JP2796183B2 - Process for producing capsaicinol and intermediates thereof - Google Patents
Process for producing capsaicinol and intermediates thereofInfo
- Publication number
- JP2796183B2 JP2796183B2 JP22894290A JP22894290A JP2796183B2 JP 2796183 B2 JP2796183 B2 JP 2796183B2 JP 22894290 A JP22894290 A JP 22894290A JP 22894290 A JP22894290 A JP 22894290A JP 2796183 B2 JP2796183 B2 JP 2796183B2
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- added
- methyl
- hydroxy
- iii
- capsaicinol
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Description
【発明の詳細な説明】 産業上の利用分野 本発明は、強い抗酸化作用を有するカプサイシノール
〔Ｎ−（４−ヒドロキシ−３−メトキシベンジル）−７
−ヒドロキシ−８−メチル−（Ｅ）−５−ノネンアミ
ド〕の製造法およびその中間体に関する。Description: TECHNICAL FIELD The present invention relates to capsaicinol [N- (4-hydroxy-3-methoxybenzyl) -7 having a strong antioxidant action.
-Hydroxy-8-methyl- (E) -5-nonenamide] and an intermediate thereof.
従来の技術 カプサイシノールは、インドネシア産のシマトウガラ
シ（Capsicum frutescens L.）の果実より単離され、既
に構造決定されたカプサイシノイドであり、強い抗酸化
作用を有することが知られている〔メディカル・バイオ
ケミカル・アンド・ケミカル・アスペクツ・オブ・フリ
ー・ラジカルズ（Medical,Biochemical and Chemical A
spects of Free Radicals）453頁（1988年）〕。2. Description of the Related Art Capsaicinol is a capsaicinoid that has been isolated from the fruits of Indonesian capsicum (Capsicum frutescens L.) and has already been determined in structure, and is known to have a strong antioxidant effect [Medical Biochemicals]・ Chemical Aspects of Free Radicals (Medical, Biochemical and Chemical A
spects of Free Radicals) 453 (1988)].
しかしながら、合成法による製造法については知られ
ていない。However, a production method by a synthesis method is not known.
発明が解決しようとする課題 本発明の目的は、カプサイシノールの効率的な製造法
を提供することにある。SUMMARY OF THE INVENTION An object of the present invention is to provide an efficient method for producing capsaicinol.
課題を解決するための手段 本発明によれば、７−ヒドロキシ−８−メチル−
（Ｅ）−５−ノネン酸 ｐ−ニトロフェニルエステルと
４−ヒドロキシ−３−メトキシベンジルアミンまたはそ
の酸塩とを反応させることによりカプサイシノールを製
造することができ、また下記式（III）で表わされるカ
プサイシノールの合成中間体も提供することができる。Means for Solving the Problems According to the present invention, 7-hydroxy-8-methyl-
Capsaicinol can be produced by reacting (E) -5-nonenoic acid p-nitrophenyl ester with 4-hydroxy-3-methoxybenzylamine or an acid salt thereof, and is represented by the following formula (III): Synthetic intermediates for capsaicinol can also be provided.
式（III）中、ＸおよびＹは一緒になって酸素原子を
表わし、Ｚがメチル基を表わすか、あるいはＸまたはＹ
の一方が水素原子で他方が水酸基を表わし、Ｚが水素原
子、メチル基またはｐ−ニトロフェニル基を表わす。 In the formula (III), X and Y together represent an oxygen atom, Z represents a methyl group, or X or Y
Is a hydrogen atom, the other is a hydroxyl group, and Z is a hydrogen atom, a methyl group or a p-nitrophenyl group.
カプサイシノールは、以下に示す反応式で例示される
方法で製造することができる。Capsaicinol can be produced by a method exemplified by the following reaction formula.
反応式中、式（II）で表わされるアルデヒド誘導体は
公知化合物であり、製法はシンセシス（Synthesis）、8
81頁（1982年）に記載されている。 In the reaction formula, the aldehyde derivative represented by the formula (II) is a known compound, and the production method is Synthesis, 8
It is described on page 81 (1982).
アルデヒド誘導体（II）に、イソプロピルメチルケト
ンとリチウムジイソプロピルアミドより生成させたリチ
ウムエノレートを付加し、ついで生成した水酸基をトシ
ル化もしくはメシル化後、トリエチルアミンなどの塩基
で脱離させることにより化合物（III−１）を得ること
ができる。Lithium enolate generated from isopropyl methyl ketone and lithium diisopropylamide is added to the aldehyde derivative (II), and the generated hydroxyl group is tosylated or mesylated and then eliminated with a base such as triethylamine to obtain the compound (III) -1) can be obtained.
得られた化合物（III−１）をリチウムアルミニウム
ハイドライドなどの還元剤を用いて還元することにより
アルコール体（III−２）を得ることができる。化合物
（III−２）を好ましくは水酸化ナトリウムなどの塩基
の存在下、加水分解してカルボン酸（III−３）を得
る。The alcohol (III-2) can be obtained by reducing the obtained compound (III-1) using a reducing agent such as lithium aluminum hydride. Hydrolysis of compound (III-2), preferably in the presence of a base such as sodium hydroxide, gives carboxylic acid (III-3).
次いで化合物（III−３）をジシクロヘキシルカルボ
ジイミドなどの縮合剤の存在下にｐ−ニトロフェノール
と反応させることにより活性エステル体（III−４）を
得る。Next, the compound (III-3) is reacted with p-nitrophenol in the presence of a condensing agent such as dicyclohexylcarbodiimide to obtain an active ester (III-4).
次いで、化合物（III−４）を好ましくは塩基の存在
下、４−ヒドロキシ−３−メトキシベンジルアミンまた
はその酸塩と反応させることによりカプサイシノール
（Ｉ）を得ることができる。塩基としては、４−ヒドロ
キシ−３−メトキシベンジルアミンの酸塩を中和するこ
とができればよく、たとえばトリメチルアミン、トリエ
チルアミン、４−ジメチルアミンピリジン、水酸化ナト
リウムなどをあげることができる。とくにトリエチルア
ミンが好ましい。酸塩としては、塩酸塩、硫酸塩、臭化
水素酸塩などをあげることができる。とくに塩酸塩が好
ましい。Next, capsaicinol (I) can be obtained by reacting compound (III-4) with 4-hydroxy-3-methoxybenzylamine or an acid salt thereof, preferably in the presence of a base. The base only needs to be able to neutralize the acid salt of 4-hydroxy-3-methoxybenzylamine, and examples thereof include trimethylamine, triethylamine, 4-dimethylaminepyridine, and sodium hydroxide. Triethylamine is particularly preferred. Examples of the acid salt include hydrochloride, sulfate, hydrobromide and the like. Particularly preferred is the hydrochloride salt.
上述した製造法における中間体および目的化合物は、
有機合成化学で常用される精製法、たとえば過、抽
出、洗浄、乾燥、濃縮、再結晶、各種クロマトグラフィ
ーなどに付して単離精製することができる。また中間体
においては、特に精製することなく次の反応に供するこ
とも可能である。Intermediates and target compounds in the above-mentioned production method,
Isolation and purification can be performed by a purification method commonly used in organic synthetic chemistry, for example, filtration, extraction, washing, drying, concentration, recrystallization, various types of chromatography, and the like. In addition, the intermediate can be subjected to the next reaction without purification.
以下に本発明の実施例を示す。 Hereinafter, examples of the present invention will be described.
実施例１ ７−ケト−８−メチル−（Ｅ）−５−ノネン酸メチルエ
ステル 窒素雰囲気下、無水テトラヒドロフラン100mlに1.5N
リチウムジイソプロピルアミド／ヘキサン溶液95mlを加
え−78℃に冷却し、３−メチル−２−ブタノン12.4mlを
滴下後０℃まで昇温した。反応液を再度−78℃に冷却
後、５−オキソペンタン酸 メチルエステル14.4ml/テ
トラヒドロフラン200ml溶液を窒素雰囲気下15分かけて
滴下した。滴下終了後、同温度でさらに10分間撹拌した
後、酢酸を加えて反応液のpHを酸性にした。得られた溶
液を飽和重曹水に加え塩化メチレンで４回抽出した。有
機層を合わせ無水芒硝で乾燥後減圧濃縮した。得られた
残渣をシリカゲルカラムクロマトグラフィー（メルク社
製Kieselgel 60 Art 7734 600g）に付し、酢酸エチル／
ヘキサン＝1/3で溶出して、16.9gの油状物を得た。Example 1 7-keto-8-methyl- (E) -5-nonenoic acid methyl ester 1.5N in 100 ml of anhydrous tetrahydrofuran under a nitrogen atmosphere.
95 ml of a lithium diisopropylamide / hexane solution was added, the mixture was cooled to -78 ° C, 12.4 ml of 3-methyl-2-butanone was added dropwise, and the temperature was raised to 0 ° C. After the reaction solution was cooled again to -78 ° C, a solution of methyl 5-oxopentanoate (14.4 ml) / tetrahydrofuran (200 ml) was added dropwise over 15 minutes under a nitrogen atmosphere. After completion of the dropwise addition, the mixture was further stirred at the same temperature for 10 minutes, and acetic acid was added to acidify the pH of the reaction solution. The obtained solution was added to a saturated aqueous solution of sodium bicarbonate and extracted four times with methylene chloride. The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (Kieselgel 60 Art 7734, 600 g, manufactured by Merck) to give ethyl acetate /
Elution with hexane = 1/3 gave 16.9 g of an oil.
この油状物4.6gに無水ピリジン46mlおよび塩化メチレ
ン46mlを添加し、得られた溶液に室温でｐ−トルエンス
ルホニルクロライド6.1gを10分間かけて添加した。同温
度で21時間撹拌後、飽和重曹水に加え、塩化メチレンで
４回抽出した。有機層を合わせ無水芒硝で乾燥後、減圧
濃縮した。得られた残渣にジクロロエタン140mlを添加
しトリエチルアミン12mlを加え室温で３時間撹拌した。
反応液を同容量の1N塩酸に加え塩化メチレンで３回抽出
した。有機層を合わせ無水芒硝で乾燥後、減圧濃縮し
た。得られた残渣をシリカゲルカラムクロマトグラフィ
ー（メルク社製Kieselgel 60 Art 7734 230g）に付し、
酢酸エチル／ヘキサン＝1/6で溶出して、７−ケト−８
−メチル−（Ｅ）−５−ノネン酸 メチルエステル（II
I−１）3.6g（IIからの通算収率 57％）を得た。1 H−NMR（CDCl3）δ（ppm）:1.10（6H,d,J＝7.3Hz）,1.
82（2H,m）,2.22〜2.46（4H,m）,2.81（1H,sept,J＝7.3
Hz）,3.68（3H,s）,6.20（1H,d,J＝15.9Hz）,6.84（1H,
dt,J＝15.9,7.3Hz） IR（neat）cm-1 1745,1695,1675,1630 MS（m/z） 198（M+） 実施例２ ７−ケト−８−メチル−（Ｅ）−５−ノネン酸メチルエ
ステル（別法） 実施例１と同様の方法で５−オキソペンタン酸メチル
エステルのリチウムエノレート付加体を得た。この油状
物10.8gに無水ピリジン110mlおよび塩化メチレン110ml
を添加し、得られた溶液に室温でメシルクロライド5.8m
lを５分間で滴下した。同温度で２時間撹拌後、飽和重
曹水に加え、塩化メチレンで４回抽出した。有機層を合
わせ無水芒硝で乾燥後、減圧濃縮した。以下、実施例１
と同様にトリエチルアミン処理し、得られた残渣をシリ
カゲルカラムクロマトグラフィー（メルク社製Kieselge
l 60 Art 7734 550g）に付し、酢酸エチル／ヘキサン＝
1/6で溶出して、７−ケト−８−メチル−（Ｅ）−５−
ノネン酸 メチルエステル（III−１）8.6g（IIからの
通算収率 58％）を得た。To 4.6 g of this oil was added 46 ml of anhydrous pyridine and 46 ml of methylene chloride, and 6.1 g of p-toluenesulfonyl chloride was added to the resulting solution at room temperature over 10 minutes. After stirring at the same temperature for 21 hours, the mixture was added to saturated aqueous sodium hydrogen carbonate and extracted four times with methylene chloride. The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. 140 ml of dichloroethane was added to the obtained residue, 12 ml of triethylamine was added, and the mixture was stirred at room temperature for 3 hours.
The reaction solution was added to an equal volume of 1N hydrochloric acid and extracted three times with methylene chloride. The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (Kieselgel 60 Art 7734 230 g, manufactured by Merck),
Elution with 1/6 ethyl acetate / hexane gave 7-keto-8
-Methyl- (E) -5-nonenoic acid methyl ester (II
I-1) 3.6 g (total yield from II 57%) was obtained. 1 H-NMR (CDCl 3 ) δ (ppm): 1.10 (6H, d, J = 7.3 Hz), 1.
82 (2H, m), 2.22 ~ 2.46 (4H, m), 2.81 (1H, sept, J = 7.3
Hz), 3.68 (3H, s), 6.20 (1H, d, J = 15.9Hz), 6.84 (1H,
dt, J = 15.9,7.3 Hz) IR (neat) cm -1 1745,1695,1675,1630 MS (m / z) 198 (M + ) Example 2 7-keto-8-methyl- (E) -5 -Nonenoic acid methyl ester (alternative method) A lithium enolate adduct of methyl 5-oxopentanoate was obtained in the same manner as in Example 1. To 10.8 g of this oil, 110 ml of anhydrous pyridine and 110 ml of methylene chloride
Was added, and mesyl chloride 5.8m was added to the obtained solution at room temperature.
l was added dropwise over 5 minutes. After stirring at the same temperature for 2 hours, the mixture was added to saturated aqueous sodium hydrogen carbonate and extracted four times with methylene chloride. The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. Hereinafter, Example 1
The residue obtained was treated with silica gel column chromatography (Kieselge, Merck).
l 60 Art 7734 550g) and ethyl acetate / hexane =
Elution at 1/6 gave 7-keto-8-methyl- (E) -5
8.6 g of nonenoic acid methyl ester (III-1) (total yield from II: 58%) was obtained.
本化合物の理化学的データは実施例１で得られた化合
物のそれに一致した。The physicochemical data of this compound was identical to that of the compound obtained in Example 1.
実施例３ ７−ヒドロキシ−８−メチル−（Ｅ）−５−ノネン酸
メチルエステル 実施例１あるいは２で得られたケトン体（III−１）
7.4gに無水テトラヒドロフラン140mlを加え、窒素雰囲
気下−78℃に冷却した。この溶液に1Nリチウムアルミニ
ウムハイドライド／テトラヒドロフラン溶液41mlを滴下
した。滴下終了後同温度で10分間撹拌した後、反応液に
酢酸エチル10mlおよび塩化メチレン200mlを添加した。
この溶液を飽和セニェット塩水に加え、塩化メチレンで
４回抽出した。有機層を合わせ無水芒硝で乾燥後、減圧
濃縮した。得られた残渣をシリカゲルカラムクロマトグ
ラフィー（メルク社製Kieselgel 60 Art 7734 370g）に
付し、酢酸エチル／ヘキサン＝1/4で溶出して、７−ヒ
ドロキシ−８−メチル−（Ｅ）−５−ノネン酸 メチル
エステル（III−２）5.6g（収率 75％）を得た。1 H−NMR（CDCl3）δ（ppm）:0.86（3H,d,J＝6Hz）,0.91
（3H,d,J＝6Hz）,1.4〜2.5（7H,m）,3.66（3H,s）,3.76
（1H,m）,5.40〜5.70（2H,m） IR（neat）cm-1 3460,1733 MS（m/z） 182（M+−H2O） 実施例４ ７−ヒドロキシ−８−メチル−（Ｅ）−５−ノネン酸
ｐ−ニトロフェニルエステル 実施例３で得られたヒドロキシ体（III−２）99.7mg
をメタノール3mlに溶解し、室温で1N水酸化ナトリウム2
mlを添加した。反応液を同温度でさらに１時間撹拌した
後、1N塩酸に加え酢酸エチルで４回抽出した。有機層を
合わせ無水芒硝で乾燥後、減圧濃縮し、粗カルボン酸体
（III−３）を得た。Example 3 7-Hydroxy-8-methyl- (E) -5-nonenoic acid
Methyl ester Ketone (III-1) obtained in Example 1 or 2
140 ml of anhydrous tetrahydrofuran was added to 7.4 g, and the mixture was cooled to -78 ° C under a nitrogen atmosphere. 41 ml of a 1N lithium aluminum hydride / tetrahydrofuran solution was added dropwise to this solution. After completion of the dropwise addition, the mixture was stirred at the same temperature for 10 minutes, and 10 ml of ethyl acetate and 200 ml of methylene chloride were added to the reaction solution.
