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147885

Sigma-Aldrich

4-Phenyl-3-buten-2-one

99%

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Synonym(s):
Benzalacetone, Benzylideneacetone, Methyl styryl ketone
Linear Formula:
C6H5CH=CHCOCH3
CAS Number:
Molecular Weight:
146.19
Beilstein/REAXYS Number:
742047
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

vapor pressure

0.01 mmHg ( 25 °C)

Quality Level

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

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1 of 4

This Item
M87509517895241091
4-Phenyl-3-buten-2-one 99%

147885

4-Phenyl-3-buten-2-one

3-Buten-2-one contains 0.3-1.0% hydroquinone as stabilizer, technical grade, 90%

M87509

3-Buten-2-one

trans-4-Phenyl-3-buten-2-one ≥99%

241091

trans-4-Phenyl-3-buten-2-one

solubility

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

solubility

H2O: soluble

solubility

-

solubility

alcohol: freely soluble(lit.), benzene: freely soluble(lit.), chloroform: freely soluble(lit.), diethyl ether: freely soluble(lit.), petroleum ether: very slightly soluble(lit.), water: very slightly soluble(lit.)

form

solid

form

liquid

form

-

form

solid

bp

260-262 °C (lit.)

bp

81 °C (lit.)

bp

260-262 °C (lit.)

bp

260-262 °C (lit.)

mp

39-42 °C (lit.)

mp

-

mp

39-42 °C (lit.)

mp

39-41 °C (lit.)

vapor pressure

0.01 mmHg ( 25 °C)

vapor pressure

310 mmHg ( 55 °C), 71 mmHg ( 20 °C)

vapor pressure

-

vapor pressure

0.01 mmHg ( 25 °C)

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

signalword

Warning

Hazard Classifications

Skin Irrit. 2 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

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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2-METHYL-4-PHENYL-3-BUTEN-2-OL

4-Phenyl-3-butyn-2-ol 97%

Sigma-Aldrich

669288

4-Phenyl-3-butyn-2-ol

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)
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
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

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