Novel compounds and serotonin reuptake inhibitors

Abstract

The present invention aims to provide a serotonin uptake inhibitor that can exert its effects more efficiently by analyzing the component composition of plants of the genus Valerian. [Solution] The present invention provides a serotonin reuptake inhibitor comprising a compound represented by the following formula (1), and one or more selected from the group consisting of the compound, canoconyl acetate, and α-kesyl acetate as active ingredients. [Formula 1] TIFF2026060423000008.tif50170

Description

Technical Field

[0001] The present invention relates to novel compounds and serotonin uptake inhibitors.

Background Art

[0002] Valeriana fauriei Briq. has been traditionally used as a raw material for women's medicines in Japan, and is formulated into pharmaceuticals for menopause, menstrual pain, blood circulation disorders, irregular menstruation, cold sensitivity, etc., expecting an anxiolytic effect. It is also used as a flavoring agent for foods such as confectionery.

[0003] Valeriana officinalis has been used as a folk medicine in Europe, expecting a sedative effect since ancient times, and its recognition in Japan is relatively high. For this reason, it is formulated into herbal tea, bath agents, cosmetics, and health food supplements and is utilized.

[0004] Patent Document 1 describes that a composition containing an NSAID and a Valeriana extract can more greatly improve pain caused by stress or trauma and release from muscle tension. Patent Document 2 describes that a processed product such as a Valeriana extract, when combined with acetaminophen, ethenzamide, and allylisopropylacetylurea, exhibits an effect of improving pain and insomnia (sleep maintenance disorder). Patent Document 3 describes that a combination of a Valeriana extract and any one of ascorbic acid, glutamic acid, and ondj extract can exhibit an analgesic effect and enhance a sedative effect. Patent Document 4 describes that an oral composition containing a hydrous ethanol extract of the root of Valeriana officinalis together with cannabidiol can exhibit a relaxing effect.

Prior Art Documents

Patent Documents

[0005]

Patent Document 1

[0006] While Patent Documents 1-4 describe uses related to the sedative effect of valerian extract, they do not describe the relationship between the components of valerian and its serotonin reuptake inhibitory effect.

[0007] The present invention aims to provide a serotonin uptake inhibitor that can exert its effects more efficiently by analyzing the component composition of plants of the genus Valerian. [Means for solving the problem]

[0008] The present invention provides the following [1] to

[15] . [1] A compound represented by formula (1), described below. A serotonin reuptake inhibitor comprising one or more compounds selected from the group consisting of the compounds described in [2][1], canoconyl acetate, and α-kesyl acetate as an active ingredient. A serotonin reuptake inhibitor according to [2], comprising the compound described in [3] [1], canoconyl acetate, and α-kesyl acetate as active ingredients, and satisfying any of the following conditions. (A) The molar ratio of the canoconyl acetate content to the total amount of the compounds described in [1] and α-kesyl acetate is 0.5 or greater. (B) The canoconyl acetate content relative to the active ingredient content is 3 mol% or more. (C) The content of α-kesyl acetate relative to the content of the active ingredient is 1 mol% or more. [4] The agent according to [2] or [3], further comprising kesyl glycol diacetate as an active ingredient. [5] A serotonin reuptake inhibitor as described in [4], wherein the value calculated by the following formula is 130% or less. Relative serotonin uptake (%) = -440 × log[concentration of canoconyl acetate (μM)] - 327 × log[concentration of kesyl glycol diacetate (μM)] + 122 × log[concentration of canoconyl acetate (μM)] × log[concentration of kesyl glycol diacetate (μM)] + 1259 [6] The agent according to [4] or [5], wherein the ratio of kesyl glycol diacetate to canoconyl acetate (by weight) is 1 to 20:1. [7] The agent according to any one of items [2] to [6], wherein the active ingredient content is 800 μM or more. [8] The agent according to any one of items [2] to [7], wherein the active ingredient is derived from at least a part of a plant of the genus Valerian or a processed product thereof. [9] The agent described in [8], wherein the plant is one or more of the genus Valeriana, selected from Valeriana fauriei, Valeriana verum, Valeriana sylvestris, and Valeriana lisianthus.

[10] The agent according to [8] or [9], wherein the processed product is an alcohol extract of the plant body or a part thereof of a plant of the genus Valerian.

