WO2007013581A1

WO2007013581A1 - Sedative composition

Info

Publication number: WO2007013581A1
Application number: PCT/JP2006/314958
Authority: WO
Inventors: Yasuyuki Hasegawa
Original assignee: Kobayashi Pharmaceutical Co., Ltd.
Priority date: 2005-07-28
Filing date: 2006-07-28
Publication date: 2007-02-01

Abstract

[PROBLEMS] To provide a sedative composition which has an excellent sedative effect on the mind of a person or animal and a sleep-improving composition which can improve the sleep quality to induce good sleeping. [MEANS FOR SOLVING PROBLEMS] A sedative composition or sleep improving composition comprising a compound represented by the general formula (1): (1) wherein R1 to R7 independently represent a hydrogen atom, a hydroxyl group or a methyl group; R8 and R9 independently represent a hydrogen atom or a methyl group; A represents an ethylene or vinylene group; and n represents an integer of 0 to 10.

Description

Specification

Sedative composition

Technical field

[0001] The present invention relates to a sedative composition. More specifically, the present invention relates to a sedative composition that excels in the action of calming the spirit of humans and animals.

Background art

[0002] In recent years, aroma therapy using various plant-derived essential oil components has attracted attention as a means of reducing mental adverse effects due to stress and the like and calming the mind. In particular, among essential oils that exhibit a sedative effect, sandalwood oil is excellent in the effect of improving sleep and is useful as a sedative fragrance (see, for example, Patent Documents 1 and 2).

[0003] However, sandalwood has been rapidly decreasing in number in recent years due to overcutting, and sandalwood oil produced from the plant moss has been steadily decreasing. With such a decrease in the production of sandalwood oil, the development of synthetic compounds exhibiting the same scent as sandalwood oil is being energetically promoted today. On the other hand, the sedative effect of sandalwood oil has no direct causal relationship with the smell of smelled sandalwood oil, and it is a compound that exhibits the same or similar scent as sandalwood. However, there is no analogy about the presence or absence of the sedative effect. For this reason, it is quite clear what kind of structure of a synthetic compound that has the same or similar scent as sandalwood can be used to obtain a sedative effect or sleep improvement effect! The current situation is Tatsuno.

Patent Document 1: Japanese Patent Laid-Open No. 7-316582

Patent Document 2: Japanese Patent Publication No. 7-57734

Disclosure of the invention

Problems to be solved by the invention

[0004] An object of the present invention is to provide a composition for sedation which is excellent in the action of sedating a human or animal spirit.

Means for solving the problem [0005] The present inventors diligently studied to solve the above-mentioned problems. As a result, the compound represented by the following general formula (1) exhibits a scent that is the same as or close to that of sandalwood and calms the mind. It was found to be excellent in the action of inducing sleepiness and inducing sleep. The present invention has been developed through further studies based on such knowledge.

That is, the present invention provides the following inventions:

Item 1. Compound represented by general formula (1)

[0007] [Chemical 1]

[Wherein, R to R are the same or different and each represents a hydrogen atom, a hydroxyl group or a methyl group;

8 and R

9 is the same or different and represents a hydrogen atom or a methyl group;

A represents an ethylene group or a beylene group, and n represents an integer of 0 to 10]

A sedative composition comprising: a sedative composition.

Item 2. —The composition for sedation according to Item 1, wherein in General Formula (1), at least three of R to R are acetyl groups.

Item 3. — In the general formula (1), R to R are all methyl groups, and R to R are all hydrogen atoms.

1 3 4 7

Item 2. The sedative composition according to Item 1.

Item 4. In the general formula (1), either one or both of R and R are acetyl groups.

8 9

Item 2. A sedative composition according to Item 1.

Item 5. —The sedative composition according to Item 1, wherein n is 0 to 2 in the general formula (1).

Item 6. — In general formula (1), R to R are all methyl groups, and R to R are all hydrogen atoms.

1 3 4 7

Item 2. The sedation according to Item 1, wherein one or both of R and R are acetyl groups.

8 9

Composition.

