JPH0482896A - Production of sucrose ester - Google Patents
Production of sucrose esterInfo
- Publication number
- JPH0482896A JPH0482896A JP19400490A JP19400490A JPH0482896A JP H0482896 A JPH0482896 A JP H0482896A JP 19400490 A JP19400490 A JP 19400490A JP 19400490 A JP19400490 A JP 19400490A JP H0482896 A JPH0482896 A JP H0482896A
- Authority
- JP
- Japan
- Prior art keywords
- shoots
- plant
- nicotiana
- acyl
- purified
- 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
- 229930006000 Sucrose Natural products 0.000 title claims description 10
- 239000005720 sucrose Substances 0.000 title claims description 10
- -1 sucrose ester Chemical class 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 241000208125 Nicotiana Species 0.000 claims abstract description 11
- 125000002252 acyl group Chemical group 0.000 claims abstract description 6
- 239000000126 substance Substances 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 6
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 abstract description 6
- 241000196324 Embryophyta Species 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 239000003960 organic solvent Substances 0.000 abstract description 4
- 238000012258 culturing Methods 0.000 abstract description 3
- 239000003617 indole-3-acetic acid Substances 0.000 abstract description 3
- 235000019504 cigarettes Nutrition 0.000 abstract description 2
- 238000000605 extraction Methods 0.000 abstract description 2
- 238000004811 liquid chromatography Methods 0.000 abstract description 2
- 238000000034 method Methods 0.000 abstract description 2
- 239000003375 plant hormone Substances 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000001963 growth medium Substances 0.000 abstract 1
- 230000000391 smoking effect Effects 0.000 abstract 1
- 239000012264 purified product Substances 0.000 description 19
- 239000000796 flavoring agent Substances 0.000 description 6
- 235000019634 flavors Nutrition 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 125000000185 sucrose group Chemical group 0.000 description 5
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 150000002148 esters Chemical group 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- BJHIKXHVCXFQLS-UYFOZJQFSA-N fructose group Chemical group OCC(=O)[C@@H](O)[C@H](O)[C@H](O)CO BJHIKXHVCXFQLS-UYFOZJQFSA-N 0.000 description 3
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NWBJYWHLCVSVIJ-UHFFFAOYSA-N N-benzyladenine Chemical compound N=1C=NC=2NC=NC=2C=1NCC1=CC=CC=C1 NWBJYWHLCVSVIJ-UHFFFAOYSA-N 0.000 description 2
- 230000009102 absorption Effects 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 229960002715 nicotine Drugs 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
- 239000005971 1-naphthylacetic acid Substances 0.000 description 1
- MYKOKMFESWKQRX-UHFFFAOYSA-N 10h-anthracen-9-one;sulfuric acid Chemical compound OS(O)(=O)=O.C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 MYKOKMFESWKQRX-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- IIDAJRNSZSFFCB-UHFFFAOYSA-N 4-amino-5-methoxy-2-methylbenzenesulfonamide Chemical compound COC1=CC(S(N)(=O)=O)=C(C)C=C1N IIDAJRNSZSFFCB-UHFFFAOYSA-N 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 1
- FAIXYKHYOGVFKA-UHFFFAOYSA-N Kinetin Natural products N=1C=NC=2N=CNC=2C=1N(C)C1=CC=CO1 FAIXYKHYOGVFKA-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 229910004619 Na2MoO4 Inorganic materials 0.000 description 1
- 241000208128 Nicotiana glauca Species 0.000 description 1
- 241000249968 Nicotiana umbratica Species 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 241000208292 Solanaceae Species 0.000 description 1
- 241000534944 Thia Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000005313 fatty acid group Chemical group 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- QANMHLXAZMSUEX-UHFFFAOYSA-N kinetin Chemical compound N=1C=NC=2N=CNC=2C=1NCC1=CC=CO1 QANMHLXAZMSUEX-UHFFFAOYSA-N 0.000 description 1
- 229960001669 kinetin Drugs 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 235000015393 sodium molybdate Nutrition 0.000 description 1
- 239000011684 sodium molybdate Substances 0.000 description 1
- TVXXNOYZHKPKGW-UHFFFAOYSA-N sodium molybdate (anhydrous) Chemical compound [Na+].[Na+].[O-][Mo]([O-])(=O)=O TVXXNOYZHKPKGW-UHFFFAOYSA-N 0.000 description 1
- UZKQTCBAMSWPJD-UQCOIBPSSA-N trans-Zeatin Natural products OCC(/C)=C\CNC1=NC=NC2=C1N=CN2 UZKQTCBAMSWPJD-UQCOIBPSSA-N 0.000 description 1
- UZKQTCBAMSWPJD-FARCUNLSSA-N trans-zeatin Chemical compound OCC(/C)=C/CNC1=NC=NC2=C1N=CN2 UZKQTCBAMSWPJD-FARCUNLSSA-N 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229940023877 zeatin Drugs 0.000 description 1
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明はたばこ用香喫味改良剤として有用なスクロース
エステルの製造方法に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a method for producing sucrose ester useful as a flavor improver for tobacco.
