JPS6339594A - Production of lactone - Google Patents
Production of lactoneInfo
- Publication number
- JPS6339594A JPS6339594A JP18267386A JP18267386A JPS6339594A JP S6339594 A JPS6339594 A JP S6339594A JP 18267386 A JP18267386 A JP 18267386A JP 18267386 A JP18267386 A JP 18267386A JP S6339594 A JPS6339594 A JP S6339594A
- Authority
- JP
- Japan
- Prior art keywords
- lipase
- hydroxycarboxylic acid
- lactone
- acid ester
- reaction
- 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.)
- Granted
Links
- 150000002596 lactones Chemical class 0.000 title claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 102000004882 Lipase Human genes 0.000 claims abstract description 25
- 108090001060 Lipase Proteins 0.000 claims abstract description 25
- 239000004367 Lipase Substances 0.000 claims abstract description 25
- 235000019421 lipase Nutrition 0.000 claims abstract description 25
- -1 hydroxycarboxylic acid ester Chemical class 0.000 claims abstract description 14
- 239000002904 solvent Substances 0.000 claims abstract description 12
- 238000007363 ring formation reaction Methods 0.000 claims abstract description 8
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 abstract description 3
- CXHHBNMLPJOKQD-UHFFFAOYSA-N methyl hydrogen carbonate Chemical compound COC(O)=O CXHHBNMLPJOKQD-UHFFFAOYSA-N 0.000 abstract description 2
- 230000006866 deterioration Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000000047 product Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 8
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 241000589516 Pseudomonas Species 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 125000005456 glyceride group Chemical group 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 101000968491 Pseudomonas sp. (strain 109) Triacylglycerol lipase Proteins 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000007273 lactonization reaction Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は、ヒドロキシカルボン酸のエステル化物を環化
反応させてラクトンを製造する方法に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a method for producing a lactone by subjecting an esterified product of hydroxycarboxylic acid to a cyclization reaction.
分子内にラクトン構造を有する化合物は、一般に生物活
性を示すものや香気を有するものが多く、医薬や香料或
いはこれらの原料として利用されている。Compounds having a lactone structure in their molecules generally exhibit biological activity or have an aroma, and are used as medicines, fragrances, or raw materials thereof.
［従来の技術］ ヒドロキシカルボン酸を分子内縮合させて。[Conventional technology] By intramolecular condensation of hydroxycarboxylic acids.
ラクトンを製造する方法としては、重合、解重合法と活
性化法とが広く知られている。Polymerization, depolymerization, and activation methods are widely known as methods for producing lactones.
上記前者の方法は、ヒドロキシ脂肪酸の加熱重縮合によ
って得られる直鎖状ポリエステルをアルキル金属酸化物
を触媒として解重合、閉環する方法である（特開昭５０
−６９０８８号又は特開昭５５−２６４０号公報）。The former method is a method in which a linear polyester obtained by heating polycondensation of hydroxy fatty acids is depolymerized and ring-closed using an alkyl metal oxide as a catalyst (Japanese Patent Application Laid-Open No. 1983-1991).
-69088 or JP-A-55-2640).
一方上記後者の方法は、ヒドロキシカルボン酸をハロビ
リジニラ・ム塩、ハロキノリウム塩誘導体と反応させて
、分子内縮合させる方法又ある（特開昭５２−１５１１
８５号、特公昭６１−１１２３１号公報）。On the other hand, the latter method is a method in which hydroxycarboxylic acid is reacted with a haloviridinyl salt or a haloquinolium salt derivative to undergo intramolecular condensation (Japanese Patent Application Laid-Open No. 52-1511
No. 85, Japanese Patent Publication No. 61-11231).
［発明が解決しようとする問題点］
上記重合、解重合法は、高温、減圧等の苛酷な条件下に
反応させなければならず、熱にたいして不安定な化合物
１例えば、多くの側鎖や官能基を有するものを原料とす
る場合は、適用できない。しかも、重合度を制御する必
要が有るため、高純度の原料を用いなければならず、又
製品中に熱劣化物が、混入するため、最終製品が香料等
の場合、その品質を著しく低下させる等の問題点があっ
た。[Problems to be Solved by the Invention] The above polymerization and depolymerization methods require reactions to be carried out under harsh conditions such as high temperature and reduced pressure. It cannot be applied when the raw material is a material having a group. Moreover, since it is necessary to control the degree of polymerization, highly pure raw materials must be used, and heat-degraded products are mixed into the product, which significantly reduces the quality of the final product, such as fragrances. There were problems such as.
また、活性化法は、高価で、しかも特殊な試薬を用いる
ため、この試薬の入手或いは合成が困雅であり、製造コ
ストを著しく高いものにしていた。Furthermore, since the activation method uses expensive and special reagents, it is difficult to obtain or synthesize these reagents, making the manufacturing cost extremely high.
本発明は、かかる問題を解決したもので、本発明の目的
は、温和な条件下に、しかも安価な試薬を用いてラクト
ンを製造する方法を提供することにある。The present invention has solved this problem, and an object of the present invention is to provide a method for producing lactone under mild conditions and using inexpensive reagents.
［問題点を解決するための手段］
本発明は、ヒドロキシカルボン酸エステルをリパーゼの
存在下に環化反応させてラクトンを製造する方法で、特
に好ましくは、荊記環化反応をリパーゼを添加した溶媒
中にヒドロキシカルボン酸エステルの溶液を滴下させる
ことにより行うものである。[Means for Solving the Problems] The present invention is a method for producing a lactone by cyclizing a hydroxycarboxylic acid ester in the presence of a lipase, and particularly preferably, the Jingji cyclization reaction is carried out by adding a lipase. This is carried out by dropping a solution of hydroxycarboxylic acid ester into a solvent.
本発明において用いられるヒドロキシカルボン酸のエス
テル化物とは、目的とする大環状ラクトンに相当するも
のが選択されることは言うまでもないが、炭素数７以上
の長鎖のω−ヒドロキシカルボン酸或いは（ω−１）−
ヒドロキシカルボン酸等のエステル化物が好適である。It goes without saying that the esterified product of hydroxycarboxylic acid used in the present invention is selected from those corresponding to the target macrocyclic lactone; -1)-
Esterified products such as hydroxycarboxylic acids are suitable.
エステルとして、メチル、エチル、ブチル等、低級アル
コールとのエステル化物を用いると、環化反応後の製品
の精製が容易となり好ましい。It is preferable to use an esterified product with a lower alcohol such as methyl, ethyl, butyl as the ester because it facilitates purification of the product after the cyclization reaction.
リパーゼは、グリセリドを段階的にグリセリンと脂肪酸
に加水分解する反応をｆ牲媒する酵素で、ヒト、動物、
カビ、酵母、細菌等いずれの由来のリパーゼでも使用で
きる。Lipase is an enzyme that mediates the stepwise hydrolysis of glyceride into glycerin and fatty acids.
Lipases derived from any source such as mold, yeast, or bacteria can be used.
次に、環化反応の好ましい態様を説明する。Next, preferred embodiments of the cyclization reaction will be explained.
先ず、リパーゼを溶媒に添加する。この場合のリパーゼ
の濃度は、用いる酵素の活性により一概に決めることは
できないが、通常は、 ０．０１〜５％程度とすれば良
い。First, lipase is added to the solvent. The concentration of lipase in this case cannot be determined unconditionally depending on the activity of the enzyme used, but it is usually about 0.01 to 5%.
リパーゼを分散させる液は疎水性溶媒を用いることが好
ましい。一般に、酵素は、水の介在下に触媒作用を行な
うが、本発明における反応においては、リパーゼ自身が
内部に保有する水で充分である。従って、有機溶媒でも
使用できるが、その内でも親水性の溶媒は、リパーゼ内
部の水と親和し、リパーゼの立体構造を変化させて失活
させる場合があり、あまり好ましくない。It is preferable to use a hydrophobic solvent as the liquid in which lipase is dispersed. Generally, enzymes carry out their catalytic action in the presence of water, but in the reaction of the present invention, the water contained within the lipase itself is sufficient. Therefore, although organic solvents can be used, hydrophilic solvents are not so preferred because they have an affinity for the water inside lipase and may change the three-dimensional structure of the lipase, thereby deactivating it.
また、原料にメチルエステル或いはエチルエステル化物
を用いる場合、反応の進行に伴い、親水性のメチルアル
コール或いはエチルアルコール等が生成し、リパーゼの
触媒作用を失活させるので、メチルアルコールやエチル
アルコール等に対して、溶解力の大きい、ベンゼン、シ
クロヘキサン、トルエン等を用いると、失活が緩和され
、特に好ましい。In addition, when using methyl ester or ethyl ester as a raw material, as the reaction progresses, hydrophilic methyl alcohol or ethyl alcohol is generated, which deactivates the catalytic action of lipase. On the other hand, it is particularly preferable to use benzene, cyclohexane, toluene, etc., which have a large dissolving power, because deactivation is alleviated.
