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JP4657653B2 - Body temperature raising agent - Google Patents

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JP4657653B2
JP4657653B2 JP2004243130A JP2004243130A JP4657653B2 JP 4657653 B2 JP4657653 B2 JP 4657653B2 JP 2004243130 A JP2004243130 A JP 2004243130A JP 2004243130 A JP2004243130 A JP 2004243130A JP 4657653 B2 JP4657653 B2 JP 4657653B2
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body temperature
angelate
agent
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drinking
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JP2006056858A (en
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美穂子 比留間
久美 笹野
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Soda Aromatic Co Ltd
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Description

本発明は、体温上昇剤に関する。さらには体内末梢部位体温低下改善剤に関するものである。   The present invention relates to a body temperature raising agent. Further, the present invention relates to an agent for improving body temperature lowering in the peripheral region of the body.

従来、有機酸類を飲料に添加する方法(特許文献1)や、スクシニルCoAよりも川下の代謝中間体(特許文献2)を飲料に添加する方法、辛味香辛料成分を飲料に添加する方法(特許文献3)などの方法によって、代謝を活発化し体温を上昇させる方法が提案されている。
一方、自律神経の調整力低下、低血圧、貧血などにより、いわゆる冷え性とよばれる末梢部位の体温低下を伴う各種症状が知られている。特に近年では、自律神経による調整機能に関しては、ストレスや、夏期の冷房による調整機能の低下が懸念されており、前記症状に陥る可能性が高まっている。
しかしながら、前記の体温を上昇させる方法は、エネルギー代謝を活発化させることにより体温を上昇させる効果はあるものの、末梢部位の体温低下改善については、充分な効果が得られるとは限らない。
特開2003−210137号公報 特開2003−012512号公報 特開2000−189121号公報
Conventionally, a method of adding organic acids to a beverage (Patent Document 1), a method of adding a metabolic intermediate downstream from succinyl CoA (Patent Document 2), a method of adding a spicy spice component to a beverage (Patent Document) There has been proposed a method for activating metabolism and increasing body temperature by the method 3).
On the other hand, various symptoms accompanied by a decrease in body temperature in a peripheral region called so-called coldness are known due to a reduction in autonomic nerve adjustment, hypotension, anemia, and the like. Particularly in recent years, with regard to the adjustment function by the autonomic nerve, there is concern about stress and the decrease of the adjustment function due to cooling in the summer, and the possibility of falling into the above-mentioned symptoms is increasing.
However, although the above-described method for increasing body temperature has the effect of increasing body temperature by activating energy metabolism, a sufficient effect is not always obtained for improving body temperature reduction at peripheral sites.
JP 2003-210137 A JP 2003-012512 A JP 2000-189121 A

本発明は、低温環境下で身体を温め、特に末梢部位での体温低下を改善することができる体温上昇剤および末梢部位体温低下改善剤、ならびにそれらを有効成分として含有する飲食品を提供することを目的とする。   The present invention provides a body temperature increasing agent and a peripheral region body temperature decrease improving agent capable of warming the body in a low temperature environment, particularly improving a decrease in body temperature in a peripheral region, and a food and drink containing them as an active ingredient. With the goal.

本発明は、デカン酸、5−デセン酸、6−デセン酸および下記式   The present invention relates to decanoic acid, 5-decenoic acid, 6-decenoic acid and

Figure 0004657653

(式中R1は水素原子、水酸基および/または炭素数1〜3のアルキル基が結合してもよいフェニル基またはメチルフェニル基またはエチルフェニル基、水酸基で置換されてもよい炭素数1〜10の直鎖または分岐鎖もしくは環を形成してもよい飽和または不飽和の炭素鎖を示す)で表されるアンゲリカ酸およびそのエステルから選ばれる少なくとも1つの化合物を有効成分として含有する体温上昇剤であり、さらには前記化合物群から選ばれる少なくとも1つの化合物を有効成分として含有する末梢部位体温低下改善剤である。
また、本発明の他の態様としては、前記体温上昇剤または末梢部位体温低下改善剤を有効成分として含有する飲食品である。
Figure 0004657653

(In the formula, R1 represents a hydrogen atom, a hydroxyl group and / or a phenyl group, a methylphenyl group, an ethylphenyl group or a hydroxyl group which may be substituted by a hydroxyl group and / or a hydroxyl group having 1 to 3 carbon atoms. A body temperature-elevating agent containing, as an active ingredient, at least one compound selected from angelic acid represented by a straight chain, a branched chain or a saturated or unsaturated carbon chain that may form a ring) Furthermore, it is a peripheral part body temperature decrease improving agent containing at least one compound selected from the above compound group as an active ingredient.
Moreover, as another aspect of this invention, it is the food / beverage products which contain the said body temperature increasing agent or a peripheral part body temperature fall improvement agent as an active ingredient.

