salts of ergothioneine

Abstract

This invention discloses a physiologically acceptable salt of ergothioneine and a method for its preparation. The method provided by this invention can produce ergothioneine salt efficiently and stably; moreover, the ergothioneine salt of this invention solves the problem of ergothioneine having an off-flavor, and therefore has broad application prospects in the fields of dietary supplements, food, or cosmetics.

Description

Salts of ergothioneine Technical Field

[0001] The present invention relates to a physiologically acceptable salt of ergothioneine and a method for preparing the same. Background Art

[0002] Ergothioneine (EGT) is a rare, naturally occurring chiral amino acid derived from plants and capable of accumulating in animals. It is safe and non-toxic. It is a natural antioxidant with numerous physiological functions, including detoxification, maintaining DNA growth, protecting against radiation, fighting inflammation, resisting aging, protecting the nervous system, inhibiting developmental defects, and protecting the liver. Ergothioneine is present throughout the human body, with highest concentrations in the kidneys, liver, red blood cells, and semen, making it crucial for human health. Clinical studies are underway domestically and internationally on the effects of ergothioneine on cognition, mood, and sleep. Given EGT's physiological activity, it holds broad application prospects in dietary supplements, cosmetics, and pharmaceuticals.

[0003] However, thioneine is prone to produce odors such as the stink of sulfide and the stink of ammonia after seeing the light as the extension of time, which affects its application. How to avoid the annoying smell when utilizing thioneine is the key content that those skilled in the art need to study. Summary of the Invention

[0004] The present invention can prepare a stable physiologically acceptable salt of ergothioneine, has the advantages of low energy consumption and material consumption, and the obtained salt can solve problems such as odor, and can be better applied to the fields of dietary supplements, food or cosmetics.

[0005] In one aspect, the present invention provides a physiologically acceptable salt of ergothioneine, selected from one or more of hydrochloride, hydrobromide, hydroiodide, sulfate, phosphate, bisulfate, and hydrogen phosphate.

[0006] In some embodiments, the molar ratio of ergothioneine to acid is 1:3 to 3: 1. In some embodiments, the molar ratio of ergothioneine to acid is 1:3, 1:2, 1:1, 2:1, 3:1.

[0007] In some embodiments, the salt is in a crystalline form, or an amorphous form, or a mixture thereof.

[0008] In some embodiments, ergothioneine hydrochloride has an X-ray powder diffraction pattern comprising peaks at diffraction angles (2θ) of 8.18°±0.20°, 17.33°±0.20°, 20.00±0.20°, and 28.67°±0.20°.

[0009] In some embodiments, the X-ray powder diffraction pattern of ergothioneine hydrochloride further comprises one or more peaks at diffraction angles (2θ) of 11.20°±0.20°, 19.10°±0.20°, and 25.85°±0.20°.

[0010] In some embodiments, the X-ray powder diffraction pattern of ergothioneine hydrochloride further comprises one or more peaks at diffraction angles (2θ) of 13.61°±0.20°, 24.02°±0.20°, and 29.70°±0.20°.

[0011] In some embodiments, the X-ray powder diffraction pattern of ergothioneine hydrochloride is shown in FIG1 .

[0012] In some embodiments, the infrared spectrum of ergothioneine hydrochloride has the following absorption bands, expressed as the inverse of the wavelength (cm -1 )(±2cm -1 ): 3136, 3017, 2853, 2617, 1732, 1626, 1489, 1470, 1427, 1398, 1285, 1248, 1198, 1177, 1098, 976, 951, 912, 806, 640.

[0013] In some embodiments, the X-ray powder diffraction pattern of ergothioneine hydrobromide includes peaks at diffraction angles (2θ) of 11.96°±0.20°, 13.49°±0.20°, 20.77°±0.20°, and 25.02°±0.20°.

[0014] In some embodiments, the X-ray powder diffraction pattern of ergothioneine hydrobromide further comprises one or more peaks at diffraction angles (2θ) of 7.52°±0.20°, 18.93°±0.20°, and 28.86°±0.20°.

