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D-Ethionine

HCID 92124
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
535-32-0
Standard SMILES
CCSCC[C@@H](N)C(=O)O
InChIKey
GGLZPLKKBSSKCX-RXMQYKEDSA-N
Molecular formula
C6H13NO2S
Average molar mass
163.24 g/mol
Monoisotopic mass
163.06669983

Overview

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

Names & identifiers

Preferred name
D-Ethionine
IUPAC
(2R)-2-amino-4-ethylsulfanylbutanoic acid
English name
D-Ethionine
Molecular formula
C6H13NO2S
Molecular weight
163.24

Names & synonyms

D-Ethionines-ethyl-d-homocysteine(D)-ETHIONINE(-)-ethionineD-2-Amino-4-(ethylthio)butyric acidEthionine, D-D-S-ethylhomocysteine(-)-S-ethyl-D-homocysteineHSDB 3570D-EthiononeEINECS 208-612-1UNII-91GB0NN2T6
Show more names
H-D-ETH-OHd-butyricaciD(-)-ETHIONINED-ETHIONINE 98%D-Ethionine,98%D-EthylhomocysteineD-ETHIONINE USP/EP/BP
(2R)-2-amino-4-(ethylsulfanyl)butanoic acidNSC 97927BRN 1722527D-2-amino-4-(ethylthio)butanoic acidCHEBI:686634-04-00-03194 (Beilstein Handbook Reference)NSC-97927DEthionine

Database identifiers

CAS
535-32-0
PubChem CID
92124
DTXSID
DTXSID801021499
ChEBI
CHEBI:68663
UNII
91GB0NN2T6
EC Number
208-612-1
Nikkaji
J9.245B

Properties

Computed structural properties

XLogP
-1.5
Topological polar surface area
88.6 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
4
Rotatable bonds
5
Heavy atoms
10
Formal charge
0
Complexity
108

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Other Organic Compounds
Melting Point278 °C, decomposes
Optical RotationSpecific optical rotation: -21 deg at 22 °C (c=1, 1N HCl)
Physical DescriptionWhite flakes; [MSDSonline]

Physicochemical properties

Melting point
278 °C · 278 °C (dec.)(lit.)
Boiling point
310.4 · 310.4±37.0 °C(Predicted)
Density
1.085 · 1.085 (estimate)
refractive index
1.55 · 1.5500 (estimate)
storage temp.
-20 °C · -20°C Freezer
solubility
Aqueous Acid (Slightly), Methanol (Slightly), Water (Slightly)
form
solid
pka
2.23 · 2.23±0.10(Predicted)
color
White
optical activity
22 · [α]22/D 21°, c = 1 in 1 M HCl
CAS DataBase Reference
535 · 535-32-0(CAS DataBase Reference)
FDA UNII
91 GB0NN2T6 · 91GB0NN2T6
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
315 · H315-H319-H335
Precautionary statements
261 · P261-P305+P351+P338
Hazard Codes
Xi
Risk Statements
36 · 36/37/38
Safety Statements
26 · 26
WGK Germany
3 · 3
RTECS
6825100 · ES6825100
Hazardous Substances Data
535 · 535-32-0(Hazardous Substances Data)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazards SummaryCauses changes to the blood after intraperitoneal administration with an LD50 of 185 mg/kg; [RTECS] Causes liver injury by interfering with metabolic pathways; [HSDB] An irritant; Targets the liver; [MSDSonline]
Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety & protection

Disposal Methods · 1 item

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.

Toxicology

Interactions · 4 items

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.

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Human Toxicity ExcerptsThese 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/
Non-Human Toxicity Excerpts · 5 items

DL-ETHIONINE INDUCED HEPATIC CARCINOMAS IN MALE RATS FED FOR 16-20 MONTHS AS 0.1% OF A 16% CASEIN, CHOLINE-SUPPLEMENTED DIET. 50% OF FEMALE MICE FED 0.1% OF DL-ETHIONINE IN THE SAME DIET DEVELOPED HEPATOMAS BY 18 MONTHS; MALE MICE WERE LESS SUSCEPTIBLE. /D,L-ETHIONINE/

Varying amounts of DL-, L-, D-ethionine were admin iv to sheep, either as a continuous infusion, usually over 2 days, or as a single injection. Groups of sucking mice and rats in their first cycle of hair growth, were given sc injections of DL-ethionine at several dose rates. Ethionine was a potent inhibitor of wool growth in sheep; the L- and D-isomers appeared equally effective. An infusion of 20 mg/kg DL-ethionine ... given at the daily rate of 10 mg/kg for 2 days, or an injection of 40 mg/kg DL-ethionine ... were sufficient to cause the growth of very weak wool and allow the fleece to be readily removed by hand within 3 wk after dosing. The inhibition of wool growth was usually associated with a concn of ethionine in blood plasma, during iv infusion, of 10 umol/l or higher. An infusion of DL-ethionine at a daily rate of 1 mg/kg for 12 days caused the growth of weak fibers and substantially reduced both length growth rate and diameter of fibers. The toxicity of ethionine to sheep was dependent on the total dose and the duration of administration. An infusion of 40 mg/kg (20 mg/kg/day for 2 days) produced severe effects, but the sheep recovered; a dose of 14 mg/kg (2 mg/kg for 7 days) was lethal. ... Doses of DL-ethionine as high as 460 mg/kg failed to cause hair loss is sucking mice. While body growth was severely retarded at this dose, no deaths occurred. ... DL-ethionine failed to cause hair loss in sucking rats, but was lethal to some rats at a dose of 360 mg/kg.

