JP2935055B2 - Extraction and separation method of natural jasminic acid - Google Patents
Extraction and separation method of natural jasminic acidInfo
- Publication number
- JP2935055B2 JP2935055B2 JP2120556A JP12055690A JP2935055B2 JP 2935055 B2 JP2935055 B2 JP 2935055B2 JP 2120556 A JP2120556 A JP 2120556A JP 12055690 A JP12055690 A JP 12055690A JP 2935055 B2 JP2935055 B2 JP 2935055B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- natural
- jasminic
- extraction
- ethyl acetate
- 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 - Lifetime
Links
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- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
【発明の詳細な説明】 産業上の利用分野 本発明は、天然ジャスミン酸の抽出分離方法に関す
る。The present invention relates to a method for extracting and separating natural jasminic acid.
従来技術およびその問題点 天然ジャスミン酸は、ソケイ、マツリカなどの高等植
物に存在し、植物ホルモン様物質として植物成長調節作
用などの作用を有することがわかっている（上田、加
藤、植物の化学調節、15（２）、1980）。従って、天然
ジャスミン酸は、果実の収穫の改善、耐公害性の向上な
どに利用され得る。また天然ジャスミン酸は、化粧品の
香料、食料品の香料などとしても有用である。Prior art and its problems Natural jasminic acid is known to exist in higher plants such as Sokai and Matsurika and has plant growth-regulating effects as plant hormone-like substances (Ueda, Kato, Chemical regulation of plants). , 15 (2), 1980). Therefore, natural jasminic acid can be used for improving fruit harvest, improving pollution resistance, and the like. Natural jasminic acid is also useful as a fragrance for cosmetics, a fragrance for foodstuffs, and the like.
従来、天然ジャスミン酸の植物からの分離は、まず低
級アルコールで抽出した後、溶媒を留去し、得られた水
相のpHを調整し、酢酸エチルなどの有機溶媒を多種類用
いて、抽出操作を繰り返し行なうことにより実施されて
いる。しかしながら、この方法は、多段階の操作を必要
とし、抽出後長時間に亘って低温下に溶媒を留去させる
必要がある。また、有機溶媒は、皮膚組織破壊、気管支
障害、癌原性などの有機溶媒の有害作用を取扱者にもた
らす可能性があり、また容器から洩れ易く、引火し易い
という欠点を持つ。従って、大量の有機溶媒を必要とす
る従来の抽出操作を安全に実施するには、基準濃度の溶
媒を用い、管理された場所で実施する必要がある。Conventionally, natural jasminic acid is separated from plants by first extracting it with a lower alcohol, then distilling off the solvent, adjusting the pH of the resulting aqueous phase, and using a variety of organic solvents such as ethyl acetate. It is implemented by repeating the operation. However, this method requires a multi-step operation, and it is necessary to distill off the solvent at a low temperature for a long time after the extraction. Further, the organic solvent has a drawback that it may cause harmful effects of the organic solvent such as destruction of skin tissue, bronchial disorder, carcinogenicity to the operator, and it is easily leaked from the container and easily flammable. Therefore, in order to safely perform a conventional extraction operation requiring a large amount of an organic solvent, it is necessary to perform the extraction in a controlled place using a solvent having a reference concentration.
問題点を解決するための手段 上記のような現状に鑑みて、本発明者は、天然ジャス
ミン酸を低コストで安全に容易に分離できる方法を研究
した結果、ジャスミン酸を含有する天然原料を低級アル
コールに懸濁させ、この懸濁液に水蒸気を吹き込むこと
により、上記のような問題を解決し得ることがわかっ
た。Means for Solving the Problems In view of the current situation as described above, the present inventor has studied a method capable of easily and safely separating natural jasminic acid at low cost, and as a result, the natural raw material containing jasminic acid has been reduced to a lower grade. It has been found that the above-mentioned problem can be solved by suspending the suspension in alcohol and blowing steam into the suspension.
即ち、本発明は、「天然ジャスミン酸を含有する植物
原料および／または微生物を90％（v/v）以上の１〜４
低級アルコールに懸濁させ、水蒸気を吹き込むことを特
徴とする天然ジャスミン酸の抽出分離方法」を提供す
る。That is, the present invention is, 90% of plant material and / or microorganisms containing "natural jasmine acid (v / v) or more 1-4
A method for extracting and separating natural jasminic acid, characterized by suspending in lower alcohol and blowing steam.
本発明において使用する天然ジャスミン酸を含有する
原料としては、ジャスミン酸を含有する全ての生体を利
用することができ、例えば、ニガヨモギ、ソケイ、マツ
リカなどの高等植物、ユーグレナ、スピルリナ、クロレ
ラなどの微生物を利用することができる。As a raw material containing natural jasminic acid used in the present invention, any living body containing jasminic acid can be used, for example, higher plants such as sagebrush, sorghum, and pine spores, microorganisms such as euglena, spirulina, and chlorella. Can be used.
本発明において、天然ジャスミン酸原料は、単独でま
たは異なる種類のものを組合わせて、乾燥状態または湿
潤状態で、90％（v/v）以上のＣ１〜４低級アルコール
中に懸濁させ、pH2〜４に調整して、最終アルコール濃
度70％以下になるまで、水蒸気を連続的に吹き込む。引
き続き、水蒸気に代えて窒素ガスなどの不活性ガスを吹
き込み、容器中に残留するエタノールを留去させる。そ
の後、残留水分を凍結乾燥により除去して、ジャスミン
酸を含有する粘性物質を得る。In the present invention, the natural jasminic acid raw material, alone or in combination of different types, is suspended in a dry or wet state in 90% (v / v) or more C 1-4 lower alcohols, The pH is adjusted to 2 to 4 and steam is continuously blown until the final alcohol concentration becomes 70% or less. Subsequently, an inert gas such as a nitrogen gas is blown in instead of the steam, and ethanol remaining in the container is distilled off. Thereafter, residual moisture is removed by freeze-drying to obtain a viscous substance containing jasminic acid.
次いでこの粘性物質を精製する。精製方法は、特に限
定されるものではないが、例えば、粘性物質を極微量の
酢酸エチル液に溶解させて、0.5Mギ酸を固定相とするシ
リカゲル分配カラムクロマトグラフィーに供する。0.5M
ギ酸を飽和させたｎ−ヘキサン／酢酸エチルの混合物を
移動相として溶離し、得られた１％酢酸エチル（99％ｎ
−ヘキサン）分画を濃縮する。得られたガム状残渣をシ
リカゲル薄層クロマトグラフィーに供し、ｎ−ヘキサン
／酢酸エチル／酢酸（10:2:1,v/v/v）で15cm展開して、
風乾させる。Rf 0.2〜0.6の展開部分を酢酸エチルで溶
出させた後、大量のジアゾメタンでメチル化し、分取ガ
スクロマトグラフィーに供して、ジャスミン酸メチルエ
ステルを得る。このようにして得られたジャスミン酸エ
ステルをアルカリにより加水分解して、ジャスミン酸を
得る。The viscous material is then purified. The purification method is not particularly limited. For example, a viscous substance is dissolved in a very small amount of ethyl acetate solution and subjected to silica gel partition column chromatography using 0.5 M formic acid as a stationary phase. 0.5M
A mixture of n-hexane / ethyl acetate saturated with formic acid was eluted as mobile phase and the resulting 1% ethyl acetate (99% n
-Hexane) fractions are concentrated. The resulting gummy residue was subjected to silica gel thin layer chromatography, developed with n-hexane / ethyl acetate / acetic acid (10: 2: 1, v / v / v) for 15 cm,
Allow to air dry. After eluting the developed part with Rf of 0.2 to 0.6 with ethyl acetate, it is methylated with a large amount of diazomethane and subjected to preparative gas chromatography to obtain jasminic acid methyl ester. The jasminic acid ester thus obtained is hydrolyzed with an alkali to obtain jasminic acid.
発明の効果 本発明の方法によれば、従来の抽出分離方法のような
複雑な工程を繰り返す必要がないため、分離作業が著し
く簡単になって、作業時間を従来方法の約1/4に短縮さ
れ、低コストで作業することができる。また、有機溶媒
を大量に使用する必要がないため、極めて安全に作業を
実施することができる。Effect of the Invention According to the method of the present invention, there is no need to repeat complicated steps as in the conventional extraction / separation method, so the separation operation is significantly simplified, and the operation time is reduced to about 1/4 of the conventional method. And can work at low cost. Further, since it is not necessary to use a large amount of the organic solvent, the operation can be performed extremely safely.
実施例 下記に実施例を挙げて、本発明を更に具体的に説明す
るが、本発明はこれに限定されるものではない。Examples Hereinafter, the present invention will be described more specifically with reference to Examples, but the present invention is not limited thereto.
実施例１ ニガヨモギ（キク科）の乾燥物の茎葉10kgを粉砕し、
95％エタノール水溶液中に懸濁させ、塩酸によりpH3に
調整した。該懸濁液中に、水蒸気（100℃）を約２時間
導入し、約60％エタノール水になった時点で、水蒸気に
代えて窒素ガス（40℃）を吹き込み、エタノールをほぼ
全量回収した。その後、残渣を凍結乾燥させて、残留水
分を除去して、粘性物質を得た。Example 1 10 kg of foliage of a dried product of sagebrush (Asteraceae) was crushed,
It was suspended in a 95% aqueous ethanol solution and adjusted to pH 3 with hydrochloric acid. Steam (100 ° C.) was introduced into the suspension for about 2 hours, and when it became about 60% ethanol water, nitrogen gas (40 ° C.) was blown in instead of steam to recover almost all ethanol. Thereafter, the residue was freeze-dried to remove residual moisture, and a viscous substance was obtained.
この粘性物質をシリカゲル分配カラムクロマトグラフ
ィー（シリカゲル（ワコーゲルC100、和光純薬製）150
g、カラム：直径1.1cm×長さ35cm、固定相:0.5Mギ酸、
移動相:n−ヘキサン／酢酸エチル混合溶媒）に供して、
１％酢酸エチル分画を得た。該分画を減圧濃縮して、ガ
ム状物質を得た。これをシリカゲル薄層クロマトグラフ
ィー（シリカゲルF254（メルク社製）0.3mm厚さ、30×2
0cm、ｎ−ヘキサン／酢酸エチル／酢酸（10:2:1,v/v/
v）で15cm展開）にかけて、Rf 0.34〜0.45の展開部分を
酢酸エチルで溶出した後、ただちに大過剰のジアゾメタ
ンのエーテル溶液でメチル化した。次いで、メチル化し
たものを分取ガスクロマトグラフィー（日立163型、カ
ラム:1％OV−１（直径3mm×長さ2m）ガラス、カラム温
度:160℃、キャリアーガス：窒素、流量:35ml/分）にか
けて、リテンションタイム6.3分の溶出部分を分取し
た。分取したジャスミン酸メチルエステルを1N水酸化ナ
トリウムで加水分解して，ジャスミン酸21ngを得た。This viscous substance is subjected to silica gel partition column chromatography (silica gel (Wakogel C100, Wako Pure Chemical Industries) 150
g, column: 1.1 cm diameter x 35 cm length, stationary phase: 0.5 M formic acid,
Mobile phase: n-hexane / ethyl acetate mixed solvent)
A 1% ethyl acetate fraction was obtained. The fraction was concentrated under reduced pressure to obtain a gum. This was subjected to silica gel thin layer chromatography (silica gel F254 (manufactured by Merck), 0.3 mm thick, 30 × 2
0 cm, n-hexane / ethyl acetate / acetic acid (10: 2: 1, v / v /
After developing with Rf 0.34 to 0.45, the residue was eluted with ethyl acetate and immediately methylated with a large excess of an ether solution of diazomethane. Subsequently, the methylated product was subjected to preparative gas chromatography (Hitachi 163 type, column: 1% OV-1 (diameter 3 mm x length 2 m) glass, column temperature: 160 ° C, carrier gas: nitrogen, flow rate: 35 ml / min) ), An eluted portion with a retention time of 6.3 minutes was collected. The separated jasminic acid methyl ester was hydrolyzed with 1N sodium hydroxide to obtain 21 ng of jasminic acid.
実施例２ ユーグレナ グラシリスの乾燥物1kgを95％エタノー
ル水溶液中に懸濁させ、塩酸によりpH4に調整した。該
懸濁液中に、水蒸気（100℃）を約１時間導入し、約60
％エタノール水になった時点で、水蒸気に代えて窒素ガ
ス（30℃）を吹き込み、エタノールをほぼ全量回収し
た。その後、残渣を凍結乾燥させて、残留水分を除去し
て、粘性物質を得た。Example 2 1 kg of a dried product of Euglena gracilis was suspended in a 95% aqueous ethanol solution and adjusted to pH 4 with hydrochloric acid. Steam (100 ° C.) is introduced into the suspension for about 1 hour,
When the water became% ethanol water, nitrogen gas (30 ° C.) was blown in instead of steam to recover almost all ethanol. Thereafter, the residue was freeze-dried to remove residual moisture, and a viscous substance was obtained.
この粘性物質をシリカゲル分配カラムクロマトグラフ
ィー（シリカゲル（ワコーゲルC100、和光純薬製）150
g、カラム：直径1.1cm×長さ35cm、固定相:0.5Mギ酸、
移動相:n−ヘキサン／酢酸エチル混合溶媒）に供して、
１％酢酸エチル分画を得た。該分画をただちに減圧濃縮
した。濃縮物にエタノール100mlを加え、更に減圧濃縮
して、ガム状物質を得た。これをシリカゲル薄層クロマ
トグラフィー（シリカゲルF254（メルク社製）0.25mm厚
さ、30×20cm、ｎ−ヘキサン／酢酸エチル／酢酸（10:
2:1,v/v/v）で15cm展開）にかけて、Rf 0.27〜0.38の展
開部分を酢酸エチルで溶出した後、ただちに大過剰のジ
アゾメタンのエーテル溶液でメチル化した。次いで、メ
チル化したものを分取ガスクロマトグラフィー（日立16
3型、カラム:1％OV−１（直径3mm×長さ2m）ガラス、カ
ラム温度:160℃、キャリアーガス：窒素、流量:35ml
分）にかけて、リテンションタイム6.88分の溶出部分を
分取した。分取したジャスミン酸メチルエステルを1N水
酸化ナトリウムで加水分解して、ジャスミン酸84ngを得
た。This viscous substance is subjected to silica gel partition column chromatography (silica gel (Wakogel C100, Wako Pure Chemical Industries) 150
g, column: 1.1 cm diameter x 35 cm length, stationary phase: 0.5 M formic acid,
Mobile phase: n-hexane / ethyl acetate mixed solvent)
A 1% ethyl acetate fraction was obtained. The fraction was immediately concentrated under reduced pressure. 100 ml of ethanol was added to the concentrate, which was further concentrated under reduced pressure to obtain a gum. This was subjected to silica gel thin layer chromatography (silica gel F254 (manufactured by Merck), 0.25 mm thick, 30 x 20 cm, n-hexane / ethyl acetate / acetic acid (10:
2: 1, v / v / v) and eluted the developed portion of Rf 0.27-0.38 with ethyl acetate, and immediately methylated with a large excess of an ether solution of diazomethane. Next, the methylated product was subjected to preparative gas chromatography (Hitachi 16
Type 3, column: 1% OV-1 (diameter 3mm x length 2m) glass, column temperature: 160 ° C, carrier gas: nitrogen, flow rate: 35ml
), An eluted portion with a retention time of 6.88 minutes was collected. The fractionated jasminic acid methyl ester was hydrolyzed with 1N sodium hydroxide to obtain jasminic acid (84 ng).
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 ＦＩ //(Ｃ１２Ｐ 7/50 Ａ０１Ｎ 37/06 Ｃ１２Ｒ 1:90） Ａ０１Ｎ 37/06 (58)調査した分野(Int.Cl.6，ＤＢ名) A01N 63/02 - 65/00 C12P 7/50 C07C 59/82 C07C 51/00 ＷＰＩ／Ｌ（ＱＵＥＳＴＥＬ) ＣＡ（ＳＴＮ)──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. 6 Identification symbol FI // (C12P 7/50 A01N 37/06 C12R 1:90) A01N 37/06 (58) Field surveyed (Int.Cl. 6 A01N 63/02-65/00 C12P 7/50 C07C 59/82 C07C 51/00 WPI / L (QUESTEL) CA (STN)
Claims (1)
び／または微生物を90％（v/v）以上のＣ１〜４低級ア
ルコールに懸濁させ、水蒸気を吹き込むことを特徴とす
る天然ジャスミン酸の抽出分離方法。1. A method for producing natural jasminic acid, comprising suspending a plant material and / or a microorganism containing natural jasminic acid in 90% (v / v) or more C1-4 lower alcohol, and blowing steam. Extraction separation method.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2120556A JP2935055B2 (en) | 1990-05-09 | 1990-05-09 | Extraction and separation method of natural jasminic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2120556A JP2935055B2 (en) | 1990-05-09 | 1990-05-09 | Extraction and separation method of natural jasminic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0418006A JPH0418006A (en) | 1992-01-22 |
| JP2935055B2 true JP2935055B2 (en) | 1999-08-16 |
Family
ID=14789231
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2120556A Expired - Lifetime JP2935055B2 (en) | 1990-05-09 | 1990-05-09 | Extraction and separation method of natural jasminic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2935055B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102250174A (en) * | 2011-07-25 | 2011-11-23 | 吉首大学 | Method for extracting jasminin from winter jasmine leaves |
-
1990
- 1990-05-09 JP JP2120556A patent/JP2935055B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0418006A (en) | 1992-01-22 |
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