Skip to Content
Merck
All Photos(2)

Documents

147885

Sigma-Aldrich

4-Phenyl-3-buten-2-one

99%

Synonym(s):

Benzalacetone, Benzylideneacetone, Methyl styryl ketone

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

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

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

SMILES string

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

InChI

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

InChI key

BWHOZHOGCMHOBV-BQYQJAHWSA-N

Looking for similar products? Visit Product Comparison Guide

Related Categories

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

Signal Word

Warning

Hazard Statements

H315,H317

Hazard Classifications

Skin Irrit. 2 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

253.4 °F - closed cup

Flash Point(C)

123 °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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
Hiroyuki Morita et al.
Acta crystallographica. Section F, Structural biology and crystallization communications, 64(Pt 4), 304-306 (2008-04-09)
Benzalacetone synthase (BAS) from Rheum palmatum is a plant-specific type III polyketide synthase that catalyzes the one-step decarboxylative condensation of 4-coumaroyl-CoA with malonyl-CoA to produce the diketide 4-(4-hydroxyphenyl)-but-3-en-2-one. Recombinant BAS expressed in Escherichia coli was crystallized by the sitting-drop vapour-diffusion
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.
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
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service