(S)-[1-carboxy-2-(2-mercaptoimidazol-4-yl)ethyl]trimethylammonium hydroxide
Ergothioneine
CAS: 497-30-3
Molecular Formula: C9H15N3O2S
(S)-[1-carboxy-2-(2-mercaptoimidazol-4-yl)ethyl]trimethylammonium hydroxide - Names and Identifiers
(S)-[1-carboxy-2-(2-mercaptoimidazol-4-yl)ethyl]trimethylammonium hydroxide - Physico-chemical Properties
| Molecular Formula | C9H15N3O2S |
| Molar Mass | 229.3 |
| Density | 1.2541 (rough estimate) |
| Melting Point | 275-277°C (dec.) |
| Solubility | Soluble in water (50 mg/ml), acetone, hot ethanol, and methanol. |
| Appearance | White solid. |
| Color | White or off-white |
| PH | +47^o (c=1 in water) |
| Storage Condition | -20°C |
| Stability | Stable for 1 year from date of purchase as supplied. Solutions in water may be stored at -20°C for no more then 1 day. |
| Refractive Index | 1.6740 (estimate) |
| MDL | MFCD00167474 |
(S)-[1-carboxy-2-(2-mercaptoimidazol-4-yl)ethyl]trimethylammonium hydroxide - Risk and Safety
| WGK Germany | 3 |
(S)-[1-carboxy-2-(2-mercaptoimidazol-4-yl)ethyl]trimethylammonium hydroxide - Reference
| Reference Show more | 1. Hengqiang Zhao, Minmin Zhang, Qian Liu, Xiaoli Wang, Ruixuan Zhao, Yanling Geng, Tityee Wong, Shengbo Li & Xiao Wang (2018) A comprehensive screening shows that ergothioneine is the most abundant antioxidant in the wild macrofungus Phylloporia ribis Ryvard 2. Hengqiang Zhao, Minmin Zhang, Qian Liu, Xiaoli Wang, Ruixuan Zhao, Yanling Geng, Tityee Wong, Shengbo Li & Xiao Wang (2018) A comprehensive screening shows that ergothioneine is the most abundant antioxidant in the wild macrofungus Phylloporia ribis Ryvard 3. [IF=9.783] Wan-Ju Sun et al."Characterization and engineering control of the effects of reactive oxygen species on the conversion of sterols to steroid synthons in Mycobacterium neoaurum."Metab Eng. 2019 Dec;56:97 4. [IF=3.463] Xiaochen Qian et al."Inhibition of browning and shelf life extension of button mushroom (Agaricus bisporus) by ergothioneine treatment."Sci Hortic-Amsterdam. 2021 Oct;288:110385 5. [IF=3.167] Lan Pang et al."Protective role of ergothioneine isolated from Pleurotus ostreatus against dextran sulfate sodium-induced ulcerative colitis in rat model."Journal Of Food Science. 2021 Dec 06 |
(S)-[1-carboxy-2-(2-mercaptoimidazol-4-yl)ethyl]trimethylammonium hydroxide - Reference Information
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Introduction | ergothionine is a natural antioxidant, which can protect cells in the human body, is an important active substance in the body. Natural antioxidants are safe and non-toxic, and have become a research hotspot. As a natural antioxidant, ergothionine has come into people's field of vision. It has many physiological functions, such as scavenging free radicals, detoxification, maintaining DNA biosynthesis, normal growth of cells and cellular immunity. Ergothionein 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 may provide potential for complex therapy, or as a food additive or cosmetic. |
| Use | L-ergothionein is a natural molecule isolated from the rye ergot fungus, later found in rat erythrocytes and liver, as well as in many other animal tissues. Its antioxidant properties may provide the therapeutic potential of the compound, or it may be used as a food additive or cosmetic. |
| distribution range | ergothionein is distributed in some tissues and organs of mammals, mainly in red blood cells (about 1~2 mmol.L) and in the semen of some animals, although no experimental studies have shown that animals can synthesize the substance, but there must be a way to absorb and retain ergothio in animal cells. For predators, ergothionein in animal tissues can supply dietary needs. A study by Melville.D.B and Eich. S[1] found that ergothionein was also present in cereals. |
| biological effects | ergothioneine is a powerful hypochlorous acid scavenger (HOCl), although many compounds can react with hypochlorous acid, few can react as rapidly as ergosulfide. a 1-anti-protease inhibitors (APIs), such as elastase, are particularly sensitive to hypochlorous acid, and physiological concentrations of ergothio are very effective in protecting APIs, against the inactivation induced by hypochlorous acid, since neutrophils are the main source of hypochlorous acid in the body, one of the roles of ergothionein is to protect red blood cells from the harm of neutrophils from normal functioning or pathological sites of inflammation. |
| Application | ergothionine in organ transplantation, cell preservation, medicine, food and beverage, functional food, animal feed, cosmetics and biotechnology and other fields have a wide range of uses and market prospects. used as a unique antioxidant: ergothionine is a highly protective and non-toxic natural antioxidant for cells, which is not easily oxidized in water, this allows their concentration in certain tissues to reach mmol, and stimulates the natural antioxidant defense system of cells. Among many antioxidants, ergothionein is especially unique, because ergothionein can chelate heavy metal ions, which can protect red blood cells from free radical damage. |
| biological activity | Ergothioneine is an imidazole-2-thione derivative of histidine betaine, it is synthesized by certain bacteria and fungi. Ergothioneine is generally considered an antioxidant. |
Last Update：2024-04-09 02:00:09
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