JPH0586086A - Capsaicinoid glycoside - Google Patents
Capsaicinoid glycosideInfo
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- JPH0586086A JPH0586086A JP6283892A JP6283892A JPH0586086A JP H0586086 A JPH0586086 A JP H0586086A JP 6283892 A JP6283892 A JP 6283892A JP 6283892 A JP6283892 A JP 6283892A JP H0586086 A JPH0586086 A JP H0586086A
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- Prior art keywords
- capsaicinoid
- compound
- formula
- glycoside
- sugar
- Prior art date
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Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明はカプサイシノイド配糖体
に関する。FIELD OF THE INVENTION The present invention relates to capsaicinoid glycosides.
【０００２】[0002]
【従来の技術】トウガラシの辛味成分であるカプサイシ
ノイドは唾液分泌亢進作用、エネルギー代謝亢進作用、
抗酸化作用、血小板凝集阻害作用など様々な作用を有す
る。しかしながらカプサイシノイドはその強い辛味のた
めに用途が限定されている。2. Description of the Related Art Capsaicinoid, which is a pungent component of red pepper, promotes salivation and energy metabolism,
It has various actions such as antioxidant action and platelet aggregation inhibitory action. However, capsaicinoids have limited applications due to their intense pungency.
【０００３】[0003]
【発明が解決しようとする課題】本発明はカプサイシノ
イドの上述した有用な作用を維持しつつその強い辛味が
消失した化合物を提供することを目的とするものであ
る。DISCLOSURE OF THE INVENTION It is an object of the present invention to provide a compound in which the strong pungency is lost while maintaining the above-mentioned useful action of capsaicinoid.
【０００４】[0004]
【課題を解決するための手段】本発明は式（Ｉ）The present invention provides a compound of formula (I)
【化２】 （式中Ｒ1は炭素原子数７〜１２を有するアルキル基ま
たはアルケニル基を示し、Ｒ2は所望により水酸基が保
護された糖残基を示す）で表わされるカプサイシノイド
配糖体よりなる。[Chemical 2] (Wherein R 1 represents an alkyl group or an alkenyl group having 7 to 12 carbon atoms, and R 2 represents a sugar residue in which a hydroxyl group is optionally protected), which is a capsaicinoid glycoside.
【０００５】配糖体には、糖の立体異性によりα−アノ
マーとβ−アノマーが存在するが、本発明のカプサイシ
ノイド配糖体はα−アノマーおよびβ−アノマー並びに
それらの混合物が包含される。Glycosides have α-anomers and β-anomers depending on the stereoisomerism of sugar, and the capsaicinoid glycosides of the present invention include α-anomers and β-anomers and mixtures thereof.
【０００６】上記式中、Ｒ1の代表的な例としては、７
−メチル−trans−５−オクタニル、７−メチルオクタ
ニル、６−メチルヘプタニル、８−メチルノナニル、８
−メチル−trans−５−ノネニル、７−メチルノナニ
ル、７−メチル−trans−６−ノネニル、ヘプタニル、
オクタニル、デカニル、ウンデカニル、５−メチルヘプ
タニル、ドデカニルなどがあげられるがこれらに限られ
ない。In the above formula, a typical example of R 1 is 7
-Methyl-trans-5-octanyl, 7-methyloctanyl, 6-methylheptanyl, 8-methylnonanyl, 8
-Methyl-trans-5-nonenyl, 7-methylnonanyl, 7-methyl-trans-6-nonenyl, heptanyl,
Examples thereof include, but are not limited to, octanyl, decanyl, undecanyl, 5-methylheptanyl, dodecanyl and the like.
【０００７】Ｒ2としては単糖類または二糖類の残基が
好ましい。R 2 is preferably a monosaccharide or disaccharide residue.
