JPS626686B2 - - Google Patents
Info
- Publication number
- JPS626686B2 JPS626686B2 JP55007612A JP761280A JPS626686B2 JP S626686 B2 JPS626686 B2 JP S626686B2 JP 55007612 A JP55007612 A JP 55007612A JP 761280 A JP761280 A JP 761280A JP S626686 B2 JPS626686 B2 JP S626686B2
- Authority
- JP
- Japan
- Prior art keywords
- tobacco extract
- unsaponifiable
- present
- solanesol
- mixture
- 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.)
- Expired
Links
- 241000208125 Nicotiana Species 0.000 claims description 16
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 239000010410 layer Substances 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- AFPLNGZPBSKHHQ-UHFFFAOYSA-N Betulaprenol 9 Natural products CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCO AFPLNGZPBSKHHQ-UHFFFAOYSA-N 0.000 description 9
- AFPLNGZPBSKHHQ-MEGGAXOGSA-N solanesol Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CO AFPLNGZPBSKHHQ-MEGGAXOGSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- FHKPLLOSJHHKNU-INIZCTEOSA-N [(3S)-3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(oxan-4-yl)methanone Chemical compound C(C)N1N=CC(=C1C)C=1N(C2=NC=NC(=C2N=1)O[C@@H]1CN(CC1)C(=O)C1CCOCC1)C FHKPLLOSJHHKNU-INIZCTEOSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- ACTIUHUUMQJHFO-UPTCCGCDSA-N coenzyme Q10 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UPTCCGCDSA-N 0.000 description 1
- 235000017471 coenzyme Q10 Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- DKHGMERMDICWDU-GHDNBGIDSA-N menaquinone-4 Chemical compound C1=CC=C2C(=O)C(C/C=C(C)/CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)=C(C)C(=O)C2=C1 DKHGMERMDICWDU-GHDNBGIDSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000011728 vitamin K2 Substances 0.000 description 1
Description
【発明の詳細な説明】
本発明は、ソラネソールを含有するタバコエキ
ス不けん化物の取得方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for obtaining an unsaponifiable tobacco extract containing solanesol.
タバコエキス不けん化物は、医薬として有用な
補酵素Ｑ、ビタミンK2の側鎖成分を合成する必
須中間体であり、かつそれ自体も医薬などに有用
なソラネソールを含有している。 Unsaponifiable tobacco extract is an essential intermediate for synthesizing the side chain components of coenzyme Q and vitamin K2 , which are useful as medicines, and also contains solanesol, which is itself useful in medicines.
従来、このタバコエキス不けん化物を取得する
には、タバコの葉を有機溶媒で抽出し、得られた
タバコエキスをけん化して、このけん化混合物を
ヘキサン、エーテルなどの有機溶媒と水とで分配
して、有機溶媒層を濃縮することによりなされて
いる。 Traditionally, to obtain this unsaponifiable tobacco extract, tobacco leaves are extracted with an organic solvent, the resulting tobacco extract is saponified, and the saponified mixture is partitioned between an organic solvent such as hexane or ether and water. This is done by concentrating the organic solvent layer.
しかしながら、この方法は引火性の高いヘキサ
ン、エーテルなどの有機溶媒を多量に用いるので
危険を伴うこと及び分配時の有機層と水層との層
分離性が悪く時間と手間が多くかかることなどの
欠点があり、必ずしも最良の方法とはいえなかつ
た。 However, this method is dangerous because it uses a large amount of highly flammable organic solvents such as hexane and ether, and it requires a lot of time and effort due to poor layer separation between the organic layer and the aqueous layer during distribution. It had its drawbacks and was not necessarily the best method.
本発明者らは、このような欠点のないタバコエ
キス不けん化物の取得方法を開発すべく鋭意研究
を重ねた結果、タバコエキス不けん化物が含水ア
ルコールには不溶であることを見いだし、この知
見に基づいて本発明をなすに至つた。 The inventors of the present invention have conducted intensive research to develop a method for obtaining unsaponifiable tobacco extract without these drawbacks, and have discovered that unsaponifiable tobacco extract is insoluble in hydroalcohol. The present invention was made based on this.
すなわち本発明は、タバコエキスけん化混合物
を含水アルコールで抽出し、含水アルコール可溶
物としてけん化物を除去し、不けん化物を残留物
として回収することを特徴とするタバコエキス不
けん化物の取得方法である。 That is, the present invention provides a method for obtaining unsaponifiable tobacco extract, which comprises extracting a saponified tobacco extract mixture with hydroalcohol, removing saponifiable substances as hydroalcohol-soluble substances, and recovering unsaponifiable substances as a residue. It is.
本発明で用いられるアルコールとしては炭素数
５以下のモノ又は多価アルコールが好ましく、特
に好ましい例としてはメタノール、エタノール、
イソプロパノールなどを挙げることができる。ま
たこれらのアルコールの含水率は30％以下が好ま
しい。 The alcohol used in the present invention is preferably a mono- or polyhydric alcohol having 5 or less carbon atoms, and particularly preferred examples include methanol, ethanol,
Examples include isopropanol. Further, the water content of these alcohols is preferably 30% or less.
抽出条件は、20〜150℃、好ましくは20〜100℃
の温度で、含水アルコールの使用量はタバコエキ
ス１重量部に対し１〜20容量部、好ましくは２〜
５容量部である。 Extraction conditions are 20-150℃, preferably 20-100℃
At a temperature of
5 volume parts.
抽出は回分式又は連続式で行なわれ、抽出液と
残留物の分離は静置分層あるいは遠心分離などの
方法で行われる。 Extraction is carried out batchwise or continuously, and the extract and residue are separated by a method such as static separation or centrifugation.
なお、タバコエキスのけん化は従来行われてい
るいかなる方法を用いてもよいが、抽出時に使用
するアルコールを溶媒として行うのが本発明方法
を実施するうえで有利である。 Although any conventional method may be used to saponify the tobacco extract, it is advantageous to carry out the method of the present invention by using the alcohol used during extraction as a solvent.
本発明のタバコエキス不けん化物の取得方法
は、引火性の高い有機溶媒を多量に使う必要がな
いばかりでなく、層分離をすみやかに行えるので
時間及び手間がかからず、工業的実施に適してい
る。 The method for obtaining unsaponifiable tobacco extract of the present invention not only does not require the use of large amounts of highly flammable organic solvents, but also allows for quick layer separation, which saves time and effort, making it suitable for industrial implementation. ing.
次に実施例により本発明をさらに詳細に説明す
る。 Next, the present invention will be explained in more detail with reference to Examples.
なお、各実施例中ソラネソールの分析は、シリ
カゲルカラムを用いた高速液体クロマトグラフイ
ーにより行つた。 In each example, solanesol was analyzed by high performance liquid chromatography using a silica gel column.
実施例 １
タバコエキス100ｇにカセイカリ10ｇ、メタノ
ール100ml及び水10ｇを加え60℃で３時間かきま
ぜてけん化を行つた。反応混合物を40℃まで冷却
し、含水メタノール（含水率1.0％）200mlを加
え、５分間かきまぜた後静置したところ２層に分
れた。上層部と下層部を分離し、それぞれについ
てソラネソールを分析したところ、全体の96％が
下層に存在していた。下層部は100ｇであり、濃
縮乾固したところ、ソラネソール18％を含む残留
物75ｇを得た。上層部は250ｇであり、けん化物
35ｇを含んでいた。Example 1 10 g of caustic potash, 100 ml of methanol and 10 g of water were added to 100 g of tobacco extract, and the mixture was stirred at 60° C. for 3 hours to perform saponification. The reaction mixture was cooled to 40° C., 200 ml of water-containing methanol (water content 1.0%) was added, stirred for 5 minutes, and left to stand to separate into two layers. When we separated the upper and lower layers and analyzed the solanesol in each, we found that 96% of the total was present in the lower layer. The lower layer weighed 100 g and was concentrated to dryness to obtain 75 g of a residue containing 18% solanesol. The upper layer is 250g and saponified
It contained 35g.
実施例 ２
タバコエキス100ｇにカセイソーダ８ｇ、エタ
ノール100ml及び水10ｇを加え70℃にて４時間か
きまぜてけん化を行つた。反応混合物に含水エタ
ノール（含水率20％）300mlを加え、60℃で５分
間かきまぜた後静置したところ２層に分層した。
上層部と下層部を分離し、それぞれについてソラ
ネソールを分析したところ、全体の94％が下層に
存在していた。上層部は400mlであつた。下層部
は120ｇであり、これを濃縮乾固したところソラ
ネソール19％を含む残留物70ｇを得た。Example 2 8 g of caustic soda, 100 ml of ethanol, and 10 g of water were added to 100 g of tobacco extract, and the mixture was stirred at 70° C. for 4 hours to perform saponification. 300 ml of aqueous ethanol (water content 20%) was added to the reaction mixture, stirred at 60°C for 5 minutes, and left to stand, resulting in separation into two layers.
When we separated the upper and lower layers and analyzed the solanesol in each, we found that 94% of the total was present in the lower layer. The upper layer was 400ml. The lower layer weighed 120 g and was concentrated to dryness to obtain 70 g of a residue containing 19% solanesol.
実施例 ３
タバコエキス100ｇにカセイカリ10ｇ及びメタ
ノール200mlを加え３時間60℃にてかきまぜてけ
ん化を行つた。反応混合物に水10mlを加え、30℃
で10分間かきまぜた後遠心効果1500の遠心分離機
で分離した。上層部と下層部を分離し、それぞれ
ソラネソールを分析したところ、全体の94％が下
層に存在していた。下層部は95ｇであり、濃縮乾
固したところ、ソラネソール20％を含む残留物67
ｇを得た。Example 3 10 g of caustic potash and 200 ml of methanol were added to 100 g of tobacco extract, and the mixture was stirred at 60° C. for 3 hours to perform saponification. Add 10ml of water to the reaction mixture and heat at 30°C.
After stirring for 10 minutes, the mixture was separated using a 1500 centrifuge centrifuge. When we separated the upper and lower layers and analyzed each solanesol, we found that 94% of the total was present in the lower layer. The lower layer weighed 95g, and when concentrated to dryness, a residue containing 20% solanesol was 67%.
I got g.
Claims (1)
で抽出し、含水アルコール可溶物としてけん化物
を除去し、不けん化物を残留物として回収するこ
とを特徴とするタバコエキス不けん化物の取得方
法。1. A method for obtaining an unsaponifiable substance from a tobacco extract, which comprises extracting a saponified tobacco extract mixture with a hydrous alcohol, removing the saponified substance as a hydrous alcohol-soluble substance, and recovering the unsaponifiable substance as a residue.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP761280A JPS56104820A (en) | 1980-01-25 | 1980-01-25 | Preparation of unsaponified tobacco extract |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP761280A JPS56104820A (en) | 1980-01-25 | 1980-01-25 | Preparation of unsaponified tobacco extract |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56104820A JPS56104820A (en) | 1981-08-20 |
| JPS626686B2 true JPS626686B2 (en) | 1987-02-13 |
Family
ID=11670625
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP761280A Granted JPS56104820A (en) | 1980-01-25 | 1980-01-25 | Preparation of unsaponified tobacco extract |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS56104820A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110353299A (en) * | 2019-06-29 | 2019-10-22 | 常德市正阳生物科技股份有限公司 | A kind of extracting method of leaf tobacco extract |
| CN110384249A (en) * | 2019-06-29 | 2019-10-29 | 常德市正阳生物科技股份有限公司 | A kind of raw material selection processing method for extracting Salanesol |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100410222C (en) * | 2006-02-13 | 2008-08-13 | 李祥庆 | Method for extracting high purity solanesol from low content solanesol extract |
| CN104086425B (en) * | 2014-07-30 | 2016-04-13 | 中国农业科学院烟草研究所 | A kind of method simultaneously extracting also separate tobacco chlorogenic acid, Salanesol, alkaloid, violaguercitrin |
-
1980
- 1980-01-25 JP JP761280A patent/JPS56104820A/en active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110353299A (en) * | 2019-06-29 | 2019-10-22 | 常德市正阳生物科技股份有限公司 | A kind of extracting method of leaf tobacco extract |
| CN110384249A (en) * | 2019-06-29 | 2019-10-29 | 常德市正阳生物科技股份有限公司 | A kind of raw material selection processing method for extracting Salanesol |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56104820A (en) | 1981-08-20 |
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