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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
T M Guenthner
Biochemical pharmacology, 35(19), 3261-3266 (1986-10-01)
A nuclear envelope-associated epoxide hydrolase in mouse liver that hydrates trans-stilbene oxide has been identified and characterized. This epoxide hydrolase is distinct from the enzyme in nuclear envelopes that hydrates benzo[a]pyrene 4,5-oxide and other arene oxides. This distinction was demonstrated
Eduardo C Meurer et al.
Journal of mass spectrometry : JMS, 41(4), 470-476 (2006-02-25)
We have already shown that the in-vacuum gas-phase Meerwein reaction of (thio)acylium ions is general in nature and useful for class-selective screening of cyclic (thio)epoxides. Herein we report that this gas-phase reaction can also be performed efficiently at atmospheric pressure
J Seidegård et al.
European journal of biochemistry, 159(2), 415-423 (1986-09-01)
The influence of metyrapone, chalcone epoxide, benzil and clotrimazole on the activity of microsomal epoxide hydrolase towards styrene oxide, benzo[a]pyrene 4,5-oxide, estroxide and androstene oxide was investigated. The studies were performed using liver microsomes from rats, rabbits, mice and humans;
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