JPH08889B2 - Carthamin production method - Google Patents

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a process for efficiently producing safflower from a safflower pigment (cartamine) in a high yield.

Pigments are widely used as coloring agents for foods and drinks, pharmaceuticals, cosmetics, or dyes for fibers. Recently, however, the demand for natural pigments has increased in the industry, especially from the viewpoint of safety. Is no exception.

However, since the present invention makes it possible to produce a large amount of safflower crimson pigment, which is a natural pigment, it has a great advantage to the industries utilizing natural pigments such as the cosmetics industry and the food industry.

[0004]

2. Description of the Related Art Generally, safflower is a plant of the Asteraceae family that is often cultivated in the Yamagata region, and the flowers harvested contain beautiful red pigments (cartamine), yellow pigment, and other medicinal ingredients. Because of that, dried flowers are prized as tea. The red pigment extracted from flowers is sold as a scarlet dye and as a natural lipstick.

Generally, in order to obtain safflower red pigment, first, fresh petals are crushed to change to red, then the petals are washed with water, the yellow pigment is removed, and then the dried petals are dried with an alkaline solution. By immersing and adding an acid to this alkaline yellow solution, it is turned red and a red pigment is obtained.

[0006] Recently, a method for obtaining a red pigment by inactivating the glucose oxidase by treating the red pigment precursor contained in the safflower petals with glucose oxidase and then drying with an organic solvent or hot air has been developed. Kosho 6
1-199798), it has not yet been put to practical use.

[0007]

In the above-mentioned method for producing cartamine, the method using an alkali or acid solution has a low yield due to the instability of the red pigment, and when glucose oxidase is used, the enzyme after reaction is Not only does it require operations such as inactivation and protein removal, which complicates the process and requires skill, but the loss of the product is inevitable due to these numerous steps.

As described above, it is difficult to say that any of the known methods is an industrial mass production method that can efficiently obtain cartamine without loss.

[0009]

The present invention has been made for the purpose of solving the above-mentioned problems and developing a method for efficiently mass-producing cartamine.

As a result of examination to achieve this purpose,
A method that uses an acid or alkali with a low yield of cartamine,
In addition, it was concluded that it is difficult to achieve the intended purpose by improving known methods such as a method using an enzyme that is unstable and difficult to handle and has a problem in terms of price.

Therefore, the development of a method completely different from these methods, that is, the change of idea was pressed, and as a result of extensively studying from various fields without being confined to the past technology, the aqueous solution of potassium permanganate was brought into contact with the petals of safflower. When they were allowed to react with each other, they found that carthamin can be produced extremely efficiently. The present invention has been finally completed based on this novel and useful finding.

That is, the basic technical idea of the present invention is to treat safflower with potassium permanganate to produce cartamine.

In carrying out the present invention, safflower is as follows:
All sites containing cartamine can be used. For example, when using the petals, any stage from the early stage to the end stage of flowering can be freely used. As safflower, both fresh flowers and dried flowers can be used.

In the present invention, safflower and potassium permanganate are brought into contact with each other. For that purpose, various methods are appropriately used, for example, it is possible to dissolve potassium permanganate in various solvents such as water, glacial acetic acid, ethanol, acetone, etc., and suspend safflower. In this case, the heating process shortens the processing time. As safflower, raw and / or
Alternatively, bright yellow dried petals may be used as they are, or may be crushed to an appropriate size and / or further crushed.

Specifically, the safflower petal is adjusted to 0.5 mM to 15
After suspending in mM KMnO ₄ solution (preferably 1 to 10 mM), room temperature to 40 ° C. (preferably 28 to 32 ° C.)
At 0.5 to 5 hours (preferably 1.5 to 2.5 hours)
Let react. It is preferable to stir during the reaction if possible, but it is not necessary to stir. This reaction changes all petals to safflower.

After the reaction is completed, a method known from red petals,
For example, MeOH-Pyridin method (C. Kurod
a, J. Chem. Soc. , 752-765 (193
The red pigment is extracted in 0)).

In this way, the red pigment cartamine is extracted in high yield. This can be directly used for various purposes as it is, and if necessary, it may be purified by a known purification means such as chromatography.

Examples of the present invention will be described below.

[Example 1] 300 g of safflower fresh petals were added to 5 mM.
110 ° C. at 30 ° C. in 1500 ml of KMnO ₄ aqueous solution
It was shake-cultured for 2 hours under a reaction condition of rockes / min.

As a control, 1500 units of an aqueous solution containing 2000 units of glucose oxidase (GOD).
The same treatment as above was performed using ml.

The reaction products thus obtained are each obtained by the methanol-pyridine method (C. Kuroda,
(1930), J. Am. Chem. Soc. , 752-76
5).

The extract is Avicel cellulose (eluting solvent;
65% MeOH), Sephadex LH-20 (elution solvent: 30% MeOH), Toyo Pearl H
Purification was performed by a column chromatography method using W-40f (elution solvent: 40% acetone) successively, and the solvent was distilled off under reduced pressure to obtain crystals. The results are shown in Table 1 below.

[0023]

[Table 1]

As is clear from the above results, the yield of the red pigment formed was higher in this method than in the case of using glucose oxidase.

The obtained crystals were subjected to three kinds of developing solvents, that is, BuOH: HOAc: water (4: 1: 2, v / v / using silica gel and cellulose TLC plate.
v), HOAc: water (15:85, v / v), developed with water saturated phenol. As a result of exposing the plate to ammonia vapor and comparing the Rf value of the dye emitted by ultraviolet irradiation with the Rf value of the caltamine standard product, the Rf species of this crystal coincided with that of cartamine.

As a result of measuring the absorption spectra (100 to 600 nm) of the obtained crystal and the cartamine preparation, this crystal was in agreement with the spectrum of the cartamine preparation.
From the above measurement results, this crystal was identified as cartamine.

[0027]

INDUSTRIAL APPLICABILITY In the present invention, when extracting the safflower red pigment, a completely new method of treatment with potassium permanganate is adopted, and the following remarkable effects are exhibited.

(1) By using the present invention, it is possible to obtain a larger amount of crimson dye than before.

(2) In the present invention, since the heat is not applied during the process, the magenta dye can be obtained more stably.

(3) The pigment obtained by the present invention can be safely used for dyeing foods, drinks, cosmetics, textiles and the like.

(4) The present invention is particularly suitable as an industrial method because it does not use an enzyme that requires skill in handling and management.

Claims (1)

[Claims] 1. A method for producing cartamine, which comprises contacting safflower with potassium permanganate to produce cartamine.