Thymoquinone manufacturing method

Abstract

The present invention provides a thymoquinone manufacturing method comprising the steps of: preparing a precursor solution by dissolving, in an organic solvent, at least one thymoquinone precursor selected from carvacrol and thymol; and irradiating the precursor solution with radiation.

Description

Thymoquinone manufacturing method

[0001] The present invention relates to a method for producing thymoquinone, and more particularly, to a method for producing thymoquinone from a precursor of thymoquinone based on the ionization energy of radiation.

[0002] Thymoquinone is a representative substance known for its diverse effects, including antidiabetic, antioxidant, anti-inflammatory, antitumor, antibacterial, and immune system stimulation. Furthermore, research has shown that thymoquinone inhibits cell proliferation against many cancers.

[0003] Meanwhile, known methods for obtaining the thymoquinone include extracting it from essential oils obtained from the flowers, stems, seeds, roots, and resins of black cumin (Nigella sativa) or Monarda fistulosa, or chemically synthesizing it using a catalyst, etc. Black cumin (Nigella sativa) and Monarda fistulosa are types of herbs that have been used as medicinal herbs for a long time, and the essential oils of these plants in particular are known to have excellent pharmacological effects.

[0004] However, the method of extracting thymoquinone from oil obtained from black cumin or Monarda fistulosa seeds has low extraction efficiency, takes a long time for the extraction process, and risks causing environmental pollution due to the use of excessive organic solvents during the extraction process. On the other hand, the method of chemically synthesizing thymoquinone using catalysts, etc. is inefficient because it requires a process that includes more than 20 synthetic steps, and some steps of the process use various toxic chemicals such as dimethylformamide, chloroform, dichloromethane, and chlorosulfonic acid, which can pose a threat to the environment and the safety of workers.

[0005] Therefore, there is a need to develop a technology to synthesize thymoquinone using a low-cost, high-efficiency, and environmentally friendly method.

[0006] The purpose of the present invention is to solve the problems of the above-mentioned prior art, and to provide a method for producing thymoquinone by a low-cost, high-efficiency, and environmentally friendly method.

[0007] According to one embodiment of the present invention, a method for preparing thymoquinone is provided, comprising the steps of preparing a precursor solution by dissolving at least one thymoquinone precursor selected from carvacrol and thymol in an organic solvent; and irradiating the precursor solution with radiation.

[0008] The manufacturing method of the present invention allows for the production of large quantities of thymoquinone in a short period of time through relatively simple steps, thereby facilitating efficient production of thymoquinone. Furthermore, the manufacturing method of the present invention utilizes gamma rays to synthesize thymoquinone without the use of toxic chemicals, thereby preventing environmental pollution resulting from the thymoquinone manufacturing process.

[0009] Figure 1 is a flow chart of a method for manufacturing thymoquinone according to one embodiment of the present invention.

[0010] Figure 2 is a result of confirming the conversion of carvacrol and thymol through GC-MS analysis after dissolving carvacrol and thymol in an organic solvent and irradiating them with gamma rays according to one embodiment of the present invention.

[0011] More specifically, Fig. 2(a) and Fig. 2(c) show the results of gas chromatography performed on a precursor solution prepared by sequentially dissolving carvacrol in an organic solvent before (Fig. 2(a)) and after (Fig. 2(c)) gamma-ray irradiation, respectively. Fig. 2(e) and Fig. 2(g) show the results of mass spectrometry performed on a substance detected at Peak 1 of the gas chromatography result (Fig. 2(e)) and a thymoquinone standard (Fig. 2(g)).

[0012] Meanwhile, Fig. 2(b) and Fig. 2(d) show the results of gas chromatography performed on a precursor solution prepared by sequentially dissolving thymol in an organic solvent before (Fig. 2(b)) and after (Fig. 2(d)) gamma-ray irradiation, respectively. Fig. 2(f) and Fig. 2(h) show the results of mass spectrometry performed on a substance detected at Peak 2 of the gas chromatography result (Fig. 2(f)) and a thymoquinone standard (Fig. 2(h)).

[0013] Figure 3 is to confirm whether the substance converted from carvacrol is thymoquinone. 1 The results of H NMR (CIP-1' in CDCl3, 600 MHz) analysis (Fig. 3(a)) and 13 This is the result of C NMR (CIP-1' in CDCl3150 MHz) analysis (Fig. 3(b)).

[0014] Figure 4 is a follow-up to confirm whether the substance converted from thymol is thymoquinone. 1 The results of H NMR (CIP-1' in CDCl3, 600 MHz) analysis (Fig. 4(a)) and 13 This is the result of C NMR (CIP-1' in CDCl3150 MHz) analysis (Fig. 4(b)).

[0015] Figure 5 shows the results of analyzing the amount of thymoquinone produced according to the gamma-ray absorbed dose. More specifically, Figure 5(a) shows the results of analyzing the content of thymoquinone produced from carvacrol according to the gamma-ray absorbed dose using GC-MS, and Figure 5(b) shows the results of analyzing the content of thymoquinone produced from thymol according to the gamma-ray absorbed dose using GC-MS.

[0016] Figure 6 shows the results of analyzing the amount of thymoquinone produced according to the type of organic solvent in which thymol or carvacrol was dissolved. More specifically, Figure 6(a) shows the results of analyzing the amount of thymoquinone produced by GC-MS after preparing a precursor solution using hexane, ethyl acetate, methanol, or ethanol as an organic solvent for dissolving carvacrol and irradiating it with gamma rays. Figure 6(b) shows the results of analyzing the amount of thymoquinone produced by GC-MS after preparing a precursor solution using hexane, ethyl acetate, methanol, or ethanol as an organic solvent for dissolving thymol and irradiating it with gamma rays.

[0017] Hereinafter, preferred embodiments of the present invention will be described with reference to the attached drawings. However, the present invention may be modified in various other forms, and the scope of the present invention is not limited to the embodiments described below.

[0018] According to one embodiment of the present invention, a method for preparing thymoquinone is provided, comprising the steps of preparing a precursor solution by dissolving at least one thymoquinone precursor selected from carvacrol and thymol in an organic solvent; and irradiating the precursor solution with radiation.

[0019] For example, FIG. 1 shows a flowchart of a method for manufacturing thymoquinone according to one embodiment of the present invention.

[0020] In the step of preparing the precursor solution, at least one thymoquinone precursor selected from carvacrol and thymol can be dissolved in an organic solvent to prepare the precursor solution.

[0021] As the organic solvent, at least one selected from hexane and ethyl acetate may be used, and more preferably, hexane may be used.

[0022] The concentration of the thymoquinone precursor in the precursor solution may be 0.1 mM to 5 mM, and more specifically, 0.5 mM to 2 mM.

[0023] If the concentration of the thymoquinone precursor in the above precursor solution is less than 0.1 mM, the production amount may be low and an excessive amount of organic solvent may be used, resulting in unnecessary costs. If it exceeds 5 mM, the production rate of thymoquinone may be low.

[0024] A method for producing thymoquinone according to one embodiment of the present invention includes a step of irradiating the precursor solution with radiation.

[0025] The above radiation may be selected from the group consisting of gamma rays, X-rays, and electron rays. For example, the gamma rays may be gamma rays emitted from any one radioactive isotope selected from the group consisting of cobalt (Co)-60, krypton (Kr)-85, strontium (Sr)-90, and cesium (Cs)-137.

[0026] Upon exposure to radiation as described above, carvacrol can be converted into thymoquinone through the reaction described in Equation 1 below.

[0027] [Formula 1]

[0028]

[0029] Additionally, upon exposure to radiation, thymol can be converted into thymoquinone through the reaction described in Equation 2 below.

[0030] [Formula 2]

[0031]

[0032] Meanwhile, the step of irradiating the radiation may be performed by irradiating with a total absorbed dose of 5 to 25 kGy, more specifically by irradiating with a total absorbed dose of 10 to 20 kGy, and even more specifically by irradiating with a total absorbed dose of 10 kGy.

[0033] In the step of irradiating the above radiation, if the absorbed dose of the radiation irradiated is less than 5 kGy, the reaction of converting the precursor of thymoquinone into thymoquinone may not proceed smoothly. On the other hand, if the absorbed dose of the radiation irradiated exceeds 25 kGy, the precursor of thymoquinone or the generated thymoquinone may be decomposed due to excessive radiation.

[0034] Meanwhile, the method for producing thymoquinone according to one embodiment of the present invention may additionally include a step of purifying the produced thymoquinone.

[0035] The step of purifying the above-mentioned produced thymoquinone can be performed by a method known in the art as a method for purifying a desired compound.

[0036] For example, the step of purifying the above-mentioned produced thymoquinone can be performed by a purification method selected from the group consisting of column chromatography, high performance liquid chromatography (HPLC), and thin-layer chromatography (TLC).

[0037] As described above, the method for producing thymoquinone according to one embodiment of the present invention is environmentally friendly because it uses relatively safe organic solvents such as hexane and ethyl acetate. Furthermore, the method for producing thymoquinone according to one embodiment of the present invention is simple in its manufacturing process, allowing for efficient production of thymoquinone.

[0038] Below, the present invention will be described in more detail through specific examples. The following examples are merely illustrative and serve to aid understanding of the present invention and are not intended to limit the scope of the present invention.

[0039] Example

[0040] 1. Production of thymoquinone using radiation (gamma rays)

[0041] Example 1

[0042] Carvacrol was dissolved in an organic solvent to prepare a precursor solution (carvacrol concentration: 1 mM), and thymoquinone was prepared by irradiating the prepared precursor solution with gamma rays.

[0043] More specifically, 2 ml of hexane (JTBaker®, Avantor Inc., Radnor, PA, USA) was used as the organic solvent for dissolving carvacrol, and the carvacrol used was one having a purity of 98% or higher (Sigma-Aldrich Co., St. Louis, MO, USA).

[0044] Gamma ray irradiation was performed at a Co-60 gamma ray irradiation facility (IR-221, MDS Nordion Inc., Kanata, Canada) located at the Advanced Radiation Research Institute (Jeongeup) of the Korea Atomic Energy Research Institute, and the irradiation was performed at a dose rate of 5 kGy per hour at room temperature (25°C) to obtain a total absorbed dose of 10 kGy.

[0045] Example 2

[0046] The same procedure as in Example 1 was followed, except that thymol was used instead of carvacrol as a thymoquinone precursor.

[0047] Example 3

[0048] The same procedure as Example 1 was followed, except that the total absorbed dose of gamma rays irradiated to the precursor solution was changed to 20 kGy.

[0049] Example 4

[0050] The same procedure as Example 2 was followed, except that the total absorbed dose of gamma rays irradiated to the precursor solution was changed to 20 kGy.

[0051] Example 5

[0052] The same procedure as Example 1 was followed, except that ethyl acetate (EtOAc) was used instead of hexane as the organic solvent.

[0053] Example 6

[0054] The same procedure as Example 2 was followed, except that ethyl acetate (EtOAc) was used instead of hexane as the organic solvent.

[0055] Comparative Example 1

[0056] The same procedure as Example 1 was followed, except that the total absorbed dose of gamma rays irradiated to the precursor solution was changed to 0 kGy.

[0057] Comparative Example 2

[0058] The same procedure as Example 2 was followed, except that the total absorbed dose of gamma rays irradiated to the precursor solution was changed to 0 kGy.

[0059] Comparative Example 3

[0060] The same procedure as Example 1 was followed, except that methanol (MeOH) was used instead of hexane as the organic solvent.

[0061] Comparative Example 4

[0062] The same procedure as Example 2 was followed, except that methanol (MeOH) was used instead of hexane as the organic solvent.

[0063] Comparative Example 5

[0064] The same procedure as Example 1 was followed, except that ethanol (EtOH) was used instead of hexane as the organic solvent.

[0065] Comparative Example 6

[0066] The same procedure as Example 2 was followed, except that ethanol (EtOH) was used instead of hexane as the organic solvent.

[0067] 2. Check whether thymoquinone is produced

[0068] Experimental Example 1: GC-MS (Gas Chromatography - Mass Spectrometry) Analysis

[0069] Whether carvacrol or thymol is converted into thymoquinone according to the thymoquinone production method described in Example 1 or Example 2 was confirmed through GC-MS analysis, and the results are shown in Figure 2. More specifically, they are as follows.

[0070] 1 μl of the precursor solution irradiated with gamma rays in Example 1 or Example 2 was injected into a GC-MS system and analyzed.

[0071] GC-MS analysis was performed using a GC-7890A / MS-5975C system (Agilent) equipped with a single quadrupole mass spectrometer (Agilent, USA), and separation was performed using a DB-5MS column (30 m × 0.25 mm, 0.25-μm film thickness; Agilent).

[0072] The oven temperature was maintained at 80°C for 2 minutes, then increased to 100°C at a rate of 3°C / min, then to 180°C at a rate of 20°C / min, and then to 300°C at a rate of 60°C / min, after which it was maintained for 3 minutes. The sample was injected at 250°C, and a helium (carrier gas) flow rate of 1 mL / min was used, and the split ratio was set to 1:1.

[0073] GC-MS detection was performed using an electron ionization system with an ionization voltage of 70 eV and an ionization temperature of 280°C. The mass scan range was set to 40–600 (m / z). Detected metabolites were identified using the NIST Mass Spectral Search Program (version 2.4; NIST, Gaithersburg, MD, USA).

[0074] The standard of thymoquinone (Sigma-Aldrich) was diluted to concentrations (100, 200, 300, 400, 500, 600, 700, 800, 900, 1000 μM) and analyzed by GC-MS to derive a standard quantitative curve. The peak area value of thymoquinone shown in the GC-MS analysis result for Example 1 or Example 2 was applied to the standard quantitative curve to confirm the conversion rate of thymoquinone by gamma rays.

[0075] As a result of GC-MS analysis, a substance presumed to be thymoquinone was detected in the precursor (carvacrol) solution irradiated with gamma rays according to Example 1 (peak 1 in Fig. 2(c)), and it was confirmed that the mass and structural characteristics of the detected substance (Fig. 2(e)) were very similar to those of the standard product of thymoquinone (Fig. 2(g)). In addition, the conversion rate from the precursor was confirmed to be 38.5%.

[0076] In addition, a substance presumed to be thymoquinone was also detected in the precursor (thymol) solution irradiated with gamma rays according to the above Example 2 (peak 2 in Fig. 2(d)), and it was confirmed that the mass and structural characteristics of the detected substance (Fig. 2(f)) were very similar to those of the standard product of thymoquinone (Fig. 2(h)). In addition, the conversion rate from the precursor was confirmed to be 54.4%.

[0077] Experimental Example 2: NMR Analysis

[0078] In order to more accurately confirm whether the substance converted from carvacrol or thymol detected through the above experimental example 1 is thymoquinone, NMR analysis was performed.

[0079] The substance converted from the detected carvacrol or thymol (peak 1 in Fig. 2(c) and peak 2 in Fig. 2(d)) was purified by column chromatography using Sephadex LH-20 gel as a filler. A more detailed method for the purified substance is as follows.

[0080] The organic solvent was removed from the precursor (carvacrol) solution irradiated with gamma rays according to Example 1 using a low-temperature vacuum concentrator to obtain a dried gamma-ray irradiated product.

[0081] High-performance liquid chromatography (HPLC) was used to analyze the presence of new compounds in the dried gamma-irradiated product. The analysis was performed in isocratic mode, using 45% MeCN / H2O as the mobile phase solvent, at a flow rate of 1.0 mL / min, and under UV 254 nm wavelength, using a YMC-Pack ODS A-302 (4.6 mm X 150 mm, YMC Co.) column.

[0082] The substance identified as a novel compound was separated and purified through column chromatography using Sephadex LH-20 gel as a packing material (elution with a solvent of 40% EtOH / H2O). As a result, 30.5 mg of thymoquinone (CIP-1) produced from gamma-irradiated carvacrol was obtained.

[0083] Using the same method, the substance produced from the precursor (thymol) solution irradiated with gamma rays according to Example 2 was separated, and 20.9 mg of thymoquinone (CIP-1') was obtained.

[0084] For the above pure separated substance, 1 H NMR (in CDCl3, 600 MHz) and 13 C NMR (in CDCl3150 MHz) analysis was performed and the results are shown in Figures 3, 4 and Table 1 below.

[0085] More specifically, Fig. 3 shows a material converted from carvacrol according to Example 1, purified as described above, 1 The results of H NMR (CIP-1 in CDCl3, 600 MHz) analysis (Fig. 3(a)) and 13 This is the result of C NMR (CIP-1 in CDCl3, 150 MHz) analysis (Fig. 3(b)).

[0086] Figure 4 shows the material converted from thymol according to Example 2, purified as described above. 1 The results of H NMR (CIP-1' in CDCl3, 600 MHz) analysis (Fig. 4(a)) and 13 This is the result of C NMR (CIP-1' in CDCl3, 150 MHz) analysis (Fig. 4(b)).

[0087] CIP-1 from carvacrol (CDCl3, 600 MHz)CIP-1' from thymol (CDCl3, 600 MHz)Ref (CDCl3, 400 MHz)Positionδ H (Jin Hz)δC , typeδ H (Jin Hz)δ C , typeδ H (Jin Hz)δ C , type1-187.5-187.5-186.92-155.0-155.0-154.636.52 (d, 1.2)130.46.52 (d, 1.2)130.46.50 (d, 1.6)130.14-188.6-188.7-188.15-145.2-145.2-144.966.58 (d, 1.2)133.86.59 (d, 1.2)133.96.58 (d, 1.6)133.672.04 (d, 1.8)15.42.04 (d, 1.8)15.42.03 (d, 1.6)15.383.03 (q, 7.2)26.53.04 (q, 7.2)26.53.05 (m)26.591.13 (d, 7.2)21.41.13 (d, 7.2)21.41.12 (d, 6.9)21.4101.13 (d, 7.2)21.41.13 (d, 7.2)21.41.12 (d, 6.9)21.4

[0088] As a result of NMR analysis, the substance converted from carvacrol is as shown in Figure 3. 1 H NMR peak (Fig. 3(a)) and 13 It can be confirmed that it has a C NMR peak (Figure 3(b)). 1 As a result of measuring the H NMR spectrum, the aromatic hydrogen signal was δ H 6.58 ( 1 H, d,J= 1.2 Hz, H-6), 6.52 ( 1 H, d, J = 1.2 Hz, H-3) was observed, and one metane hydrogen was δ H 3.03 ( 1 H, q, J = 7.2 Hz, H-8) was observed. Additionally, three methyl groups were δ H 2.04 ( 3 H, d,J= 1.2 Hz, H-7) and 1.13 ( 6 H, d,J = 7.2 Hz, H-9 and 10) were observed. 13C NMR spectrum measurement results show that two carbonyl carbon signals are each δ C Detected at 188.7 (C-4) and 187.5 (C-1), three methyl carbon signals were detected at δ C 21.4 (C-9 and 10) and 15.4 (C-7) were observed. In addition, referring to Table 1, it was confirmed that the material converted from carvacrol had the same peak pattern as the thymoquinone standard (refer to "Ref" in Table 1) in the NMR analysis result (refer to "CIP-1 from carvacrol" in Table 1). Accordingly, it was confirmed that the material converted from carvacrol was thymoquinone.

[0089] In addition, the material converted from thymol is as shown in Fig. 4. 1 H NMR peak (Fig. 4(a)) and 13 It can be confirmed that it has a C NMR peak (Fig. 4(b)). In addition, referring to Table 1, it can be confirmed that the material converted from thymol has the same peak pattern as the thymoquinone standard product (see "CIP-1' from thymol" in Table 1) as the result of NMR analysis. Accordingly, it can be confirmed that the material converted from thymol is thymoquinone.

[0090] Accordingly, according to one embodiment of the present invention, it was confirmed that thymoquinone can be produced from a thymoquinone precursor composed of at least one of carvacrol and thymol by gamma ray irradiation.

[0091] Experimental Example 3: Analysis of thymoquinone production according to gamma-ray absorbed dose

[0092] The following experiment analyzed the amount of thymoquinone produced according to the absorbed dose of gamma rays.

[0093] In the step of irradiating the precursor solution with gamma rays, GC-MS analysis was performed in the same manner as in Experimental Example 1 for Examples 1 to 4 and Comparative Examples 1 and 2, where the gamma rays were irradiated at a total absorbed dose of 0, 10, or 20 kGy, to detect thymoquinone. Thereafter, the peak area value of thymoquinone shown in the GC-MS analysis result was applied to the standard quantitative curve to derive the amount of thymoquinone produced from carvacrol or thymol according to the total absorbed dose of gamma rays (Fig. 5).

[0094] Figure 5(a) shows the results of analyzing the content of thymoquinone generated from carvacrol according to the gamma-ray absorbed dose using GC-MS. Referring to Figure 5(a), when carvacrol was not irradiated with gamma rays, no thymoquinone was generated (Comparative Example 1), but when irradiated with gamma rays to a total absorbed dose of 10 kGy, it was confirmed that 385 μM of thymoquinone was generated (Example 1). On the other hand, when irradiated with gamma rays to a total absorbed dose of 20 kGy, it was confirmed that the amount of thymoquinone generated was 302 μM (Example 3).

