JPH0420292A - Synthesis of cis-4-t-butylcyclohexanol by permentation method - Google Patents
Synthesis of cis-4-t-butylcyclohexanol by permentation methodInfo
- Publication number
- JPH0420292A JPH0420292A JP12237590A JP12237590A JPH0420292A JP H0420292 A JPH0420292 A JP H0420292A JP 12237590 A JP12237590 A JP 12237590A JP 12237590 A JP12237590 A JP 12237590A JP H0420292 A JPH0420292 A JP H0420292A
- Authority
- JP
- Japan
- Prior art keywords
- butylcyclohexanol
- cis
- butylcyclohexanone
- medium
- added
- 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
- 238000000034 method Methods 0.000 title claims description 17
- CCOQPGVQAWPUPE-UHFFFAOYSA-N 4-tert-butylcyclohexan-1-ol Chemical compound CC(C)(C)C1CCC(O)CC1 CCOQPGVQAWPUPE-UHFFFAOYSA-N 0.000 title claims description 10
- 230000015572 biosynthetic process Effects 0.000 title description 2
- 238000003786 synthesis reaction Methods 0.000 title description 2
- 241000374462 Aspergillus pseudoglaucus Species 0.000 claims abstract description 6
- 239000000758 substrate Substances 0.000 claims abstract description 6
- 239000007788 liquid Substances 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims abstract 3
- 238000000855 fermentation Methods 0.000 claims description 7
- 230000004151 fermentation Effects 0.000 claims description 7
- RCHLXMOXBJRGNX-UHFFFAOYSA-N 1-butylcyclohexan-1-ol Chemical compound CCCCC1(O)CCCCC1 RCHLXMOXBJRGNX-UHFFFAOYSA-N 0.000 claims 1
- ZRYDPLOWJSFQAE-UHFFFAOYSA-N 2-tert-butylcyclohexan-1-one Chemical compound CC(C)(C)C1CCCCC1=O ZRYDPLOWJSFQAE-UHFFFAOYSA-N 0.000 claims 1
- 238000001308 synthesis method Methods 0.000 claims 1
- YKFKEYKJGVSEIX-UHFFFAOYSA-N cyclohexanone, 4-(1,1-dimethylethyl)- Chemical compound CC(C)(C)C1CCC(=O)CC1 YKFKEYKJGVSEIX-UHFFFAOYSA-N 0.000 abstract description 7
- 239000000344 soap Substances 0.000 abstract description 5
- POYYYXPQBFPUKS-UHFFFAOYSA-N 2-butylcyclohexan-1-one Chemical compound CCCCC1CCCCC1=O POYYYXPQBFPUKS-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000012258 culturing Methods 0.000 abstract 1
- 239000002304 perfume Substances 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 description 5
- 239000003205 fragrance Substances 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 2
- 229910021639 Iridium tetrachloride Inorganic materials 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- CALMYRPSSNRCFD-UHFFFAOYSA-J tetrachloroiridium Chemical compound Cl[Ir](Cl)(Cl)Cl CALMYRPSSNRCFD-UHFFFAOYSA-J 0.000 description 2
- 241000193830 Bacillus <bacterium> Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- -1 lithium tridiamylborohydride Chemical compound 0.000 description 1
- 239000013028 medium composition Substances 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Description
【発明の詳細な説明】
〔発明の目的〕
（産業上の利用分野）
本発明は、発酵法により４−ｔ−ブチルシクロヘキサノ
ンを還元し、４−ｔ−ブチルシクロヘキサノールのｃｉ
ｓ体のみを生成する発酵法によるｃｉｓ−４ｔ−ブチル
シクロヘキサノールの合成法に関するものである。ｃｉ
ｓ−４ｔ−ブチルシクロヘキサノールは、カンファー様
、木様の香りを持ち、石けんなどの香料として用いられ
る。Detailed Description of the Invention [Objective of the Invention] (Industrial Application Field) The present invention reduces 4-t-butylcyclohexanone by a fermentation method, and reduces the ci of 4-t-butylcyclohexanol.
This invention relates to a method for synthesizing cis-4t-butylcyclohexanol using a fermentation method that produces only the s-form. ci
s-4t-Butylcyclohexanol has a camphor-like, wood-like scent and is used as a fragrance for soaps and the like.