［従来の技術］
近年紙巻たばこに対する嗜好は、多様化の傾向を示して
いるが、特に喫味が軽い、すなわち低ニコチン、低ター
ルで、香味の豊かな製品にその嗜好は移りつつある。
しかし、低ニコチン、低タール製品を製造する場合、香
味、煙量の低下をきたすことから、香料の添加による香
喫味の改善がおこなわれている。しかしながら、さらに
微量で改善効果のある物質が望まれている。[Prior Art] In recent years, preferences for cigarettes have shown a tendency to diversify, and in particular, preferences are shifting toward products that are light in flavor, ie, low in nicotine, low in tar, and rich in flavor.
However, when manufacturing low-nicotine, low-tar products, the flavor and smoke amount are reduced, so flavoring is added to improve the flavor. However, there is a desire for a substance that has an improvement effect even in a smaller amount.
スクロースエステルは、微量でたばこの香喫味改善効果
がある化合物として本願出願人によってすでに出願して
いる（特願平１−３１６５０４）。Sucrose ester has already been filed by the applicant of the present application as a compound that has the effect of improving the aroma and taste of tobacco in minute amounts (Japanese Patent Application No. 1-316504).
この出願によるスクロースエステルを得る方法は、生育
したニコチアナ属植物から有機溶媒によって抽出し、分
離するものであるが、原料に植物を用いることから品質
の変動により、安定した原料の供給が困難である。The method for obtaining sucrose ester according to this application involves extracting and separating grown Nicotiana plants using an organic solvent, but since plants are used as raw materials, quality fluctuations make it difficult to provide a stable raw material. .
［発明が解決しようとする課題］
本発明の目的は前記のような問題点を克服し、スクロー
スエステルを安定かつ簡単に供給することのできるたば
こ香喫味改良剤の製造方法を提供することにある。[Problems to be Solved by the Invention] An object of the present invention is to overcome the above-mentioned problems and provide a method for producing a tobacco flavor improver that can stably and easily supply sucrose ester. .
［課題を解決するための手段］
本発明者等は上記問題点を解決すべく、鋭意検討した結
果この発明をなすに至った。すなわち、生育中のニコチ
アナ属植物から小片を切取り、これを培養してシュート
を形成させ、その葉面樹脂より、式（１）で示されるス
クロースエステルを生産する方法である。[Means for Solving the Problems] In order to solve the above-mentioned problems, the inventors of the present invention have made intensive studies and have come up with the present invention. That is, a small piece is cut from a growing Nicotiana plant, cultured to form a shoot, and the sucrose ester represented by formula (1) is produced from the leaf resin.
（夏）
［但し、Ｒ１，Ｒ２，Ｒ３は独立して炭素数 ２〜８の
直鎖または分岐の飽和または不飽和のアシル基であり、
Ｒ４は水素または直鎖または分岐の飽和または不飽和の
アシル基である。］
前記式（１）で示される化合物は、ナス科ニコチアナ属
植物の葉、花、茎部にふくまれている。特に野生種のた
ばこ植物にニコチアナ・アングラチカ等）に多量に含ま
れている。この植物の小片を、ムラシゲ・スクーグまた
はリンスマイヤー・スクーグの培養液に、植物ホルモン
としてインドール酢酸または１−ナフタリン酢酸を０．
１＝ １０ｐｐ＋＋または２．４−ジクロロフェノキシ
酢酸を０．０１〜５ ｐｐ＋＋とベンジルアデニンまた
はカイネチンまたはゼアチンを１〜Ｉ Ｑ ｐｐ＋ｉ用
い、１０〜４０℃好ましくは２２℃で、１２時間室内光
下（以下明条件と略す）で、その後１２時間暗室内下（
以下暗条件と略す）のサイクルで培養するか、または２
４時間暗条件下で約１カ月間培養し、 シュートを形成
させる。このシュートをクロロホルム、酢酸エチル、ア
セトン、メタノールなどの有機溶媒に浸析して抽出した
後、抽出物を濃縮し液体クロマトグラフィーで精製する
ことにより得ることができる。以下、実施例により本発
明の製造方法を詳細に説明する。(Summer) [However, R1, R2, R3 are independently a straight chain or branched saturated or unsaturated acyl group having 2 to 8 carbon atoms,
R4 is hydrogen or a linear or branched saturated or unsaturated acyl group. ] The compound represented by the formula (1) is contained in the leaves, flowers, and stems of plants of the genus Nicotiana, family Solanaceae. It is especially found in large amounts in wild tobacco plants (such as Nicotiana angratica). A small piece of this plant was added to a Murashige-Skoog or Linsmeyer-Skoog culture solution with 0.0% of indoleacetic acid or 1-naphthaleneacetic acid as a plant hormone.
