JPS63162647A - Production of 8,9-dihydronootkatone - Google Patents
Production of 8,9-dihydronootkatoneInfo
- Publication number
- JPS63162647A JPS63162647A JP30839586A JP30839586A JPS63162647A JP S63162647 A JPS63162647 A JP S63162647A JP 30839586 A JP30839586 A JP 30839586A JP 30839586 A JP30839586 A JP 30839586A JP S63162647 A JPS63162647 A JP S63162647A
- Authority
- JP
- Japan
- Prior art keywords
- nootkatone
- reaction
- chloranil
- didehydronotkatone
- oxidizing
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- WTOYNNBCKUYIKC-JMSVASOKSA-N (+)-nootkatone Chemical compound C1C[C@@H](C(C)=C)C[C@@]2(C)[C@H](C)CC(=O)C=C21 WTOYNNBCKUYIKC-JMSVASOKSA-N 0.000 claims abstract description 28
- WTOYNNBCKUYIKC-UHFFFAOYSA-N dl-nootkatone Natural products C1CC(C(C)=C)CC2(C)C(C)CC(=O)C=C21 WTOYNNBCKUYIKC-UHFFFAOYSA-N 0.000 claims abstract description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 15
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000011541 reaction mixture Substances 0.000 claims abstract description 6
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 230000001590 oxidative effect Effects 0.000 claims abstract description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000008096 xylene Substances 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 6
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 239000000796 flavoring agent Substances 0.000 abstract description 6
- 240000000560 Citrus x paradisi Species 0.000 abstract description 5
- 235000019634 flavors Nutrition 0.000 abstract description 5
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 235000013305 food Nutrition 0.000 abstract 1
- 235000013599 spices Nutrition 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000006227 byproduct Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- NIIPDXITZPFFTE-ABAIWWIYSA-N alpha-Vetivone Chemical compound C1CC(=C(C)C)C[C@@]2(C)[C@H](C)CC(=O)C=C21 NIIPDXITZPFFTE-ABAIWWIYSA-N 0.000 description 3
- NIIPDXITZPFFTE-NHYWBVRUSA-N alpha-vetivone Natural products O=C1C=C2[C@](C)([C@@H](C)C1)C/C(=C(/C)\C)/CC2 NIIPDXITZPFFTE-NHYWBVRUSA-N 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- PHRADXUJOZKVDN-JMSVASOKSA-N (4r,4as,6s)-4,4a-dimethyl-6-prop-1-en-2-yl-3,4,5,6-tetrahydronaphthalen-2-one Chemical compound C1=C[C@@H](C(C)=C)C[C@@]2(C)[C@H](C)CC(=O)C=C21 PHRADXUJOZKVDN-JMSVASOKSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 240000008866 Ziziphus nummularia Species 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分デ］
本発明は８，９−ジデヒドロヌートカトンの改良された
！１３２を方法に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Applications] The present invention provides improved 8,9-didehydronotkatone! 132 relating to methods.
本発明によって得られる８、９−ジデヒドロヌートカト
ンはヌートカトンとともにグレープフルーツの特徴ある
香味の一部をなし、食品香料として有用であり、さらに
香粧品香料としての用途も期待されている。8,9-didehydronotkatone obtained by the present invention forms part of the characteristic flavor of grapefruit together with nootkatone, and is useful as a food flavoring agent, and is also expected to be used as a cosmetic flavoring agent.
し従来の技術およびその問題点］
８．９−ジデヒドロヌートカトンはグレープフルーツの
香味成分の１つとして得られるが天然物中には微量しか
含まれていないので工業的に得るためには合成によらな
ければならない。８．９−ジデヒドロヌートカトンの合
成法としてヌートカトンを酢酸中クロラニルで酸化する
方法がテトラヘドロン レターズ（Ｔｅｔｒａｈｅｄｒ
ｏｎ Ｌｅｔｔｅｒｓ）第５２巻４７７９頁（１９６
５年）に記載されている。この文献には収率が記載され
ておらず、本発明者が追試しなところ、８．９−ジデヒ
ドロヌートカトンの異性体である８、９−ジデヒドロ−
α−ベチボンが副生じ、目的物の収率は５０％以下であ
った。さらに副生じた８、９−ジデヒドロ−α−ベチボ
ンはベチベリルアセテート様の匂いをもち、しかもカラ
ムクロマトグラフィーや蒸留等の精製手段でも８．９−
ジデヒドロヌートカトンとの分離が困難である。従って
上記従来法において得られる生成物は８．９−ジデヒド
ロヌートカトンと ８．９−ジデしドローα−ベチボン
の混合物であり、このものはグレープフルーツ様の匂い
が全くない。8.9-Didehydronotkatone is obtained as one of the flavor components of grapefruit, but since it is only contained in trace amounts in natural products, it is difficult to synthesize it to obtain it industrially. I have to rely on it. 8. A method for synthesizing nootkatone, oxidizing nootkatone with chloranil in acetic acid, was published in Tetrahedron Letters.
on Letters) Volume 52, page 4779 (196
5 years). This document does not describe the yield, and the inventor of the present invention conducted additional tests and found that 8,9-didehydro-, which is an isomer of 8,9-didehydronotkatone.
α-vetivone was produced as a by-product, and the yield of the target product was less than 50%. Furthermore, the by-produced 8,9-didehydro-α-vetivone has a vetivery acetate-like odor, and even when purifying means such as column chromatography or distillation, the 8,9-didehydro-α-vetivone
Difficult to separate from didehydronotkatone. Therefore, the product obtained in the above conventional method is a mixture of 8,9-didehydronotkatone and 8,9-didehydronotkatone, which has no grapefruit-like odor at all.
ヌートカトン ８．９−ジデヒドロ
８．９−ジデヒドローヌートカトン
α−ベチボン［問題点を解決するための手段］
本発明は８，９−ジデヒドロ−α−ベチボンを全く副生
ずることなく、ヌートカトンから収率よく８．９−ジデ
ヒドロヌートカトンを製造する方法を提供することを目
的とするものであり、かかる目的は下記の方法によって
達成される。Nootkatone 8.9-didehydro
8.9-didehydroneotkatone
α-vetivone [Means for solving the problem] The present invention provides a method for producing 8,9-didehydro nootkatone from nootkatone in a high yield without producing any by-product of 8,9-didehydro-α-vetivone. This objective is achieved by the following method.
１）ヌートカトンをクロラニルで酸化して８．９−ジデ
ヒドロヌートカトンを製造する方法において、上記反応
を非極性非プロトン有機溶媒の存在下、クロラニルをヌ
ートカトンに対して１〜１．５モル当量使用して行ない
、未反応のヌートカトンが反応混合物中に約２０％残存
する状態で反応を停止させることを特徴とする８、９−
ジデヒドロヌートカトンの製法。1) In a method for producing 8.9-didehydronotkatone by oxidizing nootkatone with chloranil, the above reaction is carried out in the presence of a non-polar aprotic organic solvent, using 1 to 1.5 molar equivalents of chloranil to nootkatone. 8,9- characterized in that the reaction is stopped in a state where about 20% of unreacted nootkatone remains in the reaction mixture.
Process for producing didehydronotkatone.
２）溶媒がトルエン、キシレン、ベンゼン、ヘキサンま
たはヘプタンである第１項記載の製法。2) The method according to item 1, wherein the solvent is toluene, xylene, benzene, hexane or heptane.
［発明の詳細な説明］
本発明の方法はヌートカトンを前記溶媒に溶解し、該溶
液にクロラニルを加え、７０〜９０℃に加熱することに
よって容易に実施される。DETAILED DESCRIPTION OF THE INVENTION The method of the present invention is easily carried out by dissolving nootkatone in the above solvent, adding chloranil to the solution and heating to 70-90°C.
クロラニルの使用量はヌートカトンに対して１〜１．５
モル当量であることを要し、それ以上の量を使用すると
８．９−ジデヒドロ−α・ベチボンが副生ずる。The amount of chloranil used is 1 to 1.5 to nootkatone.
The molar equivalent is required, and if a larger amount is used, 8.9-didehydro-α.vetivone will be produced as a by-product.
溶媒としてはトルエン、キシレン、ベンゼン、ヘキサン
、ヘプタンのような非極性でかつ非プロトン溶媒を使用
することが必要である。酢酸、酢酸エチルあるいはｔ−
ブタノール等を使用すると上記ベチボンが副生ずる。As the solvent, it is necessary to use a non-polar and aprotic solvent such as toluene, xylene, benzene, hexane, heptane. Acetic acid, ethyl acetate or t-
When butanol or the like is used, the vetibone mentioned above is produced as a by-product.
本発明方法においては、原料ヌートカトンが約２０％残
存混合物中に残存する時点で反応を停止させることが必
要であり原料が消失するまで反応を進行させると上記ベ
チボンが副生ずる０反応温度は約７０〜９０℃が適当で
あり、反応時間はおよそ３０分間ないし３時間である０
反応終了後所望の生成物は常法に従って、反応混合物か
ら採取される。In the method of the present invention, it is necessary to stop the reaction when about 20% of the starting material nootkatone remains in the mixture.If the reaction is allowed to proceed until the starting material disappears, the above-mentioned vetibone is produced as a by-product.The reaction temperature is about 70°C. ~90°C is suitable, and the reaction time is approximately 30 minutes to 3 hours.
After the reaction is complete, the desired product is recovered from the reaction mixture according to conventional methods.
例えば反応混合物を放冷し、不溶物をろ去し、ろ液を適
当な有機溶媒例えば塩化メチレン、トルエン、ベンゼン
等で抽出し、抽出液から溶媒を留去し、残留物をカラム
クロマトグラフィーで手早く精製する。蒸留すると所望
の８，９−ジデヒドロヌートカトンが熱により容易に異
性化して上記ベチボンを生成するので好ましくない、か
くして得られた生成物はヌートカトンと８，９−ジデヒ
ドロヌートカトンの混合物であるが再化合物ともグレー
プフルーツの香味成分の１つとして使用されるのでこれ
らを分離することを要しない。For example, the reaction mixture is allowed to cool, insoluble matters are removed by filtration, the filtrate is extracted with a suitable organic solvent such as methylene chloride, toluene, benzene, etc., the solvent is distilled off from the extract, and the residue is subjected to column chromatography. Refine quickly. Distillation is undesirable because the desired 8,9-didehydronotkatone is easily isomerized by heat to form vetibone, and the product thus obtained is a mixture of nootkatone and 8,9-didehydronotkatone. Since both the recombinant compound and the recombinant compound are used as one of the flavor components of grapefruit, it is not necessary to separate them.
８．９−ジデヒドロヌートカトンは極めて不安定であり
、−１０℃の低温に保持しても１２時間で約２０％が８
，９−ジデヒドロ−α−ベチボンに異性化するが、アル
コール、プロピレングリコール等で希釈して冷暗所に保
存することにより上記異性化を防止することができる。8.9-Didehydronotkatone is extremely unstable, and even when kept at a low temperature of -10°C, approximately 20% of it is converted to 8 in 12 hours.
, 9-didehydro-α-vetivone, but the above-mentioned isomerization can be prevented by diluting with alcohol, propylene glycol, etc. and storing in a cool, dark place.
８．９−ジデヒドロヌートカトンは軽く拡散性があり、
グレープフルーツの香味の特徴の１パートを表現し、ヌ
ートカトンより匂いは強い。8.9-Didehydronotkatone is light and diffusible;
It expresses part of the flavor characteristics of grapefruit, and has a stronger odor than Nootkatone.
次に実施例および比較例を示して本発明をさらに具体的
に説明する。Next, the present invention will be explained in more detail with reference to Examples and Comparative Examples.
実施例 １
ヌートカトン１２．、トルエンｇｏ、、、およびクロラ
ニル１４ｇの混合物を９０℃にて加熱攪拌しな、温度上
昇につれて、不溶物は溶解してくる。約１時間後、沈殿
が生成してくるところで、反応を停止した０反応液を放
冷後、不溶物をろ過し、沈殿をトルエンを用いて数回洗
浄した。ろ液を水洗した後、無水ｉｔ＠ナトリウムで乾
燥した後、トルエンを留去して得られた粗油を手早くカ
ラムクロマトグラフィーで精製し、８．９−ジデヒド口
ヌートカトンとヌートカトンの混合物が３．５ｇ （比
率＝４：１）得られた。Example 1 Nootkatone12. A mixture of , toluene go, , and 14 g of chloranil is heated and stirred at 90° C. As the temperature rises, insoluble matter dissolves. After about 1 hour, when a precipitate started to form, the 0 reaction solution, which had stopped the reaction, was allowed to cool, the insoluble matter was filtered, and the precipitate was washed several times with toluene. After washing the filtrate with water and drying it over anhydrous sodium, toluene was distilled off and the resulting crude oil was quickly purified by column chromatography to obtain a mixture of 8.9-didehyde nootkatone and nootkatone. 5 g (ratio=4:1) was obtained.
実施例 ２
ヌートカトン６ｇ、ベンゼン４０［ｒ、およびクロラニ
ル５．３ｇの混合物を８０℃にて加熱攪拌した。Example 2 A mixture of 6 g of nootkatone, 40 [r] of benzene, and 5.3 g of chloranil was heated and stirred at 80°C.
約１．５時間後、沈殿が生成してくるところで反応を停
止した０反応液を放冷後不溶物をろ過し、沈殿をベンゼ
ンを用いて数回洗浄した。After about 1.5 hours, the reaction was stopped at the point where a precipitate was formed. The reaction solution was left to cool, and insoluble matter was filtered, and the precipitate was washed several times with benzene.
実施例２と同様に後処理すると、８．９−ジデヒドロヌ
ートカトンとヌートカトンの混合物１．６ｇ（比率４：
１）が得られた。After treatment as in Example 2, 1.6 g of a mixture of 8.9-didehydronotkatone and nootkatone (ratio 4:
1) was obtained.
比較例
種々の溶媒を用いて実施例１と同様にしてヌートカトン
をクロラニルで酸化し、８，９−ジデヒドロヌートカト
ンおよび８．９−ジブしドローα−ベチボンの生成比（
％）を測定した。結果を表１に示す。Comparative Example Nootkatone was oxidized with chloranil in the same manner as in Example 1 using various solvents, and the production ratio of 8,9-didehydronotkatone and 8,9-dib-draw α-vetivone (
%) was measured. The results are shown in Table 1.
（以下余白）
表 １
反応物の生成比（％）
上記表１から明らかなように、溶媒として酢酸またはｔ
−ブタノールを使用した場合は原料を２０％以上残存さ
せても８．９−ジデヒドロヌートカトンの他に８．９−
ジデヒドロ−α−ベチボンが相当棗副生し、また酢酸エ
チルを使用した場合は８．９−ジデヒドロヌートカトン
は全く生成せず、上記ベチボンのみが生成する。これに
対して溶媒としてトルエンまたはヘキサンを使用し、原
料ヌートカトンを２０％以上残存させた場合には上記ベ
チボンは全く副生じない。(Left below) Table 1 Production ratio of reactants (%) As is clear from Table 1 above, acetic acid or t as a solvent
- When butanol is used, even if more than 20% of the raw material remains, in addition to 8.9-didehydronotkatone, 8.9-
A considerable amount of didehydro-α-vetivone is produced as a by-product of jujube, and when ethyl acetate is used, 8,9-didehydronotkatone is not produced at all, and only the vetibone is produced. On the other hand, when toluene or hexane is used as a solvent and 20% or more of the raw material nootkatone remains, vetibone is not produced as a by-product at all.
Claims (1)
ヒドロヌートカトンを製造する方法において、上記反応
を非極性非プロトン有機溶媒の存在下、クロラニルをヌ
ートカトンに対して１〜１．５モル当量使用して行ない
、未反応のヌートカトンが反応混合物中に約２０％残存
する状態で反応を停止させることを特徴とする８，９−
ジデヒドロヌートカトンの製法。 ２）溶媒がトルエン、キシレン、ベンゼン、ヘキサンま
たはヘプタンである特許請求の範囲第１項記載の製法。[Scope of Claims] 1) A method for producing 8,9-didehydronotkatone by oxidizing nootkatone with chloranil, in which the above reaction is carried out in the presence of a non-polar aprotic organic solvent in which chloranil is oxidized to nootkatone at 8,9- characterized in that the reaction is carried out using 1.5 molar equivalents and the reaction is stopped in a state where about 20% of unreacted nootkatone remains in the reaction mixture.
Process for producing didehydronotkatone. 2) The method according to claim 1, wherein the solvent is toluene, xylene, benzene, hexane or heptane.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30839586A JPS63162647A (en) | 1986-12-26 | 1986-12-26 | Production of 8,9-dihydronootkatone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30839586A JPS63162647A (en) | 1986-12-26 | 1986-12-26 | Production of 8,9-dihydronootkatone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63162647A true JPS63162647A (en) | 1988-07-06 |
Family
ID=17980546
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP30839586A Pending JPS63162647A (en) | 1986-12-26 | 1986-12-26 | Production of 8,9-dihydronootkatone |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63162647A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2017012004A (en) * | 2015-06-26 | 2017-01-19 | サントリー食品インターナショナル株式会社 | Sodium-containing carbonic acid beverage |
-
1986
- 1986-12-26 JP JP30839586A patent/JPS63162647A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2017012004A (en) * | 2015-06-26 | 2017-01-19 | サントリー食品インターナショナル株式会社 | Sodium-containing carbonic acid beverage |
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