（従来の技術）
従来、４−ｔ−ブチルシクロヘキサノンの還元により石
けんなどの香料として用いられるｃｉ３／１−ｔ−ブチ
ルシクロヘキサノールを得る時は、四塩化イリジウムを
用いるＨ ｅ ｎ ｂ ｅ ｓ ｔ 法がトリジアミル
水素化ホウ素リチウムを用いるＢ ｒ ｏ ｗ ｎ法が
採用されていた。(Prior art) Conventionally, when obtaining ci3/1-t-butylcyclohexanol, which is used as a fragrance in soaps and the like, by reducing 4-t-butylcyclohexanone, the H e n b e st method using iridium tetrachloride has been used. However, the Brown method using lithium tridiamylborohydride was adopted.
（発明が解決しようとする課題）
しかるに、従来用いられたＨｅｎｂｅｓｔ法の四塩化イ
リジウムは非常に高価であり、また、Ｂ ｒ ｏ ｗ
ｎ法は操作が非常に煩雑であるという問題点があった。(Problems to be Solved by the Invention) However, iridium tetrachloride by the Henbest method conventionally used is very expensive, and
The n method has a problem in that the operation is very complicated.
本発明の目的は上述の問題点に鑑み、安価で簡単な方法
で４−ｔ−ブチルシクロヘキサノールのｃｉｓ体のみを
生成する、発酵法にょるｃｉｓ−４−ｔ−ブチルシクロ
ヘキサノールの合成法を提供するものである。In view of the above-mentioned problems, the object of the present invention is to provide a method for synthesizing cis-4-t-butylcyclohexanol by a fermentation method, which produces only the cis form of 4-t-butylcyclohexanol in an inexpensive and simple manner. This is what we provide.
（課題を解決するための手段）
本発明の、発酵法によるｃｉｓ−４−ｔ−ブチルシクロ
ヘキサノールの合成法は、アスペルギルス属リーペンス
種に属する菌株（ＡｓｐｅＢｉｌｌｕｓｒｅｐｅｎｓ
ＭＡ（１１９７） （微工研菌寄第ｒ、 ：１．１−
８３号）を液体培地中で培養し、この培地中で基質とし
て加えられた（１）式に示す４−ｔ−ブチルシクロヘキ
サノン
を還元し、（２）式に示すｃｉｓ−４−ｔ−ブチルシク
ロヘキサノール
を得るものである。(Means for Solving the Problems) The method for synthesizing cis-4-t-butylcyclohexanol by a fermentation method of the present invention uses a bacterial strain belonging to the genus Aspergillus repens (AspeBillus repens species).
MA (1197) (Feikoken Bacillus No. r, :1.1-
No. 83) was cultured in a liquid medium, and in this medium, 4-t-butylcyclohexanone shown in formula (1) added as a substrate was reduced to produce cis-4-t-butylcyclohexanone shown in formula (2). Hexanol is obtained.
（作用）
本発明の発酵法によるｃｉｓ−４−ｔ−ブチルシクロヘ
キサノールの合成法は、アスペルギルス属リーペンス種
に属する菌株（ＡｓｐｅＢｉｌｌｕｓｒｅｐｅｎｓ Ｍ
ＡＯＩ９７ ） （微工研菌寄第１−１．１−８３号
）を液体培地中で培養し、この培地中に基質としての４
−ｔ−ブチルシクロヘキサノンを添加すると、その還元
によりｃｉｓ−４ｉ−ブチルシクロへキサノールが生成
されるものである。(Function) The method for synthesizing cis-4-t-butylcyclohexanol by the fermentation method of the present invention is a method for synthesizing cis-4-t-butylcyclohexanol using a strain belonging to the genus Aspergillus repens (AspeBillus repens M
AOI97) (Feikoken Bacteria Serial No. 1-1.1-83) was cultured in a liquid medium, and 4 as a substrate was cultured in this medium.
When -t-butylcyclohexanone is added, cis-4i-butylcyclohexanol is produced by its reduction.