1 = 10 pp++ or 0.01 to 5 pp++ of 2.4-dichlorophenoxyacetic acid and 1 to I Q pp+i of benzyladenine or kinetin or zeatin, at 10 to 40°C, preferably 22°C, under room light for 12 hours (hereinafter referred to as (abbreviated as "light condition") and then 12 hours in a dark room (
(hereinafter abbreviated as dark condition), or
Cultivate for about 1 month in the dark for 4 hours to form shoots. It can be obtained by immersing and extracting this shoot in an organic solvent such as chloroform, ethyl acetate, acetone, or methanol, concentrating the extract, and purifying it by liquid chromatography. Hereinafter, the manufacturing method of the present invention will be explained in detail with reference to Examples.
実施例１
ニコチアナ・アンブラチカの生葉の小片的１０ｍｇを切
取り、表−１に示す組成で調整したムラシゲ培養液１１
当り寒天８ｇ、インドール酢酸ｌｐｐｍ、ベンジルアデ
ニン１ ｐｐｍを加えた寒天培地１５ｍ１を入れた培養
瓶（φ２７ｍｍＸ ９ｈｍ）に入れ、２２℃で１２時開
明条件下、その後１２時間暗条件下のサイクルで、約１
カ月間培養しシュートを１０２．８ｇ得た。こうして得
られたシュートをクロロホルム３００ｍ１で２回抽出し
た後、抽出液をろ紙でろ過し、ろ液をロータリーエバボ
レークーで ３５°Ｃ下に濃縮し、葉面樹脂を１８６ｍ
ｇ （収率０．１８％）得た。この葉面樹脂を高速液体
クロマトグラフィー（カラム： ＹＭＣ−Ｐａｃｋ
Ａ−０２４ＳＩＬ、１０ｍｍφｘ３００ｍｍ、溶媒：
りｅ＋ｅ＋ホルム： アセトン・１１、流量： １．
５ｍｌ／ ｍ１ｎｓ 検出器： Ｒ１）によって精
製し、精製物■を１２分後に３２ ｍｇ、 精製物■
を１９分後に２８ｍｇ得た。Example 1 Murashige culture solution 11 was prepared by cutting 10 mg of fresh leaves of Nicotiana umbratica and adjusting the composition shown in Table 1.
Each bottle was placed in a culture bottle (φ27 mm x 9 hm) containing 15 ml of agar medium containing 8 g of agar, 1 ppm of indole acetic acid, and 1 ppm of benzyladenine, and incubated at 22°C under a cycle of 12 o'clock light and then 12 hours of darkness. 1
After culturing for a month, 102.8 g of shoots were obtained. After extracting the shoots thus obtained twice with 300 ml of chloroform, the extract was filtered through filter paper, and the filtrate was concentrated at 35°C using a rotary evaporator cooler to remove 186 ml of leaf resin.
g (yield 0.18%) was obtained. This leaf resin was subjected to high performance liquid chromatography (column: YMC-Pack
A-024SIL, 10mmφx300mm, solvent:
Re+e+form: Acetone 11, flow rate: 1.
5ml/mlns Detector: Purified by R1), 32 mg of purified product ■ after 12 minutes, purified product ■
28 mg of was obtained after 19 minutes.
実施例２
シュートの培養条件を１２時開明条件−１２時間暗条件
のサイクルで行うかわりに、２４時間暗条件で行う以外
は実施例１と同様な方法で培養した結果、シュートを５
０１ｇ得た。このシュートから実施例１と同様な抽出方
法により葉面樹脂を３４ｍｇ得た。この葉面樹脂を実施
例１と同様な高速液体クロマトグラフィーにより精製し
た結果、精製物Ｉを１１１１ｇ。Example 2 The shoots were cultured in the same manner as in Example 1 except that instead of culturing the shoots in a cycle of 12 o'clock light and 12 hours dark, the shoots were cultured in the dark for 24 hours.
