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161683

Sigma-Aldrich

4-Cyclopentene-1,3-dione

95%

Synonym(s):

1-Cyclopentene-3,5-dione, 2-Cyclopenten-1,4-dione, 2-Cyclopentene-1,4-dione, Cyclopent-4-en-1,3-dione, Cyclopentene-3,5-dione, Cyclopentenedione

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About This Item

Linear Formula:
C5H4(=O)2
CAS Number:
930-60-9
Molecular Weight:
96.08
Beilstein:
2038507
EC Number:
213-219-3
MDL number:
MFCD00001404
UNSPSC Code:
12352100
PubChem Substance ID:
24849946
NACRES:
NA.22

Assay

95%

form

solid

bp

60 °C/1 mmHg (lit.)

mp

34-36 °C (lit.)

storage temp.

2-8°C

SMILES string

O=C1CC(=O)C=C1

InChI

1S/C5H4O2/c6-4-1-2-5(7)3-4/h1-2H,3H2

InChI key

MCFZBCCYOPSZLG-UHFFFAOYSA-N

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Application

4-Cyclopentene-1,3-dione was used in the synthesis of 2-methoxymethylene-4-cyclopentene-1,3-dione and chrysotrione B (2-acylcyclopentene-1,3-dione derivative). It was used to investigate the influence of sulfiydryl group-specific reagents on activity of bovine heart phospholipid exchange protein.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H317

Hazard Classifications

Acute Tox. 4 Oral - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

183.2 °F - closed cup

Flash Point(C)

84 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Yoshihiro Uto et al.
Bioorganic & medicinal chemistry, 16(11), 6042-6053 (2008-05-14)
We designed chiral 2-nitroimidazole derivatives containing a 2-aminomethylene-4-cyclopentene-1,3-dione moiety as antiangiogenic hypoxic cell radiosensitizers. Based on results of molecular orbital calculations, the 2-aminomethylene-4-cyclopentene-1,3-dione moiety is expected to show high electrophilicity comparable to that of the 2-methylene-4-cyclopentene-1,3-dione moiety included in TX-1123
P E DiCorleto et al.
The Journal of biological chemistry, 254(16), 7795-7802 (1979-08-25)
Two phospholipid exchange proteins from bovine heart have been purified approximately 2000-fold and judged greater than 90% pure. The proteins are similar in molecular weight (both 33,400 by polyacrylamide gel electrophoresis and 23,500 by gel filtration), in amino acid composition
T Bui et al.
Biochimica et biophysica acta, 1397(1), 31-42 (1998-04-18)
The molecular pathways by which the cyclopentenone prostaglandins (PGA and PGJ series) inhibit cell growth and tumorigenicity are poorly understood. These cellular responses may be caused by specific regulation of growth-related and stress-induced genes. A variety of prostaglandins were tested
Gianluca Gilardoni et al.
Journal of natural products, 70(1), 137-139 (2007-01-27)
Chrysotriones A (1) and B (2), two new 2-acylcyclopentene-1,3-dione derivatives, were isolated from the fruiting bodies of the Basidiomycete Hygrophorus chrysodon, and their structures were established by spectroscopic data and synthesis of compound 2. They represent the first examples of
Mona Mokhtari et al.
Journal of agricultural and food chemistry, 66(22), 5531-5539 (2018-03-17)
Pathogenic fungi continue to develop resistance against current antifungal drugs. To explore the potential of agricultural waste products as a source of novel antifungal compounds, we obtained an unbiased GC-MS profile of 151 compounds from 16 commercial and experimental cultivars
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