JPS6363385A - Production of alcohol compound by microorganism - Google Patents

Abstract

PURPOSE:To produce the titled compound useful as perfumery, herbicide, insecticide, fungicide and their intermediate, etc., on an industrial scale at a low cost, by reducing an unsaturated carboxylic acid compound having a specific cyclic structure with a pathogen of anthracnose or its treated cell. CONSTITUTION:The objective alcohol compound of formula II (e.g. 3-phenyl-2- methyl-2-propenol) can be produced by reducing an unsaturated carboxylic acid compound having a cyclic structure and expressed by formula I (X is group having cyclic structure; R is 1-6C alkyl; n is integer of 0-10) (e.g. alpha- methylcinnamic acid) with a pathogen of anthracnose [e.g. Gloeosporium olivarum Alumeida (ATCC 60905)] or its treated product.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing alcohol compounds using microorganisms.

More specifically, by culturing a carboxylic acid compound having a group having a cyclic structure with the anthrax bacterium or reducing it using a bacterial cell treatment product of the anthrax bacterium, the formula % formula % (wherein, X is (represents a group having a cyclic structure, R represents an alkyl group having 1 to 6 carbon atoms, and n represents an integer of 0 to 10)
This invention relates to a method for producing an alcohol compound represented by

The present inventors conducted research on various reduction reactions using various microorganisms, and as a result, they discovered that the charcoal fungus can carry out reduction reactions with good yield, leading to the present invention.

The starting material used in the present invention has the formula: , n represents an integer from O to 10)
Examples of the group having a cyclic structure represented by X in the formula include, but are not limited to, the following groups.

The alkyl group having 1 to 6 carbon atoms represented by R in the formula may be either a straight chain or a branched chain alkyl group.

The anthrax pathogen used in the present invention is widely distributed in the natural world, such as the apple anthrax pathogen Glomerella cingulata.
Mars SP (Gloa+erellacing)
ulate Malus spp, hereafter G, c-M
Glo+merella cingulata brunus sp.) [obtained from the Yamagata Prefecture Horticultural Research Institute];
Prunus SPP (hereinafter abbreviated as G and c-PF) [obtained from the Yamagata Horticultural Research Institute], Glomerella cingulate Prunus (Glomerella cingulate Pru)
nus (abbreviated as G, c-PL) [obtained from the Yamagata Horticultural Research Institute], Pear anthracnose fungus Glomerella cingulata Pirus sp.
Ingulate Pyrug spp.

(hereinafter abbreviated as G, c-Pyrus) [obtained from the Yamagata Horticultural Research Institute], Gloeosporium (G1oeospo)
Gloeosporium laeticolor, a bacterium that causes peach anthracnose and belongs to the genus
color (hereinafter abbreviated as G and Q) [obtained from Yamagata Horticultural Research Institute], Olive anthracnose fungus Gloeosporium olivarum almeida (Gloeosporium olivaru+i A)
lumeida hereafter G.

acquisition] etc.

To carry out the present invention, the above-mentioned microorganisms are cultured by standing or shaking in an appropriate medium containing an arbitrary starting material, and after culturing and reacting for a certain period of time, the culture solution is separated into bacterial cells and filtrate. do. This reaction can also be carried out by adding the starting material to a culture solution of microorganisms or a processed product thereof, and allowing the mixture to stand still or be shaken.

Next, the filtrate is subjected to extraction and purification operations to obtain the target substance. For example, the pH of the filtrate is adjusted to alkaline, and then extracted with an organic solvent such as ether or chloroform. After washing the extract, the desired alcohol compound can be obtained by operations such as vacuum concentration and chromatography.

Depending on the physical properties of the starting material and target material, extraction, separation,
It is preferable to change the conditions for purification and the like as appropriate.

The alcohol compounds obtained in the present invention are used as fragrances, herbicides,
It is useful as an insecticide or fungicide or as an intermediate thereof.

Example 1 Water was added to 30 g of peptone, 1.2 g of magnesium sulfate heptahydrate, 3 g of monobasic potassium phosphate, and 150 g of sucrose, and the pH was adjusted to 5.5.
- After adding 1.5 g of methyl cinnamic acid, pour into a container, cover with cotton plug, and sterilize in an autoclave.

The above sterilized medium was inoculated with various anthrax bacteria, and 25 to 2
Static culture is performed at 7°C for a predetermined number of days.

After culturing, the bacterial cells were filtered, and the filtrate was adjusted to pH 9-10 with 10% potassium hydroxide, and then added to chloroform IQ.
Extract at .

After washing this chloroform extract with water, it was distilled off under reduced pressure.
The residue was subjected to silica gel chromatography and eluted with chloroform to obtain 3-phenyl-2-methyl-2-propenol (MS m/z 148
(Mφ)) was obtained.

The results are shown in Table 1.

Table 1 Test Example 2 The procedure was carried out in the same manner as in Example 1 using 2-(2-furfurylidene)-propionic acid as the starting material, and 3-(2-furyl)-2-methyl-2-propenol (MS m/z
138 (M”)) was obtained. The results are shown in Table 2.

Table 2 Test Example 3 The same procedure as in Example 1 was carried out using 3-cyclohexene-1-carboxylic acid as the starting material (3-cyclohexenyl).
Methanol (MS m/z 113 (M◆+1)
). The results are summarized in Table 3.

Table 3

Claims (1)

[Claims] Formula▲ Numerical formula, chemical formula, table, etc.▼ (In the formula, X is a group having a cyclic structure, R is an alkyl group having 1 to 6 carbon atoms, and n is an integer of 0 to 10. )
Formulas characterized by reducing the carboxylic acid compound represented by using anthrax bacteria or its treated bacterial cells ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (wherein, X, R and n have the same meanings as above) ) The method for producing alcohol compounds represented by