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105449

Sigma-Aldrich

γ-Thiobutyrolactone

98%

Synonym(s):

4-Butyrothiolactone

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About This Item

Empirical Formula (Hill Notation):
C4H6OS
CAS Number:
1003-10-7
Molecular Weight:
102.15
EC Number:
213-700-8
MDL number:
MFCD00005479
UNSPSC Code:
12352100
PubChem Substance ID:
24846697
NACRES:
NA.22

Assay

98%

refractive index

n20/D 1.523 (lit.)

bp

39-40 °C/1 mmHg (lit.)

solubility

THF: soluble

density

1.18 g/mL at 25 °C (lit.)

SMILES string

O=C1CCCS1

InChI

1S/C4H6OS/c5-4-2-1-3-6-4/h1-3H2

InChI key

KMSNYNIWEORQDJ-UHFFFAOYSA-N

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General description

γ-Thiobutyrolactone undergoes copolymerization with glycidyl phenyl ether to form poly(ester-alt-sulfide).

Application

γ-Thiobutyrolactone was used to terminate the ring opening polymerization of ω-pentadecalactone to synthesize difunctional polyesters. γ-Thiobutyrolactone was used to study the mechanism of metabolism of sulphur containing heterocyclic compounds by lignin-degrading basidiomycete Coriolus versicolor.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

186.8 °F - closed cup

Flash Point(C)

86 °C - closed cup

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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Tiny droplets make a big splash.
Michael Eisenstein
Nature methods, 3(2), 71-71 (2006-02-14)
Jonathan Garel et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 12(15), 4144-4152 (2006-02-03)
Homocysteine thiolactone (tHcy) is deemed a risk factor for cardiovascular diseases and strokes, presumably because it acylates the side chain of protein lysine residues ("N-homocysteinylation"), thereby causing protein damage and autoimmune responses. We analysed the kinetics of hydrolysis and aminolysis
Nishikubo et al.
Macromolecules, 31(15), 4746-4752 (1998-07-29)
Poly(ester-alt-sulfide) (polymer 1) was synthesized by the alternating copolymerization of glycidyl phenyl ether (GPE) with gamma-thiobutyrolactone (TBL) catalyzed by either quaternary onium salts or crown ether complexes. The copolymerization proceeded to produce polymer 1 with good yields in neat or
K D Holland et al.
Brain research, 615(1), 170-174 (1993-06-25)
Effects of alkyl-substituted gamma-butyrolactones and gamma-thiobutyrolactones on [35S]t-butylbicyclophosphorothionate (35S-TBPS) dissociation from the picrotoxinin receptor were studied. Unlike picrotoxinin, these lactones accelerated the dissociation rate of 35S-TBPS. Thus, previous reports that these lactones change the Kd but not the Bmax of
One-pot difunctionalization of poly (ω-pentadecalactone) with thiol-thiol or thiol-acrylate groups, catalyzed by Candida antarctica lipase B.
Takwa M, et al.
Macromolecular Rapid Communications, 27(22), 1932-1936 (2006)
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