13073-35-3

Basic information

• Product 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+%
• CAS NO: 13073-35-3
• Molecular Formula: C₆H₁₃NO₂S
• Molecular Weight: 163.24
• EINECS: 235-966-4
• Product Categories: Amino Acids;Amino Acids 13C, 2H, 15N;Amino acids methyl、ethyl、t-butyl series;Amino Acids & Derivatives;Sulfur & Selenium Compounds
• Mol File: 13073-35-3.mol
• Article Data: 8

Chemical Properties

• Melting Point: 280 °C (dec.)(lit.)
• Boiling Point: 310.391 °C at 760 mmHg
• Flash Point: 141.519 °C
• Appearance: /solid
• Density: 1.085 (estimate)
• Vapor Pressure: 0.000133mmHg at 25°C
• Refractive Index: 22 ° (C=1, 1mol/L HCl)
• Storage Temp.: -20°C Freezer
• Solubility: Aqueous Acid (Slightly), Water (Slightly)
• PKA: 2.23±0.10(Predicted)
• Merck: 14,3738
• CAS DataBase Reference: L-ETHIONINE(CAS DataBase Reference)
• NIST Chemistry Reference: L-ETHIONINE(13073-35-3)
• EPA Substance Registry System: L-ETHIONINE(13073-35-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• RTECS: ES6825300
• Hazardous Substances Data: 13073-35-3(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

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

Definition

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

Purification Methods

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.]

InChI:InChI=1/C6H13NO2S/c1-2-10-4-3-5(7)6(8)9/h5H,2-4,7H2,1H3,(H,8,9)/t5-/m0/s1

Upstream product

• 7689-60-3 S-benzyl-L-homocysteine 
• 75-08-1 ethanethiol 
• 5394-22-9 L-3,6-bis(2-chloroethyl)-2,5-diketopiperazine 
• 57271-88-2 N-acetyl-rac-ethionine 
• 294856-83-0 DL-N-benzoylethionine 
• 126872-00-2 N-formyl-D,L-ethionine 
• 626-72-2 L-homocystine 
• 75-03-6 ethyl iodide 
• 67-21-0 ethionine 
• 7540-67-2 O-acetyl-L-homoserine 

Downstream Products

• 524-70-9 S-adenosyl-L-ethionine 
• 108329-74-4 Boc-(D)Ethionine 
• 88389-34-8 N-(2-Benzyl-3-Mercaptopropionyl)-L-Ethionine 
• 26892-00-2 (S)-S-adenosylethionine 
• 5135-31-9 5'-deoxy-5'-(ethylthio)adenosine 
• 63640-45-9 ethionine sulfoxide 
• 89-50-9 2-(ethylamino)benzoic acid 
• 1374669-68-7 N-(((9H-fluoren-9-yl)oxy)carbonyl)-S-ethyl-L-homocysteine 
• 1460-34-0 3-methyl-2-oxopentanoic acid 
• 1821-02-9 2-oxopentanoic acid 
• 115369-98-7 (S)-2-((S)-2-Acetylsulfanylmethyl-3-phenyl-propionylamino)-4-ethylsulfanyl-butyric acid ethyl ester 
• 115369-97-6 (S)-2-((R)-2-Acetylsulfanylmethyl-3-phenyl-propionylamino)-4-ethylsulfanyl-butyric acid ethyl ester 
• 15785-31-6 (R_SS_C)-ethionine sulfoxide 
• 15785-31-6 (S_SS_C)-ethionine sulfoxide 

Related news

Effect of L-ETHIONINE (cas 13073-35-3) on macromolecular synthesis in mitogen-stimulated lymphocytes09/29/2019

2–4 mM l-ethionine completely inhibits DNA synthesis in phytohaemagglutinin- or concanavalin A-stimulated lymphocytes even though it does not prevent the morphological changes characteristic of blast formation. Evidence is presented which indicates that complete commitment to DNA synthesis as w...detailed

In vivo31P NMR studies of the hepatic response to L-ETHIONINE (cas 13073-35-3) in anesthetized rats10/01/2019

Phosphorus-31 surface coil spectroscopy has been used to study the effects of l-ethionine administration on the hepatic metabolism of the anesthetized Sprague-Dawley rat. ATP levels were found to decrease by ∼30% 3 to 4 hr after administration of 1 mg/g body wt of l-ethionine to the anesthetize...detailed