[0015] In some embodiments, the X-ray powder diffraction pattern of ergothioneine hydrobromide further comprises one or more peaks at diffraction angles (2θ) of 17.67°±0.20°, 23.48±0.20°, and 31.61°±0.20°.

[0016] In some embodiments, the X-ray powder diffraction pattern of ergothioneine hydrobromide is shown in FIG2 .

[0017] In some embodiments, the infrared spectrum of ergothioneine hydrobromide has the following absorption bands, expressed as the inverse of the wavelength (cm -1 )(±2cm -1): 3130, 3028, 2963, 2891, 2766, 1989, 1732, 1626, 1487, 1435, 1418, 1387, 1341, 1285, 1248, 1215, 1190, 1094, 974, 951.

[0018] In some embodiments, the X-ray powder diffraction pattern of ergothioneine sulfate includes peaks at diffraction angles (2θ) of 13.21°±0.20°, 19.28°±0.20°, 22.52±0.20°, and 27.23°±0.20°.

[0019] In some embodiments, the X-ray powder diffraction pattern of ergothioneine sulfate further comprises one or more peaks at diffraction angles (2θ) of 9.68°±0.20°, 16.65°±0.20°, and 24.60°±0.20°.

[0020] In some embodiments, the X-ray powder diffraction pattern of ergothioneine sulfate further comprises one or more peaks at diffraction angles (2θ) of 14.12°±0.20°, 21.30°±0.20°, and 30.00°±0.20°.

[0021] In some embodiments, the X-ray powder diffraction pattern of ergothioneine sulfate is shown in FIG3 .

[0022] In some embodiments, the infrared spectrum of ergothioneine sulfate has the following absorption bands, expressed as the inverse of the wavelength (cm -1 )(±2cm -1 ): 3142, 3034, 2895, 1736, 1632, 1487, 1248, 1217, 1188, 1080, 1047, 1011, 972, 951, 912, 876, 839, 814, 604, 588.

[0023] In some embodiments, the ergothioneine phosphate has an X-ray powder diffraction pattern comprising peaks at diffraction angles (2θ) of 5.73°±0.20°, 14.96°±0.20°, 21.73±0.20°, and 26.76°±0.20°.

[0024] In some embodiments, the X-ray powder diffraction pattern of ergothioneine phosphate further comprises one or more peaks at diffraction angles (2θ) of 11.35°±0.20°, 20.64°±0.20°, and 24.34°±0.20°.

[0025] In some embodiments, the X-ray powder diffraction pattern of ergothioneine phosphate further comprises one or more peaks at diffraction angles (2θ) of 9.41°±0.20°, 18.65°±0.20°, and 28.52°±0.20°.

[0026] In some embodiments, the X-ray powder diffraction pattern of ergothioneine phosphate is shown in FIG4 .

[0027] In some embodiments, the infrared spectrum of ergothioneine phosphate has the following absorption bands, expressed as the inverse of the wavelength (cm -1 )(±2cm -1 ): 3171, 3036, 1636, 1614, 1483, 1441, 1427, 1358, 1306, 1277, 1246, 1190, 1086, 993, 972, 912, 820, 785, 640, 476.

[0028] On the other hand, the present invention provides a method for preparing the salt as described above, comprising the following steps: (a) adding thioneine to an acid solution and stirring to dissolve it; (b) cooling and filtering, and beating the solution in an anhydrous alcohol solvent; and (c) drying at a certain temperature to obtain the salt.

[0029] In some embodiments, the solvent of the acid solution in step (a) is one or more of methanol, ethanol, water, and isopropanol.

[0030] In some embodiments, the acid in the acid solution in step (a) is one or more of hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, and phosphoric acid.

[0031] In some embodiments, the anhydrous alcohol solvent in step (b) is selected from one or more of the following: methanol, ethanol, and isopropanol.

[0032] In some embodiments, the filtration is performed at a temperature of 0-35°C. In some embodiments, the temperature is 10-30°C.

[0033] In some embodiments, the certain temperature is 50-100° C. In some embodiments, the temperature is 60-90° C. In some embodiments, the solution is stirred at a temperature of 50-90° C. In some embodiments, the slurry is beaten at a temperature of 50-90° C.

[0034] In some embodiments, the salt is used in the preparation of a food, beverage, supplement, nutraceutical, or cosmetic.

[0035] In another aspect, the present invention provides a composition comprising a salt as described above, and ergothioneine.

[0036] In some embodiments, the physiologically acceptable salt of ergothioneine and the composition of ergothioneine have a proportion of physiologically acceptable salt of ergothioneine greater than 55%. In some embodiments, the proportion of salt is greater than 60%, 65%, 70%, 75%, 80%, 90%, 99%.

[0037] In some embodiments, the composition further comprises a physiologically acceptable carrier.

[0038] In some embodiments, the composition is used to prepare a food, a beverage, a supplement, a nutraceutical, or a cosmetic.

[0039] Compared with the prior art, the present invention can efficiently and stably produce the salt of thioneine; and the thioneine salt of the present invention has good stability, can solve the problems such as peculiar smell, and therefore can have wide application prospects in the fields of dietary supplements, food or cosmetics. BRIEF DESCRIPTION OF THE DRAWINGS

[0040] Fig. 1 is the XRPD figure of thioneine hydrochloride of the present invention.

[0041] Fig. 2 is the XRPD figure of thioneine hydrobromide of the present invention.

[0042] Fig. 3 is the XRPD figure of thioneine sulfate of the present invention.

[0043] Fig. 4 is the XRPD figure of thioneine phosphate of the present invention.

[0044] Fig. 5 is infrared spectrum (IR) figure of thioneine hydrochloride of the present invention.

[0045] Fig. 6 is infrared spectrum (IR) figure of thioneine hydrobromide of the present invention.

[0046] Fig. 7 is an infrared spectrum (IR) figure of thioneine sulfate of the present invention.

[0047] Fig. 8 is an infrared spectrum (IR) figure of thioneine phosphate of the present invention.

[0048] Fig. 9 is the TGA figure of thioneine hydrochloride of the present invention.

[0049] FIG10 is a TGA diagram of thioneine hydrobromide of the present invention.

[0050] Figure 11 is a TGA diagram of thioneine sulfate of the present invention.

[0051] FIG12 is a TGA diagram of ergothioneine phosphate of the present invention.

[0052] Figure 13 is the DSC spectrum of thioneine hydrochloride of the present invention.

[0053] Figure 14 is the DSC spectrum of thioneine hydrobromide of the present invention.

[0054] Figure 15 is the DSC spectrum of thioneine sulfate of the present invention.

[0055] Figure 16 is a DSC spectrum of ergothioneine phosphate of the present invention.

[0056] FIG17 shows the effects of various examples on the water content of the stratum corneum.

[0057] FIG18 shows the effects of various embodiments on skin elasticity.

[0058] FIG19 shows the effects of various embodiments on head melanin. DETAILED DESCRIPTION

[0059] The preferred embodiments of the present invention will now be described in detail with reference to the embodiments thereof. Although the present invention will be described in conjunction with the preferred embodiments, it should be understood that they are not intended to limit the present invention to these embodiments. On the contrary, the present invention is intended to cover substitutions, modifications and equivalents, which may be included within the spirit and scope of the present invention as defined in the claims. In addition, in the detailed description of the present invention, many specific details are set forth in order to provide a thorough understanding of the present invention. However, it will be apparent to one of ordinary skill in the art that the present invention can be practiced without these specific details. In other cases, well-known methods, procedures, components and other features are not described in detail to avoid unnecessarily obscuring various aspects of the present invention.

[0060] As used herein, the term "or" is intended to include "and" and "or." In other words, the term "or" can also be replaced with "and / or."

[0061] As used herein, the singular forms "a," "an," and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise.

