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359475

Sigma-Aldrich

Methyl 2-oxo-2H-pyran-3-carboxylate

98%

Synonym(s):

Methyl 2-pyrone-3-carboxylate

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About This Item

Empirical Formula (Hill Notation):
C7H6O4
CAS Number:
25991-27-9
Molecular Weight:
154.12
Beilstein/REAXYS Number:
1424749
EC Number:
247-397-9
MDL number:
MFCD00075443
UNSPSC Code:
12352100
PubChem Substance ID:
24862080
NACRES:
NA.22

Quality Level

200

assay

98%

form

powder

bp

146-148 °C/0.75 mmHg (lit.)

mp

75-77 °C (lit.)

SMILES string

COC(=O)C1=CC=COC1=O

InChI

1S/C7H6O4/c1-10-6(8)5-3-2-4-11-7(5)9/h2-4H,1H3

InChI key

GJVZWOMUTYNUCE-UHFFFAOYSA-N

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General description

Methyl 2-oxo-2H-pyran-3-carboxylate is a cyclic α,β -unsaturated ketone. It activates caspases-3, -8 and -9 weakly in HL-60 cells.

Application

Methyl 2-oxo-2H-pyran-3-carboxylate is suitable reagent used to investigate the series of simple α,β-unsaturated carbonyl compounds for their cytotoxic profiles against oral human normal and tumor cells.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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Risa Takeuchi et al.
Anticancer research, 26(5A), 3343-3348 (2006-11-11)
As previously suggested, codeinone (oxidation product of codeine) induces non-apoptotic cell death, characterized by marginal caspase activation and the lack of DNA fragmentation in HL-60 human promyelocytic leukemia cells, which was inhibited by N-acetyl-L-cysteine. Whether, morphinone, an oxidative metabolite of
Tohru Nakayachi et al.
Anticancer research, 24(2B), 737-742 (2004-05-27)
A series of simple alpha, beta-unsaturated carbonyl compounds (1-26) was characterized for their cytotoxic profiles against oral human normal and tumor cells. Several cycloalkenones showed potent cytotoxic activities against human oral squamous cell carcinoma HSC-2 cell line. Among them, 4,4-dimethyl-2-cyclopenten-1-one

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