This solution was added to saturated sennette brine and extracted four times with methylene chloride. The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (Kieselgel 60 Art 7734, 370 g, manufactured by Merck), and eluted with ethyl acetate / hexane = 1/4 to give 7-hydroxy-8-methyl- (E) -5. 5.6 g (75% yield) of nonenic acid methyl ester (III-2) was obtained. 1 H-NMR (CDCl 3 ) δ (ppm): 0.86 (3H, d, J = 6 Hz), 0.91
(3H, d, J = 6Hz), 1.4 ~ 2.5 (7H, m), 3.66 (3H, s), 3.76
(1H, m), 5.40~5.70 ( 2H, m) IR (neat) cm -1 3460,1733 MS (m / z) 182 (M + -H 2 O) Example 4 7-hydroxy-8-methyl - (E) -5-Nonenoic acid
p-Nitrophenyl ester 99.7 mg of the hydroxy compound (III-2) obtained in Example 3
Was dissolved in 3 ml of methanol, and 1N sodium hydroxide 2 was added at room temperature.
ml was added. After the reaction solution was further stirred at the same temperature for 1 hour, it was added to 1N hydrochloric acid and extracted four times with ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude carboxylic acid compound (III-3).
このものは、さらに精製することなく塩化メチレン2.
2mlおよびジメチルホルムアミド0.4mlに溶解し、０℃に
冷却した後、ｐ−ニトロフェノール123mg、ジシクロヘ
キシルカルボジイミド182mgを順次添加した。室温で１
時間撹拌後生じた不溶物を別し、液を減圧濃縮し
た。It was obtained without further purification.
After dissolving in 2 ml and 0.4 ml of dimethylformamide and cooling to 0 ° C., 123 mg of p-nitrophenol and 182 mg of dicyclohexylcarbodiimide were sequentially added. 1 at room temperature
After stirring for an hour, insolubles generated were separated, and the solution was concentrated under reduced pressure.
得られた残渣をシリカゲル分取薄層クロマトグラフィ
ー（メルク社製Kieselgel F254 Art 5717）に付し、メ
タノール／塩化メチレン＝5/95で展開して、７−ヒドロ
キシ−８−メチル−（Ｅ）−５−ノネン酸 ｐ−ニトロ
フェニルエステル（III−４）115mg（収率 60％）を得
た。1 H−NMR（CDCl3）δ（ppm）:1.00（3H,d,J＝6Hz）,1.05
（3H,d,J＝6Hz）,1.5〜2.5（7H,m）,3.98（1H,brt,J＝6
Hz）,5.60〜5.85（2H,m）,7.38（2H,d,J＝8Hz）,8.35
（2H,d,J＝8Hz） 実施例５ Ｎ−（４−ヒドロキシ−３−メトキシベンジル）−７−
ヒドロキシ−８−メチル−（Ｅ）−５−ノネンアミド 実施例４で得られた化合物（III−４）103mgをジメチ
ルホルムアミド1mlに溶解し、この溶液に４−ヒドロキ
シ−３−メトキシベンジルアミン塩酸塩112mgおよびト
リメチルアミン290μ／ジメチルホルムアミド2ml溶液
を添加した。室温で10分間撹拌後、反応液を冷1N塩酸に
加え、塩化メチレンで４回抽出した。有機層を合わせ、
無水芒硝で乾燥後減圧濃縮した。得られた残渣をシリカ
ゲル分取薄層クロマトグラフィー（メルク社製Kieselge
l F254 Art 5717）に付し、酢酸エチルで展開してＮ−
（４−ヒドロキシ−３−メトキシベンジル）−７−ヒド
ロキシ−８−メチル−（Ｅ）−５−ノネンアミド（Ｉ）
104mg（収率100％）を得た。The obtained residue was subjected to silica gel preparative thin-layer chromatography (Kieselgel F 254 Art 5717, manufactured by Merck) and developed with methanol / methylene chloride = 5/95 to give 7-hydroxy-8-methyl- (E). 115 mg (yield 60%) of p-nitrophenyl-5-nonenoic acid ester (III-4) was obtained. 1 H-NMR (CDCl 3 ) δ (ppm): 1.00 (3H, d, J = 6 Hz), 1.05
(3H, d, J = 6Hz), 1.5 ~ 2.5 (7H, m), 3.98 (1H, brt, J = 6
Hz), 5.60-5.85 (2H, m), 7.38 (2H, d, J = 8Hz), 8.35
(2H, d, J = 8 Hz) Example 5 N- (4-hydroxy-3-methoxybenzyl) -7-