【０００８】単糖類の例としては、四炭糖（エリトロー
ス、トレオース）、五炭糖（リボース、アラビノース、
キシロース、リキソース、リブロース、キシルロー
ス）、六炭糖（アロース、ガラクトース、グルコース、
グロース、マンノース、タロース、フルクトース、プシ
コース、ソルボース、タガロース）等が挙げられる。Examples of monosaccharides are tetracarbon sugars (erythrose, threose), pentacarbon sugars (ribose, arabinose,
Xylose, lyxose, ribulose, xylulose), hexose (allose, galactose, glucose,
Gulose, mannose, talose, fructose, psicose, sorbose, tagarose) and the like.
【０００９】二糖類の例としては、トレハロース、サッ
カロース、マルトース、セロビオース、ゲンチオビノー
ス、ラクトース等が挙げられる。Examples of disaccharides include trehalose, saccharose, maltose, cellobiose, gentiovinose, lactose and the like.
【００１０】Ｒ2には、上記の糖の水酸基を当該技術分
野で慣用的に使用される保護基例えばアセチル、ベンゾ
イルのようなアシル基、テトラヒドロフラニル基、ベン
ジル基等で保護したものの残基も包含される。R 2 also includes a residue of the above-mentioned sugar hydroxyl group protected by a protecting group conventionally used in the art, for example, an acyl group such as acetyl and benzoyl, a tetrahydrofuranyl group, a benzyl group and the like. Included.
【００１１】本発明の化合物（Ｉ）は、カプサイシノイ
ドの強い辛味は消失しているが、他の有用な薬理作用、
即ち、エネルギー代謝亢進作用、抗酸化作用、血小板凝
集作用などは維持している。従って化合物(Ｉ)は上記薬
理効果を目的とした医薬品としてあるいは食品添加物と
して使用されうる。特に糖部分が単糖類や二糖類などの
場合には、化合物（Ｉ）の水溶性が向上するので飲料へ
の添加が容易になる。The compound (I) of the present invention eliminates the strong pungency of capsaicinoid, but has other useful pharmacological actions,
That is, the energy metabolism promoting action, antioxidant action, platelet aggregation action and the like are maintained. Therefore, the compound (I) can be used as a drug for the above-mentioned pharmacological effects or as a food additive. In particular, when the sugar moiety is a monosaccharide or a disaccharide, the water solubility of the compound (I) is improved, so that it can be easily added to a beverage.
【００１２】本発明の化合物（Ｉ）は、一般にグリコシ
ド合成法として知られている反応に従って式（II）The compound (I) of the present invention has the formula (II) according to the reaction generally known as a glycoside synthesis method.
【化３】 （式中Ｒ1は前述したものと同一意義を有する）を有す
るカプサイシノイドをハロゲン化グリコシル誘導体等の
糖供与体と反応させることによって製造される。[Chemical 3] It is prepared by reacting a capsaicinoid having the formula (wherein R 1 has the same meaning as described above) with a sugar donor such as a halogenated glycosyl derivative.
【００１３】すなわち、銀塩あるいは水銀塩存在下、ハ
ロゲン化グリコシル誘導体とアルコール類を反応させる
Konigs-Knorr法、アルドースを塩化水素、硫酸、カチオ
ン交換樹脂などの酸触媒を含む低級アルコール中で加熱
するFischerの方法、ハロゲン化グリコシル誘導体を塩
基存在下フェノール類と反応させる方法、１−Ｏ−アセ
チル化グリコシル誘導体をパラトルエンスルホン酸、塩
化亜鉛、塩化鉄、塩化スズ（IV）、オキシ塩化リン、硫
酸、陽イオン交換樹脂などの酸触媒存在下フェノール類
と加熱溶融してフェニルグリコシドを得るHelferich法
などが適用できる。That is, a halogenated glycosyl derivative is reacted with an alcohol in the presence of a silver salt or a mercury salt.