本発明の体温上昇剤または末梢部位体温低下改善剤は、体温を上昇させ、冬季の低温下の環境において身体を温めることができる。また、手先足先などの末梢部位において、効果的に体温上昇効果が得られるため、いわゆる冷え性や冷房による冷えを改善することができる。   The body temperature elevating agent or peripheral region body temperature lowering improving agent of the present invention increases body temperature and can warm the body in a low temperature environment in winter. Moreover, since a body temperature increasing effect can be effectively obtained at peripheral sites such as the hands and feet, so-called cooling properties and cooling due to cooling can be improved.

本発明のデカン酸、5−デセン酸および6−デセン酸は、一般に香料として市販されており容易に入手することができる。また、いずれも公知の方法で製造することができる。たとえば、5(または6)−デセン酸は、特開昭59−116247号公報、特開昭58−059908号公報に記載の方法などにより製造することができる。
本発明の下記式2
The decanoic acid, 5-decenoic acid and 6-decenoic acid of the present invention are generally commercially available as perfumes and can be easily obtained. Moreover, all can be manufactured by a well-known method. For example, 5 (or 6) -decenoic acid can be produced by the method described in JP-A-59-116247 and JP-A-58-059908.
The following formula 2 of the present invention

Figure 0004657653

(式中R1は水素原子、水酸基および/または炭素数1〜3のアルキル基が結合してもよいフェニル基またはメチルフェニル基またはエチルフェニル基、水酸基で置換されてもよい炭素数1〜10の直鎖または分岐鎖もしくは環を形成してもよい飽和または不飽和の炭素鎖を示す)で表されるアンゲリカ酸およびそのエステル類として具体的には例えば、アンゲリカ酸、2−メチル−2−ブテニルアンゲレート、3−ヘキセニルアンゲレート、2−ヒドロキシ−2−メチル−3−ブテニルアンゲレート、2−メチル−2−プロぺニルアンゲレート、2−メチルブチルアンゲレート、3−ヒドロキシ−2−メチリデンブチルアンゲレート、3−メチルペンチルアンゲレート、ベンジルアンゲレート、ブチルアンゲレート、エチルアンゲレート、ゲラニルアンゲレート、ヘプチルアンゲレート、ヘキシルアンゲレート、イソブチルアンゲレート、イソペンチルアンゲレート、イソプロピルアンゲレート、ノニルアンゲレート、オクチルアンゲレート、ペンチルアンゲレート、フェネチルアンゲレート、プロピルアンゲレート、セカンダリブチルアンゲレート、ターシャリブチルアンゲレートが挙げられる。これらの化合物は、一般に市販されているものを使用することができる。また、特開昭57−112348号公報に記載された方法で製造することができる。また、これらの化合物はローマンカモミール(Anthemis nobilis L.)の精油に含まれていることが知られており、この精油を用いることもできる。
Figure 0004657653

(In the formula, R1 represents a hydrogen atom, a hydroxyl group and / or a phenyl group, a methylphenyl group, an ethylphenyl group or a hydroxyl group which may be substituted by a hydroxyl group and / or a hydroxyl group having 1 to 3 carbon atoms. Specific examples of the angelic acid and esters thereof represented by a straight chain, a branched chain or a saturated or unsaturated carbon chain that may form a ring include angelic acid, 2-methyl-2-but Tenenyl angelate, 3-hexenyl angelate, 2-hydroxy-2-methyl-3-butenyl angelate, 2-methyl-2-propenyl angelate, 2-methylbutyl angelate, 3-hydroxy- 2-methylidenebutyl angelate, 3-methylpentyl angelate, benzyl angelate, butyl angelate, ethyl angelate, Ranyl angelate, heptyl angelate, hexyl angelate, isobutyl angelate, isopentyl angelate, isopropyl angelate, nonyl angelate, octyl angelate, pentyl angelate, phenethyl angelate , Propyl angelate, secondary butyl angelate, and tertiary butyl angelate. As these compounds, commercially available compounds can be used. Moreover, it can manufacture by the method described in Unexamined-Japanese-Patent No. 57-112348. Further, these compounds are known to be contained in the essential oil of Roman chamomile (Anthemis nobilis L.), and this essential oil can also be used.

