L-(+)-Ergothioneine CAS#: 497-30-3; ChemWhat Code: 1411088
Identification
| Product Name | L-(+)-Ergothioneine |
| IUPAC Name | (2S)-3-(2-sulfanylidene-1,3-dihydroimidazol-4-yl)-2-(trimethylazaniumyl)propanoate |
| Molecular Structure |  |
| CAS Registry Number | 497-30-3 |
| EINECS Number | 207-843-5 |
| MDL Number | MFCD00167474 |
| Beilstein Registry Number | 105692 |
| Synonyms | ERGOTHIONEINE L-(+)-Ergothioneine 497-30-3 L-Ergothioneine Sympectothion Ergothionine l-Thioneine Thiolhistidine-betaine Thioneine (S)-3-(2-Thioxo-2,3-dihydro-1H-imidazol-4-yl)-2-(trimethylammonio)propanoate BDZ3DQM98W 58511-63-0 L(+)-Ergothioneine Thiasine (2S)-3-(2-sulfanylidene-1,3-dihydroimidazol-4-yl)-2-(trimethylazaniumyl)propanoate (S)-(1-Carboxy-2-(2-mercaptoimidazol-4-yl)ethyl)trimethylammonium hydroxide UNII-BDZ3DQM98W erythrothioneine L-Ergothionine ergothioneine thiol ergothioneine thione NSC 7175 thiolhistidinebetaine EINECS 207-843-5 MFCD00167474 Ergothioneine L-(+) ergothioneine thione form AI3-23492 ERGOTHIONEINE [MI] ergothioneine (thione form) ERGOTHIONEINE [INCI] SCHEMBL188140 CHEBI:4828 SCHEMBL9985141 CHEBI:82707 DTXSID901020082 HMS2089D04 2-mercaptohistidine trimethylbetaine HY-N1914 CCG-207908 1H-Imidazole-4-ethanaminium, .alpha.-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-, inner salt, (.alpha.S)- 1H-Imidazole-4-ethanaminium, alpha-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-, inner salt, (S)- CS-0018211 D83035 AB01275464-01 |
| Molecular Formula | C9H15N3O2S |
| Molecular Weight | 229.30 |
| 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 |
| InChI Key | SSISHJJTAXXQAX-ZETCQYMHSA-N |
| Canonical SMILES | C[N+](C)(C)C(CC1=CNC(=S)N1)C(=O)[O-] |
Physical Data
| Appearance | White to light yellow |
Spectra
| Description (NMR Spectroscopy) | Nucleus (NMR Spectroscopy) | Solvents (NMR Spectroscopy) |
| Spectrum | 1H | D2O |
| Spin-spin coupling constants | D2O |
Route of Synthesis (ROS)
| Conditions | Yield |
| With hydrogen; triethylamine In ethanol; water at 110℃; under 30003 Torr; for 24h; Autoclave; |
Safety and Hazards
| Pictogram(s) |  |
| Signal | Warning |
| GHS Hazard Statements | H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation] H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation] |
| Precautionary Statement Codes | P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (The corresponding statement to each P-code can be found at the GHS Classification page.) |
Other Data
| Transportation | Class 6.1; Packaging Group: II; UN Number: 2671 |
| HS Code | |
| Storage | Preserve in tight containers， Store at a temperature – 20土5℃ |
| Shelf Life | 2 years |
| Druglikeness | |
| Lipinski rules component | |
| Molecular Weight | 229.303 |
| logP | -0.918 |
| HBA | 4 |
| HBD | 1 |
| Matching Lipinski Rules | 4 |
| Veber rules component | |
| Polar Surface Area (PSA) | 107.61 |
| Rotatable Bond (RotB) | 4 |
| Matching Veber Rules | 2 |
| Quantitative Results | ||
| 1 of 72 | Comment (Pharmacological Data) | Bioactivities present |
| Reference | Current Patent Assignee: OXIS INTERNATIONAL INC – WO2003/99277, 2003, A1 | |
| 2 of 72 | Comment (Pharmacological Data) | Bioactivities present |
| Reference | Functional effects of protein sequence polymorphisms in the organic cation/ergothioneine transporter OCTN1 (SLC22A4) | |
| 3 of 72 | Comment (Pharmacological Data) | Bioactivities present |
| Reference | Isolation and determination of histidine and related compounds |
| Use Pattern |
| L-(+)-Ergothioneine CAS#: 497-30-3 is a rare natural chiral amino acid, which has unique cell functions such as scavenging free radicals, detoxification, maintaining DNA biosynthesis, normal cell growth, cellular immunity, anti-radiation, whitening and anti-aging. Physiological protection function. Ergothioneine has broad application prospects in industries such as food, cosmetics, functional food and bio-medicine, and was included in the EU’s new resource food list in 2018. |
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