Konigs-Knorr method, Fischer method of heating aldose in lower alcohol containing acid catalyst such as hydrogen chloride, sulfuric acid, cation exchange resin, method of reacting halogenated glycosyl derivative with phenols in the presence of base, 1-O- Helferich for obtaining phenylglycosides by heating and melting acetylated glycosyl derivatives with phenols in the presence of acid catalysts such as paratoluenesulfonic acid, zinc chloride, iron chloride, tin (IV) chloride, phosphorus oxychloride, sulfuric acid, and cation exchange resins Laws can be applied.
【００１４】例えば、Helferich法により製造する場合
は、カプサイシノイド（II）とアセチル化糖を塩化スズ
（IV）存在下において、１,２−ジクロロエタン、ジク
ロロメタン、ベンゼン、キシレンなどの適当な溶媒中、
好ましくは１,２−ジクロロエタン、ジクロロメタンで
３〜８時間撹拌することによりアセチル化糖の配糖体が
得られる。また、それを脱アセチルすることにより配糖
体が容易に合成できる。For example, in the case of production by the Helferich method, capsaicinoid (II) and acetylated sugar are added in the presence of tin (IV) chloride in a suitable solvent such as 1,2-dichloroethane, dichloromethane, benzene or xylene.
Preferably, the glycoside of acetylated sugar is obtained by stirring with 1,2-dichloroethane and dichloromethane for 3 to 8 hours. In addition, a glycoside can be easily synthesized by deacetylating it.
【００１５】[0015]
【実施例】次に実施例を示して本発明を更に具体的に説
明する。EXAMPLES Next, the present invention will be described more specifically by showing examples.
【００１６】実施例１ Ｎ−〔４−（２,３,４,６−テトラ−Ｏ−アセチル−β
−Ｄ−グルコピラノシルオキシ）−３−メトキシベンジ
ル〕ノナンアミド（Ｉａ） Ｎ−バニリルノナンアミド１.４７ｇ、ペンタアセチル
−β−Ｄ−グルコース１.９５ｇを、１,２−ジクロロエ
タン１５mlに溶かし、塩化スズ(IV）０.８６mlを加え、
室温で３.５時間撹拌する。水洗後、溶媒を留去し、得
られた油状物質を分取用シリカゲル薄層クロマトグラフ
ィーで精製し、Ｉａを４８０mg得た（収率１５％）。Example 1 N- [4- (2,3,4,6-tetra-O-acetyl-β
-D-glucopyranosyloxy) -3-methoxybenzyl] nonanamide (Ia) 1.47 g of N-vanillyl nonanamide and 1.95 g of pentaacetyl-β-D-glucose were dissolved in 15 ml of 1,2-dichloroethane. , 0.86 ml of tin (IV) chloride was added,
Stir at room temperature for 3.5 hours. After washing with water, the solvent was distilled off, and the resulting oily substance was purified by preparative silica gel thin layer chromatography to obtain 480 mg of Ia (yield 15%).
【００１７】Ｉａ IR（ヌジョール）：2920、 2850、 1765、 1640、 1475、 13
80、 1230、 1220、 1095、 1050、1030、 915、840cm-1 1 H-NMR (400MHz、 CDCl3) δ:0.87 (3H, t、 J=6.8Hz)、
1.3 (10H, m)、 1.65 (2H, m)、 2.04 (6H, s)、 2.08(6H,
