JPH10204473A - Modified valerian root oil and its production - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject oil capable of developing fruity and woody aroma while retaining sedative effect without unpleasant odor and useful for cosmetics, products, etc., for oral cavities by treating valerian root oil containing a fatty acid with an alkali and removing the fatty acid. SOLUTION: (A) Valerian root oil [e.g. essential oil obtained by subjecting rhizome of Valeriana officinalis L., Valeriana fauriei forma yezoensis, Valeriana wallichii D.C., etc., to steam distillation or solvent extraction] containing a fatty acid (A1 ) is subjected to alkali treatment to remove the component A1 . The modified valerian root oil is readily and inexpensively obtained in >=90% high yield by dissolving the component A in an ether, adding sodium hydrogen carbonate aqueous solution thereto to extract the component A1 , further adding sodium hydroxide aqueous solution thereto to extract the component A1 and drying the resultant ether layer with anhydrous magnesium sulfate, etc., and subjecting ether to distillation under reduced pressure.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a modified valerian oil and a method for producing the same, and more particularly to a method for modifying its fragrance.

[0002]

2. Description of the Related Art Valeriana belonging to the genus Valeriana of the family Valerianaceae (Valerianaceae)
aleriana officinalis L.) is Valerian
In Europe, the rhizome has been drunk as a sedative herb since ancient times. The essential oil (valerian oil) is extracted by steam distillation or solvent extraction. Valerian oil is known to have a sedative effect by inhalation, and is used for sedation in flavors and aromatherapy.

[0003] However, although valerian oil has a woody spicy scent as a whole, it has a peculiar unpleasant odor. Therefore, valerian oil has low palatability and improvement of its fragrance has been desired. As a method of improving the aroma of valerian oil, for example, a method has been reported in which valerian oil is distilled under reduced pressure to remove a low boiling point portion of 80 ° or less (Japanese Patent Application Laid-Open No. 1-254628).

[0004]

However, the method involves heating, which may lead to denaturation of fragrance components, especially components having a sedative effect, and cost problems since the yield is not so high. was there. The present invention has been made in view of the above-mentioned problems, and an object of the present invention is to improve the fragrance of valerian oil, in particular, it emits a well-balanced favorable odor without an unpleasant odor, and has a conventional valerian oil with a calming effect. It is an object of the present invention to provide a modified valerian oil having the same or higher quality and a method for easily and inexpensively producing such a modified valerian oil.

[0005]

Means for Solving the Problems The present inventors have conducted intensive studies in order to achieve the above object, and as a result, the sedative effect has been improved by treating valerian oil with alkali to remove acidic components such as fatty acids. The present inventors have found that a modified valerian oil whose scent alone has been remarkably improved without loss can be obtained in high yield, and have completed the present invention. That is, the modified valerian oil according to the present invention is characterized in that a fatty acid is removed from a valerian oil containing a fatty acid by an alkali treatment.

[0006] A method for producing a modified valerian oil according to the present invention is characterized in that a valerian oil containing a fatty acid is treated with an alkali to remove the fatty acid.
In the above-mentioned production method, it is preferable that an ether solution of valerian oil containing a fatty acid is sequentially extracted with an aqueous solution of sodium hydrogen carbonate and an aqueous solution of sodium hydroxide to remove the fatty acid and to remove the ether from the ether layer.

[0007]

BEST MODE FOR CARRYING OUT THE INVENTION The modified valerian oil according to the present invention can be obtained by removing acidic components containing fatty acids from valerian oil by alkali treatment. Valerian oil as a raw material of the modified valerian oil of the present invention includes Valeriana officinalis and Valeriana officinalis L. var.
known methods from rhizomes such as latifolia Miq. (V. japonica Makino)), Ezogiana (V. fauriei forma yezoensis), and Indian valerian (V. wallichii DC);
For example, an essential oil obtained by a method such as steam distillation or solvent extraction can be used. Also, essential oils extracted from these valerian and related species are valerian oil (Va
lerian oil), valerian oil, and Kesso root oi
l, Japanease valerian oil)
These can be used irrespective of the origin such as Japanese, Chinese and European origin. In any case, the valerian oil used as a raw material of the present invention contains at least one kind, usually several kinds or more of fatty acids, and particularly contains acetic acid and isovaleric acid.

In the method for producing the modified valerian oil of the present invention, first, such a fatty acid-containing valerian oil is dissolved in an organic solvent, preferably ether, and an alkali aqueous solution is added thereto to carry out an extraction operation to remove the fatty acid. The acidic components contained are extracted and removed. As the aqueous alkaline solution, any inorganic base or organic base can be used as long as it is generally used in an extraction operation, but an aqueous sodium hydrogen carbonate solution and an aqueous sodium hydroxide solution are preferable, and an aqueous sodium hydrogen carbonate solution is particularly preferable. After the extraction, it is preferable to further extract with an aqueous sodium hydroxide solution. After the obtained organic solvent layer is dried over anhydrous magnesium sulfate or the like, the organic solvent is distilled off under reduced pressure to obtain valerian oil from which fatty acids have been removed (modified valerian oil). According to the method of the present invention, a modified valerian oil can be obtained in a high yield of about 90% or more.

The modified valerian oil of the present invention has a fruity woody type good odor without any unpleasant odor. Moreover, the sedative effect is not impaired by the alkali treatment and has an effect equal to or higher than that of the valerian oil before the treatment. Therefore, according to the present invention, the palatability of valerian oil, which was low due to unpleasant odor, can be remarkably enhanced. Further, according to the present invention, such a modified valerian oil can be easily and inexpensively produced, and a highly useful modified valerian oil can be provided.

The modified valerian oil of the present invention can be used for any purpose that requires these effects for the purpose of perfuming and soothing effects. For example, fragrance products such as perfumes, aromatic products such as indoor air fresheners, creams, emulsions, cosmetic powders, body lotions, body oils, cosmetics such as body soaps, tonics,
Examples include, but are not limited to, hair products such as mousse, hair spray, shampoo, and rinse, deodorant products, oral products such as toothpastes and mouthwashes, and aerosol products. It is also useful as an aromatherapy or inhalation drug. In addition, since Valerian itself has been used orally as a crude drug having a sedative effect since ancient times, it is also conceivable to use it as an oral drug or food, or as a flavoring component thereof. Hereinafter, the present invention will be described in more detail with reference to specific examples, but the present invention is not limited thereto. In addition, each test method was performed according to the method mentioned later.

Table 1 below shows commercially available valerian oil (Valerian oil).
rian root oil) and modified valerian oil (Example 1 described later) obtained by treating the valerian oil with an alkali, by gas-liquid chromatography (GLC).
And gas chromatography-mass spectrometry (GC-MS)
Shows the results of the analysis.

Referring to Table 1, valerian oil contains a fatty acid such as acetic acid (7) in addition to isovaleric acid (peak No. 11). In contrast, in the modified valerian oil obtained by the alkali treatment, it is found that these fatty acids are completely removed. By the alkali treatment, the unpleasant odor of the valerian oil before the treatment was completely eliminated, and a fresh fruity woody type fragrance having a pine-like and transparent feeling was obtained. The alkali-treated valerian oil had a calming effect equal to or higher than that of the valerian oil before the treatment.

[0013]

[Table 1] ──────────────────────────────────── Peak area (%) * ──── ──────────────────── Valerian Oil Modified Valerian Oil Peak No. Ingredient (Before Treatment) １ 1 α-panene 9.19 8.00 2 camphene 17.46 18.59 3 β-panene 6.73 5.17 4 β-myrcene 0.41 0.29 5 limonene 2.83 2.16 6 p-cymene 0.84 0.76 7 acetic acid 0.25-8 α-terpanolene 0.24-9 l-phornyl acetate 29.35 34.24 10 β-caryophyllene 2.28 2.12 11 isovaleric acid 0.89-12 miltenyl acetate 0.61 0.59 13 l-phorneol 2.32 2.05 14 β- Pulsed water 0.58 0.54 15 ar-curcumene 4.85 4.66 16 Valeranone 1.10 1.18 ──── ─────────────────────────────── * In peak area, - it means undetectable.

[0014]

EXAMPLES Hereinafter, the present invention will be described in more detail by way of examples, but the present invention is not limited thereto. Example 1 Modified Valerian Oil by Alkali Treatment
Producing commercial valerian oil: it was dissolved (Valerian root oil Yamamoto fragrance Co.) by addition of diethyl ether 200ml to 20g. Extraction was performed three times with 100 ml of a saturated aqueous solution of sodium hydrogen carbonate. Further, the obtained ether layer was extracted three times with 100 ml of a 5% aqueous sodium hydroxide solution. After the obtained ether layer was dried over anhydrous magnesium sulfate, diethyl ether was distilled off under reduced pressure using a rotary evaporator to obtain 18.3 g of modified valerian oil (yield: 91.5%).