OPTIMAL INDUCTION OF /RAT/ LIVER TUMORS REQUIRES CONTINUOUS FEEDING OF SYNTHETIC DL-ETHIONINE (0.25% IN DIET) FOR...5 MO. ... THOUGH ETHIONINE CAUSES ACUTE DEGENERATIVE LESIONS IN PANCREATIC ACINI & PREVENTS ALLOXAN DIABETES, NO PANCREATIC TUMORS...REPORTED. /DL-FORM/

CHEM TERATOGENS THAT REQUIRE METAB OR BIOACTIVATION TO ELECTROPHILIC REACTANTS INCL...ETHIONINE... MOST FREQUENTLY IT IS LIVER THAT PRODUCES VARIETY OF ELECTROPHILIC REACTANTS THAT, LIKE ALKYLATING AGENTS, COVALENTLY BIND TO MACROMOLECULES.

For more Non-Human Toxicity Excerpts (Complete) data for (D)-ETHIONINE (8 total), please visit the HSDB record page.

Safety data

wgk
3
rtecs
ES6825100
risk_code
36/37/38
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi
safety_code
26
Hazard statements
H315-H319-H335
Precautionary statements
P261-P305+P351+P338
Hazardous Substances Data
535-32-0(Hazardous Substances Data)

Chemistry & industry

Pharmacology

Mechanism of Action · 2 items

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.

Metabolism/Metabolites · 1 item

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.

Uses & manufacturing

Uses · 2 items

Used as a foliar spray to lower the incidence of potato common scab; [HSDB]

Farming (Pesticides) [Category: Industry]

U.S. Production(1992) No data
Methods of ManufacturingPrepared from ethanethiol and acrolein, purification via Zn salt: Norton, US Patent 2,840,587 (1958 to Dow) /Ethionine/
General Manufacturing InformationFOLIAR SPRAYS OF D-ETHIONINE LOWER THE INCIDENCE OF POTATO COMMON SCAB.

Applications

UsesAn Amino Acid derivative.

Suppliers35 total

北京华美互利生物化工010-56205725 · [email protected]
阿诺西(上海)生物技术有限公司400-1107768 15058188853 · [email protected]
河南赢创生物科技有限公司16650615803 · [email protected]
南京世洲生物科技有限公司025-025-85560043 17301488900 · [email protected]
浙江珲达生物科技有限公司0571-89903022 18679456698 · [email protected]
郑州鸿晟医药科技有限公司0371-55695890 15637198702 · [email protected]
上海康恩博科技有限公司(科小研试剂)400-1388-521 17673770086 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
梯希爱(上海)化工贸易有限公司021-61109150 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
山东西亚化学有限公司13355009207 13355009207 · [email protected]
南京德尔诺医药科技有限公司02585057128;025-86957866 13952093866 · [email protected]
上海湄水化工科技有限公司021-60549325 18616193163
陕西缔都医药化工有限公司029-81024372 17792795018 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
艾吉析科技(上海)有限公司17717235263 17717235263 · [email protected]
石家庄瑞田生化有限公司15831127780 · [email protected]
武汉福鑫化工有限公司+86-2759207851; +86-18007136271 · [email protected]
嘉兴市浙嘉生物科技有限公司0573-85609002 · [email protected]
成都华纯科技有限公司400-1166-196 15982826727 · [email protected]
山东小野化学股份有限公司0539-6362799 20)
厦门盈融达化工有限公司+86-0592-6210733 · [email protected]
career henan chemical co+86-0371-86658258 · [email protected]
深圳聚合生化科技有限公司+86-400-002-6226 13028896684 · [email protected]
江苏洪珉药业有限公司18221292452 · [email protected]
上海皓鸿生物医药科技有限公司400-8210725 4008210725 · [email protected]
四川嘉瑛莱科技有限责任公司028-64159575 · [email protected]
上海研邦医药科技有限公司15618536883 · [email protected]
重庆卡兰医药有限公司[email protected]
北京百灵威科技有限公司18210857532 18210857532 · [email protected]
DAYANG CHEM (HANGZHOU) CO.,LTD+86-88938639 +86-17705817739 · [email protected]
南京世洲生物科技有限公司18351873721 · [email protected]
DONBOO AMINO ACID COMPANY13063595538 · [email protected]
Dideu Industries Group Limited+86-29-81148696 +86-15129568250 · [email protected]

Additional notes

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

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes