources of bad odors generated in garbage, toilets, etc., and as an oral deodorizer, toothpaste, and mouse. It can be incorporated into oral compositions such as washies, troches, chewing gum, and candies as an effective deodorizing ingredient to prevent bad breath. In this case, especially for the purpose of preventing bad breath,
It is preferable to use those obtained by steam distillation because essential oil components are removed and, therefore, the odor is reduced. The deodorizing substance of the present invention may be used alone as a deodorant, or it may be used in combination with other deodorizing active ingredients, or it may be used in combination with other ingredients commonly used in deodorants. For example, oxidizing agents such as sodium perborate, hypochlorous acid, manganese dioxide, permanganate, benzoquinone, and naphthoquinone, aldehydes such as glyoxal and acrolein, ketones, 1,2-propylene oxide, L2 = α, β of epoxy compounds such as n-butylene oxide, methacrylic acid esters, maleic acid derivatives, etc.
- Unsaturated compounds, metal salts such as copper sulfate and zinc sulfate, adsorbents such as activated carbon, silica dal, and alumina may be blended together. The deodorant may be in the form of a solution in which the deodorizing substance of the present invention is dissolved in an appropriate solvent, or may be in the form of powder, granules, blocks, or the like. When the deodorizing substance of the present invention is blended into an oral composition, etc., the blending amount is 0.0001 to 50% by weight of the total, more preferably o, ooi to 1ON, and even more preferably 0.01% by weight. ~5
It is preferable to set it as weight%.

In this case, the deodorizing substance of the present invention has high deodorizing power, and when steam distillation is performed, essential oil components are removed. It has almost no characteristic fragrance, and if it has been decolorized, it has a light color, so when it is blended into oral compositions, it does not impair the feeling of use.

In addition, when blending the deodorizing substance of the present invention into an oral composition,
As the components of the oral composition, appropriate components depending on the type thereof can be used. For example, in the case of toothpaste, dicalcium phosphate, galsium carbonate, calcium birophosphate, insoluble sodium meta-IJ heptaate, amorphous silica,
Abrasives such as crystalline silica, aluminosilicate, aluminum oxide, aluminum hydroxide, resin (compounding amount usually 20-60% by weight), carboxymethyl cellulose,
Binder such as hydroxyethyl cellulose, alginate, carragnan, gum arabic, polyvinyl alcohol (
Thickening agents (usually 10-70% by weight) such as polyethylene glycol, sorbitol, glycerin, and zoropylene glycol (usually 10-70% by weight), sodium lauryl, sodium dodecylbenzenesulfonate, hydrogenated coconut fatty acid monoglyceride Foaming agents (usually 0.1 to 5% by weight) such as sodium sulfate, sodium lauryl sulfoacetate, sodium N-lauroyl sarcosinate, N-acylglutamate, sucrose fatty acid ester, and essential oils such as peppermint and spearmint. - Ingredients such as flavoring materials such as menthol, carganese, eugenol, and anethole, sweeteners such as saccharin sodium, stevioside, neohesberidyl dihydrochalcone, glycyrrhizin, perillartine, p-methoxycinnamic aldehyde, and preservatives in water. Mix with and manufacture according to conventional methods. Also, in mouthwashes and other mouthwashes, ingredients are appropriately blended depending on the properties of the product.

In addition to the above-mentioned deodorizing substances, the oral composition also contains lysozyme chloride, dextranase, lytic enzyme, mutanase, chlorhexidine, nruvic acid, alexidine, hinokitiol, cetylpyridinium chloride, alkylglycine, alkyldiaminoethylglycine. salt,
Allantoin, ε-amitsukazolonic acid, tranexamic acid, azulene, vitamin E1 sodium monofluorophosphate, fluoride) IJium, stannous fluoride, water-soluble primary or diphosphoric acid salts, quaternary ammonium compounds, sodium chloride It is also possible to incorporate active ingredients such as.

jnl L, according to the method for producing a deodorant substance of the present invention, a substance that is fast-acting and has a high deodorizing effect and effect on methyl mercaptan can be obtained by simple operations, and this substance can be used in various deodorants. It can be suitably used as a deodorizing active ingredient, and when subjected to steam distillation, it has almost no scent derived from sage, rosemary, etc., and when decolorized, its color is light. Since it is highly safe in use, it is very effective as an active deodorizing ingredient for the oral cavity.