s)、 2.21 (2H, t, J=7.5Hz)、 3.75 (1H, m)、 3.80 (3
H, s)、 4.15 (1H, dd, J=12.3, 2.4Hz)、 4.27 (1H, dd,
J=12.3, 4.8Hz)、 4.38 (2H, d, J=5.7Hz)、 4.92 (1H,
dt, J=7.3, 3.6Hz)、 5.16 (1H, m)、 5.27 (2H, m)、 5.7
7 (1H, t, J=5.7Hz)、 6.76 (1H, dd, J=8.1, 1.7Hz)、
6.83 (1H, d, J=1.7Hz)、 7.06 (1H,d,J=8.1Hz)Ia IR (Nujol): 2920, 2850, 1765, 1640, 1475, 13
80, 1230, 1220, 1095, 1050,1030, 915,840cm -1 1 H-NMR (400MHz, CDCl 3) δ: 0.87 (3H, t, J = 6.8Hz),
1.3 (10H, m), 1.65 (2H, m), 2.04 (6H, s), 2.08 (6H, m)
s), 2.21 (2H, t, J = 7.5Hz), 3.75 (1H, m), 3.80 (3
H, s), 4.15 (1H, dd, J = 12.3, 2.4Hz), 4.27 (1H, dd,
J = 12.3, 4.8Hz), 4.38 (2H, d, J = 5.7Hz), 4.92 (1H,
dt, J = 7.3, 3.6Hz), 5.16 (1H, m), 5.27 (2H, m), 5.7
7 (1H, t, J = 5.7Hz), 6.76 (1H, dd, J = 8.1, 1.7Hz),
6.83 (1H, d, J = 1.7Hz), 7.06 (1H, d, J = 8.1Hz)
【００１８】[0018]
【化４】 [Chemical 4]
【００１９】実施例２ Ｎ−〔４−（β−Ｄ−グルコピラノシルオキシ）−３−
メトキシベンジル〕ノナンアミド（Ｉｂ） Ｉａ ６０mgをアセトン３mlに溶かし、１Ｎ−水酸化ナ
トリウム０.４mlを加え、室温で３０分間撹拌する。イ
オン交換樹脂（アンバーライトＩＲ−１２０）を加えイ
オン交換を行ったのち、溶媒を留去し、分取用シリカゲ
ル薄層クロマトグラフィーにより分離精製し、Ｉｂを９
mg得た（収率２０％）。Example 2 N- [4- (β-D-glucopyranosyloxy) -3-
Methoxybenzyl] nonanamide (Ib) Ia (60 mg) is dissolved in acetone (3 ml), 1N-sodium hydroxide (0.4 ml) is added, and the mixture is stirred at room temperature for 30 minutes. Ion exchange resin (Amberlite IR-120) was added for ion exchange, the solvent was distilled off, and the residue was separated and purified by preparative silica gel thin layer chromatography to give Ib of 9
mg was obtained (20% yield).
【００２０】Ｉｂ 元素分析 実測値： Ｃ ６０.７９ Ｈ ８.２８ Ｎ ２.
８４ 計算値： Ｃ ６０.６４ Ｈ ８.１９ Ｎ ３.
０７ mp １７９〜１８１℃ IR (KBr):3555、 3350、 3270、 2920、 2850、 1640、 1510、
1430、 1270、 1225、 1090、 1080、 1055、 1020cm-1 1 H-NMR (400MHz, CD3OD)δ:0.89 (3H, t, J=6.8Hz)、 1.
3 (10H, m)、 1.62 (2H, m)、 2.21 (2H, t, J=7.5Hz)、
3.3〜3.5 (4H, m)、 3.67 (1H, m)、 3.84 (3H, s)、 3.85
(1H, m)、 4.29 (2H, s)、 4.85 (1H, d, J=7.3Hz)、 4.9
(br, -NH, -OH)、 6.82 (1H, dd, J=8.3, 2.0Hz)、 6.94
(1H, d, J=2.0Hz)、 7.11(1H, d, J=8.3Hz) 比旋光度 〔α〕D 24 −４５.８°(c ０.６，ＣＨ3ＯＨ）Ib elemental analysis found: C 60.79 H 8.28 N 2.
84 Calculated: C 60.64 H 8.19 N 3.
07 mp 179-181 ° C IR (KBr): 3555, 3350, 3270, 2920, 2850, 1640, 1510,
1430, 1270, 1225, 1090, 1080, 1055, 1020cm -1 1 H-NMR (400MHz, CD 3 OD) δ: 0.89 (3H, t, J = 6.8Hz), 1.
3 (10H, m), 1.62 (2H, m), 2.21 (2H, t, J = 7.5Hz),
3.3 to 3.5 (4H, m), 3.67 (1H, m), 3.84 (3H, s), 3.85
(1H, m), 4.29 (2H, s), 4.85 (1H, d, J = 7.3Hz), 4.9
(br, -NH, -OH), 6.82 (1H, dd, J = 8.3, 2.0Hz), 6.94
(1H, d, J = 2.0Hz), 7.11 (1H, d, J = 8.3Hz) Specific optical rotation [α] D 24 -45.8 ° (c 0.6, CH 3 OH)
【００２１】[0021]
【化５】 [Chemical 5]
【００２２】実施例３ Ｎ−〔４−（２,３,４,６−テトラ−Ｏ−アセチル−α
−Ｄ−グルコピラノシルオキシ）−３−メトキシベンジ
ル〕ノナンアミド（Ｉｃ） Ｎ−バニリルノナンアミド０.２９ｇ、ペンタアセチル
−β−Ｄ−グルコース０.９８ｇを、ジクロロメタン２.
５mlに溶かし、塩化スズ（IV）０.２９mlを加え、８時
間加熱還流する。水洗後、溶媒を留去し、得られた油状
物質をシリカゲルカラムクロマトグラフィーに共したの
ち、逆相分取ＨＰＬＣによって精製しＩｃを２３６mg得
た（収率４１％）。Example 3 N- [4- (2,3,4,6-tetra-O-acetyl-α
-D-glucopyranosyloxy) -3-methoxybenzyl] nonanamide (Ic) N-vanillyl nonanamide 0.29 g, pentaacetyl-β-D-glucose 0.98 g, dichloromethane 2.
Dissolve in 5 ml, add tin (IV) chloride 0.29 ml, and heat to reflux for 8 hours. After washing with water, the solvent was evaporated, the obtained oily substance was subjected to silica gel column chromatography, and then purified by reverse phase preparative HPLC to obtain 236 mg of Ic (yield 41%).
【００２３】Ｉｃ IR (KBr):2925、 2850、 1745、 1640、 1515、 1365、 1220、
1040cm-1 1 H-NMR (400MHz, CDCl3)δ:0.88 (3H, t, J=7.0Hz)、 1.
3 (10H, m)、 1.65 (2H, m)、 2.05 (6H, s)、 2.06(3H,
s)、 2.11 (3H, s)、 2.21 (2H, t, J=7.7Hz)、 3.80 (3H,
s)、 4.09 (1H, dd, J=12.1, 2.2Hz)、 4.27 (1H, dd, J
=12.1, 4.7 Hz)、 4.38 (2H, d, J=5.7 Hz)、4.42 (1H, d
dd, J=10.3, 4.7, 2.2Hz)、 4.98 (1H, dd, J=10.2, 3.8
Hz)、 5.14(1H, dd, J=10.3, 9.7Hz)、 5.65 (1H, d, J=
3.8Hz)、 5.72 (1H, dd, J=10.2, 9.7Hz)、 5.75 (1H, t,
J=5.7Hz)、 6.77 (1H, dd, J=8.1, 2.0Hz)、 6.84 (1H,
d, J=2.0Hz)、 6.96 (1H, d, J=8.1Hz)13 C-NMR (100MHz, CDCl3)δ:14.0、 20.56、 20.60、 20.6
4、 22.6、 25.8、 29.1、 29.30、 29.33、 31.8、 36.7、43.
2、 55.9、 61.8、 68.2、 68.7、 70.0、 70.9、 96.4、 112.
6、 120.0、 120.4、 135.5、 144.6、 151.2、 169.5、 169.
8、 170.0、 170.3、 172.9Ic IR (KBr): 2925, 2850, 1745, 1640, 1515, 1365, 1220,
1040cm -1 1 H-NMR (400MHz, CDCl 3 ) δ: 0.88 (3H, t, J = 7.0Hz), 1.
