Ethionine

Structural formula
Simplified structural formula of ethionine without stereochemistry
General
Surname	Ethionine
other names	2-amino-4- (ethylthio) butyric acid 3-ethyl homocysteine
Molecular formula	C 6 H 13 NO 2 S
Brief description	beige solid
External identifiers / databases
CAS number 67-21-0 ( racemate ) EC number 200-647-0 ECHA InfoCard 100,000,588 PubChem 6205 ChemSpider 5970 Wikidata Q27137089
properties
Molar mass	163.24 g mol −1
Physical state	firmly
density	1.151 g cm −3
Melting point	269 ° C (decomposition)
Refractive index	1,550
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 315-319-335 P: 261-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Ethionine is a chemical compound from the group of non-proteinogenic amino acids . It is the ethyl analog of the proteinogenic amino acid methionine .

Stereochemistry

Ethionine has a stereocenter, so there are two enantiomers . If the name ethionine is not identified by a descriptor , the racemate , a 1: 1 mixture of ( S ) -ethionine and ( R ) -ethionine, is meant.

Enantiomers of ethionine
Surname	( S ) -ethionine	( R ) -ethionine
Structural formula
other names	L- ethionine (+) - ethionine	D -ethionine (-) - ethionine
CAS number	13073-35-3	535-32-0
EC number	235-966-4	208-612-1
ECHA info card	100,032,682	100.007.831
PubChem	25674	92124
Wikidata	Q5403506	Q27137090
Melting point	280 ° C (decomposition)	278 ° C (decomposition)

Extraction and presentation

Ethionine can be obtained by reacting ethanethiol with acrolein followed by treatment with hydrogen cyanide and ammonia and hydrolysis.

properties

Ethionine is a beige solid. It blocks important intracellular functions of methionine and is sometimes incorporated into proteins instead of methionine . When ingested , it induces fatty liver disease , acute intestinal inflammation and liver carcinoma .

use

( RS ) -Ethionine is used to induce oxidative stress in the liver and to study the level and activities of anti-oxidative enzymes and compounds such as glutathione . ( RS ) -Ethionine is used to accelerate the development of bile duct carcinomas in vivo .

Individual evidence

1. ↑ ^{a b c d e f g} data sheet DL-Ethionine, ≥95% (TLC) from Sigma-Aldrich , accessed on February 20, 2016 ( PDF ).
2. ^ ^{A b} Carl L. Yaws: The Yaws Handbook of Physical Properties for Hydrocarbons and Chemicals Physical Properties for More Than 54,000 Organic and Inorganic Chemical Compounds, Coverage for C1 to C100 Organics and Ac to Zr Inorganics . Gulf Professional Publishing, 2015, ISBN 978-0-12-801146-1 , pp. 125 ( limited preview in Google Book Search).
3. ↑ Hans-Dieter Jakubke, Hans Jeschkeit: amino acids, peptides, proteins , Verlag Chemie, Weinheim, pp. 27-28, 1982, ISBN 3-527-25892-2 .
4. ↑ Data sheet L-Ethionine, ≥99% (TLC) from Sigma-Aldrich , accessed on February 20, 2016 ( PDF ).
5. ↑ Data sheet D-Ethionine, 98% from Sigma-Aldrich , accessed on February 20, 2016 ( PDF ).
6. ^ Entry on (L) -ETHIONINE in the Hazardous Substances Data Bank , accessed on February 21, 2016.
7. ↑ Entry on ethionine. In: Römpp Online . Georg Thieme Verlag, accessed on February 21, 2016.