[0062] As used herein, the term "comprises" or "includes" or variations thereof refers to instances where the term is used in its non-limiting sense, meaning that items following the term are included, but items not specifically mentioned are not excluded. It also includes the more restrictive verbs 'consisting essentially of' and 'consisting of.'

[0063] As used herein, the terms "about" and "approximately" provide flexibility in numerical values ​​by providing that a given value may be "slightly higher" or "less than" an endpoint. The flexibility of this term can be determined by the specific variables and is within the knowledge of those skilled in the art to determine based on experience and the relevant description herein.

[0064] As used herein, the term "effective amount" refers to the amount required to achieve the effects taught herein. The amount to be administered may vary depending on factors such as the individual's sensitivity, age, sex, and weight, and individual idiosyncrasies. In accordance with the present disclosure, a suitable single dose size is a dose that, when administered one or more times over an appropriate period of time, achieves the effects described above.

[0065] As used herein, the term "physiologically acceptable" refers to pharmaceutically, physiologically, dietary, nutritionally, cosmeceutical and / or cosmetically acceptable, and refers to those compositions or agents, materials or combinations of compositions and / or dosage forms thereof that are within the scope of sound medical judgment, suitable for contact with human and animal tissues, compatible with other ingredients of the composition, without excessive toxicity, irritation, allergic response or other problems or complications, and commensurate with a reasonable benefit / risk ratio.

[0066] In some embodiments, the salts of the present invention can be prepared as compositions together with dietary or pharmaceutically acceptable carriers. In the present invention, the administration form of the composition is provided and involves liquid or solid fillers, diluents, excipients, solvents or encapsulating materials. Each carrier must be "acceptable" in the sense that it is compatible with the other ingredients of the composition and is harmless to the subject, i.e., suitable for consumption or nutritionally acceptable.

[0067] In some embodiments, the salts of the present invention may be administered with other supplements, such as vitamins, minerals, nootropics, and other supplements known in the art.

[0068] The following examples are illustrative of selected embodiments of the present invention and are not intended to limit the scope of the invention.

[0069] The experimental methods described in the examples are conventional methods unless otherwise specified; the reagents and materials used are commercially available unless otherwise specified.

[0070] Example 1. Preparation of thioneine hydrochloride

[0071] Ergothioneine was added to a 6 mol hydrogen chloride methanol solution, heated to 30-50 ° C, dissolved, cooled and precipitated, filtered, an equal volume of anhydrous ethanol was added, and slurried in anhydrous ethanol at 60 ° C, cooled to room temperature, filtered, and dried at 80 ° C to obtain a white solid product with a yield of 93.2%.

[0072] Example 2. Preparation of thioneine hydrobromide

[0073] 48% hydrobromic acid was added to methanol to form a hydrogen bromide solution, thioneine was added, heated to dissolve, stirred for a period of time, cooled and filtered, and slurried in anhydrous ethanol, cooled to room temperature and filtered, and dried at 80°C to obtain a white solid product with a yield of 66%.

[0074] Example 3. Preparation of thioneine hydroiodide

[0075] 57% hydroiodic acid was added to methanol to form a hydroiodic acid solution, thioneine was added, heated to dissolve, stirred for a period of time, cooled and filtered, and pulped in anhydrous ethanol, cooled to room temperature and filtered, and dried at 80°C to obtain a white solid product in a yield of 72%.

[0076] Example 4. Preparation of thioneine sulfate

[0077] 98% sulfuric acid was added to methanol to form a sulfuric acid-methanol solution, thioneine was added, heated to dissolve, stirred for a period of time, cooled and filtered, and slurried in anhydrous ethanol, cooled to room temperature and filtered, and dried at 80°C to obtain a white solid product with a yield of 90.4%.

[0078] Example 5. Preparation of ergothioneine phosphate

[0079] 85% phosphoric acid was added to methanol to form a phosphoric acid-methanol solution, thioneine was added, heated to dissolve, stirred for a period of time, cooled and filtered, and slurried in anhydrous ethanol at 60°C, cooled to room temperature and filtered, and dried at 80°C to obtain a white solid product with a yield of 87.3%.

[0080] Content determination

[0081] For the thioneine salt of each embodiment, thioneine content was measured using HPLC external standard, and acid ion content was measured using ion chromatography, and result was as shown in the table below.

[0082] The salts prepared in each example were also subjected to tests such as X-ray diffraction (XRD), differential scanning calorimetry (DSC), elemental analysis, particle size analysis, quantitative nuclear magnetic resonance (NMR), Raman spectroscopy (Raman), infrared spectroscopy (IR), TGA, IPC-MS, DVS, and acid radical content determination.

[0083] X-ray diffraction

[0084] The X-ray powder diffraction pattern was obtained using a SmartLab 3KW X-ray powder diffractometer under the following conditions: diffraction line: Cu_K-beta (40KV, 40mA), scanning rate: 20.00deg / min, scanning range: 5°~40°.

[0085] The XRPD pattern of the thioneine hydrochloride obtained in Example 1 is as shown in Figure 1, and the data are as shown in Table 1.

[0086] Table 1

[0087] The XRPD pattern of the thioneine hydrobromide obtained in Example 2 is as shown in Figure 2, and the data are as shown in Table 2.

[0088] Table 2

[0089] The XRPD pattern of the thioneine sulfate obtained in Example 4 is as shown in Figure 3, and the data are as shown in Table 3.

[0090] Table 3

[0091] The XRPD pattern of the thioneine phosphate obtained in Example 5 is shown in Figure 4, and the data are shown in Table 4.

[0092] Table 4

[0093] Infrared spectroscopy analysis

[0094] The thioneine hydrochloride of Example 1, the thioneine hydrobromide of Example 2, the thioneine sulfate of Example 4, and the thioneine phosphate of Example 5 were subjected to infrared spectroscopy analysis using a Fourier transform attenuated total reflection infrared spectrometer of Shimadzu. FIG5 is an infrared spectrum (IR) of thioneine hydrochloride. It can be seen that thioneine hydrochloride has a peak at 3136 cm -1 、3017cm -1 、2853cm -1 、2617cm - 1 、1732cm -1 、1626cm -1 、1489cm -1 、1470cm -1 、1427cm -1 、1398cm -1 、1285cm - 1 、1248cm -1 、1198cm -1 、1177cm -1 、1132cm -1 、1098cm -1 、976cm -1 、951cm -1 、912cm -1 、878cm -1、806cm -1 、737cm -1 、689cm -1 、640cm -1 , 550cm -1 、503cm - 1 446cm -1 Figure 6 is the infrared spectrum (IR) of thioneine hydrobromide. It can be seen that thioneine hydrobromide has a characteristic absorption peak at 3130 cm -1 、3028cm -1 、2963cm -1 、2891cm -1 、2766cm - 1 、1989cm -1 、1732cm -1 、1626cm -1 、1487cm -1 、1435cm -1 、1418cm -1 、1387cm - 1 、1341cm -1 、1285cm -1 、1248cm -1 、1215cm -1 、1190cm -1 、1126cm -1 、1094cm - 1 、1049cm -1 、974cm -1 、951cm -1 Figure 7 is the infrared spectrum (IR) of thioneine sulfate. It can be seen that thioneine sulfate has a characteristic absorption peak at 3142 cm -1 、3034cm -1 、2895cm -1 、1736cm -1 、1632cm -1 、1487cm -1 、1423cm -1 、1341cm -1 、1248cm -1 、1217cm -1 、1188cm -1 、1080cm -1 、1047cm -1 、1011cm -1 , 972cm-1 、951cm -1 、912cm -1 、876cm - 1 、839cm -1 、814cm -1 、739cm -1 、638cm -1 、604cm -1 、588cm -1 、552cm -1 、503cm -1 Figure 8 is the infrared spectrum (IR) of ergothioneine phosphate. It can be seen that ergothioneine phosphate has a characteristic absorption peak at 3171 cm -1 、3036cm -1 、2893cm -1 、1636cm -1 、1614cm -1 、1483cm - 1 、1441cm -1 、1427cm -1 、1358cm -1 、1306cm -1 、1277cm -1 、1246cm -1 , 1225cm - 1 、1190cm -1 、1117cm -1 、1086cm -1 , 993cm -1 , 972cm -1 、912cm -1 , 820cm -1 , 785cm -1 、746cm -1 、718cm -1 、681cm -1 、640cm -1 、556cm -1 、509cm -1 、496cm - 1 、476cm -1 、455cm -1 、436cm -1 、409cm -1 There is a characteristic absorption peak.

[0095] Thermogravimetric analysis (TGA)

[0096] Figure 9 is a TGA chart of ergothioneine hydrochloride of Example 1, which shows a 0.21% weight loss when heated from 27.2°C to 120.0°C. Figure 10 is a TGA chart of ergothioneine hydrobromide of Example 2, which shows a 5.38% weight loss when heated from 28.3°C to 100.0°C. Figure 11 is a TGA chart of ergothioneine sulfate of Example 4, which shows a 3.30% weight loss when heated from 19.4°C to 100.0°C. Figure 12 is a TGA chart of ergothioneine phosphate of Example 5, which shows a 0.12% weight loss when heated from 21.9°C to 190.0°C.

[0097] Differential Scanning Calorimetry

[0098] Differential scanning calorimetry (DSC) was performed using a TA Q2000 module with a thermal analysis controller. Data were collected and analyzed using TA Instruments Thermal Solutions software. Approximately 1-5 mg of sample was accurately weighed into a custom aluminum crucible with a lid. Samples were analyzed from 40°C to approximately 300°C using a linear heating device at 10°C / min. The DSC cell was purged with dry nitrogen during use.

[0099] Figure 13 is a DSC spectrum of thioneine hydrochloride of Example 1, including endothermic peaks at 200.36°C ± 3°C and 262.64°C ± 3°C. Figure 14 is a DSC spectrum of thioneine hydrobromide of Example 2, including endothermic peaks at 128.38°C ± 3°C and 171.57°C ± 3°C. Figure 15 is a DSC spectrum of thioneine sulfate of Example 4, including endothermic peaks at 194.24°C ± 3°C and 213.41°C ± 3°C. Figure 16 is a DSC spectrum of thioneine phosphate of Example 5, including an endothermic peak at 240.53°C ± 3°C.

[0100] Elemental analysis

[0101] With elemental analyzer, the thioneine salt of each embodiment is carried out to elemental analysis, and the elemental analysis result of salt is basically consistent with embodiment.

[0102] Anti-aging test

[0103] Above-described embodiment 1,2,3,4 and 5 are made into capsule respectively.70 healthy women aged 20-59 years old are randomly divided into seven groups, first group (G1, n=10) oral rice powder capsule is as control group, second group (G2, n=10) capsule that oral embodiment 1 is made, third group (G3, n=10) capsule that oral embodiment 2 is made, fourth group (G4, n=10) capsule that oral embodiment 3 is made, fifth group (G5, n=10) capsule that oral embodiment 4 is made, sixth group (G6, n=10) capsule that oral embodiment 5 is made, seventh group (G7, n=10) capsule that oral thioneine is made.Once a day, continue 8 weeks, respectively at week 0 and week 8, stratum corneum moisture and skin elasticity situation of experimenter's skin are measured.

[0104] As can be seen from Figures 17 and 18, the second, third, fourth, fifth, and sixth groups all increased the moisture content of the stratum corneum and improved skin elasticity. However, the seventh group was less effective in increasing the moisture content of the stratum corneum and improving skin elasticity than the first five groups.

[0105] Whitening test

[0106] Randomly select zebrafish in a 6-well plate, 15 per well. Water-soluble Examples 1, 2, 3, 4, 5 and ergothioneine were administered, and a normal control group was set up at the same time, with a volume of 3 mL per well. Incubate in the dark at 28°C for 45 hours. Ten zebrafish were randomly selected from each experimental group and photographed under a dissecting microscope. Advanced image processing software was used to analyze and collect data to determine whether they have whitening effects.

[0107] As can be seen from Figure 19, the melanin signal intensity of the zebrafish head after treatment with Examples 1, 2, 3, 4, and 5 was significantly reduced compared with the normal control group, and the effect was more obvious than that of the ergothioneine group, demonstrating that it has good whitening effect.

[0108] The thioneine salt prepared by the present invention has almost no peculiar smell of thioneine after placement, and has good adaptability and stability. In addition, the salt of thioneine of the present invention is better than thioneine in the effects of aspects such as anti-aging, whitening. Thus, the present invention solves the peculiar smell of thioneine and limits the problem of its application, and it has anti-aging, whitening effect, and can be better applied to dietary supplements, food or cosmetics field.

[0109] The above description is merely a preferred embodiment of the present invention and is not intended to limit the present invention. Any person skilled in the art may make various changes, modifications, substitutions and variations to these embodiments without departing from the principles and purpose of the present invention. The scope of the present invention is defined by the claims and their equivalents.

Claims

1. A physiologically acceptable salt of ergothioneine, characterized in that, The salt is selected from one or more of hydrochloride, hydrobromide, hydroiodide, sulfate, phosphate, hydrogen sulfate, and hydrogen phosphate.

2. The salt according to claim 1, characterized in that The molar ratio of the ergothioneine to the acid is 1:1 to 3:

1.

3. The salt according to claim 1 or 2, characterized in that The salt is in crystalline form, or amorphous form, or a mixture thereof.

4. The salt according to any one of claims 1 to 3, characterized in that The X-ray powder diffraction pattern of the thioneine hydrochloride comprises peaks at diffraction angles (2θ) of 8.18°±0.20°, 17.33°±0.20°, 20.00±0.20° and 28.67°±0.20°.

5. The salt according to claim 4, characterized in that The X-ray powder diffraction pattern of the thioneine hydrochloride also includes one or more peaks at diffraction angles (2θ) of 11.20°±0.20°, 19.10°±0.20°, 25.85°±0.20°, 13.61°±0.20°, 24.02°±0.20°, and 29.70°±0.20°.

6. The salt according to claim 4 or 5, characterized in that The X-ray powder diffraction pattern of the thioneine hydrochloride is shown in Figure 1.

7. The salt according to any one of claims 1 to 3, characterized in that The infrared spectrum of the ergothioneine hydrochloride has the following absorption bands, expressed as the reciprocal of the wavelength (cm -1 )(±2cm -1 ): 3136, 3017, 2853, 2617, 1732, 1626, 1489, 1470, 1427, 1398, 1285, 1248, 1198, 1177, 1098, 976, 951, 912, 806, 640.

8. The salt according to any one of claims 1 to 3, characterized in that The X-ray powder diffraction pattern of the ergothioneine hydrobromide comprises peaks at diffraction angles (2θ) of 11.96°±0.20°, 13.49°±0.20°, 20.77°±0.20° and 25.02°±0.20°.

9. The salt according to claim 8, characterized in that The X-ray powder diffraction pattern of the thioneine hydrobromide also includes one or more peaks at diffraction angles (2θ) of 7.52°±0.20°, 18.93°±0.20°, 28.86°±0.20°, 17.67°±0.20°, 23.48±0.20°, and 31.61°±0.20°.

10. The salt according to claim 8 or 9, characterized in that The X-ray powder diffraction pattern of the ergothioneine hydrobromide is shown in Figure 2.

11. The salt according to any one of claims 1 to 3, characterized in that The infrared spectrum of the ergothioneine hydrobromide has the following absorption bands, expressed as the reciprocal of the wavelength (cm -1 )(±2cm -1 ): 3130, 3028, 2963, 2891, 2766, 1989, 1732, 1626, 1487, 1435, 1418, 1387, 1341, 1285, 1248, 1215, 1190, 1094, 974, 951.

12. The salt according to any one of claims 1 to 3, characterized in that The X-ray powder diffraction pattern of the ergothioneine sulfate includes peaks at diffraction angles (2θ) of 13.21°±0.20°, 19.28°±0.20°, 22.52±0.20°, and 27.23°±0.20°.

13. The salt according to claim 12, characterized in that The X-ray powder diffraction pattern of the thioneine sulfate also includes one or more peaks at diffraction angles (2θ) of 9.68°±0.20°, 16.65°±0.20°, 24.60°±0.20°, 14.12°±0.20°, 21.30°±0.20°, and 30.00°±0.20°.

14. The salt according to claim 12 or 13, characterized in that The X-ray powder diffraction pattern of the thioneine sulfate is shown in Figure 3.

15. The salt according to any one of claims 1 to 3, characterized in that The infrared spectrum of the ergothioneine sulfate has the following absorption bands, expressed as the reciprocal of the wavelength (cm -1 )(±2cm -1 ): 3142, 3034, 2895, 1736, 1632, 1487, 1248, 1217, 1188, 1080, 1047, 1011, 972, 951, 912, 876, 839, 814, 604, 588.

16. The salt according to any one of claims 1 to 3, characterized in that The X-ray powder diffraction pattern of the ergothioneine phosphate includes peaks at diffraction angles (2θ) of 5.73°±0.20°, 14.96°±0.20°, 21.73±0.20° and 26.76°±0.20°.

17. The salt according to claim 16, characterized in that The X-ray powder diffraction pattern of the ergothioneine phosphate also includes one or more peaks at diffraction angles (2θ) of 11.35°±0.20°, 20.64°±0.20°, 24.34°±0.20°, 9.41°±0.20°, 18.65°±0.20°, and 28.52°±0.20°.

18. The salt according to claim 16 or 17, characterized in that The X-ray powder diffraction pattern of the ergothioneine phosphate is shown in Figure 4.

19. The salt according to any one of claims 1 to 3, characterized in that The infrared spectrum of the ergothioneine phosphate has the following absorption bands, expressed as the reciprocal of the wavelength (cm -1 )(±2cm -1 ): 3171, 3036, 1636, 1614, 1483, 1441, 1427, 1358, 1306, 1277, 1246, 1190, 1086, 993, 972, 912, 820, 785, 640, 476.

20. The salt according to any one of claims 1 to 19, characterized in that The salt is used in the preparation of food, beverages, supplements, nutritional products, and cosmetics.

21. A method for preparing the salt according to any one of claims 1 to 20, characterized in that: The method comprises the following steps: (a) adding ergothioneine into an acid solution to dissolve it; (b) cooling and filtering, and slurrying in an anhydrous alcohol solvent; and (c) drying at a certain temperature to obtain the salt.

22. The preparation method according to claim 21, characterized in that: The solvent of the acid solution in step (a) is one or more of methanol, ethanol, water and isopropanol.

23. The preparation method according to claim 21 or 22, characterized in that: The acid of the acid solution in step (a) is one or more of hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid and phosphoric acid.

24. The preparation method according to any one of claims 21 to 23, characterized in that The anhydrous alcohol solvent in step (b) is selected from one or more of the following: methanol, ethanol, and isopropanol.

25. The preparation method according to any one of claims 21 to 24, characterized in that: The certain temperature is 50-100°C.

26. A composition, characterized in that The composition comprises the salt of any one of claims 1 to 20, and ergothioneine.

27. The composition according to claim 26, characterized in that The proportion of the physiologically acceptable salt of ergothioneine is greater than 55%.

28. The composition according to claim 26 or 27, characterized in that The composition also includes a physiologically acceptable carrier.

29. The composition according to any one of claims 26 to 28, characterized in that The composition is used for preparing food, beverage, supplement, nutrition product and cosmetic.

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