3 (10H, m), 1.65 (2H, m), 2.05 (6H, s), 2.06 (3H, m)
s), 2.11 (3H, s), 2.21 (2H, t, J = 7.7Hz), 3.80 (3H, s)
s), 4.09 (1H, dd, J = 12.1, 2.2Hz), 4.27 (1H, dd, J
= 12.1, 4.7 Hz), 4.38 (2H, d, J = 5.7 Hz), 4.42 (1H, d
dd, J = 10.3, 4.7, 2.2Hz), 4.98 (1H, dd, J = 10.2, 3.8
Hz), 5.14 (1H, dd, J = 10.3, 9.7Hz), 5.65 (1H, d, J =
3.8Hz), 5.72 (1H, dd, J = 10.2, 9.7Hz), 5.75 (1H, t,
J = 5.7Hz), 6.77 (1H, dd, J = 8.1, 2.0Hz), 6.84 (1H,
d, J = 2.0Hz), 6.96 (1H, d, J = 8.1Hz) 13 C-NMR (100MHz, CDCl 3 ) δ: 14.0, 20.56, 20.60, 20.6
4, 22.6, 25.8, 29.1, 29.30, 29.33, 31.8, 36.7, 43.
2, 55.9, 61.8, 68.2, 68.7, 70.0, 70.9, 96.4, 112.
6, 120.0, 120.4, 135.5, 144.6, 151.2, 169.5, 169.
8, 170.0, 170.3, 172.9
【００２４】実施例４ Ｎ−〔４−（α−Ｄ−グルコピラノシルオキシ）−３−
メトキシベンジル〕ノナンアミド（Ｉｄ） Ｉｃ ６２mgをメタノール３mlに溶かし、ＩＮ−水酸化
ナトリウム１mlを加え、室温で１.５時間撹拌する。濃
塩酸を加え中和を行いメタノールを留去した後、水層に
酢酸エチル５mlを加え、分液する。酢酸エチル層を濃縮
後、逆相分取ＨＰＬＣにより精製し、Ｉｄ ２６mgを得
た（収率５７％）。Example 4 N- [4- (α-D-glucopyranosyloxy) -3-
62 mg of methoxybenzyl] nonanamide (Id) Ic was dissolved in 3 ml of methanol, 1 ml of IN-sodium hydroxide was added, and the mixture was stirred at room temperature for 1.5 hours. Concentrated hydrochloric acid is added for neutralization and methanol is distilled off. Then, 5 ml of ethyl acetate is added to the aqueous layer to separate the layers. The ethyl acetate layer was concentrated and purified by reverse phase preparative HPLC to give Id 26 mg (yield 57%).
【００２５】Ｉｄ mp １７４〜１７７℃ IR (KBr):3300、 2900、 2840、 1640、 1545、 1515、 1275、
1230、 1110、 1090、 1055、 1030、 1010cm-1 1 H-NMR (400MHz, CD3OD)δ:0.89 (3H, t, J=6.8Hz)、 1.
3 (10H, m)、 1.62 (2H, m)、 2.21 (2H, t, J=7.5Hz)、
3.42 (1H, dd, J=10.0, 9.0Hz)、 3.51(1H, dd, J=10.0,
3.7Hz)、 3.7 (2H,m)、 3.8 (1H, m)、 3.84 (3H, s)、 3.
86 (1H, t, J=10.0Hz)、 4.29 (2H, s)、 4.9 (br, -NH,
-OH)、 5.40 (1H, d, J=3.7 Hz)、 6.81 (1H, dd, J=8.2,
2.0Hz)、 6.94 (1H, d, J=2.0Hz)、 7.14 (1H, d,J=8.2H
z)13 C-NMR (100MHz, CD3OD)δ:14.4、 23.6、 27.0、 30.2、
30.3、 30.4、 32.9、 37.1、 43.8、 56.6、 62.3、 71.4、 7
3.7、 74.5、 75.0、 101.0、 113.4、 119.9、 121.2、 135.