Effect of L-ETHIONINE (cas 13073-35-3) the expression of the SOS system in Escherichia coli09/27/2019

The effect of L-ethionine, the ethyl analog of the essential amino acid methionine the SOS system of Escherichia coli was studied. This compound does not induce either inhibition of cell division nor cessation of cell respiration in a RecA+ Met+ RelA+ strain, nor in RecA+ Met− RelA+ or RecA+ Met...detailed

Acute lethality of D- and L-ETHIONINE (cas 13073-35-3) in Swiss mice09/26/2019

SummaryThe acute, 7-day LD50 in Swiss mice of D-ethionine administered intraperitoneally, was determined as 185 mg/kg with 95% confidence limits of 163 and 210 mg/kg. L-ethionine, the stereoisomer, which is more potent in inhibiting liver RNA synthesis, was not lethal at 2500 mg/kg. This acute t...detailed

Short communicationMutagenic effect of L-ETHIONINE (cas 13073-35-3) in soybean and maize☆09/25/2019

The mutagenic effect of l-ethionine in plants was examined using heterozygotic soybean and maize. Seeds were soaked in solutions of different concentration and the mutational frequency increment was measured by the increase of mutant sectors on the leaf. l-ethionine has a mutagenic effect in pla...detailed

Biochemical and developmental features of experimental phenylketonuria induced by L-ETHIONINE (cas 13073-35-3) in suckling rats09/24/2019

Suckling rats were injected subcutaneously with doses of l-ethionine (0.1 μmole/g body wt and 0.5 μmole/g body wt) at intervals of 12 hr. In the latter group, phenylalanine hydroxylase was effectively inhibited in vivo resulting in hyperphenylalaninemia and phenylketonuria. Due to the well-kno...detailed

Relevant articles and documents

Amidohydrolase Process: Expanding the use of l-N-carbamoylase/N-succinyl- amino acid racemase tandem for the production of different optically pure l-amino acids

A bienzymatic system comprising an N-succinylamino acid racemase from Geobacillus kaustophilus CECT4264 (GkNSAAR) and an enantiospecific l-N-carbamoylase from Geobacillus stearothermophilus CECT43 (BsLcar) has been developed. This biocatalyst has been able to produce optically pure natural and non-natural l-amino acids starting from racemic mixtures of N-acetyl-, N-formyl- and N-carbamoyl-amino acids by dynamic kinetic resolution. The fastest conversion rate was found with N-formyl-amino acids, followed by N-carbamoyl- and N-acetyl-amino acids, and GkNSAAR proved to be the limiting step of the system due to its lower specific activity. Metal ion cobalt was essential for the activity of the biocatalyst and the system was optimally active when Co 2+ was added directly to the reaction mixture. The optimum pH for the biocatalyst proved to be 8.0, for both N-formyl- and N-carbamoyl-amino acid substrates, whereas optimum temperature ranges were 45-55 °C for N-formyl-amino acids and 55-70 °C for N-carbamoyl-derivatives. The bienzymatic system was equally efficient in converting aromatic and aliphatic substrates. Total conversion was also achieved using high substrate concentrations (100 and 500 mM) with no noticeable inhibition. This "Amidohydrolase Process" enables the production of both natural and non-natural l-amino acids from a broad substrate spectrum with yields of over 95%.

Synthesis of non-natural cofactor analogs of S-adenosyl-L-methionine using methionine adenosyltransferase

The present disclosure relates to the synthesis of non-natural analogs of S-adenosyl-L-methionine (SAM) and/or of Se-adenosyl-L-methionine (SeAM) by reacting a methionine analog and adenosine triphosphate (ATP) in the presence of at least one methionine adenosyltransferase (MAT), and to use thereof with downstream SAM and/or SeAM utilizing enzymes. The non-natural analogs of SAM and/or SeAM have the general formula: where X is S or Se, and R1 is an alkyl group.

Beauveria bassiana ATCC 7159 contains an L-specific α-amino acid benzamidase

Biotransformation of a series of racemic N-benzoyl α-amino acids by the fungus Beauveria bassiana ATCC 7159 results in isolation of the corresponding D-amino acid benzamides in high enantiomeric purity and yield.