[11] The processed product is the agent according to [3] or [4], comprising 0.8% by weight or more of kesyl glycol diacetate. An antidepressant or anxiolytic comprising one or more compounds selected from the group consisting of the compounds described in

[12] [1], canoconyl acetate, and α-kesyl acetate as an active ingredient. An antidepressant or anti-anxiety food composition comprising one or more compounds selected from the group consisting of the compounds described in

[13] [1], canoconyl acetate, and α-kesyl acetate as an active ingredient.

[14] The composition according to

[13] , which is a health food, functional food, health supplement, nutritional functional food, special dietary food, or food for specified health uses. A method for producing a serotonin uptake inhibitor, comprising the step of mixing raw material components containing the compound described in

[15] [1], canoconyl acetate, and α-kesyl acetate. [Effects of the Invention]

[0009] Since the serotonin uptake inhibitor of the present invention can exhibit good serotonin uptake inhibitory activity, it can be effectively used as a functional food or the like.

Brief Description of the Drawings

[0010] [Figure 1] Figure 1 is a diagram showing the serotonin uptake amount of the ethanol extract of

[0009] . [Figure 2] Figure 2 is a diagram showing the serotonin uptake amount when (a) only kessyl glycol diacetate (KGD) is added, or (b) when a fraction of the ethanol extract of

[0009] and KGD are mixed and added. [Figure 3] Figure 3 is a diagram showing the serotonin uptake amount of (a) canoconil acetate (KNA), (b) canocol, or (c) α-kessyl acetate (α-KA). [Figure 4] Figure 4 is a diagram showing the correlation between the serotonin uptake amount measured by cell experiments and the predicted value of Samples 1 to 13 containing KNA, canocol, α-KA, and KGD in various mixing ratios.​​​​​​​​​​​​​​​​​​​​​​Canokol may be either naturally derived or artificially synthesized, but naturally derived is preferred, and preferably derived from plants of the genus Valeriana (using the plant body, a part thereof, or a processed product of a plant of the genus Valeriana as a raw material). Examples of plants of the genus Valeriana include Valeriana fauriei Briq., European valerian (V. officinalis), Indian valerian (V. jatamansi (V. wallichii)), climbing valerian (V. flaccidissima), and lisianthus (V. phu (V. edulis)). The plant body of a plant of the genus Valeriana may be a part thereof, for example, a part including the roots, rhizomes, or leaves, preferably a part including the roots and / or rhizomes. Examples of processed products include Examples include processing treatments (preferably including drying, crushing, and extraction) applied to the plant body or part thereof of a plant of the genus Valerian, such as crushing, drying, heating, extraction, solid-liquid separation, concentration, granulation, and / or powdering. More specifically, for example, a processed product obtained by drying and pulverizing the raw plant body (whole or part) of Valerian (Valerian powder: may be coarse powder or fine powder, obtained by drying the raw plant body or part thereof of a plant of the genus Valerian). Examples of processed materials include dried and chopped products (chopped) and Valerian plant extracts. Examples of Valerian plant extracts include live plants or parts thereof, dried products, extracts obtained by extracting dried and crushed products with a solvent, dried products (dried extracts), and powdered dried extracts obtained by powdering these. Preferably, processed products of the roots and rhizomes of Valerian plants are used, and more preferably, a dried extract obtained by drying and crushing a part of a Valerian plant including the roots and rhizomes and extracting it with a solvent. Examples of extraction solvents include alcohol such as ethanol, a mixed solvent of alcohol and water, and hexane, and are aqueous alcohols (preferably 30% or more by mass of alcohol, 40% or more by mass, or 50% or more by mass) and hexane. Extraction may be performed by cold maceration or ultrasonic extraction. The extraction time can be determined according to the extraction conditions, for example, 3 to 60 hours for cold maceration and 15 minutes to 3 hours for ultrasonic extraction.

[0013] Canocol can be isolated from other components in a plant extract of the Valerian genus, for example, by purification using chromatography. Examples of purification methods include those described in the examples below.

[0014] [2. Serotonin reuptake inhibitors] [Active ingredient (compound)] Kanokol can exert a serotonin reuptake inhibitory effect and can therefore be used as an active ingredient in serotonin reuptake inhibitors. In addition to the above compounds, canoconyl acetate (KNA: formula (3) below) and α-kessyl acetate (α-KA: formula (4) below) can also exert a serotonin reuptake inhibitory effect and can similarly be used as active ingredients in serotonin reuptake inhibitors.

