Ethionine

Title: Ethionine
CAS Registry Number: 13073-35-3
CAS Name: S-Ethyl-L-homocysteine
Additional Names: 2-amino-4-(ethylthio)butyric acid; a-amino-g-(ethylmercapto)butyric acid; homocysteine S-ethyl ether
Molecular Formula: C6H13NO2S
Molecular Weight: 163.24
Percent Composition: C 44.15%, H 8.03%, N 8.58%, O 19.60%, S 19.64%
Line Formula: CH3CH2SCH2CH2CH(NH2)COOH
Literature References: Prepn from ethanethiol and acrolein, purification via Zn salt: Norton, US 2840587 (1958 to Dow). Prepn of DL-form and L-form: Armstrong, Lewis, J. Org. Chem. 16, 749 (1951). Resolution of D- and L-isomers: Greenstein et al., J. Biol. Chem. 204, 307 (1953). Review: E. Farber, "Ethionine Carcinogenesis" in A. Haddow, S. Weinhouse, Advan. Cancer Res. vol. 7 (Academic Press, New York, 1963) pp 383-474.
Properties: Crystals, dec 272-274°. [a]D24 +25.1°. Also reported as [a]D23 +20.1° (1N HCl) (Armstrong, Lewis).
Optical Rotation: [a]D24 +25.1°; [a]D23 +20.1° (1N HCl) (Armstrong, Lewis)
Derivative Type: DL-Form
CAS Registry Number: 67-21-0
Properties: Crystals, dec 257-260°. Also reported as dec 272-284° (Armstrong, Lewis).
Ethiozin Ethiprole Ethirimol Ethisterone Ethofumesate

Ethionine
Ethionine.png
Identifiers
CAS number 13073-35-3 YesY
PubChem 6205
ChemSpider 5970 YesY
ChEBI CHEBI:4886 N
ChEMBL CHEMBL203187 N
Jmol-3D images Image 1
Properties
Molecular formula C6H13NO2S
Molar mass 163.239 g/mol
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Ethionine is a non-proteinogenic amino acid structurally related to methionine, with an ethyl group in place of the methyl group.

Ethionine is an antimetabolite and methionine antagonist. It prevents amino acid incorporation into proteins and interferes with cellular use of adenosine triphosphate (ATP). Because of these pharmacological effects, ethionine is highly toxic and is a potent carcinogen.[1]