Hereinafter, the present invention will be specifically explained using examples.

In addition, in all cases, ``chi'' indicates weight %.

[Example 1] 27 g of dark green powder obtained by extracting the dry powder of the aerial part of sage with methanol was extracted with petroleum ether for 5 hours using a Soxhlet extractor to obtain 6.3 g of dark green paste. Ta. Dissolve this in 200cc petroleum ether,
The operation of adding about 2 g of activated carbon, stirring and filtering was repeated t-3 times. Next, this petroleum ether solution was extracted with about 3% sodium bicarbonate aqueous solution, and the petroleum ether layer was further extracted twice with fresh 3% sodium bicarbonate aqueous solution. A brown aqueous sodium bicarbonate solution was collected, neutralized by adding an aqueous IN hydrochloric acid solution, and then petroleum ether was added and shaken to collect the deodorizing substance in the petroleum ether layer, which was then concentrated to form a light brown color. 0.7 g of deodorizing substance was obtained.

[Example 2] The dry powder of the above-ground parts of sage was extracted with methanol, the obtained dark green powder was steam distilled, the essential oil was removed and the steam distillation residue powder 24.9 was extracted using a Soxhlet extractor The mixture was extracted with benzene for 5 hours to obtain 11.0 g of a dark green powder. This was dissolved in 200 CC of ethyl ether and extracted three times with 20 OCC of an approximately 3% aqueous sodium carbonate solution.The extracts were combined and neutralized by adding IN hydrochloric acid aqueous solution, then 200 ω of ethyl ether was added and the ethyl ether layer was shaken. The deodorizing substance was collected. 2 g of activated carbon was added to this, and the stirring and filtration operations were repeated three times to obtain 2.1 g of a light brown deodorizing substance.

[Example 3] 100 i of dry powder of the aerial parts of sage was extracted with ethyl ether for 5 hours using a Soxhlet extractor, and 13.8.
A dark green paste of No. 9 was obtained. Suspend this in 200ml of water, perform steam distillation on a mantle heater to remove the essential oil, then add 2g of sodium hydroxide and 200cc of benzene in a nitrogen stream, stir well and hydroxylate)
The IJum solution was collected under a nitrogen stream. Furthermore, 1% hydroxide is applied to the benzene layer in a nitrogen stream) IJium aqueous solution 2
00CI4-Addition and extraction are performed twice, and the alkaline solution is neutralized with IN hydrochloric acid solution, then benzene is added and shaken, the deodorizing substance is recovered in benzene, and this is concentrated to form a pale brown deodorant. 4.3y of odor substance was obtained.

[Example 4] Dry powder of sage aerial parts was extracted with petroleum ether for 5 hours using a 100#t Soxhlet extractor, the residue was dried, further Soxhlet extraction was performed with benzene, and the extract was concentrated.5. A green paste of 2I was obtained. This 2
Dissolve in 00 CC of ether, add 200 CC of tri-sodium carbonate aqueous solution and extract three times. After neutralizing the alkaline solution with IN hydrochloric acid solution, add ether and shake. Dissolve the deodorizing substance in ether. It was collected and concentrated to obtain a light brown deodorant substance o, s 11.

[Example 5] Add 500 grams of ethanol to 100 g of the residual dry powder obtained by steam distilling the dried powder of the above-ground parts of rosemary to remove the essential oil, and reflux for 1 hour on a water bath at 70 to 80 °C with a cooling tube attached. did. Next, this was separated into a furnace, fresh ethanol was added to the residue, and the same reflux was repeated twice to perform the extraction operation three times in total. The extract was concentrated to about 200 CC, about 2 g of activated carbon was added, and the stirring and filtration process was repeated three times to concentrate the lachrymal fluid to obtain 9.3 g of light brown powder. Dissolve this in 2000H ethyl ether,
After removing the ethyl ether insoluble area, it was extracted with 200 cc of 2% sodium carbonate solution, and the ether layer was further extracted twice with fresh sodium carbonate solution. Three portions of the extract were combined and neutralized with 1N hydrochloric acid, then ether was added to collect the deodorizing substance in the ether, and then concentrated to obtain a brown deodorant substance 1.6.9e.