[0095] Meanwhile, Fig. 5(b) shows the results of analyzing the content of thymoquinone generated from thymol according to the gamma-ray absorbed dose using GC-MS. Referring to Fig. 5(b), when thymol was not irradiated with gamma rays, no thymoquinone was generated (Comparative Example 2), but when irradiated with gamma rays to a total absorbed dose of 10 kGy, it was confirmed that 544 μM of thymoquinone was generated (Example 2). In addition, when irradiated with gamma rays to a total absorbed dose of 20 kGy, it was confirmed that the amount of thymoquinone generated was 554 μM (Example 4).

[0096] Experimental Example 4: Analysis of the amount of thymoquinone produced according to the organic solvent used to dissolve the precursor.

[0097] The following experiments analyzed the amount of thymoquinone produced according to the organic solvent used to dissolve the precursor.

[0098] For Examples 1, 2, 5, 6 and Comparative Examples 3 to 6, in which hexane (Hexane, Examples 1 and 2), ethyl acetate (EtOAc, Examples 5 and 6), methanol (MeOH, Comparative Examples 3 and 4) or ethanol (EtOH, Comparative Examples 5 and 6) was used as an organic solvent for dissolving carvacrol or thymol, GC-MS analysis was performed in the same manner as in Experimental Example 1 to detect thymoquinone, and the peak area value of thymoquinone shown in the GC-MS analysis result was applied to the standard quantitative curve to derive the amount of thymoquinone according to the organic solvent used (Fig. 6).

[0099] Figure 6(a) shows the results of analyzing the amount of thymoquinone produced by GC-MS after preparing a precursor solution using hexane, ethyl acetate, methanol, or ethanol as an organic solvent for dissolving carvacrol and irradiating it with gamma rays. Referring to Figure 6(a), when methanol or ethanol was used as an organic solvent, thymoquinone was not produced even when gamma rays were irradiated to a precursor solution dissolving carvacrol or thymol (Comparative Examples 5 and 7), and when ethyl acetate was used, it was confirmed that 32 μM of thymoquinone was produced (Example 5). On the other hand, when hexane was used as an organic solvent, it was confirmed that the amount of thymoquinone produced increased significantly to 385 μM (Example 1).

[0100] Meanwhile, Fig. 6(b) shows the results of analyzing the amount of thymoquinone produced by GC-MS after preparing a precursor solution using hexane, ethyl acetate, methanol, or ethanol as an organic solvent for dissolving thymol and irradiating it with gamma rays. Referring to Fig. 6(b), when methanol or ethanol was used as an organic solvent, thymoquinone was not produced even when gamma rays were irradiated to the precursor solution dissolving thymol (Comparative Examples 4 and 6), and when ethyl acetate was used, it was confirmed that 114 μM of thymoquinone was produced (Example 6). On the other hand, when hexane was used as an organic solvent, it was confirmed that the amount of thymoquinone produced increased significantly to 544 μM (Example 2).

[0101] From the above results, it was confirmed that a large amount of thymoquinone can be produced when a precursor of thymoquinone composed of at least one of carvacrol and thymol is dissolved in a specific solvent to produce a precursor solution and then irradiated with gamma rays. It was also confirmed that the amount of thymoquinone produced was the highest when hexane was used as the organic solvent.

Claims

1. A step of preparing a precursor solution by dissolving at least one thymoquinone precursor selected from carvacrol and thymol in an organic solvent; and a step of irradiating the precursor solution with radiation. A method for producing thymoquinone, comprising:

2. In paragraph 1, A method for producing thymoquinone, wherein the organic solvent is at least one selected from hexane and ethyl acetate.

3. In paragraph 1, A method for producing thymoquinone, wherein the concentration of the thymoquinone precursor in the precursor solution is 0.1 mM to 5 mM.

4. In paragraph 1, A method for producing thymoquinone, wherein the step of irradiating the above-mentioned radiation is performed by irradiating with a total absorbed dose of 5 to 25 kGy.

5. In paragraph 1, A method for producing thymoquinone, wherein the step of irradiating the above-mentioned radiation is performed by irradiating with a total absorbed dose of 10 to 20 kGy.

6. In paragraph 1, A method for producing thymoquinone, wherein the above radiation is selected from the group consisting of gamma rays, X-rays and electron rays.

7. A method for producing thymoquinone, further comprising a step of purifying the produced thymoquinone in the first paragraph.

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