Item 7. —The compound represented by the general formula (1) is

R ~ R cation group, R ~ R is hydrogen atom, R force S methyl group, R is hydrogen atom, A is ethyl

1 3 4 7 8 9

A compound wherein n is 0, R ~ R cation group, R ~ R is hydrogen atom, R force S methyl group, R is hydrogen atom, A is beryl

1 3 4 7 8 9

A group wherein n is 0, or

R ~ R force S methyl group, R ~ R is hydrogen atom, R and R force S methyl group, A is beylene group,

1 3 4 7 8 9

n is 0

Item 2. The sedative composition according to Item 1.

Item 8. In the sedative composition, the ratio of the compound represented by the general formula (1) to the total amount of the compound represented by the general formula (1) and the fragrance component is 10% by weight or more. Item 8. A sedative composition according to any one of items 1 to 7,

Item 9. The sedative composition according to any one of Items 1 to 8, which is in the form of a fragrance, a cosmetic, an inhalation agent, a textile detergent, or a food.

Item 10. —Compound represented by formula (1)

[0009] [Chemical 2]

[Wherein R to R are the same or different and each represents a hydrogen atom, a hydroxyl group or a methyl group,

R and R are the same or different and each represents a hydrogen atom or a methyl group,

8 9

A represents an ethylene group or a beylene group,

n represents an integer of 0 to 10]

A composition for improving sleep, comprising:

Item 11. The sleep improving composition according to Item 10, wherein, in General Formula (1), at least three of R to R are methyl groups.

Item 12. —In the general formula (1), R to R are all methyl groups, and R to R are all hydrogen atoms.

1 3 4 7

Item 11. The composition for improving sleep according to Item 10, which is a child.

Item 13. —In the general formula (1), either one or both of R and R are acetyl groups.

8 9

Item 11. The composition for improving sleep according to Item 10.

Item 14. The composition for improving sleep according to Item 10, wherein n force ^ -2 in the general formula (1). Item 15. —In the general formula (1), R to R are all methyl groups, and R to R are all hydrogen atoms.

1 3 4 7

The sleep according to Item 10, wherein any one or both of R and R are acetyl groups.

8 9

Composition for improvement.

Item 16. —The compound represented by the general formula (1) is

1 3 4 7 8 9

A compound wherein n is 0,

R ~ R cation group, R ~ R is hydrogen atom, R force S methyl group, R is hydrogen atom, A is beryl

1 3 4 7 8 9

A group wherein n is 0, or

1 3 4 7 8 9

n is 0

Item 11. The composition for improving sleep according to Item 10, wherein

Item 17. In the composition for improving sleep, the ratio of the compound represented by the general formula (1) to the total amount of the compound represented by the general formula (1) and the fragrance component is 10% by weight or more. Item 17. The composition for improving sleep according to any one of Items 10 to 16.

Item 18. The sleep improving composition according to any one of Items 10 to 17, which is in the form of a fragrance, a cosmetic, an inhalation agent, a textile detergent, or a food.

[0011] Hereinafter, the present invention will be described in detail. In the present invention, the “sedative composition” is used to relax or improve sleep by soothing the mind of a human or animal. In the present invention, the “sleep improvement composition” refers to a good sleep state that induces sleep by improving sleepiness when waking up, smoothing sleep, reducing arousal during sleep, etc. Is used to guide

[0012] The sedative composition of the present invention is characterized by containing a compound of the following general formula (1).

[0013] [Chemical 3]

In the formula, I ^ to R ₇ are the same or different and are a hydrogen atom, a hydroxyl group or a methyl group, preferably a hydrogen atom or a methyl group. In the compound of the general formula (1), at least three of R to R are preferably acetyl groups, particularly R methyl group and R

1 ~ R are all

3 4

All of ~ R are preferably hydrogen atoms.

[0015] In the formula, R and R are the same or different and each represents a hydrogen atom or a methyl group. General

8 9

In the compound of the formula (1), either one or both of R and R are S methyl groups.

8 9

Is desirable.

In the formula, A represents an ethylene group (CH 2 —CH 2) or a beylene group (CH═CH).

