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278564

Sigma-Aldrich

4′-Hydroxyacetophenone

99%

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Synonym(s):
4-Hydroxyphenylethanone, p-Acetophenol, p-Hydroxyphenyl methyl ketone, Piceol
Linear Formula:
HOC6H4COCH3
CAS Number:
Molecular Weight:
136.15
Beilstein/REAXYS Number:
774355
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

99%

form

solid

bp

147-148 °C/3 mmHg (lit.)

mp

109-111 °C (lit.)

solubility

95% ethanol: 5%, colorless to faintly yellow

SMILES string

CC(=O)c1ccc(O)cc1

InChI

1S/C8H8O2/c1-6(9)7-2-4-8(10)5-3-7/h2-5,10H,1H3

InChI key

TXFPEBPIARQUIG-UHFFFAOYSA-N

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General description

Molecular dynamics simulation study of the two known polymorphs of 4′-hydroxyacetophenone (form I, monoclinic; form II, orthorhombic) has been described.

Application

4′-Hydroxyacetophenone has been used as ketone component in the preparation of 1-aryl-3-phenethylamino-1-propanone hydrochlorides, potential cytotoxic agents, via Mannich reactions.

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Aquatic Chronic 3 - Eye Irrit. 2

wgk_germany

WGK 1

flash_point_f

330.8 °F

flash_point_c

166 °C

ppe

dust mask type N95 (US), Eyeshields, Gloves


Certificates of Analysis (COA)

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Colbie R Chinowsky et al.
Molecular biology of the cell, 31(25), 2803-2815 (2020-10-08)
Brush border microvilli enable functions that are critical for epithelial homeostasis, including solute uptake and host defense. However, the mechanisms that regulate the assembly and morphology of these protrusions are poorly understood. The parallel actin bundles that support microvilli have
Ebru Mete et al.
Molecules (Basel, Switzerland), 12(12), 2579-2588 (2008-02-09)
1-Aryl-3-phenethylamino-1-propanone hydrochlorides 1-10, which are potentialpotent cytotoxic agents, were synthesized via Mannich reactions using paraformaldehyde,phenethylamine hydrochloride as the amine component and acetophenone, 4'-methyl-, 4'-methoxy-, 4'-chloro-, 4'-fluoro-, 4'-bromo-, 2',4'-dichloro-, 4'-nitro-, 4'-hydroxyacetophenone or 2-acetylthiophene as the ketone component. Yields were in the87-98
Carlos E S Bernardes et al.
The journal of physical chemistry. B, 116(17), 5179-5184 (2012-04-12)
A molecular dynamics simulation study of the two known polymorphs of 4′-hydroxyacetophenone (HAP; form I, monoclinic; form II, orthorhombic) is described. The modeling of the lattice energetics was found to be particularly sensitive to the atomic point charge (APC) selection
Xiao Yao et al.
Analytical and bioanalytical chemistry, 388(2), 475-481 (2007-03-03)
Capillary electrophoresis with electrochemical detection has been employed for the determination of p-hydroxyacetophenone, chlorogenic acid, and caffeic acid in Herba Artemisiae Scopariae (the dried sprout of Artemisia scoparia Waldst. et Kit.). The effects of several important factors, such as the
Wiebke Zander et al.
Journal of natural products, 74(6), 1358-1363 (2011-05-20)
A family of six novel p-hydroxyacetophenone amides, 1-6, was isolated from Cystobacter ferrugineus, strain Cb G35. Their structures were elucidated by ESI-TOF mass spectrometry and NMR spectroscopy. Feeding experiments with labeled [¹³C₉,¹⁵N]-tyrosine and [d₁₀]-leucine identified the biosynthetic precursors of 1.

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