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S4921

Sigma-Aldrich

trans-Stilbene oxide

trans-Stilbene oxide

98%

Synonym(s):

trans-1,2-Diphenyloxirane

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About This Item

Empirical Formula (Hill Notation):
C14H12O
CAS Number:
1439-07-2
Molecular Weight:
196.24
Beilstein:
82740
EC Number:
215-877-7
MDL number:
MFCD00064311
UNSPSC Code:
12352100
PubChem Substance ID:
24899623
NACRES:
NA.22
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Assay

98%

mp

65-67 °C (lit.)

SMILES string

O1[C@@H]([C@H]1c2ccccc2)c3ccccc3

InChI

1S/C14H12O/c1-3-7-11(8-4-1)13-14(15-13)12-9-5-2-6-10-12/h1-10,13-14H/t13-,14-/m1/s1

InChI key

ARCJQKUWGAZPFX-ZIAGYGMSSA-N

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General description

Trans-stilbene oxide also known as trans-1,2-Diphenyloxirane, is often used in photochemistry, whereit can change its structure when exposed to light.Stilbene oxides can break apart when they are excited bylight, leading to the formation of carbonyl ylides. It is also commonlyused to produce trans-stilbene sulfides. [1]

Application

  • Chiral Stationary Phases for Liquid Chromatography: Trans-stilbene oxide has been utilized in the fabrication of cellulose derivative-coated spherical covalent organic frameworks, serving as chiral stationary phases for high-performance liquid chromatographic enantioseparation, demonstrating its pivotal role in advanced analytical methodologies (Yan et al., 2022).
  • Method Selection for Chiral High-Performance Liquid Chromatography: Its application extends to the utilization of hysteresis phenomena for chiral high-performance liquid chromatographic method selection in polar organic mode, enhancing the efficiency and specificity of pharmaceutical compound analysis (Horváth et al., 2020).
  • Adsorption Properties for Enantioseparations: The effect of chiral selector loading on the adsorption properties of fully- and superficially-porous particles is crucial for high-efficient ultrafast enantioseparations, where trans-stilbene oxide derivatives play a significant role (Felletti et al., 2018).
  • Catalysis in Alkene Epoxidation: Trans-stilbene oxide is involved in innovative catalysis research, specifically in the development of carbon nitride-supported Fe(2) cluster catalysts for alkene epoxidation, showcasing its utility in sustainable chemical synthesis (Tian et al., 2018).

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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Certificates of Analysis (COA)

Lot/Batch Number
1451394V
BCBK9142V
1451387V
1451396
1451391

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Photochemistry of cis-and trans-stilbene oxides
Lee, George A
The Journal of Organic Chemistry, 41, 2656-2658 (1976)
Richard Lonsdale et al.
Biochemistry, 51(8), 1774-1786 (2012-01-28)
Soluble epoxide hydrolase (sEH) is an enzyme involved in drug metabolism that catalyzes the hydrolysis of epoxides to form their corresponding diols. sEH has a broad substrate range and shows high regio- and enantioselectivity for nucleophilic ring opening by Asp333.
B Schilter et al.
The Journal of pharmacology and experimental therapeutics, 294(3), 916-922 (2000-08-17)
Oxidative biotransformation, coupled with genetic variability in enzyme expression, has been the focus of hypotheses interrelating environmental and genetic factors in the etiology of central nervous system disease processes. Chemical modulation of cerebral cytochrome P450 (P450) monooxygenase expression character may
Kouhei Shimomura et al.
Nature chemistry, 6(5), 429-434 (2014-04-24)
In the chromatographic separation of enantiomers the order of elution is determined by the strength of diasteromeric interactions between the components of the mixture and a chiral stationary phase. For analytical purposes, it is ideal to have the minor component
Paloma Vidal et al.
The Journal of organic chemistry, 72(9), 3166-3170 (2007-03-10)
This study presents a simple method for measuring long-range heteronuclear coupling constants between protons and proton-bearing carbons. The approach involves recording two conventional 1D-TOCSY experiments in which the offset of the selective proton pulse is set on the low- and
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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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