Obtained 01g. From this shoot, 34 mg of leaf resin was obtained by the same extraction method as in Example 1. This leaf resin was purified by high performance liquid chromatography in the same manner as in Example 1, resulting in 1111 g of purified product I.
精製物■を１０ｍｇ得た。10 mg of purified product (2) was obtained.
実施例３ 精製物の同定
精製物Ｉおよび■の一部を弱アルカリ分解し、薄層クロ
マトグラフィーによる分析（プレート：ＨＰＴＬＣＡｒ
ｔ、５６４２． （Ｍｅｒｃｋ社製）、展開溶媒： ｎ
−ブタノール： イソプロパツール： 水＝３：１２：
４、発色試薬： アンスロン硫酸試薬）を行ったところ
、スクロースと同じＲｆ値０．４７を示した。なお、ア
ンススロン硫酸試薬は６６％硫酸２００ｍ１に、アンス
ロン０１ｇとチオ尿素２ｇを混溶して調製した。Example 3 Identification of purified products A part of purified products I and
t, 5642. (manufactured by Merck), developing solvent: n
-Butanol: Isopropanol: Water = 3:12:
4. Coloring reagent: Anthrone sulfuric acid reagent) showed the same Rf value as sucrose, 0.47. The anthurone sulfuric acid reagent was prepared by mixing 01 g of anthurone and 2 g of thiourea in 200 ml of 66% sulfuric acid.
また、精製物Ｉおよび■の少量のアルカリ分解物の脂肪
酸組成比を求めたところ炭素数２〜８の低級脂肪酸であ
った。 これらより、スクロースニ低級脂肪酸がエステ
ル結合しているものであると推測された。Further, when the fatty acid composition ratio of the small amount of alkaline decomposition products of purified products I and (1) was determined, it was found that they were lower fatty acids having 2 to 8 carbon atoms. From these, it was inferred that the sucrose di lower fatty acid was ester bonded.
精製物Ｉ、 １１の’ Ｈ−ＮＭＲの測定を行ったと
ころ、６３０〜６．０ｐｐｍにスクロース環のプロトン
のシグナルが観測され、２Ｄ−Ｃｏｓｙによって各プロ
トンの帰属を行った。表−２にスクロース環のプロトン
のケミカルシフトを示した。また、精製物■については
、６２．２６ｐｐｍにアセチル基のシグナルが観測され
たことにより、エステルとして結合している低級脂肪酸
の中に酢酸が存在していると考えられた。When purified product I, 11 was measured by 'H-NMR, a signal of the proton of the sucrose ring was observed at 630 to 6.0 ppm, and each proton was assigned using 2D-Cosy. Table 2 shows the chemical shifts of protons in the sucrose ring. In addition, regarding purified product (3), since a signal of an acetyl group was observed at 62.26 ppm, it was considered that acetic acid was present in the lower fatty acids bonded as an ester.
精製物Ｉおよび■の１３Ｃ−ＮＭＲの測定を行ったとこ
ろ、δ６０〜４０５ｐｐｍにスクロース環のカーボンの
シグナルが観測され、Ｃ−ＨＣｏ５ｙによって各カーボ
ンの帰属を行った。表−３にスクロース環のカーボンの
ケミカルシフトを示した。また、６１６０〜１８０ｐｐ
ｍにエステル結合由来のカルボニル基のカーボンのシグ
ナルが観測され、精製物Ｉでは、４つのカルボニル基の
シグナル（δｐｐｍ：１７２．８．１７３．８１７４．
０ １？４．７）によりテトラエステル、精製物■では
３つのカルボニル基のシグナル（δｐｐｍ：１７２．７
１？３．５．１８１．８）によりトリエステルである
と考えられた。When purified products I and (1) were measured by 13C-NMR, a signal of carbon in the sucrose ring was observed at δ60 to 405 ppm, and each carbon was assigned by C-HCo5y. Table 3 shows the chemical shifts of carbon in the sucrose ring. Also, 6160-180pp
A carbon signal of a carbonyl group derived from an ester bond was observed in m, and in purified product I, four carbonyl group signals (δppm: 172.8.173.8174.
0 1?4.7), the tetraester was obtained, and the purified product ④ had three carbonyl group signals (δppm: 172.7
1?3.5.181.8), it was considered to be a triester.
ＩＲスペクトルについては、精製物Ｉおよび■とも、特
徴的な吸収として、１７ＳＯｃｍ−にカルボニル基の吸
収、３５００ｃｍ−’に水酸基の吸収がみられた。Regarding the IR spectra, characteristic absorptions of carbonyl group at 17 SO cm-' and hydroxyl group absorption at 3500 cm-' were observed in both Purified Products I and (2).
エステルの位置を決定するためにアセチル化を行い、’
Ｈ−ＮＭＲの測定を行った。精製物Ｉでは、グルコー
ス部の６位およびフラクトース部の１．４．６位の低磁
場シフトが観測されたことにより、グルコース部の２．
３．４位およびフラクトース部の３位がエステル化され
たものであることが確認された。精製物■では、グルコ
ース部の６位およびフラクトース部の１゜３．４．６位
の低磁場シフトが観測されたことにより、グルコース部
の２．３．４位がエステル化されたものであることが確
認された。Acetylation is performed to determine the position of the ester, and '
H-NMR measurement was performed. In purified product I, a downfield shift of the 6th position of the glucose moiety and the 1.4.6th position of the fructose moiety was observed, indicating that the 2.
It was confirmed that the 3.4-position and the 3-position of the fructose moiety were esterified. In purified product ①, a down-field shift of the glucose moiety at position 6 and the fructose moiety at the 1°3.4.6 position was observed, indicating that the glucose moiety was esterified at the 2.3.4 position. This was confirmed.
以上により、精製物Ｉは、２．３．４− トリー〇−ア
シルα−ＤＩ’ルコピラノシル−３−〇−アシルーβ−
Ｄ−フラクト フ ラ ノ サ イ ド、 精製物
■ は、 ２．３．４−ト リ −〇−ア シル−α
−ローグルコピラノシル−β−Ｄ−フラクトフラノサイ
ドであると同定された。As described above, purified product I is 2.3.4-tri〇-acyl α-DI'lucopyranosyl-3-〇-acyl β-
D-fructofuranoside, purified product
■ is 2.3.4-tri-〇-acyl-α
-loglucopyranosyl-β-D-fructofuranoside.
表 ムラシゲ・スクーグ培養液組成（ｍｇ／ｌ）ＨＪＮＯｆ ＮＯＺ ＭｇＳＯｚ・７Ｈ２０ ＭｎＳＯａ ・４１＋２０ ＺｎＳ（ｌａ−７■２０ ＣＬＩＳＯＪ ・５＋＋２０ ＣａＣＩ２・２Ｈ２０ ＣＯＣｌ２・６Ｈ２０ に＋ Ｈ２ＰＯｎ ■？ＢＯ３ Ｎａ２ＭｏＯ４・２Ｈ２０ ＦｅＳＯ＜・７Ｈ２Ｏ Ｎａ２−ＥＤＴＡ Ｔｈｉａ＋＋Ｉｎｅ−ＨＣＩ ｍｙｏ−１ｎｏｓｉｔｏｌ Ｓｕｃｒｏｓｅ ２２．３ ８．６ ０．０２５ ０．０２５ ０．８３ １．７０ ６．２ ０．２５ ２７．８ ３７．３ １．０ ロース環のフ トンの カ ド （δ ｐｐ＋ｉ） 精製物Ｉ 精製物■ ４．８５ ４．９０ ４．２１ ３．４９ ４．２３ ４．１２ 表 スクロース環のカーボンの ケミカルノット（δｐｐ＋ｎ） 精製物Ｉ 精製物■ ６８．９ ７１．６ ６１．９ １０４．２ ７１．９ ６０．６ ８８．８ も３，０ ７３．７ ８１．５ ６１．３table Murashige-Skoog culture solution composition (mg/l) HJNOf NOZ MgSOz・7H20 MnSOa ・41+20 ZnS(la-7■20 CLISOJ・5++20 CaCI2・2H20 COCl2・6H20 ni＋ H2POn ■? BO3 Na2MoO4・2H20 FeSO<・7H2O Na2-EDTA Thia++Ine-HCI myo-1nositol Sucrose 22.3 8.6 0.025 0.025 0.83 1.70 6.2 0.25 27.8 37.3 1.0 loin ring tons of mosquito de (δ pp+i) Purified product I Refined product■ 4.85 4.90 4.21 3.49 4.23 4.12 table carbon of sucrose ring Chemical knot (δpp+n) Purified product I Refined product■ 68.9 71.6 61.9 104.2 71.9 60.6 88.8 Also 3,0 73.7 81.5 61.3
Claims (1)
該シュートを有機溶媒で抽出することを特徴とする式（
I ）で示されるスクロースエステルの製造方法。 ▲数式、化学式、表等があります▼（ I ） ［但し、Ｒ１、Ｒ２、Ｒ３は独立して炭素数２〜８の直
鎖または分岐の飽和または不飽和のアシル基であり、Ｒ
４は水素または直鎖または分岐の飽和または不飽和のア
シル基である。］[Claims] 1. Forming a shoot from a growing Nicotiana plant,
The formula (
A method for producing sucrose ester shown in I). ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) [However, R1, R2, and R3 are independently straight-chain or branched saturated or unsaturated acyl groups having 2 to 8 carbon atoms, and R
4 is hydrogen or a linear or branched saturated or unsaturated acyl group. ]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19400490A JPH0482896A (en) | 1990-07-24 | 1990-07-24 | Production of sucrose ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19400490A JPH0482896A (en) | 1990-07-24 | 1990-07-24 | Production of sucrose ester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0482896A true JPH0482896A (en) | 1992-03-16 |
Family
ID=16317371
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19400490A Pending JPH0482896A (en) | 1990-07-24 | 1990-07-24 | Production of sucrose ester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0482896A (en) |
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| JP2008510486A (en) * | 2004-08-23 | 2008-04-10 | ユーエス スモークレス タバコ カンパニー | Tobacco with diversity |
| EP2100896A1 (en) | 2008-03-14 | 2009-09-16 | Konica Minolta Business Technologies, INC. | Copper complex compound and electrophotographic toner containing the same |
| EP2101222A1 (en) | 2008-03-14 | 2009-09-16 | Konica Minolta Business Technologies, INC. | Electrophotographic toner |
| WO2011010509A1 (en) | 2009-07-22 | 2011-01-27 | コニカミノルタビジネステクノロジーズ株式会社 | Toner for electrophotography and metal-containing compound |
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-
1990
- 1990-07-24 JP JP19400490A patent/JPH0482896A/en active Pending
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008510486A (en) * | 2004-08-23 | 2008-04-10 | ユーエス スモークレス タバコ カンパニー | Tobacco with diversity |
| US7798153B2 (en) | 2004-08-23 | 2010-09-21 | Us Smokeless Tobacco Co. | Nicotiana Kawakamii smokeless tobacco |
| EP2100896A1 (en) | 2008-03-14 | 2009-09-16 | Konica Minolta Business Technologies, INC. | Copper complex compound and electrophotographic toner containing the same |
| EP2101222A1 (en) | 2008-03-14 | 2009-09-16 | Konica Minolta Business Technologies, INC. | Electrophotographic toner |
| WO2011010509A1 (en) | 2009-07-22 | 2011-01-27 | コニカミノルタビジネステクノロジーズ株式会社 | Toner for electrophotography and metal-containing compound |
| WO2012035876A1 (en) | 2010-09-14 | 2012-03-22 | コニカミノルタビジネステクノロジーズ株式会社 | Toner for electrophotography and image-forming method |
| WO2012148996A1 (en) * | 2011-04-27 | 2012-11-01 | R. J. Reynolds Tobacco Company | Tobacco-derived components and materials |
| US9254001B2 (en) | 2011-04-27 | 2016-02-09 | R.J. Reynolds Tobacco Company | Tobacco-derived components and materials |
| EP3545775A1 (en) * | 2011-04-27 | 2019-10-02 | R. J. Reynolds Tobacco Company | Method of extracting and isolating compounds from plants of the nicotiana species useful as flavor material |
| US10595554B2 (en) | 2011-04-27 | 2020-03-24 | R.J. Reynolds Tobacco Company | Tobacco-derived components and materials |
| CN103323562A (en) * | 2013-05-27 | 2013-09-25 | 广东中烟工业有限责任公司 | Method for detecting water-soluble sugar content in main stream smoke |
| CN107912804A (en) * | 2017-11-07 | 2018-04-17 | 中国农业科学院烟草研究所 | The method and its application of tobacco surface di-terpene and sugar esters compounds are extracted using tobacco crop field discarded object |
| CN107912804B (en) * | 2017-11-07 | 2020-07-24 | 中国农业科学院烟草研究所 | Application of tincture of aroma component on tobacco surface in perfuming tobacco product |
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