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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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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
Joanna Malinowska et al.
Nutrition (Burbank, Los Angeles County, Calif.), 28(7-8), 793-798 (2012-01-21)
Aronia melanocarpa fruits (Rosaceae) are one of the richest plant sources of phenolic substances, and it has been shown to have various biological activities. Berries of A. melanocarpa (chokeberry) have been supposed to be beneficial for the prevention of cardiovascular
Root-growth inhibition by DL-homocysteine thiolactone and its related compounds.
Inamori Y, et al.
Bioscience, Biotechnology, and Biochemistry, 59(3), 523-525 (1995)
Kotchakorn Juntapram et al.
Carbohydrate polymers, 90(4), 1469-1479 (2012-09-05)
Novel hydrogel polyelectrolyte complexes (PECs) between the N,N,N,-trimethylchitosan-homocysteine thiolactone (TM-HT-chitosan) and two anionic polymers were investigated. The particles of pure thiolated chitosan and its PECs with alginate and carrageenan were fabricated using the electrospray ionization technique. The hydrogel PEC particles
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