[0017] In the formula, n is an integer of 0 to 10. In the compound of the general formula (1), preferably n is

0 to 2, more preferably n is 0 or 1, and particularly preferably n is 0.

[0018] Among the compounds of the general formula (1) used in the present invention, as specific examples of suitable compounds,

1 3 4 7 8 9

And a compound in which n is 0 (ie, 3-methyl-5- (2,2,3-trimethyl-3-cyclopenten-1-yl) -pentan-2-ol);

1 3 4 7 8 9

And a compound in which n is 0 (ie 3-methyl-5- (2,2,3-trimethyl-3-cyclopenten-1-yl) -4-penten-2-ol);

R ~ R force S methyl group, R ~ R is hydrogen atom, R and R force S methyl group, A is beylene group, and

1 3 4 7 8 9

A compound that has n force ^ (ie 3,3-dimethyl-5- (2,2,3-trimethyl-3-cyclopenten-1-yl) -4-penten-2-ol)

Is exemplified.

The compound represented by the general formula (1) is a known compound or a compound that is easily derived from a known compound power. The compound represented by the general formula (1) is produced by various known synthetic methods depending on the basic skeleton, the type of substituents, and the like.

[0020] For example, the compound represented by the general formula (1) is a compound represented by the following general formula (2) (wherein R

~ R and n are the same as described above) and an appropriate aldehyde or ketone is subjected to aldol condensation under appropriate conditions, and further reduced under appropriate conditions.

[0021] [Chemical 4]

[0022] Further, the compound represented by the general formula (2) used as the raw material mixture of the compound represented by the general formula (1) is a known compound or a compound easily derived from the known compound. is there. For example, the compound represented by the general formula (2) is camphorolenal (campholenicaldehyde; a compound in which R to R force S methyl group, R to R is hydrogen atom, n force SO in general formula (2)) Even if

1 3 4 6

For example, a pinene (α-pinene) can be epoxidized, and the resulting epoxide can be reacted in the presence of ZnBr under appropriate conditions.

[0023] In the sedative composition of the present invention, as the compound represented by the general formula (1), one compound may be used alone, or two or more compounds may be used in any combination. You can do it.

[0024] The compound represented by the general formula (1) includes a compound that itself exhibits a sandalwood fragrance. In the sedation composition of the present invention, in addition to the compound represented by the general formula (1), a component exhibiting aroma such as an essential oil component or a synthetic fragrance obtained from natural plants and animals by an existing extraction method (hereinafter referred to as a fragrance composition) , "Denoted as" perfume ingredient "). However, in such a case, in the sedation composition of the present invention, the total amount of the compound represented by the general formula (1) and the fragrance component (fragrance components other than the compound represented by the general formula (1)). On the other hand, the compound represented by the general formula (1) is preferably 10% by weight or more, preferably 40% by weight or more, and more preferably 70% by weight or more. By using the compound represented by the general formula (1) at such a ratio, the effects of the present invention can be made remarkable.

[0025] The sedative composition of the present invention may be composed of only the compound represented by the general formula (1), but depending on the form of use, it may be a carrier, a substrate, an additive, or the like. Other components may be contained. In the sedation composition of the present invention, the ratio of the compound represented by the general formula (1) depends on the use form of the composition, the degree of expected effect, the gender and age of the user, etc. Although different, for example, the ratio of the compound represented by the general formula (1) to 0.01 to L00% by weight, preferably 0.05 to 80% by weight, with respect to the total weight of the composition. Is The

[0026] The form of the sedative composition of the present invention is not particularly limited as long as the compound represented by the general formula (1) is prepared so as to be inhaled or absorbed. Specific examples of the form of the sedative composition of the present invention include fragrances, cosmetics, inhalation administration agents, textile detergents, foods and the like. Preferred are fragrances, cosmetics, inhalation administration agents, and textile products, and more preferred are fragrances and cosmetics.