（実施例）
培地組成は次表に示すＭＹ２０培地を使用する。このＭ
Ｙ２０培地を１２０℃で２０分間殺菌した後、０． ［
５％〜（１，１％濃度きなるように基質として（１）式
の４−ｔ−ブチルシクロヘキサノンを添加する。これに
アスペルギルス属リーペンス種に属する菌株（Ａｓｐｅ
Ｂｉｌｌｕｓ ｒｅｐｅｎｔ ＭＡＯＩ９７ ）（微工
研菌寄第１１ ｉ−８３号）を接種し、２３〜２８℃で
３〜１０日間静置あるいは振とう培養すると、１８〜２
５％の４−ｔ−プチルシクロヘキザノンが（２）式のｃ
ｉ ｓ −４−ｔ−ブチルシクロヘキサノールに変換
される。得られたｃｉｓ−４−ｔ−ブチルシクロヘキサ
ノールは石けんなどの香料として利用できる。(Example) For the medium composition, MY20 medium shown in the following table is used. This M
After sterilizing Y20 medium at 120°C for 20 minutes, 0. [
4-t-butylcyclohexanone of the formula (1) is added as a substrate at a concentration of 5% to 1.1%.
When inoculated with Billus repent MAOI97 (Feikoken Bacteria No. 11 i-83) and cultured at 23 to 28°C for 3 to 10 days with shaking, 18 to 2
5% of 4-t-butylcyclohexanone was added to c of formula (2).
is converted to s-4-t-butylcyclohexanol. The obtained cis-4-t-butylcyclohexanol can be used as a fragrance for soaps and the like.
ＭＹ２０培地
グルコース ２００ｇ
ペ プ ト ン ５ ｇ酵母エ
キス ３ｇ
麦芽エキス ３ｇ
蒸 留 水 １． ０ ０ ０ ｇ〔発明の効
果〕
本発明によれば、発酵法により４−ｔ−ブチルシクロヘ
キサノンを還元するため、石けんなどの香料として用い
られるｃ ｉ ｓ −４−ｔ−ブチルシクロヘキサノー
ルの合成が高価な試薬を用いず安全かつ容易に行うこと
ができ、しかも４−ｔ−プチルシクロヘキサノールのｃ
ｉｓ体のみを選択的に生成することができる。MY20 medium Glucose 200g Peptone 5g Yeast extract 3g Malt extract 3g Distilled water 1. 0 0 0 g [Effects of the Invention] According to the present invention, since 4-t-butylcyclohexanone is reduced by a fermentation method, the synthesis of c i s -4-t-butylcyclohexanol, which is used as a fragrance in soaps, etc. It can be carried out safely and easily without using expensive reagents, and the c
Only is-forms can be selectively generated.
Claims (2)
ｓｐｅｒｇｉｌｌｕｓ ｒｅｐｅｎｓ ＭＡ０１９７）
（微工研菌寄第１１１８３号）を液体培地中で培養し、
この培地中で基質として加えられた（１）式に示す４−
ｔ−ブチルシクロヘキサノン ▲数式、化学式、表等があります▼ （１） を還元し、（２）式に示すｃｉｓ−４−ｔ−ブチルシク
ロヘキサノール ▲数式、化学式、表等があります▼(1) A strain belonging to the genus Aspergillus repens species (A
spergillus repens MA0197)
(Feikoken Bibori No. 11183) was cultured in a liquid medium,
4- shown in formula (1) added as a substrate in this medium
t-Butylcyclohexanone ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ Cis-4-t-butylcyclohexanol, which is obtained by reducing (1) and is shown in formula (2) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
ブチルシクロヘキサノールの合成法。(2) cis-4-t- by a fermentation method characterized by obtaining
Synthesis method of butylcyclohexanol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12237590A JPH0732713B2 (en) | 1990-05-11 | 1990-05-11 | Fermentation method for synthesis of cis-4-t-butylcyclohexanol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12237590A JPH0732713B2 (en) | 1990-05-11 | 1990-05-11 | Fermentation method for synthesis of cis-4-t-butylcyclohexanol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0420292A true JPH0420292A (en) | 1992-01-23 |
| JPH0732713B2 JPH0732713B2 (en) | 1995-04-12 |
Family
ID=14834286
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12237590A Expired - Lifetime JPH0732713B2 (en) | 1990-05-11 | 1990-05-11 | Fermentation method for synthesis of cis-4-t-butylcyclohexanol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0732713B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6526348B1 (en) * | 2000-08-25 | 2003-02-25 | Navigation Technologies Corp. | Method and system for compact representation of routes |
-
1990
- 1990-05-11 JP JP12237590A patent/JPH0732713B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6526348B1 (en) * | 2000-08-25 | 2003-02-25 | Navigation Technologies Corp. | Method and system for compact representation of routes |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0732713B2 (en) | 1995-04-12 |
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