JPS593459B2 - Isoprenyl chalcone Ruino Goseihou - Google Patents
Isoprenyl chalcone Ruino GoseihouInfo
- Publication number
- JPS593459B2 JPS593459B2 JP48074075A JP7407573A JPS593459B2 JP S593459 B2 JPS593459 B2 JP S593459B2 JP 48074075 A JP48074075 A JP 48074075A JP 7407573 A JP7407573 A JP 7407573A JP S593459 B2 JPS593459 B2 JP S593459B2
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- Prior art keywords
- methyl
- compound
- ether
- chalcone
- isoprenyl
- Prior art date
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Description
【発明の詳細な説明】
本発明は、イソプレニルカルコン類の合成法に関し、抗
消化性潰瘍作用を呈する化合物の製法を提供するもので
ある。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for synthesizing isoprenyl chalcone, and provides a method for producing a compound exhibiting anti-peptic ulcer activity.
本発明は、
一般式
〔式中、Ｒ１およびＲ２は水素原子または３−メチル−
２−ブテニル基を示す。The present invention is based on the general formula [wherein R1 and R2 are hydrogen atoms or 3-methyl-
Indicates a 2-butenyl group.
〕で表わされるイソプレニルカルコン類を合成するに当
り、一般式
〔式中、Ｒ３は前記Ｒ１が水素原子のとき水素原子であ
り、前記Ｒ１が３−メチル−２−ブテニル基のとき３−
メチル− ２ −ブテニル基である。] When synthesizing isoprenyl chalcone compounds represented by the general formula [wherein R3 is a hydrogen atom when R1 is a hydrogen atom, and when R1 is a 3-methyl-2-butenyl group, 3-
It is a methyl-2-butenyl group.
Ｒ４は前記Ｒ２が水素原子のとき水素原子であり、前記
Ｒ２が３−メチル−２−ブテニル基のとき３一メチル一
２ −ブテニル基である。〕で表わされる化合物を加
熱し、転位させることを特徴とするイソプレニルカルコ
ン類の合成法である。R4 is a hydrogen atom when R2 is a hydrogen atom, and is a 3-methyl-12-butenyl group when R2 is a 3-methyl-2-butenyl group. ] This is a method for synthesizing isoprenyl chalcone, which is characterized by heating and rearranging the compound represented by the following.
本発明の加熱転位に当つては、化合物丁をジエチルアニ
リン、ジメチルフオルムアマイド、ジブチルアミン、へ
キサデシルアミンなどの溶剤に溶解もしくは懸濁させ、
または溶剤を用いることなしに窒素の存在下、あるいは
非存在下に温度１００〜２００℃で数時間加熱し、必要
に応じて再結晶法、カラムクロマトグラフイー法などに
より精製して化合物Ｉを得ることができる。In the thermal rearrangement of the present invention, compound D is dissolved or suspended in a solvent such as diethylaniline, dimethylformamide, dibutylamine, hexadecylamine, etc.
Alternatively, heat for several hours at a temperature of 100 to 200°C in the presence or absence of nitrogen without using a solvent, and purify by recrystallization, column chromatography, etc. as necessary to obtain Compound I. be able to.
化合物Ｉ’は、 一般式 （式中、Ｒ３は前記と同義である） で表わされる化合物と、 一般式 （式中、Ｒ４は前記と同義である。Compound I' is general formula (In the formula, R3 has the same meaning as above) A compound represented by general formula (In the formula, R4 has the same meaning as above.
）で表わされる化合物とを縮合させることによつて製造
することができる。) can be produced by condensing with the compound represented by
この縮合に当つては、化合物と化合物とをメタノール、
エタノール、酢酸エチルなどの有機溶媒に溶解もしくは
懸濁させ、苛性カリ、苛性ソーダなどのアルカリ、ある
いは硫酸、塩化水素などの酸を加え、これを３０〜７０
℃で数時間、または室温で数日間、攪拌もしくは放置し
て反応を完結させ、生成した縮合物を反応液から有機溶
媒などを用いて分離する。化合物または化合物は、次の
方法で製造することができる。For this condensation, methanol,
Dissolve or suspend in an organic solvent such as ethanol or ethyl acetate, add an alkali such as caustic potash or caustic soda, or an acid such as sulfuric acid or hydrogen chloride, and add 30 to 70 ml of this solution.
The reaction is completed by stirring or standing for several hours at °C or several days at room temperature, and the resulting condensate is separated from the reaction solution using an organic solvent or the like. The compound or compound can be manufactured by the following method.
１２・４−ジハイドロキシアセトフエノンまたはパラハ
イドロキシベンズアルデヒドに２−クロロ−２−メチル
−３−ブチンを反応させた後、リンドラ一触媒などで還
元することによりそれぞれＲ３が水素原子である化合物
またはＲ４が水素原子である化合物を得ることができる
。A compound in which R3 is a hydrogen atom or R4 is obtained by reacting 12,4-dihydroxyacetophenone or parahydroxybenzaldehyde with 2-chloro-2-methyl-3-butyne and then reducing it with a Lindlar catalyst or the like. is a hydrogen atom.
２前項１で得た化合物または化合物を前記の加熱転位反
応に準じて処理することにより、それぞれ２・４−ジハ
イドロキシ−３−（３メチル−２−ブテニル）−アセト
フエノンまたは４−ハイドロキシ−３−（３−メチル−
２ブテニル）−ベンズアルデヒドとなし、これに更に２
−クロロ−２−メチル−３−ブチンを反応させてＲ３が
３−メチル−２−ブテニル基である化合物またはＲ４が
３−メチル−２−ブテニル基である化合物を得ることが
できる。2. By treating the compound or compounds obtained in the previous section 1 according to the above-mentioned thermal rearrangement reaction, 2,4-dihydroxy-3-(3methyl-2-butenyl)-acetophenone or 4-hydroxy-3- (3-methyl-
2-butenyl)-benzaldehyde, and further 2
A compound in which R3 is a 3-methyl-2-butenyl group or a compound in which R4 is a 3-methyl-2-butenyl group can be obtained by reacting -chloro-2-methyl-3-butyne.
３あるいはまた、前項１で得た化合物または化合物にγ
・γ−ジメチルアリルブロマイドまたは３−ハイドロキ
シ−３−メチル−１−ブテンをアルカリ存在下に反応さ
せて、Ｒ３が３ーメチル−２−ブテニル基である化合物
またはＲ４が３−メチル−２−ブテニル基である化合物
を得ることができる。3 Alternatively, the compound obtained in the previous section 1 or the compound γ
・A compound in which R3 is a 3-methyl-2-butenyl group or R4 is a 3-methyl-2-butenyl group by reacting γ-dimethylallyl bromide or 3-hydroxy-3-methyl-1-butene in the presence of an alkali A compound can be obtained.
本発明で得られた化合物１は優れた抗消化性潰瘍活性を
示した。Compound 1 obtained according to the present invention showed excellent anti-peptic ulcer activity.
たとえばラツトを用いた実験潰瘍の抑制率は実施例１の
化合物１（ソフオラジン）と実施例４の化合物１におい
て、下記の如くであつた。すなわち、高木の酢酸潰瘍法
で８０Ｗ１９／Ｋｇを経口投与した場合の抑制率は、前
者が４８４１％、後者が５４．６％であり、また幽門結
紮法で４０Ｗ１ｙ／Ｋｇを腹腔内投与したときの抑制率
は、前者が６１．６％、後者が７４．１％であつた。For example, the inhibition rates of experimental ulcers in rats were as follows for Compound 1 (Sophorazine) of Example 1 and Compound 1 of Example 4. That is, the inhibition rate when 80W1y/Kg was orally administered using Takagi's acetic acid ulcer method was 4841% for the former and 54.6% for the latter, and when 40W1y/Kg was administered intraperitoneally using the pyloric ligation method. The inhibition rate was 61.6% for the former and 74.1% for the latter.
次に実施例を挙げて本発明を具体的に説明する。Next, the present invention will be specifically explained with reference to Examples.
実施例 １２・４−ジハイドロキシアセトフエノン１６
．０７を７０ｍ１のジメチルフオルムアマイドに溶かし
、炭酸カリ２３．２ｆと沃度カリ０．８Ｖを加え、７０
８０℃に加熱しながら２−クロロ−２−メチル３−ブチ
ン１５．０ｔを加え６時間後、水を加えてエーテルで抽
出し、エーテル層を希アルカリと水で洗浄した後、エー
テルを留去し、２・４−ジハイドロキシ−４−０−（１
・１−ジメチルプロパルギル）アセトフエノン（）６．
２７を得た。Example 12,4-dihydroxyacetophenone 16
．． Dissolve 07 in 70ml of dimethyl formamide, add 23.2f of potassium carbonate and 0.8V of potassium iodide,
15.0 tons of 2-chloro-2-methyl-3-butyne was added while heating to 80°C, and after 6 hours, water was added and extracted with ether. The ether layer was washed with dilute alkali and water, and the ether was distilled off. and 2,4-dihydroxy-4-0-(1
・1-dimethylpropargyl)acetophenone ()6.
I got 27.
６．２Ｖの化合物（）を酢酸エチル２００ｍ１に溶かし
、リンドラ一触媒０．７７を加える。6.2V compound () is dissolved in 200ml of ethyl acetate, and 0.77ml of Lindlar catalyst is added.
室温１時間で水素当モルを吸収した。沢過後、溶媒を留
去し、酢酸エチル−ヘキサン混液で再結晶すると、無色
針状晶（ＭｐｌＯｌ℃）の２・４−ジハイドロキシ−４
−０−（１・１−ジメチルアリル）アセトフエノン（Ｖ
）を５．２ｔ得た。次にパラ・ハイドロキシベンズアル
デヒド１０．９７をジメチルフオルムアマイド４０ｍ１
に溶解し、窒素気流中、炭酸カリ１４．８ｔと沃度カリ
０．５７を加え、撹拌しながら７５℃に加温、２ークロ
ロ−２−メチル−３−ブチン１０．０ｙを加え、混合物
に７時間後に水を加えてエーテルで抽出し、エーテル層
を希アルカリと水で洗浄し、乾燥後、エーテルを留去し
、残留物を減圧蒸留（１０７１１０℃／２ｍｍＨｇ）す
ると４−ハイドロキシ４−０−（１・１−ジメチルプロ
パルギル）ベンズアルデヒド（）を４．８７得た。Equivalent moles of hydrogen were absorbed in 1 hour at room temperature. After filtration, the solvent was distilled off and recrystallized from a mixture of ethyl acetate and hexane, resulting in colorless needle-like crystals (MplOl°C) of 2,4-dihydroxy-4
-0-(1,1-dimethylallyl)acetophenone (V
) was obtained in an amount of 5.2 tons. Next, add 10.97 ml of para-hydroxybenzaldehyde to 40 ml of dimethylformamide.
14.8 t of potassium carbonate and 0.57 iodine of potassium were added in a nitrogen stream, heated to 75°C with stirring, 10.0 y of 2-chloro-2-methyl-3-butyne was added, and the mixture was After 7 hours, water was added and extracted with ether. The ether layer was washed with dilute alkali and water. After drying, the ether was distilled off. The residue was distilled under reduced pressure (107110℃/2mmHg) to obtain 4-hydroxy 4-0. -(1,1-dimethylpropargyl)benzaldehyde () was obtained in an amount of 4.87.
４．８ｙの化合物（）をエーテル５０ｍ１に溶かし、リ
ンドラ一触媒０，６Ｖを加えて還元後沢過し、エーテル
を減圧留去し４−ハイドロキシ−４−０−（１・１ジメ
チルアリル）ベンズアルデヒド（）３．０７得た。4.8y compound () was dissolved in 50 ml of ether, reduced by adding 0.6 V of Lindora catalyst, filtered, and the ether was distilled off under reduced pressure to give 4-hydroxy-4-0-(1.1 dimethylallyl)benzaldehyde. ()3.07 obtained.
６．０ｆの化合物（）をジエチルアニリン中、窒素を通
過させながら１６５−１７０℃に加温し、５時間後、エ
ーテルで抽出し、中性になるまで洗浄した後、乾燥、エ
ーテル留去、この残留物をシリカゲルカラムクロマトグ
ラフイ一（ベンゼン−イソプロピルエーテル混液）に供
し、３（３−メチル−２−ブテニル）−４−ハイドロキ
シベンズアルデヒド（）を４．８ｔ得た。The compound (6.0f) was heated to 165-170°C in diethylaniline while passing nitrogen through it, and after 5 hours, extracted with ether, washed until neutral, dried, and distilled off with ether. This residue was subjected to silica gel column chromatography (benzene-isopropyl ether mixture) to obtain 4.8 tons of 3(3-methyl-2-butenyl)-4-hydroxybenzaldehyde ().
４．８ｆ７の化合物（）をジメチルフオルムアマイド２
０ｍ１に溶解し、窒素気流中、炭酸カリ７．０７と沃度
カリ０．２５ｔを加え、室温で″１時間攪拌後、２クロ
ロ−２−メチル−３−ブチン４．５ｙを加え７０−８０
℃で５時間加熱する。4.8f7 compound () with dimethyl formamide 2
0 ml, add 7.07 t of potassium carbonate and 0.25 t of potassium iodide in a nitrogen stream, stir at room temperature for 1 hour, then add 4.5 y of 2chloro-2-methyl-3-butyne to 70-80 ml.
Heat at ℃ for 5 hours.
水を加えてエーテルで抽出し、エーテル層を希アルカリ
と水で洗浄し、乾燥後、エーテルを留去し、残留物に４
ハイドロキシ−３−（３−メチル−２−ブテニル）一４
−０−（１・１−ジメチルプロパルギル）ベンズアルデ
ヒド（）３，０ｆを得た。３。Water was added and extracted with ether, the ether layer was washed with dilute alkali and water, and after drying, the ether was distilled off and the residue was
Hydroxy-3-(3-methyl-2-butenyl)-4
-0-(1,1-dimethylpropargyl)benzaldehyde () 3,0f was obtained. 3.
０Ｖの化合物（）を３０ｍ１のエーテルに溶かし、リン
ドラ一触媒０．３７を加えて還元し、沢過後エーテルを
留去して４−ハイドロキシ−３−（３−メチル２−ブテ
ニル）−４−０−（１・１−ジメチルアリル）ベンズア
ルデヒド（Ｘ）２．７７を得た。0V compound () was dissolved in 30ml of ether, reduced by adding 0.37ml of Lindlar catalyst, filtered, and distilled off the ether to give 4-hydroxy-3-(3-methyl-2-butenyl)-4-0. -(1,1-dimethylallyl)benzaldehyde (X) 2.77% was obtained.
以上の様にして得た２．６７の化合物（Ｖ）と２．７ｙ
の化合物（Ｘ）を５０ｍ１のエタノールに溶かし、これ
に５０％苛性カリ水溶液３０ｍ１を加え３０−５０℃で
３時間撹拌する。４００ｍ１のエーテルで抽出し、エー
テルを留去して２ζ４・４′トリハイドロキシ−３−（
３−メチル−２−ブテニル）−４・ｌ−０−ビス−（１
・１−ジメチルアリル）カルコン（ＸＩ）３、１７を得
た。Compound (V) of 2.67 and 2.7y obtained as above
Compound (X) is dissolved in 50 ml of ethanol, 30 ml of 50% caustic potassium aqueous solution is added thereto, and the mixture is stirred at 30-50°C for 3 hours. Extract with 400ml of ether and distill off the ether to obtain 2ζ4.4'trihydroxy-3-(
3-methyl-2-butenyl)-4・l-0-bis-(1
-1-dimethylallyl)chalcone (XI) 3,17 was obtained.
３．１７の化合物（ＸＩ）を２０ｍ１のジエチルアニリ
ン中にて窒素気流下、１７０℃で５時間加熱した後、工
ーテルで抽出し、エーテル留去後の残留物をシリカゲル
カラムクロマトグラフイ一でヘキサン−アセトン混液で
分画し、２′・４・ｌ−トリハイドロキシ−３・３ξ５
−トリス（３−メチル−２−ブテニル）カルコン（１）
１．３ｙを得た。Compound (XI) of 3.17 was heated in 20 ml of diethylaniline at 170°C under a nitrogen stream for 5 hours, extracted with ether, and the residue after distilling off the ether was purified by silica gel column chromatography. Fractionated with hexane-acetone mixture, 2', 4, l-trihydroxy-3, 3ξ5
-tris(3-methyl-2-butenyl)chalcone (1)
Obtained 1.3y.
Ｍｐｌ６ｌ℃実施例 ２
２・４−ジハイドロキシ−３−（３−メチル−２−ブテ
ニル）アセトフエノンに実施例１と同様に２−クロロ−
２−メチル−３−ブチンを反応させた後還元して、２・
４−ジハイドロキシ−３−（３−メチル−２−ブテニル
）−４−０−（１・１−ジメチルアリル）アセトフエノ
ン（）を得た。Mpl6l℃Example 2 2-Chloro-
After reacting with 2-methyl-3-butyne, it is reduced to produce 2.
4-dihydroxy-3-(3-methyl-2-butenyl)-4-0-(1,1-dimethylallyl)acetophenone () was obtained.
次に、化合物（）３．１ｙと実施例１の化合物（Ｘ）２
．８ｙをエタノール５０ｍ１に溶かし、これに５０％苛
性カリ水溶液４０ｍ１を加え３０−５０℃で２時間攪拌
した後、室温で１日攪拌する。Next, compound ()3.1y and compound (X)2 of Example 1
．． 8y was dissolved in 50 ml of ethanol, 40 ml of 50% caustic potassium aqueous solution was added thereto, and the mixture was stirred at 30-50° C. for 2 hours and then at room temperature for 1 day.
エーテルで抽出し、エーテルを留去し２′・４・４′ト
リハイドロキシ−３・３′−ビス（３−メチル２−ブテ
ニル）−４・４′−０−ビス（１・１−ジメチルアリル
）カルコン（ＸＩｎ）を３．２ｙ得た。３．２７の化合
物（）にジエチルアニリンを２０ｍ１加え、窒素気流下
１５０℃で７時間加熱した後エーテル抽出し、エーテル
留去後、ヘキサン−アセトンで再結晶して２′・４・ｌ
−トリハイドロキシ−３・３ζ５・５′−テトラキズ−
（３−メチル−２−ブテニル）カルコン（１）２．１ｔ
を得た。Extraction with ether was carried out, and the ether was distilled off to give 2',4,4'trihydroxy-3,3'-bis(3-methyl-2-butenyl)-4,4'-0-bis(1,1-dimethylallyl). ) 3.2y of chalcone (XIn) was obtained. Add 20 ml of diethylaniline to the compound () of 3.27, heat it at 150°C for 7 hours under a nitrogen stream, extract it with ether, distill off the ether, and recrystallize with hexane-acetone to obtain 2'.4.l.
-Trihydroxy-3,3ζ5,5'-Tetra-wound-
(3-methyl-2-butenyl)chalcone (1) 2.1t
I got it.
Ｍｐｌ７５ニＣ実施例 ３
実施例２の化合物（）３．４７と実施例１の化合物（）
３．１７を７０ｍ１のエタノールに溶かし、これに５０
％苛性ソーダ水溶液２５ｍ１を加え４０６０℃にて２時
間攪拌し、冷後エーテルで抽出し、エーテルを留去して
、２′・４・４′一トリハイドロキシ一３′−（３−メ
チル−２−ブテニル）一４・４′−０−（１・１−ジメ
チルアリル）カルコン（ＸＩＶ）３．０７を得た。Mpl75niC Example 3 Compound of Example 2 () 3.47 and Compound of Example 1 ()
Dissolve 3.17 in 70ml of ethanol and add 50ml of
% caustic soda aqueous solution was added and stirred at 4060°C for 2 hours. After cooling, the mixture was extracted with ether and the ether was distilled off. 3.07 of 4,4'-0-(1,1-dimethylallyl)chalcone (XIV) was obtained.
３．０７の化合物（ＸＩＶ）を２４ｍ１のジエチルアニ
リンに溶かし、窒素気流下２００℃、１時間加熱した後
、エーテルで抽出し、エーテル留去後の油状物をシリカ
ゲルクロマトグラフイ一にて分画すると２′・４・４′
一トリハイドロキシ一３・３′・５′一トリス一（３−
メチル−２ブテニル）カルコン（１）１．８ｙを得た。Compound (XIV) of 3.07 was dissolved in 24 ml of diethylaniline, heated at 200°C for 1 hour under a nitrogen stream, extracted with ether, and the oily substance after distilling off the ether was fractionated using silica gel chromatography. Then 2', 4, 4'
- Trihydroxy - 3, 3', 5' - Tris - (3-
1.8y of methyl-2-butenyl)chalcone (1) was obtained.
Ｍｐｌ５９℃実施例 ４
実施例１の化合物（Ｖ）５．１７と化合物（）４．９７
をエタノール１００ｍ１に溶かし、これに５０％苛性カ
リ水溶液を加え、４０−６０℃で２時間撹拌し、室温に
１４時間放置後、再び４０一５０℃で１時間攪拌する。Mpl59℃ Example 4 Compound (V) of Example 1 5.17 and Compound () 4.97
was dissolved in 100 ml of ethanol, 50% caustic potassium aqueous solution was added thereto, stirred at 40-60°C for 2 hours, left at room temperature for 14 hours, and stirred again at 40-50°C for 1 hour.
冷後、エーテル抽出し、エーテルを留去し２′・４・４
′一トリハイドロキシ４・ｌ−０−ビス−（１・１−ジ
メチルアリル）カルコン（ＸＶ）を５．７ｙ得た。５．
７ｔの化合物（ＸＶ）を４０ｍ１のジエチルアニリン中
にて１１０℃で８時間加熱した後、エーテル抽出し、エ
ーテル留去後の油状物をシリカゲルカラムマトグラフイ
一に供して２′・４・４′一トリハイドロキシ一３・３
′−ビス−（３−メチル−２−ブテニル）カルコン（Ｉ
）２．９ｇを得た。After cooling, extract with ether and distill off the ether to give 2', 4, 4
5.7y of '-trihydroxy 4.l-0-bis-(1.1-dimethylallyl)chalcone (XV) was obtained. 5.
After heating 7t of compound (XV) in 40ml of diethylaniline at 110°C for 8 hours, it was extracted with ether, and the oil after distilling off the ether was subjected to silica gel column chromatography to obtain 2', 4, and 4' 1-trihydroxy-3.3
'-bis-(3-methyl-2-butenyl)chalcone (I
) 2.9g was obtained.
Claims (1)
ル−２−ブテニル基を示す。 〕で表わされるイソプレニルカルコン類を合成するに当
り、一般式 ▲数式、化学式、表等があります▼ 〔式中、Ｒ＾３は前記Ｒ＾１が水素原子のとき水素原子
であり、前記Ｒ＾１が３−メチル−２−ブテニル基のと
き３−メチル−２−ブテニル基である。 Ｒ＾４は前記Ｒ＾２が水素原子のとき水素原子であり、
前記Ｒ＾２が３−メチル−２−ブテニル基のとき３−メ
チル−２−ブテニル基である。〕で表わされる化合物を
加熱し、転位させることを特徴とするイソプレニルカル
コン類の合成法。 ：[Claims] 1 General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, R^1 and R^2 represent a hydrogen atom or a 3-methyl-2-butenyl group. ] In synthesizing isoprenyl chalcone represented by the general formula ▲ mathematical formula, chemical formula, table, etc. ▼ [In the formula, R^3 is a hydrogen atom when R^1 is a hydrogen atom, and When ^1 is a 3-methyl-2-butenyl group, it is a 3-methyl-2-butenyl group. R^4 is a hydrogen atom when the above R^2 is a hydrogen atom,
When the above R^2 is a 3-methyl-2-butenyl group, it is a 3-methyl-2-butenyl group. A method for synthesizing isoprenyl chalcone compounds, which comprises heating and rearranging a compound represented by the following. :
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP48074075A JPS593459B2 (en) | 1973-06-30 | 1973-06-30 | Isoprenyl chalcone Ruino Goseihou |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP48074075A JPS593459B2 (en) | 1973-06-30 | 1973-06-30 | Isoprenyl chalcone Ruino Goseihou |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5024258A JPS5024258A (en) | 1975-03-15 |
| JPS593459B2 true JPS593459B2 (en) | 1984-01-24 |
Family
ID=13536678
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP48074075A Expired JPS593459B2 (en) | 1973-06-30 | 1973-06-30 | Isoprenyl chalcone Ruino Goseihou |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS593459B2 (en) |
-
1973
- 1973-06-30 JP JP48074075A patent/JPS593459B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5024258A (en) | 1975-03-15 |
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