尚、溶媒として水を用いても良いが、原料であるヒドロ
キシカルボン酸エステルが、水にほとんど溶解しないた
め、反応に時間がかかりあまり好ましくない。Note that water may be used as a solvent, but this is not very preferable since the hydroxycarboxylic acid ester, which is a raw material, hardly dissolves in water, and the reaction takes a long time.
上記のように、リパーゼを添加した溶媒にヒドロキシカ
ルボン酸エステルを、育下する。このヒドロキシカルボ
ン酸エステルは溶媒に溶解して用いた方が反応効率上好
ましい。この場合の溶媒は、リパーゼを添加した溶媒と
同じものが、溶剤回収を簡便に行うために好ましい。As described above, a hydroxycarboxylic acid ester is grown in a solvent to which lipase is added. It is preferable to use this hydroxycarboxylic acid ester dissolved in a solvent in terms of reaction efficiency. The solvent in this case is preferably the same as the solvent to which the lipase was added in order to facilitate solvent recovery.
ヒドロキシカルボン酸エステル溶液の濃度は、滴下速度
との関係で適宜法められるが通常は０．０１〜１重量％
の範囲とすると良い。０．０１重量％以下であれば、反
応速度が著しく遅くなり好ましくない。又、１重量％以
上とすると、分子間反応、すなわちポリエステル化反応
が優位となり、分子内環化反応によるラクトンの収率が
低下して好ましくない。又、同様の理由により上記範囲
の濃度のエステル溶液を５〜２４時間かけて添加するこ
とが好ましい。The concentration of the hydroxycarboxylic acid ester solution is determined as appropriate in relation to the dropping rate, but is usually 0.01 to 1% by weight.
It is good to have a range of . If it is less than 0.01% by weight, the reaction rate will be extremely slow, which is not preferable. Moreover, when it is 1% by weight or more, intermolecular reactions, that is, polyesterification reactions become dominant, and the yield of lactone due to intramolecular cyclization reactions decreases, which is not preferable. Further, for the same reason, it is preferable to add an ester solution having a concentration within the above range over a period of 5 to 24 hours.
一方、反応温度は、リパーゼの種類により一概に決めら
れないが、リパーゼのグリセリドの加水分解作用の活性
とほぼ同じ温度で、ラクトン化反応の活性をも示してお
り、通常の酵素反応と同様５〜５０ ’Ｃの温度で適宜
選定さ、ｒＬろ。On the other hand, the reaction temperature cannot be determined unconditionally depending on the type of lipase, but the activity of the lactonization reaction is approximately the same as that of lipase's glyceride hydrolysis activity, and the same temperature as that of a normal enzymatic reaction. Select a temperature of ~50'C, rL filter.
また反応時間は、滴下開始後２４時間も反応すれば充分
である。Further, the reaction time is sufficient if the reaction is continued for 24 hours after the start of the dropwise addition.
［作 用］
本発明は、ヒドロキシカルボン酸エステルがリパーゼに
より加水分解され、次いで、その反応機構は未だ解明さ
れていないが、分子内環化反応を起こしてラクトンを生
成する。[Function] In the present invention, a hydroxycarboxylic acid ester is hydrolyzed by a lipase, and then, although the reaction mechanism has not yet been elucidated, an intramolecular cyclization reaction occurs to produce a lactone.
［実施例コ
ＩＱの４つロフラスコ中に脱水したベンゼン２００ｍ１
を入れ、これに細菌シュードモナス（Ｐｓｅｕｄｏｍｏ
ｎａｓ）から得られたリパーゼ（長瀬生化学（株）１．
リパーゼＰ）を３ｇ加え、３０°Ｃの温度に保持し、マ
グネテインクスターラーで激しく攪拌しながら、表に示
した種類のヒドロキシカルボン酸メチルエステル６０■
を脱水ベンゼン１００ｍ１に溶解した液を滴下し、一定
の反応時間、攪拌を続けて反応させた。[Example: 200 ml of dehydrated benzene in 4 flasks of IQ
and put the bacterium Pseudomonas (Pseudomonas) into this.
Lipase obtained from nas) (Nagase Biochemical Co., Ltd.) 1.
Add 3 g of Lipase P), maintain the temperature at 30°C, and stir vigorously with a magnetic stirrer to add 60 μg of hydroxycarboxylic acid methyl ester of the type shown in the table.
A solution prepared by dissolving 100ml of dehydrated benzene was added dropwise, and the reaction was continued with stirring for a certain reaction time.
反応終了後の液を限外口過してリパーゼを除き、シリカ
ゲルカラムで分離し、赤外吸光分析、マススペクトル分
析、Ｎ Ｍ Ｒ分析により、表に示した生成物であるこ
とを確認、重量分析により収率を測定し、この結果も併
せて表に示した。After the reaction, the liquid was ultrafiltrated to remove lipase, separated using a silica gel column, and confirmed to be the product shown in the table by infrared absorption analysis, mass spectrometry analysis, and NMR analysis. The yield was determined by analysis, and the results are also shown in the table.
表
［発明の効果］
本発明は、ヒドロキシカルボン酸エステルをリパーゼの
存在下にラクトン化するため、温和な条件で反応させる
ことができて熱劣化物の混入がなく、品質上優れた製品
を得ることができる。また、本発明は、リパーゼという
比１鮫的入手の容易な、安価な試薬を用いるため、製造
コストを著しく低下できる。さらに、本発明は、酵素作
用を利用するため不斉炭素を有する原料を用いれば、立
体特異性を有するラクトンをも製造することができると
いう効果もあわせ持つ。Table [Effects of the Invention] The present invention lactonizes hydroxycarboxylic acid esters in the presence of lipase, so the reaction can be carried out under mild conditions and there is no contamination of heat-degradable products, resulting in products with excellent quality. be able to. Furthermore, since the present invention uses lipase, a relatively easily available and inexpensive reagent, manufacturing costs can be significantly reduced. Furthermore, the present invention also has the effect that lactones having stereospecificity can be produced by using a raw material having an asymmetric carbon to utilize enzymatic action.
Claims (2)
下に環化反応させることを特徴とするラクトンの製造方
法。(1) A method for producing lactone, which comprises subjecting a hydroxycarboxylic acid ester to a cyclization reaction in the presence of lipase.
ドロキシカルボン酸エステルの溶液を滴下することによ
り行われることを特徴とする特許請求の範囲第１項記載
のラクトンの製造方法。(2) The method for producing a lactone according to claim 1, wherein the cyclization reaction is carried out by dropping a solution of a hydroxycarboxylic acid ester into a solvent containing lipase.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18267386A JPH0710234B2 (en) | 1986-08-05 | 1986-08-05 | Method for producing lactone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18267386A JPH0710234B2 (en) | 1986-08-05 | 1986-08-05 | Method for producing lactone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6339594A true JPS6339594A (en) | 1988-02-20 |
| JPH0710234B2 JPH0710234B2 (en) | 1995-02-08 |
Family
ID=16122433
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18267386A Expired - Lifetime JPH0710234B2 (en) | 1986-08-05 | 1986-08-05 | Method for producing lactone |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0710234B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5023347A (en) * | 1988-08-05 | 1991-06-11 | International Flavors & Fragrances Inc. | Process for preparing compositions containing unsaturated lactones, products produced thereby and organoleptic uses of said products |
| US5505938A (en) * | 1993-09-30 | 1996-04-09 | Lever Brothers Company, Division Of Conopco, Inc. | Straight chain saturated or unsaturated C8 -C18 alkyl aldonolactone esters and an enzymatic process for their preparation |
| EP0862911A3 (en) * | 1997-03-05 | 2000-04-26 | Haarmann & Reimer Gmbh | Use of macrocyclic lactones as fragrances |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013128440A (en) * | 2011-12-21 | 2013-07-04 | Takasago Internatl Corp | Method for producing macrocyclic lactone having musky fragrance |
| CN112424338A (en) | 2018-07-17 | 2021-02-26 | 科纳根公司 | Biosynthetic production of gamma-lactones |
-
1986
- 1986-08-05 JP JP18267386A patent/JPH0710234B2/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5023347A (en) * | 1988-08-05 | 1991-06-11 | International Flavors & Fragrances Inc. | Process for preparing compositions containing unsaturated lactones, products produced thereby and organoleptic uses of said products |
| US5505938A (en) * | 1993-09-30 | 1996-04-09 | Lever Brothers Company, Division Of Conopco, Inc. | Straight chain saturated or unsaturated C8 -C18 alkyl aldonolactone esters and an enzymatic process for their preparation |
| EP0862911A3 (en) * | 1997-03-05 | 2000-04-26 | Haarmann & Reimer Gmbh | Use of macrocyclic lactones as fragrances |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0710234B2 (en) | 1995-02-08 |
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