[0015] [ka]

[0016] [ka]

[0017] Canokol, KNA, and α-KA can each be used individually or in combination of two or more, preferably in combination of three, as active ingredients in serotonin reuptake inhibitors. When the active ingredients are a combination of three, the ratio of KNA content to the total amount of canokol and α-KA (KNA / (canokol + α-KA)) is preferably 1.7 or less and 0.60 or more. This allows for a superior serotonin reuptake inhibitory effect.

[0018] The canocol content is preferably 0.5 mol% or more, more preferably 1.0 mol% or more, and even more preferably 1.5 mol% or more, relative to the total amount of active ingredients. The upper limit is preferably 10 mol% or less, more preferably 9 mol% or less, and even more preferably 8 mol% or less, 7 mol% or less, 6 mol% or less, and 5 mol% or less.

[0019] The KNA content is preferably 3 mol% or more, more preferably 7 mol% or more, even more preferably 9 mol% or more, 13 mol% or more, 16 mol% or more, and even more preferably 17 mol% or more, relative to the total amount of active ingredients. The upper limit is preferably 55 mol% or less, more preferably 54 mol% or less, even more preferably 53 mol% or less, 52 mol% or less, 51 mol% or less, and 50 mol% or less.

[0020] The α-KA content is preferably 1 mol% or more, 2 mol% or more, more preferably 3 mol% or more, and even more preferably 4.5 mol% or more, and 4.7 mol% or more, relative to the total amount of active ingredients. The upper limit is preferably 20 mol% or less, more preferably 19 mol% or less, and even more preferably 18 mol% or less, 17 mol% or less, 16 mol% or less, and 15 mol% or less.

[0021] In addition to the above-mentioned components, the active ingredient preferably further contains kessyl glycol diacetate (KGD: formula (2)).

[0022] [ka]

[0023] The KGD content is preferably 35 mol% or more, more preferably 36 mol% or more, even more preferably 37 mol% or more, 38 mol% or more, or 39 mol% or more, relative to the total molar amount of the active ingredients. The upper limit is preferably 95 mol% or less, more preferably 94 mol% or less, even more preferably 93 mol% or less, 92 mol% or less, or 91 mol% or less.

[0024] When the active ingredients include KGD and KNA, the values ​​calculated by the following formula are preferably 130% or less, 120% or less, 110% or less, or less than 100%, more preferably 99% or less, and even more preferably 98% or less, 97% or less, 96% or less, or 95% or less. Relative serotonin uptake (%) = -440 × log[KNA concentration (μM)] - 327 × log[KGD concentration (μM)] + 122 × log[KNA concentration (μM)] × log[KGD concentration (μM)] + 1259

[0025] When the active ingredients include KGD and KNA, the KGD:KNA (weight ratio) is preferably 1 to 20:1, more preferably 2 to 19:1, and even more preferably 3 to 18.5:1.

[0026] The total amount of active ingredients is usually 800 μM or more, preferably 850 μM or more, more preferably 900 μM or more, and even more preferably 950 μM or more.

[0027] Furthermore, the active ingredient preferably satisfies one of the following conditions (A) to (C). This allows for better serotonin reuptake inhibitory activity. (A) The molar ratio of KNA / (canocol + α-KA) is 0.5 or higher, 0.6 or higher, 1.0 or higher, 1.3 or higher, 1.5 or higher, or 4.5 or higher. (B) The KNA content relative to the active ingredient content is 3 mol% or more, preferably within the range described above. (C) The α-KA content relative to the active ingredient content is 1% or more, preferably within the range described above.

[0028] [Processed products from plants of the Valerian genus as raw materials / active ingredients] The raw materials for canocol, KNA, α-KA, and KGD may be either naturally derived or artificially synthesized, but naturally derived materials are preferred, and preferably derived from plants of the genus Valerian. The definition of plants of the genus Valerian is as explained above. Furthermore, serotonin uptake inhibitors may further contain processed products of plants of the genus Valerian as active ingredients. The definition of processed products is also as explained above, and examples include the extract of the genus Valerian mentioned above, and fractions of the hexane layer of said extract.

[0029] [Serotonin reuptake inhibitory activity] In this specification, confirmation of serotonin reuptake inhibitory activity can be confirmed by a test using human embryonic kidney cells 293 (HEK293 cells) transiently expressing recombinant human serotonin transporter (hSERT), as shown in the examples below.

[0030] [Daily intake] The recommended daily dose of serotonin reuptake inhibitors (for adults, once a day) is 10 mg or more of the active ingredient, preferably 12 mg or more, and more preferably 15 mg or more.

[0031] [Dosage form] Dosage forms of serotonin reuptake inhibitors include, for example, tablets, liquids, syrups, capsules, powders (granules, fine granules), soft capsules (soft capsules such as gelatin-based capsules), hard capsules, liquids, syrups, solids, semi-liquids, creams, and pastes, and the appropriate form should be selected according to the administration method.

[0032] [Administration Method / Target Patients] The drug is usually administered orally. The target of administration can be any animal, including humans, but is usually humans. While healthy individuals may be the target of administration, patients with disorders accompanied by anxiety or depressive symptoms (e.g., depression, bipolar disorder, panic disorder, social anxiety disorder, agoraphobia, obsessive-compulsive disorder, post-traumatic stress disorder (PTSD), depersonalization disorder, eating disorders, etc.) or healthy individuals suspected of having these disorders are preferred, and patients who have developed depression are even more preferred. Examples of non-human animals include mammals such as mice, rats, hamsters, dogs, cats, sheep, goats, cows, pigs, and monkeys. Serotonin reuptake inhibitors may consist solely of the above-mentioned active ingredients, or they may be in the form of a so-called composition containing other ingredients as needed. Examples of other ingredients include oily components, excipients, disintegrants, binders, lubricants, medicinal ingredients, coating agents, colorants, color fixatives, flavoring agents, antioxidants, preservatives, flavoring agents, acidulants, sweeteners, fortifiers, leavening agents, thickeners, surfactants, ingredients other than compounds having a 2-ethylhexyl structure that have a blood glucose elevation inhibitory effect and / or a glucose uptake promoting effect, anti-inflammatory agents, amino acids, vitamins, cooling agents, fragrances, sweeteners, abrasives, binders, pH adjusters, chelating agents, astringents, plant extracts, UV absorbers, humectants, solvents, seasonings, and food ingredients (including food additives). Optional ingredients may be selected according to the type of food and dosage form, and may be one type or a combination of two or more types.

[0033] The agent of the present invention can be used as a food composition, a pharmaceutical, a quasi-drug, or a cosmetic. Examples of food compositions include processed foods such as beverages (soft drinks, carbonated drinks, nutritional drinks, powdered drinks, fruit drinks, milk drinks, jelly drinks, etc.), confectionery (cookies, cakes, gum (chewing gum), candy, soft candy, tablets, gummies, lozenges, steamed buns, yokan, pudding, jelly, ice cream, sherbet, etc.), processed seafood (kamaboko, chikuwa, hanpen, etc.), processed livestock products (hamburgers, ham, sausages, wieners, cheese, butter, yogurt, fresh cream, cheese, margarine, fermented milk, etc.), soups (powdered soups, liquid soups, etc.), staple foods (rice, noodles (dried noodles, fresh noodles), bread, cereals, etc.), and seasonings (mayonnaise, shortening, dressings, sauces, dips, soy sauce, etc.). Of these, confectionery is preferred, and gum, candy, soft candy, gummy candy, and lozenges are more preferred.

[0034] Examples of food compositions include those with specific uses such as health foods, functional foods, health supplements, nutritional supplements, foods for specified health uses, medical foods, foods for the sick, infant foods, foods for elderly care, and foods for the elderly.

[0035] [3. Method for manufacturing serotonin uptake inhibitors] The above-mentioned agent can be manufactured by a method that includes a step of mixing raw material components, including canocol, KNA, and α-KA, and KGD as needed. The mixing of raw material components may be carried out by adjusting the concentration (content) of each component in the processed product of Valerian plants to the desired concentration. The formulation method can be a known method depending on the dosage form. [Examples]

[0036] The present invention will be described in detail below with reference to examples. The following examples are merely illustrative of the present invention and are not limited to these examples. Generally, "Kanokosou" is a polysemous term that refers to the plant genus, the plant itself, and the crude drug. However, in the following examples, the crude drug "Kanokosou," that is, the roots and rhizomes of the plant "Kanokosou," were used.

[0037] Example 1 [Isolation of each component from Valerian] A sample (chopped) of Valerian from Mie Prefecture was immersed in three times its volume of 99.5% ethanol at room temperature for 48 hours. This was repeated twice to obtain an ethanol extract (cold ethanol maceration) of Valerian. The obtained cold ethanol maceration extract (39 g, equivalent to 1.0 kg of the original Valerian) was mixed with hexane (500 ml) and H2O (250 ml), and the hexane layer was collected. Hexane was added to the aqueous layer, and the same procedure was repeated twice. Sodium sulfate was added to the hexane layer to remove water, and the mixture was dried under reduced pressure to obtain the hexane fraction. The hexane fraction was filtered through a glass filter and eluted with hexane / ethyl acetate (8:2), separating the filtrate from the residue. The filtrate was subjected to silica gel column chromatography, and fraction AH was obtained by elution with hexane / ethyl acetate (8:2 → 2:8), followed by ethanol. The compounds in each fraction were identified by normal-phase thin-layer chromatography (TLC) with hexane / ethyl acetate (8:2), (6:4), or (5:5), and stained with anisaldehyde-sulfuric acid solution. Fraction D was a single spot, yielding KGD. Fraction B was further subjected to silica gel column chromatography and fractionated by elution with hexane / diethyl ether (7:3 → 2:8) followed by diethyl ether. The compounds were developed by normal-phase TLC with hexane / diethyl ether (5:5), and confirmed by UV 254nm irradiation or staining with anisaldehyde-sulfuric acid solution to obtain the main spot BF (Rf=0.39). BF was further separated by HPLC (Alliance HPLC, Waters) using a preparative column Develosil ODS-7 (8i.d. × 250 mm, 7 μm, Nomura Chemical), and α-KA (28.9 min), KNA (31.5 min), and kanokol (40.7 min) were isolated. Analytical conditions: Column temperature, 40°C; detection wavelength, 198 nm; mobile phase, linear gradient elution system of water (A) and acetonitrile (B), flow rate 2 ml / min, 55% B (0-3 min), increasing from 55% to 65% (3-50 min). These analyses confirmed the presence of KNA, kanokol, α-KA, and KGD in the samples. Of these, kanokol was a novel compound previously unknown. The concentrations were 260 μM, 90 μM, 70 μM, and 1200 μM, respectively.

[0038] Example 2 [Serotonin uptake effect of valerian extract] Human Embryonic Kidney cells 293 (HEK293 cells) transiently expressing recombinant human serotonin transporter (hSERT) were treated with ethanol extract of Valerian (ethanol cold maceration: amount shown in Figure 1) obtained by the same method as in Example 1, and a radioisotope ( 3Serotonin (10 nM) labeled with H) was dissolved in Krebs-Ringer's-Hepes (KRH) buffer supplemented with 5% acacia gum and 0.015% olive oil, added, and incubated at 37°C for 10 minutes. After aspirating and removing the buffer, cells were lysed with 0.1 M NaOH / 0.5% SDS solution, neutralized with 0.1 M HCl, and radioactivity was measured using a liquid scintillation counter to determine serotonin uptake. Serotonin uptake was measured similarly except that KGD alone (amount shown in Figure 2(a)) or KGD and valerian ethanol fraction (hexane layer of ethanol extract fractionated by open column: amount shown in Figure 2(b)) was added instead of valerian ethanol extract (Figures 2(a) and (b)). Serotonin uptake was measured similarly for mock cells and control HEK293-hSERT cells, except that they were treated with a buffer without the sample. Sertraline (0.6 μM) was used as a positive control.

[0039] The introduction of hSERT increased serotonin uptake, but the addition of valerian ethanol extract decreased serotonin uptake in a concentration-dependent manner (Figure 1). Furthermore, KGD, the main component of valerian, does not have serotonin uptake inhibitory activity on its own (Figure 2a), but its activity was enhanced when combined with a fraction of valerian (Figure 2b).

[0040] Further fractionation of the valerian fraction by open column and HPLC yielded KNA, the novel compound kanokol, α-KA, and KGD (Equations 1-4). All of these compounds showed concentration-dependent serotonin uptake inhibitory activity (Figures 2 and 3).

[0041] Example 3 [Investigation of the mixing ratio of each component] In Example 2, the addition of KGD increased the serotonin uptake inhibitory effect of the valerian fraction, suggesting that compounds in valerian may be interacting with KGD to exert their activity. Therefore, based on a Definitive Screening Design (DSD), the activity of 13 combinations of the four activity-related compounds, mixed in amounts actually contained in valerian extract, or twice or half of those amounts (Table 1), was evaluated, and their interactions were examined. Sample 13 was prepared by mixing the four compounds according to the content ratios of KNA, kanokol, α-KA, and KGD contained in the valerian ethanol extract (ethanol cold maceration: 40 mg / ml of valerian) used in Examples 1 and 2 (260, 90, 70, and 1200 μM, respectively).

[0042] [Table 1]

[0043] [Footnotes for the table] The percentages in the table represent the content of each component relative to the total of the four components.

[0044] The serotonin uptake levels in each individual study were shown as a percentage of the control group (a group of hSERT-introduced HEK293 cells without sample addition), and further shown as a relative amount to the value for sample 13. Regression analysis revealed that the serotonin uptake inhibitory effect of Valerian is due to the interaction between KNA and KGD, and the following regression equation was obtained to predict the interaction.

[0045] (Regression equation) Relative serotonin uptake (%) = -440 × log[KNA concentration (μM)] - 327 × log[KGD concentration (μM)] + 122 × log[KNA concentration (μM)] × log[KGD concentration (μM)] + 1259

[0046] As a result, in all samples, the predicted value calculated by the above regression equation was 130% or less, and the difference between the predicted value and the actual value was r 2A correlation of 0.79 was observed (Figure 4), clearly indicating that serotonin uptake actually decreased, demonstrating an inhibitory effect.

[0047] Since this regression equation was obtained under conditions where kanokol and α-KA were also present, we evaluated the activity of each compound by mixing them sequentially in amounts found in valerian. As a result, the activity was enhanced by mixing KNA and KGD, supporting the regression equation. Further enhancement of activity was achieved by adding kanokol, but there was no change with the addition of α-KA (Figure 5).

[0048] This revealed that components such as canocol, α-KA, and KNA can exert serotonin reuptake inhibitory activity, and that this activity can be further enhanced by adjusting the amount of each component.

Claims

1. A compound represented by formula (1). 【Chemistry 1】

2. The compound described in claim 1, or The compound described in claim 1 and one or more selected from the group consisting of canoconyl acetate and α-kesyl acetate, It contains a serotonin reuptake inhibitor as an active ingredient.

3. A serotonin reuptake inhibitor according to claim 2, comprising the compound described in claim 1, canoconyl acetate, and α-kessyl acetate as active ingredients, and satisfying any of the following conditions. (A) The molar ratio of the canoconyl acetate content to the total amount of the compound described in claim 1 and α-kesyl acetate is 0.5 or more. (B) The canoconyl acetate content relative to the active ingredient content is 3 mol% or more. (C) The content of α-kesyl acetate relative to the content of the active ingredient is 1 mol% or more.

4. The agent according to claim 2 or 3, further comprising kesyl glycol diacetate as an active ingredient.

5. The serotonin reuptake inhibitor according to claim 4, wherein the value calculated by the following formula is 130% or less. Relative serotonin uptake (%) = -440 × log [concentration of canoconyl acetate (μM)] - 327 × log [concentration of kesyl glycol diacetate (μM)] + 122 × log [concentration of canoconyl acetate (μM)] × log [concentration of kesyl glycol diacetate (μM)] + 1259

6. The agent according to claim 4, wherein the ratio of kesyl glycol diacetate to canoconyl acetate (by weight) is 1 to 20:

1.

7. The agent according to claim 2 or 3, wherein the active ingredient content is 800 μM or more.

8. The agent according to claim 2 or 3, wherein the active ingredient is derived from at least a part of a plant of the genus Valerian or a processed product thereof.

9. The agent according to claim 8, wherein the plant of the genus Valeriana is one or more selected from Valeriana fauriei, Valeriana verna, Valeriana japonica, Valeriana sylvestris, and Valeriana lisianthus.

10. The agent according to claim 8, wherein the processed product is an alcohol extract of the plant body or a part thereof of a plant of the genus Valerian.

11. The processed product is the agent according to claim 8, comprising 0.8% by weight or more of kesyl glycol diacetate.

12. A method for producing a serotonin uptake inhibitor, comprising the step of mixing the compound described in claim 1 with a raw material component containing canoconyl acetate and / or α-kessyl acetate.

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