Hydroxy-8-methyl- (E) -5-nonenamide 103 mg of the compound (III-4) obtained in Example 4 was dissolved in 1 ml of dimethylformamide, and 112 mg of 4-hydroxy-3-methoxybenzylamine hydrochloride was added to this solution. And a solution of 290 μm of trimethylamine in 2 ml of dimethylformamide were added. After stirring at room temperature for 10 minutes, the reaction solution was added to cold 1N hydrochloric acid and extracted four times with methylene chloride. Combine the organic layers,
After drying over anhydrous sodium sulfate, the mixture was concentrated under reduced pressure. The obtained residue is subjected to silica gel preparative thin-layer chromatography (Kieselge manufactured by Merck).
l F 254 Art 5717), and develop with ethyl acetate to give N-
(4-hydroxy-3-methoxybenzyl) -7-hydroxy-8-methyl- (E) -5-nonenamide (I)
104 mg (100% yield) were obtained.
本化合物の1H−NMR（CDCl3）スペクトルは天然のカプ
サイシノールに一致した。The 1 H-NMR (CDCl 3 ) spectrum of this compound was consistent with natural capsaicinol.
発明の効果 本発明によれば、効率的にカプサイシノールを製造す
ることができる。Effects of the Invention According to the present invention, capsaicinol can be efficiently produced.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 ＦＩ Ｃ０７Ｃ 231/02 Ｃ０７Ｃ 231/02 (58)調査した分野(Int.Cl.6，ＤＢ名) C07C 235/28,231/02,59/42,69/732,69 /738,205/43 ＣＡ（ＳＴＮ)──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. 6 identification code FI C07C 231/02 C07C 231/02 (58) Field surveyed (Int. Cl. 6 , DB name) C07C 235 / 28,231 / 02,59 / 42,69 / 732,69 / 738,205 / 43 CA (STN)
Claims (2)
−ノネン酸 ｐ−ニトロフェニルエステルと、４−ヒド
ロキシ−３−メトキシベンジルアミンまたはその酸塩と
を反応させることを特徴とするカプサイシノールの製造
法。(1) 7-hydroxy-8-methyl- (E) -5
-A method for producing capsaicinol, comprising reacting p-nitrophenyl nonenoic acid with 4-hydroxy-3-methoxybenzylamine or an acid salt thereof.
し、Ｚがメチル基を表わすか、あるいはＸまたはＹの一
方が水素原子で他方が水酸基を表わし、Ｚが水素原子、
メチル基またはｐ−ニトロフェニル基を表わす。）で表
わされる化合物。2. A compound of the general formula (III) (Wherein, X and Y together represent an oxygen atom, Z represents a methyl group, or one of X or Y represents a hydrogen atom and the other represents a hydroxyl group, Z represents a hydrogen atom,
Represents a methyl group or a p-nitrophenyl group. ).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22894290A JP2796183B2 (en) | 1990-08-30 | 1990-08-30 | Process for producing capsaicinol and intermediates thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22894290A JP2796183B2 (en) | 1990-08-30 | 1990-08-30 | Process for producing capsaicinol and intermediates thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04108769A JPH04108769A (en) | 1992-04-09 |
| JP2796183B2 true JP2796183B2 (en) | 1998-09-10 |
Family
ID=16884269
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22894290A Expired - Lifetime JP2796183B2 (en) | 1990-08-30 | 1990-08-30 | Process for producing capsaicinol and intermediates thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2796183B2 (en) |
-
1990
- 1990-08-30 JP JP22894290A patent/JP2796183B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH04108769A (en) | 1992-04-09 |
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