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42995

Sigma-Aldrich

trans-1,3-Diphenyl-2,3-epoxypropan-1-one

≥98.0%

Synonym(s):

trans-2-Benzoyl-3-phenyloxirane, trans-Benzalacetophenone oxide

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About This Item

Empirical Formula (Hill Notation):
C15H12O2
CAS Number:
7570-86-7
Molecular Weight:
224.25
Beilstein:
84132
MDL number:
MFCD00066320
UNSPSC Code:
12352100
PubChem Substance ID:
57650138
NACRES:
NA.22

Assay

≥98.0%

form

solid

mp

86-89 °C (lit.)

functional group

ether
ketone
phenyl

SMILES string

O=C([C@H]1O[C@@H]1c2ccccc2)c3ccccc3

InChI

1S/C15H12O2/c16-13(11-7-3-1-4-8-11)15-14(17-15)12-9-5-2-6-10-12/h1-10,14-15H/t14-,15-/m1/s1

InChI key

UQGMJZQVDNZRKT-HUUCEWRRSA-N

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General description

trans-1,3-Diphenyl-2,3-epoxypropan-1-one has been reported to efficiently participate in gas-phase Meerwein reaction under both electrospray ionization (ESI) and atmospheric pressure chemical ionization (APCI) conditions. Therapeutic potential of trans-1,3-diphenyl-2,3-epoxypropane-1-one (DPEP), and its anti-inflammatory effects have been studied.

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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Lot/Batch Number
379277/1

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Giulia Licini et al.
Biopolymers, 84(1), 97-104 (2005-08-27)
C(alpha)-tetrasubstituted alpha-amino acids constitute a powerful tool for controlling the conformation of short peptide sequences. Chiral peptides may be used in stereoselective reactions both for asymmetric induction and in kinetic resolution. By reviewing recent data from our own laboratories and
E C Dietze et al.
Biochemical pharmacology, 42(6), 1163-1175 (1991-08-22)
The inhibition of murine cytosolic epoxide hydrolase has been studied with both racemic and enantiomerically pure trans-3-phenylglycidols. These compounds are the first enantioselective, slow binding inhibitors of cytosolic epoxide hydrolase. The (2S,3S)-3-phenylglycidol enantiomer was always a better inhibitor than the
G D Prestwich et al.
Archives of biochemistry and biophysics, 242(1), 11-15 (1985-10-01)
Chalcone oxides and several isosteric compounds have been prepared to examine the importance of the alpha,beta-epoxyketone moiety in the inhibition of the hydrolysis of [3H]-trans-stilbene oxide to its meso-diol by mouse liver cytosolic epoxide hydrolase (cEH). Inhibition of microsomal EH
J Seidegård et al.
European journal of biochemistry, 112(3), 643-648 (1980-12-01)
Benzil was found to be a very potent activator of microsomal epoxide hydrolase activity (measured with styrene oxide as substrate) in vitro. The activating effect was uncompetitive and benzil causes approximately ninefold increases in both the apparent V and the
Folami Lamoke et al.
Experimental eye research, 93(4), 350-354 (2011-03-01)
Retinal neovascularization (RNV) is a critical pathological event and a major cause of blindness. Vascular inflammation and oxidative stress have been shown to play a key role in the induction and progression of RNV. Trans-Chalcone-derived flavonoids have been previously shown
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