[0027] Examples of the fragrances include those for which conventional power is also used as fragrances, such as for bedrooms, living rooms, toilets, entrances, bathrooms, closets, and chiffons. The form of the fragrance is not limited, and various forms such as a solid form, a semi-solid form (jelly form, gel form, etc.), a liquid form, and an aerosol form are used. In addition, the fragrance may be used by spontaneously evaporating the compound represented by the general formula (1), or the compound may be evaporated by heating. In particular, if the compound represented by the general formula (1) is poor in volatility, it is desirable to evaporate by heating.

[0028] When the sedative composition of the present invention is used in the form of a fragrance, the sedative composition of the present invention is conventionally used as a fragrance in addition to the compound represented by the general formula (1). Ingredients such as the base, support, additive, etc., can be contained. Examples of the base compounded in the fragrance include water, ethanol, solid or liquid anionic, cationic, nonionic active agent, polymer agent, fats and oils, guar gum, xanthan gum, gum arabic, and dielan gum. Carrageenan, gelatin, agar, water-insoluble solvent, wax, petrolatum, lanolin and the like.

[0029] When the sedative composition of the present invention is in the form of a fragrance, a particularly suitable blending ratio of the compound represented by the general formula (1) is represented by the general formula (1) in the composition. The proportion of the compound is 5 to 80% by weight, more preferably 40 to 60% by weight.

[0030] In addition to cosmetics, cosmetics include biological cleaning agents such as sarcophagus, bathing agents, and the like. Specific examples of cosmetics include creams, milky lotions, cosmetic powders, body lotions, hair styling, hair shampoos, sarcophagus, body soaps, antiperspirants, shampoos, rinses, perfumes, lotions, toothpastes, liquid toothpastes, washing Examples include mouth preparations, mouse pets, sunscreens, kitchen detergents, massage oils, massage creams, skin care oils, and the like. When the sedative composition of the present invention is made into a cosmetic product, the sedative composition of the present invention is represented by the general formula (1). In addition to the compound, components such as bases and additives conventionally used in cosmetics can be contained. The base is not particularly limited, and examples thereof include water, ethanol, talc, gelatin, wax, petrolatum, and lanolin. The additive is not particularly limited, and examples thereof include humectants, skin softeners, preservatives, solubilizers, and fragrances.

[0031] When the sedative composition of the present invention is in the form of a fragrance, a particularly suitable blending ratio of the compound represented by the general formula (1) is represented by the general formula (1) in the composition. The proportion of the compound is 0.01 to 50% by weight, more preferably 0.05 to 10% by weight, and still more preferably 0.1 to 1% by weight.

[0032] An inhalation administration agent is a preparation in which the compound represented by the above general formula (1) is volatilized in the vicinity of the nose or applied to the nasal cavity to intentionally inhale the compound. Examples include nasal sprays, sprays, inhalation solutions, and masks carrying the compounds. When the sedation composition of the present invention is in the form of an inhalation administration agent, the sedation composition of the present invention has been conventionally used for an inhalation administration agent in addition to the compound represented by the general formula (1). Ingredients such as bases and additives can be included. In addition, when an inhalation gas is used, the gas that has been used in conventional inhalation administration agents can be used. Administration of the inhalation agent

Although not particularly limited, it is preferable to perform 1 to 10 times per day in 5 to 60 seconds per time. Although not limited, the inhalation administration agent is a compound power represented by the above general formula (1) in the inhaled gas at the time of use, usually 0.000001 ppm to 10 ppm, preferably O.OOOOlppm to 0.1 ppm, It is desirable to set appropriately so as to volatilize at a concentration of about 0.0001 ppm to 0.001 ppm.

[0033] Examples of textile detergents include anionic, cationic, nonionic or zwitterionic detergents, textile softeners, textile softeners, dryer textile softeners, and the like. Can be mentioned. When the sedative composition of the present invention is in the form of a detergent for textile products, the compound represented by the general formula (1) can be adhered to the textile product by washing the textile product, and the compound is adhered. Excellent sedation can be obtained through the use of textile products. When the sedation composition of the present invention is made into the form of a detergent for textile products, the sedation composition of the present invention includes a detergent for textile products in addition to the compound represented by the general formula (1). Other ingredients used in can be used. [0034] When the sedative composition of the present invention is made into a detergent for textile products, a particularly suitable blending ratio of the compound represented by the general formula (1) is as follows: The proportion of the compound represented is 0.01 to 10% by weight, more preferably 0.05 to 5% by weight.