本発明の体温上昇剤または末梢部位体温低下改善剤は、前記化合物群をそれぞれ単独で用いてもよく、配合して用いてもよい。   The body temperature raising agent or the peripheral region body temperature lowering improving agent of the present invention may be used alone or in combination.

本発明の体温上昇剤または末梢部位体温低下改善剤は、用途に応じて、エタノール、水、プロピレングリコール、グリセリン、食用油脂またはそれらの混合溶液などの溶剤、医薬や食品に適用可能な塩類、糖、糖アルコール、賦形剤、可溶化剤、乳化剤、分散剤、安定化剤、抗酸化剤、色素、香料などを適宜配合することができる。   The body temperature elevating agent or peripheral region body temperature lowering improving agent of the present invention is a solvent such as ethanol, water, propylene glycol, glycerin, edible oil or fat, or a mixed solution thereof, salts applicable to pharmaceuticals and foods, sugar , Sugar alcohols, excipients, solubilizers, emulsifiers, dispersants, stabilizers, antioxidants, pigments, fragrances and the like can be appropriately blended.

本発明の体温上昇剤または末梢部位体温低下改善剤において、前記の化合物群の含有量は特に限定されないが、0.0001〜100質量%であることが好ましい。   In the body temperature increasing agent or the peripheral region body temperature lowering improving agent of the present invention, the content of the compound group is not particularly limited, but is preferably 0.0001 to 100% by mass.

本発明の体温上昇剤または末梢部位体温低下改善剤の形態は、特に限定されない。例えば、液状のままでもよく、公知の方法によって乳化、分散、粉末化するなど、用途に応じて適宜選択することができる。   The form of the body temperature increasing agent or the peripheral region body temperature lowering improving agent of the present invention is not particularly limited. For example, it may remain in a liquid state, and can be appropriately selected depending on the application, such as emulsification, dispersion, and powderization by a known method.

本発明の体温上昇剤または末梢部位体温低下改善剤は、ビタミン、ミネラル、アミノ酸、などの栄養強化剤、抗酸化剤、抗菌剤、その他の薬剤などと配合して使用することができる。また、本発明の体温上昇剤は、他の体温上昇剤と併用してもよい。   The body temperature elevating agent or peripheral region body temperature lowering improving agent of the present invention can be used in combination with nutrition enhancing agents such as vitamins, minerals and amino acids, antioxidants, antibacterial agents and other agents. Moreover, you may use the body temperature increasing agent of this invention together with another body temperature increasing agent.

本発明の体温上昇剤または末梢部位体温低下改善剤を、医薬品もしくは医薬部外品として製剤化する場合は、必要に応じて安定化剤、着色剤、嬌味剤、香料、賦形剤、溶剤、界面活性剤、乳化剤、保存剤、溶解補助剤、等張化剤、緩衝剤、結合剤、被覆剤、潤沢剤、崩壊剤などを加え、液剤、粉剤、散剤、顆粒剤、錠剤、糖衣剤、カプセル剤、懸濁剤、座剤など任意の剤形を選択することができる。   When formulating the body temperature increasing agent or peripheral region body temperature lowering improving agent of the present invention as a pharmaceutical product or a quasi-drug, a stabilizer, a coloring agent, a flavoring agent, a fragrance, an excipient, a solvent, if necessary. , Surfactants, emulsifiers, preservatives, solubilizers, tonicity agents, buffers, binders, coating agents, lubricants, disintegrants, etc., liquids, powders, powders, granules, tablets, dragees Any dosage form such as capsules, suspensions, suppositories and the like can be selected.

本発明の体温上昇剤または末梢部位体温低下改善剤は、香料として使用されている化合物であるため、飲食品に添加することができる。例えば、乳飲料、清涼飲料、嗜好飲料、アルコール飲料などの飲料、チョコレート、キャンディ、錠菓、ガム、スナック菓子、クッキー、ケーキ、その他焼き菓子などの菓子類、即席麺類、レトルト食品、冷凍食品などの調理食品、調味料、栄養補助食品などの食品類に添加することで、身体を効果的に温めることができる。また、これら食品を摂取することにより冷えを改善するなど、飲食品に健康維持の機能を付加することができる。   Since the body temperature elevating agent or the peripheral body temperature lowering improving agent of the present invention is a compound used as a fragrance, it can be added to food and drink. For example, beverages such as milk beverages, soft drinks, taste beverages, alcoholic beverages, chocolate, candy, tablet confectionery, gum, snack confectionery, cookies, cakes, other baked confectionery, instant noodles, retort food, frozen food, etc. By adding to cooked foods, seasonings, dietary supplements and other foods, the body can be effectively warmed. Moreover, the function of maintaining health can be added to food and drink, such as improving coldness by ingesting these foods.

