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L-ETHIONINE

L-ETHIONINE structure

L-ETHIONINE 

structure
  • CAS No:

    13073-35-3

  • Formula:

    C6H13NO2S

  • Chemical Name:

    L-ETHIONINE

  • Synonyms:

    s-ethyl-homocystein;s-ethyl-l-homocystein;L-ETHIONINE;L-2-AMINO-4-(ETHYLTHIO)BUTYRIC ACID;H-ETH-OH;S-ethyl-L-homocysteine;L -ETHIONINE 99%;L-ETHIONINE 98+%

  • Categories:

    Organic Chemistry  >  Nitrogen Compounds

Description

L-ethionine is an S-ethylhomocysteine that has S-configuration at the chiral centre. It has a role as an antimetabolite and a carcinogenic agent. It is an enantiomer of a D-ethionine.|2-Amino-4-(ethylthio)butyric acid. An antimetabolite and methionine antagonist that interferes with amino acid incorporation into proteins and with cellular ATP utilization. It also produces liver neoplasms.


White Solid


ChEBI: An S-ethylhomocysteine that has S-configuration at the chiral centre.


Likely impurities are N-acetyl-(R and S)-ethionine, S-methionine, and R-ethionine. Crystallise it from water by adding 4volumes of EtOH or 85% aqueous EtOH. It sublimes at 196-216o/0.3mm with 99.1% recovery and unracemised [Gross & Gradsky J Am Chem Soc 77 1678 1955]. [Weiss & Stekol J Am Chem Soc 73 2399 1951, Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 pp 2658, 2659 1961, Beilstein 4 IV 3194.]

L-ETHIONINE Basic Attributes

163.24

163.24

235-966-4

WX1BN24WZT

TSCA listed

DTXSID5020578

White to Off-White

2930.90.4950

Characteristics

1.085 (estimate)

280 °C (dec.)(lit.)

310.4±37.0 °C(Predicted)

22 ° (C=1, 1mol/L HCl)

rat,LD,intraperitoneal,> 1gm/kg (1000mg/kg),LIVER: OTHER CHANGESLIVER: CHANGES IN LIVER WEIGHT,Acta Pathologica Japonica. Vol. 39, Pg. 281, 1989.

DECOMP @ 257-260 DEG /DL-FORM/|CRYSTALS, /DL-FORM & L-FORM/|DECOMP @ 272-274 °C

Keep in dark place,Sealed in dry,2-8°C

Safety Information

3

Xi

26

ES6825300

36/37/38

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

DL-METHIONINE @ 0.6-0.8% IN DIET FED SIMULTANEOUSLY WITH ETHIONINE PREVENTS DEVELOPMENT OF LIVER TUMORS /IN RATS/. /ETHIONINE/|IN RATS...LABELLING IN VIVO OF LIVER PROTEINS BY TRITIATED DIMETHYLNITROSAMINE WAS...LARGELY INHIBITED BY...ETHIONINE... /ETHIONINE/|...TUMOR OF THE IRIS HAS BEEN OBSERVED IN RATS' EYES AFTER REPEATED SYSTEMIC ADMIN IN COMBINATION WITH N-2-FLUORENYLACETAMIDE.|The effects of SA3443, a novel disulfide cmpd on acute liver injuries induced by carbon tetrachloride, D-galactosamine and DL-ethionine were studied in rats or mice. SA3443 (100-300 mg/kg, po) significantly suppressed the incr of serum transaminase activity and liver triglyceride content in the carbon tetrachloride or DL-ethionine induced model. ...

Drug Information

3 (?). 3= MODERATELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 0.5-5 G/KG, BETWEEN 1 OUNCE & 1 PINT (OR 1 LB) FOR 70 KG PERSON (150 LB).

Drugs that are chemically similar to naturally occurring metabolites, but differ enough to interfere with normal metabolic pathways. (From AMA Drug Evaluations Annual, 1994, p2033) (See all compounds classified as Antimetabolites.)

IN RAT KIDNEY RADIOACTIVITY WAS MAINLY LOCALIZED IN MEDULLA FOLLOWING INJECTION WITH (14)C-ETHIONINE, WHEREAS (14)C-METHIONINE WAS HOMOGENEOUSLY DISTRIBUTED THROUGHOUT WHOLE PARENCHYMA IN RATS.

S-ADENOSYLETHIONINE IS A SUGGESTED ALKYLATING METABOLITE OF CARCINOGEN ETHIONINE. /FROM TABLE/|ETHIONINE IS BIOACTIVATED IN LIVER TO S-ADENOSYL-L-ETHIONINE, WHICH CAN ETHYLATE MACROMOLECULES CAUSING CELL ABNORMALITIES. ADENOSYLETHIONINE IS CHEM STABLE & CAN PENETRATE TO EMBRYONIC TISSUES & CAUSE TERATOGENIC EFFECTS.|IN URINE OF TREATED RATS, 4 PRINCIPAL ETHIONINE EXCRETORY PRODUCTS WERE IDENTIFIED...N-ACETYLETHIONINE SULFOXIDE, S-ADENOSYLETHIONINE, ETHIONINE SULFOXIDE, & FREE ETHIONINE.

/ETHIONINE/ INHIBITS THE INCORPORATION OF METHIONINE AND GLYCINE INTO RAT PROTEIN IN VIVO AND THE CONVERSION OF METHIONINE INTO CYSTEINE. ETHIONINE IS DEETHYLATED, AND THE ETHYL GROUP APPEARS IN ANALOGUES OF METABOLITES KNOWN TO PARTICIPATE IN TRANSMETHYLATION REACTIONS, EG ETHYL CHOLINE. IN THE RAT IT IS ITSELF INCORPORATED INTO ABNORMAL PROTEINS COMPETITIVELY, BUT ITS AFFINITY IS ONLY 1/600 THAT OF METHIONINE. /ETHIONINE/|... The mechanism by which ethionine induces fatty liver is thought to be due to the inhibition of synthesis of very low density lipoprotein. ... The synthesis of lipoprotein is correlated with liver estradiol receptor concn, /an examination/ of the effect of ethionine on estradiol receptor concn in rat liver /was examined/. Estradiol receptor concn in both cytosolic and nuclear fractions were greatly decr by a single injection of ethionine at a dose of 0.5 mg/kg bw. In particular, the decr in nuclear receptor concn was observed a few hr after the injection and correlated with the decr in triglyceride content in the very low density lipoprotein fraction. /Data suggests/ that liver estradiol receptor is involved in the pathogenesis of ethionine induced fatty liver of rats.

L-METHIONINE IS ANTAGONISTIC TO THE EFFECTS OF ETHIONINE.

WHEN GIVEN ORALLY TO SMALL SERIES OF PATIENTS WITH FAR ADVANCED NEOPLASIAS IN DOSES OF 0.67 TO 45 G/DAY (TOTAL DOSES 9.7 TO 55 G), ETHIONINE PRODUCED THE FOLLOWING SYMPTOMS WHEN THE DIET WAS DEFICIENT IN METHIONINE: IMPAIRMENT OF LIVER FUNCTION, PROTEINURIA, HEMATURIA, DERMATITIS, LEUKOPENIA, THROMBOCYTOPENIA AND DIARRHEA. DETERIORATION OF MENTAL STATUS & FRANK TOXIC PSYCHOSIS ... ALSO OCCURRED.|These agents /including ethionine/ cause hepatic damage by interfering with essential metabolic pathways, which leads to cytotoxic (necrosis or steatosis) and/or cholestatic (biliary stasis) injury patterns. /Ethionine/

Ethionine

L-ETHIONINE Use and Manufacturing

Methods of Manufacturing

REACTION OF ETHANETHIOL WITH ACROLEIN FOLLOWED BY TREATMENT WITH HYDROGEN CYANIDE & AMMONIA AND HYDROLYSIS|...FROM ETHANETHIOL & ACROLEIN, PURIFICATION VIA ZN SALT: NORTON US PATENT 2,840,587 (1958 TO DOW). PREPN OF DL-...& L-FORM: ARMSTRONG, LEWIS, J ORG CHEM 16, 749 (1951).

Uses

EXPTL CARCINOGEN|BIOLOGICAL RESEARCH CHEMICAL


Ethionine-induced inhibition of protein synthesis and lowering of ATP level in the liver.

Production

(1977) NOT PRODUCED COMMERCIALLY IN US|(1979) NOT PRODUCED COMMERCIALLY IN US|(1992) No data

L-Homocysteine, S-ethyl-: INACTIVE|.../ETHIONINE/ WAS SYNTHESIZED AS AN ANTIMETABOLITE TO L-METHIONINE & USED IN STUDY OF TRANSMETHYLATION REACTIONS IN RELATION TO THE BIOCHEMISTRY OF THIS ESSENTIAL AMINO ACID.|ETHIONINE...THE TOXIC ANALOGUE OF AMINO ACID METHIONINE, IS PRODUCED BY E COLI & VARIOUS OTHER MICROORGANISMS.

The following methods have been developed for the analysis of free amino acids in food and feedstocks: (1) Protein hydrolysis, (2) Chromatographic methods that include high performance liquid chromatography (HPLC), gas chromatography (GC) and thin-layer chromatography (TLC), (3) Colorimetric and Fluorimetric Analysis, (4) Spectrometric Analysis, and (5) Enzymatic Determination and Microbial Assay /Amino acids/

The following methods have been developed for the analysis of free amino acids in blood: (1) Protein hydrolysis, (2) Chromatographic methods that include high performance liquid chromatography (HPLC), gas chromatography (GC) and thin-layer chromatography (TLC), (3) Colorimetric and Fluorimetric Analysis, (4) Spectrometric Analysis, and (5) Enzymatic Determination and Microbial Assay /Amino acids/

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