[0035] Examples of foods include health foods, foods for sick people, foods for specified health use, and dietary supplements. Although not particularly limited, in order to obtain a sedative effect efficiently, the compound represented by the above general formula (1) is inhaled through the oral mucosa, staying in the mouth for a relatively long time, or tea. It is preferable that the compound represented by the general formula (1) volatilizes and is inhaled through the nasal mucosa before being put into the mouth, such as a flavoring agent. Specific examples of such foods include gums, teas, beverages, rice cakes, flavorings, spices, gummi, yogurt, ice cream, edible films and the like. When the sedative composition of the present invention is in the form of food, the sedative composition of the present invention is selected from the compounds represented by the above general formula (1) that are acceptable for food hygiene. It is prepared by blending as a component of food. The sedative composition of the present invention prepared in a food form is used as a sedative food or for sedation, to be used for promoting sleep, to be used for stress relief, Or it is useful as a food displayed to be used to improve sleep.

[0036] When the sedative composition of the present invention is made into a food form, a particularly suitable blending ratio of the compound represented by the general formula (1) is represented by the general formula (1) in the composition. The proportion of the compound is 0.01 to 10% by weight.

[0037] In addition to the above, the sedative composition of the present invention includes, for example, bedding such as futons and pillows; clothing; curtains; doors; screen doors; interior materials; On the other hand, there are those used in a mode in which the compound represented by the general formula (1) is sprayed or applied.

By using a powerful sedative composition, the compound represented by the general formula (1) is volatilized from various articles to which the compound represented by the general formula (1) is adhered. An excellent sedative effect can be obtained. Preferred examples of such forms include spray preparations, aerosol preparations, liquid, jelly-like or cream-like preparations, and those obtained by impregnating them with a nonwoven fabric.

The invention's effect [0038] The sedative composition of the present invention exhibits the same or similar scent as sandalwood and can exhibit an excellent mental sedative effect on humans and animals.

[0039] In addition to the excellent sedative effect, the sedative composition of the present invention also has an excellent sleep improving effect, fatigue recovery effect, stress relieving effect or relaxing effect. It is also useful as a fatigue recovery composition, a stress relaxation composition, or a relaxation composition. Among them, the sedative composition of the present invention is particularly useful as a sleep improving composition for inducing a good sleep state and inducing a good sleep state.

BEST MODE FOR CARRYING OUT THE INVENTION

Hereinafter, the present invention will be described with reference to examples, but the present invention is not limited to these examples.

麵 I

Using 5 healthy adults (3 males and 2 females) who are aware of mild insomnia as subjects, the evaluation test of the sedative effect of the compositions shown in Table 1 (Examples 1 and 3 and Comparative Examples 1 and 3) The following method was used. The compositions of Example 1-3 and Comparative Example 1-3 all have a sandalwood fragrance.

[0041] [Table 1]

Examples Comparative Examples Ingredients

1 2 3 1 2 3

3-Methyl-5- (2,2,3-trimethyl-3-cyclopent

Ten-zyl) -pentane-2-ol (in general formula (1)

1 ^ to 1¾ ₃ are methyl groups, R _{4 to} R ₇ are hydrogen

50

Atom, R ₈ is methyl group, R ₉ is hydrogen atom, A is

Tylene group and a compound in which n is 0): Trade name

"Sandalore", manufactured by Givaduan-Roure

3-methyl-5- (2,2,3-trimethyl-3-cyclopent

Ten-1-yl) -4-penten-2-ol (general formula (1)

In, 1 ^ to 1 ₃ is methyl, R ₄ ~ R ₇ water - 50 - - - atom, R ₈ is a methyl group, R ₉ is a hydrogen atom, A is

Yoshi Pinylene group and n is 0)

"Ebanol", made by Givaduan-Roure ft

3,3-dimethyl-5- (2,2,3-trimethyl-3-cyclo

Pentene-1-yl) -4-penten-2-ol (general)

