136123
trans-Chalcone
97%
Synonym(s):
Benzylideneacetophenone
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About This Item
Linear Formula:
C6H5CH=CHCOC6H5
CAS Number:
Molecular Weight:
208.26
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Assay
97%
form
solid
bp
208 °C/25 mmHg (lit.)
mp
55-57 °C (lit.)
functional group
ketone
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
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
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Sylvie Ducki et al.
Bioorganic & medicinal chemistry, 17(22), 7698-7710 (2009-10-20)
The alpha-methyl chalcone SD400 is a potent inhibitor of tubulin assembly and possesses potent anticancer activity. Various chalcone analogues were synthesized and evaluated for their cell growth inhibitory properties against the K562 human chronic myelogenous leukemia cell line (SD400, IC(50)
Yi-Kun Chiang et al.
Journal of medicinal chemistry, 52(14), 4221-4233 (2009-06-11)
A pharmacophore model, Hypo1, was built on the basis of 21 training-set indole compounds with varying levels of antiproliferative activity. Hypo1 possessed important chemical features required for the inhibitors and demonstrated good predictive ability for biological activity, with high correlation
Saeed Attar et al.
Bioorganic & medicinal chemistry, 19(6), 2055-2073 (2011-02-26)
A series of 30 organic chlacones and 33 ferrocenyl (Fc) chalcones were synthesized and characterized by melting point, elemental analysis, spectroscopy ((1)H NMR and FTIR) and, in two cases, by X-ray crystallography. The biological activity of each compound (10(-4)M in
Asha Budakoti et al.
European journal of medicinal chemistry, 44(3), 1317-1325 (2008-04-02)
In an effort to develop potent antiamoebic agents, we have synthesized chalcones (1-8), amino-5-substituted-(3-phenyl(2-pyrazolinyl))methane-1-thione derivatives (1a-8a) and 2-(5-substituted-3-phenyl-2-pyrazolinyl)-1,3-thiazolino[5,4-b]quinoxaline derivatives (1b-8b) and evaluated for their in vitro antiamoebic activity against HM1:IMSS strain of E. histolytica. All the compounds were characterized by
Wattenberg L.W., et al.
Cancer Letters, 15, 165-165 (1994)
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