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Home > Encyclopedia > D-Ethionine

D-Ethionine

D-Ethionine structure

D-Ethionine 

structure
  • CAS No:

    535-32-0

  • Formula:

    C6H13NO2S

  • Chemical Name:

    D-Ethionine

  • Synonyms:

    D-Homocysteine,S-ethyl-;Butyric acid,2-amino-4-(ethylthio)-,D-;S-Ethyl-D-homocysteine;D-Ethionine;NSC 97927;(R)-2-Amino-4-(ethylthio)butanoic acid;(2R)-2-Amino-4-(ethylsulfanyl)butanoic acid

  • Categories:

    Biochemical Engineering  >  Amino Acids and Derivatives

Description

White Crystalline Solid


D-ethionine is an S-ethylhomocysteine that has R-configuration at the chiral centre. It is an enantiomer of a L-ethionine.

D-Ethionine Basic Attributes

163.24

163.24

208-612-1

91GB0NN2T6

2930909090

Characteristics

88.6

0.90

white powder.

1.2±0.1 g/cm3

278 °C (decomp)

310.4±37.0 °C at 760 mmHg

141.5±26.5 °C

1.524

-20°C Freezer

Specific optical rotation: -21 deg at 22 °C (c=1, 1N HCl)

Safety Information

NONH for all modes of transport

3

36/37/38

26

ES6825100

Xi

P261-P305 + P351 + P338

H315-H319-H335

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

ACUTE TOXICITY IN MICE OF D-ETHIONINE WAS SUPPRESSED BY L-METHIONINE AND ADENINE.|DL-METHIONINE @ 0.6-0.8% IN DIET FED SIMULTANEOUSLY WITH ETHIONINE PREVENTS DEVELOPMENT OF LIVER TUMORS /IN RATS/.|IN RATS...LABELLING IN VIVO OF LIVER PROTEINS BY TRITIATED DIMETHYLNITROSAMINE WAS...LARGELY INHIBITED BY...ETHIONINE...|...TUMOR OF THE IRIS HAS BEEN OBSERVED IN RATS' EYES AFTER REPEATED SYSTEMIC ADMIN IN COMBINATION WITH N-2-FLUORENYLACETAMIDE.

Drug Information

THE QUANTITATIVE STUDY OF THE INVERSION OF D-ETHIONINE INTO L-ETHIONINE IN VIVO, MEASURED IN THE LIVER OF RATS BY THE FORMATION OF S-ADENOSYLETHIONINE FROM L-ETHIONINE, DEMONSTRATES HIGH EFFICIENCY OF THIS CONVERSION WHEN LOWER DOSES OF D-ETHIONINE ARE USED. AT HIGHER DOSES (MORE THAN 25 MG (80 UMOL)/100 G BODY WT), ACCUMULATION OF S-ADENOSYLETHIONINE IS RETARDED. THIS DECR OF S-ADENOSYLETHIONINE FORMATION MAY BE DUE TO AN UNKNOWN EFFECT OF D-ETHIONINE ON THE L-ETHIONINE METABOLISM.

RATS FED 0.25% DL-ETHIONINE FOR 3 DAYS SHOWED ELEVATED TRNA METHYLTRANSFERASE & INHIBITED GLYCINE METHYLTRANSFERASE LEVELS IN THE LIVER. THESE CHANGES PERSIST THROUGHOUT THE CARCINOGENIC REGIME & SIMILAR TRENDS WERE OBSERVED IN ETHIONINE-INDUCED LIVER TUMORS. D-ETHIONINE WAS EQUALLY EFFECTIVE IN ELEVATING TRNA METHYLTRANSFERASE IN THE LIVER, IN BOTH MALE & FEMALE RATS.|/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.

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/

D-Ethionine Use and Manufacturing

Methods of Manufacturing

Prepared from ethanethiol and acrolein, purification via Zn salt: Norton, US Patent 2,840,587 (1958 to Dow) /Ethionine/

Uses

An Amino Acid derivative.

Production

(1992) No data

FOLIAR SPRAYS OF D-ETHIONINE LOWER THE INCIDENCE OF POTATO COMMON SCAB.

The following methods have been developed for the analysis of free amino acids in blood, 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/

Computed Properties

Molecular Weight:163.24
XLogP3:-1.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:5
Exact Mass:163.06669983
Monoisotopic Mass:163.06669983
Topological Polar Surface Area:88.6
Heavy Atom Count:10
Complexity:108
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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