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Ergothioneine information


Ergothioneine
Names
Preferred IUPAC name
(2S)-3-(2-Sulfanylidene-2,3-dihydro-1H-imidazol-4-yl)-2-(trimethylazaniumyl)propanoate
Other names
L-Ergothioneine; (+)-Ergothioneine; Thiasine; Sympectothion; Ergothionine; Erythrothioneine; Thiolhistidinebetaine
Identifiers
CAS Number
  • 497-30-3 checkY
3D model (JSmol)
  • Interactive image
  • Interactive image
ChEBI
  • CHEBI:4828 checkY
ChemSpider
  • 4508619 checkY
ECHA InfoCard 100.007.131 Edit this at Wikidata
KEGG
  • C05570 ☒N
PubChem CID
  • 5351619
UNII
  • BDZ3DQM98W checkY
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 checkY
    Key: SSISHJJTAXXQAX-ZETCQYMHSA-N checkY
  • 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
    Key: SSISHJJTAXXQAX-ZETCQYMHBA
SMILES
  • C[N+](C)(C)C(CC1=CNC(=S)N1)C(=O)[O-]
  • S=C1N\C(=C/N1)C[C@@H](C([O-])=O)[N+](C)(C)C
Properties
Chemical formula
C9H15N3O2S
Molar mass 229.30 g/mol
Appearance white solid
Melting point 275 to 277 °C (527 to 531 °F; 548 to 550 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Ergothioneine is a naturally occurring amino acid and is a thiourea derivative of histidine, containing a sulfur atom on the imidazole ring.[1] This compound occurs in relatively few organisms, notably actinomycetota, cyanobacteria, and certain fungi.[2][3] Ergothioneine was discovered by Charles Tanret in 1909 and named after the ergot fungus from which it was first purified,[4] with its structure being determined in 1911.[5][6]

In humans, ergothioneine is acquired exclusively through the diet and accumulates in erythrocytes, bone marrow, liver, kidney, seminal fluid, and eyes.[7] Although the effect of ergothioneine in vivo is under preliminary research, its physiological role in humans is unknown.[7] Ergothioneine is sold as a dietary supplement.[8]

  1. ^ "Ergothioneine". PubChem, National Center for Biotechnology Information, US National Library of Medicine. 2 November 2019. Retrieved 7 November 2019.
  2. ^ Fahey RC (2001). "Novel thiols of prokaryotes". Annual Review of Microbiology. 55: 333–56. doi:10.1146/annurev.micro.55.1.333. PMID 11544359.
  3. ^ Pfeiffer C, Bauer T, Surek B, Schömig E, Gründemann D (2011). "Cyanobacteria produce high levels of ergothioneine". Food Chemistry. 129 (4): 1766–1769. doi:10.1016/j.foodchem.2011.06.047.
  4. ^ Tanret, C. (1909). "Sur une base nouvelle retirée du seigle ergoté : l'ergothioneine". Comptes rendus hebdomadaires des séances de l'Académie des sciences (in French). 149: 222-224.
  5. ^ Barger, G.; Erwins, A.J. (1911). "The constitution of ergothioneine : a betaine related to histidine". Journal of the Chemical Society. Transactions. 99: 2336–2341.
  6. ^ Cite error: The named reference Mann was invoked but never defined (see the help page).
  7. ^ a b Cheah, Irwin K.; Halliwell, Barry (2021-01-26). "Ergothioneine, recent developments". Redox Biology. 42: 101868. doi:10.1016/j.redox.2021.101868. ISSN 2213-2317. PMC 8113028. PMID 33558182.
  8. ^ Cite error: The named reference efsa was invoked but never defined (see the help page).

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Ergothioneine

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Lincomycin

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amino acid and the amino-octose bound to ergothioneine is then the substrate of LmbV, which substitute ergothioneine by mycothiol. The mycothiol moiety is...

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Pleurotus citrinopileatus

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had the highest amount of ergothioneine among the other saprotrophs within the group. List of Pleurotus species Ergothioneine Singer, R. (1943). "Das System...

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SLC22A4

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known as SLC22A4, is a human gene; the encoded protein is known as the ergothioneine transporter. The encoded protein is an integral protein of the plasma...

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Selenoneine

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Selenoneine is a selenium containing ergothioneine derivative where the selenium (Se) atom replaces a sulfur atom. It can be systematically named as (2-selenyl-Nα...

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Histidine

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Neurospora crassa, histidine can be converted into the antioxidant ergothioneine. The Food and Nutrition Board (FNB) of the U.S. Institute of Medicine...

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Boletus edulis

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phytochemicals, including 500 mg of ergosterol per 100 g of dried mushroom, and ergothioneine. The fruit bodies contain numerous polyphenols, especially a high content...

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List of human blood components

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after 15 min rest 3.1-9.5 ×10−11 when emitted 3.8 ×10−9 2-2.5 ×10−9 Ergothioneine 1-20 ×10−5 Erythrocytes (#/cm3) adult male, avg. (range) 5.2 (4.6-6...

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Organic cation transport protein

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norepinephrine, MPP+ SLC22A4 Solute carrier family 22 member 4 Sodium ion and ergothioneine SLC22A5 Solute carrier family 22 member 5 Primary carnitine deficiency...

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mutation was selected for, a mutation which probably arose to deal with ergothioneine deficiency but increases the risk of ulcerative colitis, coeliac disease...

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Linsidomine

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PMID 16237680. Jang JH, Aruoma OI, Jen LS, Chung HY, Surh YJ (February 2004). "Ergothioneine rescues PC12 cells from beta-amyloid-induced apoptotic death". Free...

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Ophthalmic acid

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the crucial glutathione synthesis pathway supports the production of ergothioneine and ophthalmate". Molecular Microbiology. 100 (1): 15–24. doi:10.1111/mmi...

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Streptomyces spinoverrucosus

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"Spithioneines A and B, Two New Bohemamine Derivatives Possessing Ergothioneine Moiety from a Marine-Derived". Organic Letters. 17 (12): 3046–3049....

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ETT

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respiratory medicine Epithelioid trophoblastic tumour, a very rare cancer Ergothioneine transporter, a protein and human gene (SLC22A4) Exercise Tolerance Test...

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Life Length

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of Cryopreserved CGMP-compliant Human Induced Pluripotent Stem Cells Ergothioneine Mitigates Telomere Shortening under Oxidative Stress Conditions Effect...

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Fungal isolate

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compounds codinaeopsin, efrapeptins, and antiamoebin. The fungal isolate ergothioneine is actively absorbed and concentrated by the human body via SLC22A4...

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Tylopilus plumbeoviolaceus

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22-dien-3β-ol, uridine, allitol, ergosterol, ergosterol 5α,8α-peroside, ergothioneine, adenosine, and uracil have been identified from the mushrooms. List...

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Major facilitator superfamily

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carnitine to TEA is 1.78. A key substrate of this transporter seems to be ergothioneine (ET). Rheumatoid arthritis SLC16A11 Q8NCK7 Proton-linked monocarboxylate...

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National Academy of Science and Technology Awards

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Encarnacion, Ph.D. Bureau of Fisheries and Aquatic Resources Application of ergothioneine-rich extract from an edible mushroom (Flammulina velutipes) for melanosis...

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