L-(+)-Ergothioneine

Introduction:

English name: Ergothioneine, 2-thioimidazole amino acid

English alias: Ergot thionine, ergothioneine, etc.

Appearance: White crystalline powder

Relative molecular mass: 229.3

CAS RN: 497-30-3

EINECS number: 207-843-5

Molecular formula: C9H15N3O2S

Melting point: 275-277°C (dec.)

Density: 1.2541g/cm³

Solubility: Soluble in water.

Content: ≥99% (HPLC)

Ergothioneine is a natural antioxidant that can protect cells in the human body and is an important active substance in the body. Natural antioxidants are safe and non-toxic and have become a hot topic of research. As a natural antioxidant, ergothioneine has entered people's field of vision. It has multiple physiological functions such as scavenging free radicals, detoxification, maintaining DNA biosynthesis, normal cell growth and cell immunity.

Ergothioneine is a natural molecule isolated from the rye ergot fungus and later found in rat red blood cells, liver and many other animal tissues. Its antioxidant properties provide potential for compound treatment or can be used as a food additive or cosmetic.

Preparation method

There are three methods for preparing ergothioneine: chemical synthesis, extraction and bio-fermentation synthesis.

It is very difficult to synthesize levorotatory ergothioneine by chemical methods. Several synthesis methods have failed to achieve the expected yield due to partial or complete racemization. The difficulty of synthesis is that it is difficult to prepare the raw material 2-mercaptoimidazole, and the acidity of the α-position carbon makes the reaction easily racemized. OXIS International was the first to develop an efficient and commercial method for synthesizing ergothioneine and applied for a patent in 1995. Its method is to introduce the thiol group into the imidazole ring. However, the safety of chemically synthesized products is difficult to guarantee, the synthetic raw materials are expensive, the synthesis cost is high, and the product price is high, which limits the application of ergothioneine.

The natural biological extraction method is to extract ergothioneine from the fruiting bodies of edible fungi, pig blood, animal tissues, ergot and grains, but the content of ergothioneine in the above raw materials is still very low, and there are many impurities in the raw materials, drug residues, and high extraction costs, which limit the application of ergothioneine and are not suitable for industrialization;

The preparation of ergothioneine by biosynthesis of mushroom mycelium deep fermentation technology is the mainstream direction of low-cost large-scale production of ergothioneine. The yield of ergothioneine can be effectively improved by fermentation process control methods such as metabolic regulation, reducing production costs. More importantly, it can ensure the safety of the product and broaden the application space of ergothioneine.

Function

For substances with significant and unique biological functions of ergothioneine, scholars from various countries have long studied its application. Although it needs to be further deepened, it has played a good role in inspiring its application in various fields. Ergothioneine has a wide range of uses and market prospects in organ transplantation, cell preservation, medicine, food and beverage, functional food, animal feed, cosmetics and biotechnology.

1. Used as a unique antioxidant

Ergothioneine is a natural antioxidant that is highly protective and non-toxic to cells. It is not easily oxidized in water, which allows them to reach a concentration of mmol in certain tissues and stimulate the natural antioxidant defense system of cells. Among the many antioxidants, ergothioneine is particularly unique because it can chelate heavy metal ions and protect red blood cells in the body from free radical damage.

2. Used in organ transplantation

The amount and time of existing tissue preservation play a decisive role in the success of organ transplantation surgery. The most commonly used antioxidant in organ transplantation is glutathione. When it is exposed to the environment, it is easily oxidized. Even in a refrigerated or liquid environment, its antioxidant capacity is greatly reduced, which is toxic to cells and produces inflammation, inducing tissue protein hydrolysis. Ergothioneine is just like an antioxidant that is stable in aqueous solution and can chelate heavy metal ions. It can be used as a substitute for glutathione in the field of organ protection to better protect transplanted organs.

3. Add to cosmetics as a skin protectant

Ultraviolet rays UVA in sunlight can penetrate into the dermis of human skin, affect the growth of epidermal cells, cause surface cells to die, and cause premature aging of the skin, while ultraviolet rays UVB are more likely to cause skin cancer. Ergothioneine can minimize the formation of reactive oxygen species and protect cells from radiation damage, so ergothioneine can be added to certain cosmetics as a skin protectant for the development of outdoor skin care products and protective cosmetics.

4. Application in ophthalmology

Studies have found that ergothioneine plays a key role in protecting the eyes, so many researchers hope to develop an ophthalmic product to promote the development of ophthalmic treatment surgery. Ophthalmic surgery is generally performed locally, and the water solubility and stability of ergothioneine provide feasibility for such surgery and have great application value.

5. Application in other areas

Due to its excellent performance, ergothioneine can be applied to many fields. For example, it can be used in the fields of medicine, food, health care products, and cosmetics. In the medical field, it can be used to treat inflammation, etc., and can be made into tablets, capsules, oral preparations, etc.; in the field of health products, it can prevent the occurrence of cancer, etc., and can be made into functional foods, functional drinks and other products; in the field of cosmetics, it can be used for anti-aging, and can be made into sunscreens and other products.

As people's health awareness increases, the excellent properties of ergothioneine as a natural antioxidant will gradually be widely recognized and applied by people.