In the formula (1), 1 ^ to 1 ₃ is methyl, R ₄ to R one - 50 - - - 7 are hydrogen atoms, R ₈ and R ₉ are methyl, A Gabi

Compound: Diylene group, and compound where n is 0): Product name

rp ₀ lysantol ", Fi device nich g¾

Isobornylcyclohexanol: Product name

-―-50--rsantalexj, manufactured by Takasago

2-Ethyl-4- (2,2,3-trimethyl-3-cyclopent

-2-buten-1-ol: Product name ― ―--50-"Bacdanol", manufactured by IFF

2-Methyl-4- (2,2,3-trimethyl-3-cyclopent

Ten-1-yl) -2-Buten-1-ol: Product name 50 “SandalDiysore corej, manufactured by Kao

Propylene glycol 50 50 50 50 50 50 Material

Yaki + 100 100 100 100 100 100 In the table, the unit is% by weight. Each subject was put to sleep in a bedroom where the aromatic compounds contained in the composition shown in Table 1 were volatilized. From 1 hour before bedtime of each subject, put felt (35mm long, 15mm wide, 2mm thick; made of pulp) impregnated with 0.5g of fragrance composition on a hot fragrance hot plate. adjust the temperature to 80 ° C were allowed to volatilize fragrance compound into the bedroom, adjusted so that is held constant at a concentration of about 5 X 10- ⁴ ppm aromatic I匕合was in the bedroom during sleep I kept it. The subjects put a micromini R'R type actigraph (manufactured by AMI, USA; obtained from Satani Shoji Co., Ltd.) on their non-dominant arm at the time of going to bed, and measured and digitized the minute movements of the sleeping body. . Also, together with “Yuka Yamamoto et al., Development and standardization of OSA sleep questionnaire (MA version) for middle-aged and elderly, elderly people”, Brain and Psychiatry, 10th, 4th, 1999, In accordance with the method reported in Section 401-409, subjects were asked to make a judgment on each item of the OSA sleep schedule. Each factor of recovery and sleep time was evaluated.

[0043] As a control, instead of the composition shown in Table 1, only propylene glycol (Control 1) or a composition containing 50% by weight of sandalwood oil (produced from Indomysole) and 50% by weight of propylene glycol (Control 2) ) And evaluated as above.

[0044] The obtained results are shown in Figs. Figures 1 to 3 show the results of the compositions of Examples 1 to 3, respectively; Figures 4 to 6 show the results of the compositions of Comparative Examples 1 to 3, respectively. In Figs. 1-6, A shows the amount of activity during sleep (average value of 5 subjects) (unit: actigraph count) measured by micromini R'R type actigraph; Shows the results of quantification of each factor of sleepiness at sleep, sleep onset and sleep maintenance, dream, recovery from fatigue, and sleep time based on the judgment results of each item of the OSA sleep questionnaire (average value of 5 subjects) Indicates. In A of each figure, the greater the amount of activity during sleep, the less sleep, and in B of each figure, the greater the numerical value of each item, the better the sleep state.

[0045] As shown in FIGS. 1 to 3, when the compositions of Examples 1 to 3 are used, the amount of activity during sleeping is similar to or less than that of sandalwood oil, and has excellent mental sedation. It was confirmed that the effect of inducing sleep or relaxing was exerted. A similar trend was also confirmed in the OSA sleep survey results. In particular, from the results of the OSA sleep survey, it was found that the compositions of Examples 1 to 3 were excellent in fatigue recovery action. On the other hand, as shown in FIGS. 4 to 6, the compositions of Comparative Examples 1 to 3 have the effect of calming the mind and sleep even though they exhibit the same sandalous fragrance as the compositions of Examples 1 to 3. It was confirmed that there was no action to improve.

[0046] Example 4

A cosmetic product (cream) having the following composition was prepared according to a conventional method.

Unit:% by weight

3,3-dimethyl-5- (2,2,3-trimethyl

-3-Cyclopentene-1-yl) -4-penten-2-ol 0.10

1,3-Butyleneglycanol 3.00

Carboxyvinyl polymer (trade name “Carbopol 980”, BF Goodrich) 0.20

Polyoxyethylene monostearate

(Product name "IONET T-60C", manufactured by Sanyo Chemical) 4.70

Stearic acid 1.00

Cetyl palmitate 2.00

Behenorenorecall 3.00

Tri-2-Ethylhexanoic acid glyceryl 5.00

Skull 10.00

Sodium hydroxide appropriate amount

Methylparaben appropriate amount

Paraxybenzoic acid ester

Purified water m _

Total 100.00% by weight

Example 5

Instead of 3,3-dimethyl-5- (2,2,3-trimethyl-3-cyclopenten-1-yl) -4-penten-2-ol, 3-methyl-5- (2,2,3 A cosmetic (cream) was prepared with the same composition as in Example 4 except that -trimethyl-3-cyclopenten-1-yl) -pentane-2-ol was used.

[0048] Example 6

Instead of 3-methyl-5- (2,2,3-trimethyl-3-cyclopenten-1-yl) -4-penten-2-ol, 3-methyl-5- (2,2,3-trimethyl A cosmetic (cream) was prepared with the same composition as in Example 4 except that -3-cyclopenten-1-yl) -pentane-2-ol was used.

Brief Description of Drawings

[0049] Fig. 1 shows the results of evaluating the mental sedation effect and sleep improvement effect of the composition of Example 1 in Test Example 1. A shows the amount of sleep activity (vertical axis; unit is the number of actigraph counts) measured by micromini R'R type actigraph; B shows the judgment result of each item of the OSA sleep survey form Based on sleepiness, wakefulness, sleep and sleep maintenance, dream, fatigue The numerical results (vertical axis; judgment value) for each factor of recovery and sleep time are shown.圆 2] In Test Example 1, the results of evaluating the mental sedation effect and sleep improvement effect of the composition of Example 2 are shown. Items displayed by A and B in the figure are the same as those in Figure 1.

圆 3] In Test Example 1, the results of evaluating the mental sedation effect and sleep improvement effect of the composition of Example 3 are shown. Items displayed by A and B in the figure are the same as those in Figure 1.

4) The results of evaluating the mental sedation effect and sleep improvement effect of the composition of Comparative Example 1 in Test Example 1. Items displayed by A and B in the figure are the same as those in Figure 1.

圆 5] The results of evaluating the mental sedative effect and sleep improving effect of the composition of Comparative Example 2 in Test Example 1. Items displayed by A and B in the figure are the same as those in Figure 1.

6) The results of evaluating the mental sedation effect and sleep improvement effect of the composition of Comparative Example 3 in Test Example 1. Items displayed by A and B in the figure are the same as those in Figure 1.

Claims

Claims Compounds represented by general formula (1)

[Chemical 1]

[Wherein, ~ are the same or different and each represents a hydrogen atom, a hydroxyl group or a methyl group,

8 9

A represents an ethylene group or a beylene group,

n represents an integer of 0 to 10]

A sedative composition comprising: a sedative composition.

[2] The compound represented by the general formula (1) is

1 3 4 7 8 9

A compound wherein n is 0,

1 3 4 7 8 9

A group wherein n is 0, or

1 3 4 7 8 9

n is 0

The composition for sedation according to claim 1, wherein

[3] The sedative composition according to claim 1 or 2, which is in the form of a fragrance, a cosmetic, an inhalation agent, a textile detergent, or a food.

[4] Compound represented by general formula (1)

[Chemical 2]

8 9

A represents an ethylene group or a beylene group,

n represents an integer of 0 to 10]

A composition for improving sleep, comprising:

[5] The compound represented by the general formula (1) is

1 3 4 7 8 9

A compound wherein n is 0,

1 3 4 7 8 9

A group wherein n is 0, or

1 3 4 7 8 9

n is 0

The sleep improving yarn and adult product according to claim 4, wherein

6. The composition for improving sleep according to claim 4 or 5, which is in the form of a fragrance, a cosmetic, an inhalation agent, a textile detergent, or a food.