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P3755

Sigma-Aldrich

6-Propyl-2-thiouracil

enzyme inhibitor

Synonym(s):

2,3-Dihydro-6-propyl-2-thioxo-4(1H)-pyrimidinone, 4-Hydroxy-2-mercapto-6-propylpyrimidine

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About This Item

Empirical Formula (Hill Notation):
C7H10N2OS
CAS Number:
51-52-5
Molecular Weight:
170.23
Beilstein:
130039
EC Number:
200-103-2
MDL number:
MFCD00006041
UNSPSC Code:
41106305
PubChem Substance ID:
24898446
NACRES:
NA.51

description

enzyme inhibitor

Quality Level

200

Assay

≥99% (HPLC)

form

powder

mp

218-220 °C (lit.)

solubility

10% NH3: 100 mg/mL, clear to slightly hazy, colorless to faintly yellow

SMILES string

CCCC1=CC(=O)NC(=S)N1

InChI

1S/C7H10N2OS/c1-2-3-5-4-6(10)9-7(11)8-5/h4H,2-3H2,1H3,(H2,8,9,10,11)

InChI key

KNAHARQHSZJURB-UHFFFAOYSA-N

Gene Information

human ... DIO1(1733) , TPO(7173)

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General description

6-Propyl-2-thiouracil or 6-n-Propylthiouracil (PROP) is a compound with a bitter taste.

Application

6-Propyl-2-thiouracil (PROP) has been used to impregnate on disk for PROP taster status studies for sensory characterization in a defined human sample group. It has been used as a screening agent for testing the intensity of taste by labeled magnitude scale (LMS).
6-Propyl-2-thiouracil is a thyreostatic (thyroid hormone) agent that may be used as a reference material in thyreostatic drug separation and detection technologies such as capillary electrophoresis, high performance liquid chromatography (HPLC), or gas chromatography.

Biochem/physiol Actions

6-Propyl-2-thiouracil (6-PTU), a potential inhibitor of D1 iodothyronine deiodinase, is involved in the deiodination of iodothyronines. It is an uncompetitive inhibitor of iodothyronine substrates.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H302,H351

Hazard Classifications

Acute Tox. 4 Oral - Carc. 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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Tyler S Allison et al.
PloS one, 15(8), e0237142-e0237142 (2020-08-09)
Electrical stimulation of nerve endings in the tongue can be used to communicate information to users and has been shown to be highly effective in sensory substitution applications. The anterior tip of the tongue has very small somatosensory receptive fields
Adiposity in middle-aged women is associated with genetic taste blindness to 6-n-propylthiouracil
Goldstein G L, et al.
Obesity Research, 13(6), 1017-1023 (2005)
Characterization of recombinant Xenopus laevis type I iodothyronine deiodinase: substitution of a proline residue in the catalytic center by serine (Pro132Ser) restores sensitivity to 6-propyl-2-thiouracil
Kuiper George GJM, et al.
Endocrinology, 147(7), 3519-3529 (2006)
Louise Ramhøj et al.
PeerJ, 7, e7181-e7181 (2019-07-11)
Relative gene expression data obtained from quantitative RT-PCR (RT-qPCR) experiments are dependent on appropriate normalization to represent true values. It is common to use constitutively expressed endogenous reference genes (RGs) for normalization, but for this strategy to be valid the
Daniel Glinoer et al.
Current opinion in endocrinology, diabetes, and obesity, 19(5), 402-407 (2012-07-24)
To bring to the attention of healthcare professionals the additional information on propylthiouracil (PTU)-related hepatotoxicity, based on a reanalysis of medical files reported to the Food and Drug Administration (1982-2008) for acute liver failure in PTU-treated hyperthyroid patients, and propose
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