219339
L-Ethionine
98%
Synonym(s):
L-2-Amino-4-(ethylthio)butyric acid
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About This Item
Linear Formula:
C2H5SCH2CH2CH(NH2)CO2H
CAS Number:
Molecular Weight:
163.24
UNSPSC Code:
12352103
PubChem Substance ID:
EC Number:
235-966-4
MDL number:
InChI key
GGLZPLKKBSSKCX-YFKPBYRVSA-N
InChI
1S/C6H13NO2S/c1-2-10-4-3-5(7)6(8)9/h5H,2-4,7H2,1H3,(H,8,9)/t5-/m0/s1
SMILES string
CCSCC[C@H](N)C(O)=O
assay
98%
optical activity
[α]22/D +21.7°, c = 1 in 1 M HCl
mp
280 °C (dec.) (lit.)
Biochem/physiol Actions
An analog of methionine that interferes with the normal methylation of DNA and other methylation pathways, and induces pancreatic toxicity and liver cancer. However, in animal studies, it has also been shown to act synergistically with methionine-depletion to block the growth and metastasis of methionine-dependent tumors.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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Erik Alm et al.
Analytical and bioanalytical chemistry, 403(2), 443-455 (2012-03-01)
In (1)H NMR metabolomic datasets, there are often over a thousand peaks per spectrum, many of which change position drastically between samples. Automatic alignment, annotation, and quantification of all the metabolites of interest in such datasets have not been feasible.
Yiannis N Kallis et al.
Gut, 60(4), 525-533 (2010-11-26)
In advanced liver damage, hepatic regeneration can occur through proliferation of a resident hepatic progenitor cell (HPC) population. HPCs are located within a designated niche in close association with myofibroblasts and bone marrow (BM) derived macrophages. Extra-cellular matrix (ECM) laminin
Moncef Benkhalifa et al.
Fertility and sterility, 93(5), 1585-1590 (2009-04-14)
To investigate whether homocysteine, a well known inhibitor of methylation, which is produced after imprinting and other methylation processes, can be recycled to methionine in the oocyte, at least until the stage of maternal to zygotic transition (i.e., four- to
Joanne N Tonkin et al.
Stem cell research, 1(3), 195-204 (2009-04-23)
Liver progenitor (oval) cells have enormous potential in the treatment of patients with liver disease using a cell therapy approach, but their use is limited by their scarcity and the number of donor livers from which they can be derived.
Shuntaro Ikeda et al.
The Journal of reproduction and development, 58(1), 91-97 (2011-11-05)
The roles of methionine metabolism in bovine preimplantation embryo development were investigated by using ethionine, an antimetabolite of methionine. In vitro produced bovine embryos that had developed to the 5-cell stage or more at 72 h after the commencement of
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