本発明の体温上昇剤または末梢部位体温低下改善剤を飲食品に添加する場合、特に添加量の制限はないが、0.0001〜5質量%であることが好ましい。   When the body temperature elevating agent or the peripheral region body temperature lowering improving agent of the present invention is added to a food or drink, the amount of addition is not particularly limited, but it is preferably 0.0001 to 5% by mass.

本発明の体温上昇剤または末梢部位体温低下改善剤を飲食品に添加する方法は、特に制限はないが必要に応じて、乳化剤、分散剤、安定化剤などを加えることもできる。   The method for adding the body temperature elevating agent or the peripheral region body temperature lowering improving agent of the present invention to a food or drink is not particularly limited, but an emulsifier, a dispersant, a stabilizer and the like can be added as necessary.

本発明の体温上昇剤または末梢部位体温低下改善剤を飲食品に添加する場合は、ビタミン、ミネラル、アミノ酸などの栄養強化剤、抗酸化剤、抗菌剤、食物繊維、血流促進剤、抗血栓剤、抗アレルギー剤など他の機能性成分を本発明の体温上昇剤の機能を阻害しない範囲で併用することもできる。   When adding the body temperature increasing agent or peripheral region body temperature lowering improving agent of the present invention to foods and drinks, nutritional enhancing agents such as vitamins, minerals, amino acids, antioxidants, antibacterial agents, dietary fiber, blood flow promoters, antithrombotic agents Other functional components such as an agent and an antiallergic agent can be used in combination as long as the function of the body temperature increasing agent of the present invention is not inhibited.

本発明の内容は以下の実験例および実施例として説明するが、これらに限定されるものでない。
(試験例1)
各被検物質を70容量%の含水エタノールに溶解させ1%溶液を作成し、これを蒸留水に添加して、被検物質を0.001質量%含有する試料を調整した。また、対照としては70容量%の含水エタノールを0.1%添加した蒸留水を用いた。
被検物質1・・・5−デセン酸、6−デセン酸混合物
被検物質2・・・イソブチルアンゲレート
被検物質3・・・3−メチルペンチルアンゲレート
被検物質4・・・ローマンカモミールオイル
The contents of the present invention will be described as the following experimental examples and examples, but are not limited thereto.
(Test Example 1)
Each test substance was dissolved in 70% by volume of water-containing ethanol to prepare a 1% solution, which was added to distilled water to prepare a sample containing 0.001% by mass of the test substance. As a control, distilled water to which 0.1% of 70% by volume of water-containing ethanol was added was used.
Test substance 1 ... 5-decenoic acid, 6-decenoic acid mixture Test substance 2 ... Isobutyl angelate Test substance 3 ... 3-methylpentyl angelate Test substance 4 ... Roman Chamomile oil

室温25℃の環境下で、試料または対照を100ml飲用することにより試験を行った。測定装置として、NEC三栄株式会社製のサーモトレーサー(TH5104)を使用し、図1に示す左右の手の平および指の定点温度を測定した。   The test was performed by drinking 100 ml of the sample or control in an environment at room temperature of 25 ° C. As a measuring device, a thermotracer (TH5104) manufactured by NEC Sanei Co., Ltd. was used, and the left and right palms and fixed point temperatures of fingers shown in FIG. 1 were measured.

(図1)

Figure 0004657653
(Figure 1)
Figure 0004657653

各定点における温度は、飲用前の温度測定値を基準点として、試料または対照を飲用した後、3分おきに30分までの温度を測定して、基準点との温度差を求めた。   The temperature at each fixed point was determined by measuring the temperature up to 30 minutes every 3 minutes after drinking the sample or the control with the temperature measured before drinking as the reference point, and obtaining the temperature difference from the reference point.

(試験結果)
定点温度の測定により得られた変動値より、飲用後、10分から30分の間における最大値を試料と対照とで比較し、試料飲用時の数値から対照飲用時の数値を差し引いた数値を比較値とした。
(Test results)
From the fluctuation value obtained by measuring the fixed-point temperature, compare the maximum value between 10 and 30 minutes after drinking between the sample and the control, and subtract the numerical value when drinking the sample from the value when drinking the sample. Value.

5−デセン酸および、6−デセン酸混合物の飲用効果試験の結果を表1に示す。   Table 1 shows the results of a drinking effect test of 5-decenoic acid and a 6-decenoic acid mixture.

Figure 0004657653
Figure 0004657653

表1の結果から、試料飲用時は対照と比較して有意に温度上昇がみられ、5−デセン酸および、6−デセン酸混合物は経口摂取によって末梢部位において体温を上昇させる効果があることが確認できた。   From the results shown in Table 1, when the sample was drunk, the temperature was significantly increased compared to the control, and 5-decenoic acid and the 6-decenoic acid mixture had the effect of increasing body temperature at the peripheral site by oral ingestion. It could be confirmed.

次に、イソブチルアンゲレートの飲用効果試験の結果を表2に示す。   Next, Table 2 shows the results of the drinking effect test of isobutyl angelate.

Figure 0004657653
Figure 0004657653

表2の結果から、試料飲用時は対照と比較して有意に温度上昇がみられ、イソブチルアンゲレートは経口摂取によって末梢部位において体温を上昇させる効果があることが確認できた。   From the results in Table 2, it was confirmed that when the sample was taken, the temperature increased significantly compared to the control, and isobutyl angelate had the effect of increasing the body temperature at the peripheral site by ingestion.

次に、3−メチルペンチルアンゲレートの飲用効果試験の結果を表3に示す。   Next, Table 3 shows the results of the drinking effect test of 3-methylpentyl angelate.

Figure 0004657653
Figure 0004657653

表3の結果から、試料飲用時は対照と比較して有意に温度上昇がみられ、3−メチルペンチルアンゲレートは経口摂取によって末梢部位において体温を上昇させる効果があることが確認できた。   From the results in Table 3, it was confirmed that when the sample was drunk, the temperature was significantly increased as compared with the control, and 3-methylpentylangelate had an effect of increasing body temperature at the peripheral site by ingestion.

次に、ローマンカモミールオイルの飲用効果試験の結果を表4に示す。   Next, Table 4 shows the results of a drinking effect test of roman chamomile oil.

Figure 0004657653
Figure 0004657653

表4の結果から、試料飲用時は対照と比較して有意に温度上昇がみられ、ローマンカモミールオイルは経口摂取によって末梢部位において体温を上昇させる効果があることが確認できた。   From the results in Table 4, it was confirmed that the temperature was significantly increased when the sample was drunk compared with the control, and that roman chamomile oil had an effect of increasing body temperature at the peripheral site by oral ingestion.

(試験方法)
実施例1の試験における試料を、以下に示す処方の飲料に替えて飲用試験を行った。本発明の体温上昇剤としては、ローマンカモミールオイルとイソブチルアンゲレートを併用した。また、対照には、本発明の前記の体温上昇剤を含まず、他の成分は同一の飲料を調整した。
(Test method)
A drinking test was conducted by replacing the sample in the test of Example 1 with a beverage having the following formulation. As the body temperature increasing agent of the present invention, roman chamomile oil and isobutyl angelate were used in combination. Moreover, the control did not contain the above-mentioned body temperature increasing agent of the present invention, and other ingredients prepared the same beverage.

飲料処方例
――――――――――――――――――――――
果糖ぶどう糖液糖 60.0
アップル透明果汁 4.3
クエン酸 2.3
クエン酸三ナトリウム 0.8
アスコルビン酸 0.2
スクラロース 0.03
アセスルファムカリウム 0.02
香料 0.99
ローマンカモミールオイル 0.009
イソブチルアンゲレート 0.001
水 残量
――――――――――――――――――――――
1000.0g
Beverage formulation example ――――――――――――――――――――――
Fructose glucose liquid sugar 60.0
Apple transparent fruit juice 4.3
Citric acid 2.3
Trisodium citrate 0.8
Ascorbic acid 0.2
Sucralose 0.03
Acesulfame potassium 0.02
Perfume 0.99
Roman chamomile oil 0.009
Isobutyl angelate 0.001
Water balance ――――――――――――――――――――――
1000.0g

(試験結果)
実施例1と同様に、定点温度の測定により得られた変動値より、飲用後、10分から30分の間における最大値を試料と対照とで比較し、試料飲用時の数値から対照飲用時の数値を差し引いた数値を比較値とした。
(Test results)
As in Example 1, the maximum value between 10 and 30 minutes after drinking is compared between the sample and the control from the fluctuation value obtained by measuring the fixed point temperature, and the value at the time of drinking the sample is compared with the value at the time of drinking the sample. A value obtained by subtracting the value was used as a comparison value.

処方例のニアウォーターについての飲用試験結果を表5に示す。   Table 5 shows the drinking test results for the prescription example near water.

Figure 0004657653
Figure 0004657653

表5の結果から、試料飲用時は対照と比較して有意に温度上昇がみられ、ローマンカモミールオイルとイソブチルアンゲレートを添加した飲料を経口摂取することによって、末梢部位における体温上昇効果が得られることが確認できた。   From the results in Table 5, when the sample was drunk, the temperature increased significantly compared to the control, and by ingesting a drink added with roman chamomile oil and isobutyl angelate, an effect of increasing body temperature at the peripheral site was obtained. It was confirmed that

本発明の体温上昇剤または末梢部位体温低下改善剤の有効成分として使用される化合物は、香料として使用実績がある化合物であり、刺激性などは極めて小さく、飲食品に幅広く添加することができる。また、本発明の化合物群は容易に合成ができるため、大量生産が可能である。   The compound used as an active ingredient of the body temperature increasing agent or peripheral region body temperature lowering improving agent of the present invention is a compound that has been used as a fragrance and has extremely little irritation and can be widely added to foods and drinks. In addition, since the compound group of the present invention can be easily synthesized, mass production is possible.

Claims (2)

5−デセン酸および6−デセン酸から選ばれる少なくとも1つの化合物を有効成分として含有する体温上昇剤。 A body temperature increasing agent containing, as an active ingredient, at least one compound selected from 5-decenoic acid and 6-decenoic acid. 5−デセン酸および6−デセン酸から選ばれる少なくとも1つの化合物を有効成分として含有する末梢部位体温低下改善剤。 A peripheral region body temperature lowering improving agent comprising as an active ingredient at least one compound selected from 5-decenoic acid and 6-decenoic acid.
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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5859908A (en) * 1981-10-06 1983-04-09 Soda Koryo Kk Perfumery composition containing unsaturated fatty acid
JPS5896014A (en) * 1981-12-02 1983-06-07 Soda Koryo Kk Flavor composition containing unsaturated fatty acid
JPH0374351A (en) * 1989-08-15 1991-03-28 Yamamoto Koryo Kk Production of angelic acid ester and derivative thereof
JP2001163719A (en) * 1999-12-07 2001-06-19 Soda Aromatic Co Ltd Tyrosinase activity inhibitor
WO2002100989A1 (en) * 2001-06-08 2002-12-19 Soda Aromatic Co.,Ltd Perfume composition and process for producing the same
JP2003119491A (en) * 2001-08-08 2003-04-23 Shiseido Co Ltd Perfume composition for psychological exhilaranttion
WO2003074043A1 (en) * 2002-03-04 2003-09-12 The Nisshin Oillio Group Ltd. Body temperature elevating agents
JP2003535894A (en) * 2000-06-20 2003-12-02 エヌ・ブイ・ニュートリション・サイエンシス Medium-chain fatty acids applicable as antibacterial agents

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5859908A (en) * 1981-10-06 1983-04-09 Soda Koryo Kk Perfumery composition containing unsaturated fatty acid
JPS5896014A (en) * 1981-12-02 1983-06-07 Soda Koryo Kk Flavor composition containing unsaturated fatty acid
JPH0374351A (en) * 1989-08-15 1991-03-28 Yamamoto Koryo Kk Production of angelic acid ester and derivative thereof
JP2001163719A (en) * 1999-12-07 2001-06-19 Soda Aromatic Co Ltd Tyrosinase activity inhibitor
JP2003535894A (en) * 2000-06-20 2003-12-02 エヌ・ブイ・ニュートリション・サイエンシス Medium-chain fatty acids applicable as antibacterial agents
WO2002100989A1 (en) * 2001-06-08 2002-12-19 Soda Aromatic Co.,Ltd Perfume composition and process for producing the same
JP2003119491A (en) * 2001-08-08 2003-04-23 Shiseido Co Ltd Perfume composition for psychological exhilaranttion
WO2003074043A1 (en) * 2002-03-04 2003-09-12 The Nisshin Oillio Group Ltd. Body temperature elevating agents

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