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| CAS No.: | 497-30-3 |
|---|---|
| Name: | Ergothioneine |
| Molecular Structure: | |
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| Formula: | C9H15N3O2S |
| Molecular Weight: | 229.303 |
| Synonyms: | 1H-Imidazole-4-ethanaminium,a-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-,inner salt, (aS)-;1H-Imidazole-4-ethanaminium,a-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-,hydroxide, inner salt, (S)-;Ammonium,[1-carboxy-2-(2-mercaptoimidazol-4-yl)ethyl]trimethyl-, hydroxide, inner salt,L-(+)- (8CI);1H-Imidazole-4-ethanaminium, a-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-, innersalt, (S)-;2-Mercapto-N,N-dimethylhistidine methyl ester betaine;2-Mercaptohistidine betaine;2-Mercaptohistidine trimethylbetaine; |
| EINECS: | 207-843-5 |
| Density: | 1.2541 (rough estimate) |
| Melting Point: | 275-277 °C (dec.) |
| Appearance: | White solid |
| PSA: | 100.97000 |
| LogP: | 0.77420 |
| Conditions | Yield |
|---|---|
| Stage #1: potassium thiocyanate; C8H16N2O3 In water at 85 - 90℃; Stage #2: With hydrogenchloride In ethanol; water at 30℃; Reagent/catalyst; | 1.1 g |
ergothioneine
L-ergothioneine disulfide
| Conditions | Yield |
|---|---|
| With formic acid; copper(II) sulfate at 25℃; for 0.5h; |
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The CAS register number of L-(+)-Ergothioneine is 497-30-3. It also can be called as 2-Mercaptohistidine trimethylbetaine and the IUPAC name about this chemical is 3-(2-sulfanylidene-1,3-dihydroimidazol-4-yl)-2-(trimethylazaniumyl)propanoate. The molecular formula about this chemical is C9H15N3O2S and the molecular weight is 229.30. It belongs to the following product categories which include Intermediates & Fine Chemicals; Pharmaceuticals; Sulfur & Selenium Compounds and so on. This chemical is a natural molecule isolated from the rye ergot fungus and later identified in rat erythrocytes and liver and in numerous other animal tissues. Its antioxidizing properties may afford the compound therapeutic potential.
Physical properties about L-(+)-Ergothioneine are: (1)ACD/LogP: -3.07; (2)ACD/LogD (pH 5.5): -2.47; (3)ACD/LogD (pH 7.4): -2.47; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 2.03; (7)ACD/KOC (pH 7.4): 2.03; (8)#H bond acceptors: 5; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 4; (11)Polar Surface Area: 75.87 Å2.
| Data Type | Description / Results | Source / Reference |
| Highest ergothioneine content in mushrooms | Golden oyster mushroom: up to 11,800 mg/kg dwt (cultivated in grape marc) | Tian et al., 2023 (Table 1) doi:10.1017/S0007114522003592 |
| Fermented foods with high ergothioneine | Fermented shiitake with Pediococcus pentosaceus: 1775.2 mg/kg wwt | Tian et al., 2023 (Table 1) doi:10.1017/S0007114522003592 |
| Supplementation in humans | 7-day oral administration (5 or 25 mg/day); resulted in large plasma increases, minimal urinary excretion (<4%) | Cheah et al., cited in Tian et al., 2023 doi:10.1017/S0007114522003592 |
| Supplementation in mice | 70 mg/kg/day for 28 days; high accumulation in liver and blood, moderate in kidney and brain | Tang et al., 2018; Halliwell et al., 2018 |
| Ergothioneine blood levels | Human whole blood: ~125 µM; Mouse: ~220 µM; millimolar in RBCs | Halliwell et al., 2018 doi:10.1002/1873-3468.13123 |
| Metabolites measured | Hercynine, S-methyl-ergothioneine (correlate with ET levels); ergothioneine sulfonate near detection limit | Tian et al., 2023 doi:10.1017/S0007114522003592 |
| Absorption transporter | SLC22A4 (also known as OCTN1); high specificity for ergothioneine | Grundemann et al., 2005; cited in all three papers |
| Transporter knockout models | Mice with SLC22A4 knockout: liver ET reduced from 121 ± 25 to <2.13 µg/g; higher oxidative stress | Tian et al., 2023; Halliwell et al., 2018 |
| ET in breast milk and cerebrospinal fluid | Breast milk: 5–150 nM; CSF: ~250 nM | Halliwell et al., 2018 doi:10.1002/1873-3468.13123 |
| Neuroprotective effects in humans | Lower plasma ET associated with cognitive decline, Parkinson's, and mild cognitive impairment | Halliwell et al., 2018 doi:10.1002/1873-3468.13123 |
You can still convert the following datas into molecular structure:
(1)SMILES: S=C1N\C(=C/N1)C[C@@H](C([O-])=O)[N+](C)(C)C
(2)InChI: InChI=1/C9H15N3O2S/c1-12(2,3)7(8(13)14)4-6-5-10-9(15)11-6/h5,7H,4H2,1-3H3,(H2-,10,11,13,14,15)/t7-/m0/s1
(3)InChIKey: SSISHJJTAXXQAX-ZETCQYMHBA
(4)Std. InChI: InChI=1S/C9H15N3O2S/c1-12(2,3)7(8(13)14)4-6-5-10-9(15)11-6/h5,7H,4H2,1-3H3,(H2-,10,11,13,14,15)/t7-/m0/s1
(5)Std. InChIKey: SSISHJJTAXXQAX-ZETCQYMHSA-N