Test Example 1 Component Analysis The valerian oil before and after the alkali treatment of Example 1 was subjected to component analysis by GLC and GC-MS. As shown in Table 1, the valerian oil before the treatment was subjected to the alkali treatment as shown in Table 1 above. Fatty acids such as acetic acid (peak No. 7) and isovaleric acid (11) in the oil were completely removed.
The measurement conditions of GLC and GC-MS are as follows. <GLC measurement conditions>Model; Hewlett-Packard 5890 column; HP-INNOWax (60m x 0.25mm) Column temperature; 60 → 240 ° C (5 ° C / min temperature rise) Carrier gas; He (1.0ml / min) detector; FID <GC-MS measurement conditions>Model; Hewlett-Packard G1800A column; HP-INNOWax (60m × 0.25mm) Column temperature; 60 → 230 ° C (5 ° C / min temperature rise) Carrier gas; He (1.0ml / min)

Test Example 2 Aroma sensory test The aroma of the modified valerian oil produced in Example 1 and the valerian oil (before treatment) used as a raw material were evaluated by 10 specialized panels. The evaluation criteria are as follows. <Evaluation Criteria> A: 9 or more out of 10 evaluated that there was no unpleasant odor. …: 6 to 8 out of 10 persons evaluated that there was no unpleasant odor. Δ: 3 to 5 out of 10 persons evaluated that there was no unpleasant odor. X: Three or less out of ten evaluated that there was no unpleasant odor.

[0017]

[Table 2] ──────────────────────────────────── Valerian oil sensory evaluation ──────改 質 Modified valerian oil ◎ (Vine-like and fresh fruity woody notes) (Example 1 ) ──────────────────────────────────── Valerian oil × (with unpleasant odor) (Before treatment) ─ ───────────────────────────────────

As is apparent from Table 2 above, the valerian oil before treatment had an unpleasant odor, whereas the odor of the modified valerian oil from which acidic components such as fatty acids were removed by alkali treatment was unpleasant. It had no odor, had a pine-like, transparent and fresh fruity woody type scent, and was a very preferable scent compared to valerian oil before treatment. From this, it is inferred that the unpleasant odor of the conventional valerian oil was partly due to the acid odor of the fatty acid contained in the valerian oil.

Test Example 3 Pentobarbital sleep time extension
The sedative effect of inhalation of valerian oil before and after long-acting alkali treatment was evaluated by barbital sleep prolongation using mice. That is, an ICR male mouse (6 to 7 weeks old, body weight 30 to 35 g) was air-flowed with the modified valerian oil of Example 1 or valerian oil before treatment (triethyl citrate solution containing 5% of each oil). 20ml
In a 50 ml glass vial and dry air at 0.2
Pentobarbital sleep time (55 mg / kg intraperitoneally) was inhaled for 4 hours between the group inhaled by bubbling at a flow rate of ~ 0.3 ml / min and bubbling) and the group not inhaled (control). Measured and compared the difference. In addition, the test was performed with 6 animals in each group.

[0020]

[Table 3] 変 化 Test group Average sleep time change (%) * ──────────────────────────────────── Valerian oil (before treatment) inhalation group 167 ────吸入 Modified valerian oil (Example 1) inhalation group 178 ────── ────────────────────────────── * Value when the average sleep time of the control (non-inhaled group) is 100%. A value of 100 or more indicates that the sleeping time has been extended.

As is clear from Table 3, the alkali-treated valerian oil has a sleeping time prolonging effect at least equal to that of the untreated valerian oil, and the sedative effect of the valerian oil is not impaired by the alkali treatment. It has been shown.

[0022]

According to the present invention, valerian oil is treated with alkali to remove acidic components including fatty acids, thereby greatly improving the fragrance and having a sedative effect equal to or higher than that of conventional valerian oil. Modified valerian oil can be obtained easily and at low cost.

Claims (3)

[Claims] 1. A modified valerian oil obtained by removing a fatty acid from a valerian oil containing a fatty acid by alkali treatment. 2. A method for producing a modified valerian oil, which comprises treating a valerian oil containing a fatty acid with an alkali to remove the fatty acid. 3. The method according to claim 2, wherein an ether solution of valerian oil containing fatty acid is sequentially extracted with an aqueous solution of sodium hydrogen carbonate and an aqueous solution of sodium hydroxide to remove the fatty acid and remove the ether from the ether layer. A method for producing a modified valerian oil, comprising: