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Merck
CN

147885

4-Phenyl-3-buten-2-one

99%

Synonym(s):

Benzalacetone, Benzylideneacetone, Methyl styryl ketone

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About This Item

Linear Formula:
C6H5CH=CHCOCH3
CAS Number:
122-57-6
Molecular Weight:
146.19
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24848836
EC Number:
204-555-1
Beilstein/REAXYS Number:
742047
MDL number:
MFCD00008779

Key Documents

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Product Name

4-Phenyl-3-buten-2-one, 99%

InChI key

BWHOZHOGCMHOBV-BQYQJAHWSA-N

InChI

1S/C10H10O/c1-9(11)7-8-10-5-3-2-4-6-10/h2-8H,1H3/b8-7+

SMILES string

[H]\C(=C(\[H])c1ccccc1)C(C)=O

vapor pressure

0.01 mmHg ( 25 °C)

assay

99%

form

solid

bp

260-262 °C (lit.)

mp

39-42 °C (lit.)

solubility

alcohol: freely soluble
benzene: freely soluble
chloroform: freely soluble
diethyl ether: freely soluble
petroleum ether: very slightly soluble
water: very slightly soluble

Quality Level

100

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General description

trans- 4-Phenyl-3-buten-2-one is substrate for glutathione transferase. It reacts with methyl- and benzylguanidine to yield aromatic N2-substituted 2-pyrimidinamines.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H315,H317

Hazard Classifications

Skin Irrit. 2 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

253.4 °F - closed cup

flash_point_c

123 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBT0431
SHBR9221
SHBR6542
SHBQ7199
SHBL9127

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Dihydropyrimidines and related structures. I. N2-substituted 2-pyrimidinamines and dihydro-2-pyrimidinamines by reaction of phenylbutenones and monosubstituted guanidines.
Winfried W and Schermanz K.
Journal of Heterocyclic Chemistry, 21(1), 65-69 (1984)
Glutathione S-transferases. The first enzymatic step in mercapturic acid formation.
W H Habig et al.
The Journal of biological chemistry, 249(22), 7130-7139 (1974-11-25)
Samyeol Seo et al.
Applied and environmental microbiology, 78(11), 3816-3823 (2012-03-27)
The entomopathogenic bacteria Xenorhabdus nematophila and Photorhabdus temperata subsp. temperata suppress insect immune responses by inhibiting the catalytic activity of phospholipase A(2) (PLA(2)), which results in preventing biosynthesis of immune-mediating eicosanoids. This study identified PLA(2) inhibitors derived from culture broths
Bowon Kwon et al.
Journal of economic entomology, 101(1), 36-41 (2008-03-12)
Benzylideneacetone (BZA) is a metabolite of gram-negative entomopathogenic bacterium Xenorhabdus nematophila, and it acts as an enzyme inhibitor against phospholipase A2 (PLA2). PLA2 catalyzes a committed biosynthetic step of eicosanoids, which mediate insect immune reactions to infection by microbial pathogens.
Chisako Yamagami et al.
Bioorganic & medicinal chemistry letters, 14(22), 5629-5633 (2004-10-16)
Antioxidant activities for a series of hydroxybenzalacetones, OH-BZ, were evaluated by measuring inhibitory potencies of OH-BZ against lipid peroxidation induced by t-BuOOH or gamma-irradiation. Their quantitative structure-activity relationship (QSAR) studies indicated that the activities are mainly governed by electronic and
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