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53530

Sigma-Aldrich

DL-Homocysteine thiolactone hydrochloride

≥99.0% (AT)

Synonym(s):

DL-2-Amino-4-mercaptobutyric acid 1,4-thiolactone hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C4H7NOS · HCl
CAS Number:
6038-19-3
Molecular Weight:
153.63
Beilstein:
3689338
EC Number:
227-923-3
MDL number:
MFCD00012724
UNSPSC Code:
12352100
eCl@ss:
42021308
PubChem Substance ID:
57651419
NACRES:
NA.22

Quality Level

200

Assay

≥99.0% (AT)

form

solid

loss

≤0.5% loss on drying

mp

202 °C (dec.) (lit.)
~203 °C (dec.)

SMILES string

Cl[H].NC1CCSC1=O

InChI

1S/C4H7NOS.ClH/c5-3-1-2-7-4(3)6;/h3H,1-2,5H2;1H

InChI key

ZSEGSUBKDDEALH-UHFFFAOYSA-N

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General description

DL-Homocysteine thiolactone hydrochloride (HTL-HCl) is a cyclic amino acid derivative that exhibits root-growth inhibitory activity.

Application

DL-Homocysteine thiolactone hydrochloride may be used in the preparation of:
  • DL-buthionine
  • DL-homocysteine
  • poly[α,β-(N-2-aminoethyl-dl-aspartamide)]-poly[α,β-(N-2-hydroxyethyl-dl-aspartamide)]-poly[α,β-(N-3-mercapto-1-methoxycarbonyl-propyl-dl-aspartamide)] copolymer diclofenac conjugate (PAHMA-Dic)
  • bis[ S-(dimethylarsino)homocysteine]

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319

Precautionary Statements

P302 + P352 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Reza Yousefi et al.
International journal of biological macromolecules, 51(3), 291-298 (2012-05-29)
In the current study both structural alteration and fibrillation of insulin were studied in the presence of homocysteine thiolactone (HCTL). The spectroscopic studies revealed that HCTL increases rate of insulin unfolding, giving rise to the appearance of solvent-exposed hydrophobic regions
Jerott R Moore et al.
Journal of neuroimmunology, 324, 100-114 (2018-09-30)
We investigated how one calcitriol dose plus vitamin D3 reverses experimental autoimmune encephalomyelitis (EAE), a multiple sclerosis model. This protocol rapidly increased CD4+ T cell Ikzf2 transcripts, Helios protein, and CD4+Helios+FoxP3+ T regulatory cells. It also rapidly increased CD4+ T
Joanna Malinowska et al.
Platelets, 22(4), 277-283 (2011-05-12)
Resveratrol (3,4',5-trihydroxystilben), a phenolic antioxidant synthesized in grapes and other plants, and also present in wine, has been suggested to help prevent cardiovascular events. In this study the influence of resveratrol on platelet aggregation during a model of hyperhomocysteinemia was
O W Griffith et al.
The Journal of biological chemistry, 254(16), 7558-7560 (1979-08-25)
Buthionine sulfoximine (S-n-butyl homocysteine sulfoximine), the most potent of a series of analogs of methionine sulfoximine thus far studied (Griffith, O.W., Anderson, M.E., and Meister, A. (1979) J. Biol. Chem. 254, 1205-1210), inhibited gamma-glutamylcysteine synthetase about 20 times more effectively
Hieronim Jakubowski et al.
Advances in clinical chemistry, 55, 81-103 (2011-12-01)
Protein-related homocysteine (Hcy) metabolism produces Hcy-thiolactone, N-Hcy-protein, and N epsilon-homocysteinyl-lysine (N epsilon-Hcy-Lys). Hcy-thiolactone is generated in an error-editing reaction in protein biosynthesis when Hcy is erroneously selected in place of methionine by methionyl-tRNA synthetase. Hcy-thiolactone, an intramolecular thioester, is chemically
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