[Example 6] In the same manner as in Example 5, 100 y of steam distillation residue of the above-ground rosemary plant was extracted with ethanol, decolorized, and made into an ether solution. This is hydroxylated in a nitrogen stream)
After extraction with IJum and neutralization, the deodorizing substance was recovered in ether using ether, and this was concentrated to obtain 4.5y of a brown deodorant substance.

[Example 7] In the same manner as in Example 5, the steam distillation residue 1'00 II of the aboveground part of rosemary was extracted with ethanol,
After decolorizing, it was made into an ether solution. This was extracted with saturated calcium hydroxide in a nitrogen stream. The aqueous layer and the precipitate, which became calcium salts, were combined and neutralized with IN hydrochloric acid, then ether was added to recover the deodorizing substance in ether and concentrating to obtain brown deodorant substance 4.611.

[Examples 8 to 10] Deodorizing substances were obtained in the same manner as in the above Examples according to the steps shown in Table 1, using powdered roots of Scutellaria spp.

Next, the deodorizing power of each deodorizing substance was investigated using the following method. The results are shown in Table 1.

Deodorizing power test: An ethanol solution containing a predetermined amount (amount shown in Table 1) of a sample (deodorizing substance) in a test tube with a capacity of 22 to 23 mJ.
For control, only ethanol) 1+++/ and 0
．． The temperature was adjusted to -7.5 by adding 1.5 ml of 1M phosphate buffer. To this was added 0.5 ml of a 10 volume aqueous solution of thiethanol containing 1 ppm of methyl mercaptan, and the mixture was immediately capped with a rubber stopper and stirred vigorously for 1 minute.

Thereafter, the test tube was allowed to stand at 37° C. for 6 minutes, and then 5 ml of air was injected into the test tube by piercing the rubber stopper with a gas syringe for gas chromatograph. After stirring vigorously for 30 seconds, use the same gas syringe to increase the headspace to 5 ttr.
The sample was immediately injected into a gas chromatograph, and the methyl mercaptan Ω integral count was measured. In addition, as a gas chromatograph, 163 manufactured by Hitachi, Ltd. was used.

The results were expressed as deodorization rate using the following formula.

C: Integral count of control S: Integral count of sample 28 Below, an example of negative use of the deodorizer of the present invention will be shown. In addition, all numbers indicate weight %.

[Usage example 1] Candy sugar 50 t water candy 33 organic acid
2 Fragrance 0.2 Deodorizing substance of Example 1 0.1 Water
Remaining ioo, ochi [Usage Example 2] Candy sugar 50chi Water Candy 33 Organic acid 2 Flavor 6.2 Deodorizing substance of Example 2 0.2 Water
Remaining 100.0 [Use example 3] Toothpaste calcium carbonate 50.0
Tiglycerin 20.0 Kara r Nan 0.5 Cal? oxymethylcellulose 1.0 lauryl diethanolamide 1.0 sucrose monolaurate 2.
0 Fragrance 1.0 Saccharin 0.1 Deodorizing substance of Example 3 0.15 Chlorhexidine 0.01 Dextranase 0.01100.0% [Use example 4] Toothpaste dicalcium phosphate dihydrate 50. 0
% Glycerin 20.0 Carboxymethyl cellulose 2.0 Sodium lauryl sulfate 2.0 Fragrance 1.0 Zaccharin 0.1 Deodorizing substance of Example 4 0.2 Chlorhexidine 0.01 Water
Remaining 100.0% [Usage example 5] Chewing gum gum paste 20% sugar
53 glucose
10 water candy 16.4
Fragrance: 0.5 Deodorizing substance of Example 5: 0.1 ioo
, o % [Usage example 6] Chee-ing gum gum paste 20 Chi sugar Sugar
55 corn syrup
12 water candy
9.3 Flavors
0.5 Deodorizing substance of Example 6
0.2 [Usage Example 7] Liquid toothpaste sodium polyacrylate 50.
0% glycerin 30.0 fragrance
Fee 0.9
Satucalin 0.1 Deodorizing substance of Example 4 0.05 Ethanol 3.0 Chlorhexidine
0.01 linoleic acid
0.04 Wednesday
Remaining: 100.0% [Usage Example 8] Mouthwash ethanol 20.0% Flavor 1.
0 Satukarin 0.05 Example 4
Deodorizing substance 0.1 Example 6
of 〃0.1 Sodium monofluorophosphate 0.
1 Chlorhexidine 0.01 Lauryl diethanolamide 0.3 Water Remaining 100.0
% [Usage example 9] Gargling tablet sodium bicarbonate 54.0% 2nd
Sodium phosphate 10.0 Polyethylene glycol 3.0 Citric acid
17.0 Anhydrous sodium sulfate 13.25 fragrance
Material 2.0 Example 5 Deodorizing substance 0.3 Example 6 //
0.2 Oleic acid 0
・1 Sodium monofluorophosphate 0.1 Chlorhexidine 0.05100.0% [Usage example 10] Deodorizing sugley ethanol 50% dichlorodifluoromethane 49.5 Deodorizing substance of Example 1
0.5100.0% [Usage Example 11] Liquid deodorant ethanol 99.4 Chika
Food 0.1 Deodorant substance of Example 2 0.5 Applicant Lion Co., Ltd. Agent Patent attorney Takashi Kojima Patent attorney Hanyo Takahata

Claims (1)

[Claims] 1. Solvent extraction treatment for raw materials selected from extracts and extraction residues obtained by extracting Lamiaceae plants and Lamiaceae plants with polar and/or non-polar solvents. and collecting the extract, and then adding an aqueous solution of an alkali compound to the extract dissolved in a water-insoluble organic solvent, performing an extraction process, and collecting the aqueous alkali compound layer. The deodorizing effective fraction in the raw material is added to the alkaline compound aqueous solution 1@
A method for producing a deodorizing substance, characterized in that the deodorizing substance is obtained from the raw material (by transferring the raw material to a deodorizing substance). 2. A raw material selected from extracts and extraction residues obtained by extracting Lamiaceae plants and Lamiaceae plants with polar and/or non-polar solvents is subjected to solvent extraction treatment to obtain the extract. , and then adding an aqueous solution of an alkali compound to the extract dissolved in a water-insoluble organic solvent, performing an extraction process, and then collecting the aqueous alkali compound layer, and further the solvent extraction step. After the treatment, a step of decolorizing with an adsorbent is carried out before or after the treatment with the alkaline compound aqueous solution to transfer the deodorizing effective fraction in the raw material to the alkaline compound aqueous solution layer. A method for producing a deodorizing substance, characterized in that the deodorizing substance is obtained from the above-mentioned raw materials. 3. Performing a solvent extraction process on raw materials selected from the extracted extracts and extraction residues obtained by extracting Lamiaceae plants and Lamiaceae plants with polar and/or non-polar solvents, and collecting the extracts. Thereafter, an aqueous solution of an alkali compound is added to the extract dissolved in a water-insoluble organic solvent, and an aqueous solution layer of the alkali compound is collected after an extraction process, and the solvent extraction process is further carried out. Before or after the treatment with the alkaline compound aqueous solution after the solvent extraction treatment, the deodorizing effective fraction in the raw material is collected by steam distillation and the residue is collected. A method for producing a deodorizing substance, characterized in that the deodorant substance is obtained from the raw material by transferring it into an aqueous alkali compound solution layer and a steam distillation residue, respectively. 4. Using a polar solvent and/or a polar solvent and/or a polar solvent and/or
Alternatively, the raw material selected from the extract obtained by extraction with a non-polar solvent and its extraction residue is subjected to solvent extraction treatment to collect the extract, and then this extract is converted into a water-insoluble organic A step of adding an aqueous solution of an alkali compound to the solution dissolved in a solvent, performing an extraction treatment, and collecting this aqueous alkali compound solution layer; and a step of collecting the alkali compound aqueous solution layer before or after performing the solvent extraction treatment. A step of performing steam distillation and collecting the residue before or after the treatment with an aqueous solution, and further decolorizing with an adsorbent after performing the solvent extraction treatment and before or after the steam distillation treatment. A deodorizing substance is obtained from the raw material by performing a step of transferring the effective deodorizing fraction in the raw material into the alkalized metal aqueous solution layer and the steam distillation residue, respectively. Method for producing odor substances.