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Sigma-Aldrich

trans-Chalcone

97%

Synonym(s):

Benzylideneacetophenone

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About This Item

Linear Formula:
C6H5CH=CHCOC6H5
CAS Number:
614-47-1
Molecular Weight:
208.26
EC Number:
210-383-8
MDL number:
MFCD00003082
UNSPSC Code:
12352100
PubChem Substance ID:
24848257
NACRES:
NA.22

Assay

97%

form

solid

bp

208 °C/25 mmHg (lit.)

mp

55-57 °C (lit.)

SMILES string

[H]\C(=C(\[H])C(=O)c1ccccc1)c2ccccc2

InChI

1S/C15H12O/c16-15(14-9-5-2-6-10-14)12-11-13-7-3-1-4-8-13/h1-12H/b12-11+

InChI key

DQFBYFPFKXHELB-VAWYXSNFSA-N

Gene Information

human ... IL1B(3553)
rat ... Ar(24208)

Related Categories

General description

trans-Chalcone is an open chain flavonoid that may prevent lung and forestomach cancer.

Application

trans-Chalcone was used in the synthesis of cis and trans diphenyl cyclopropane. It was also used in screening of surface adsorbed species of isobutybenzene and 4-isobutylacetophenone on bulk fosfotungstic Wells-Dawson acid (H6P2W18O62.xH2O).

Biochem/physiol Actions

trans-Chalcone exhibits antifungal activity against Trichophyton rubrum. It is inhibitor of fatty acid synthase and α-amylase. It induces programmed cell death due to reduced mitochondrial transmembrane potential in Arabidopsis thaliana roots.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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’.

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Tamires Aparecida Bitencourt et al.
BMC complementary and alternative medicine, 13, 229-229 (2013-09-21)
Fatty acid synthase (FAS) is a promising antifungal target due to its marked structural differences between fungal and mammalian cells. The aim of this study was to evaluate the antifungal activity of flavonoids described in the scientific literature as FAS
Asymmetric induction with β-cyclodextrin: cis-trans photoisomerization of diphenyl-cyclopropane and its derivatives.
Koodanjeri S, et al.
Proceedings of the Indian Academy of Sciences - Section A, 68(5), 453-463 (2002)
Carla Díaz-Tielas et al.
Plant, cell & environment, 35(8), 1500-1517 (2012-03-21)
Chalcone (1,3-diphenyl-2-propen-1-one) is an aromatic ketone precursor of important molecules in plants such as flavonoids or anthocyanins. Its phytotoxicity has been demonstrated on different plant species, but to date little is known about the mechanisms of action of this secondary
K L Lahtchev et al.
European journal of medicinal chemistry, 43(10), 2220-2228 (2008-02-19)
We reported the synthesis, antifungal evaluation and study on substituent effects of 21 chalcones. A lot of genetically defined strains belonging to different yeast genera and species, namely Saccharomyces cerevisiae, Hansenula polymorpha and Kluyveromyces lactis, were used as test organisms.
Franco Chimenti et al.
Journal of medicinal chemistry, 52(9), 2818-2824 (2009-04-22)
A large series of substituted chalcones have been synthesized and tested in vitro for their ability to inhibit human monoamine oxidases A and B (hMAO-A and hMAO-B). While all the compounds showed hMAO-B selective activity in the micro- and nanomolar
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