7、 146.7、 151.9、 176.0 比旋光度 〔α〕D 24 ＋１１３.５°（ｃ ０.８，ＣＨ3ＯＨ）Id mp 174-177 ° C. IR (KBr): 3300, 2900, 2840, 1640, 1545, 1515, 1275,
1230, 1110, 1090, 1055, 1030, 1010cm -1 1 H-NMR (400MHz, CD 3 OD) δ: 0.89 (3H, t, J = 6.8Hz), 1.
3 (10H, m), 1.62 (2H, m), 2.21 (2H, t, J = 7.5Hz),
3.42 (1H, dd, J = 10.0, 9.0Hz), 3.51 (1H, dd, J = 10.0,
3.7Hz), 3.7 (2H, m), 3.8 (1H, m), 3.84 (3H, s), 3.
86 (1H, t, J = 10.0Hz), 4.29 (2H, s), 4.9 (br, -NH,
-OH), 5.40 (1H, d, J = 3.7 Hz), 6.81 (1H, dd, J = 8.2,
2.0Hz), 6.94 (1H, d, J = 2.0Hz), 7.14 (1H, d, J = 8.2H
z) 13 C-NMR (100 MHz, CD 3 OD) δ: 14.4, 23.6, 27.0, 30.2,
30.3, 30.4, 32.9, 37.1, 43.8, 56.6, 62.3, 71.4, 7
3.7, 74.5, 75.0, 101.0, 113.4, 119.9, 121.2, 135.
7, 146.7, 151.9, 176.0 Specific rotation [α] D 24 + 113.5 ° (c 0.8, CH 3 OH)
Claims (1)
たはアルケニル基を示し、Ｒ2は所望により水酸基が保
護された糖残基を示す）で表わされるカプサイシノイド
配糖体。1. Formula (I): (In the formula, R 1 represents an alkyl group or an alkenyl group having 7 to 12 carbon atoms, and R 2 represents a sugar residue in which a hydroxyl group is optionally protected), which is a capsaicinoid glycoside.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP06283892A JP3156240B2 (en) | 1991-03-20 | 1992-03-19 | Capsaicinoid glycosides |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3-80387 | 1991-03-20 | ||
| JP8038791 | 1991-03-20 | ||
| JP06283892A JP3156240B2 (en) | 1991-03-20 | 1992-03-19 | Capsaicinoid glycosides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0586086A true JPH0586086A (en) | 1993-04-06 |
| JP3156240B2 JP3156240B2 (en) | 2001-04-16 |
Family
ID=26403893
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP06283892A Expired - Fee Related JP3156240B2 (en) | 1991-03-20 | 1992-03-19 | Capsaicinoid glycosides |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3156240B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000016756A3 (en) * | 1998-09-24 | 2000-09-08 | Innovet Italia Srl | Use of n-acylvanillinamide derivatives as agonists of peripheral cannabinoid cb1 receptors |
| WO2021182398A1 (en) * | 2020-03-10 | 2021-09-16 | 株式会社フジキン | Pipe joint |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4514406B2 (en) * | 2003-01-14 | 2010-07-28 | サニーヘルス株式会社 | Method for obtaining capsaicin-β-D-glucopyranoside derived from Capsaicinnum species |
-
1992
- 1992-03-19 JP JP06283892A patent/JP3156240B2/en not_active Expired - Fee Related
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000016756A3 (en) * | 1998-09-24 | 2000-09-08 | Innovet Italia Srl | Use of n-acylvanillinamide derivatives as agonists of peripheral cannabinoid cb1 receptors |
| US7244767B2 (en) | 1998-09-24 | 2007-07-17 | Innovet Italia S.R.L. | N-acylvanillinamide derivatives capable of activating peripheral cannabinoid receptors |
| WO2021182398A1 (en) * | 2020-03-10 | 2021-09-16 | 株式会社フジキン | Pipe joint |
| KR20220145404A (en) | 2020-03-10 | 2022-10-28 | 가부시키가이샤 후지킨 | pipe joint |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3156240B2 (en) | 2001-04-16 |
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