L-(+)-Ergothioneine - Moligand™, ≥98% , CAS No.497-30-3

CAS: 497-30-3 Cat. No.: L134175 Peso molecular: 229.30 Número EC: 207-843-5

GRADE & PURITY Moligand™, ≥98%

Synonyms

2-mercaptohistidine trimethylbetaine | AKOS027325505 | ergothioneine (thione form) | ERGOTHIONEINE [MI] | SCHEMBL188140 | 1H-Imidazole-4-ethaniminium, alpha-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-, hydroxide, inner salt, (S)- | MFCD00167474 | (S)-3-

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Descripción general

Ergothioneine is a stable antioxidant that can be found under conditions of excessive oxidative stress in plant and animal tissue. Ergothioneine can scavenge free radicals and protect cells from UV-induced ROS with higher efficiency than antioxidants coenzyme Q(10) or idebenone. The compound could be a non-toxic thiol buffering antioxidant, enhance cell viability induced by hydrogen peroxide (H2O2), and inhibit DNA oxidation by peroxynitrite (ONOO-) in the human neuronal hybridoma cell line (N-18-RE-105).
An antioxidant and free radical scavenger

Application：

L - (+) - ergot sulfur is suitable for studying its reactivity with 2,2 '- and 4,4' - bipyridine disulfides (2-Py-S-S-2-Py and 4-Py-S-S-4-Py). 

It can also be used for the incubation of experimental cells and for in vitro kinase activity measurement of ATM (Ataxia telangiectasia mutation) or ATR (ATM - and RAD3- related).

L - (+) - ergot has been used to: 

1. As a component of the cumulus oocyte complex (COC) maturation medium, its protective effect on lipid peroxidation formation was tested; 

2. As an antioxidant compound, it is used to detect type 2 diabetes patients; 

3. As a positive control for soluble carrier protein 22A4 (SLC22A4) transport detection.

Specifications

Sinónimos

2-mercaptohistidine trimethylbetaine | AKOS027325505 | ergothioneine (thione form) | ERGOTHIONEINE [MI] | SCHEMBL188140 | 1H-Imidazole-4-ethaniminium, alpha-carboxy-2, 3-dihydro-N, N, N-trimethyl-2-thioxo-, hydroxide, inner salt, (S)- | MFCD00167474 | (S)-3-

Especificaciones y pureza

Moligand™, ≥98%

Mecanismos bioquímicos y fisiológicos

L - (+) - ergothione (ET) has the highest concentration in oxidative stress tissues, and the highest concentration in blood, lens, bone marrow, semen, and liver. It is an antioxidant that prevents cell apoptosis by clearing reactive oxygen species and nit

Condiciones de almacenamiento de almacenamiento

Store at -20°C

Enviado en

Ice chest + Ice pads

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Grado

Moligand™

Tipo de acción

INHIBITOR

Pureza

≥98%

Nombres e identificadores

• Pubchem Sid: 488195377
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488195377
• Sonrisas canónicas: C[N+](C)(C)C(CC1=CNC(=S)N1)C(=O)[O-]
• IUPAC Name: (2S)-3-(2-sulfanylidene-1,3-dihydroimidazol-4-yl)-2-(trimethylazaniumyl)propanoate
• InChIKey: SSISHJJTAXXQAX-ZETCQYMHSA-N
• 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
• Isómeros SMILES: C[N+](C)(C)[C@@H](CC1=CNC(=S)N1)C(=O)[O-]
• WGK Alemania: 3
• Peso molecular: 229.30
• Reaxy-Rn: 3910838
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=3910838&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Clase Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives
            • Level7 Histidine and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Clase: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives - Alpha amino acids and derivatives
• Direct Parent: Histidine and derivatives
• Alternative Parents: L-alpha-amino acids Imidazolyl carboxylic acids and derivatives Aralkylamines Imidazolethiones Tetraalkylammonium salts Heteroaromatic compounds Thioureas Carboxylic acid salts Azacyclic compounds Carboxylic acids Monocarboxylic acids and derivatives Organopnictogen compounds Organic salts Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Histidine or derivatives - Alpha-amino acid - L-alpha-amino acid - Imidazolyl carboxylic acid derivative - Aralkylamine - Imidazole-2-thione - Azole - Imidazole - Quaternary ammonium salt - Heteroaromatic compound - Tetraalkylammonium salt - Thiourea - Carboxylic acid salt - Organoheterocyclic compound - Azacycle - Carboxylic acid - Monocarboxylic acid or derivatives - Hydrocarbon derivative - Organonitrogen compound - Organooxygen compound - Organopnictogen compound - Organic oxygen compound - Amine - Organosulfur compound - Organic oxide - Organic salt - Organic nitrogen compound - Carbonyl group - Aromatic heteromonocyclic compound
• Descripción: This compound belongs to the class of organic compounds known as histidine and derivatives. These are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
• External Descriptors: amino-acid betaine - L-histidine derivative

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Objetivos asociados (no humanos)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: Soluble in water (50 mg/ml), acetone, hot ethanol, and methanol.
• Punto de fusión (°C): 255 - 259 °C
• Peso molecular: 229.300 g/mol
• XLogP3: 0.300
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 229.088 Da
• Monoisotopic Mass: 229.088 Da
• Topological Polar Surface Area: 96.300 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 314.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Referencias

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4. Chaoqun Tang, Lu Zhang, Junyi Wang, Congjia Zou, Yalin Zhang, Jifeng Yuan.  (2024)  Engineering Saccharomyces boulardii for Probiotic Supplementation of l-Ergothioneine.  Biotechnology Journal,  19  (11): (e202400527).  [PMID:39562168] [10.1002/biot.202400527]

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6. Yu-Zhen Li, Qi Wang, Cheng Cheng, Chao Chen, Feng-Li Zhang, Yue Zou, Jun Li, Xin-Qing Zhao.  (2025)  Genome mining of an endophytic natural yeast isolate Rhodotorula sp. Y090 and production of the antioxidant ergothioneine.  JOURNAL OF BIOTECHNOLOGY,      [PMID:40169100] [10.1016/j.jbiotec.2025.03.019]

7. Bohan Zhang, Qingling Nie, Xin Yan, Qiaojun Jiang, Junjie Ren, Peipei Xu, Dechan Lu, Ruiyun You, Lizhi Li, Yudong Lu.  (2024)  Machine learning-based SERS label-free detection of plasma and exosome binding in early-stage lung cancer.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2024.111306]

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10. Jiaxin Peng, Jing Chen, Mengran Wu, Tao He, Xiaojuan Guo, Qiangguo Ao, Ling Chen.  (2025)  Proteomic analysis reveals the potential mechanism of ergothioneine in preventing acute kidney injury to chronic kidney disease transition.  ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS,      [PMID:40633826] [10.1016/j.abb.2025.110534]

11. Yamiao Li, Jingxin Rao, Zhentao Jiang, Xinyi Zhang, Qiang Zhu, Caokai Zhu, Wenli Yu, Xin Dong, Shanshan Gao, Wenchi Zhang, Liang Lin, Mingyue Zheng, Rongzhen Zhang.  (2025)  AI-driven engineering of EgtD enabling high-efficiency ergothioneine synthesis with a multi-enzyme cascade.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:40889650] [10.1016/j.ijbiomac.2025.147266]

12. Wen Gao, Yang Wang, Fuhao Wang, Xinni Wu, Fuping Lu, Fufeng Liu.  (2024)  Ergothioneine exerts neuroprotective effects in Parkinson’s disease: Targeting α-synuclein aggregation and oxidative stress.  FOOD RESEARCH INTERNATIONAL,      [PMID:39849723] [10.1016/j.foodres.2024.115590]

13. Lei Chen, Zhuomin Zhang, Zihan Guan, Jing Sun, Yanhui Sun, Mengmeng Xu, Ka-Hing Wong, Guiyang Shi, Zhongyang Ding.  (2025)  Enhanced ergothioneine production in Pleurotus tuber-regium through submerged fermentation optimization and selenium-driven mechanistic insights.  Food Bioscience,      [PMID:] [10.1016/j.fbio.2025.106146]

14. Zhen Guo, Yiwen Huang, Xiaowei Wang, Yi Han, Ang Li, Yiyang Qu, Lin Chen, Meihang Du, Yiming Zhang, Yuanzhi Xu.  (2025)  Ergothioneine alleviates osteoporosis via the ROS-MAPK signaling Axis.  BONE,      [PMID:40287031] [10.1016/j.bone.2025.117496]

15. Shuzhen Chen, Wenjing Lin, Yan Zhang, Fan Cai, Wei Lin, Jianbin Xiao, Xingtong Chen, Qin Li, Huaidong Zhang, Mingliang Zhang, Li Li.  (2025)  Enhancing ergothioneine production in Saccharomyces cerevisiae via protein fusion technology and gene integration optimization.  Food Bioscience,      [PMID:] [10.1016/j.fbio.2025.106745]

16. Han Wang, Meiling Tai, Wanzhao Li, Yawen Li, Zhimeng Zhang, Dongli Zhang, Lishe Gan, Junhao Li, Xiaojuan Song, Honghong Qiu, Manmei Li, Heyun Zhang, Zhong Liu.  (2025)  Ganoderma lucidum extract reduces skin aging by reducing mitochondrial stress and controlling mitochondrial numbers.  FITOTERAPIA,      [PMID:40381851] [10.1016/j.fitote.2025.106627]

17. Qiuni Long, Hua Huang, Xinshuai Zhang.  (2025)  In vitro characterization of the ergothioneine oxidative catabolic pathway in Actinoplanes missouriensis ATCC 14538.  BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS,      [PMID:40480087] [10.1016/j.bbrc.2025.152144]

18. Wang Lihong, Tian Xueqin, Xue Pinghong, Deng Yunhong, Gao Rui, Hu Zhihong.  (2025)  Enhanced production of ergothioneine in Aspergillus oryzae.  APPLIED MICROBIOLOGY AND BIOTECHNOLOGY,  109  (1): (1-11).  [PMID:40493205] [10.1007/s00253-025-13505-2]

19. Jiahuan Ling, Rui Chen, Minghai Wang, Chun-Xiao Yan, Ruomu Xia, Lihui Zhang.  (2025)  Integrating Membrane Permeability Engineering and Enzyme Design for Efficient Production of Ergothioneine in E. coli.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:40478902] [10.1021/acs.jafc.5c02834]

20. Liang Li, Shanshan Xu, Yanjun Jiang.  (2025)  Efficient production of Ergothioneine via an optimized allogenous assembly of the ERG synthesis pathway in Escherichia coli BL21.  JOURNAL OF BIOTECHNOLOGY,      [PMID:40523433] [10.1016/j.jbiotec.2025.06.009]

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22. Yong Li, Jingyu Liu, Junlong Meng, Cuiping Feng, Jie Chen, Maomao Zeng, Hua Li.  (2025)  Assessment of the correlations among 1,2-dicarbonyl compounds, advanced glycation end products, and raw material chemical components of fried shiitake mushroom (Lentinula edodes) crisps.  Food Chemistry-X,      [PMID:41112183] [10.1016/j.fochx.2025.103128]